Isoxazolines for invertebrate pest control

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (1), where A1, A2, A3, A4, A5 ad A6 are independently selected from a group comprising CR3 and N; provided that the biggest one of A1, A2, A , A4, A5 and A6 denotes N; B1, B2 and B3 are independently selected from a group comprising CR2 and N; each R3 independently denotes H or C1-C6 alkyl; and R1, R2, R4, R5, W and n are as given in the description, or salts thereof which are suitable for use in agriculture. The invention also relates to compositions containing compounds of formula (1), and insect-pest control methods which involve contact between the pest or habitat thereof with a biologically effective amount of the compound or composition according to the present invention, as well as to methods of protecting seeds and animals from insects-pests.

EFFECT: high effectiveness of the obtained compounds in insect-pest control.

29 cl, 12 tbl, 5 ex

 

The present invention relates to certain isoxazolines,N-oxides, salts and compositions suitable for agricultural and non-agricultural applications, including applications, described below, and to methods of their use for combating invertebrate pests such as arthropods, both in agricultural and non-agricultural fields.

Combating invertebrate pests is extremely important to achieve high yields. Damage to invertebrate pests of growing and stored crops can cause significant performance degradation and, thus, lead to higher costs for consumers.

Combating invertebrate pests of forestry, greenhouse crops, ornamentals, seedlings, stored food and fiber materials, livestock, household, lawn, timber, human and animal health is also important. For these purposes, there are many industrial products, but there is still a need for new compounds that are more effective, less costly, less toxic, more environmentally safe, or which have different modes of action.

In the patent PCT WO 05/085216 described derivatives isoxazole the formulas ias insecticides:

where, inter alia, each of the A1, A2and A3independently represents C or N; G is a benzene ring; W represents O or S; and X is halogen or C1-C6halogenation.

The present invention relates to compounds of the formula1including all geometric and stereoisomers, N-oxides and their salts, and to compositions containing them and their use for combating invertebrate pests:

where

A1, A2, A3, A4, A5and A6independently selected from the group consisting of CR3and N, provided that at most 3 of the A1, A2, A3, A4, A5and A6represent N;

B1B2and B3independently selected from the group consisting of CR2and N;

W represents O or S;

R1represents a C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R6;

each R2independently represents H, halogen, C1-C6alkyl, C1-C6Gal is penalcol, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, C2-C4alkoxycarbonyl, -CN or-NO2;

each R3independently represents H, halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, -CN or-NO2;

R4represents H, C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes, C4-C7cycloalkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl;

R5represents H, OR10, NR11R12or Q1; or (C1-C6alkyl, C2 -C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7; or

R4and R5together with the nitrogen atom to which they are attached, form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, and the specified ring optionally substituted by 1-4 substituents, independently selected from the group consisting of C1-C2of alkyl, halogen, - CN, -NO2and C1-C2alkoxy;

each R6independently represents halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, - CN or-NO2;

each R7independently represents halogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C7alkylsulphonyl, C2-C7alkoxycarbonyl, C2-C7alkylaminocarbonyl, C 3-C9dialkylaminoalkyl, C2-C7halogenoalkanes, C2-C7halogenosilanes, C2-C7halogenlithiumcarbeniod, C3-C9halogenoaluminates, hydroxy, -NH2, -CN or-NO2; or Q2;

each R8independently represents halogen, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, C2-C4alkoxycarbonyl, -CN or-NO2;

each R9independently represents halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, -CN, -NO2, phenyl or pyridinyl;

R10represents H; or C1-C6/sub> alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more Halogens;

R11represents H, C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes, C4-C7cycloalkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl;

R12represents H; Q3; or (C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7; or

R11and R12together with the nitrogen atom to which they are attached, form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, and the specified ring optionally substituted by 1-4 substituents, independently selected from the group consisting of C1-C2of alkyl, halogen, -CN, -NO2and C1-C2alkoxy;

Q1is a phenyl ring, a 5 - or 6-membered gets aziklicescoe ring, or 8-, 9 - or 10-membered condensed bicyclic ring system, optionally containing one to three heteroatoms selected from not more than 1 atom of O, not more than 1 atom S and no more than 3 atoms of N, each ring or ring system optionally substituted by one or more substituents independently selected from R8;

each Q2independently represents a phenyl ring or a 5 - or 6-membered heterocyclic ring, each ring optionally substituted by one or more substituents independently selected from R9;

Q3is a phenyl ring or a 5 - or 6-membered heterocyclic ring, each ring optionally substituted by one or more substituents independently selected from R9; and

n is 0, 1 or 2.

The present invention also provides a composition comprising a compound of the formula1its N-oxide or salt and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. In one embodiment, the present invention also provides a composition for combating invertebrate pests, containing a biologically effective amount of a compound of the formula1hisNoxide or Sol and, at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, and the specified composition optionally further comprises a biologically effective amount of at least one additional biologically active compound or agent.

The present invention also provides a sprayable composition for combating invertebrate pests, containing a biologically effective amount of a compound of the formula1hisNoxide or salt, or composition, described above, and a propellant. The present invention also provides a bait composition for combating invertebrate pests, containing a biologically effective amount of a compound of the formula1its N-oxide or salt, or composition, described in the embodiment above, one or more nutrients, optionally an attractant, and optionally a wetting agent.

The present invention also provides a trap for combating invertebrate pests containing the specified baiting composition and a housing adapted for placement compositions for bait, where the housing has at least one hole, the dimensions of which allow bespozvonochnykh pest to pass through the hole at back is s, resulting in the invertebrate pest can gain access to the bait composition from a position outside the housing, where the housing is additionally adapted for placement on the site or near the site of potential or known activity bespozvonochnykh pest.

The present invention also provides a method of combating invertebrate pest comprising contacting bespozvonochnykh pest or its environment with a biologically effective amount of the compounds of formula1its N-oxide or a salt (for example, in the form of a composition described herein). The present invention also relates to such method, in which the invertebrate pest or its habitat in contact with a composition comprising a biologically effective amount of a compound of the formula1hisNoxide or salt and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, and the specified composition optionally further comprises a biologically effective amount of at least one additional biologically active compound or agent.

Detailed description of the invention

Used herein, the terms "includes", "including", "has", "with", "contains the" or "containing" or any other variations are intended to cover non-exclusive inclusion. For example, composition, mixture, method, product or device, which include a number of elements, not necessarily confined to these elements, and may also include other elements not listed directly or inherent specified composition, mixture, method, product or device. Further, unless expressly stated to the contrary, "or" refers to the inclusive "or"rather than an exclusive "or". For example, a condition A or B is satisfied by any of the following: A is true (or present)and B is false (or not present), A is false (or not present)and B is true (or present), or both A and B are true (or present).

In addition, indefinite articles preceding element or component of the invention, are not intended to be limiting as to the number of examples (cases) of the element or component. Therefore indefinite articles should include "one" or "at least one", and the word element or component in the singular also includes the plural, except when the number is not explicitly indicated only.

Specified in the present description the term "invertebrate pest" includes arthropods, gastropods and nematodes, which are pests of economic importance. The concept of "arthropods" includes insects, mites, spiders, Skorpio is s, of insects, centipedes, woodlice and Simpel. The concept of "gastropod" includes snails, slugs and other representatives stabilisatoren. The concept of "worms" includes worms typesNemathelminth,PlatyhelminthandAcanthocephalasuch as roundworms, dirofilaria and herbivorous nematodes (Nematoda), suckers (Trematoda), tapeworms (Cestodaand calyceraceae worms.

In the context of the present description "combating invertebrate pests" means the prevention of the development of invertebrate pests (including death, reduced power and/or disruption of mating), while the dependent expressions defined in the same way.

The term "agriculture" refers to the production of field crops, such as food and textiles, and includes the cultivation of corn, soybeans and other legumes, rice, cereals (e.g. wheat, oats, barley, rye, rice, corn), leafy vegetables (e.g. lettuce, cabbage, cabbage and other crops), fruit vegetables (e.g. tomatoes, peppers, eggplant, mustard and pumpkin cultures), potato, sweet potato, grapes, cotton, fruit trees (for example, pome fruit, stone fruit and citrus), Bush fruit crops (berries, cherries)and other crops (e.g. canola, sunflower, olive). The concept of "non-agricultural" refers to other horticultural crops (such as greenhouse plants, the young plants or ornamental plants not growing in the field), residential and commercial structures in urban and industrial environments, lawns (for example, pasture farms, pastures, Golf course, lawns in residential areas, entertainment and sports venues, etc.), timber, stored products, agroservices and monitoring of vegetation health (human) and animal health (e.g., domesticated animals, such as Pets, livestock and poultry, untamed animals, such as wild animals).

In the above listing, the term "alkyl", used alone or in compound words such as "alkylthio" or "halogenated"includes unbranched and branched alkyl, such as methyl, ethyl,n-propyl, isopropyl or the different butyl isomers, pentile or exile. "Alkenyl includes an unbranched or branched alkenes, such as ethynyl, 1-propenyl, 2-propenyl and various isomers butenyl, pentenyl and hexenyl. "Alkenyl also includes a polyene, such as 1,2-PROPADIENE and 2,4-hexadienyl. "Quinil includes unbranched or branched alkynes such as ethinyl, 1-PROPYNYL, 2-PROPYNYL and the different isomers of butenyl, pentenyl and hexenyl. "Quinil" may also include molecules consisting of multiple triple relations, for example 2,5-hexadien the L.

"Alkoxy" includes, for example, methoxy, ethoxy,n-propoxy, isopropoxy and various isomers of butoxy, pentox, hexyloxy. "Alkylthio" includes branched or unbranched of allylthiourea, such as methylthio, ethylthio and various isomers of property, butylthio, pentylthio and exeltium. "Alkylsulfonyl" includes both enantiomers alkylsulfonyl group. Examples of "alkylsulfonyl" include CH3S(O) -, - CH3CH2S(O) -, - CH3CH2CH2S(O)-, (CH3)2CHS(O)- and the various isomers of butylsulfonyl, pentasulfide and hexylaniline. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2and (CH3)2CHS(O)2different isomers butylsulfonyl, pentasulphide and hexylsilane. "Alkylamino", "dialkylamino", etc. are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "alkylsilanes" means the replacement of the alkyl on cycloalkyl group and includes, for example, ethylcyclopropane, isopropylaminomethyl, 3-methylcyclopentene and 4-methylcyclohexyl. The term "cycloalkenyl" means replacing cycloalkyl on the alkyl group. Examples of "cycloalkenyl include cyclopropylmethyl, cyclopentylmethyl and other cycloalkyl ragment, associated with unbranched or branched alkyl groups.

The term "halogen", either alone or in compound words such as "halogenated", or when used in descriptions, such as "alkyl substituted with halogen"includes fluorine, chlorine, bromine or iodine. In addition, when used in compound words such as "halogenated", or when used in descriptions, such as "alkyl substituted by halogen, the said alkyl may be partially or completely replaced by halogen atoms that can be the same or different. Examples of "halogenoalkane" or "alkyl substituted with halogen"includes F3C-, ClCH2-, CF3CH2- CF3CCl2-. The term "halogenosilanes", "halogenoalkane", "allogenicity", etc. are defined analogously to the term "halogenated". Examples of "halogenoalkane" include CF3O-, CCl3CH2O-, HCF2CH2CH2O - CF3CH2O-. Examples of "allogenicity include CCl3S-, CF3S-, CCl3CH2S - and ClCH2CH2CH2S-. Examples of "halogenatedsolvents" include CF3S(O)-, CCl3S(O)-, CF3CH2S(O)- CF3CF2S(O)-. Examples of "halogenallylacetic" include CF3S(O)2-, CCl3S(O)2-, CF3CH2S(O)2- CF3CF2S(O)2-.

"Alkylaryl" means an unbranched or OSVETLENIE alkyl group, associated with group C(=O). Examples of "alkylcarboxylic" include CH3C(=O) -, - CH3CH2CH2C(=O)- and (CH3)2CHC(=O)-. Examples of "alkoxycarbonyl" include CH3OC(=O) -, - CH3CH2OC(=O), CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)- and the various isomers of butoxy or phenoxycarbonyl.

The total number of carbon atoms in the replacement group is designated by the prefix "Ci-Cj", where i and j are numbers from 1 to 8. For example, C1-C4alkylsulfonyl designates a group from methylsulfonyl to butylsulfonyl; C2alkoxyalkyl denotes CH3OCH2; C3alkoxyalkyl means, for example, CH3CH(OCH3), CH3OCH2CH2or CH3CH2OCH2; and (C4alkoxyalkyl means different isomers of alkyl groups, substituted alkoxygroup, containing a total of four carbon atoms, examples include CH3CH2CH2OCH2and CH3CH2OCH2CH2.

When the connection is replaced by a Deputy with a subscript that indicates the number of these substituents can exceed 1, the said substituents (when their numbers exceed 1) are independently selected from the group of defined substituents, e.g. (R2)n, n is 1, 2, 3, 4 or 5. When a group contains a Deputy, who may be hydrogen, in the example R 2when specified, the Deputy is considered as hydrogen, it should be noted that this is equivalent to the fact that the specified group is unsubstituted.

The term "heterocyclic ring", "heterocycle" or "heterocyclic ring system" means a ring or ring system in which at least one atom in the ring is not carbon, for example nitrogen, oxygen or sulfur. Typically, the heterocyclic ring contains no more than 4 atoms of nitrogen, not more than 2 oxygen atoms and not more than 2 sulfur atom. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of a hydrogen on the specified carbon or nitrogen. Heterocyclic ring may be saturated, partially unsaturated or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies hückel rule, the said ring is also called the "heteroaromatic ring" or "aromatic heterocyclic ring".

The term "aromatic ring" or "aromatic ring system" denotes fully unsaturated carbocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the hückel rule is satisfied for the ring system). The term "kondensirovannie bicyclic ring system" includes a ring system, consisting of two condensed rings, in which the ring may be either saturated, partially unsaturated, or fully unsaturated. The term "condensed heterobicyclic ring system" includes a ring system consisting of two condensed rings, in which at least one atom in the ring is carbon and which may be aromatic or not aromatic, as defined above.

The term "optionally substituted" applied to the heterocyclic ring refers to groups that are unsubstituted or have at least one non-hydrogen Deputy, which does not inhibit the biological activity shown by the unsubstituted analog. Used here, the following definitions should be used, unless specified otherwise. The term "optionally substituted" is used interchangeably with the phrase "substituted or unsubstituted" or with the term "(UN)substituted." Unless otherwise specified, optionally substituted group may have a substituent at each substitutable position of the group, and each replacement is not dependent on the other.

When Q1represents 5 - or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of the formula1through any available ring carbon atom or nitrogen unless stated otherwise. Oppo is icno, when Q2or Q3represent a 5 - or 6-membered nitrogen-containing heterocycle, it may be attached through any available ring carbon atom or nitrogen unless stated otherwise.

As indicated above, Q1, Q2or Q3can be (among other things) a phenyl, optionally substituted by one or more substituents selected from the group of substituents as defined in the invention. Example phenyl, optionally substituted with one to five substituents is the ring illustrated as U-I in Appendix 1, where Rvis an R8or R9as defined in the invention for Q1, Q2or Q3and r is an integer from 0 to 5.

As indicated above, Q1, Q2or Q3can be (among other things) a 5 - or 6-membered heterocyclic ring which may be saturated or unsaturated, optionally substituted by one or more substituents selected from the group of substituents as defined in the invention. Examples of 5 - or 6-membered unsaturated aromatic heterocyclic ring, optionally substituted by one or more substituents include the rings U-2-U-61, shown in Appendix 1, where Rvis any Deputy, as defined in the invention for Q1, Q 2or Q3(i.e. R8or R9), and r is an integer from 0 to 4.

Appendix 1

It should be noted that when Q1, Q2or Q3represent a 5 - or 6-membered saturated or unsaturated non-aromatic heterocyclic ring, optionally substituted by one or more substituents selected from the group of substituents as defined in the invention for Q1, Q2or Q3one or two carbon atoms in the ring heterocycle optionally may be in the oxidized form of the carbonyl group.

Examples of 5 - or 6-membered saturated or unsaturated non-aromatic heterocyclic ring include the rings (G-1)-(G-35), as shown in Appendix 2. It should be noted that when the position of the accession of G is shown as a free group G can be attached to the remainder of the formula1through any available atom angle of the ode or nitrogen group G by replacing the hydrogen atom. To any available carbon atom or nitrogen by replacement of a hydrogen atom can be attached optional substituents.

It should be noted that when Q1, Q2or Q3include a ring selected from (G-28)-(35 G), G2selected from O, S or N. it Should be noted that when G2represents N, the nitrogen atom can complete its valence by substitution of H or substituents as defined in the invention for Q1, Q2or Q3(i.e. R8or R9).

Annex 2

As noted above, Q1can be (among other things) an 8-, 9 - or 10-membered condensed bicyclic ring system, optionally substituted by one or more substituents selected from the group of substituents as defined in the invention (i.e. R8). Examples of 8-, 9 - or 10-membered condensed bicyclic ring system, optionally substituted by one or more substituents include the rings U-81)-(U-123), shown in Appendix 3, where Rvis any Deputy, as defined in the invention for Q1(i.e. R8), and r is an integer from 0 to 4.

Annex 3

Although the groups Rvshown in formulas (U-I)-(U-123), it should be noted that they may not be present since they are optional substituents. It should be noted that when Rvattached to any atom, represents H, this is equivalent to the fact that the atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence, replaced with H, or Rv. It should be noted that when the position of the connection between (Rv)rand U are shown as free, (Rv)rcan be attached to any available carbon atom or nitrogen atom of the group U. it Should be noted that when the position of joining to the group U is shown as free, U can be attached to the residue of the formula1through any available carbon atom or nitrogen group U by replacing a hydrogen atom. It should be noted that some groups U m who should replace only less than 4 groups of R v(for example, (U-2)-(U-5), (U-7)-(U-48) and (U-52)-(U-61)).

Compounds of the present invention can exist in the form of one or more stereoisomers. Different stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Specialist, skilled in the art can appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enrichment relative to the other stereoisomer (stereoisomers) or when separated from the other stereoisomer (stereoisomers). In addition, a qualified specialist knows how to isolate, enrich and/or selectively to receive said stereoisomers. Compounds of the invention can be present as mixtures of stereoisomers, individual stereoisomers, or in optically active form.

Specialist, skilled in the art can appreciate that not all nitrogen contained in the heterocyclic ring, may formN-oxides, so as to oxidize the nitrogen oxide is required only pair; specialist, skilled in the art can determine which nitrogen atoms contained in the heterocyclic ring, may formN-oxides. Specialist, skilled in the art also understands that the tertiary amines which may form N-oxides. Methods of synthesis ofN-oxides of heterocycles and tertiary amines are well known to specialists, skilled in the art including the oxidation of heterocycles and tertiary amines with peroxynitrate, such as peracetic andm-chloroperoxybenzoic acid (MCPBA), hydrogen peroxide, alkylhydroperoxides, such as tert-butyl hydroperoxide, perborate sodium and dioxirane, such as dimethyldioxirane. These methods getN-oxides have been described in detail and discussed in the literature, see, for example: T.L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp. 748-750, S.V. Ley, Ed., Pergamon Press; M. Tišler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp. 18-20, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B.R.T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A.R. Katritzky, Ed., Academic Press; M. Tišler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, A.R. Katritzky and A.J. Boulton, Eds., Academic Press; and G.W.H. Cheeseman and E.S.G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, A.R. Katritzky and A.J. Boulton, Eds., Academic Press.

Salts of the compounds according to the invention include acid additive salts of inorganic or organic acids, such as Hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluensulfonate or valeric acid. Salts of the compounds according to the invention also include salts formed with PRS is adicheskii bases (for example, pyridine or triethylamine) or inorganic bases (e.g., hydrides, hydrobiidae or carbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group, for example when R4is alkylsulphonyl and R5represents H.

Thus, the present invention includes compounds selected from compounds of the formula1their N-oxides and salts, suitable for agricultural use.

Embodiments of the present invention, as described in the invention, include:

An implementation option 1. The compound of the formula1where R1represents a C1-C3alkyl, optionally substituted by one or more substituents independently selected from R6.

An implementation option 2. Connection options exercise 1, where R1represents a C1-C3alkyl, optionally substituted with halogen.

An implementation option 3. Connection options exercise 2, where R1represents a C1-C3alkyl, substituted with halogen.

An implementation option 4. Connection options exercise 3, where R1represents a C1-C3alkyl, substituted F.

An implementation option 5. Connection options exercise 4, where R1represents the t of a C 1-C3alkyl fully substituted F.

An implementation option 6. Connection options exercise 5, where R1is a CF3.

An implementation option 7. The compound of the formula1where each R2independently represents H, halogen, C1-C6halogenated, C1-C6halogenoalkane or-CN.

An implementation option 8. Connection options exercise 7, where each R2independently represents H, CF3, OCF3, halogen or-CN.

An implementation option 9. Connection options exercise 7, where each R2independently represents halogen or C1-C3halogenated.

An implementation option 10. The compound of the formula1where each R3independently represents H, halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, -CN or-NO2.

An implementation option 11. Connection options exercise 10, where each R3independently represents H, C1-C4alkyl, C1-C4halogenated, C3-C6cycloalkyl, C1-C4alkoxy or-CN.

An implementation option 12. Connection options exercise 11, where each R3regardless of performance, is to place a H, C1-C4alkyl or-CN.

An implementation option 13. Connection options exercise 12, where each R3represents H.

An implementation option 14. The compound of the formula1,where R4represents H, C1-C6alkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl.

An implementation option 15. Connection options exercise 14, where R4represents H.

Option exercise 16. The compound of the formula1,where R5represents H, OR10, NR11R12or Q1; or (C1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C4cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7.

Option implementation 17. Connection options the implementation of 16, where R5represents H; or C1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C4cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7.

Option exercise 18. Connection options exercise 17, where R5 represents H; or C1-C4alkyl, optionally substituted by one or more substituents independently selected from R7.

Option exercise 19. Connection options the implementation of 18, where R5represents a C1-C4alkyl, optionally substituted by one or more substituents independently selected from R7.

An implementation option 20. Connection options exercise 19, where R5represents CH2CF3.

An implementation option 21. Connection options exercise 19, where R5represents CH2-2-pyridinyl.

An implementation option 22. Connection options the implementation of 16, where R5is a OR10, NR11R12or Q1.

Option exercise 23. Connection options exercise 22, where R5represents NR11R12.

An implementation option 24. Connection options exercise 22, where R5is a Q1.

Option exercise 25. The compound of the formula1,where R6represents a halogen.

Option exercise 26. The compound of the formula1,where each R7independently represents halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C 4alkylsulfonyl, C2-C4alkylsulphonyl, C2-C4alkoxycarbonyl, C2-C5alkylaminocarbonyl, C2-C5halogenoalkanes, C2-C5halogenosilanes, C2-C5halogenlithiumcarbeniod, -NH2, -CN or-NO2; or Q2.

Option exercise 27. Connection options exercise 26, where each R7independently represents halogen, C2-C4alkoxycarbonyl, C2-C5alkylaminocarbonyl, C2-C5halogenosilanes, C2-C5halogenlithiumcarbeniod, -NH2, -CN or-NO2; or Q2.

An implementation option 28. Connection options exercise 27, where each R7independently represents halogen, C2-C5alkylaminocarbonyl, C2-C5halogenlithiumcarbeniod or Q2.

Option exercise 29. Connection variant implementation 28, where each R7independently represents halogen or Q2.

An implementation option 30. Connection options exercise 29, where each R7independently represents F, Cl or Br.

Option exercise 31. Connection options exercise of 30, where each R7is a F.

Option exercise 32. Connection options exercise 29, where each R7p is ecstasy a Q 2.

An implementation option 33. The compound of the formula1,where each R8independently represents halogen, C1-C4alkyl, C1-C4halogenated or-CN.

An implementation option 34. The compound of the formula1,where each R9represents halogen, C1-C4alkyl, C1-C4halogenated, -CN, phenyl or pyridinyl.

Option exercise 35. The compound of the formula1,where R10represents H; or C1-C6alkyl, optionally substituted by one or more Halogens.

An implementation option 36. The compound of the formula1,where R11represents H, C1-C6alkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl.

Option exercise 37. Connection options exercise 34, where R11represents H.

Option exercise 38. The compound of the formula1,where R12represents H or Q3; or (C1-C4alkyl, optionally substituted by one or more substituents independently selected from R7.

Option exercise 39. The compound of the formula1,where Q1represents phenyl, pyridinyl, thiazolyl,

each optionally substituted by one or more substituents independently selected from R8 .

An implementation option 40. The compound of the formula1,where each Q2independently represents a phenyl, pyridinyl or thiazolyl, each optionally substituted by one or more substituents independently selected from R9.

An implementation option 41. Connection options exercise 34, where each Q2independently represents a phenyl, pyridinyl or thiazolyl.

An implementation option 42. The compound of the formula1,where Q3represents phenyl, pyridinyl or thiazolyl, each optionally substituted by one or more substituents independently selected from R9.

An implementation option 43. The compound of the formula1,where each A1, A2, A3, A4, A5and A6represents CR3.

An implementation option 44. The compound of the formula1,where A1represents N; and each A2, A3, A4, A5and A6represents CR3.

Option exercise 45. The compound of the formula1,where A2represents N; and each A1, A3, A4, A5and A6represents CR3.

Option exercise 46. The compound of the formula1,where A4represents N; and each A1, A2, A3, A5and A6represents CR3.

A variant of the implementation of the population 47. The compound of the formula1,where A6represents N; and each A1, A2, A3, A4and A5represents CR3.

An implementation option 48. The compound of the formula1,where B1B2and B3independently represent CR2.

Option exercise 49. Connection options exercise 48, where B2represents CH.

An implementation option 50. The compound of the formula1,where B1represents N; and B2and B3independently represent CR2.

An implementation option 51. The compound of the formula1,where B2represents N; and B1and B3independently represent CR2.

An implementation option 52. The compound of the formula1,where B2represents CR2; and B1and B3represent N.

Option exercise 53. The compound of the formula1,where W represents O.

An implementation option 54. The compound of the formula1,where n is 0.

Embodiments of the present invention, including embodiments of 1-54 above, as well as any other embodiments of described herein may be combined in any way, and descriptions of variables in variants of implementation include not only the compounds of the formula1,but also to the initial compounds and the intermediate connection of enum. In addition, embodiments of the present invention, including embodiments of 1-54 above, as well as any other embodiments of described herein, and any combination thereof, pertain to compounds and methods of the present invention.

Combinations of embodiments 1-54 explained by the following options:

An implementation option A. a Compound of the formula1,where

R1represents a C1-C3alkyl, optionally substituted by one or more substituents independently selected from R6;

each R2independently represents H, halogen, C1-C6halogenated, C1-C6halogenoalkane or-CN; and

each R3independently represents H, halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, -CN or-NO2.

An implementation option B. the Connection options exercise of A, where

B1B2and B3independently represent CR2;

W represents O;

R4represents H, C1-C6alkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl; and

R5represents H, NRHR12or Q1; what if C 1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C4cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7.

An implementation option C. Connection option exercise B, where

R1represents a C1-C3alkyl, optionally substituted with halogen;

each R2independently represents H, CF3, OCF3, halogen or-CN;

each R3independently represents H, C1-C4alkyl, C1-C4halogenated, C3-C6cyclopropyl, C1-C4alkoxy or-CN; and

each R7independently represents halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C4alkylsulphonyl, C2-C4alkoxycarbonyl, C2-C5alkylaminocarbonyl, C2-C5halogenoalkanes, C2-C5halogenosilanes, C2-C5halogenlithiumcarbeniod, -NH2, -CN or-NO2; or Q2.

An implementation option D. the Connection option C implementation where

R4represents H;

R5the stand is made by a C 1-C4alkyl, optionally substituted by one or more substituents independently selected from R7;

each R7independently represents halogen or Q2; and

each Q2independently represents a phenyl, pyridinyl or thiazolyl.

An implementation option E. the Connection case for D, where

R1is a CF3;

every A1, A2, A3, A4, A5and A6represents CR3;

B2represents CR2; and

each R3independently represents H, C1-C4alkyl or-CN.

An implementation option F. Connection of option exercise E, where

B2represents CH;

each R2independently represents halogen or C1-C3halogenated;

R3represents H;

R5represents CH2CF3or CH2-2-pyridinyl; and

n is 0.

Specific options for implementation include compounds of the formula1selected from the group consisting of:

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-from oxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenemethylamine,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-ethyl-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-methoxyethyl)-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(2,2,2-triptorelin)-2-oxoethyl]-1-naphthaleneboronic,

5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-chinainternational,

5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-ethanolinduced and

1-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-ethanolinduced.

It should be noted that the specific embodiments of include compounds of the formula1selected from the group consisting of:

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenemethylamine,

5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-chinainternational,

5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-ethanolinduced and

1-[5-(35-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-ethanolinduced.

The following specific options for implementation include any combination of compounds of the formula1selected directly from the groups above.

Embodiments of the present invention further include:

Variant implementation of the AA. The compound of the formula1qits N-oxide or salt,

where

A1, A2, A3, A4, A5and A6independently selected from the group consisting of CR3and N, provided that at most 3 of the A1, A2, A3, A4, A5and A6represent N;

W represents O or S;

R1represents a C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R6;

each R2independently represents H, halogen, C1-C6alkyl, C1-C6halogenated, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1 -C6alkylamino, C2-C6dialkylamino, C2-C4alkoxycarbonyl, -CN or-NO2;

each R3independently represents H, halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, -CN or-NO2;

R4represents H, C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes, C4-C7cycloalkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl;

R5represents H, OR10, NR11R12or Q1; or (C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7; or

R4and R5 together with the nitrogen atom to which they are attached, form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, and the specified ring optionally substituted by 1-4 substituents, independently selected from the group consisting of C1-C2of alkyl, halogen, -CN, -NO2and C1-C2alkoxy;

each R6independently represents halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, -CN or-NO2;

each R7independently represents halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C7alkylsulphonyl, C2-C7alkoxycarbonyl, C2-C7alkylaminocarbonyl, C3-C9dialkylaminoalkyl, C2-C7halogenoalkanes, C2-C7halogenosilanes, C2-C7halogenlithiumcarbeniod, C3-C9halogenoaluminates, hydroxy, -NH2, -CN or-NO2; or Q2;

each R8independently represents the Wallpaper halogen, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, C2-C4alkoxycarbonyl, - CN or-NO2;

each R9independently represents halogen, C1-C6alkyl, C1-C6halogenated, C3-C6cycloalkyl, C3-C6halogenosilanes, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylsulfonyl, C1-C6halogenacetylenes, C1-C6alkylsulfonyl, C1-C6halogenallylacetic, C1-C6alkylamino, C2-C6dialkylamino, -CN, -NO2, phenyl or pyridinyl;

R10represents H; or C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more Halogens;

R11represents H, C1-C6alkyl, C2-C6alkenyl, C 2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes, C4-C7cycloalkyl, C2-C7alkylaryl or C2-C7alkoxycarbonyl;

R12represents H; Q3; or (C1-C6alkyl, C2-C6alkenyl, C2-C6quinil, C3-C6cycloalkyl, C4-C7alkylsilanes or C4-C7cycloalkenyl, each optionally substituted by one or more substituents independently selected from R7; or

R11and R12together with the nitrogen atom to which they are attached, form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, and the specified ring optionally substituted by 1-4 substituents, independently selected from the group consisting of C1-C2of alkyl, halogen, -CN, -NO2and C1-C2alkoxy;

Q1is a phenyl ring, a 5 - or 6-membered heterocyclic ring or an 8-, 9 - or 10-membered condensed bicyclic ring system, optionally containing one to three heteroatoms selected from not more than 1 atom of O, not more than 1 atom S and no more than 3 atoms of N, each ring or ring system optionally substituted by one or more Deputy what stitely, independently selected from R8;

each Q2independently represents a phenyl ring or a 5 - or 6-membered heterocyclic ring, each ring optionally substituted by one or more substituents independently selected from R9;

Q3is a phenyl ring or a 5 - or 6-membered heterocyclic ring, each ring optionally substituted by one or more substituents independently selected from R9; and

n equals 1, 2, 3, 4 or 5.

It should be noted that the compounds of the present invention are characterized by favorable nature of metabolism and/or profile of residual concentrations in the soil and are active, affecting a wide range of agricultural and non-agricultural invertebrate pests.

It should be noted that because of the struggle with a wide range of invertebrate pests and economic importance of protecting agricultural crops from harm or damage caused by invertebrate pests, by combating invertebrate pests represents embodiments of the invention. Compounds of the present invention, due to its excellent properties move or systemic in plants, also protects the leaf or other plant part, to the mi compound of the formula 1or the composition containing the compound, which is not directly in contact.

It should also be noted that because embodiments of the present invention is a composition containing the compound of any of the previous embodiments, as well as any other embodiments described herein, and any combination and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, the composition optionally additionally contain at least one additional biologically active compound or agent.

In addition, it should be noted that, because embodiments of the present invention is a composition for combating invertebrate pests, containing a biologically effective amount of a compound of any one of the preceding embodiments, as well as any other embodiments described herein, and any combination of them, and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, the composition optionally additionally contain biologically effective amount of at least one of the additional biologically active compound or agent. Embodiments of the invention also include methods of combating invertebrate pest comprising contacting bespozvonochnykh pest or its environment with a biologically effective amount of a compound of any of the previous embodiments (e.g., as described herein song).

Embodiments of the invention also include a composition comprising a compound of any of the previous embodiments, in the form of a liquid composition for irrigation of the soil. Embodiments of the invention further include methods of combating invertebrate pest comprising contacting the soil with a liquid composition for irrigation soil containing biologically effective amount of a compound of any of the previous embodiments.

Embodiments of the invention also include spray compositions for combating invertebrate pests, containing a biologically effective amount of a compound of any of the previous embodiments and the propellant. Embodiments of the invention additionally include a bait composition for combating invertebrate pests, containing a biologically effective amount of a compound of any of the previous embodiments, one or more nutrients, the long is the super attractant, and optionally a wetting agent. Embodiments of the invention also include a device for combating invertebrate pests containing the bait composition and body, adapted to accommodate these bait compositions, where the housing has at least one hole, the size of which allows bespozvonochnykh pest to pass through the hole, resulting in the invertebrate pest can gain access to the bait composition from a position outside the housing, where the housing is additionally adapted for placement on the site or near the site of potential or known activity bespozvonochnykh pest.

To obtain compounds of the formula1can be used one or more of the following methods and variations as described in schemes 1-12. Define R1, R2, R4, R5, A1, A2, A3, A4, A5, A6B1B2B3n and W in the compounds of formulas1-15below are listed above in the invention, unless otherwise indicated. Compounds of the formula1aand1bare subtypes of the compounds of the formula1, the compounds of the formula12a-12care subtypes of the compounds of the formula12and the compound of the formula15ais a compound of formula 15.

Compounds of the formula1a(formula1where W represents O) can be is obtained by aminocarboxylate the approach formulated above or iodides of the formula 2where X represents Br or I, a suitably substituted amino compounds of formula 3, as shown in figure 1.

This reaction is usually carried out by kilbrandon formula2where X represents Br, in the presence of palladium catalyst in the atmosphere. Palladium catalysts used in the present method, usually contain palladium in the formal oxidation state of either 0 (i.e., Pd(0)), or 2 (i.e. Pd(II)). A large variety of these containing palladium compounds and complexes are suitable as catalysts for the present method. Examples containing palladium compounds and complexes used as catalysts in the method of scheme 1 include PdCl2(PPh3)2(dichloride bis(triphenylphosphine)palladium(II), Pd(PPh3)4(tetrakis(triphenylphosphine)palladium(0)), Pd(C5H7O2)2(acetylacetonate palladium(II), Pd2(dba)3(Tris(dibenzylideneacetone)dipalladium(0)) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II). The method of scheme 1 is generally carried out in the liquid phase, and therefore greater efficiency palladium catalyst preferably should have a good solubility in the liquid phase. Used solvents include, for example, ethers, such as 1,2-dimethoxyethane, amides such as N,N-DIMET acetamid, and not halogenated aromatic hydrocarbons, such as toluene.

The method of scheme 1 can be carried out in a wide range of temperatures ranging from about 25 to about 150°C. it Should be noted that temperature of from about 60 to about 110°C typically provide high speed response and high output product. Basic methods and techniques of aminocarboxylate kilbrandon and amine are well known in the literature; see, for example, H. Honno et al., Synthesis,1989, 715; and J.J. Li, G.W. Gribble, editors, Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist,2000. The method of scheme 1 described in stage C of example 2 and stage E of example 4.

As shown in scheme 2, compounds of the formula1b(formula 1, where W represents S can be obtained by treating the corresponding amide compounds of the formula1athe reagent carrier of tigraphy, such as P2S5(see, for example, E. Klingsberg et al. J. Am. Chem. Soc.,1951, 72, 4988; E.C. Taylor Jr. et al., J. Am. Chem. Soc.,1953, 75, 1904; R. Crossley et al., J. Chem. Soc. Perkin Trans. 1,1976, 977) or reagent Lawesson (2,5-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphate-2,4-disulfide; see, for example, S. Prabhakar et al. Synthesis,1984, 829).

The method of scheme 2 can be carried out in a wide temperature range, including from about 50 to about 150°C. it Should be noted that temperature of from about 70 to about 120°C usually provide the high speed response and high output product. The method of scheme 2 described in example 3.

Compounds of the formula1acan be also obtained by combining the carboxylic acid of formula 4 with an appropriately substituted amino compounds of formula 3, as shown in figure 3.

This reaction is usually carried out in the presence of a dehydrating reagent combinations, such as dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, cyclic anhydride 1-papapostolou acid or carbonyldiimidazole, in the presence of a base, such as triethylamine, pyridine, 4-(dimethylamino)pyridine or N,N-diisopropylethylamine, in an anhydrous aprotic solvent such as dichloromethane or tetrahydrofuran, at a temperature usually between room temperature and 70°C. the Method of scheme 3 described in stage E of example 1.

Compounds of the formula4can be obtained by hydrolysis of ester of the formula5where R represents methyl or ethyl, as shown in figure 4.

In this method, the ester compound of the formula5is converted into the corresponding carboxylic acid of the formula4by standard methods known in this field. For example, the handling of complex methyl or ethyl ester of the formula5an aqueous solution of lithium hydroxide in tetrahydrofuran, followed acelerou is receiving leads to the corresponding carboxylic acid of the formula 4. The method of scheme 4 described in stage D of example 1.

Compounds of the formula5can be obtained 1,3-dipolar-cyclopentadiene styrene of the formula7to nitrilosides obtained from Asimov formula6as shown in scheme 5.

This reaction usually proceeds with the formation of in situ intermediate hydrocapillary that dehydrochlorinated to nitriloside, which is then subjected to a 1,3-dipolar to cyclopentadienyl styrene 7 with obtaining the compounds of Formula5. By the standard method gloriouse reagent, such as sodium hypochlorite, N-chlorosuccinimide or chloramine-T, together with the oxime in the presence of styrene. Depending on conditions, to facilitate the reaction of dehydrocorydaline may be necessary the presence of an amine base such as pyridine or triethylamine. The reaction can be performed in a wide variety of solvents, including tetrahydrofuran, diethyl ether, methylene chloride, dioxane and toluene, at temperatures from room temperature to the temperature of reflux distilled solvent. The basic methodology of the cycloaddition of nitrilosides to olefins is well described in the chemical literature; for example, see Lee, Synthesis,1982, 6, 508-509; Kanemasa et al., Tetrahedron,2000, 56, 1057-1064; EP 1538138-A1, and references given in this document. The method of scheme 4 described in stage C PR is a measure of 1.

Compounds of the formula2can be also obtained 1,3-dipolar-cyclopentadiene styrene of the formula7to nitrilosides obtained from Asimov formula8as shown in scheme 6.

In the method of scheme 6, compounds of formula2where X represents a halogen atom, is obtained by contacting the compounds of formula8with gloriouse reagent followed by the addition of compounds of the formula7. The method of scheme 6 can be carried out similarly to the method of scheme 5 described above. The method of scheme 6 described in stage B of example 2, stage D of example 4 and stage C of example 5.

The most widely used for the synthesis of compounds of the formula1the group styrene represented by the formula7aas shown in scheme 7. These intermediate compounds can be obtained by catalyzed by palladium combination arylboronic acids of formula 9 with commercially available 2-bromo-3,3,3-triptocaine (formula10). The basic methodology for this reaction are described in the chemical literature; see Pan et al., J. Fluorine Chemistry,1999, 95, 167-170. The method of scheme 7 described in stage B of example 1.

The oximes of the formula6can be obtained by reaction of aldehydes11with hydroxylamine, as shown in scheme 8. For example, see, H.K. Jung et al. Bioorg. Med. Chem.,2004, 12, 3965.

The aldehydes of the formula11can be obtained is a variety of ways, known in this area; some of the aldehydes are known or commercially available compounds. For example, obtaining the compounds of formula11where A1, A2, A3, A4, A5and A6represent CH and R9represents IU described P.P. Madenson et al. J. Med. Chem.,2002, 45, 5755. The method of scheme 8 described in stage a of example 1.

As shown in scheme 9, the oximes of the formula8where X represents a halogen atom, can be obtained from the corresponding aldehydes of the formula12similarly to the method of scheme 8. The method of scheme 9 is described in stage a of example 2, stage C of example 4 and stage B of example 5.

Compounds of the formula12are commercially available or known compounds or they can be obtained in a variety of ways known in this field. For example, the compound of the formula12can be obtained by direct formirovanie corresponding aryl halides, see G.E. Boswell et al. J. Org. Chem.,1995, 65, 6592; or the recovery of the corresponding complex arylation, see P.R. Bernstein et al. Bioorg. Med. Chem. Lett.,2001, 2769 and L.W. Deadfly et al. Aust. J. Chem.,1989, 42, 1029.

In the specific example, as shown in figure 10, the aldehydes of the Formula12can be obtained from the appropriate methylseleninic compounds of the formula13(where X is the tsya halogen) by reaction with N-bromosuccinimide (NBS) in the presence of 2,2'-azobis(2-methylpropionitrile) (AIBN) and sodium acetate with getting acetates of the formula 14that then is converted into the aldehydes of the formula12by esterification and oxidation. The method of scheme 10 is described in example 4, stages A and B.

Compounds of the formula13are commercially available or known compounds or they can be obtained in a variety of ways known in this field. For example, the compound of the formula13where A3represents N, A1, A2, A4, A5and A6represent CH, can be obtained as described in Molecules,2004, 9, 178.

An alternative method of producing aldehydes of the formula12(where X represents a halogen atom) is shown in scheme 11. Formyl group of the formula12can be entered into a 10-membered aromatic ring system by substitution of the bromine atom in the compound of the formula15. Links to the specified General way, see Synthesis,2006, 293 and Bioorg. Med. Chem.,2004, 12, 715. The method of scheme 11 described in stage a of example 5.

As shown in figure 12, the aldehydes of the formula12band12ccan be obtained from 5,8-dibromothiophene (formula15aby processing the compounds of formula15an-BuLi at -78°C and stopping the reaction with N,N-dimethylformamide.

The compound of the formula15acan be obtained by a method described, for example, in Synthesis,202 , 83; or by way G.E. Boswell et al. J. Org. Chem.,1995, 65, 6592. Alternatively, killdevil formula12can be obtained in various other ways known in this field, such as the restoration of the corresponding complex arylation, see references P.R. Bernstein et al. Bioorg. Med. Chem. Lett.,2001, 2769 and L.W. Deadfly et al. Aust. J. Chem.,1989, 42, 1029.

It is known that some reagents and reaction conditions described above to obtain compounds of the formula1may not be compatible with certain functional groups present in the intermediate compounds. In these cases, the inclusion in the synthesis of sequences of introducing/removing protection or mutual transformations of functional groups will contribute to obtaining the desired products. The use and choice of protective groups will be obvious to a person skilled, qualified in the field of chemical synthesis (see, for example, Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Specialist qualified in this field, it is known that in some cases, after the introduction of a given reagent specified in any individual scheme, it may require not described in detail additional standard stages of synthesis to complete the synthesis of compounds of the formula1. Specialist qualified in this area, it is also known that can potreboval is by conducting a combination of stages, described in the above schemes in an order other than from the specific sequences provided for producing compounds of the formula1.

Specialist qualified in this area, it is also known that compounds of the formula1and intermediate compounds described herein can be subjected to various electrophilic, nucleophilic, radical, ORGANOMETALLIC, oxidation and reductive reactions for the introduction of substituents or modify existing substituents.

Without additional studies have suggested that a specialist qualified in this field, using the preceding description can apply the present invention to the fullest extent possible. Thus, the examples provided below should be interpreted only as an explanatory and non-limiting description in whatever way. Spectra1H-NMR are given in ppm from tetramethylsilane; "s" means singlet, "d" means doublet, "t" means triplet, "m" means multiplet, "DD" means doublet of doublets and Sirs" means broad singlet.

EXAMPLE 1

Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic

Stage A:Obtain methyl 4-[(hydroxyimino)methyl]-1-naphthalenesulfonate

To peremeshivaemogo solution of methyl 4-formyl-1-naphthalenesulfonate (2.2 g, of 10.3 mmol) in methanol (50 ml) was added a solution of hydroxylamine (1,33 ml, 50% in water). After stirring at room temperature for 2 h the reaction mixture was concentrated under reduced pressure, obtaining mentioned in the title compound as a pale yellow solid (2.55 g).

1H-NMR (CDCl3): 8,93 (d, 1H), 8,86 (s, 1H), to 8.41 (d, 1H), 8,14 (d, 1H), 7,82 (d, 1H), 7,63 (m, 2H), was 4.02 (s, 3H).

Stage B:Obtaining 1,3-dichloro-5-[1-(trimethylgermyl)ethynyl]benzene

To a mixture of tetrahydrofuran (33 ml), 1,2-dimethoxyethane (33 ml) and 4N aqueous solution of potassium hydroxide (33 ml) in a sealed tube Fischer - porter volume of 200 ml was added 3,5-dichlorophenylamino acid (8,72 g of 45.7 mmol) and 2-bromo-3,3,3-cryptochrome (10.0 g, 57,2 mmol), followed by addition of tetrakis(triphenylphosphine)palladium(0) (264 mg, 0,229 mmol). Then the mixture was heated to 75°C for 3 hours the Reaction mixture was distributed between diethyl ether and water. The aqueous extract was washed with diethyl ether (2×20 ml). The organic extracts were combined, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the title compound as a clear oil (4,421 g).

1H-NMR (CDCl3): δ 7,41 (s, 2H), 7,33 (s, 1H), 6,04 (d, 1H), of 5.82 (d, 1H).

Stage C:The floor is giving methyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenesulfonate

To a stirred solution of methyl 4-[(hydroxyimino)methyl]-1-naphthalenesulfonate (i.e. the product of stage A) (1.0 g, 4,36 mmol) in N,N-dimethylformamide (5.0 ml) was added N-chlorosuccinimide (1,16 g, 8,72 mmol). The resulting mixture was stirred for 1.5 h at room temperature, and then was added a solution of l,3-dichloro-5-[1-(trifluoromethyl)ethynyl]benzene (i.e. the product of stage (B) (3,20 g of 13.1 mmol) and triethylamine (6,1 ml, was 43.6 mmol) in N,N-dimethylformamide (4.0 ml). After stirring for an additional 2 h at room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the title compounds as a pale yellow oil (700 mg, yield 34%).

1H-NMR (CDCl3): 8,88 (d, 1H), 8,80 (d, 1H), 8,10 (d, 1H), 7,68 (m, 2H), 7,55 (m, 3H), 7,46 (DD, 1H), 4,27 (d, 1H), a 4.03 (s, 3H), 3,91 (d, 1H).

Stage D:Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthaleneboronic acid

To a stirred solution of methyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenesulfonate (i.e. the product of stage C) (650 mg, of 1.39 mmol) in tetrahydrofuran (10 ml) dobavlyalost monohydrate of lithium hydroxide (350 mg, to 8.34 mmol) in water (10 ml)and then methanol (10 ml). The resulting mixture was allowed to mix at room temperature over night. The reaction mixture was distributed between water and diethyl ether. Then the aqueous phase was acidified using 6N aqueous solution of hydrochloric acid to pH 2 and extracted with ethyl acetate. The combined organic extracts were washed with saturated salt solution, dried and concentrated, obtaining mentioned in the title compound as a white solid (450 mg).

1H-NMR (CDCl3): the remaining 9.08 (d, 1H), 8,80 (d, 1H), 8,31 (d, 1H), 7,71 (m, 2H), EUR 7.57 (m, 3H), 7,46 (DD, 1H), 4,28 (d, 1H), 3,91 (d, 1H).

Stage E:Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic

A mixture of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthaleneboronic acid (i.e. the product of stage C) (190 mg, 0.42 mmol), 4-(dimethylamino)pyridine (77 mg, 0,63 mmol), propylphosphonic anhydride (0,38 ml, was 0.63 mmol, 50% in ethyl acetate) and 2,2,2-triptorelin (0,033 ml, 0.42 mmol) in dichloromethane (5 ml) was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product, the compounds of the present invention, in the de white solid (71 mg).

1H-NMR (CDCl3): 8,78 (d, 1H), 8,18 (d, 1H), 7,63 (m, 2H), 7,56 (m, 2H), 7,52 (d, 1H), 7,46 (m, 1H), 7,44 (d, 1H), 6,41 (t, 1H), 4,23 (d, 1H), 4,20(m,2H), a 3.87 (d, 1H).

EXAMPLE 2

Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic

Stage A:Getting 4-bromo-1-naphthalenemethylamine

To a stirred solution of 4-bromo-1-naphthalenemethylamine (3.7 g, 15.7 mmol) in ethanol (30 ml) was added an aqueous solution of hydroxylamine (1.25 ml, 50% in water). After stirring at room temperature for 3 h the reaction mixture was concentrated under reduced pressure, obtaining mentioned in the title compound as a pale yellow solid (3.8 g).

1H-NMR (DMSO-d6): 11,60 (s, 1H), 8,81 (s, 1H), 8,71 (d, 1H), 8,24 (d, 1H), 7,95 (d, 1H), 7,74 (m, 3H).

Stage B:Obtaining 3-(4-bromo-1-naphthalenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazol

To a stirred solution of 4-bromo-1-naphthalenemethylamine (i.e. the product of stage A) (2,33 g, 9.3 mmol) in N,N-dimethylformamide (6.0 ml) was added N-chlorosuccinimide (1.70 g, 12.7 mmol). The reaction mixture was stirred for 1 h at room temperature, and then was added a solution of 1,3-dichloro-5-[1-(trifluoromethyl)ethynyl]benzene (i.e. the product of stage B of example 1) (2.70 g, and 11.2 mmol) and triethylamine (4.5 ml, of 32.0 mmol) in N,N-dimethylformamide (9.0 ml). After AC is shivani for an additional 2 h at room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the title compound as a white solid (2.9 g, yield 64%).

1H-NMR (CDCl3): 8,87 (m, 1H), 8,32 (m, 1H), to 7.77 (d, 1H), 7,66 (m, 2H), 7,55 (s, 2H), 7,46 (DD, 1H), 7,32 (d, 1H), 4,24 (d, 1H), 3,88 (d, 3H).

Stage C:Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic

A mixture of 3-(4-bromo-1-naphthalenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazol (i.e. the product of stage (B) (1.0 g, 2.04 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0,22 g, 0.30 mmol), 2-(aminomethyl)pyridine (0,86 g of 7.96 mmol) and triethylamine (5.6 ml, 40 mmol) in toluene (15 ml) was purged with carbon monoxide for 15 minutes. Then, using a cylinder into the reaction vessel supported the carbon monoxide concentration. The reaction mixture was stirred at 70°C in an atmosphere of carbon monoxide during the night. The mixture was cooled to room temperature, filtered through a thin layer of hard-shelled filter nozzles Celite® and washed with a small amount of ethyl acetate. The filtrate was concentrated and the residue was purified column x is matography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product, the compounds of the present invention, in the form of a white solid (0,72 g, yield 65%).

1H-NMR (CDCl3): 8,81 (d, 1H), 8,55 (d, 1H), scored 8.38 (d, 1H), 7,80-7,27 (m, 10H), 4,89 (d, 2H), 4,22 (d, 1H), 3,86 (d, 1H).

EXAMPLE 3

Getting 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenemethylamine

A mixture of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic (i.e. the product of example 2) (40 mg, 0,073 mmol) and 2,5-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphate-2,4-disulfide (reagent Lawesson) (18 mg, 0,044 mmol) in toluene (2 ml) was heated at the boiling point under reflux for 2 hours, the Reaction mixture was cooled to room temperature and directly purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product, the compounds of the present invention, in the form of a yellow solid (29 mg, 71%yield).

1H-NMR (CDCl3): 9,41 (Sirs 1H), 8,91 (DD, 1H), 8,70 (DD, 1H), 8,46 (d, 1H), 8,21 (d, 1H), of 7.75 (dt, 1H), to 7.64 (d, 1H), EUR 7.57 (s, 2H), 7,47 (DD, 1H), 7,43 (t, 1H), 7,38 (d, 1H), 7,24 (DD, 1H), 5,14 (d, 2H), and 4.68 (d, 1H), 4,39 (d, 1H).

EXAMPLE 4

Obtain 5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridi ylmethyl)-8-chinainternational

Stage A:Obtaining (8-bromo-5-chinoline)acetate

A mixture of 8-bromo-5-methylinosine (5,4 g of 24.3 mmol), N-bromosuccinimide (5,2 g, 29.2 mmol) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (0.40 g, a 24.3 mmol) in carbon tetrachloride (80 ml) was heated at the boiling point under reflux for 3 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature and filtered using hexane for washing. The filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (50 ml)and then was added sodium acetate (4.0 g, 48.8 mmol). The resulting mixture was stirred at 100°C for 2 h in nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with water and was extracted with a mixture of ethyl acetate and hexane (3:7). The organic layer was washed with saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product as a pale yellow solid (4.8 g).

Stage B:Obtain 8-bromo-5-chinainternational

A mixture of 8-bromo-5-chinoline)acetate (i.e. the product of stage A) and methanol (50 ml) was heated at boiling point with reverse holodilniki for 1 h in the presence of trace amounts of potassium carbonate (10 mg). Then the reaction mixture was cooled to room temperature and concentrated under reduced pressure, obtaining the corresponding alcohol with a quantitative yield as a pale yellow solid.

To a stirred solution of the crude alcohol (2.0 g, 8.3 mmol) in dichloromethane (60 ml) was slowly added 1,1,1-Tris(acetoxy)-1,1-dihydro-1,2-benzodioxol-3(1H)-he (periodinane dessa-Martin) (4.0 g, 9.4 mmol) at room temperature. After stirring for 0.5 h the reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate and saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product as a white solid (1.8 g).

1H-NMR (CDCl3): 10,31 (s, 1H), 9,65 (DD, 1H), 9,12 (DD, 1H), compared to 8.26 (d, 1H), 7,88 (d, 1H), 7,66 (DD, 1H).

Stage C:Obtain 8-bromo-5-hyalinobatrachium

To a stirred solution of 8-bromo-5-chinainternational (i.e. the product of stage (B) (1.7 g, 7.1 mmol) in ethanol (30 ml) was added an aqueous solution of hydroxylamine(0.7 ml, 50% in water). After stirring at room temperature for 2 h the reaction mixture was concentrated under decreased the pressure, getting listed in the title compound as a pale yellow solid (1.8 g).

1H-NMR (DMSO-d6): of 11.61 (s, 1H), 9,16 (DD, 1H), 9,07 (DD, 1H), 8,79 (s, 1H), to 8.20 (d, 1H), 7,79 (d, 1H), 7,72 (DD, 1H).

Stage D:Obtain 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]quinoline

To a stirred solution of 8-bromo-5-hyalinobatrachium (i.e. the product of stage C) (1.7 g, 6.8 mmol) in N,N-dimethylformamide (13,0 ml) was added N-chlorosuccinimide (1.24 g, 9.3 mmol). The reaction mixture was stirred for 1 h at room temperature, and then was added a solution of 1,3-dichloro-5-[1-(trifluoromethyl)ethynyl]benzene (i.e. the product of example 1, stage B) (1,96 g, 8.1 mmol) and triethylamine (2,86 ml of 20.4 mmol) in N,N-dimethylformamide (7.0 ml). After stirring for an additional 12 h at room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the title compound as a white solid (2.0 g, yield 61%).

1H-NMR (CDCl3): 9,39 (DD, 1H), remaining 9.08 (DD, 1H), with 8.05 (d, 1H), to 7.59 (DD, 1H), 7,55 (s, 2H), 7,44 (t, 1H), 7,40 (d, 1H), 4,27 (d, 1H), 3,92 (d, 1H).

One hundred is s E :Obtain 5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-chinainternational

A mixture of 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]quinoline (i.e. the product of stage D) (500 mg, 1.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (75 mg, 0.10 mmol), 2-(aminomethyl)pyridine (of 0.43 ml, 4.0 mmol) and triethylamine (2.8 ml, 20 mmol) in toluene (10 ml) was purged with carbon monoxide for 15 minutes. Then, using the balloon, the reaction flask was supported by the carbon monoxide concentration. The reaction mixture was stirred at 70°C in an atmosphere of carbon monoxide during the night. The mixture was cooled to room temperature, filtered through a thin layer of hard-shelled filter nozzles Celite® and washed with a small amount of ethyl acetate. The filtrate was concentrated and the residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product, the compounds of the present invention, in the form of a brown foam solid (60 mg, yield 11%).

1H-NMR (CDCl3): 12,02 (Sirs 1H), 9,52 (d, 1H), 9,01 (s, 1H), 8,88 (d, 1H), to 8.62 (d, 1H), 7,60-7,74 (m, 3H), 7,56 (s, 2H), 7,45 (Sirs 2H), 7,20 (DD, 1H), 4,96 (d, 2H), 4,32 (d, 1H), 3,98 (d, 1H).

EXAMPLE 5

Obtain 5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxa is alil]-N-(2-pyridinylmethyl)-8-ethanolinduced

Stage A: Obtain 8-bromo-5-ethanolinduced and 5-bromo-8-ethanolinduced

To stir a mixture of 5,8-dibromothiophene (4.0 g, a 13.9 mmol) in tetrahydrofuran (120 ml) at -78°C under nitrogen atmosphere was added dropwise a solution ofn-utility (2,3 M in hexane, 7.3 ml, is 16.8 mmol). The reaction mixture darkened. After stirring for 15 minutes the reaction mixture was suppressed by the addition of N,N-dimethylformamide (4.0 ml). After stirring at 78°C for additional 1 h, the reaction mixture was extinguished with water, was extracted with a mixture of ethyl acetate/hexane (2:8), washed with water and saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate to obtain 8-bromo-5-ethanolinduced (0.10 g), and then 5-bromo-8-ethanolinduced (1.0 g) as white solids.

1H-NMR (CDCl3) 8-bromo-5-ethanolinduced: 10,36 (s, 1H), 9,72 (s, 1H), 9,00 (d, 1H), 8,79 (d, 1H), 8,04 (d, 1H), 8,01 (DD, 1H); and

1H-NMR (CDCl3) 5-bromo-8-ethanolinduced: 10,57 (s, 1H), 10,41 (s, 1H), 8,81 (d, 1H), 8,18 (d, 1H), 8,11 (d, 1H), 7,94 (d, 1H).

Stage B: Obtain 8-bromo-5-thinlinesxangasite.html

To a stirred solution of 8-bromo-5-ethanolinduced (i.e. the product of the study is (A) (75 mg, 0.3 mmol) in ethanol (7 ml) was added an aqueous solution of hydroxylamine (0.5 ml, 50% in water). After stirring at room temperature overnight the reaction mixture was concentrated under reduced pressure, obtaining mentioned in the title compound as a yellow solid (70 mg).

1H-NMR (DMSO-d6): of 11.75 (s, 1H), of 9.55 (s, 1H), 8,78 (s, 1H), 8,71 (d, 1H), 8,59 (d, 1H), 8,07 (d, 1H), of 7.96 (d, 1H).

Stage C:Obtain 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]isoquinoline

To a stirred solution of 8-bromo-5-thinlinesxangasite.html (i.e. the product of stage B) (70 mg, 0.28 mmol) in N,N-dimethylformamide (2.0 ml) was added N-chlorosuccinimide (64 g, 0.48 mmol). The reaction mixture was stirred for 0.5 h at room temperature, and then was added a solution of 1,3-dichloro-5-[1-(trifluoromethyl)ethynyl]benzene (135 mg, 0,56 mmol) (i.e. the product of example 1, stage B) and triethylamine (of 0.12 ml, 0.86 mmol) in N,N-dimethylformamide (1.5 ml). After stirring for an additional 12 h at room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated salt solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to receive the receiving specified in the title compound (20 mg), contaminated with a small amount of impurities.

Stage D:Obtain 5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-ethanolinduced

A mixture of 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]of isoquinoline (i.e. the product of stage C) (20 mg, 0.04 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (6 mg, 0,008 mmol), 2-(aminomethyl)pyridine (17 mg, 0.16 mmol) and triethylamine (0.1 ml, 0.7 mmol) in toluene (2 ml) was purged with carbon monoxide for 15 minutes. Then, using the balloon, the reaction flask was supported by the carbon monoxide concentration. The reaction mixture was stirred at 70°C in an atmosphere of carbon monoxide during the night. The mixture was cooled to room temperature, filtered through a thin layer of hard-shelled filter nozzles Celite® and washed with a small amount of ethyl acetate. The filtrate was concentrated and the residue was purified column chromatography on silica gel, using as eluent a mixture of hexane/ethyl acetate, to obtain specified in the header of the product, the compounds of the present invention, in the form of a pale white solid (15 mg).

1H-NMR (CDCl3): 9,77 (s, 1H), 8,80 (d, 1H), to 8.70 (d, 1H), charged 8.52 (s, 1H), 7,81-of 7.23(m,9H), 4,88 (d, 2H), 4,28 (d, 1H), 3,92 (d, 1H).

In accordance with the methods described herein and by methods known is suspended in the level of technology, can be obtained the following compounds of tables 1-9. In the tables below the following abbreviations are used: CN means cyano, Ph means phenyl, Py means pyridinyl, Me means methyl, Et means ethyl, andi-Pr means isopropyl.

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

Table 8

Table 9

Composition/Application

Compounds of the present invention typically will be used in the form of a composition with a suitable carrier containing at least one component selected from a liquid diluent, a solid diluent or a surfactant. The recipe or the ingredients of the composition are selected so as to be compatible with the physical properties of the active component, method of application and environmental factors such as soil type, moisture and temperature. Used songs include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including the friends of the microemulsion and/or suspoemulsions) and the like, which optionally may be condensed in the gels. Used compositions also include solids, such as dusty, powders, granules, briquettes, tablets, films (including seed coating), and the like, which may be dispersible in water ("wet") or soluble in water. The active ingredient may be (micro)encapsulated, and then introduced into the suspension or solid composition; alternatively, the composition of the active ingredient can be completely encapsulated or covered with a coating"). Encapsulation can adjust or delay the release of the active ingredient. Sprayable composition can be carried in a suitable environment and be used in amounts of from about one to several hundred liters per hectare. Concentrated compositions are used primarily as intermediates in obtaining subsequent compositions.

The compositions typically contain an effective amount of the active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.

Mass percentage
Active ingredient the ThinnerSurface-active substance
Dispersible and water-soluble granules, tablets and powders0,001-900-99,9990-15
Suspensions, emulsions, solutions (including emulsifiable concentrates)1-5040-990-50
Dusty1-2570-990-5
Pellets and briquettesof 0.001-995-99,9990-15
Concentrated compositions90-990-100-2

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. In McCutcheon''s Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, and Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964 lists surfactants and recommended uses. All the compositions may contain the substance of minor amounts of additives, reduce foam, caking, corrosion, microbiological growth, and the like, or thickening agents that increase the viscosity.

Surfactants include, for example, polyethoxysiloxane alcohols, polyethoxysiloxane ALKYLPHENOLS, polyethoxysiloxane esters sorbitan and fatty acids, diallylmalonate, alkyl sulphates, alkylbenzenesulfonate, organosilicone, N,N-dialkylamide, ligninsulfonate, condensation products of naphthalenesulfonate and formaldehyde, polycarboxylate, esters of glycerin, block copolymers of polyoxyethylene/polyoxypropylene and alkylpolyglycoside, where the number of units of glucose, called the degree of polymerization (D.P.), may vary from 1 to 3, and the chain length of alkyl chains can vary from6to C14(see Pure and Applied Chemistry 72, 1255-1264). Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silicon dioxide, talc, hard-shelled land, urea, calcium carbonate, sodium carbonate and sodium bicarbonate and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethylsulfoxide, N-alkylpyridine, ethylene glycol, polypropyleneglycol, propylene carbonate, dibasic esters, paraffins, alkyl benzenes, alkylnaphthalene, glycerin, triacetin (triacetyluridine), is Lugovoe, castor, linseed, Tung, Kungaeva, corn, peanut, cottonseed, soybean, rapeseed and coconut oils, esters of fatty acids, ketones, such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone; acetates, such as exilerated, heptylate and octylated, and alcohols, such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol.

Used compositions of the present invention may also contain substances known to the experts, qualified in this field, as, for example, excipients such as defoamers, film-forming agents and dyes. Defoamers may include dispersible in water liquid containing polyorganosiloxanes, such as Rhodorsil® 416. The binders may include polyvinyl acetate, polyvinyl acetate copolymers, copolymer of polyvinylpyrrolidone and vinyl acetate, polyvinyl alcohols, copolymers of polyvinyl alcohol and wax. The dyes may include dispersible in water liquid coloring compositions, such as red dye Pro-lzed®. Specialist, skilled in this field can appreciate that this is not an exhaustive list of excipients. Suitable examples of excipients include listed here and listed in McCutcheon's 2001, Volume 2: Functional Materials, published nom MC Publishing Company, and in PCT WO 03/024222.

Solutions, including emulsifiable concentrates, can be obtained by simple mixing of the ingredients. Dusty and powders can be obtained by mixing and grinding in a hammer mill or water mill. Suspensions are usually obtained by grinding in the wet state; see, for example, U.S. 3060084. Pellets and briquettes can be obtained by spraying the active substance onto a pre-obtained granular carriers or by agglomeration. Cm. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48, Perry's Chemical Engineer''s Handbook, 4thEd., McGraw-Hill, New York, 1963, pages 8-57 and forth, and WO 91/13546. The briquettes can be obtained as described in U.S. 4172714. Dispersible in water and soluble granules can be obtained as described in U.S. 4144050, U.S. 3920442 and DE 3246493. Tablets can be obtained, as described in U.S. 5180587, U.S. 5232701 and U.S. 5208030. Film can be obtained, as described in GB 2095558 and U.S. 3299566.

More detailed information relative to prior art compositions can be found in T.S. Woods, "The Formulator''s Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience , The Food-Environment Challenge, T. Brooks and T.R. Roberts, Eds., Proceedings of the 9thInternational Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. Cm. also U.S. 3235361, Col. 6, line 16 through Col.7, line 19 and Examples 10-41; U.S. 3309192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2891855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

In the following examples, all percentages are given in mass relations and all compositions obtained by standard methods. Complex numbers refer to compounds in index tables A-C. Without further research it is assumed that a specialist qualified in this field, using the preceding description can utilize the present invention to the fullest extent possible. Thus, the following examples should be regarded as merely explanatory and not limiting the present description, by whatever way. The percentages given in mass relations, except in those cases where expressly indicated otherwise.

An example of a
Wettable powder
Connection 165,0%
polietilenglikolya ether dodecylphenol2,0%
ligninsulfonate sodium4,0%
alumosilicate 6,0%
montmorillonite (calcinated)23,0%
The example In
Granules
Connection 210,0%
granules attapulgite (low-volatile material of 0.71/0.30 mm; U.S.S. sieve No. 25-50)90,0%
Example With
Extruded briquettes
Compound 825,0%
anhydrous sodium sulfate10,0%
untreated ligninsulfonate calcium5,0%
alkylnaphthalene sodium1,0%
calcium-magnesium bentonite59,0%
Example D
Emulsifiable concentrate
Connection 2 20,0%
the mixture is soluble in the oil sulfonates and polyoxyethylene ethers10,0%
isophorone70,0%
Example E
The microemulsion
Connection 215,0%
copolymer of vinylpyrrolidone-vinyl acetate30,0%
alkylpolyglycoside30,0%
glycerylmonostearate15,0%
water20,0%
Example F
Seed treatment
Connection 10120,00%
copolymer of vinylpyrrolidone-vinyl acetateto 5.00%
lignite acidic wax5,0%
ligninsulfonate calcium 1,00%
block copolymers of polyoxyethylene/polyoxypropylene1,00%
stearyl alcohol (POE 20)2,00%
polyorganosiloxane0,20%
red dye0,05%
water65,75%
Example G
Fertilizer sticks
Connection 2012,50%
copolymers of pyrrolidone-styrene4,80%
cristianini 16-ethoxylate2,30%
talc0,80%
corn starchto 5.00%
cause a slow fertilizer Nitrophoska® Permanent 15-9-15 (BASF)to 36.00%
kaolin38,00%
wateror 10.60%

Compounds of this is bretania are active against a wide range of invertebrate pests. These pests include invertebrates inhabiting diverse environments, such as, for example, foliage plants, roots, soil, harvested crops or other food products, building, or to the outer skin of animals. These pests include, for example, invertebrates, feeding on foliage (including leaves, stems, flowers and fruits, seeds, wood, textile fibers and blood or tissues of animals, and cause, thus, harm or damage, for example, growing or stored crops, forests, greenhouse crops, ornamental plants, seedlings, stored food products, or fibrous materials, or buildings or other structures or their contents, or are harmful to animal health or human health. Professionals skilled in this field will appreciate that not all compounds are equally effective against all stages of growth all pests.

These present compounds and compositions, thus, applicable in agriculture to protect crops from phytophagous invertebrate pests, as well as in non-agricultural purposes to protect other horticultural crops and plants against phytophagous invertebrate pests. The specified application is before the protection of agricultural crops and other plants (i.e. both agricultural and non-agricultural), which contain the genetic material introduced by genetic engineering methods (i.e. transgenic plants), or modified by mutagenesis in order to obtain favorable characteristics. Examples of these characteristics include resistance to herbicides, resistance to herbivorous pests (e.g. insects, ticks, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria and viruses), improved plant growth, increased tolerance to adverse growing conditions, such as high or low temperatures, low or high soil moisture and high salinity, increased flowering or fruiting, increased productivity, accelerated maturation, higher quality and/or nutritional value of the harvested product, or improved storage properties or recycling of collected products. Transgenic plants can be modified for expression of multiple traits. Examples of plants containing signs provided by genetic engineering or by mutagenesis, include varieties of corn, cotton, soybeans and potatoes expressing insecticidal toxinBacillus thuringiensissuch as YIELD GARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, and herbicide-tolerant varieties of corn, cotton, soybeans and canola, such as ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® the CLEARFIELD®, and culture, expressing N-acetyltransferase (GAT)to provide resistance to the herbicide glyphosate, or culture containing HRA gene, which provides resistance to herbicides inhibiting acetolactate (ALS). These compounds and compositions can synergistically interact with signs of introduced genetic engineering or modified by mutagenesis, increasing, thus, the phenotypic expression or performance characteristics or increasing the efficiency of these compounds and compositions in combating invertebrate pests. In particular, the present compounds and compositions can synergistically interact with the phenotypic expression of proteins or other natural products, toxic to invertebrate pests, which provides more than additive, the effectiveness of the fight against these pests.

Non-agricultural applications relate to combating invertebrate pests in fields other than field crops. Non-agricultural applications of these compounds and compositions include combating invertebrate pests in stored grains, beans and other food products, and textiles, such as clothing and carpets. Non-agricultural applications of these compounds and compositions is s also include combating invertebrate pests on ornamental plants, in forests, in gardens, along roadsides and railway lines alienation, as well as on the turf, such as lawns, Golf courses and pastures. Non-agricultural applications of these compounds and compositions also include combating invertebrate pests in homes and other buildings that can be occupied by people and/or their domesticated animals, for example, with farms, ranches, zoos or other animals. Non-agricultural applications of these compounds and compositions also include the control of pests, such as termites, which can damage the wood or other building materials used in buildings.

Non-agricultural applications of these compounds and compositions also include the protection of human and animal health by combating invertebrate pests, which are parasites or vectors of infectious diseases. Combating parasites of animals includes control external parasites that parasitize on the body surface of an animal host (e.g., on the shoulders, armpits, abdomen, inner thighs), and internal parasites that parasitize inside the body of an animal host (e.g., stomach, intestines, lungs, veins under the skin, lymphatic tissue). External parasites or pests that transmit over the alavanja, include, for example, ticks-trombiculids, ticks, lice, mosquitoes, flies, ticks and fleas. Internal parasites include divisie, nematodes and worms. Compounds and compositions of the present invention are suitable for systemic and/or non-systemic control of infestation or infection by parasites in animals. Compounds and compositions of the present invention is particularly suited to control external parasites or pests that transmit disease. Compounds and compositions of the present invention are suitable for combating parasites that invaziruyut agricultural working animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, Buffalo, rabbits, chickens, turkeys, ducks, geese and bees; domestic animals such as dogs, cats, household birds and aquarium fish; and so-called experimental animals such as hamsters, Guinea pigs, rats and mice. In the fight against these parasites can reduce the loss and deterioration of health (meat, milk, wool, skins, eggs, honey etc), thus, the use of a composition containing the compound of the present invention provides a more economical and easy farming.

Examples of agricultural or non-agricultural invertebrate pests include eggs, larvae and adults of troop Lepdoptera, such as scoops, podgryzayuschie scoops, the geometrid moths and heliothine family Noctuidae (e.g., pink borers (Sesamia inferensWalker), corn borers (Sesamia nonagrioidesLefebvre), scoop the South (Spodoptera eridaniaCramer), scoop grass (Spodoptera fugiperdaJ.E. Smith), beet scoop (Spodoptera exiguaHübner), cotton bollworm (Spodoptera littoralisBoisduval), gallopalooza scoop (Spodoptera ornithogalliGuenee), black podgryzayuschie scoop (Agrotis ipsilonHufnagel), caterpillar velvet bean (Anticarsia gemmatalisHübner), green moth (Lithophane antennataWalker), cabbage scoop (Barathra brassicaeLinnaeus), soybean moth (Pseudoplusia includensWalker, Metallofizika gray (Trichoplusia niHübner), tobacco moth (Heliothis virescensFabricius)); svalilsya, czechanski, butterflies, building spider nests, cone butterflies, mermaidy and pests, skeletonema leaves from the family Pyralidae (e.g., corn borer (Ostrinia nubilalisHübner), caterpillars damaging scars citrus (Amyelois transitellaWalker), butterflies of liquidation (Crambus caliginosellusClemens), meadow moths (Pyralidae:Crambinae), such as meadow moth (Herpetogramma licarsisalisWalker), borers of sugarcane (Chilo infuscatellusSnellen), small tomato borers (Neoleucinodes elegantalisGuenee), green moth (Cnaphalocerusmedinalis), grape moth (Desmia funeralisHübner), melon caterpillar (Diaphania nitidalisStoll), Ognevka cabbage (Heluala hydralis Guenee), rice stem Ognevka (Scirpophaga incertulasWalker), borers early shoots (Scirpophaga infuscatellusSnellen), white rice Ognevka (Scirpophaga innotataWalker), borers top shoots (Scirpophaga nivellaFabricius), teknokroma rice Ognevka (Chilo polychrysusMeyrick), cabbage (Crocidolomia binotalisEnglish)); leafrollers, leafrollers pockety, moth and caterpillar pests of the fruit of the family Tortricidae (e.g., Codling moth (Cydia pomonellaLinnaeus), grape moth (Endopiza viteanaClemens), tortrix Oriental peach (Grapholita molestaBusck), citrus false mol wild Apple (Cryptophlebia leucotretaMeyrick), citrus scoop (Ecdytolopha aurantianaLima), Krasnopolsky moth (Argyrotaenia velutinanaWalker), wavy moth (Choristoneura rosaceanaHarris), light brown Apple moth (Epiphyas postvittanaWalker), the European grape moth (Eupoecilia ambiguellaHübner), vertuga Bud (Pandemis pyrusanaKearfott), an omnivorous species (Platynota stultanaWalsingham), the species of krivosha within (Pandemis cerasanaHübner), the species of krivosha willow (Pandemis heparanaDenis &Schiffermüller)); and many other economically important Lepidoptera (e.g., the cabbage moth (Plutella xylostellaLinnaeus), pink cotton worm (Pectinophora gossypiellaSaunders), Gypsy moth (Lymanthria disparLinnaeus), peach moth (Carposina niponensisWalsingham), moth Urumova (Anarsia lineatellaZellr), mol potato tuber (Phthorimaea operculellaZeller), mol-pestryanka fruit neinastran (Lithocolletis blancardellaFabricius), Asian Apple mol-pestryanka (Lithocolletis ringoniellaMatsumura), rice moth (Lerodea eufalaEdwards), mol group hawthorn (Leucoptera scitellaZeller)); eggs, nymphs and adults of troop Blattodea including cockroaches families Blattellidae and Blattidae (e.g., cockroach black (Blatta orientalisLinnaeus), Asian cockroach (Blatella asahinaiMizukubo), cockroach red (Blatella germanicaLinnaeus), cockroach striped (Supella longipalpaFabricius), American cockroach (Periplaneta americanaLinnaeus), brown cockroach (Periplaneta brunneaBurmeister), Madeira cockroach (Leucophaea maderaeFabricius), brown cockroach (Periplaneta fuliginosaService), Australian cockroach (Periplaneta australasiaeFabr.), cockroach grey (Nauphoeta cinereaOlivier and smooth cockroach (Symploce pallensStephens)); eggs, larvae feeding on leaves, fruits, roots, seeds and vesicular tissue and adults of the order of Coleoptera including weevils families Anthribidae, Bruchidae, and Curculionidae (e.g., the weevil cotton (Anthonomus grandisBoheman), rice weevil water (Lissorhoptrus oryzophilusKuschel), granary weevil (Sitophilus granariusLinnaeus), rice weevil (Sitophilus oryzaeLinnaeus), the weevil of annual bluegrass (Listronotus maculicollisDietz), bluegrass weevil (Sphenophorus parvulusGyllenhal), prowling the weevil (Sphenophorus venatusvestitu), Denver weevil (Sphenophorus cicatristriatusFahraeus)); excavation flea beetle, potato flea beetle, koreeda, leaf beetles, Colorado potato beetles and leaf beetles of the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa decemlineataSay), leaf-corneil (Diabrotica virgiferavirgiferaLeConte)); Khrushchev and other beetles of the family Scarabaeidae (e.g., garden chafer Japanese (Popillia japonicaNewman), garden chafer Eastern (Anomala orientalisWaterhouse,Exomala orientalis(Waterhouse) Baraud), North garden chafer (Cyclocephala borealisArrow), southern garden chafer (Cyclocephala immaculataOlivier orC.luridaBland), beetle-the beetle and the cockchafer (Aphodius), black beetle (Ataenius spretulusHaldeman), beetle brilliant green (Cotinis nitidaLinnaeus), garden chafer Asian garden (Maladera castaneaArrow cockchafer (Phyllophagaand ordinary beetle (Rhizotrogus majalisRazoumowsky)); koreeda family Dermestidae; wireworms family Elateridae; beetles of the family Scolytidae and flour worms of the family Tenebrionidae. In addition, agricultural and non-agricultural pests include: eggs, adults and larvae of detachment Dermaptera including earwigs family Forficulidae (e.g., haverty common (Forficula auriculariaLinnaeus), haverty black (Chelisoches morioFabricius)); eggs, immature individuals, adults and nymphs of the order Hemiptera and Homoptera such as bugs-kanaky family Miridae, cicadas family Cicadidae, cycatki (e.g. species ofEmpoascafamilies Cicadellidae, ostalnye bugs (for example, Cimex lectulariusLinnaeus) family Cimicidae, delphacidae families Fulgoroidae and Delphacidae, the humpback family Membracidae, listblock family Psyllidae, whiteflies family Aleyrodidae, aphids of the family Aphididae, phylloxera family Phylloxeridae, scale insects of the family Pseudococcidae, scales of the families Coccidae, Diaspididae and Margarodidae, bugs-lace-family Tingidae, bugs-defenders of the family Pentatomidae, bugs turtles (e.g., wheat bug-bugBlissus leucopterus hirtusMontandon) and the southern bug-bug (Blissus insularisBarber)and other fruit bugs of the family Lygaeidae, pennisi family Cercopidae, pumpkin bugs of the family Coreidae and krasnolipe family Pyrrhocoridae. Also included eggs, larvae, nymphs and adults of troop Acari (mites)such as spider clasic and red mites in the family Tetranychidae (e.g., the spider Klasik (Panonychus ulmiKoch), clasic spider bimaculated (Tetranychus urticaeKoch), clasic Macdaniel (Tetranychus mcdanieliMcGregor)), flat mites in the family Tenuipalpidae (e.g., clasic citrus flat (Brevipalpus lewisiMcGregor)), rust and Bud mites in the family Eriophyidae and other eating the leaves ticks and mites that are harmful to human and animal health, for example dust mites in the family Epidermoptidae, zeleznici family Demodicidae, grain mites in the family Glycyphagidae, ticks squad Ixodidae (e.g., deer tick (Ixodes scapularisSay), Australian paralyzing mite (Ixodes holocyclusNeumann), Ixodes who bream variable ( Dermacentor variabilisSay), mite American (Amblyomma americanumLinnaeus)) and horse mites and scabies mites of the families Psoroptidae, Pyemotidae, and Sarcoptidae; eggs, adults and immature specimens of Orthoptera order, including locusts, cicadas and crickets (e.g., locusts (for example,Melanoplus sanguinipesFabricius,M. differentialisThomas), American locust (for example,Schistocerca americanaDrury), desert locust (Schistocerca gregariaForskal), migratory locust (Locusta migratoriaLinnaeus), Bush locust (Zonocerus), house cricket (Acheta domesticusLinnaeus), mole crickets (e.g., brown mole cricket (Scapteriscus vicinusScudder) and the southern mole cricket (Scapteriscus borelliiGiglio-Tos)); adult and immature individuals detachment Diptera, including flies-miners (e.g. species ofLiriomyzasuch as tomato leaf miner (Liriomyza sativaeBlanchard)), small Diptera, Drosophila (Tephritidae), flies Swedish (for example,Oscinella fritLinnaeus)living in the soil maggots, house flies (e.g.,Musca domesticaLinnaeus), sourceloc home (for example,Fannia canicularisLinnaeus,F. femoralisStein), gigalos autumn (for example,Stomoxys calcitransLinnaeus), flies ordinary field, gigalos cow small, padalnyh flies (e.g. species ofChrysomyathe speciesPhormiaand other mehoopany flying pests, flies (e.g., species ofTabanus), horseflies (e.g. species ofGastrophilusthe speciesOestrus), larvae bullish striped gadfly (e.g. species of ), deer flies (e.g., species ofChrysops), runza sheep (for example,Melophagus ovinusLinnaeus) and other Brachycera, mosquitoes (e.g., species ofAedesthe speciesAnophelesthe speciesCulex), midges (e.g. species ofProsimuliumthe speciesSimulium), grapes, midges, the species of the family sciaridae and other Nematocera; eggs, adults and immature individuals detachment Thysanoptera, including tobacco thrips (Thrips tabaciLindeman) and other eating the leaves thrips; insect pests of the order Hymenoptera including ants (e.g., Florida ant-bark beetles (Camponotus floridanusBuckley), red ant-bark beetles (Camponotus ferrugineusFabricius), the ant-tree-borer, Pennsylvania (Camponotus pennsylvanicusDe Geer), home ant (Technomyrmex albipesfr. Smith), large-headed ants (speciesPheidole), ants-cast (Tapinoma melanocephalumFabricius); Pharaoh ant (Monomorium pharaonisLinnaeus), fire ant small (Wasmannia auropunctataRoger), ant Richter (Solenopsis geminateFabricius), red ant Richter (Solenopsis invictaBuren), Argentine ant (Iridomyrmex humilisMayr), paratrechina (Paratrechina longicornisLatreille), ant sod (Tetramorium caespitumLinnaeus), corn ant (Lasius alienusFörster) and homemade ant (Tapinoma sessileSay)). Other Hymenoptera include bees (including bee-carpenter), hornets, these wasps, social wasps and real sawflies (Neodiprion; speciesCephus); insect pests of the detachment Isoptera, including termites this is Istv Termitidae (for example, the speciesMacrotermes,Odontotermes obesusRambur), Kalotermitidae (for example,Cryptotermesand Rhinotermitidae (for example,Reticulitermesthe speciesCoptotermes,Heterotermes tenuisHagen), including termite yellow-footed (Reticulitermes flavipesKollar), Western termite (Reticulitermes hesperusBanks), Taiwan subterranean termite (Coptotermes formosanusShiraki), Indian wood termite (Incisitermes immigransSnyder), termite-dravograd (CryptotermesbrevisWalker), drywood termite (Incisitermes snyderiLight), South-Eastern subterranean termite (Reticulitermes virginicusBanks), Western termite (Incisitermes minorHagen, wood termites, such as species ofNasutitermesand other termites of economic importance; insect pests of the detachment Thysanura such as casulity (Lepisma saccharinaLinnaeus) and casulity home (Thermobia domesticaPackard); insect pests of the detachment Mallophaga, including head lice (Pediculus humanus capitisDe Geer), body louse (Pediculus humanusLinnaeus), Phaedo (Menacanthus stramineusNitzsch), flashed dog (Trichodectes canisDe Geer), pogoed chicken petrorhagia (Goniocotes gallinaeDe Geer), sheep lice (Bovicola ovisSchrank), lice cow Korotkevich (Haematopinus eurysternusNitzsch), lice cow dolgonos (Linognathus vituliLinnaeus) and other sucking and biting parasites that attack man and animals; insect pests of the detachment Siphonoptera including the Oriental rat flea (Xenopsylla cheopisRothschild), cat flea (Ctenocehalides felis Bouche), dog flea (Ctenocephalides canisCurtis), flea chicken (Ceratophyllus gallinaeSchrank), flea suction (Echidnophaga gallinaceaWestwood), human flea (Pulex irritansLinnaeus) and other fleas that infect mammals and birds. Other arthropods pests include spider squad Araenae, such as the brown recluse spider (Loxosceles reclusaGertsch &Mulaik) and the black widow spider (Latrodectus mactansFabricius), and millipedes squad Scutigeromorpha, such as Flycatcher common (Scutigera coleoptrataLinnaeus). Compounds of the present invention also have an effect on the members of the class Nematoda, Cestoda, Trematoda and Acanthocephala, including economically important members of groups Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida, such as, without limitation, economically important agricultural pests (e.g. nematodes root growths of the genusMeloidogynedamaging nematodes of the genusPratylenchus, root nematodes of the genusTrichodorusetc) and pests of human and animal health (for example, all of the economically important species of trematodes, tapeworms and roundworms, such asStrongylus vulgarisin horses,Toxocara canisin dogs,At contortusin sheep,Dirofilaria immitisin dogs,Anoplocephala perfoliatain horses,Fasciola hepaticaLinnaeus from ruminant and so on).

Compounds in accordance with the present invention show particularly high activity against pests of Lepidoptera (e.g. the measures, Alabama argillaceaHübner (caterpillar shovels cotton American),Archips argyrospilaWalker (tortrix),A. rosanaLinnaeus (European species) and other species ofArchips,Chilo suppressalisWalker (Ognevka),Cnaphalocrosis medinalisGuenee (rice moth),Crambus caliginosellusClemens (Ognevka),Crambus teterrellusZincken (caterpillar bluegrass),Cydia pomonellaLinnaeus (Codling moth),Earias insulanaBoisduval (cotton bollworm),Earias vittellaFabricius (cotton bollworm spotted),Helicoverpa armigeraHübner (American bollworm),Helicoverpa zeaBoddie (cotton bollworm),Heliothis virescensFabricius (scoop tobacco),Herpetogramma licarsisalisWalker (the beet webworm),Lobesia botranaDenis &Schiffermüller (moth vine),Pectinophora gossypiellaSaunders (pink cotton worm),Phyllocnistis citrellaStainton (citrus fly-miner),Pieris brassicaeLinnaeus (large butterflies),Pieris rapaeLinnaeus (small butterflies),Plutella xylostellaLinnaeus (cabbage moth),Spodoptera exiguaHübner (beet scoop),Spodoptera lituraFabricius (tobacco bollworm, caterpillar devouring inflorescences),Spodoptera frugiperdaJ.E. Smith (autumn scoop),Trichoplusia niHübner (Metallofizika grey) andTuta absolutaMeyrick (tomato fly-miner)).

Compounds of the invention also exhibit significant activity against members of the order Homoptera including:Acyrthisiphon pisumHarris (pea aphid),Aphis craccivoraKoch (black aphids alfalfa),Aphis fabaeScopoli (bean aphid),Aphis gossypiiGlover (cotton aphid, melon is aphid), Aphis pomiDe Geer (aphid Codling),Aphis spiraecolaPatch (aphid Tamagawa),Aulacorthum solaniKaltenbach (aphid vonkova),Chaetosiphon fragaefoliiCockerell (strawberry aphid),Diuraphis noxiaKurdjumov/Mordvilko (wheat aphid Russian),Dysaphis plantagineaPaaserini (aphid pink),Eriosoma lanigerumHausmann (aphid blood leaf),Hyalopterus pruniGeoffroy (aphids, mealy plum),Lipaphis erysimiKaltenbach (aphid lookupentry),Metopolophium dirrhodumWalker (cereal aphid),Macrosipum euphorbidaeThomas (potato aphid leaf),Myzus persicaeSulzer (potato aphid peach, peach aphid green),Nasonovia ribisnigriMosley (aphid latalowa), a species ofPemphigus(root aphids and gallarraga aphid),Rhopalosiphum maidisFitch (aphid corn leaf),Rhopalosiphum padiLinnaeus (aphid Osawa),Schizaphis graminumRondani (cereal aphid common),Sitobion avenaeFabricius (cereal aphid),Therioaphis maculataBuckton (aphid spotted alfalfa),Toxoptera aurantiiBoyer de Fonscolombe (tea aphid) andToxoptera citricidaKirkaldy (citrus aphid); speciesAdelges(heresy);Phylloxera devastatrixPergande (phylloxera Hickory);Bemisia tabaciGennadius (tobacco whitefly),Bemisia argentifoliiBellows & Perrig (whiteflies),Dialeurodes citriAshmead (citrus whitefly andTrialeurodes vaporariorumWestwood (greenhouse whitefly);Empoasca fabaeHarris (Cicada potato),Laodelphax striatellusFallen (small brown Cicada),Macrolestes quadrilineatusForbes (Cicada Asteraceae),Nephotettix cinticepsUhler (Cicada green),Nephotettix nigropictusStål (lcadc the rice), Nilaparvata lugensStål (Cicada brown),Peregrinus maidisAshmead (Cicada corn),Sogatella furciferaHorvath (Cicada short-tailed),Sogatodes orizicolaMuir (delphacidae rice),Typhlocyba pomariaMcAtee (Cicada leaf), a species ofErythroneoura(cycatki grape);Magicidada septendecimLinnaeus (Cicada);Icerya purchasiMaskell (mealybug Australian grooved),Quadraspidiotus perniciosusComstock (San Jose scale);Planococcus citriRisso (mealybug grape powdery); speciesPseudococcus(other bugs);Cacopsylla pyricolaFoerster (medenica pear),Trioza diospyriAshmead (listblock Jurmala).

Compounds of the present invention also show activity against members of the order Hemiptera including:Acrosternum hilareSay (green bug-activist),Anasa tristisDe Green (pumpkin bug),Blissus leucopterusleucopterusSay (bug-bug),Cimex lectulariusLinnaeus (bed bug),Corythuca gossypiiFabricius (cotton bug),Cyrtopeltis modestaDistant (tomato bug),Dysdercus suturellusHerrich-Schäffer (Krasnogo cotton),Euchistus servusSay (brown bug-activist),Euchistus variolariusPalisot de Beauvois (spotted bug-activist), species ofGraptosthetus(some kinds of bugs),Leptoglossus corculusSay (bug-crevic pine),Lygus lineolarisPalisot de Beauvois (klopik meadow),Nezara viridulaLinnaeus (bug cotton gardening),Oebalus pugnaxFabricius (bug-activist rice),Oncopeltus fasciatusDallas (big bug Euphorbiaceae),Pseudatomoscelis seriatusReuter (blaska cotton). Other groups Nasik is activated, with whom can fight compounds in accordance with this invention include Thysanoptera (e.g.,Frankliniella occidentalisPergande (trips wheat),Scirthothrips citriMoulton (citrus thrips),Sericothrips variabilisBeach trips soy) andThrips tabaciLindeman (thrips); and the order Coleoptera (e.g.,Leptinotarsa decemlineataSay (Colorado potato beetle),Epilachna varivestisMulsant (beetle Mexican bean) and wireworms of the genusAgriotes,AthousorLimonius).

It should be noted that some modern classification systems placed Homoptera as a suborder within the order Hemiptera.

It should be noted the use of compounds of the present invention to combat the whitefly magnoliaceae (Bemisia argentifolii). It should be noted the use of compounds of the present invention to combat wheat thrips (Frankliniella occidentalis). It should be noted the use of compounds of the present invention to combat potato leafhopper (Empoasca fabae). It should be noted the use of compounds of the present invention to combat leafhopper corn (Peregrinus maidis). It should be noted the use of compounds of the present invention to combat the cotton-melon aphid (Aphis gossypii). It should be noted the use of compounds of the present invention to combat potato peach aphids (Myzus persicae). It should be noted the use of compounds of the present invention to Bor who would Diamondback moth ( Plutella xylostella). It should be noted the use of compounds of the present invention to combat the autumn worm moth (Spodoptera frugiperda).

Compounds of the present invention can also be mixed with one or more biologically active compounds or agents including insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, growth regulators such as rooting stimulants, chemosterilants, polychemical, repellents, attractants, pheromones, stimulants nutrition, other biologically active compounds or entomopathogenic bacteria, virus or fungi, obtaining multi-component pesticide with a wider range of applications in agriculture. Thus, the present invention also relates to a composition comprising a biologically effective amount of a compound of the formula1its N-oxide or salt, and an effective amount of at least one additional biologically active compound or agent and can further comprise at least one component selected from a surfactant, a solid diluent or a liquid diluent. The composition can be introduced other biologically active compounds or agents containing at least one component selected from surfactants, the solid or liquid diluent. To obtain mixtures of the present invention in a composition together with the compounds of the present invention, including the compounds of formula1may be introduced for other biologically active compounds or agents with getting premix, or other biologically active compounds or agents can be introduced into the composition separately from the compounds of the present invention, including the compounds of formula1while these two songs joined together before use (for example, in the spray tank) or, alternatively, applied consistently.

Other biologically active compounds or agents used in the compositions of the present invention, can be selected from agents for combating invertebrate pests with different mode of action or chemical compounds of a different class: modulators of sodium channels, cholinesterase inhibitors, neonicotinoids, insecticidal macrocyclic lactones, blockers of GABA (γ-aminobutyric acid)-regulated chloride channels, chitin synthesis inhibitors, juvenile hormone mimetics and ligands of the receptor of octopamine, agonists ecdysone, ligand receptor ryanodine analogs nereistoxin, inhibitors of the mitochondrial transport of electrons, inhibitors of the biosynthesis of lipids, cyclodienes Ann is Chitigov, the molting inhibitors and biological agents, including nucleopolyhedrovirus (NPV), the representative of theBacillus thuringiensisencapsulated Delta endotoxinBacillus thuringiensisand naturally occurring or genetically modified viral insecticide.

It should be noted composition of the present invention, in which at least one additional biologically active compound or agent selected from insecticides of the group consisting of modulators of sodium channels, cholinesterase inhibitors, neonicotinoids, insecticidal macrocyclic lactones, GABA-regulated blockers of chloride channels, chitin synthesis inhibitors, juvenile hormone mimetics and ligands of these receptors octopamine, agonists ecdysone, ligand receptor ryanodine analogs nereistoxin, inhibitors of the mitochondrial transport of electrons, inhibitors of the biosynthesis of lipids, cyclodiene insecticides, molting inhibitors and biological agents, including nucleopolyhedrovirus, the representative of theBacillus thuringiensisencapsulated Delta endotoxinBacillus thuringiensisand naturally occurring or genetically modified viral insecticide.

In particular, it should be noted additional biologically active compounds or agents selected from insecticides of the group consisting of modulators NAT is yevich channels, cholinesterase inhibitors, neonicotinoids, insecticidal macrocyclic lactones, GABA-regulated blockers of chloride channels, chitin synthesis inhibitors, juvenile hormone mimetics and ligands of the receptor of octopamine, agonists ecdysone, ligand receptor ryanodine analogs nereistoxin, inhibitors of the mitochondrial transport of electrons, inhibitors of the biosynthesis of lipids, cyclodiene insecticides, nucleopolyhedrovirus; representativeBacillus thuringiensisencapsulated Delta endotoxinBacillus thuringiensisand naturally occurring or genetically modified viral insecticide.

It should also be noted additional biologically active compounds or agents selected from insecticides of the group consisting of pyrethroids, carbamates, neonicotinoids, blockers of neuronal sodium channels, insecticidal macrocyclic lactones, antagonists, γ-aminobutyric acid, insecticidal ureas and juvenile hormone mimetics, representative of Bacillus thuringiensis Delta-endotoxin of Bacillus thuringiensis and naturally occurring or genetically modified viral insecticide.

Examples of such biologically active compounds or agents that can be introduced into the composition together with the compounds of the present invention are: insecticides such to the to the abamectin, Arafat, acetamiprid, acetarsol, midflame (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, bistriflate, carbofuran, cartap, chlorfenapyr, chlorfluazuron, chlorantraniliprole (DPX-E2Y45), chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, titlemedium, cyfluthrin, beta-cyfluthrin, cigalotrin, gamma cigalotrin, lambda cigalotrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoat, dinotefuran, giovanola, emamectin, endosulfan, esfenvalerate, amiprol, fanatical, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, Tau-fluvalinate, lufenuron (UR-50701), flufenoxuron, fonofos, halogenated, hexaflumuron, hydramethylnon, Imidacloprid, indoxacarb, isofenphos, lufenuron, Malathion, metaflumizone, metaldehyde, metamidophos, methidathion, methomyl, methoprene, Methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, Fort, fozalon, phosmet, phosphamidon, pirimicarb, profenofos, perflutren, protrudent, pymetrozine, perflubron, pyrethrin, pyridalyl, pyriphlegethon, periphral, pyriproxifen, rotenon, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos, teba is genozid, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosulfat-sodium, toppenberg, tralomethrin, triazamate, trichlorfon and triflumuron; fungicides, such as acibenzolar, Aldemar, amisulbrom, azaconazole, AZOXYSTROBIN, benalaxyl, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, binomial, biphenyl, bitertanol, blasticidin-S, Bordeaux liquid (rejonowy copper sulphate), boscalid/nicobifen, bromuconazole, bupirimate, butiaba, carboxin, cropropamide, captafol, Captan, carbendazim, chloroneb, CHLOROTHALONIL, chlozolinate, clotrimazole, copper oxychloride salts of copper, such as copper sulfate and copper hydroxide, cyazofamid, leflunomid, having cymoxanil, tsyprokonazolu, cyprodinil, dichlofluanid, diclocil, declomycin, dicloran, dietphenterm, difenoconazol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinocap, disastrous, dithianon, dodemont, Dodin, econazole, itaconate, diferidos, epoxiconazol, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, paneramic, fanforum, fenhexamid, phenoxyl, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, perforated, verison, fluazinam, fludyoksonil flamethower, fluopicolide, fluoxastrobin, fluquinconazole, flusilazole, glucolipid, flutolanil, flutriafol, folpet, Foz the Teal-aluminum, fuberidazole, parallaxis, parameter, hexaconazole, hymexazol, guazatine, imazalil, kabekona, iminoctadine, iodice, ipconazole, iprobenfos, iprodion, iprovalicarb, isoconazole, isoprothiolane, kasugamycin, kresoxim-methyl, MANCOZEB, mandipropamid, MANEB, mepanipyrim, mefenoxam, mepronil, metalaxyl, metconazole, metasurfaces, metiram, metamyosyn/phenominalrose, mepanipyrim, metrafenone, miconazole, myclobutanil, neo-Asotin (metanational iron(III)), nuarimol, Actelion, operas, orysastrobin, oxadixyl, oxolinic acid, Expocentr, oxycarboxin, paclobutrazol, penconazole, pencycuron, pentopia, perforated, phosphonic acid, phtalic, picobenzide, picoxystrobin, polyoxin, provenzal, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazol, propineb, proquinazid, prothioconazole, pyraclostrobin, triazophos, pirivenas, Pyrimethanil, pyrrolnitrin, pyroquilon, henansal, jenoxifen, hintzen, silthiofam, simionato, spiroxamine, streptomycin, sulfur, tebuconazole, terasen, telital, tecnazene, tetraconazole, thiabendazol, leflunomid, tiopinac, thiophanate-methyl, thiram, tadini, tolclofos-methyl, tolyfluanid, triadimefon, triadimenol triarmor, triazoxide, tridemorph, trimorphic tricyclazole, Trifloxystrobin, triforine, triticonazole, uniconazole, validamycin, VI is klonolin, zineb, Zir and zoxamide; nematicides, such as aldicarb, initiates, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides, such as amitraz, chinomethionat, Chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents, including entomopathogenic bacteria such asBacillus thuringiensissubspecies aizawai,Bacillus thuringiensissubspecies kurstaki, and the encapsulated Delta-endotoxinsBacillus thuringiensis(e.g., Cellcap, MPV, MPVII); entomopathogenic fungi, such as green stone fungus; and entomopathogenic virus including baculovirus, nucleopolyhedrovirus (NPV)such as nucleopolyhedrovirusHelicoverp zea(HzNPV), nucleopolyhedrovirusAnagrapha falcifera(AfNPV); and virus granulata (GV)such as virus granulesCydia pomonella(CpGV).

Compounds and compositions of the present invention can be applied to plants genetically transformed to Express proteins toxic to invertebrate pests (such as Delta-endotoxinsBacillus thuringiensis). The effect achieved in combating invertebrate pests in the exogenous application of compounds in accordance with the present invention, may be synergistic with downregulation of protein-toxins.

General references to the decree which by agricultural pesticides (i.e. insecticides, fungicides, nematicides, acaricides, herbicides and biological agents) include:The Pesticide Manual, 13ththEdition, C.D.S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003 andThe BioPesticide Manual, 2ndEdition, L.G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001.

It should be noted composition of the present invention, in which at least one additional biologically active compound or agent selected from the group comprising: abamectin, Arafat, acetamiprid, acetarsol, aldicarb, midflame, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistriflate, buprofezin, carbofuran, cartap, chinomethionat, chlorfenapyr, chlorfluazuron, chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, Chlorobenzilate, chromafenozide, clothianidin, titlemedium, cyfluthrin, beta-cyfluthrin, cigalotrin, gamma cigalotrin, lambda cigalotrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dicofol, dieldrin, dienochlor, diflubenzuron, dimefluthrin, dimethoat, dinotefuran, giovanola, emamectin, endosulfan, esfenvalerate, ethiprole, etoxazole, fenamiphos, fenazaquin, fenbutatin oxide, fanatical, fenoxycarb, fenpropathrin, fenpyroximate, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, Tau-fluvalinate, lufenuron, flufenoxuron, fonofos, halogenated, hexaflumuron, g is citizens, hydramethylnon, initiates, Imidacloprid, indoxacarb, isofenphos, lufenuron, Malathion, metaflumizone, metaldehyde, metamidophos, methidathion, methomyl, methoprene, Methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, Fort, fozalon, phosmet, phosphamidon, pirimicarb, profenofos, perflutren, propargite, protrudent, pymetrozine, perflubron, pyrethrin, pyridaben, pyridalyl, pyriphlegethon, periphral, pyriproxifen, rotenon, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosulfat-sodium, toppenberg, tralomethrin, triazamate, trichlorfon, triflumuron,Bacillus thuringiensissubspeciesaizawai,Bacillus thuringiensissubspecieskurstakinucleopolyhedrovirus encapsulated Delta endotoxinBacillus thuringiensis, baculovirus, and entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

Also of note is a composition of the present invention, in which at least one additional biologically active compound or agent selected from the group including abamectin, acetamiprid, amitraz, avermectin, azadirachtin, bifenthrin, buprofezin, cartap chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin, cigalotrin, lambda cigalotrin, cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, giovanola, emamectin, endosulfan, esfenvalerate, ethiprole, fanatical, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, Imidacloprid, indoxacarb, lufenuron, metaflumizone, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxifen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid, thiamethoxam, thiodicarb, thiosulfat-sodium, tralomethrin, triazamate, triflumuron,Bacillus thuringiensissubspeciesaizawai,Bacillus thuringiensissubspecieskurstakinucleopolyhedrovirus and the encapsulated Delta endotoxinBacillus thuringiensis.

Options for implementation, which uses one or more of these various additives to the mixture, the ratio of the mass of these various additives to the mixture (calculated on the total weight) to the compound of the formula1typically ranges from about 1:3000 and about 3000:1. It should be noted mass relations from about 1:300 and about 300:1 (for example, the relationship from approximately 1:30 to about 30:1). Specialist qualified in this field, m the can with a simple experiment is easy to identify biologically effective amount of active ingredient needed for the desired spectrum of biological activity. It will be obvious that including these additional components, it is possible to expand the range of invertebrate pests, which are not included in the range of invertebrate pests, which allows you to fight the compound of the formula1in its purest form.

In some cases, combinations of the compounds of the present invention with other biologically active (especially in combating invertebrate pests) compounds or agents (i.e. active ingredients) can lead to more than just additive (i.e. synergistic) effect. Reducing the amount of active ingredient released into the environment, ensuring effective pest control is always desirable. When the synergy of active ingredients in combating invertebrate pests appears at the dosage of providing satisfactory for agriculture levels of combating invertebrate pests, such combinations may be advantageous in order to reduce the cost of crop production and reduce the impact on the environment.

It should be noted the combination of the compounds of formula1at least one other active ingredient for combating invertebrate pests. In particular, it should be noted this combination is s, where another active ingredient for combating invertebrate pests has a mechanism of action different from the mechanism of action of the compounds of formula1. In some cases, a combination of at least one other active ingredient for combating invertebrate pests, having a similar spectrum of activity, but a different mechanism of action will be particularly advantageous to combat the development of resistance. Thus, the composition of the present invention may further comprise a biologically effective amount of at least one additional active ingredient for combating invertebrate pests, having a similar spectrum of activity, but a different mechanism of action. The contacting of plants genetically modified for expression of the connection to protect against invertebrate pests (e.g., protein)or the provisions of the plant with a biologically effective amount of compounds of the present invention may also provide a wider range of protection of plants and is beneficial to combat the development of resistance.

In table a lists specific combinations of compounds of the formula1with other agents for combating invertebrate pests, which are examples of the mixtures, compositions and methods of the present invention. In the first column of the table And n is precisley specific agents for combating invertebrate pests (for example, "Abamectin" in the first line). In the second column of the table shows the mode of action (if known) or chemical class agent for combating invertebrate pests. In the third column of the table And the option(s) ranges of mass ratios for dosages in which the agent for combating invertebrate pests can be used in correlation with the compound of the formula1its N-oxide or a salt (for example, "50:1-1:50" abamectin relative to the compounds of formula1by weight). Thus, for example, the first row of the table And specifically describes what can be used a combination of compounds of the formula1with abamectin in a mass ratio of 50:1-1:50. The remaining rows of table A should be considered in a similar way. In addition, the table shows the specific combinations of compounds of the formula1with other agents for combating invertebrate pests, which are examples of the mixtures, compositions and methods of the present invention, and includes additional embodiments of the ranges of mass ratios for dosages.

Table A
Agent for combating invertebrate pestsThe mode of action or chemical class Conventional mass ratio
The abamectinmacrocyclic lactonefrom 50:1 to 1:50
Acetamipridthe neonicotinoidfrom 150:1 to 1:200
Amitrazthe receptor ligand of octopaminefrom 200:1 to 1:100
Avermectinmacrocyclic lactonefrom 50:1 to 1:50
Azadirachtinagonist ecdysonefrom 100:1 to 1:120
Beta-cyfluthrinthe modulator of sodium channelfrom 150:1 to 1:200
Bifenthrinthe modulator of sodium channelfrom 100:1 to 1:10
Buprofezininhibitor of chitin synthesisfrom 500:1 to 1:50
Cartapsimilar nereistoxinfrom 100:1 to 1:200
Chlorantraniliprolethe League is d receptor ryanodine from 100:1 to 1:120
Chlorfenapyrinhibitor of mitochondrial transport of electronsfrom 300:1 to 1:200
The chlorpyrifosthe cholinesterase inhibitorfrom 500:1 to 1:200
Clothianidinthe neonicotinoidfrom 100:1 to 1:400
Cyfluthrinthe modulator of sodium channelfrom 150:1 to 1:200
Cigalotrinthe modulator of sodium channelfrom 150:1 to 1:200
Cypermethrinthe modulator of sodium channelfrom 150:1 to 1:200
Cyromazineinhibitor of chitin synthesisfrom 400:1 to 1:50
Deltamethrinthe modulator of sodium channelfrom 50:1 to 1:400
Dieldrincyclodiene insecticidefrom 200:1 to 1:100
Dinotefuranthe neonicotinoidfrom 150:1 to 1:200
Giovanolathe molting inhibitorfrom 150:1 to 1:200
Emamectinmacrocyclic lactonefrom 50:1 to 1:10
Endosulfancyclodiene insecticidefrom 200:1 to 1:100
Esfenvaleratethe modulator of sodium channelfrom 100:1 to 1:400
Amiprolblocker of GABA-regulated chloride channelsfrom 200:1 to 1:100
Fanaticalfrom 150:1 to 1:200
Fenoxycarbmimetic juvenile hormonefrom 500:1 to 1:100
Fenvaleratethe modulator of sodium channelfrom 150:1 to 1:200
Fipronilblocker of GABA-regulated chloride channels from 150:1 to 1:100
Flonicamidfrom 200:1 to 1:100
Flubendiamideligand receptor ryanodinefrom 100:1 to 1:120
Flufenoksuroninhibitor of chitin synthesisfrom 200:1 to 1:100
Hexaflumuroninhibitor of chitin synthesisfrom 300:1 to 1:50
Hydramethylnoninhibitor of mitochondrial transport of electronsfrom 150:1 to 1:250
Imidaclopridthe neonicotinoidfrom 1000:1 to 1:1000
Indoxacarbthe modulator of sodium channelfrom 200:1 to 1:50
Lambda cigalotrinthe modulator of sodium channelfrom 50:1 to 1:250
Lufenuroninhibitor of chitin synthesisfrom 500:1 to 1:250
Metaflumizone from 200:1 to 1:200
Methomylthe cholinesterase inhibitorfrom 500:1 to 1:100
Methoprenemimetic juvenile hormonefrom 500:1 to 1:100
Methoxyfenozideagonist ecdysonefrom 50:1 to 1:50
Nitenpyramthe neonicotinoidfrom 150:1 to 1:200
Netizenthe neonicotinoidfrom 150:1 to 1:200
novaluroninhibitor of chitin synthesisfrom 500:1 to 1:150
Oxamylthe cholinesterase inhibitorfrom 200:1 to 1:200
Pymetrozinefrom 200:1 to 1:100
Pyrethrinthe modulator of sodium channelfrom 100:1 to 1:10
Pyridabeninhibitor of mitochondrial transport is elektronov from 200:1 to 1:100
Pyridalylfrom 200:1 to 1:100
Pyriproxifenmimetic juvenile hormonefrom 500:1 to 1:100
Ryanodineligand receptor ryanodinefrom 100:1 to 1:120
Spinetorammacrocyclic lactonefrom 150:1 to 1:100
Spinosadmacrocyclic lactonefrom 500:1 to 1:10
Spirodiclofenthe inhibitor of the biosynthesis of lipidsfrom 200:1 to 1:200
Spiromesifenthe inhibitor of the biosynthesis of lipidsfrom 200:1 to 1:200
Tebufenozideagonist ecdysonefrom 500:1 to 1:250
Thiaclopridthe neonicotinoidfrom 100:1 to 1:200
Thiamethoxamneonate OID from 1250:1 to 1:1000
Thiodicarbthe cholinesterase inhibitorfrom 500:1 to 1:400
Thiosulfat-sodiumfrom 150:1 to 1:100
Tralomethrinthe modulator of sodium channelfrom 150:1 to 1:200
Triazamatethe cholinesterase inhibitorfrom 250:1 to 1:100
Triflumuroninhibitor of chitin synthesisfrom 200:1 to 1:100
Bacillus thuringiensisbiological agentfrom 50:1 to 1:10
Delta-endotoxinBacillus thuringiensisbiological agentfrom 50:1 to 1:10
NPV (e.g., Gemstar)biological agentfrom 50:1 to 1:10

One of the options for the implementation of agents for combating invertebrate pests (e.g., insecticides and acaricides for mixing with compounds of this izopet the deposits includes modulators of sodium channels, such as bifenthrin, cypermethrin, cigalotrin, lambda cigalotrin, cyfluthrin, beta-cyfluthrin, deltamethrin, dimefluthrin, esfenvalerate, fenvalerate, indoxacarb, metofluthrin, perflutren, pyrethrin and tralomethrin; cholinesterase inhibitors such as chlorpyrifos, methomyl, oxamyl, thiodicarb and triazamate; neonicotinoids such as acetamiprid, clothianidin, dinotefuran, Imidacloprid, nitenpyram, nithiazine, thiacloprid and thiamethoxam; insecticidal macrocyclic lactones such as spinetoram, spinosad, abamectin, avermectin and emamectin; blockers of GABA (γ-aminobutyric acid)-regulated chloride channels, such as endosulfan, ethiprole and fipronil; chitin synthesis inhibitors, such as buprofezin, cyromazine, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron and triflumuron; juvenile hormone mimetics, such as giovenale, fenoxycarb, methoprene and pyriproxyfen; the ligands of these receptors octopamine, such as amitraz; agonists ecdysone, such as azadirachtin, methoxyfenozide and tebufenozide; ligands of receptors ryanodine, such as ryanodine, Anthranilic diamides, such as chlorantraniliprole (see U.S. patent 6747047, PCT publication WO 2003/015518 and WO 2004/067528) and flubendiamide (see U.S. patent 6603044); analogues of nereistoxin, such as cartap; inhibitors of the mitochondrial transport of electrons, such as chlorfenapyr the R, hydramethylnon, pyridaben; inhibitors of the biosynthesis of lipids, such as spirodiclofen and spiromesifen; cyclodiene insecticides, such as dieldrin; titlemotion; fanatical; flonicamid; metaflumizone; perflubron; pyridalyl; peridial; pymetrozine; spirotetramat and thiosulfat-sodium. One of the options for the implementation of biological agents for mixing with compounds of the present invention includes nucleopolyhedrovirus, such as HzNPV and AfNPV;Bacillus thuringiensisand the encapsulated Delta-endotoxinsBacillus thuringiensissuch as Cellcap, MPV and MPVII; and existing in nature and genetically modified viral insecticides, including members of the familyBaculoviridaeand entomopathogenic fungi. It should be noted composition of the present invention, in which at least one additional biologically active compound or agent selected from agents for combating invertebrate pests listed in the table above. Also of note is a composition of the present invention, in which at least one additional biologically active compound or agent selected from the group including cypermethrin, cigalotrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fanatical, methomyl, oxamyl, thiodicarb, acetamiprid, clothianidin, Imidacloprid, thiamethoxam, TIA is lopid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, giovanola, pyriproxifen, pymetrozine, amitraz,Bacillus thuringiensis aisawai,Bacillus thuringiensis kurstakiDelta-endotoxinBacillus thuringiensisand entomopathogenic fungi.

The mass ratio of the compounds, including the compound of the formula1its N-oxide or salt, and an additional agent for combating invertebrate pests typically range from 1000:1 to 1:1000, in one embodiment, the implementation of from 500:1 to 1:500, in another embodiment, from 250:1 to 1:200 and more in one of the embodiments from 100:1 to 1:50.

In table B below are embodiments of specific compositions comprising a compound of the formula1(compound numbers refer to compounds in index tables A-C) and an additional agent for combating invertebrate pests.

In particular the compounds listed in table B, the compound of the formula1usually combined with another agent for combating invertebrate pests in the ratios specified in table A.

Fighting invertebrates BP the parents in agricultural and non-agricultural purposes shall be implemented by processing one or more compounds of the present invention, usually in the form of the composition, the biologically effective quantity of the habitat of the pests, including the agronomic and/or Reaganomics situation of the infection, the area that you want to protect, or directly to the pests that you must fight.

Thus, the present invention includes a method of combating invertebrate pests in agricultural and/or non-agricultural purposes, including contacting bespozvonochnykh pest or its environment with a biologically effective amount of one or more compounds of the invention, or a composition comprising at least one such compound or composition comprising at least one such compound and a biologically effective amount of at least one additional biologically active compound or agent. Examples of suitable compositions containing the compound of the invention and a biologically effective amount of at least one additional biologically active compound or agent, include granular composition, where the additional active compound is present in the same granule as the compound of the invention, or granules, separate from the pellets of the compounds of the invention.

In order to achieve contact with the compound or composition of the image is the shadow to protect field crops from invertebrate pests the compound or composition is usually treated seeds of culture before planting, foliage (e.g., leaves, stems, flowers, fruit) crops or the soil or other growth medium before or after planting crops.

One of the variants of the method of contact includes sputtering. Alternatively, the granulated composition comprising a compound of the invention may be applied to the foliage of plants or to the soil. Compounds of the present invention can also effectively be delivered through the absorption plant, the compositions containing the compound of the present invention, the contacting plants with a specified composition is introduced into the soil in the form of liquid compositions by impregnation of the soil, in the form of a granular composition, by processing boxes with seedlings or by dipping of seedlings. It should be noted composition of the present invention in the form of a liquid composition for impregnation of the soil. Also of note is the way of combating invertebrate pests comprising contacting bespozvonochnykh pest or its environment with a biologically effective amount of compounds of the present invention or a composition comprising a biologically effective amount of the compounds of the present invention. In addition, there is a method where habitat is the soil, and the composition of the VNO is drawn into the soil in the form of a composition for impregnation of the soil. In addition, it should be noted that the compounds of the present invention are also effective in limited use at the site of infection. Other methods of contact include the application of the compounds or compositions of the invention direct and residual spraying, air spraying, using gels, by covering the seeds, microencapsulation, system absorption, as baits, ear tags, boluses, with an aerosol generator, in the form of fumigants, aerosols, Farrukh Dustov and much more. One of the variants of the method of contact is fertilizer in the form of a dimensionally stable pellets, sticks or tablets containing the compound or composition in accordance with the invention. Compounds of the present invention can also be used for impregnation of materials from which to fabricate the device to combat invertebrates (e.g., insect).

Compounds of the present invention is also used for seed treatment to protect them from invertebrate pests. In the context of the present description and formulas seed treatment means contacting the seed with a biologically effective amount of compounds in accordance with the present invention, which is typically included in the composition of the invention. This seed treatment protects them from soil invertebrate what pests and in General, can also protect the roots and other parts of the plant in contact with the soil, with the development of seedlings from germinating seed. Seed treatment can also protect the foliage as a result of moving the connection of the present invention or the second active ingredient inside the developing plants. Seed treatment can be applied to all types of seeds, including those of which will be to grow plants, genetically engineered for the expression of specialized features. Typical examples include plants expressing proteins toxic to invertebrate pests, such as toxinBacillus thuringiensisor plants expressing the genes for resistance to herbicides, such as glyphosate, acetyltransferase, which provides resistance to glyphosate.

One way of processing the seed is the spraying or sprinkling the seed compound in accordance with the invention (i.e. in the form of the composition) before sowing seeds. Compositions formulated for seed treatment usually contain a film-forming or adhesive agent. Therefore, usually the composition for seed coating of the present invention contains a biologically effective amount of a compound of the formula1its N-oxide or salt, as well as film-forming or adhesive agent. Seeds can be covered by restylene the liquid suspension concentrate directly on the movable seed layer, followed by drying seeds. Alternatively, seeds can be sprayed other types of compositions, such as moistened powders, solutions, suspoemulsions, emulsifiable concentrates and emulsions in water. This method, in particular, is suitable for application on the seed film coating. Specialist qualified in this field, will be able to use a different setup and coating methods. Suitable methods include the methods listed in P. Kosters et al.,Seed Treatment: Progress and Prospects, 1994, BCPC Mongraph No. 57 and listed references.

Treated seeds usually contain the compound of the present invention in amounts of from about 0.1 g to 1 kg per 100 kg of seeds (i.e. approximately of 0.0001-1% by weight of seeds before processing). Liquid suspension, prepared for seed treatment usually contains from about 0.5 to about 70% of the active ingredient, from about 0.5 to about 30% of the film-forming adhesive substance, from about 0.5 to about 20% of a dispersing agent, from 0 to about 5% thickening agent, from 0 to about 5% of a pigment and/or dye, from 0 to about 2% antifoam, from 0 to about 1% of a preservative and from 0 to about 75% of the volatile liquid diluent.

Compounds of the present invention can be included in the bait composition that is consumed besposlena the major pest or used within the device, for example, traps, lures and the like. This bait composition may be in the form of granules, which contain (a) the active ingredients, namely biologically effective amount of a compound of the formula1its N-oxide or salt; (b) one or more nutrients; optionally (c) an attractant, and optionally (d) one or more wetting agents. It should be noted pellets or bait compositions, which contain about 0.001 to 5% active ingredient, about 40-99% of nutrients and/or attractant; and optionally about 0.05-10% wetting substances, which are effective in controlling soil invertebrate pests at very low flow, particularly at doses of active ingredient, which are lethal when administered, not by direct contact. Some nutrients can function as a source of food and attractant. Nutrients include carbohydrates, proteins and lipids. Examples of nutrients are vegetable flour, sugar, starch, animal fat, vegetable oil, extracts of yeast and milk powder. Examples of attractants are flavors and flavoring, such as fruit or vegetable extracts, fragrances or other components of the animal is on or vegetable origin, pheromones or other agents which are known to attract the target bespozvonochnykh pest. Examples of wetting agents (moisture retaining agents are glycols and other polyols, glycerol and sorbitol. It should be noted baiting composition (and the method that uses the specified baiting composition), used to control at least one invertebrate pest selected from the group consisting of ants, termites and cockroaches. The unit for combating invertebrate pests may contain real bait composition and body, adapted for placing and baiting composition, where the housing has at least one hole, the dimensions of which allow bespozvonochnykh pest to pass through the opening indicated, resulting in the invertebrate pest can gain access to the bait composition from a position outside the housing, where the housing is additionally adapted for placement on the site or near the site of potential or known activity bespozvonochnykh pest.

Compounds of the present invention can be applied without other additives, but most will apply a composition containing one or more active ingredients with suitable carriers, diluents and surfactants, and in the options in combination with food, depending on the intended end use. One way of applying includes spraying the aqueous dispersion or solution of the compound of the present invention in refined oil. Combination with spray oils, concentration, spray oils, surfactants, additives, other solvents and synergistic agents such as piperonyl piperonyl often increase the efficiency of the connection. For non-agricultural applications, these sprays can be applied from aerosol containers, such as bottles, cans or other containers, either by using a pump or by using a vessel under pressure, for example aerosol container under pressure. Such spray compositions may be in various forms, for example in the form of sprays, aerosols, foams, vapors or smoke. These sprayable compositions, therefore, can optionally contain propellants, blowing agents, etc. depending on the circumstances. It should be noted sprayable composition comprising a biologically effective amount of the compounds or compositions of the present invention and a carrier. In one of the embodiments specified sprayable composition comprises a biologically effective amount of the compounds or compositions of the present invention and a propellant. Typical prop the tape include, but not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, Panten, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether and mixtures thereof. It should be noted sprayable composition (and the method that uses the specified sprayable composition is released from aerosol containers), used to control at least one invertebrate pest selected from the group consisting of mosquitoes, midges, gigalo, deer flies, horseflies, wasps, these wasps, hornets, ticks, spiders, ants, mosquitoes and the like, with individual pests or their combinations.

Non-agricultural uses include the protection of the animal, in particular a vertebrate animal, preferably a warm-blooded vertebrate animal (e.g. a mammal or bird) and most preferably a mammal, from bespozvonochnykh pest-parasite by introducing parasiticide effective (i.e. biologically effective amount of compounds of the invention, usually in the form of a composition formulated for veterinary use, protected animal. Thus, it should be noted way to protect the animal, including the introduction of animal parasiticide effective amount of compounds of the invention. The concept of "parasitically and parasitized what about the", used in this description and the formula, refer to the obvious effects exerted on bespozvonochnykh pest-parasite to protect the animal from the pest. Parasiticide effects are usually decrease in occurrence or activity of the target bespozvonochnykh pest-parasite. Such effects are exerted on the pest include necrosis, death, growth retardation, reduced mobility or reduced ability to remain on the body or in the body of an animal host, reduced food consumption and suppression of reproduction. These effects exerted on invertebrate pests, parasites, allow you to fight (including prevention, reduction or elimination) with parasitic infestation or infection in an animal. Examples of invertebrate pests pests that can be controlled by introducing a protected animal parasiticide effective amount of compounds of the invention include ectoparasites (arthropods, mites, etc) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, skrebni etc). In particular, the compounds of the present invention is effective against ectoparasites, including: flies, such asHaematobia(Lyperosia)irritans(gigalo cow small),Stomoxys calcitrans(gigalo autumn), the speciesSimulium(midges), the speciesGlossina(fly CE-CE),Hydrotaea irritans(the tooth of the leg), Musca autumnalis(fly autumn),Musca domestica(room fly),Morellia simplex(sweat fly), a species ofTabanus(horseflies),Hypoderma bovis,Hypodermalineatum,Lucilia sericata,Lucilia Cuprina(green meat fly), a species ofCalliphora(blowflies), a species ofProtophormia,Oestrus ovis(the gadfly sheep), a species ofCulicoides(midges),Hippobosca equine,Gastrophilus instestinalis,Gastrophilus haemorrhoidalisandGastrophilus naslis; ect., such asBovicola(Damalinia)bovis,Bovicola equi,Haematopinus asini,Felicola subrostratus,Heterodoxus spiniger,Lignonathus setosusandTrichodectes canis; runco, such asMelophagus ovinus; ticks, such as the speciesPsoroptes,Sarcoptes scabei,Chorioptes bovis,Demodex equithe speciesCheyletiella,Notoedres catithe speciesTrombiculaandOtodectescyanotis (ear mites); ticks, such as the speciesIxodesthe speciesBoophilusthe speciesRhipicephalusthe speciesAmblyommathe speciesDermacentorthe speciesHyalommaandHaemaphysalis; fleas, such asCtenocephalides felis(the cat flea) andCtenocephalides canis(dog flea).

Non-agricultural applications in the veterinary sector are the usual ways, such as enteral introduction in the form of, for example, tablets, capsules, drink, impregnating preparations, granules, pastes, boluses, add in the feeder, suppositories; or parenteral administration such as injection (including intramuscular, subcutaneous, intravenous, intraperitoneal), implants; nasal introduction; locally the introduction, for example, in the form of immersion or dipping, spraying, wetting, coating powder or applied on a small area of the body of the animal by products such as collars, ear tags, tail rings, foot rings or leashes, which contain compounds or compositions of the present invention.

Usually parasiticidal composition according to the present invention comprises a mixture of compounds of the formula1its N-oxide or salt with one or more pharmaceutically or veterinary acceptable carriers contain excipients and auxiliary means is selected depending on the intended route of administration (e.g. oral, topical or parenteral administration, such as injection) and in accordance with the standard method. In addition, a suitable carrier is chosen based on compatibility with one or more active ingredients in the composition, including parameters such as stability with respect to pH and moisture content. Thus, it should be noted composition for protecting an animal from an invertebrate pests, parasites, containing effective against parasites amount of compounds of the invention and at least one media device.

For parenteral administration, including intravenous, intramuscular and subcutaneous injection, the compound of the present invention can be applied in the t to be included in the suspension, solution or emulsion in oily or aqueous media and may contain such additives as suspendida, stabilizing and/or dispersing agents. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of the active ingredients (e.g. salt of active compound), preferably in physiologically compatible buffers containing other excipients or auxiliary means, known in the field of pharmaceutical compositions.

For oral administration, including solutions (most available for absorption form), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, blocks, kept in the rumen, feed blocks, the connection of the present invention can be mixed with a binder/filler, is suitable, as is known in the prior art for compositions intended for oral administration, such as sugars (e.g. lactose, sucrose, mannitol, sorbitol), starch (e.g. corn starch, wheat starch, rice starch, potato starch), cellulose derivatives (e.g. methylcellulose, carboxymethylcellulose, ethylhydroxylamine), protein derivatives (e.g., Zein, gelatin) and synthetic polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone). If necessary can be added lubricants (EmOC is emer, magnesium stearate), dezintegriruetsja agents (for example, cross-linked, polyvinylpyrrolidone, agar, alginic acid) and dyes or pigments. Pastes and gels often contain an adhesive substance (for example, gum Arabic, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminosilicate), contributing to the preservation of oral composition, which becomes difficult to spit out.

If parasiticide compositions are in the form of feed concentrates, the carrier usually chosen from high-quality forage, fodder cereals or protein concentrates. Such compositions containing feed concentrates, in addition to parasiticidal active ingredients may include additives that improve health or growth of animals, improving the quality of meat animals intended for slaughter, or otherwise useful for livestock. These additives may include, for example, vitamins, antibiotics, chemotherapeutic, bacteriostatic, fungistatic substances, coccidiostats and hormones.

Compounds of the present invention has been found to possess favorable pharmacokinetic and pharmacodynamic characteristics, ensuring system availability in oral introduction and ingestion. Thus, after a meal protected zhivotnymi.vozmozhno effective concentration of compounds of the invention in blood stream processed protect the animal from blood-sucking pests, such as fleas, ticks and lice. Thus, it should be noted composition for protecting an animal from an invertebrate pests, parasites in the form for oral administration (i.e. containing, in addition to parasiticide effective amount of compounds of the invention, one or more carriers selected from binders and fillers that are suitable for oral administration, and feed concentrates-media).

Compositions for local injection is usually made in the form of powder, creams, suspensions, spray, emulsion, foam, paste, aerosol, ointment, balm or gel. Typically, the composition for external use is a water-soluble solution that can be in the form of a concentrate to be diluted before use. Parasiticide compositions suitable for topical administration, usually contain the compound of the present invention and one or more carriers that are suitable for outdoor use. When applied externally parasiticidal composition applied to the surface of the animal body in the form of lines or spots (i.e. "spot" treatment), the active ingredient is expected to be absorbed for the most part or whole is covered with the outer surface. In the treated animal is preferably protected against invertebrate pests, which feed on the epidermis of the animal, such as CL the soup, fleas and lice. Thus, compositions for local introduction often contain at least one organic solvent, facilitating the movement of the active ingredient on the skin and/or penetration into the epidermis of the animal. The solvents normally used as carriers in these compositions include propylene glycol, paraffins, aromatic hydrocarbons, esters, such as isopropylmyristate, simple glycol ethers and alcohols, such as ethanol andn-propanol.

The level of consumption necessary for effective control of invertebrates (i.e. the "biologically effective amount")will depend on such factors as type bespozvonochnykh, the life cycle of the pest, life stage, its size, position, time of year, plant or animal host, feeding behavior, mating behavior, environment humidity, temperature and the like. Under normal environmental conditions, levels of consumption, constituting about 0.01 to 2 kg of active ingredients per hectare, sufficient for pest control in agricultural ecosystems, but may be just enough of 0.0001 kg/ha or up to 8 kg/ha. For non-agricultural applications effective costs range from approximately 1.0 to 50 mg/m2but it may be enough just 0.1 mg/m2 or up to 150 mg/m2. Specialist, skilled in this field can easily identify biologically effective amount necessary for the desired level of combating invertebrate pests.

As a rule, for veterinary use the connection formula1its N-oxide or salt is administered in parasiticide effective amount of the animal to be protected from invertebrate pests, parasites. Parasiticide effective amount is an amount of active ingredient needed to achieve obvious effect, which consists in reducing the occurrence or activity of the target bespozvonochnykh pest-parasite. Specialist, skilled in this field can appreciate that parasiticide effective dose may vary depending on various compounds and compositions of the present invention, the desired effect on parasites and its duration, the target species of invertebrate pests of protected animal, route of administration and the like, the number needed to achieve a particular result can be determined by simple experiment.

For oral administration of a warm-blooded animal daily dose of a compound of the present invention generally ranges from about 0.01 mg/kg to priblizitel is but 100 mg/kg, basically, from about 0.5 mg/kg to about 100 mg/kg, per body weight of the animal. In the case of local (e.g., skin) injection solutions and sprays usually contain from about 0.5 hours/million to approximately 5000 hours/million, mainly, from about 1 hour/million to approximately 3000 hours/million compounds of the present invention.

In index tables A-C, below, the following abbreviations are used:imeansfrom,t-tert,cis cyclo, Me is methyl, Et is ethyl,c-Pr cyclopropyl andt-Bu -tert-butyl. Naphthyl means naphthalenyl. (R) or (S) denote the absolute chirality of asymmetric Central carbon atom. The abbreviation "Etc." means "Example" and is accompanied by a number that indicates in which the sample was received on the connection. In index table A (R2)mrefers to the combination (R2)nin cases of CR2for B1B2and B3.

TABLE INDEXES A

/tr>
ConnectionW(R2)mR4R5TPL(°C)
1 (PR. 1) About3-Cl,5-ClHCH2CF3**
2 (PR. 2)About3-Cl,5-ClHCH2-2-pyridinyl**
3AboutHHCH2CF3*
4AboutHHCH2-2-pyridinyl*
5About3-Cl,5-ClHCH2-phenyl*
6About3-Cl,5-ClHCH2-3-pyridinyl*
7About3-Cl,5-ClHCH2-4-pyridinyl*
8 (PR. 3)S3-Cl,5-ClHCH2-2-pyridinyl**
9About3-Cl,5-ClMeEt*
10About3-Cl,5-ClHEt*
11About3-Cl,5-ClCO2MeCH2-2-pyridinyl*
12About3-Cl,5-ClHMe*
13About3-Cl,5-ClHCH2CH2N(CH3)2*
14About3-Cl,5-ClHCH 2CH2N(CH3)2·Model HC1*
15About3-Cl,5-ClH(R)-CH(CH3)-phenyl*
16About3-Cl,5-ClHCH(CH3)2*
17About3-Cl,5-ClH(S)-CH(CH3)-phenyl*
18About3-Cl,5-ClHCH2CH=CH2*
19About3-Cl,5-ClHCH2C≡CH*
20About3-Cl,5-ClHCH2-c-Pr*
21About 3-Cl,5-ClHCH(CH3)-2-pyridinyl*
22About3-Me,5-MeHCH2-2-pyridinyl*
23About3-Cl,4-ClHCH2-2-pyridinyl*
24About3-F,5-FHCH2-2-pyridinyl*
25About3-ClHCH2-2-pyridinyl*
26About3-Br,5-BrHCH2-2-pyridinyl*
27About3-Cl,5-ClH(R)-CH(CH3)-2-naphthyl*
28About3-Cl,5-ClH(R)-CH(CH3)-(4-NO2-phenyl)*
29About3-Cl,5-ClH(S)-CH(CO2CH3)-phenyl*
30About3-Cl,5-ClH(R)-CH(CH3)-(4-Cl-phenyl)*
31About3-Cl,5-ClH(R)-CH(CH3)-(4-F-phenyl)*
32About3-Cl,5-ClH(R)-CH(CH3)CH2CH3*
33About3-Cl,5-ClHCH(CH3)CH2CH3*
34About3-Cl,5-Cl H(R)-CH(CH3)-t-Bu*
35About3-Cl,5-ClHCH2CH2OH*
36About3-Cl,5-ClHH*
37About3-Cl,5-ClH-CH2CH2N(CH3)CH2CH2-*
38O3-Cl,5-ClH*
39O3-Cl,5-ClH*
40O3-Cl,5-ClH*
41O3-Cl,5-ClHCH2CH2OCH3*
42O3-Cl,5-ClHCH2CO2Et*
43O3-Cl,5-ClHCH2CO2H*
44O3-Cl,5-ClHCH2CO2Na*
45O3-Cl,5-ClHNHC(=O)Me*
46O3-Cl,5-ClHNH-phenyl*
47O3-Cl,5-ClHCH2CH2NH2 *
48O3-Cl,5-ClH(S)-CH(Me)CO2Me*
49O3-Cl,5-ClH(S)-CH(i-Pr)CO2Me*
50O3-Cl,5-ClHCH2(CH2)5NH2*
51O3-Cl,5-ClHCH2CONHCH2CF3*
52O3-Cl,5-ClHCH2CN*
53O3-Cl,5-ClHNH-2-pyridinyl*
*Data1H-NMR, see table indexes D. ** Data1H-NMR, see examples.

Table indexes
ConnectionWAnd1And2And3And4And5And6R4R5TPL (°C)
101AboutNSNSNSNSNSNNCH2-2-pyridinyl*
102AboutSNNSN SNSNSNHCH2-2-pyridinyl*
103 (PR)AboutSNSNNSNSNSNHCH2-2-pyridinyl**
104 (PR)AboutSNSNSNNSNSNHCH2-2-pyridinyl**
105AboutSNSNSNSN NSNHCH2-2-pyridinyl*
106AboutSNSNSNSNSNNHCH2-2-pyridinyl*
107AboutSNSNSNSNSNNHCH2CF3
108SSNSNSNSNSN NHCH2-2-pyridinyl
109SSNSNSNSNSNNHCH2CF3*
110AboutSNCLO3SNSNSNSNHCH2-2-pyridinyl*
111AboutSNCLO3SNSNSNSNCH2CF3*
*Data1H-NMR, see table indexes D. **Data1H-NMR, see examples.
TABLE INDEXES
ConnectionIn1B2In3(R2)nR4R5R1TPL (°C)
201S-C1NSNHHCH2CF3CF3*
202S-C1NWith the HHCH2-2-pyridinylCF3*
*The data of 1H-NMR, see table indexes D.
TABLE INDEXES D
ConnectionNo data1H-NMR (solution in CDCl3if not stated otherwise)and
3δ 8,67 (d, 1H), of 8.06 (d, 1H), 7, 66-7,45 (mr7H), 7,39 (d, 1H), 7,29 (d, 1H), 6,78 (Shir. with 1H), 4,19 (d, 1H), 4,15 (m, 2H), 3,88 (d, 1H).
4δ 8,82 (d, 1H), and 8.50 (d, 1H), 8,35 (d, 1H), 7,71-7,44 (m, 11N), 7,35 (d, 1H),7,20 (DD, 1H), a 4.83 (d, 2H), 4.25 in (d, 1H), 3,95 (d, 1H).
5δ 8,78 (d, 1H), 8,27 (d, 1H), 7, 64-7, 30 (m, N), 6,40 (Shir. t 11N), 4,71 (d, 2H), 4,22 (d, 1H), 3,86 (d, 1H).

6δ 8,72 (d, 1H), 8,53 (d, 1H), 8,49 (DD, 1H), 8,18 (d, 1H), 7,72 (d, 1H), 7,60-7,52 (m, 4H), 7,45 (m, 2H), was 7.36 (d, 1H), 7,27 (m, 1H), 6,93 (shirt, 1H), of 4.66 (d, 2H), 4,21 (d, 1H), 3,86 (d, 1H).
7δ 8,72 (d, 1H), and 8.50 (d, 2H), 8,19 (d, 1H), to 7.61 to 7.4 (m, 4H), 7,47 (m, 2H), 7,37 (d, 1H), 7.23 percent (d, 2H), 7,02 (shirt, 1H), of 4.66 (d, 2H), 4,22 (d, 1H), 3,86 (d, 1H).
9δ 8,88 (m, 1H), 7,83 (m, 1H), 7,66-7,40 (m, 7H), 4,27 (l,
1H), 3,92 (d, 1H), 3,80-3,66 and to 3.09 (m, 2H), 3,22 and is 2.74 (s, 3H), 1.01 and of 1.36 (t, 3H).
10δ 8,78 (d, 1H), of 8.25 (d, 1H), of 7.64-7,42 (m, 7H), between 6.08 (Sirs, 1H), 4,24 (d, 1H), 3,88 (d, 1H), to 3.58 (m, 2H), 1,31 (t, 3H).
11δ of 8.92 (d, 1H), 8,63 (d, 1H), 8,17 (d, 1H), 7,74-7,53 (m, 7H), was 7.45 (t, 1H), 7,35 (d, 1H), 7.23 percent (DD, 1H), 5,33 (s, 2H), 4,29 (d, 1H), 3,92 (d, 1H), 3.43 points (s,3H).
12δ 8,77 (d, 1H), 8,21 (d, 1H), 7,63-of 7.55 (m, 5H), 7,44 (d, 1H), 7,38 (d, 1H), 6,18 (Sirs, 1H), 4,23 (d, 1H), a 3.87 (d, 1H), of 3.07 (d, 3H).
13δ 8,78 (d, 1H), 8,27 (d, 1H), 7,39 to 7.62 (m, H), 6,77 (Sirs, 1H), 4,22 (d, 1H), 3,88 (d, 1H), to 3.58 (q, 2H), 2,53 (t, 2H, in), 2.25 (s, 6H).
15δ 8,63 (DD, 1H), 8,00 (DD, 1H), 7,56 (s, 2H), 7,47-7,16 (m, 9H), is 6.78 (DD, 1H), of 5.34 (m, 1H), 4,14 (DD, 1H), 3,80 (DD, 1H), 1,60 (d, 3H).
16δ 8,80 (d, 1H), of 8.25 (d, 1H), 7,66 was 7.45 (m, 7H), by 5.87 (d, 1H), to 4.41 (m, 1H), 4,24 (d, 1H), 3,88 (d, 1H), 1,33 (d,6H).
17δ 8,77 (d, 1H), 8,19 (DD, 1H), 7,63-7,30 (m, 12H), 6,30 (d, 1H), 5,44 (m, 1H), 4,22 (d, 1H), 3,86 (d, 1H), 1,67 (d, 1H).
18δ 8,80 (d, 1H), 8,27 (d, 1H), to 7.67 was 7.45 (m, 7H), 6,15 (shirt, 1H), of 5.99 (m,1H), 5,31 (d, 1H), 5,24 (d, 1H), 4,25 (d, 1H), 4,17 (m, 2H), 3,88 (d, 1H).
19δ 8,77 (d, 1H), 8,24 (d, 1H), of 7.64-7,56 (m, 4H), to 7.50 (d, 1H), 7,46 (DD, 1H), 7,40 (d, 1H), 6,38 (shirt, 1H), 4,33 (DD, 2H), 4,23 (d, 1H), a 3.87 (d, 1H),2,32 (t, 1H).
20δ 8,82 (d, 1H), 8,29 (d, 1H), to 7.67 was 7.45 (m, 7H), 6,14 (Sirs, 1H), 4.26 deaths (d, 1H), 3,90 (d, 1H), 3,42 (DD, 2H), 1,12 (m, 1H), 0,59 (m, 2H), 0,32 (m, 2H).
21δ 8,82 (d, 1H), and 8.50 (d, 1H), 8.34 per (d, 1H), 7,72 (dt, 1H), to 7.67-EUR 7.57 (m, 6H), to 7.50 (d, 1H), 7,45 (DD, 1H), 7,34 (d, 1H), 7,21 (DD, 1H), the 5.45 (m, 1H), 4.26 deaths (d, 1H), 3,90 (d, 1H), of 1.66 (d,3H).
22δ cent to 8.85 (d, 1H), 8,51 (d, 1H), at 8.36 (d, 1H), 7,72-EUR 7.57 (m, 4H), 7,51 (d, 1H), 7,45 (shirt, 1H), was 7.36 (d, 1H), 7,25 (s, 2H), 7,21 (DD, 1H), 7,07 (s, 1H), around 4.85 (d, 1H), 4,22 (d, 1H), 3,94 (d, 1H), of 2.38 (s, 6H).
23δ 8,81 (d, 1H), 8,51 (d, 1H), of 8.37 (d, 1H), 7,78-7,46 (m, 9H), was 7.36 (d, 1H), 7,22 (DD, 1H), around 4.85 (d, 2H), 4.26 deaths (d, 1H), 3,90 (d, 1H).
24δ 8,83 (d, 1H), charged 8.52 (d, 1H), 8,39 (d, 1H), 7,74-7,22 (m, H)6,91 (dt, 1H), 4,87 (d, 2H), 4,27 (d, 1H), 3,90 (d, 1H).
25δ 8,83 (d, 1H), 8,51 (d, 1H), of 8.37 (d, 1H), 7,73-7,41 (m, 10H), 7,37 (d, 1H), 7,22 (DD, 1H), a 4.86 (d, 2H), 4.26 deaths (d, 1H), 3,92 (d, 1H).
26δ 8,82 (d, 1H), charged 8.52 (d, 1H), scored 8.38 (d, 1H), 7,76 (s, 2H), 7,74-to 7.59 (m, H), 7,52 (d, 1H), 7,44 (shirt, 1H), 7,37 (d, 1H), 7.23 percent (DD, 1H), 4,87 (d, 2H), 4.26 deaths (d, 1H), 3,90 (d, 1H).
27δ 8,76 (d, 1H), 8,19 (DD, 1H), 7,87 and 7.36 (m, 14H), 6,46 (d, 1H), 5,59 (m, 1H), 4,20 (d, 1H), 3,84 (d, 1H), 1,73 (d, 3H).
28δ 8,77 (d, 1H), 8,23 (d, 2H), 8,14 (DD, 1H), 7,66-7,44 (m, 9H), of 6.45 (d, 1H), vs. 5.47 (m, 1H), 4,24 (d, 1H), 3,88 (d, 1H), of 1.66 (d, 3H).
29δ 8,80 (d, 1H), 8,28 (d, 1H), 7,66-7,37 (m, H), of 6.99 (d, 1H), by 5.87 (d, 1H), 4,24 (d, 1H), 3,88 (d, 1H), 3,80 (s, 3H).
30δ 8,76 (d, 1H), 8,14 (DD, 1H), 7,63-7,35 (m, 11H), 6.35mm (d, 1H), 5,38 (m, 1H), 4,21 (d, 1H), 3,85 (d, 1H), 1,62 (d, 3H).
31δ 8,76 (d, 1H), 8,16 (DD, 1H), of 7.64-7,38 (m, 9H), 7,07 (d, 1H), 7,05 (d, 1H), 6.30-in (d, 1H), 5,41 (m, 1H), 4,22 (d, 1H), 3,86 (d, 1H), 1,64 (d, 3H).
32δ 8,81 (d, 1H), compared to 8.26 (d, 1H), to 7.67 was 7.45 (m, 7H), 5,78 (d, 1H), 4.26 deaths (d, 1H), 4,25 (m, 1H), 3,88 (d, 1H), and 1.63(m, 2H), of 1.30 (d, 3H), was 1.04 (t, 3H).
33δ 8,81 (d, 1H), compared to 8.26 (d, 1H), to 7.67 was 7.45 (m, 7H), 5,78 (d, 1H), 4.26 deaths (d, 1H), 4,25 (m, 1H), 3,88 (d, 1H), and 1.63 (m, 2H), of 1.30 (d, 3H), was 1.04 (t, 3H).
34δ 8,80 (d, 1H), compared to 8.26 (d, 1H), 7.68 per-7,46 (m, 7H), 5,80 (d, 1H), 4.26 deaths (d, 1H), 4,23 (m, 1H), 3,88 (d, 1H), 1,24 (d, 3H), of 1.01 (s, 9H).
35δ 8,65 (d, 1H), 8,08 (d, 1H), 7,55 (s, 2H), 7,52-7,44 (m, 7H), 7,27 (d, 1H), 7,19 (d, 1H), 6,93 (shirt, 1H), 4.16 the (d, 1H), 3,81 (d, 1H), of 3.73 (s, W, 2H); of 3.53 (m, 2H), 3.27 to (Sirs, 1H).
36 δ is 8.75 (d, 1H), 8.30 to (d, 1H), 7,63-7,35 (m, 7H), 6,69 (Sirs, 1H), 6,32 (Sirs, 1H), 4,22 (d, 1H), 3,86 (d, 1H).
38δ 8,79 (m, 1H), 8.34 per (d, 1H), of 7.64 for 7.12 (m, 11H), of 6.29 (DD,1H), 5,50 (m, 1H), 4,22 (d, 1H), a 3.87 (d, 1H), 2,82 (m, 2H), 2,24 (m, 1H), 2.05 is (m, 1H), 1.91 a (m, 2H).
39δ 8,80 (d, 1H), 8.34 per (d, 1H), 7-65-7,25 (m, H), 6:28 (d, 1H), 5,79 (kV, 1H), 4,24 (d, 1H), a 3.87 (d, 1H), 3,92-of 3.07 (m, 2H), 2,77 (m, 1H), 1,99 (m, 1H).
40δ 8,81 (d, 1H), of 8.37 (d, 1H), to 7.67-7,26 (m, H), of 6.26 (d, 1H), 5,80 (kV, 1H), 4,24 (d, 1H), 3,88 (d, 1H), 3,09-of 2.93 (m, 2H), and 2.79 (m, 1H), 1,99 (m, 1H).
41δ 8,82 (d, 1H), 8.30 to (d, 1H), to 7.67-7,46 (m, 7H), 6,40 (shirt, 1H), 4,25 (d, 1H), 3,89 (d, 1H, in), 3.75 (q, 2H), 3,63 (DD, 2H), 3,39 (s, 3H).
42δ 8,84 (d, 1H), of 8.37 (d, 1H), to 7.67-7,46 (m, 7H), 6,53 (shirt, 1H), 4,33 (d, 2H), 4,29 (kV, 2H), 4.26 deaths (d, 1H), 3,90 (d, 1H), of 1.34 (t, 3H).
43DMSO-d6:δ 9,02 (t, 1H), 8,81 (d, 1H), of 8.37 (d, 1H), 7,92 (d, 1H), 7,83 (t, 1H), 7,74-the 7.65 (m, 5H), 4,58 (d, 1H), 4,54 (d, 1H), was 4.02 (d, 2H).
44DMSO-d6:δ 8,86 (d, 1H), and 8.50 (d, 1H), of 7.96-to 7.67 (m, 8H), br4.61 (apparent s, 2H), 3,64 (d, 2H).
45DMSO-d6:δ 10,44 (s, 1H), 10,10 (s, 1H), 8,86 (d, 1H), 8,46 (d, 1H), 7,98 (d, 1H), of 7.90 (t, 1H), 7,76 (m, 5H), 4,63 (d, 1H), 4,59 (d, 1H), 2,04 (s, 3H).
46 δ 10,45 (s, 1H), 8,80 (d, 1H), 8,24 (d, 1H), 7,95 (d, 1H), 7,85-7,63 (m, 7H), 7,22 (m, 2H), 6.90 to (d, 2H), 6,78 (t, 1H), 4,57 (apparent s, 2H).
47δ 8,83 (d, 1H), with 8.33 (d, 1H), 7,69-7,46 (m, 9H), 6,54 (Sirs, 1H), 4,27 (d, 1H), 3,90 (d, 1H), 3,61 (kV, 2H), to 3.02 (t, 3H).
48δ 8,83 (d, 1H), 8,35 (d, 1H), 7.68 per-7,46 (m, 7H), is 6.54 (d, 1H), 4,91 (m, 1H), 4.26 deaths (d, 1H), 3,90 (d, 1H), 3,83 (s, 3H), 1,60 (d, 3H).
49δ 8,84 (d, 1H), 8.34 per (d, 1H), 7,70-7,46 (m, 7H), 6,46 (d, 1H), 4,91 (DD, 1H), 4.26 deaths (d, 1H), 3,90 (d, 1H), 3,83 (s, 3H), of 2.36 (m, 1H), 1,10 (d, 3H), 0,99 (d, 3H).
50DMSO-d6:δ 8,79 (d, 1H), 8,71 (t, 1H), 8,19 (d, 1H), 8,08 (Sirs, 2H), of 7.90 (d, 1H), to 7.84 (DD, 1H), 7,73-7,66 (m, 4H), a 7.62 (d, 1H), 4,54 (apparent s, 2H), 3,35 (m, 2H), was 2.76 (m, 2H), 1,60 (m, 4H), of 1.39 (m, 4H).
51δ 8,82 (d, 1H), compared to 8.26 (d, 1H), to 7.67-7,46 (m, 7H), to 7.09(m, 2H), 4,28 (d, 2H), 4.25 in (d, 1H), 3.96 points (m, 2H), 3,88 (d, 1H).
52δ 8,79 (d, 1H), 8,23 (d, 1H), 7.68 per-7,46 (m, 7H), 6,53 (shirt, 1H), 4,46 (d, 2H), 4.26 deaths (d, 1H), 3,89 (d, 1H).
53δ 8,83 (d, 1H), 8,42 (d, 1H), 8,18 (d, 1H), 7,73 (d, 1H), 7,70-of 7.55 (m, 7H); 7,50 (d, 1H), 7,46 (DD, 1H), 6,84 (DD, 1H), 6,80 (d, 1H), 4.26 deaths (d, 1H), 3,90 (d, 1H).
101δ 9,24 (d, 1H), up 8.75 (s, 1H), charged 8.52 (d, 1H), 8,45 (d, 1H), 7,82-of 7.70 (m, 3H),of 7.64 (Sirs, 1H), 7,58 (s, 2H), 7,44 (t, 1H), 7,37 (d, 1H), 7,24 (DD, 1H), 4,87 (d, 2H).
102δ 9,63 (d, 1H), 9,04 (shirt, 1H), 8,93 (d, 1H), at 8.60 (d, 1H), charged 8.52 (s, 1H), 7,86 (DD, 1H), 7,74 (DD, 1H), 7,69 (DD, 1H), EUR 7.57 (s, 2H), 7,46 (DD, 1H), 7,40 (d, 1H), 7.23 percent (DD, 1H), around 4.85 (d, 2H), or 4.31 (d, 1H), 3,94 (d, 1H).
105δ 10,17 (s, 1H), 8,64 (d, 1H), 8,53 (d, 1H), they were 8.22 (d, 1H), of 7.90 (d, 1H), 7,73 (dt, 1H), 7,68 (shirt, 1H), to 7.59 (d, 1H), 7,56 (s, 2H), 7,46 (t, 1H), 7,37 (d, 1H), 7,24 (DD, 1H), around 4.85 (d, 2H), 4,27 (d, 1H), 3,92 (d, 1H).
106δ of 8.95 (DD, 1H), 8,88 (DD, 1H), 8,55 (d, 1H), compared to 8.26 (d, 1H), 7,83 (d, 1H), 7,72 (dt, 1H), 7,60 is 7.50 (m, 4H), 7,43 (t, 1H), was 7.36 (d, 1H), 7,24 (DD, 1H), around 4.85 (d, 2H), 4.72 in (d, 1H), 4,42 (d, 1H).
107δ 8,89,(DD, 1H), 8,61 (d, 1H), to 7.99 (d, 1H), to 7.59 (d, 1H), 7,55 (s, 2H), 7,45 (m, 2H), 6.89 in (shirt, 1H), and 4.68(d, 1H), 4,32 (d, 1H), 4,18 (m, 2H).
108δ 9,41 (Sirs, 1H), 8,91 (DD, 1H), 8,70 (DD, 1H), 8,46,(d, 1H), 8,21 (d, 1H), of 7.75 (dt, 1H), to 7.64 (d, 1H), EUR 7.57 (s, 2H), 7,47 (DD, 1H), 7,43 (t, 1H), 7,38 (d, 1H), 7,24 (DD, 1H), 5,14 (d, 2H), and 4.68 (d, 1H), 4,39 (d, 1H).
109δ 8,88 (d, 1H), of 8.47 (DD, 1H), 8,12 (Sirs, 1H), of 7.97 (d, 1H), 7,53 (s, 2H), 7,47 (m, 3H), 4,74 (m, 2H), 4,59 (d, 1H), 4,25 (d, 1H).
110δ is 8.75 (d, 1H), 8,42 (d, 1H), 7,86 (d, 1H), 7,68 (dt, 1H), EUR 7.57 (s, 2H), 7,55-to 7.35 (m, 5H), 7,31 (s, 1H), 7,18 (DD, 1H), 4,82 (d, 2H), 4.25 in (d, 1H), 3,90 (d, 1H), 2,44 (s, 3H).
111δ 8,59 (d, 1H), 7,58 (s, 2H), 7,54 (d, 1H), 7,47 (t, 1H), was 7.36-7,44 (m, 2H), 7,10 (s, 1H), 6,80 (W is RT, 1H), 4,20 (d, 1H), 4,08 (m, 2H), 3,86 (d, 1H), of 2.23 (s, 3H).
201δ 8,71 (d, 1H), 8,48 (m, 1H), 8,13 (d, 1H), 7,55-to 7.64 (m, 3H), 7,49 (d, 1H), 7,44 (d, 1H), 7,35 (DD, 1H), 6,74 (t, 1H), 4,24 (d, 1H), 4,17 (m, 2H), 3,83 (d, 1H).
202δ 8,79 (d, 1H), and 8.50 (m, 2H), 8,35 (d, 1H), 7,50-7,72 (m, 7H), 7,47 (d, 1H), was 7.36 (d, 1H), 7,22 (DD, 1H), a 4.83 (d, 2H), 4,28 (d, 1H), 3,89 (d,1H).
*Data1H-NMR are given in ppm downwards from tetramethylsilane. Pairs marked as follows: (s) - singlet, (d) - doublet, (t) triplet, (q) Quartet, (m) - multiplet, (DD) doublet of doublets, (dt) - doublet of triplets, (Sirs) - broad singlet, (shirt) - broad triplet.

BIOLOGICAL EXAMPLES of the INVENTION

The following tests demonstrate the effectiveness of the compounds of the present invention to control specific pests. "Efficiency in the fight" means the inhibition of the development of invertebrate pests (including mortality), which causes a significant reduction in food intake. Protection from pests, provide compounds of the present invention is not limited, however, with the specified types. The description of the compounds, see index tables A-C.

TEST A

Testing device for evaluation against cabbage moth (Plutella xylostella) consisted of a small open container or road is and with 12-14-day radish plants. Plants pre-infected 50 newborn larvae, distributed on the test device by using the crushed core piece of corn using the dry inoculant-bazookas. Larvae were moved to the test plant after the distribution of the test device.

The tested compounds were introduced into the composition by using a solution containing 10% acetone, 90% water and 300 hours/million non-ionic surfactant X-77™ Spreader Lo-Foam Formula, containing alkalinisation, free fatty acids, glycols and isopropanol (Loveland Industries, Inc.). Made in the composition of the compound was applied in a volume of 1 ml of liquid through the nozzle SUJ2 with special housing 1/8 JJ (Spraying Systems Co. Wheaton, Illinois, USA), located at a distance of 1.27 cm (0.5 inch) above the upper part of each test device. All experimental compounds in these tests was sprayed at a concentration of 250 and/or 50 hours per million, and the test was repeated three times. After spraying of the composition of the tested compounds each test device was dried for 1 hour, and then on the top was placed a black lid with holes. The test device was kept for 6 days in the chamber to grow at 25°C and a relative humidity of 70%. Then, on the basis of the number of absorbed foliage visually illustrates ivali damage to plants, it was also expected mortality for each test device.

Of the tested compounds of the formula1these demonstrate very good or excellent level of efficiency of plant protection (damage 20% or less, or a mortality of 80% or higher): 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38, 39, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 101, 102, 103, 104, 105, 106, 107*, 108*, 109*, 110, 111, 201 and 202 (* means very good or excellent level of efficiency of protection of plants observed only at 250 hours/million).

TEST B

Testing device for evaluation of the combating autumn Sovkome (Spodoptera frugiperda) consisted of a small open container with a 4-5-day plant corn (maize). Plants pre-infected 10-15 day larvae on a piece nourishing environment for insects. Connections were made in the composition and sprayed at a concentration of 250 and/or 50 hours per million as described in the test And the test was repeated three times. After spraying the test device was kept in the cell for growth, then the efficiency of plant protection was evaluated for each test device as described in test A.

Of the tested compounds of the formula1these demonstrate very good or excellent level of efficiency of plant protection (damage 20% and less than or mortality of 80% or above): 1, 2, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 39, 41, 42, 46, 49, 51, 101, 102, 103, 104, 106*, 107*, 110*, 111*, 201 and 202 (* means very good or excellent level of efficiency of protection of plants observed only at 250 hours/million).

TEST C

Testing device for evaluation of the fight against potato leafhopper (Empoasca fabaeHarris) through contact and/or systemic methods consisted of a small open container with a 5-6-day plants (first leaves) yellow beans inside. On the soil surface was covered with white sand and one of the first leaves cut off before the test. The test compounds were made in the composition and sprayed at 250 and/or 50 hours/million, and the test was repeated three times, as described in test A. After spraying the test device was dried for 1 hour, after which they were infected 5 potato cicadae (adult age from 18 to 21 days). The cylinder was placed a black lid with holes. Test device for 6 days was kept in the cell for growth at 19-21°C and a relative humidity of 50-70%. Then mortality of insects were visually evaluated the effectiveness of plant protection for each test device.

Of the tested compounds of the formula1these demonstrate very good or excellent level of efficiency of protection of the plant is th (mortality of 80% or above): 1, 2, 8, 10, 11, 14*, 15, 16, 18*, 19, 20, 21, 26, 28, 31, 32*, 34, 36, 38, 46*, 101, 102* and 106* (* means very good or excellent level of efficiency of protection of plants observed only at 250 hours/million).

TEST D

Testing device for evaluation of the combating flower thrips (Frankliniella occidentalis) through contact and/or systemic methods consisted of a small open container with a 5-7-day plants yellow beans inside. The test compounds were made in the composition and sprayed at 250 and/or 50 hours/million, and the test was repeated three times, as described in test A. After spraying the test device was dried for 1 hour, and then each device was placed 22-27 adult thrips, then on the top was placed a black lid with holes. The test device was kept for 6 days at 25°C and a relative humidity of 45-55%. The mortality assessment was conducted along with an assessment of crop damage for each test device.

Of the tested compounds of the formula1these demonstrate very good or excellent level of efficiency of plant protection (damage 20% or less, or a mortality of 80% or higher): 1, 2, 8, 10, 11, 13*, 14*, 15*, 16, 18, 19, 20*, 21, 26, 32, 33*, 34*, 35, 39*, 41, 42, 45*, 46*, 47*, 48*, 49, 51, 101 and 104 (* means very good or excellent the effectiveness of plant protection, the observed thickness of the co at 250 hours/million).

TEST E

To assess the effectiveness of the fight against the cat flea (Ctenocephalides felisBouche) mouse CD-1® (weighing approximately 30 g, male, obtained from Charles River Laboratories, Wilmington, MA) was administered orally the test compound, dissolved in a mixture of propylene glycol/glycerol (60:40), at a dose of 10 mg/kg two hours after oral administration of test compounds approximately 8-16 adult fleas were placed on each mouse. 48 hours after infection, mice, fleas estimated mortality of fleas.

Of the tested compounds, the following compounds were caused mortality of 30% or higher: 1*, 2, 10*, 41* 51* (* means that the compound caused a mortality of 50% or above).

1. The compound of formula 1 or its suitable for agriculture salt,

where a1And2And3And4And5and6independently selected from the group consisting of CR3and N, provided that at most 1 of the A1And2And3And4And5and6represent N;
In1In2and3independently selected from the group consisting of CR2and N;
W represents O or S;
R1represents a C1-C6alkyl, optionally substituted with up to three substituents, independently selected from R6;
each R2independently represents H, halogen, C1-the 6alkyl, C1-C6halogenated,1-C6halogenoalkane;
each R3independently represents N or C1-C6alkyl;
R4represents H, C1-C6alkyl or C2-C7alkoxycarbonyl;
R5represents N, NR11R12or Q1; or (C1-C6alkyl, each optionally substituted with up to three substituents, independently selected from R7;2-C6alkenyl,2-C6quinil,3-C6cycloalkyl,4-C7alkylsilane;
each R6independently represents a halogen;
each R7independently represents halogen, carboxylic acid, naphthyl,3-C6cycloalkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl,1-C6alkylsulfonyl, C1-C6alkylamino,2-C8dialkylamino,2-C7alkoxycarbonyl,2-C7alkylaminocarbonyl,3-C9dialkylaminoalkyl,2-C7halogenlithiumcarbeniod,3-C9halogenoaluminates, hydroxy, -NH2, -CN; or Q2;
each R9independently represents halogen, C1-With6alkyl, C1-C6halogenated, -NO2;
R11represents the t a N, With2-C7alkyl, C2-C7alkylsulphonyl;
R12represents H; Q3; or (C1-C6alkyl, or R11and R12taken together with the nitrogen atom to which they are attached, form a 5-or 6-membered ring containing 4 or 5 carbon atoms, where the aforementioned ring is optionally substituted by 1 or 2 substituents, independently selected from the group consisting of halogen;
Q1is a 9 - or 10-membered condensed bicyclic ring system;
each Q2independently represents a phenyl ring or a 5-or 6-membered heterocyclic ring, each ring optionally substituted up to two substituents, independently selected from R9;
Q3is a phenyl ring or pyridinoline ring, optionally substituted by up to two substituents, independently selected from R9;
n is 0, 1 or 2.

2. The compound according to claim 1, where
R1represents a C1-C3alkyl, optionally substituted with up to three substituents, independently selected from R6;
each R2independently represents H, halogen, C1-C6halogenated or C1-C6halogenoalkane.

3. The compound according to claim 2, where
In1In2and3independently represent CR2;
R5represents N, NR11R12, Q1; or (C1-C6alkyl, each optionally substituted with up to three substituents, independently selected from R7;3alkenyl,3quinil,3cycloalkyl;
each R7independently represents halogen, carboxylic acid, naphthyl,3cycloalkyl, C1alkoxy, C1-C4alkylthio, C1-C2alkylsulfonyl,1-C2alkylsulfonyl, C2-C3alkylamino,2-C3dialkylamino,2-C5alkoxycarbonyl,2-C6alkylaminocarbonyl,4dialkylaminoalkyl,2-C5halogenlithiumcarbeniod, hydroxy, -NH2, -CN; or Q2;
and
W represents O.

4. The compound according to claim 3, where
R1represents a C1-C3alkyl, optionally substituted with halogen; each R2independently represents H, CF3, OCF3or halogen; and
each R7independently represents halogen, C1-C4alkoxy, C1-C4alkylthio,1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C4alkoxycarbonyl,2-C5alkylaminocarbonyl,2-C5halogenlithiumcarbeniod, -NH2, -CN; or Q2.

5. The compound according to claim 4, where R4before the hat is N;
R5represents a C1-C4alkyl, optionally substituted with up to three substituents, independently selected from R7;
each R7independently represents halogen or Q2;
each Q2independently represents a phenyl, pyridinyl or thiazolyl.

6. The compound according to claim 5, where
R1is a CF3;
each And1And2And3And4And5and6represents CR3;
In2represents CR2;
each R3independently represents N or C1-C4alkyl.

7. The connection according to claim 6, where
In2represents CH;
R3represents H;
R5represents CH2CF3or CH3-2-pyridinyl; and
n is 0.

8. The compound according to claim 1, which is selected from the group consisting of:
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenemethylamine,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-]-N-ethyl-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-what ethoxyethyl)-1-naphthaleneboronic,
5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-chinainternational,
5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-chinainternational and
1-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-ethanolinduced.

9. Composition for combating insects, containing insecticide effective amount of a compound according to claim 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

10. The composition according to claim 9, additionally containing a biologically effective amount of at least one additional biologically active compound or agent that is active against insects.

11. The composition of claim 10, where at least one additional biologically active compound or agent selected from insecticides of the group consisting of modulators of sodium channels, cholinesterase inhibitors, neonicotinoids, insecticidal macrocyclic lactones, blockers of GABA-regulated chloride channels, chitin synthesis inhibitors, juvenile hormone mimetics and ligands of these receptors octopamine, agonists ecdysone, ligands, receptors ryanodine analogs nereistoxin, inhibitors mi is handrailing transport of electrons, inhibitors of the biosynthesis of lipids, cyclodiene insecticides, molting inhibitors, nucleopolyhedrovirus, subspecies of Bacillus thuringiensis encapsulated Delta endotoxin of Bacillus thuringiensis and existing in nature or genetically modified viral insecticide.

12. The composition of claim 10, where at least one additional biologically active compound or agent selected from the group comprising: abamectin, Arafat, acetamiprid, acetarsol, aldicarb, midflame, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistriflate, buprofezin, carbofuran, cartap, chinomethionat, chlorfenapyr, chlorfluazuron, chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, Chlorobenzilate, chromafenozide, clothianidin, titlemedium, cyfluthrin, beta-cyfluthrin, cigalotrin, gamma cigalotrin, lambda cigalotrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dicofol, dieldrin, dienochlor, diflubenzuron, dimefluthrin, dimethoat, dinotefuran, giovanola, emamectin, endosulfan, esfenvalerate, ethiprole, etoxazole, fenamiphos, fenazaquin, fenbutatin oxide, fanatical, fenoxycarb, fenpropathrin, fenpyroximate, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, Tau-fluvalinate, lufenuron, flufenoxuron, fonofos, halogenated, hexaflumuron, hexythiazox, hydramethylnon, they shall tziavos, Imidacloprid, indoxacarb, isofenphos, lufenuron, Malathion, metaflumizone, metaldehyde, metamidophos, methidathion, methomyl, methoprene, Methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, Fort, fozalon, phosmet, phosphamidon, pirimicarb, profenofos, perflutren, propargite, protrudent, pymetrozine, perflubron, pyrethrin, pyridaben, pyridalyl, pyriphlegethon, periphral, pyriproxifen, rotenon, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosulfat-sodium, toppenberg, tralomethrin, triazamate, trichlorfon, triflumuron, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, nucleopolyhedrovirus encapsulated Delta endotoxin of Bacillus thuringiensis, baculovirus, and entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

13. The composition according to item 12, where the at least one additional biologically active compound or agent selected from the group including abamectin, acetamiprid, amitraz, avermectin, azadirachtin, bifenthrin, buprofezin, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin, sigalot is h, lambda cigalotrin, cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, giovanola, emamectin, endosulfan, esfenvalerate, ethiprole, fanatical, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, Imidacloprid, indoxacarb, lufenuron, metaflumizone, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxifen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid, thiamethoxam, thiodicarb, thiosulfat-sodium, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis subspecies alzawal. Bacillus thuringiensis subspecies kurstaki, nucleopolyhedrovirus and the encapsulated Delta endotoxin of Bacillus thuringiensis.

14. The composition according to claim 9 in the form of a liquid composition for impregnation of the soil.

15. Sprayable composition for combating insects, containing:
(a) a biologically effective amount of a compound according to claim 1 or a composition according to claim 9; and
(b) the propellant.

16. Bait composition for combating insects, containing:
(a) a biologically effective amount of a compound according to claim 1 or a composition according to claim 9;
(b) one or more nutrients;
(c) optionally an attractant, and
(d) optionally a wetting agent.

17. Trap for insect harm the representatives, contains:
(a) bait composition according to item 16; and
(b) a housing adapted for placement baiting composition, where the housing has at least one hole, the size of which allows the insect pest to pass through the hole, causing the insect pest can gain access to the bait composition from a position outside the housing, where the housing is additionally adapted to be placed in the site or near the site of potential or known activity of the insect pest.

18. The way to deal with insect pest, comprising contacting the insect pest or its environment with a biologically effective amount of a compound according to claim 1.

19. The way to deal with insect pest, comprising contacting the insect pest or its environment with a composition according to claim 9.

20. The method according to claim 19, where the habitat is the soil, and the composition applied to the soil in the form of a composition for impregnation of the soil.

21. The way to deal with cockroaches, ants or termites, comprising contacting cockroaches, ants or termites to bait composition in the trap by 17.

22. Method of controlling mosquitoes, gnats, autumn Zhigalko, deer Slepner, Slepner, wasps, this wasp, hornets, ticks, spiders, ants or mosquitoes, comprising contacting the mosquito, the oshki, autumn of Zhigalko, deer gadfly, the gadfly, wasps, this wasp, hornet, tick, spider, ant or mosquito with a sprayable composition according to § 15 released from the aerosol container.

23. The method of protecting seeds from insect pest, comprising contacting the seed with a biologically effective amount of a compound according to claim 1.

24. The method according to item 23, where the seeds are covered with a compound according to claim 1, introduced into the composition containing film-forming or adhesive agent.

25. Treated seeds containing the compound according to claim 1 in an amount of from about 0.0001 to 1%, based on the weight of the seeds before processing.

26. The compound according to claim 1, which is selected from the group consisting of:
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-triptorelin)-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-ethyl-1-naphthaleneboronic,
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-methoxyethyl)-1-naphthaleneboronic and
4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-triptorelin)amino]ethyl]-1-naphthaleneboronic.

27. Composition for protecting an animal from a pest of containing insecticide effective amount of a compound according to claim 1 or 2, and at least one media device.

28. The composition according to item 27 in the form for oral administration.

29. Method of protecting an animal from an insect pest, comprising introducing animal insecticide effective amount of a compound according to claim 1 or 26.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing a compound of formula I: or salt thereof, where: y equals 0; R1 and R2 are taken together to form a 3-tetrahydrofuran ring; R9 is hydrogen; R10 is 5-oxazolyl; R11 is a methoxy-, ethoxy- or isopropoxy group; each V1 is independently selected from halogen, NO2, CN, OR12, OC(O)R13, OC(O)R12, OC(O)OR13, OC(O)OR12, OC(O)N(R13)2, OP(O)(OR13)2, SR13, SR12, S(O)R13, S(O)R12, SO2R13, SO2R12, SO2N(R13)2, SO2NR12R13, SO3R13, C(O)R12, C(O)OR12, C(O)R13, C(O)OR13, NC(O)C(O)R13, NC(O)C(O)R12, NC(O)C(O)OR13, NC(O)C(O)N(R13)2, C(O)N(R13)2, C(O)N(OR13)R13, C(O)N(OR13)R12, C(NOR13)R13, C(NOR13)R12, N(R13)2, NR13C(O)R12, NR13C(O)R13, NR13C(O)OR13, NR13C(O)OR12, NR13C(O)N(R13)2, NR13C(O)NR12R13, NR13SO2R13, NR13SO2R12, NR13SO2N(R13)2, NR13SO2NR12R13, N(OR13)R13, N(OR13)R12, P(O)(OR13)N(R13)2 and P(O)(OR13)2; where each R12 is a monocyclic or bicyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 4 heteroatoms selected from N, O or S, and where CH2 lying next to said N, O or S can be substituted with C(O); and each R12 optionally contains up to 3 substitutes selected from R11; where each R13 is independently selected from H, (C1-C4)-straight or branched alkyl or (C2-C4)-straight or branched alkenyl; and where each R13 optionally contains a substitute which is R14; where R14 is a monocyclic or bicyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 4 heteroatoms selected from N, O or S, and where CH2 lying next to said N, O or S can be substituted with C(O); and each R14 optionally contains up to 2 substitutes independently selected from H, (C1-C4)-straight or branched alkyl or (C2-C4)-straight or branched alkenyl, 1,2-methylenedioxy-, 1,2-ethylenedioxy group or (CH2)n-Z; where Z is selected from halogen, CN, NO2, CF3, OCF3, OH, S(C1-C4)alkyl, SO(C1-C4)alkyl, SO2(C1-C4)alkyl, NH2, NH(C1-C4)-alkyl, M((C1-C4)alkyl)2, COOH, C(O)O(C1-C4)alkyl or O(C1-C4)-alkyl; and where any carbon atom in any R13 is optionally substituted with O, S, SO, SO2, NH or N(C1-C4)alkyl; where said method includes a step for reacting a compound of formula II with a compound of formula III in a polar or nonpolar aprotic, virtually anhydrous solvent or mixture thereof, and optionally in an acceptable base selected from an organic base, inorganic base or a combination of an organic base and an inorganic base; and while heating the reaction mixture to temperature ranging from approximately 30°C to approximately 180°C for approximately 1 to 48 hours in a virtually inert atmosphere: where: LG is -OR16; where R16 is -(C1-C6)-straight or branched alkyl; -(C2-C6)-straight or branched alkenyl or alkynyl; or a monocyclic ring system consisting of 5-6 members in each ring, where said ring system optionally contains up to 3 heteroatoms selected from N, O or S, and each R16 optionally contains up to 5 substitutes independently selected from (C1-C4)-straight or branched alkyl, (C2-C4)-straight or branched alkenyl or (CH2)n-Z; n equals 0, 1, 2, 3 or 4; V1, y, Z, R1, R2, R9, R10 and R11 are as indicated above; and provided that R16 is not a halogen-substituted (C2-C3)-straight alkyl.

EFFECT: improved method.

19 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula

,

where: X is a nitrogen or carbon atom; Ar is phenyl or a heteroaromatic ring selected from pyrazolyl, furanyl, thiophenyl and isoxazolyl; R1 is hydrogen, halogen, CN or (C1-C4)alkyl; R2 is halogen or (C1-C3)alkoxy optionally fluorinated with 1-3 fluorine atoms; R3 and R5 independently denote hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkenyl or hydroxymethyl; R4 is hydrogen, halogen, optionally fluorinated (C1-C4)alkoxy or aryl(C1-C4)alkoxy; R6 is hydrogen, optionally fluorinated (C1-C4)alkyl; each R7 independenlty denotes hydrogen, halogen, optionally fluorinated (C1-C4)alkyl or (C1-C4)alkoxy optionally fluorinated with 1-3 fluorine atoms; or pharmaceutically acceptable acid addition salts thereof. The invention also relates to use of compounds of formula (I) in a pharmaceutical composition and when preparing a medicinal agent meant for treatment, the aim of which is to change the secondary signal activity level after activation of glucocorticoid receptors.

EFFECT: compounds of formula I for changing the secondary signal activity level after activation of glucocorticoid receptors.

7 cl, 5 dwg, 49 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula I or pharmaceutically acceptable salts thereof, which have receptor tyrosine kinase type I inhibiting properties and can be used in treating hyperproliferative disorders in mammals. In general formula

,

A is O or S; G is N; B is a 6-member aryl or 5-6-member heteroaryl ring containing a sulphur atom as a heteroatom; E is

, , , , , X is N or CH; D1, D2 and D3 independently denote N or CR19; D4 and D5 independently denote N or CR19 and D6 is O, S or NR20, where at least one of D4 and D5 is CR19; D7, D8, D9 and D10 independently denote N or CR19, where at least one of D7, D8, D9 and D10 is N; R1 is H or C1-C6 alkyl; each R2 independently denotes halogen, cyano, nitro etc, trifluoromethyl, difluoromethyl, fluoromethyl, fluoromethoxy, difluoromethoxy, trifluoromethoxy, azido, -SR18, -OR15, -C(O)R15, -C(O)OR15, -NR14C(O)OR18, -OC(O)R15, -NR14SO2R18, -SO2NR15R14, -NR14C(O)R15, -C(O)NR15R14, -NR15C(O)NR15R14, -NR13C(NCN)NR15R14, -NR15R14, C1-C12alkyl, C2-C12 alkenyl, alkynyl, saturated or partially unsaturated C3-C10cycloalkyl, C3-C10cycloalkyl-C1-C12alkyl, -S(O)p(C1-C6alkyl), -S(O)p(CR13R14)q-phenyl, phenyl, phenyl-C1-3-alkyl, 5-6-member heteroaryl, 5-6-member heteroaryl-C1-C3-alkyl, saturated or partially unsaturated 3-8-member heterocyclyl, 5-6-member heterocyclyl-C1-C3-alkyl, -O(CR13R14)q-phenyl, NR15(CR13R14)q-phenyl, O(CR13R14)q-(5-6-member heteroaryl), NR13(CR13R14)q-(5-6-member heteroaryl, -O(CR13R14)q-(3-8-member heterocyclyl) or -NR15(CR13R14)q-3-8-member heterocyclyl), each R3 denotes Z, where Z is selected from and , W is O or S; W2 is O or S;V is CR8R9, R8b is H or C1-C6alkyl; each of R6, R8, R8a and R9 independently denotes hydrogen, trifluoromethyl, C1-C12alkyl etc.

EFFECT: improved properties and high efficiency of using the compounds.

25 cl, 13 dwg, 1 tbl, 36 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel imidazole derivatives of general formula I and pharmaceutically acceptable salts thereof, where R1 is selected from a group comprising aryl and alkyl, optionally substituted hydroxy; R2 is selected from a group comprising hydrogen and alkyl; R3 is selected from a group comprising hydrogen and -X-A, where X is selected from a group comprising -C(O)- and -S(O)2-; and A is selected from a group comprising hydrogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocycle and optionally substituted cycloalkyl, where the optionally substituted groups are substituted with 1-2 substitutes selected from a group comprising alkyl, substituted alkyl, alkoxy, substituted amine which is a -NRR group, substituted aryloxy, heteroaryl, heterocycle, halogen, hydroxy and -S(O)2-R9, where R9 is an alkyl; or R1 and R3 together with a carbon atom bonded to R1 and a nitrogen atom bonded to R3 form a heterocyclic or substituted heterocyclic group; R4 is selected from a group comprising hydrogen, linear alkyl, -alkylene-aminoacyl-, -alkylene-hydroxy-, -[alkylene]p-nitrogen-containing heterocycle, -[alkylene]p-nitrogen-containing substituted heterocycle, -[alkylene]p-nitrogen-containing heteroaryl, -[alkylene]p-nitrogen-containing substituted heteroaryl and -[alkylene]p-NR10R11, where p equals 0 or 1, the alkylene contains 1-5 carbon atoms and can have 1 or 2 substitutes selected from a group comprising amine, hydroxy and halogen, aminoacyl relates to a group -C(O)NRR, where each R is independently selected from a group comprising hydrogen and alkyl, R10 and R11 are independently selected from a group comprising hydrogen, alkyl, substituted alkyl, -S(O)2-alkyl, substituted aryl, substituted heteroaryl, cycloalkyl, or when R10 is hydrogen, R11 is hydroxy, alkoxy or substituted alkoxy; or when R1 and R3 together with carbon and nitrogen atoms respectively bonded to them do not form a heterocyclic or a substituted heterocyclic group, R3 and R4 together with a nitrogen atom to which they are bonded form a spiro-condensed heterocyclic group; R5 is selected from a group comprising L-A1, where L is selected from a group comprising C1-C5alkylene, where the alkylene is defined above; and A1 is selected from a group comprising aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycle; and one of R6 or R7 is selected from a group comprising aryl and heteroaryl, each of which can optionally be substituted with -(R8)m, where m equals a whole number from 1 to 2, and the other of R6 or R7 is selected from a group comprising hydrogen, halogen and alkyl; or R6 as well as R7 denotes hydrogen; R8 is selected from a group comprising cyano, alkyl, -CF3, alkoxy, halogen, where alkyl, aryl, aryloxy, cycloalkyl, heterocycle, heteraryl and substituted alkyl, aryl, aryloxy, cycloalkyl, heterocycle and heteroaryl are described in claim 1. The invention also relates to specific compounds, a pharmaceutical composition based on the compound of formula I, a method of inhibiting KSP and use of the composition to prepare a medicinal agent.

EFFECT: novel imidazole derivatives are useful as kinesin spindle protein inhibitors for treating cancer.

25 cl, 27 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to drugs and concerns a combination for tumour cell growth inhibition containing a cytotoxic compound selected from camptothecin compounds; metabolic antagonists; periwinkle alkaloids; taxanes; platinum compounds; topoisomerase 2 inhibitors; and a combination of two or more said types, or a signal transfer inhibitor selected from antibodies a target of which is EGFR receptor; tyrosine kinase EGFR inhibitors; from antibodies a target of which is a VEGF/VEGF receptor system; PDGFR inhibitors; Raf inhibitors and PKB transfer inhibitors in an effective amount and a compound of formula (IV).

, where R1, R2, R11, T, U and g have the values specified in formula.

EFFECT: what is offered is a pharmaceutical composition, a method for tumour cell growth inhibition, a method of treating a malignant growth in a patient and application of the combination for preparing a drug; the new effective combinations for tumour cell growth inhibition are presented.

77 cl, 20 dwg, 7 tbl, 257 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula

,

where R1 is selected from formulae

, and ,

n equals 0; R6 and R7 are independently selected from hydrogen, C1-C6alkyl, cyanoC1-C6alkyl, C3-C6cycloalkylC0-C4alkyl and C6arylC0-C4alkyl; or R6 and R7 together with a carbon atom to which they are bonded form a 6-member heterocycloalkyl with one nitrogen atom; wherein any alkyl in R6 and R7 can optionally contain a methylene group substituted with an O atom; wherein any aryl in R6 and R7 or formed by a combination of R6 and R7 can be optionally substituted with one radical independently selected from: halide, C1-C6alkyl, -XC(O)OR10; where X denotes a bond; R10 is independently selected from C1-C6alkyl; R8 is selected from C5-C9heteroarylC0-C4alkyl containing 2-3 heteroatoms independently selected from N, O and S; wherein any heteroaryl in R8 can be optionally substituted with one radical independently selected from: halide, C1-C6alkyl, C3-C6cycloalkyl; R2 denotes hydrogen; R3 and R4 are independently selected from hydrogen, C1-C6alkyl, C3-C6cycloalkylC0-C4alkyl and C6arylC0-C4alkyl; wherein any alkyl in R3 and R4 can optionally contain a methylene group substituted with a S(O)2 group; R5 is selected from C5-C6heterocycloalkyl with 1-2 heteroatoms selected from N and O, and NR12R13; where R12 and R13 are independently selected from C1-C6alkyl; as well as pharmaceutically acceptable salts and isomers thereof. The invention also relates to use of compounds of formula (I) in preparing a medicinal agent, and to a pharmaceutical composition having cathepsin S inhibiting properties, which contains a therapeutically effective amount of the compound of formula (I) in combination with a pharmaceutically acceptable filler.

EFFECT: obtaining compounds which can be used as cathepsin S inhibitors.

10 cl, 12 dwg, 2 tbl, 9 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new compounds of formula (I) and to their pharmaceutically acceptable salts exhibiting P2X3 receptor antagonist activity. In formula (I), X represents -O-; Y represents -NRdRe where one of radicals Rd and Re means hydrogen, and the other means hydrogen; C1-C12alkyl; C5-C7cycloalkyl; C5-C7cycloalky-C1-C12alkyl; hydroxy-C1-C12alkyl; acetyl; aminocarbonyloxy- C1-C12alkyl or heterocyclyl representing a 6-members saturated ring containing heteroatom S substituted by two oxo groups; D represents optional oxygen; R1 represents isopropyl; R2 represents hydrogen; R5 represents hydrogen or C1-C12alkyl; R4 means hydrogen; C1-C12alkyl; halogen; halogen- C1-C12alkyl; C1-C12alkoxy; hydroxy; halogen- C1-C12alkoxy; nitro; amino; hydroxy- C1-C12alkyl; C1-C12alkoxyalkyl; hydroxy- C1-C12alkoxy; C1-C12alkylsulphonyl; cyano; heteroaryl representing a 5-members aromatic ring containing one, two or three heteroatoms selected from O, S and N which can be optionally substituted by a thio group, C1-C12alkyl or C1-C12alkylsulphonyl; heterocyclyl representing a 6-members saturated ring containing two heteroatoms N, one of which is substituted C1-C12alkylsulphonyl; -(CH2)m-(Z)n-(CO)-Rf or -(CH2)m-(Z)n-SO2-(NRg)n-Rf where each m and n independently represents 0 or 1, Z means NR8, Rf means C1-C12alkyl, hydroxy, amino or hydroxy- C1-C12alkyl, and Rg means hydrogen; R3 represents methoxy; R6 represents hydrogen; and one of radicals R7 and R8 represents hydrogen, and the other represents hydrogen, acetyl or phenyl.

EFFECT: also, the invention refers to a pharmaceutical composition and to an application of the compound of formula (I) for preparing a drug.

8 cl, 3 tbl, 70 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel oxadiazole compounds of formula (1) and pharmaceutically acceptable salts thereof, where R1 and R2 assume values given in the description, Y is a single bond. The invention also relates to use of said compounds as DGAT1 inhibitors, for example for treating obesity and diabetes, and a method of inhibiting.

EFFECT: high treatment efficiency.

13 cl, 65 tbl, 712 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula , where R1 is a 3-7-member carbocyclic ring and n is a number ranging from 1 to 8, and the rest of the radicals are described in the claim.

EFFECT: possibility of using such compounds and compositions in therapy as metabotropic glutamate receptor modulators.

33 cl, 367 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of general formula

where there are R3/R3', R4/R4' and R5/R5' where at least one of either R4/R4' or R5/R5' always represents a fluorine atom, and the other radical values are disclosed in the description.

EFFECT: making the compounds which are γ-secretase inhibitors, and can be effective in treating Alzheimer's disease or advanced cancers, including but not limited to carcinoma of uterine cervix and breast carcinoma and malignant tumours of hematopoietic system.

15 cl, 3 tbl, 18 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: claimed invention relates to compounds of formula (IC-2), to their pharmaceutically acceptable salts, N- oxides or solvates. In formula (IC-2) Z represents carbomoyl group, which can be replaced with C1-4 alkyl or hydroxy; R1 represents C1-8 alkyl or C1-8 alkoxy; R4 and R4-1 each independently represent hydrogen atom or C1-8 alkyl; m represents integer number from 1 to 5, when m equals 2 or larger number, all R1 can have same or different values. Invention also relates to compounds, representing 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-napthlenyl}methyl)-3-azetidinecarbonic acid, 1-({6-[(4-isobutyl-2-methoxybenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalinyl}methyl)-3- azetidinecarbonic acid and other, given in formula of claimed invention.

EFFECT: obtaining pharmaceutical composition, which has agonistic activity with respect to EDG-1, EDG-6 and/or EDG-8, containing as active component invention compound, to method of prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8 invention compounds, to method of prevention and/or treatment of disseminated sclerosis and method of immune reaction suppression and/or induction of lymphopenia, to application of invention compounds for obtaining medication for prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8, to application of compounds for obtaining medication for prevention and/or treatment of disseminated sclerosis, to application of compounds for obtaining immunodepresant and/or medication inducing lymphopenia and to crystal forms of some individual compounds.

17 cl, 10 dwg, 5 tbl, 251 ex

FIELD: chemistry.

SUBSTANCE: invention relates to substituted oxadiazole derivatives of general formula , where X denotes CH, CH2, CH=CH, CH2CH2, CH2CH=CH or CH2CH2CH2, R1 denotes an unsubstituted or mono- or disubstituted phenyl or pyrrolyl residue or an unsubstituted or mono- or disubstituted phenyl connected through a C1-C3alkyl or a thienyl or indolyl residue, where the said substitutes are selected from a group comprising F, Cl, Br, OCF3, O-C1-C6alkyl or C1-C6alkyl, R2 denotes an unsubstituted or mono- or disubstituted phenyl or thienyl residue or an unsubstituted or mono- or disubstituted phenyl residue connected through a C1-C3alkyl, where the said substitutes are selected from a group comprising F, Cl, and R3 and R4 denote a saturated straight C1-C6alkyl in form of a racemate, diastereomers, mixture of enantiomers and/or diastereomers, or a specific diastereomer, bases and/or salts with physiologically compatible acids. The invention also relates to a method of producing said compounds and a medicinal agent based on said compounds and having affinity to the µ-opioid receptor.

EFFECT: obtaining novel compounds and a medicinal agent based on said compounds, which can be used in medicine to pain killing and for treating depression, enuresis, diarrhoea, skin itching, alcohol and drug abuse, drug induced addiction, aspontaneity or for anxiolyis.

11 cl, 2 tbl, 331 ex

FIELD: chemistry.

SUBSTANCE: described are novel benzofuroxanes of general formula

, where R is phenylamino-, N-[4-methoxyphenyl]amino-, N-piperidyl-, which have fungicidal and bactericidal activity and which can be used in veterinary, medicine and agriculture.

EFFECT: high efficiency of the compositions.

2 cl, 2 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel 3,4-dihydrobenzoxazine compounds of general formula [1] (where X denotes a nitrogen atom or CR3; R1 denotes a hydrogen atom or a halogen atom; R2 denotes a C1-6alkoxy group which can be substituted with 1-5 identical or different substitutes selected from a halogen atom and a hydroxyl group; and R3 denotes a halogen atom. However, R1 denotes a halogen atom when X denotes CR3). Said compounds are effective when treating diseases where activity of vanilloid receptors subtype 1 (VR1) is involved, e.g. pain.

EFFECT: more efficient use of pharmaceutical compositions based on said compounds, more effective treatment or pain killing.

19 cl, 4 tbl, 10 ex

FIELD: chemistry.

SUBSTANCE: disclosed compounds have activity and selectivity towards the GABA A receptor subunit α5. In formula I , R1 denotes hydrogen, halogen, phenyl, a 6-member heterocycyl with 2 heteroatoms selected from N, O, a 5-member heteroaryl with 1-2 heteroatoms selected from S, N, cyano, lower alkyl, -(CH2)n-C3-C7-cycloalkyl, -(CH2)n-N(R)2, -(CH2)n-O-lower alkyl or -(CH2)n-OH; equals 0, 1 or 2; R denotes hydrogen or lower alkyl; R2 denotes C3-C7-cycloalkyl, phenyl, 5-6-member heteroaryl with 1 heteroatom selected from N, S or a 9-10-member bicyclic heteroaryl with 1-3 heteroatoms selected from N, which are possibly substituted with one or more substitutes selected from a group comprising halogen, cyano, nitro, oxo group, lower alkyl, lower alkyl substituted with a halogen, lower alkoxy, lower alkoxy substituted with a halogen, -C(O)O-lower alkyl, lower alkylsulphonyl, -NRaRb, -C(O)-NRaRb, -C(O)-(6-member heterocyclyl with 2 heteroatoms selected from N, O), benzyloxy, 6-member heterocyclyl with 1-2 heteroatoms selected from N, S, O, possibly substituted with hydroxy, 1-2 oxo-groups, halogen or lower alkyl, or selected from a 5-6-member heteroaryl with 1-3 heteroatoms selected from N, possibly substituted with lower alkyl; Ra and Rb independently denote hydrogen, lower alkylsulphonyl, -C(O)H, -(CH2)n-N(R)2, -(CH2)n-O-lower alkyl, -(CH2)n-S-lower alkyl, -(CH2)n-S(O)2-lower alkyl, (5-member heteroaryl with 1 heteroatom selected from S)-sulphonyl, lower alkyl, -(CH2)n-(5-6-member heterocyclyl with 1 heteroatom selected from O, N), possibly substituted with lower alkyl, oxo group, or denotes -(CH2)n-C3-C7-cycloalkyl, -(CH2)n-(5-6-member heteroaryl with 1-2 heteroatoms selected from N), possibly substituted with an oxo group, -(CH2)n-OH, -(CO)-R', where R' denotes C3-C7-cycloalkyl, a 5-member heteroaryl with 1 heteroatom selected from S, or lower alkyl; R' denotes a phenyl or a 6-member heteroaryl with 1 heteroatom selected from N which are possibly substituted with a halogen or lower alkyl, optionally substituted with a halogen. The invention also relates to a medicinal agent containing one or more compounds of formula I and use of the disclosed compounds to prepare a medicinal agent.

EFFECT: high effectiveness of derivatives.

16 cl, 145 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof , where D denotes phenyl; n equals 0; A, B and Q denote hydrogen; Z is selected from a group comprising a bond, straight C1-3alkylene; R1 is selected from a group comprising hydrogen, C1-10alkyl, C3-8cycloalkyl, benzyl, a 6-member monocyclic, 9-10-member bicyclic aromatic carbon-containing ring system and a spiro-ring system of formula (V): where X1 and X3 denote O; and where the said alkyl, cycloalkyl or benzyl from the R1 group is optionally substituted with 1-3 substitutes selected from a group comprising C1-3alkyl, cyano, phenyl, wherein the said phenyl is optionally substituted with 1-3 substitutes selected from halogen. The invention also relates to compounds of formulae .

Values of radicals of the said compounds are given in the claim. The invention also relates to a pharmaceutical composition having ORL1 receptor or µ opioid receptor inhibiting properties, containing an effective amount of the disclosed compound, a method of curing pain and a method of modulating pharmacological response from the opioid receptor, including the ORL1 or µ opioid receptor.

EFFECT: improved method.

41 cl, 5 tbl, 16 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula as well as separate enantiomers, diastereomers, racemic mixures and pharmaceutically acceptable salts thereof, having mitotic kinesin KSP inhibiting activity, as well as inhibitory action on tumour cells, use thereof in preparing a medicinal agent and a pharmaceutical composition based on said compounds. In said formula, R denotes Z-NR2R3, Z-OH, Ar1 and Ar2 independently denote a phenyl which, if needed, is substituted with one or more groups independently selected from: F, CI, Br, I, OH, Z denotes an alkylene having 1-6 carbon atoms which, if needed, is substituted with C1-6alkyl, and R1 assumes values given in the claim.

EFFECT: improved method.

16 cl, 3 dwg, 124 ex

Iap inhibitors // 2425838

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula

, which can inhibit binding of protein Smac with apoptosis protein inhibitor (IAP).

EFFECT: improved properties of the inhibitor.

4 cl, 198 ex

Heterocompound // 2425832

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula

or pharmaceutically acceptable salt thereof, where symbols assume the following values; ring denotes

or , X denotes a single bond, -CH2-, -NR3-, -O-, -S-, R1 denotes a halogen; phenyl; pyridyl; (C3-C8)cycloalkyl; or (C1-C6) alkyl or (C2-C6) alkenyl, each of which can contain a halogen, -CONH2, phenyl or (C3-C8)cycloalkyl as a substitute, R2 denotes CN, -O-(C1-C6)alkyl, -C(=O)H, halogen; or (C1-C6)alkyl, which can be substituted with a halogen or -OH, R3 can form morpholino or 1-pyrrolidinyl together with R1 and nitrogen, and when X denotes a single bond, R1 and R2 can jointly form a 5-member ring and additionally contain -(C1-C6)alkyl as a substitute, R4 denotes the following ring: , , , , , , , , , , or , where any one of the bonds in the ring is linked to an oxazole ring, R5 denotes -H, (C1-C6)alkyl, which can be substituted by not less than one group selected from: -C(=O)NRXRY, -NHRX and -ORX- (C2-C6)alkenyl-; -C(=O)H; -C(=O)NRXRY, RX and RY can be identical or different and denote -H; or (C1-C6)alkyl. The invention also relates to a pharmaceutical composition based on said compounds, having SlP1 agonist activity.

EFFECT: compounds and compositions can be used in medicine for preventing and treating rejection during organ transplant, bone marrow or tissue transplant and autoimmune diseases.

16 cl, 84 tbl, 198 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to aryl-isoxazole-4-yl-imidazole derivatives of formula I and to their pharmaceutically acceptable acid addition salts. The compounds of the present invention exhibit GABA A α5 receptor binding site activity and selectivity. In general formula I

each of R1-R3 independently represents hydrogen atom or halogen atom; R4 represents hydrogen atom, lower alkyl, C3-C7cycloalkyl, -(CH2)n-O-lower alkyl or hydroxy substituted lowest alkyl; R5 represents -(CH2)m-phenyl or -(CH2)m-(5-6-members heteroaryl with 1-2 heteroatoms independently seected from N, O) which optionally substituted by one or more substitutes selected from a group consisting of halogen atom, cyano, nitro, lower alkyl, lower alkoxy, lower alkylsulphanyl, lower alkyl substituted by halogen atom, -C(O)-lower alkyl, -C(O)-O-lower alkyl, -NH-C(O)-O-lower alkyl or -C(O)-NH-R' where R' represents the lower alkynyl or hydroxy substituted lower alkyl, or represents -(CH2)n-C3-C7-cycloalkyl, -(CH2)n-(6-members heterocyclyl with 1-2 heteroatoms selected from N, O), -(CH2)n-(5-6-members heteroaryl with 1-2 heteroatoms selected from N, O) or -(CH2)n-phenyl optionally substituted by halogen atom; R6 represents hydrogen atom, -C(O)H, -(CH2)n-O-lower alkyl, -C(O)O-lower alkyl, lower alkyl substituted by hydroxy or halogen atom, or represents C3-C7-cycloalkyl, phenyl, or represents -(CH2)n-O-CH2-phenyl optionally substituted by halogen atom or lower alkyl, or represents -(CH2)n-O-CH2-(6-members heteroaryl with 1 heteroatom selected from N) optionally substituted by lower alkyl or lower alkyl substituted by halogen atoms, or represents -(CH2)n-NH-(CH2)o-(6-members heterocyclyl with 2 heteroatoms selected from N; n means 0, 1, 2 or 3; m means 0 or 1; o means 1, 2 or 3.

EFFECT: presented preparation of a drug containing one or more compound of formula I and application of the compounds for preparing the drug.

31 cl, 168 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: claimed invention relates to compounds of formula (IC-2), to their pharmaceutically acceptable salts, N- oxides or solvates. In formula (IC-2) Z represents carbomoyl group, which can be replaced with C1-4 alkyl or hydroxy; R1 represents C1-8 alkyl or C1-8 alkoxy; R4 and R4-1 each independently represent hydrogen atom or C1-8 alkyl; m represents integer number from 1 to 5, when m equals 2 or larger number, all R1 can have same or different values. Invention also relates to compounds, representing 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-napthlenyl}methyl)-3-azetidinecarbonic acid, 1-({6-[(4-isobutyl-2-methoxybenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalinyl}methyl)-3- azetidinecarbonic acid and other, given in formula of claimed invention.

EFFECT: obtaining pharmaceutical composition, which has agonistic activity with respect to EDG-1, EDG-6 and/or EDG-8, containing as active component invention compound, to method of prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8 invention compounds, to method of prevention and/or treatment of disseminated sclerosis and method of immune reaction suppression and/or induction of lymphopenia, to application of invention compounds for obtaining medication for prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8, to application of compounds for obtaining medication for prevention and/or treatment of disseminated sclerosis, to application of compounds for obtaining immunodepresant and/or medication inducing lymphopenia and to crystal forms of some individual compounds.

17 cl, 10 dwg, 5 tbl, 251 ex

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