Insecticide anthranylamides


FIELD: organic chemistry, insecticides.

SUBSTANCE: invention relates to compounds of the formula (1) , their N-oxides and salts that can be used in agriculture wherein values A, B, J, R1, R3, R4 and n are given in the invention claim. Also, invention describes a method for control of arthropoda pests to provides high productivity that comprises applying the effective dose of compound of the formula (1) on arthropoda pests and in medium of their habitation, and a the composition with arthropocide activity comprising compounds of the formula (1).

EFFECT: valuable properties of compounds and composition.

23 cl, 34 tbl, 759 ex

 

The level of technology

This invention relates to certain anthranilamide, their N-oxides suitable for use in agriculture salts and compositions, and methods for their use as arthropodicides as in agriculture, and in areas not related to agronomy.

Control of arthropod pests is essential to achieve high yields. Damage arthropods growing and stored crops, can lead to significant performance degradation and, consequently, to increased costs for the consumer. Also important is the control of arthropod pests in forestry, greenhouse crops, ornamental crops, nurseries, when stored food and fiber products for the health of livestock, Pets, animals in captivity, and wild animals. Many of the products used for this purpose are commercially available, but there is a need for new compounds that are more effective, less expensive, less toxic, safe for the environment and act in a different way.

In NL 9202078 described derivatives of N-allinternational acid of formula i used as insecticide.

where, among other things,

X is PR is my bond;

Y is N or C1-C6by alkyl;

Z is NH2, NH (C1-C3by alkyl) or N (C1-C3by alkyl)2; and

R1-R9independently are H, halogen, C1-C6the alkyl, phenyl, hydroxy, C1-C6alkoxy or C1-C7acyloxy.

Brief description of the invention

This invention relates to a method of control of arthropods, including the processing of arthropods or their environment arthropodicides effective amount of the compounds of formula 1, its N-oxide or acceptable for use in agriculture salts

where

A and b each independently are O or S;

each J is independently phenyl or naftilos group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6;

or each J is independently a 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring or ring system optionally substituted from 1 to 4 R7;

n is from 1 to 4;

R1is H; or C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil or C3-C6cycloalkyl, each of which is optionally substituted by one or more mandated what teli, selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C4alkoxycarbonyl, C1-C4alkylamino, C2-C8dialkylamino and C3-C6cyclooctylamino; or

R1is C2-C6alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or C(=A)J;

R2is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C6alkoxycarbonyl or C2-C6alkylcarboxylic;

R3is N; G; C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group comprising halogen, G, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C6al is oxycarbonyl, C2-C6alkylsulphonyl and C3-C6trialkylsilyl, or phenyl, phenoxy or 5 - or 6-membered heteroaromatic ring, each optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C6cycloalkyl, C1-C4halogenated, C2-C4halogenoalkanes, C2-C4halogenoalkanes, C3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C3-C6(alkyl) cyclooctylamino, C2-C4alkylsulphonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or C3-C6trialkylsilyl; C1-C4alkoxy, C1-C4alkylamino; C2-C8dialkylamino; C3-C6cyclooctylamino; C2-C6alkoxycarbonyl or C2-C6alkylcarboxylic; or

R2and R3taken together with the nitrogen atom to which they are attached, form a ring containing the E. from 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, where the specified ring may be optionally substituted from 1 to 4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy;

G is a 5 - or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally incorporating one or more ring members selected from the group comprising C(=O), SO or S(O)2and optionally substituted from 1 to 4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy;

each R4independently is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C6halogenation, C2-C6halogenation, C2-C6halogenoalkanes, C3-C6halogencyclization, halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino or C3-C6t is alkylsilane; or

each R4independently is phenyl, benzyl or phenoxy, each of which is optionally substituted C1-C4the alkyl, C2-C4alkenyl, C2-C4the quinil, C3-C6cycloalkyl, C1-C4halogenation, C2-C4halogenation, C2-C4halogenoalkanes, C3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C3-C6(alkyl)cyclooctylamino, C2-C4alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R5independently is C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C6halogenation, C2-C6halogenation, C2-C6halogenoalkanes, C3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C6alkoxy, C1-C6halog is alkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6allogenicity, C1-C6halogenatedsolvents, C1-C6halogenated.sulphonated, C1-C6alkylamino, C2-C12dialkylamino or C3-C6cyclooctylamino, C2-C6alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl, C3-C6trialkylsilyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-;

each R6independently is H, halogen, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C4alkoxy or C2-C4alkoxycarbonyl; or

each R6independently is phenyl, benzyl, phenoxy, 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl, C2-C4alkyne is, C3-C6cycloalkyl, C1-C4halogenated, C2-C4halogenoalkanes, C2-C4halogenoalkanes, C3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C3-C6(alkyl) cyclooctylamino, C2-C4alkylsulphonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or C3-C6trialkylsilyl;

each R7independently is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C6halogenation, C2-C6halogenation, C2-C6halogenoalkanes, C3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C6alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenallylacetic the Ohm, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C6alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl, C3-C6trialkylsilyl; or

each R7independently is phenyl, benzyl, benzoyl, phenoxy, 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C6cycloalkyl, C1-C4halogenated, C2-C4halogenoalkanes, C2-C4halogenoalkanes, C3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C3-C6(alkyl)cyclooctylamino, C2-C4alkylsulphonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8/sub> dialkylaminoalkyl or C3-C6trialkylsilyl;

provided that

(1) if a and b are both O, R2is H or C1-C3the alkyl, R3is N or C1-C3the alkyl and R4is H, halogen, C1-C6the alkyl, phenyl, hydroxy, or C1-C6alkoxy, one of R5different from halogen, C1-C6of alkyl, hydroxy, or C1-C6alkoxy; or

(2) J is different from optionally substituted 1,2,3-thiadiazole.

This invention also relates to compounds of formula 1, their N-oxides and suitable for use in agriculture salts

where

A and b each independently are O or S;

each J is independently phenyl or naftilos group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6;

or each J is independently a 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring or ring system optionally substituted from 1 to 4 R7;

n is from 1 to 4;

R1is H; or C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil or C3-C6cycloalkyl, each of which is optionally C is substituted by one or more substituents, selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C4alkoxycarbonyl, C1-C4alkylamino, C2-C8dialkylamino and C3-C6cyclooctylamino; or

R1is C2-C6alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or C(=A)J;

R2is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C6alkoxycarbonyl or C2-C6alkylcarboxylic;

R3is H; C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C6Alcock carbonyl, C2-C6alkylsulphonyl and C3-C6trialkylsilyl, or proximalto, optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl, C2-C4quinil, C3-C6cycloalkyl, C1-C4halogenated, C2-C4halogenoalkanes, C2-C4halogenoalkanes, C3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C3-C6(alkyl) cyclooctylamino, C2-C4alkylsulphonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C8dialkylaminoalkyl or C3-C6trialkylsilyl; C1-C4alkoxy, C1-C4alkylamino; C2-C8dialkylamino; C3-C6cyclooctylamino; C2-C6alkoxycarbonyl or C2-C6alkylcarboxylic; or

R2and R3taken together with the nitrogen atom to which they are attached, form a ring containing 2 to 6 atoms of carbon and optionally one additional the volume of nitrogen, sulfur or oxygen, where the specified ring may be optionally substituted by 1-4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy;

each R4independently is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C6halogenation, C2-C6halogenation, C2-C6halogenoalkanes, C3-C6halogencyclization, halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity,1-C4halogenatedsolvents,1-C4halogenated.sulphonated,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino or3-C6trialkylsilyl; or

each R4independently is phenyl, benzyl or phenoxy, each of which is optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes, 3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R5independently is C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization,1-C4halogenoalkane, C1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity, C1-C4halogenatedsolvents,1-C4halogenated.sulphonated, CN, NO2With1-C4alkoxycarbonyl,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl or3-C8dialkylamino is carbonyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-;

each R6independently is H, halogen, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl,1-C4alkoxy or2-C4alkoxycarbonyl; or

each R6independently is phenyl, benzyl, phenoxy, 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring optionally substituted with one to three substituents, independently selected from the group comprising From1-C4alkyl, C2-C4alkenyl,2-C4quinil,3-C6cycloalkyl,1-C4halogenated,2-C4halogenoalkanes,2-C4halogenoalkanes,3-C6halogenosilanes, halogen, CN, NO2With1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4 alkylsulphonyl, C2-C4alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R7independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity,1-C4halogenatedsolvents,1-C4halogenated.sulphonated,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R7independently is phenyl, benzyl, benzoyl, phenoxy, 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed hemeroby ilicakoy ring system, where each ring optionally substituted with one to three substituents, independently selected from the group comprising From1-C4alkyl, C2-C4alkenyl,2-C4quinil,3-C6cycloalkyl,1-C4halogenated,2-C4halogenoalkanes,2-C4halogenoalkanes,3-C6halogenosilanes, halogen, CN, NO2With1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylsulphonyl,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

provided that

(i) at least one R4and at least one R7different from N;

(ii) J is different from optionally substituted 1,2,3-thiadiazole;

(iii) if J is an optionally substituted pyridine and R2is H, R3different from N or CH3;

(iv) if J is an optionally substituted pyridine, R7cannot be CONH2With2-C6alkylaminocarbonyl or3-C8 dialkylaminoalkyl;

(v) if J is an optionally substituted pyrazole, tetrazole or pyrimidine, R2and R3can't both be hydrogen.

This invention also relates to arthropodicides compositions comprising arthropodicides effective amount of the compounds of formula 1 and at least one additional component selected from the group comprising surfactants, solid diluents and liquid diluents.

Detailed description of the invention

In the above descriptions, the term "alkyl", used either as a separate word or as parts of words, such as "alkylthio" or "halogenated"includes alkyl straight or branched chain such as methyl, ethyl, n-propyl, isopropyl or the different butyl isomers, pentile or exile. The term "1-2 alkyl" means that one or two available positions for this substituent may be alkyl. "Alkenyl" means alkenes with a straight or branched chain, such as 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 alkynes with a straight or branched chain, such as 1-PROPYNYL, 2-PROPYNYL and the different isomers of butenyl, pentenyl and hexenyl. "Quinil" can also include groups, with the present of multiple triple relations, such as 2,5-hexadienyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy and various isomers of butoxy, pentox, hexyloxy. "Alkoxyalkyl" means alkyl, substituted alkoxy. Examples of "alkoxyalkyl" include CH3Och2CH3Och2CH2CH3CH2OCH2CH3CH2CH2CH2OCH2and CH3CH2OCH2CH2. "Alkylthio" includes straight and branched groups alkylthio, such as methylthio, ethylthio and various isomers of property, butylthio, pentylthio and hexylthio. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "heterocyclic ring" or "heterocyclic ring system" means a ring or rings, in which at least one atom of the ring is carbon and which contains from 1 to 4 heteroatoms, independently selected from the group comprising nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogen atoms, not more than 2 oxygen atoms and not more than 2 sulfur atoms. The heterocyclic ring can be attached through any available carbon atom or nitrogen by replacement of a hydrogen on the specified carbon or nitrogen. The term "aromatic ring system" denotes fully unsaturated carbocycle, heterotic is s, in which the polycyclic ring system is aromatic (where aromatic" indicates that this system of rings is the rule of aromaticity of hukkala). The term "heteroaromatic ring" means a fully aromatic ring in which at least one atom of the ring is carbon and which include from 1 to 4 heteroatoms, independently selected from the group comprising nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogen atoms, not more than 2 oxygen atoms and not more than 2 sulfur atoms (where "aromatic" indicates that this system of rings is the rule of aromaticity of hukkala). The heterocyclic ring can be attached through any available carbon atom or nitrogen by replacement of a hydrogen on the specified carbon or nitrogen. The term "aromatic heterocyclic ring system" includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic" indicates that this system of rings is the rule of aromaticity of hukkala). The term "condensed heterobicyclic ring system" includes ring system consisting of two condensed rings, in which at least one atom to which ICA is not a carbon and can be aromatic or not aromatic, such as defined above.

The term "halogen"used as a separate word, or words, such as "halogenated"includes fluorine, chlorine, bromine or iodine. Further, when used in words such as "halogenated"specified alkyl may be partially or completely replaced by halogen atoms that can be the same or different. Examples of "halogenoalkane" include F3With ClCH2, CF3CH2and CF3CCl2. The terms "halogenoalkanes", "halogenoalkanes", "halogenoalkane" and the like are defined analogously to the term "halogenated". Examples of "halogenoalkane include (Cl)2C=SNSN2and CF3CH2SN=SNSN2. Examples of "halogenoalkane include the NA≡CCHCl, CF3With≡C, CCl3With≡and FCH2C≡CCH2. Examples of "halogenoalkane" include CF3Oh, CCl3CH2Oh, HCF2CH2CH2O and CF3CH2O.

The total number of carbon atoms in the Deputy designated by the prefix "Ci-Cj"where i and j are numbers from 1 to 6. For example, C1-C3alkylsulfonyl covers deputies from methylsulfonyl to propylsulfonyl; C2alkoxyalkyl means of CH3Och2;3alkoxyalkyl means, for example, CH3CH(och3), CH3Och3CH2or CH3CH2Och2; and (C4alcox the alkyl refers to the various isomers of an alkyl group, replaced by alkoxygroup containing in total 4 carbon atoms, examples include CH3CH2CH2Och2and CH3CH2OCH2CH2. In the above descriptions, when the compound of formula 1 contains a heterocyclic ring, all the substituents attached to the ring via any available carbon atom or nitrogen by replacement of the hydrogen at the specified carbon or nitrogen.

If the group contains a Deputy, which can be hydrogen, for example, R3then, if the Deputy is hydrogen, it is clear that such a group is unsubstituted.

Compounds in accordance with this invention can exist as one or more stereoisomers. Different stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Specialist in the art it is clear that one stereoisomer may be more active and/or may have a favorable effect, if it is enriched, compared to the other stereoisomer(s), or when it is separated from the other stereoisomer(s). In addition, specialists in the art will know how to separate, enrich, and/or to selectively receive said stereoisomers. Therefore, the compounds in accordance with this invention may be present in the form of a mixture with stereozoom the ditch, individual stereoisomers or in the form of optically active forms.

This invention comprises compounds selected from formula 1, N-oxides and acceptable in agriculture salts. Specialist in the art it will be clear that not all heterocycles containing nitrogen, can form N-oxides, as it requires an available lone pair of electrons on nitrogen atom to its oxidation to the oxide; the specialist in the art may recognize heterocycles containing nitrogen, which can form N-oxides. Specialist in the art also knows that tertiary amines can form N-oxides. Methods of synthesis used to obtain the N-oxides of heterocycles and tertiary amines are well known to experts in the art and include the oxidation of heterocycles and tertiary amines with nagkakamali, such as peracetic and m-chloroperbenzoic acid (MSRA), hydrogen peroxide, alkylhydroperoxides, such as tert-butylhydroperoxide, perborate sodium and dioxirane, such as dimethyldioxirane. These methods obtain the N-oxides are widely described and discussed in the literature, for example, in T.L. Gilchrist Comprehensive Organic Synthesis, Vol.7, str-750, S.V. Ley, Ed., Pergamon Press; M. Tišler and B. Stanovnik Comprehensive Heterocyclic Chemistry, Vol.3, p.18-19, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene Advances in Heterocyclic Chemistry, Vol.43, p.139-151, .R. Katritzky, Ed., Academic Press; M. Tišler and B. Stanovnik Advances in Heterocyclic Chemistry, Vol.9, str-291, A.R. Katritzky and A.J. Boulton, Eds., Academic Press; and G.W.H. Cheeseman and E.S.G. Werstiuk Advances in Heterocyclic Chemistry, Vol.22, str-392, A.R. Katritzky and A.J.Boulton, Eds., Academic Press.

Salts of compounds in accordance with this invention include acid additive salts with inorganic or organic acids such as Hydrobromic, chloride-hydrogen, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluensulfonate or valeric acid.

Preferred specific compounds of formula II

where X and Y are O;

m is from 1 to 5;

n is from 1 to 4;

R1is H; or C1-C6the alkyl, C2-C6alkenyl,3-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl, C2-C4alkoxycarbonyl,1-C4alkylamino,2-C8dialkylamino and C3-C6cyclooctylamino; or

R1is3-C6alquiler what anilam, With2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl or3-C8dialkylaminoalkyl;

R2is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkoxycarbonyl or2-C6alkylcarboxylic;

R3is isopropyl or tert-bootrom; and

each R4and R5independently are H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity,1-C4halogenatedsolvents,1-C4halogenated.sulphonated,1-C4alkoxycarbonyl,1-C4alkylamino,2-C8dialkylamino,3-C6 cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R4and R5independently are phenyl, optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2With1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4alkoxycarbonyl,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl.

Also preferred are methods of control of arthropods, including the processing of arthropods or their environment arthropodicides effective amount with the unity of formula II and its insecticidal composition.

Also preferred are the compounds of formula III

where

A and b each independently are O or S;

J is a phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6; or 5 - or 6-membered heteroaromatic ring, optionally substituted from 1 to 4 R7;

n is from 1 to 4;

R1is H; or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl, C2-C4alkoxycarbonyl,1-C4alkylamino,2-C8dialkylamino and C3-C6cyclooctylamino; or

R1is2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl or3-C8dialkylaminoalkyl;

R2is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl,1-C4alkoxy, C1-C4alkylamino,2-C 8dialkylamino,3-C6cyclooctylamino,2-C6alkoxycarbonyl or2-C6alkylcarboxylic;

R3is H; or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio,1-C4alkylsulfonyl and C1-C4alkylsulfonyl; or

R2and R3taken 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 of nitrogen, sulfur or oxygen, where the specified ring may be optionally substituted by 1-4 substituents selected from the group comprising From1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy;

each R4independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity,1-C4halogenatedsolvents,1-C4halogenated.sulphonated,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R4independently is phenyl, benzyl or phenoxy, each of which is optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2With1-C4alkoxy, C1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkitab the sludge, With2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R3independently is C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization,1-C4halogenoalkane,1-C4alkylthio,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4allogenicity,1-C4halogenatedsolvents,1-C4halogenated.sulphonated, CN, NO2With1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl or3-C8dialkylaminoalkyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-;

each R6independently is H, halogen, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C4alkoxy; or

each R6independently is phenyl, benzyl or Fenox is optionally substituted C 1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes, C3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino, C3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R7independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1/sub> -C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R7independently is phenyl, benzyl, phenoxy, optionally substituted C1-C4the alkyl, C3-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, C2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6

Also preferred are methods of control of arthropods, including the processing of arthropods or their environment arthropodicides effective amount of the compounds of formula III and its insecticidal composition.

Also preferred are the compounds of formula IV

where

A and b each independently are O or S;

each J is a phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6or 5 - or 6-membered heteroaromatic ring, optionally substituted from 1 to 4 R7;

n is from 1 to 4;

R1is H; or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C2-C4alkoxycarbonyl, C1-C4alkylamino, C2-C8dialkylamino and C3-C6cyclooctylamino; or

R1is C2-C6alkylcarboxylic, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl or C3-C8dialkylamino what bonila;

R2is H, C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkylamino, C2-C8dialkylamino, C3-C6cyclooctylamino, C2-C6alkoxycarbonyl or C2-C6alkylcarboxylic;

R3is H; C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil,3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, NO2, hydroxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl and C1-C4alkylsulfonyl; C1-C4alkoxy, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkoxycarbonyl or2-C6alkylcarboxylic; or

R2and R3taken 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 of nitrogen, sulfur or oxygen, where the specified ring may be optionally substituted by 1-4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-Csub> 2alkoxy;

each R4independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, C1-C4alkylamino, C2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R4independently is phenyl, benzyl or phenoxy, each of which is optionally substituted C1-C4the alkyl, C2-C4alkenyl, C2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6 halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R5independently is C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6Alki is carbonyl, With2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-;

each R6independently is H, halogen, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C4alkoxy; or

each R6independently is phenyl, benzyl, phenoxy or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6 alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

each R7independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes,3-C6halogencyclization, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,2-C6alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or

each R7independently is phenyl, benzyl, benzoyl, phenoxy or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkene the Ohm, With2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl;

provided that if a and b are both O, R2is N or C1-C3the alkyl, R3is N or C1-C3the alkyl and R4is H, halogen, C1-C6the alkyl, phenyl, hydroxy, or C1-C6alkoxy, one of R5different from halogen, C1-C6of alkyl, hydroxy, or C1-C6alkoxy.

Also preferred are methods of control of arthropods, including the processing of arthropods or their environment arthropodicides effective amount of the compounds of formula IV and its insecticidal HDMI is on.

Preferred from the standpoint of activity are the following:

A preferred group 1. Ways, including the compounds of formula 1 where J is a phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6.

A preferred group 2. The methods included in the preferred group 1, in which

A and b both are About;

n is from 1 to 2;

R1is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,2-C6alkylcarboxylic or2-C6alkoxycarbonyl;

R2is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,2-C6alkylcarboxylic or2-C6alkoxycarbonyl;

R3is C1-C6the alkyl, C2-C6alkenyl, C2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio, C1-C2alkylsulfonyl and C1-C2alkylsulfonyl;

one of the groups R4attached to the phenyl ring in position 2 or position 5, and the decree is fair R 4is C1-C4the alkyl, C1-C4halogenation, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents or C1-C4halogenated.sulphonated;

each R5independently is C1-C4halogenation, CN, NO2C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated or C2-C4alkoxycarbonyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-; and

each R6independently is H, halogen, C1-C4the alkyl, C1-C2alkoxy or C2-C4alkoxycarbonyl; or

each R6independently is phenyl or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6 cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl.

A preferred group 3. The methods included in the preferred group 2, in which

R1and R2both are N;

R3is C1-C4the alkyl, optionally substituted with halogen, CN, och3, S(O)pCHC;

each R4independently is N, CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen;

each R5independently is CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2The co2CF3, OCF2CHF2, S(O)pCH2CFCor S (O)pCF2CHF2;

each R6 independently is H, halogen or stands; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN; and

p is 0, 1 or 2.

A preferred group 4. The methods included in the preferred group 3, in which R3is isopropyl or tert-bootrom.

A preferred group 5. Ways, including the compounds of formula 1 where J is a 5 - or 6-membered heteroaromatic ring, optionally substituted from 1 to 4 R7.

A preferred group of 6. The methods included in the preferred group 5, in which

J is a 5 - or 6-membered heteroaromatic ring selected from the group including J-1, J-2, J-3, J-4 and J-5, where each J is optionally substituted from 1 to 3 R7.

Q is O, S or NR7; and

W, X, Y and Z are independently N or CR7provided that in J-4 and J-5, at least one of W, X, Y and Z is n

A preferred group of 7. The methods included in the preferred group 6, in which

A and b are About;

n is from 1 to 2;

R1is H, C1-C4al the sludge, C2-C4alkenyl, C2-C4the quinil, C2-C6alkylcarboxylic or C2-C6alkoxycarbonyl;

R2is H, C1-C4the alkyl, C2-C4alkenyl, C2-C4the quinil,3-C6cycloalkyl,2-C6alkylcarboxylic or C2-C6alkoxycarbonyl;

R3is H; or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio, C1-C2alkylsulfonyl and C1-C2alkylsulfonyl;

one of the groups R4attached to the phenyl ring in position 2, and the specified R4is C1-C4the alkyl, C1-C4halogenation, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents or C1-C4halogenated.sulphonated; and

each R7independently is H, C1-C4the alkyl, C1-C4halogenic the scrap, halogen, CN, NO2C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated or2-C4alkoxycarbonyl; or phenyl or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl.

A preferred group of 8. The methods included in the preferred group 7, in which

J the choice is up from the group, include pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazol and isoxazol, each of which is optionally substituted from 1 to 3 R7.

A preferred group 9. The methods included in the preferred group 8, in which

J is chosen from the group comprising pyridine, pyrimidine, pyrazole, thiophene and thiazole, each of which is optionally substituted from 1 to 3 R7.

R1and R2both are N;

R3is C1-C4the alkyl, optionally substituted with halogen, CN, och3, S(O)pCHC;

each R4independently is N, CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen;

each R7independently is H, halogen, CH3, CF3, OCHF2, S(O)pCF3, S(O)pCHF2The co2CF3, OCF2CHF2, S(O)pCH2CF3, S(O)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each of which is optionally substituted C1-C4the alkyl, C1-C4halogenation, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, halogen or CN; and

p is 0, 1 or 2.

Site is citicolina group 10. The methods included in the preferred group 9, in which J is pyridine, optionally substituted from 1 to 3 R7.

A preferred group 11. The methods included in the preferred group 10, in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group of 12. The methods included in the preferred group 10, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group 13. The methods included in the preferred group 9, in which J is a pyrimidine, optionally substituted from 1 to 3 R7.

A preferred group 14. The methods included in the preferred group 13 in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group of 15. The methods included in the preferred group 13 in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen is whether CN.

A preferred group 16. The methods included in the preferred group 9, in which J is a pyrazole, optionally substituted from 1 to 3 R7.

A preferred group 17. The methods included in the preferred group 16, in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group 18. The methods included in the preferred group 16, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group 19. The methods included in the preferred group 18, in which R7is pyridine, optionally substituted C1-C4the alkyl, C1-C4, halogenation, halogen or CN.

Most preferred are methods that include the compounds of formula 1 selected from the group including:

3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamid,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,

1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(t is iformity)-1H-pyrazole-5-carboxamide,

1-(2-forfinal)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carboxyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and

3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.

Preferred from the standpoint of activity and/or ease of synthesis are the following connections:

A preferred group A. the compounds of formula 1 where J is a phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6.

A preferred group C. the preferred Compounds of group a, in which

A and b both are About;

n is from 1 to 2;

R1is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,2-C6alkylcarboxylic or2-C6alkoxycarbonyl;

R2is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl,2-C6alkylcarboxylic or2With 6alkoxycarbonyl;

R3is C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio, C1-C2alkylsulfonyl and C1-C2alkylsulfonyl;

one of the groups R4attached to the phenyl ring in position 2 or position 5, and the specified R4is C1-C4the alkyl, C1-C4halogenation, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents or C1-C4halogenated.sulphonated;

each R5independently is C1-C4halogenation, CN, NO2C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated or2-C4alkoxycarbonyl; or

(R5)2that process is United to the adjacent carbon atoms, can be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-; and

each R6independently is H, halogen, C1-C4the alkyl, C1-C2alkoxy or2-C4alkoxycarbonyl; or

each R6independently is phenyl or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation,2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl.

A preferred group C. the preferred Compounds of group b, in which

R1and R2both are N;

R3is C1/sub> -C4the alkyl, optionally substituted with halogen, CN, och3, S(O)pCH3;

each R4independently is N, CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen;

each R5independently is CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2The co2CF3, OCF2CHF2, S(O)pCH2CF3or S(O)pCF2CHF2;

each R6independently is H, halogen or stands; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN; and

p is 0, 1 or 2.

A preferred group D. Connection preferred group, in which R3is isopropyl or tert-bootrom.

The preferred group, I.e. Compounds of formula 1, in which J is a 5 - or 6-membered heteroaromatic ring, optionally substituted from 1 to 4 R7.

A preferred group F. the preferred Compounds of group E, which

J is a 5 - or 6-membered heteroaromatic ring selected from the group including J-1, J-2, J-3, J-4 and J-5, where each J is optionally substituted from 1 to 3 R7.

Q is O, S or NR7; and

W, X, Y and Z are independently N or CR7provided that in J-4 and J-5, at least one of W, X, Y or Z is N.

A preferred group G. the preferred Compounds of group F, which

A and b are About;

n is from 1 to 2;

R1is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,2-C6alkylcarboxylic or2-C6alkoxycarbonyl;

R2is H, C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C2-C6alkylcarboxylic or2-C6alkoxycarbonyl;

R3is H; or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio, C1-C2alkylsulfonyl and C1-C2alkylsulfonyl;

one of the groups R4attached to the phenyl ring in position 2, and the specified R4is C1-C4the alkyl, C1-C42C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents or C1-C4halogenated.sulphonated; and

each R7independently is H, C1-C4the alkyl, C1-C4halogenation, halogen, CN, NO2C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated or2-C4alkoxycarbonyl; or phenyl or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil,3-C6cycloalkyl, C1-C4halogenation,2-C4halogenation, C2-C4halogenoalkanes,3-C6halogencyclization, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino is, With2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylcarboxylic,2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl.

A preferred group N. The preferred compounds of the group G, in which

J is chosen from the group comprising pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazol and isoxazol, each of which is optionally substituted from 1 to 3 R7.

A preferred group I. preferred Compounds of group H, in which

J is chosen from the group comprising pyridine, pyrimidine, pyrazole, thiophene and thiazole, each of which is optionally substituted from 1 to 3 R7.

R1and R2both are N;

R3is C1-C4the alkyl, optionally substituted with halogen, CN, och3, S(O)pCH3;

each R4independently is N, CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen;

each R7independently is H, halogen, CH3, CF3, OCHF2, S(O)pCF3, S(O)pCHF2The co2CF3, OCF2CHF2, S(O)pCH2CF3, S(O)p CF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each of which is optionally substituted C1-C4the alkyl, C1-C4halogenation, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, halogen or CN; and

p is 0, 1 or 2.

A preferred group J: preferred Compounds of group I in which J is pyridine, optionally substituted from 1 to 3 R7.

The preferred group To: preferred Compounds of group J, in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group L. the preferred Compounds of group J, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group M preferred Compounds of group I, where J is a pyrimidine, optionally substituted from 1 to 3 R7.

A preferred group N. the preferred Compounds of group M in which R7is phenyl, the optional samewe the s ' C 1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group O. the preferred Compounds of group M in which R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group R. the preferred Compounds of group I, where J is a pyrazole, optionally substituted from 1 to 3 R7.

A preferred group Q. Connections preferred group R, in which R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

A preferred group R. the preferred Compounds of group R, in which R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

The preferred group is S. compounds of preferred groups R, in which R7is pyridine, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

Most preferred are the compounds of formula 1 selected from the group including:

3-IU the Il-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamid,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,

1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(2-forfinal)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and

3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.

The preferred compositions are compositions containing the compounds of formula 1, are listed in preferred groups 1-19, and particularly preferred compounds of the above.

As noted above, each J is independently phenyl group or naftilos group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6; or each J is independently a 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, where the each ring or ring system optionally substituted from 1 to 4 R 7. The term "optionally substituted" applied to the data of the J groups refers to groups that are not substituted or having at least one non-hydrogen Deputy, which do not reduce arthropodicides action possessed by the unsubstituted analog. It is also noted that J-1 - J-5, above, are 5 - or 6-membered heteroaromatic rings. Examples of phenyl substituted from 1 to 2 R5and optionally substituted from 1 to 3 R6is the ring, represented as J-6 in the demo example 1, where m is an integer from 1 to 2 and q is an integer from 1 to 3. It is noted that at least one of R5must be present in J-6. Although the structure J-6 shows R6groups, their presence is not necessary, since they are optional substituents. Example naftilos group, a substituted from 1 to 2 R5and optionally substituted from 1 to 3 R6is J-59, presented in demo 1, where m is an integer from 1 to 2 and q is an integer from 1 to 3. It is noted that at least one of R5must be present in J-59. Although the structure of J-59 shows R6groups, their presence is not necessary, since they are optional substituents. Examples of 5 - or 6-membered heteroaromatic ring, optionally substituted on the 1 to 4 R 7include rings J-7 - J-58 presented in the demonstration example 1, where r is an integer from 1 to 4. It is noted that J-7 - J-26 are examples of J-1, J-27 J-41 are examples of J-2, J-42 J-44 are examples of J-3, J-46 J-53 are examples of J-4 and J-54 J-58 are examples of J-5. The nitrogen atoms that require substitution to fill their valence, substituted R7. It is noted that some of the J groups can be substituted only less than 4 R7groups (for example, J-19, J-20, J-23 J-26 J-37 J-40 can be replaced by only one R7). Examples of aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring systems, optionally substituted from 1 to 4 R7are J-60 J-90 presented in the demonstration example 1, where r is an integer from 1 to 4. Although the structures J-7 - J-58 and J-60 J-90 shows R7groups, their presence is not necessary, since they are optional substituents. It is noted that if R5, R6and/or R7are the H attached to any atom, this is equivalent to the fact that the atom is not substituted. It is noted that when the attachment point between (R5)m, (R6)qor (R7)rand J group is shown as "floating", (R5)m, (R6)qor (R7)rcan be attached to any available carbon atom J g is PI. It is noted that if the connection point J of the group is shown as "floating", J group can be attached to the remainder of formula 1 through any available carbon atom J group by substitution of a hydrogen atom.

Demo 1

As noted above, G is a 5 - or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two of the substituent in the ring selected from the group comprising C(=O), SO or S(O)2and optionally substituted by 1-4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy. The term "optionally substituted" applied to the data G groups refers to groups that are not substituted or having at least one non-hydrogen Deputy, which does not reduce arthropodicides action possessed by the unsubstituted analog. It is noted that if the connection point G groups are shown as "floating", the group G may be attached to the remainder of formula 1 through any available carbon atom G group by substitution of a hydrogen atom. Optional substituents may be attached to any available carbon atom by substitution of a hydrogen atom. Examples of 5 - or 6-membered nonaromatic the carbocyclic rings, group G include rings represented as G-1 through G-8 demonstration in example 2, where these rings are optionally substituted by 1-4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy. Examples of 5 - or 6-membered non-aromatic heterocyclic ring group G include rings represented as G-9 - G-48 demo example 2, where these rings are optionally substituted by 1-4 substituents selected from the group comprising C1-C2alkyl, halogen, CN, NO2and C1-C2alkoxy. It is noted that if G contains a ring selected from G-31 through G-34, G-37 and G-38, Q1selected from O, S or N. it is Noted that if G is a G-11, G-13, G-14, G-16, G-23, G-24, G-30 - G-34, G-37 and G-38 and Q1is N, the nitrogen atom may satisfy its valence by substitution with either H or C1-C2the alkyl.

Demo 2

or

As noted above, each R6and each R7can be independently (among others) a 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl,2-C4quinil,3-C6cycloalkyl, C1-C4halogenated,2-C4halogenoalkanes,2-C4ha is hohenecken, With3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6cyclooctylamino,3-C6(alkyl)cyclooctylamino,2-C4alkylsulphonyl,2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl. Examples of such R6and R7groups include the ring or ring system, represented as a ring J-7 - J-58 and J-60 J-90 in the demonstration example 1, except that such rings are optionally substituted by 1-3 substituents selected from the group comprising C1-C4alkyl, C2-C4alkenyl,2-C4quinil,3-C6cycloalkyl, C1-C4halogenated,2-C4halogenoalkanes,2-C4halogenoalkanes,3-C6halogenosilanes, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4alkylamino,2-C8dialkylamino,3-C6C is calciumin, With3-C6(alkyl)cyclooctylamino,2-C4alkylsulphonyl,2-C6alkoxycarbonyl,2-C6alkylaminocarbonyl,3-C8dialkylaminoalkyl or3-C6trialkylsilyl and not (R7)r. It is noted that such substituents can be attached to any available carbon atom J group by substitution of a hydrogen atom. It is noted that, if the connection point J of the group is shown as "floating", J group can be attached to the remainder of formula 1 through any available carbon atom J group by substitution of a hydrogen atom.

To obtain compounds of formula 1 can be used one or more methods and options, such as described in schemes 1-17. Determine a, b, J, R1, R2, R3, R4, R3, R6, R7, m and n in the compounds of formula 1-34 below, such as given above in the brief description of the invention. Compounds of formulas 1A-C, 2-b, 4A-g, 5A-b are variants of the compounds of formulas 1, 2, 4, and 5.

The compounds of formula 1 can be obtained by methods described in schemes 1-17. A typical method presented in scheme 1 and involves a combination of anthranilamide formula 2 with an acid chloride of formula 3 in the presence of an acid acceptor to obtain the compounds of formula 1A. Typical acid acceptors include amine bases, such as Tr is ethylamine, diisopropylethylamine and pyridine; other acid acceptors include hydroxides such as sodium hydroxide and potassium, and carbonates such as sodium carbonate and potassium carbonate. In certain cases it is preferable to use the acid acceptors for polymer substrates, such as associated with the polymer diisopropylethylamine and associated with the polymer dimethylaminopyridine. At the next stage amides of formula 1A can be converted to thioamides of formula 1b using a variety of standard reagents vectors of tigraphy, including pentasulfide phosphorus and reagent Losson.

Scheme 1

An alternative method of preparing compounds of formula 1A is a combination of anthranilamide formula 2 with an acid of formula 4 in the presence of a dehydrating agent, such as dicyclohexylcarbodiimide (DCC). This method is also used reagents on a polymeric substrate, such as associated with the polymer cyclohexylcarbodiimide. The synthesis methods presented in schemes 1 and 2 are only illustrative examples of methods of preparing compounds of formula 1, as in the literature devoted to the synthesis described many reactions of this type.

Scheme 2

Specialist in the art it is clear that the acid chlorides of the formula is 3 can be obtained from the acids of formula 4 by many well-known methods.

Anthranilamide formula 2A are usually obtained from the corresponding 2-nitrobenzamide formula 5 by the catalytic hydrogenation of the nitro group. Typical methods include the reduction with hydrogen in the presence of a metal catalyst such as palladium on coal or platinum oxide, and hydroxyl solvents, such as ethanol and isopropanol. These methods are widely described in the chemical literature. R1substituents, such as alkyl, substituted alkyl and the like, basically can be introduced at this stage by using known methods, including either direct alkylation or usually the preferred method of reductive alkylation of amine. The most commonly used method is the interaction of aniline 2A with an aldehyde in the presence of a reducing agent, such as Lamborgini sodium obtaining compounds of formula 2b, in which R1is alkyl, alkenyl, quinil or their substituted derivatives.

Scheme 3

Intermediate amides of formula 5A is easily obtained from commercially available 2-nitrobenzoic acids. Here can be applied typical methods of formation of the amide. They include direct dehydrating combination of acids of formula 6 with amines of formula 7 using, for example, DCC, and the conversion of the acid into an activated form, such is AK the acid chlorides or anhydrides, and further combination with amines to obtain amides of formula 5A. It was found that ethylchloride is especially useful reagent for this type of reactions involving the activation of acid. In the chemical literature widely describes this type of reactions. Amides of formula 5A can easily turn into thioamides of formula 5b using commercially available reagents vectors of tigraphy, such as pentasulfide phosphorus and reagent Losson.

Scheme 4

Benzoic acid of formula 4 (J is an optionally substituted phenyl) are generally well known in the art, as well as methods for their preparation. One particularly useful subspecies of benzoic acid in accordance with this invention is 2-methyl-4-performantly acid of formula 4A (R5is, for example, CF3With2F5With2F7). The synthesis of these compounds are presented in schemes 5 through 9. Benzoic acid of formula 4A can be obtained from benzonitrile formula 8 by hydrolysis. The conditions used may include the use of a base such as a hydroxide or alkoxide of an alkali metal (e.g. potassium hydroxide or sodium), in a solvent such as water, ethanol or a glycol (e.g., J.Chem. Soc. 1948, 1025). Alternatively, the hydrolysis may be carried out using acids such the AK sulfuric acid or phosphoric acid, in a suitable solvent such as water (for example, Org. Synth. 1955, Coll vol.3, 557). The choice of conditions depends on the stability of R5under the reaction conditions, and usually to achieve this kind of transformation is used elevated temperature.

Scheme 5

The NITRILES of formula 8 may be obtained from anilines of formula 9 classical sequence, including the diazotization and treatment of the intermediate diazonium salts with copper cyanide (for example, J. Amer. Chem. Soc. 1902, 24, 1035).

Scheme 6

Anilines of formula 9 can be obtained from compounds of formula 10. This transformation can be achieved by a well-known method, which uses the Raney-Nickel (Org. Synth. Coil. Vol. VI, 581). Alternatively, the same transformation can be achieved by use of a suitable catalyst, such as palladium, in the presence of hydrogen. The reaction is usually carried out at a pressure from 102up to 105kPa in a suitable organic solvent, such as, but not limited to, toluene. Elevated temperatures, such as 80-110°usually required to achieve transformation. Specialist in the art it is clear that there are many possible chemical modifications thioester group, which can be used to facilitate this transformation.

Therefore the 7

The compounds of formula 10 can be obtained from aminosulfonyl formula 11. The transformation can be performed in proton solvent such as methanol or water, in an aprotic solvent such as dichloromethane or toluene, in the presence of a suitable base, such as triethylamine (e.g., Org. Synth. Coll. Vol. VI, 581) or sodium methoxide, or in a mixture of proton solvent, aprotic solvent and a base. The temperature at which carry out the reaction generally ranges from 40 to 110°C. skilled in the art will understand that can also be used suitable salts of the compounds of formula 11, such as, but not limited to, hydrochloride, sulfate or bisulfate, provided that you first use the appropriate amount of base to obtain the free base 11. It can be conducted as a separate phase or as an integral part of the stage, including the conversion of compounds of formula 11 in the compounds of formula 10.

Scheme 8

The compounds of formula 11 can be obtained from anilines of formula 12 by reaction with dimethyl sulfide and appropriate gloriouse agent such as, but not limited to, N-chlorosuccinimide (for example, Org. Synth. Coll. Vol. VI, 581), chlorine or N-chlorobenzotriazole. Alternatively, anilines of formula 12 can be processed dimethyl what sulfoxide, which was activated by the processing agent such as acetic anhydride, triperoxonane anhydride, triftormetilfullerenov, cyclohexylcarbodiimide, sulfur trioxide or pentoxide phosphorus. The reaction is carried out in a suitable organic solvent, such as dichloromethane or dimethyl sulfoxide. The reaction is carried out at a temperature of from -70°to 25°S, which depends on the used solvent and reagent.

Scheme 9

Intermediate anthranilamide formulas 2A and 2b can also be obtained from isataevich anhydrides of formulas 13 and 14 (Scheme 10). A typical method involves the reaction of equimolar amounts of amine 7 with sativum anhydride in polar aprotic solvents such as pyridine and dimethylformamide, at temperatures from room temperature to 100°C. R1substituents, such as alkyl and substituted alkyl, can be introduced by base catalyzed alkylation satiago anhydride 13 known alkylating reagents R1-Lg (where Lg is a leaving group such as halogen, alkyl or arylsulfonate or alkyl sulphates) to give the substituted alkyl intermediates 14. Sativae anhydrides of formula 13 can be prepared by the methods described Coppola, Synthesis 505-36 (1980).

Scheme 10

Alternate pic is b receive certain compounds of formula 1 (where a is Oh, In is O and R1is H) includes the interaction of amine 7 with benzoxazinones formula 15. Typical methods include the reaction of the amine with benzoxazinones in solvents such as tetrahydrofuran or pyridine, at temperatures from room temperature to the boiling point of the solvent under reflux. Benzoxazinone widely described in the chemical literature and are available using known methods, which include a combination of entrylevel acid or satiago anhydride with an acid chloride. References on the synthesis and chemistry benzoxazinones can be found in Jakobsen et al., Biorganic and Medicinal Chemistry, 2000, 8, 2095-2103 and here the links. See also Coppola, J.Heterocyclic Chemistry, 1999, 36, 563-588.

Scheme 11

Heterocyclic acids 4, in which J is an optionally substituted heterocycle, can be prepared by the methods described in schemes 12-17. Both shared and private links to a wide range of heterocyclic acids, including tifany, furans, pyridine, pyrimidines, triazoles, imidazoles, pyrazoles, thiazole, oksazolov, isothiazole, thiadiazole, oxadiazole, triazine, pyrazine, pyridazine and isoxazoles can be found in the following sources: Rodd's Chemistry of Chemistry of Carbon Compounds, Vol IVa-IVI., S.Coffey editor, Elsevier Scientific Publishing, New York, 1973; Comprehensive Hekerocyclic Chemistry, Vol.1-7, A.R.Katritzky and C.W.Rees editors, Pergamon Press, New York, 1984; ComprehensiveHeterocyclic Chemistry II, Vol.1-9, A.R.Katritzky, C.W.Rees and E.F.Scriven editors, Pergamon Press, New York, 1996; and in the series The Chemistry of Heterocyclic Compounds, E.C.Taylor, editor, Wiley, New York. Especially useful heterocyclic acid in accordance with this invention include pyridine acid, pyrimidine acid pyrazol acid. Methods of synthesis of representative examples of each type are described in the diagrams 12-17. Many heterocyclic acids and General methods for their synthesis can be found in the application WO 98/57397.

Synthesis characteristic pyridine acids (4b) is shown in scheme 12. This method includes the known synthesis of pyridines from β-ketoesters and 4-aminobutanol (19). Group substituents R7(a) and R7(b) include, for example, alkyl and halogenated.

Scheme 12

The typical synthesis of pyrimidine acid (4C) is shown in scheme 13. This method includes the known synthesis of pyrimidines from vinyliden-β-ketoesters (22) and amidino. Group substituents R7(a) and R7(b) include, for example, alkyl and halogenated.

Scheme 13

Synthesis characteristic pyrazol acid (4d-4g) are shown in schemes 14-17. Pyrazoles 4d described in scheme 14. The synthesis shown in scheme 14, includes, as a key stage, the introduction of R7(b) the Deputy through the alkylation of pyrazole. Alkylating agent R7(b)-Lg (where Lg is a leaving group, such as l, Br, I, sulfonates such as p-toluensulfonate or methanesulfonate, or sulfates, such as-SO2OR7(b)includes R7(b) groups, such as C1-C6alkyl, C2-C6alkenyl,2-C6quinil,3-C6cycloalkyl, C1-C6halogenated,2-C6halogenoalkanes,2-C6halogenoalkanes,3-C6halogenosilanes, C2-C6alkylsulphonyl,2-C6alkoxycarbonyl,3-C8dialkylaminoalkyl,3-C6trialkylsilyl; or phenyl, benzyl, benzoyl, 5 - or 6-membered heteroaromatic ring or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system, each ring or ring system optionally substituted. Oxidation of the methyl group gives pyrazolylborate acid. Some of the more preferred R7(a) groups include halogenated.

Scheme 14

Pyrazoles 4E described in scheme 15. Such pyrazol acid can be obtained by metallation and carboxylation pyrazoles of formula 28 as a key stage. R7(b) the group entered as described in scheme 14, i.e. through alkylation of R7(b) alkylating agent. Preferred groups R7(a) include, for example, cyano and halogenated.

the Hema 15

Pyrazoles 4f described in scheme 16. They can be obtained by the interaction of the optionally substituted phenyl 29 with 30 pyruvate with the production of esters of pyrazole 31. Hydrolysis of ester gives pyrazol acid 4f. This method is especially useful for producing compounds in which R7(b) is optionally substituted phenyl and R7(a) is halogenation.

Scheme 16

Pyrazol acid of formula 4g described in scheme 17. They can be obtained 3+2 cyclopentadiene appropriately substituted nitrilimines or substituted propiolate (33) or with acrylates (36). Cycloaddition with acrylates requires additional oxidation of the intermediate pyrazoline to the pyrazole. Hydrolysis of ester gives pyrazol acid 4g. Preferred for this reaction aminoglucoside include triptoreline (38) and kinodynamic (39). Connection, as well as 38, are known (J. Heterocycl. Chem. 1985, 22(2), 565-8). Compounds such as 39 may be obtained by known methods (Tetrahedron Letters 1999, 40, 2605). These methods are particularly preferred for producing compounds in which R7(b) is optionally substituted phenyl and R7(a) is halogenation or bromine.

Scheme 17

It is clear that some reagents and reaction conditions described above for preparing compounds of formula 1, may not be compatible with certain functional groups present in the intermediate compounds. In such cases, the introduction sequence protection/unprotect or interconversion of functional groups in the synthesis will help to obtain the desired product. The use and choice of protective groups is obvious to the expert in the field of chemistry (see, for example, Greene, T.W.; Wurs, P.G.M. Protective Groups in Organic Synthesis, 2nded.; Wiley: New York, 1991). Specialist in the art will understand that in some cases, after the introduction of a given reagent, marked on each individual scheme, it may be necessary to conduct additional standard stage of synthesis, not designated in detail to complete the synthesis of compounds of formula 1. Specialist in the art will also understand that it may be necessary to carry out several steps, shown in the above schemes in an order other than that implied described certain sequence of preparing compounds of formula 1.

Specialist in the art will also understand that all of the compounds of formula 1 and of the intermediate compounds described above, can be subjected to various electrophilic, nucleophilic, radical, metallurgy the economic, oxidative and reductive reactions to add substituents or modify existing substituents.

To keep things simple, suppose that the specialist in the art using the above description will be able to use the invention fully. The examples below are, therefore, given only to illustrate and not limit the invention in any way. The percentages given mass, except those that are used to specify the composition of mixtures of solvents for chromatography, or if not indicated otherwise. Parts and percentages to describe mixtures of solvents used in chromatography, given volume, unless otherwise indicated.1H NMR spectrum is given in ppm, down from tetramethylsilane; s - singlet, d - doublet, t - triplet, q - Quartet, m - multiplet, DD - doublet of doublets, dt - doublet of triplets, CL - broad singlet.

Example 1

Stage a: 3-methyl-N-(1-methylethyl)-2-nitrobenzamide

A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine (1.22 g, 12.1 mmol) in 25 ml of methylene chloride cooled to 10°C. Carefully add ethylchloride with the formation of a solid precipitate. After stirring for 30 minutes added Isopropylamine (0,94 g, 16.0 mmol) to give a homogeneous solution. The reaction mixture is stirred for a further 1 cha is a, poured into water and extracted with ethyl acetate. The organic extracts washed with water, dried over magnesium sulfate and evaporated under reduced pressure to get a 1.96 g of the desired intermediate as a white solid, melting at 126-128°C.

1H NMR (CDCl3) δ 1,24 (d, 6N), of 2.38 (s, 3H), 4,22 (m, 1H), 5,80 (sh, 1H), and 7.4 (m, 3H).

Stage: Obtain 2-amino-3-methyl-N-(1-methylethyl)benzamide

2-Nitrobenzamide with stage A (1.70 g, 7.6 mmol) hydronaut over 5% Pd/C in 40 ml of ethanol at 50 f/d2(345 kPa). After cessation of hydrogen absorption, the reaction mixture was filtered through celite and the celite washed with diethyl ether. The filtrate is evaporated under reduced pressure to get 1,41 g specified in the connection header in the form of a solid, melting at 149-151°C.

1H NMR (CDCl3) δ 1,24 (DD, 6N), of 2.16 (s, 3H), 4,25 (m, 1H), 5,54 (sh, 2H), 5,85 (sh, 1H), 6,59 (t, 1H), 7,13 (d, 1H), 7,17 (d, 1H).

Stage C: 3-methyl-N-(1-methylethyl)-2-[[4-

(triptoreline)benzoyl]amino]benzamide

4-(Triptoreline)benzoyl chloride (0.29 grams, 1.3 mmol) is added dropwise to a mixture of aniline from step B (0.25 g, 1.3 mmol) and triethylamine (of 0.13 g, 1.3 mmol) in 5 ml of methylene chloride at room temperature. After stirring for 1 hour the reaction mixture was poured into water and extracted with ethyl acetate. The combined extracts are dried over self is that magnesium and evaporated under reduced pressure. The obtained solid was washed with hexane/diethyl ether and filtered to obtain 0,41 g specified in the title compounds, the compounds in accordance with this invention, in the form of a solid, melting at 207-209°C.

1H NMR (CDCl3) δ 1,19 (d, 6N), of 2.33 (s, 3H), 4,15 (m, 1H), 5,97 (SHS, 1H), 7,2-7,4 (m, 6N), of 8.04 (d, 1H), 10,11 (SHS, 1H).

Example 2

Stage A: Obtain 1-Ethyl-3-cryptomaterial-5-icarbonell acid

To a mixture of 3-cryptomaterial (5 g, 37 mmol) and powdered potassium carbonate (10 g, 72 mmol), stirred in 30 ml of N,N-dimethylformamide, are added dropwise, logmean (8 g, 51 mmol). After moderate heat the reaction mixture was stirred over night at room temperature. The reaction mixture was partitioned between 100 ml of diethyl ether and 100 ml of water. The ether layer is separated, washed with water (3x) and saturated salt solution and dried over magnesium sulfate. Evaporation of the solvent in vacuo gives 4 g of oil.

To 3.8 g of the obtained oil, mixed in 40 ml of tetrahydrofuran in a nitrogen atmosphere in a bath of dry ice/acetone, are added dropwise 17 ml of 2.5 M solution of n-utility in tetrahydrofuran (43 mmol) and the solution stirred for 20 minutes at -78°C. an Excess of gaseous carbon dioxide bubbled into the stirred solution with medium speed for 10 minutes. After you add the value of carbon dioxide, the reaction mixture was slowly brought to room temperature and stirred over night. The reaction mixture was partitioned between diethyl ether (100 ml) and 0.5 N aqueous solution of sodium hydroxide (100 ml). The alkaline layer was separated and acidified with concentrated chloride-hydrogen acid to pH 2-3. The aqueous mixture is extracted with ethyl acetate (100 ml)and the organic extract washed with water and saturated salt solution and dried over magnesium sulfate. The oily residue which remains after evaporation of the solvent in vacuo, triturated to a solid with a small amount of n-butyl chloride. After filtration and drying receive slightly contaminated sample 1-ethyl-3-cryptomaterial-5-icarbonell acid (1.4 g) as a solid substance with a significant range of the melting temperature.

1H NMR (CDCl3) δ 9,85 (sh, 1H), 7.23 percent (s, 1H), and 4.68 (q, 2H)and 1.51 (t, 3H).

Stage: Obtain 2-[1-Ethyl-3-cryptomaterial-5-ylcarbonyl]-3-methyl-N-(1-methylethyl)benzamide

To a solution of 1-ethyl-3-cryptomaterial-5-icarbonell acid (0.5 g, 2.4 mmol), stirred in 20 ml of methylene chloride, add oxalicacid (1.2 ml, 14 mmol). Adding 2 drops of N,N-dimethylformamide, the formation of foam and bubbles. The reaction mixture is refluxed for 1 hour in a yellow solution. After cooling, the solvent is removed in vacuo and the resulting residue is dissolved in 20 ml of Tetra is hydrofuran. To the stirred solution was added 2-amino-3-methyl-N-(1-methylethyl)benzamide (0.7 g, 3.6 mmol), followed by adding dropwise N,N-diisopropylethylamine (3 ml, 17 mmol). After stirring at room temperature overnight, the reaction mixture is distributed between ethyl acetate (100 ml) and 1 N. aqueous chloride-hydrogen acid (75 ml). The separated organic layer is washed with water and saturated salt solution, and dried over magnesium sulfate. Evaporation in vacuo gives a solid residue, which upon purification by chromatography on a column of silica gel (2:1 hexane/ethyl acetate) gives 0.5 g specified in the title compounds, the compounds in accordance with this invention, melting at 223-226°C.

1H NMR (DMSO-D6): 10,15 (s, 1H), with 8.05 (d, 1H), 7,45 (s, 1H), 7,43-7,25 (m, 3H), 4,58 (kV, 2H), 3,97 (m, 1H), of 2.45 (s, 3H), of 1.36 (t, 3H), 1.06 a (d, 6N) ppm

Example 3

Stage A: Obtain S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]sulfinamide

A solution of N-chlorosuccinimide (12-43 g, br93.1 mmol) in ˜170 ml of dichloromethane is added to a mixture of 4-(trifluoromethyl)aniline (15 g, br93.1 mmol) and dimethyl sulfide (6,35 g, 102 mmol) in 230 ml of dichloromethane at-5-0°C. After complete addition, the mixture is stirred at 0-5°C for 1 hour, and add N-chlorosuccinimide (0.02 g, with 4.64 mmol). After another 30 minutes, the mixture is washed with 500 ml of 1 n sodium hydroxide.

The organic phase is dried and evaporated from the floor is the group product in the form of solids 19-72 g, melting at 101-103°With (after crystallization from ethyl acetate/hexane).

IR (Nujol) 1603, 1562, 1532, 1502, 1428, 1402, 1335, 1300, 1270, 1185, 1150, 1103, 1067, 1000, 972, 940, 906, 837, 817 cm-1.

1H NMR (CDCl3) δ to 7.35 (d, J=8,8 Hz, 2H), at 6.84 (d, J=8,8 Hz, 2H), to 2.67 (s, 3H).

Stage b: 2-[(methylthio)methyl]-4-(trifluoromethyl)benzolamide

The sodium methoxide in methanol (1,95 g of 9.02 mmol, 25%) are added to S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]sulfinamide from step A (2 g, 9,04 mmol) in 15 ml of toluene. The mixture is heated to ˜80°for ˜1 hour. The mixture is cooled to 25°and poured into 100 ml of water. The mixture is extracted with 2×100 ml of ethyl acetate and the combined extracts dried and evaporated to obtain 1.8 g of the product as a solid, melting at 65,5-67,5°With (after crystallization from hexane).

IR (nujol) 3419, 3333, 1629, 1584, 1512, 1440, 1334, 1302, 1235, 1193, 1139, 1098, 1078, 979, 904, 832 cm-1.

1H NMR (CDCl3) δ to 7.35 (d, J=1.5 Hz × 8,2 Hz, N), 6,72 (d, J=8,4 Hz), 4,39 (CL, 2H), 3,69 (s, 2H), 1,99 (s, 3H).

Stage With: Obtaining 2-methyl-4-(trifluoromethyl)benzenamine

Activated Raney Nickel (500 g wet paste, ˜50 μ) added in several portions to a solution of 2-[(methylthio)methyl]-4-(trifluoromethyl)benzenamine (55,3 g, 0.25 mol) in 1 l of ethanol over 30 minutes at 25-30°C. the Heterogeneous mixture was vigorously stirred for 30 minutes after adding. The stirring is stopped and the solids precipitated during the course the e one hour. The fluid is drained from the solids and pour through filter paper. The filtrate is evaporated under reduced pressure, and the residue is placed in dichloromethane. The organic phase is separated from a small amount of water, dried over magnesium sulfate and evaporated under reduced pressure to obtain 37.6 g specified in the connection header in the form of oil.

1H NMR (CDCl3) δ 7,28 (m, 2H), of 6.68 (d, 1H), a 3.87 (CL, 2H), 2,19 (s, 3H).

Stage D: Obtaining 2-methyl-4-(trifluoromethyl)benzonitrile

Concentrated chloride-hydrogen acid (16 ml) was added dropwise at an average speed to a heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzenamine (14 g, 80 mmol) and 120 ml of water with vigorous stirring. Get a thick slurry, which is stirred for 20 minutes, diluted with 280 ml of water and cooled to 5°C. a Solution of sodium nitrite (5.5 g, 80 mmol) and 25 ml of water is added slowly to the reaction suspension. After stirring for 30 minutes at 5°get the solution, which is stirred under cooling for 30 minutes and then neutralized with potassium carbonate. The resulting solution of diazonium salts are then added in several portions through the pipette to stir at 95°With a mixture of potassium cyanide (22 g, 0.34 mol), pentahydrate copper sulfate (20 g, 80 mmol) and 140 ml of water. After the addition the mixture is stirred for 30 minutes at 95°and C is the cooled to room temperature. Add diethyl ether and the heterogeneous mixture is filtered through celite. The solids washed with diethyl ether and the filtrate separated. The aqueous phase is extracted with diethyl ether, and the combined organic extracts are dried over magnesium sulfate and concentrated under reduced pressure to get to 13.1 g specified in the title compound as a brown oil.

1H NMR (CDCl3) δ 7,74 (d, 1H), 7,60 (s, 1H), 7,55 (d, 1H), 2,64 (s, 3H).

Stage E: Obtaining 2-methyl-4-triftorperasin acid

Potassium hydroxide (15.7 g, 0.28 mol) and 15 ml of water is added in the form of a solution to a stirred heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzonitrile (13 g, 70 mmol) and 135 ml of ethylene glycol. The reaction mixture is heated at 120-130°C for 20 hours and cooled to room temperature. The dark solution was poured into 800 ml of water and filtered through celite. The filtrate was washed with diethyl ether and then the aqueous solution is acidified with concentrated chloride-hydrogen acid. The resulting aqueous phase is shaken out three times with ethyl acetate, the organic extracts are combined, dried over magnesium sulfate and evaporated under reduced pressure to obtain specified in the title compound as a tan solid.

1H NMR (CDCl3) δ 7,98 (d, 1H), of 7.70 (s, 1H), 7,65 (d, 1H), 2,60 (s, 3H).

Stage F: Getting 2-ethyl-4-(triptoreline)of benzoyl chloride

Thionyl chloride (0,42 g, 3.5 mmol) are added to a solution of benzoic acid from step E (0.50 g, 2.4 mmol) in 10 ml toluene at room temperature. The reaction mixture is boiled under reflux, then cooled to room temperature. The solvent is evaporated under reduced pressure and the excess thionyl chloride is removed by azeotropic distillation with toluene. The resulting benzoyl chloride are used on stage G.

Stage G: Obtaining 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide

The benzoyl chloride from step F (0,29 g, 1.3 mmol) is added to a mixture of aniline from example 1, stage (0.36 g, 1.9 mmol) and diisopropylethylamine (0.26 g, 2.0 mmol) in 10 ml of chloroform at room temperature. The reaction mixture was stirred over night. The solid precipitate is filtered and dried to obtain 0,38 g specified in the title compounds, the compounds in accordance with this invention, melting at 247-248°C.

1H NMR (CDCl3) δ 1,24 (d, 6N), is 2.41 (s, 3H), 2,58 (s, 3H), 4,20 (m, 1H), 5,94 (sm, 1H), 7,2-7,3 (m, 2H), 7,40 (d, 1H), 7,52 (s, 1H), 7,53 (d, 1H), of 7.70 (d, 1H), 9,36 (SHS, 1H).

Example 4

Stage A: Getting 2-methyl-6-(trifluoromethyl)-3-pyridinecarboxamide

Thionyl chloride (4.35 g, of 36.5 mmol) are added to a mixture of 2-methyl-6-triftormetilfosfinov acid (of 5.00 g, 24.4 mmol) in 75 ml of toluene, and the mixture is heated under reflux for hours. The reaction mixture is cooled to room temperature, and the solvent is removed under reduced pressure. The excess thionyl chloride is removed by azeotropic distillation with toluene. The obtained acid chloride used in example 4, step C.

Stage: Getting 8-methyl-2-[2-methyl-6-(trifluoromethyl)-3-pyridinyl]-4H-3,1-benzoxazine

A mixture of 6-methylisatoic anhydride (to 3.92 g, 22,1 mmol) and acid chloride from step A (the 5.45 g, a 24.3 mmol) is heated under reflux in pyridine for 16 hours. The dark brown solution is cooled to room temperature, and the solvent is removed under reduced pressure. The excess pyridine is removed by azeotropic distillation with toluene. Add diethyl ether, and the resulting brown solid is filtered off. The solid is placed in a mixture of aqueous sodium bicarbonate and chloroform, the chloroform extracts are dried over magnesium sulfate and evaporated. The excess pyridine is removed by azeotropic distillation with toluene to obtain a 5.1 g specified in the title compound as a brown solid.

1H NMR (CDCl3) δ to 2.65 (s, 3H), 3,11 (s, 3H), 7,49 (t, 1H), 7,40 (m, 1H), 7.68 per-7,73 (m, 2H), 1,11 (d, 1H), 8,58 (d, 1H).

Stage With: Obtaining 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridine

Isopropylamine (7,37 g, 0.125 mmol) are added to a mixture of benzoxazinone from the stage (of 4.00 g, 12.5 mmol in 30 ml of tetrahydrofuran. Get a homogeneous solution. The mixture is quickly heated to obtain a dense white precipitate. The solvent is removed under reduced pressure, and the obtained solid is washed with diethyl ether and filtered to obtain 4,48 g specified in the connection header in the form of a solid, melting at 247-248°C.

1H NMR (CDCl3) δ 1,24 (d, 6N), is 2.41 (s, 3H), 2,77 (s, 3H), 4,17 (m, 1H), 5,96 (sm, 1H), 7,21 (m, 2H), 7,40 (d, 1H), 7,53 (d, 1H), of 7.97 (d, 1H), 9,80 (SHS, 1H).

Example 5

Stage A: Obtain 4-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-2-(trifluoromethyl)-5-pyrimidinecarboxylic

To a solution of 0.8 g (4 mmol) of 4-methyl-2-cryptomaterial-5-carboxylic acid [obtained by the method described Palanki et al., J. Med. Chem. 2000, 43, 3995], mixed in 15 ml of methylene chloride add oxalicacid (2 ml, 23 mmol). After adding 2 drops of N,N-dimethylformamide, the formation of foam and bubbles. The reaction mixture is refluxed for 1 hour in a yellow solution. After cooling, the solvent is removed in vacuo and the resulting residue is dissolved in 20 ml of tetrahydrofuran. To the stirred solution was added 2-amino-3-methyl-N-(1-methylethyl)benzamide (1 g, 5 mmol), followed by adding dropwise N,N-diisopropylethylamine (3 ml, 17 mmol). After stirring at room temperature overnight, the reaction mixture R is opredelyaut between ethyl acetate (200 ml) and 1 N. water chloride-hydrogen acid (75 ml). The separated organic layer is washed with water and saturated salt solution and dried over magnesium sulfate. Evaporation in vacuo gives a white solid, which is suspended in a small amount of ethyl acetate and filtered to obtain (after drying) 650 mg specified in the title compounds, the compounds in accordance with this invention, melting at 248-251°C.

1H NMR (AMCO-D6): 10,3 (s, NH), 9,07 (s, 1H), 8,25 (d, NH), 7,43-7,25 (m, 3H), a 4.03 (m, 1H), 2,73 (s, 3H), 2,32 (s, 3H), 1.12 in (d, 6N) ppm

Example 6

Stage A: Getting 2-methyl-1-phenyl-4-(trifluoromethyl)-1H-pyrazole

A solution of 1,1,1-triterpene-2,4-dione (20,0 g, 0,130 mol) in glacial acetic acid (60 ml) is cooled to 7°using bath ice/water. Added dropwise phenyl hydrazine (14.1 g, 0,130 mol) in 60 minutes. During the addition the temperature of the reaction mass rises to 15°C. the Obtained orange solution stand at ambient conditions for 60 minutes. Acetic acid is removed by evaporation on a rotary evaporator with a bath temperature of 65°C. the Residue is dissolved in methylene chloride (150 ml). The solution was washed with aqueous sodium bicarbonate (3 g in 50 ml water). Purple-red organic layer is separated, treated with activated charcoal (2 g) and MgSO4, then filtered. Volatile compounds are removed in the rotor of the second evaporator. The crude product is a mixture of 28.0 g butter pink colour that has ˜89% of the desired product and 11% of 1-phenyl-5-(trifluoromethyl)-3-methylpyrazole.

1H NMR (DMSO-D6) δ to 2.35 (s, 3H), 6,76 (s, 1H), and 7.6-7.5 (m, 5H).

Stage: Obtain 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

A sample of crude 1-phenyl-3-(trifluoromethyl)-5-methylpyrazole (˜89%, 50.0 g, 0,221 mol) is mixed with water (400 ml) and cetyltrimethylammoniumbromide (4,00 g to 0.011 mol). The mixture is heated to 95°C. Add potassium permanganate 10 equal portions, separated ˜8-minute intervals. The temperature of the reaction mass while adding support at the level of 95-100°C. After adding the last portion of the mixture was incubated for ˜15 minutes at 95-100°during which disappears purple color characteristic of the permanganate. The reaction mixture is filtered hot (˜75° (C) through a layer of Celite® thickness 1 cm to 150 ml of the large glass beads. The filter was washed with warm (˜50° (C) water (3×100 ml). The combined filtrate and washings extracted with diethyl ether (2×100 ml) to remove minor amounts of yellow water-insoluble substances. The aqueous layer was rinsed with nitrogen to remove residual diethyl ether. Pure colorless alkaline solution is acidified by adding dropwise conc is trated chloride-hydrogen acid until until the pH reaches ˜1,3 (28 g, 0.28 mmol). During the first two thirds of add is an active gas. The product is filtered, washed with water (3×40 ml), then dried overnight at 55°With vacuum. The product consists of 11.7 g of white crystalline powder, which is practical net according to the1H NMR.

1H NMR (CDCl3) δ 7,33 (s, 1H), and 7.4-7.5 (m, 5H).

Stage C: Obtain 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonylchloride

A sample of crude 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (4,13 g, 16,1 mmol) dissolved in methylene chloride (45 ml). The solution is treated with oxalylamino (1.80 ml of 20.6 mmol) followed by addition of N,N-dimethylformamide (0,010 ml, 0.13 mmol). The evolution of gas begins immediately after adding N,N-dimethylformamide catalyst. The reaction mixture is stirred for ˜20 minutes at ambient conditions, and then heated to the boiling temperature under reflux for 35 minutes. Volatile compounds are removed by evaporation of the reaction mixture on a rotary evaporator with a bath temperature of 55°C. the Product is a 4,43 g light yellow oil. The only admixture according to the1H NMR is N,N-dimethylformamide.

1H NMR (CDCl3) δ 7,40 (m, 1H), 7,42 (s, 1H), 7,50-7,53 (m, 4H).

Stage D: Obtaining N-[2-methyl-6-[[(1-methylethyl)and the Ino]carbonyl]phenyl]-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Sample 3-methylisatoic anhydride (0,30 g, 1.7 mmol)partially dissolved in pyridine (4.0 ml) is treated with 1-phenyl-3-(cryptomaterial)-5-carboxylicacid (0.55 g, 1.9 mmol). The mixture is heated to ˜95°C for 2 hours. Received the orange solution is cooled to 29°C, then treated with Isopropylamine (1,00 g of 16.9 mmol). The reaction mass is heated to 39°C. Next, it is heated to 55°C for 30 minutes, during which a precipitate. The reaction mass is dissolved in methylene chloride (150 ml). The solution is washed with aqueous acid (5 ml conc. HCl in 45 ml of water), then water (2 g of sodium carbonate in 50 ml of water). The organic layer is dried over MgSO4, filtered, then concentrated on a rotary evaporator. If the volume decreases to ˜4 ml crystals are formed product. The suspension is diluted with ˜10 ml of diethyl ether, after which precipitates more product. The product is filtered, washed with diethyl ether (2×10 ml), then washed with water (2×50 ml). The wet cake is dried for 30 minutes at 70°With vacuum. The product is a 0.52 g of whitish powder, melting at 260-262°C.

1H NMR (DMSO-D6) δ 1,07 (1, 6N), of 2.21 (s, 3H), was 4.02 (octet, 1H), 7,2-7,4 (m, 3H), 7,45-7,6 (m, 6N), 8,10 (d, 1H), 10,31 (s, 1H).

Example 7

Stage a: 3-trifluoromethyl-2-[3-(trifluoromethyl)-1H-pyrazole-1-yl]pyridine/p>

A mixture of 2-chloro-3-triptoreline (3,62 g, 21 mmol), 3-cryptomaterial (2.7 g, 20 mmol) and potassium carbonate (6.0 g, 43 mmol) is heated at 100°C for 18 hours. The cooled reaction mixture is poured into a mixture of ice/water (100 ml). The mixture is twice extracted with diethyl ether (100 ml)and the combined ether extracts washed twice with water (100 ml). The organic layer is dried over magnesium sulfate and concentrated to obtain oil. Chromatography on a column of silica gel with hexane:ethyl acetate 8:1 to 4:1 as eluent gives specified in the title compound (3.5 g) as oil.

1H NMR (CDCl3) δ to 6.75 (m, 1H), 7.5 (m, 1H), and 8.2 (m, 2H), and 8.7 (m, 1H).

Stage b: 3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxylic acid

A mixture of compound indicated in the heading of example 5, step A (3.4 g, 13 mmol) dissolved in tetrahydrofuran (30 ml) and cooled to -70°C. Add diisopropylamide lithium (2 N. in heptane/tetrahydrofuran (THF) (Aldrich), and 9.5 ml, 19 mmol) and the resulting dark mixture is stirred for 10 minutes. The dried carbon dioxide bubbled through the mixture for 15 minutes. The mixture is heated to 23°and treated With water (50 ml) and 1 N. a solution of sodium hydroxide (10 ml). The aqueous mixture is extracted with diethyl ether (100 ml) and then ethyl acetate (100 ml). The aqueous layer was acidified with 6 N. chloride-hydrogen is islote to pH 1-2, and twice extracted with dichloromethane. The organic layer is dried over magnesium sulfate and concentrated to obtain specified in the title compound (1.5 g).

1H NMR (CDCl3) δ to 7.6 (m, 1H), 7,95 (m, 1H), 8,56 (m, 1H), 8, 9 (m, 1H), 14,2 (W, 1H).

Stage With: Obtaining N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxamide

A mixture of compound indicated in the heading of example 5, stage b (0.54 g, 1.1 mmol), the compound indicated in the heading of example 1, stage (of 0.44 g, 2.4 mmol) and BOP chloride (bis(2-oxo-oxazolidinyl)hasfinished, 0.54 g, 2.1 mmol) in acetonitrile (13 ml) is treated with triethylamine (0.9 ml). The mixture is shaken in a sealed scintillation vial for 18 hours. The reaction mixture is distributed between ethyl acetate (100 ml) and 1 N. chloride-hydrogen acid. The layer of ethyl acetate, sequentially washed with 1 N. chloride-hydrogen acid (50 ml), 1 N. sodium hydroxide (50 ml) and saturated sodium chloride solution (50 ml). The organic layer is dried over magnesium sulfate and concentrated. The residue is subjected to chromatography on a column of silica gel with hexane/ethyl acetate (from 5:1 to 3:1) as eluent. Specified in the header connection (0,43 g) was isolated as a white solid. TPL 227-230°C.

1H NMR (CDCl3) δ 1,2 (m, 6N), to 4.15 (m, 1H), 5,9 (sm, 1H), and 7.1 (m, 1H), ,2 (m, 2H), and 7.4 (s, 1H), 7,6 (m, 1H), 8,15 (m, 1H), total of 8.74 (m, 1H), 10,4 (W, 1H),

According to the methods described above, in combination with methods known in the art, can be obtained the following compounds of tables 1-17. In the tables the following abbreviations are used: t is tertiary, s - secondary, n is normal, i is ISO, with the cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert-butyl, Ph is phenyl, OMe is methoxy, OEt-ethoxy, SMe - methylthio, SEt - ethylthio, CN is cyano, NO2- nitro, TMS is trimethylsilyl, S(O) Me - methylsulfinyl and S(O)2Me - methylsulphonyl.

Preparative form/use

Compounds in accordance with this invention is usually used in the form of a formulation or composition with acceptable in agriculture carrier comprising at least one liquid diluent, a solid diluent or a surfactant. The ingredients of the formulation or composition is chosen so that they match the physical properties of the active ingredient, the method of application and environmental factors such as soil type, moisture and temperature. Used preparative forms include liquids, such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions and the like, which may not necessarily be thickened to a gel. Used preparative forms include solids, such as dusty, powders, granules, beads, tablets, films and the like, which may be dispersible in water ("wet") or soluble in water. The active ingredient may be (micro)encapsulated and then converted into a suspension or solid preparative form; alternatively, all preparative form of the active ingredient can be encapsulated (or "coated"). Encapsulation allows you to control or delay the release of active ingredient. Sprayable formulation can be placed in a suitable environment and be used when the volume of spray from about one to several hundred liters per hectare. Highly concentrated compositions are primarily used as an intermediate for other preparative forms.

Preparative forms typically contain an effective amount of the active ingredient, diluent and surfactant within the below approximate values, which together make up 100% of the mass.

Mass percentage
The active ingredient Surfactants
Dispersible in water and soluble granules, tablets and powders5-900-941-15
Suspensions, emulsions, solutions (including emulsifiable concentrates)5-5040-950-15
Dusty1-2570-990-5
Pellets and balls0,01-995-99,990-15
Highly concentrated compositions90-990-100-2

Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2ndEd., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2ndEd., Interscience, New York, 1950. In MaCutcheon''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 presents a list of surface-active substances and recommendations for their use. All preparative forms may contain minor amounts of additives to reduce foam, caking agents, corrosion, microbial growth, and similar events or thickeners to increase the viscosity.

Surfactants include, for example, polyethoxysiloxane alcohols, polyethoxysiloxane alkyltin the crystals, polyethoxysiloxane esters sorbitan and fatty acids, diallylmalonate, alkyl sulphates, alkylbenzenesulfonate, organosilicon compounds, N,N-dialkylamide, ligninsulfonate, condensates of naphthaleneformaldehyde, polycarboxylate and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, 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, paraffins, alkyl benzenes, alkylnaphthalene, oils: olive, castor, linseed, Tung, hemp, corn, peanut, cottonseed, soybean, rapeseed, coconut, esters of fatty acids, ketones, such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols, such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

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 grinder, working in the mode of fluidization. Su is pensii usually get wet grinding; see, for example, US 3060084. Granules and beads can be obtained by spraying the active material on pre-obtained granular carriers or by agglomeration. Cm. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, str-48, Perry's Chemical Engineer''s Handbook, 4thEd., McGraw-Hill, New York, 1963, p.8-57, and WO 91/13546. Beads can be obtained by the method described in US 4172714. Dispersible in water and soluble granules can be obtained as described in US 4144050, US 3920442 and DE 3246493. Tablets can be obtained, as described in US 5180587, US 5232701 and US 5208030. Film can be obtained, as described in GB 2095558 and US 3299566.

Additional information related to the field of preparative forms contained in US 3235361, column 6, line 16 to column 7, line 19 and examples 10-41; US 3309192, column 5, line 43 to column 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US 2891855, column 3, line 66 to column 5, line 17 and examples 1-4; Klingman, Need Control as a Science, John Wiley and Sons, Inc., New York, 1961, p.81-96; and Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989.

The following examples all percentages are mass and all the preparative form get the usual ways. Rooms compounds mean compounds in tables-pointers A.

Example

Wettable powder

Connection 165,0%
dodecyltrichlorosilane ether2,0%
ligninsulfonate sodium4,0%
the sodium aluminosilicate6,0%
montmorillonite (calcinated)23,0%

The example In

Granules

Connection 110,0%
Granules attapulgite (a substance with a low
volatility, of 0.71/0.30 mm; U.S.S. sieve No. 25-50)90,0%

The example

Extruded granules

Connection 125,0%
anhydrous sodium sulfate10,0%
untreated ligninsulfonate calcium5,0%
alkylnaphthalene sodium1,0%
calcium/magnesium bentonite59,0%

Example D

Emulsifiable concentrate

Connection 120,0%
the mixture is soluble in the oil sulfonates
and complex polyoxyethylenated esters10,0%
isophorone70,0%

Compounds in accordance with this image is emeniem have activity against a broad spectrum of eating the leaves, eating fruit, eating the trunk or roots, eating seeds, aquatic or soil arthropods (the term "arthropods" includes insects, mites and nematodes, which are pests of cultivated and stored crops, forests, greenhouse crops, ornamentals, seedlings, stored food and fiber products, livestock, Pets and animals kept in zoos. Specialist in the art will understand that not all compounds are equally effective against all pests at all stages of growth. However, all connections in accordance with this invention possess activity against pests, which include: eggs, larvae and adults of Lepidoptera; eggs, larvae, feeding on leaves, fruits, roots, seeds, and adults of the order of Coleoptera; eggs, immature individuals and adult groups Hemiptera and Homoptera; eggs, larvae, nymphs and adults of troop Acari; eggs, immature individuals and adult groups Thysanoptera, Orthoptera and Dermaptera; eggs, immature individuals and the adult squad Diptera; and eggs, young birds and adult individuals of the Phylum Nematoda. Compounds in accordance with this invention are also effective against pests units Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocotera; pests belonging to the class Arachnida and the Phylum Platyhelminthes. Particularly, the compounds of astout against South flea dinosau (Diabrotica undecimpunctata howardi), cycatki (Mascrosteles fascifrons), weevil cotton (Ankhonomus grandis), Clasica spider bimaculated (Tetranychus urticae), "the marching worm (Spodoptera frugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), cereal aphid (Sitobion avenae), whitefly (Bemisia tabacii), worms (Heliothis virescens), rice weevil water (Lissorhoptrus ocyzophilus), of rice leaf (Oulema oryzae), the short-tailed kobylecki (Sogatella furcifera), the green cycatki (Nephotettix cincticeps), brown kobylecki (Nilaparvata lugens), little brown kobylecki (Laodelphax striatellus), the liquidation (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), black rice bug-defender of rights (Scotinophara lurida), rice bug-aristida (Oebalus pugnax), rice bug (Leptocorisa chinensis), small rice bug (Cletus puntiger), southern green bug-Corsica (Nezara viridula) and German cockroach (Blatella germanica). Compounds acting on ticks, demonstrating the effect on the eggs, larvae and chemosterilants action against such families, as Tetranycidae, including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banks and Oligonychus pratensis; Tenuipalpidae, including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophydae, including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 to obtain more than the detailed descriptions of the pests.

Compounds in accordance with this invention can also be mixed with one or more other insecticides, fungicides, nematicides, bactericides, acaricides, plant growth regulators, hamsterisation, semiochemical compounds, repellents, attractants, pheromones, stimulants food or other biologically active compounds with obtaining multicomponent pesticide, providing a broader spectrum of agricultural protection. Examples of such agricultural protective compositions which can be mixed compounds in accordance with this invention are: insecticides such as abamectin, Arafat, avermectin, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, clothianidin, cyfluthrin, beta-cyfluthrin, cigalotrin, lambda cigalotrin, cypermethrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, giovanola, emamectin, endosulfan, esfenvalerate, fanatical, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, Tau-fluvalinate, flufenoxuron, fonofos, Imidacloprid, isofenphos, Malathion, metaldehyde, metamidophos, methidathion, methomyl, methoprene, Methoxychlor, methyl 7-chloro-2,5-dihydro-2[[N-(methoxycarbonyl)-N-[4-(triptoreline)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4A(3H)carboxylate (indoxacarb), monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, Fort, fozalon, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyriproxifen, rotenon, spinosad, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides, such as acibenzolar, AZOXYSTROBIN, benomyl, blasticidin-S, Bordeaux mixture, bromuconazole, cropropamide (KTU 3616), captafol, Captan, carbendazim, chloroneb, CHLOROTHALONIL, oxychloride copper salts of copper, having cymoxanil, tsyprokonazolu, cyprodinil (CGA 219417), (S) - for 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281), diclocil (S-2900), declomycin, dicloran, difenoconazol, (S) - for 3,5-dihydro-5-methyl-2(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one (RP 407213), dimethomorph, diniconazole, diniconazole-M, Dodin, edifenphos, epoxiconazol (WHA 480F), famoxadone, fenamidone, fenarimol, fenbuconazole, paneramic (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludyoksonil flamethower (RPA 403397), Fluconazol, flusilazol, flutolanil, flutriafol, folpet, fosetyl-aluminum, parallaxis, parameter (S-82658), hexaconazole, ipconazole, iprobenfos, iprodion, isoprothiolane, kasugamycin, kresoxim-methyl, MANCOZEB, MANEB, mefenoxam, mepronil, metalaxyl, metconazole, metamyosyn/phenominalrose (SSF-126), myclobutanil is, neo-IsoIn (iron metanational), oxadixyl, penconazole, pencycuron, provenzal, prochloraz, propamocarb, propiconazol, pirivenas, pyraclostrobin, Pyrimethanil, pyroxylin, jenoxifen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazol, leflunomid, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyclazole, Trifloxystrobin, triticonazole, validamycin and vinclozolin; nematicides, such as aldicarb, oxamyl and fenamiphos; antibacterial agents 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 such as Bacillus thuringiensis, Bacillus thuringiensis Delta endotoxin, baculovirus, and entomopathogenic bacteria, viruses and fungi.

Preferred insecticides and acaricides for mixing with compounds in accordance with this invention include pyrethroids such as cypermethrin, cigalotrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates, such as fanatical, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, Imidacloprid and thiacloprid, blockers of neuronal sodium channels, such as indoxacarb, insecticidal macrocyclic lactones, such as with inesad, the abamectin, avermectin and emamectin; GABA agonists, such as endosulfan and fipronil; urea insecticide, such as flufenoxuron and triflumuron, replicas of the hormones of young individuals, such as giovanola and pyriproxyfen; pymetrozine; and amitraz. Preferred biological agents for mixing with compounds in accordance with this invention include Bacillus thuringiensis and Bacillus thuringiensis Delta endotoxin.

The most preferred mixtures include a mixture of compounds in accordance with this invention with cyhalothrin; a mixture of compounds in accordance with this invention with beta-cyfluthrin; a mixture of compounds in accordance with this invention with esfenvalerate; a mixture of compounds in accordance with this invention with matomela; a mixture of compounds in accordance with this invention with Imidacloprid; a mixture of compounds in accordance with this invention with thiacloprid; a mixture of compounds in accordance with this invention with indoxacarb; a mixture of compounds in accordance with this invention with abamectin; a mixture of compounds in accordance with this invention with endosulfan; a mixture of compounds in accordance with this invention with fipronil; a mixture of compounds in accordance with this invention with flufenoxuron; a mixture of compounds in accordance with this invention with pyriproxyfen the nom; the mixture of compounds in accordance with this invention with pymetrozine; a mixture of compounds in accordance with this invention with nitraza; a mixture of compounds in accordance with this invention with Bacillus thuringiensis and a mixture of compounds in accordance with this invention with Bacillus thuringiensis Delta-endotoxin.

In certain instances, combinations with other arthropodicides having a similar spectrum of control but a different mode of action, are particularly preferred from the viewpoint of the stability control.

Arthropod pests control and protect agricultural, horticultural and specialty crops, animals and humans by applying one or more compounds in accordance with this invention, an effective amount, on the habitat of the pests, including agricultural and/or non-agricultural habitat of pests on the protected area or directly on the pests controlled. Thus, this invention also relates to a method of monitoring found on the foliage and in the soil arthropods and nematodes, and protection of agriculture and/or agricultural crops, comprising applying one or more compounds in accordance with this invention or compositions containing at least one such compound in ffective number, on the habitat of the pests, including agricultural and/or non-agricultural habitat of pests on the protected area or directly on the pests controlled. The preferred method of application is spraying. Alternatively, granular formulations of such compounds can be applied to the foliage of plants or to the soil. Other methods include direct and residual spraying, air spraying, shell, seed, microencapsulation, systemic absorption, bait, tags on the ears, boles, romanobritish, fumigants, aerosols, dusty and much more. Connections can be placed in bait that is absorbed arthropods, or in devices such as traps and such.

Compounds in accordance with this invention may be applied in pure form, but most often they are applied in the form of a formulation comprising one or more compounds with suitable carriers, diluents and surfactants, and possibly in combination with nutrients, depending on the intended end use. The preferred method of applying includes spraying water dispersion or refined oil solution of the compounds. Compositions with spray oils, concentration, spray oils, Faure, who as a spreader adjuvants, other solvents and synergists, such as piperonyl piperonyl often improve the normal efficiency of the connection.

The rate of application required for effective control depends on factors such as type of controlled arthropods life cycle of the pest, life stage, size, location, time of year, plant or animal host, feeding behavior, mating behavior, environment humidity, temperature and the like. Under normal conditions, the flow rate during application, comprising from about 0.01 to 2 kg of active ingredient per hectare, it is sufficient to control pests in agricultural ecosystems, but may be sufficient only 0.001 kg/hectare, or you may need not less than 8 kg/ha. For non-agricultural areas effective costs when applying the range from about 1.0 to 50 mg/square meter, but may be sufficient only 0.1 mg/square meter, or you may need not less than 150 mg/square meter.

The following test demonstrates the effectiveness of the control compounds in accordance with this invention certain types of pests. "Effectiveness monitoring", represents the inhibition of the development of arthropods (including death), which leads to a significant reduction of power. Pest control achieved by using a connection which changes in accordance with this invention, however, not limited to these types. See table pointers A-Q, with descriptions of compounds. In the tables the pointers used the following abbreviations: t is tertiary, n - normal, i - best, - cyclo, s - secondary, and Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, c-Pr cyclopropyl, Bu is butyl, s-Bu, - sec-butyl, Pent - pentyl, OMe is methoxy, OEt - ethoxy, SMe - methylthio, SEt - ethylthio, CN is cyano, NO2- nitro and Het is a heterocycle. The abbreviation "Etc." means "example" and comes with a number that indicates in which example get the connection.

Biological examples in accordance with this invention

Test

Application: Compounds dissolved in a mixture of 10% acetone, 90% water and 300 Tisch X-77 surfactant, unless otherwise noted. The composition of the compounds is applied using a spray gun with a nozzle SUJ2 with 1/8 JJ cylinder (Spraying Systems), located on the1/2" (1.2 cm) above the top of each test unit. These nozzles, whose total number is 6, form a rod with spray nozzles, which is recorded on a tape dispenser. Rack (or media) with 6 different sections of the test insects is placed on the conveyor belt and stop so that each section was centered under the nozzle. After alignment rack 1 ml of liquid is sprayed on each test section; then the rack move towards the end of the nozzle for discharge. All experimental compounds in this study is sprayed at 250 Tisch and repeat three times.

The cabbage moth (MK) - Plutella Xylostella: Test section consists of a small filled-in sections, which is located inside 12-14-day seedlings of redick is. She previously infected (using dirt tube) 10-15 newborn larvae in the feeding site of the insect. After spraying 1 ml of the composition of compounds at each test section, the test section is dried for 1 hour, then a black, screened cap was placed on top of the cylinder. They are stored for 6 days in an incubator at a temperature of 25°C and relative humidity of 70%.

Damage to plants is assessed visually on a scale from 0 to 10, where 0 means no damage, 1 damage 10% or less, 2 - damage 20% or less, 3 - damage 30% or less, up to a maximum assessment of 10, with 10 being 100% damage leaves. Among the tested compounds superior protection of plants was demonstrated by the following compounds (0-1, damage 10% or less): 1, 2, 3, 4, 6, 7, 9, 10, 13, 14, 15, 19, 20, 24, 27, 28, 29, 30, 31, 32, 33, 35, 37, 38, 39, 51, 52, 53, 60, 61, 62, 63, 64, 65, 66, 68, 69, 72, 73, 74, 75, 76, 79, 80, 84, 86, 88, 89, 90, 92, 96, 97, 98, 99, 100, 101, 102, 103, 107, 113, 124, 126, 127, 143, 144, 146, 147, 148, 150, 151, 152, 153, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 169, 170, 171, 174, 183, 184, 185, 186, 187, 188, 189, 190, 191, 193, 194, 195, 196, 198, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 222, 223, 225, 227, 228, 229, 230, 231, 232, 233, 235, 238, 239, 240, 244, 245, 246, 248, 249, 250, 251, 252, 253, 256, 257, 275, 276, 277, 278, B2, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, B15, B16, B17, B18, B19, B20, B21, V, In 24, B25, B28, V, B30, B, V32, U, V, W, V, W, In40, V, W, B44, V, B46, B47, V, W, 50, is 53, V, W, V, W, B60, V, W, V, W, V, W, V, W, 70, M, W, V, W, V, C1, C2, C3, C4, C5, C7, C8, C9, C10, C11, C12, C, D2, D3, D4, D5, D6, D7, D8, D11, D12, D13, D14, D15, D16, D18, D19, D20, D23, D24, D25, D26, D27, D28, D29, D30, D32, D33, D34, D37, D38, D39, D40, D41, D42, D45, D46, D47, D48, D50, D51, D52, D53, D54, D55, D56, D57, D58, D59, D60, D61, D62, D63, D64, D65, D66, D67, D68, D69, D70, D71, D72, D73, D74, D75, D76, D77, D78, D79, D81, D83, D84, D85, D86, D87, D88, D89, D91, D92, D93, D94, D95, D96, D97, D111, D113, D114, D115, D116, D117, D118, D119, D120, D121, D122, D123, D124, D125, D126, D162, D164, E4, F2, F5, F6, F7, F8, G2, G3, G5, H1, H2, H3, H4, J3, J4, J6, M1, N2 and P1.

Additionally, among the tested compounds superior protection of plants at a concentration of 50 thousand hours was demonstrated by the following compounds (0-1, damage 10% or less): 252, 254, D242-D245, D247, D248, D250 and D256-D259.

Additional data for compounds of the present invention are presented below in tables.

1. The compound of formula 1, its N-oxides and suitable for use in agriculture salt

where a is O;

In is O or S;

each J is independently phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6; or

each J is independently a 5 - or 6-membered heteroaromatic ring containing atoms of nitrogen, sulfur and/or oxygen, or an aromatic 8-membered of kondensierten the th heterobicyclic ring system, where each ring or ring system optionally substituted from 1 to 4 R7;

n is from 1 to 4;

R1is N or C1-C6the alkyl, which is optionally substituted by one or more2-C4alkoxycarbonyl;

R3is H, C1-C6the alkyl, C1-C4alkoxy or C1-C4alkyl amino;

R2is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, hydroxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl and C2-C6alkoxycarbonyl, or

R2and R3taken 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 of nitrogen or oxygen, where the aforementioned ring is optionally substituted 1-4 C1-C2alkyl groups;

each R4independently is H, C1-C6the alkyl, C2-C6the quinil, C1-C6halogenation, halogen, CN, NO2C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C 1-C4alkylsulfonyl, C1-C4alkylsulfonyl or3-C6trialkylsilyl; or

each R4independently is phenyl, which is optionally substituted C1-C4halogenation, halogen or CN;

each R5independently is C1-C6halogenation, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfonyl, C1-C4allogenicity, C1-C4halogenatedsolvents, C1-C4halogenated.sulphonated, CN, NO2With2-C4alkoxycarbonyl,2-C6alkylcarboxylic or3-C8dialkylaminoalkyl; or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-;

each R6independently is H, halogen, C1-C6the alkyl or C1-C4alkoxy or

each R6independently is phenyl, benzyl, 5 - or 6-membered heteroaromatic ring containing atoms of nitrogen, sulfur and/or oxygen, or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system containing nitrogen atoms, where each ring is optionally substituted on the him to three substituents, independently selected from the group comprising C1-C4alkyl, C3-C6cycloalkyl, C1-C4halogenated, halogen, CN, C1-C4alkoxy or2-C4alkylsulphonyl;

each R7independently is H, C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil,3-C6cycloalkyl, C1-C6halogenation,2-C6halogenation,2-C6halogenoalkanes, halogen, CN, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylamino or C2-C8dialkylamino or

each R7independently is phenyl, benzyl, benzoyl, phenoxy, or 5 - or 6-membered heteroaromatic ring containing atoms of nitrogen, sulfur and/or oxygen, or an aromatic 8-, 9 - or 10-membered condensed heterobicyclic ring system containing nitrogen atoms and/or sulfur, where each ring optionally substituted with one to three substituents, independently selected from the group comprising C1-C4alkyl, C2-C4alkenyl,2-C4quinil, C1-C4halogenated,2-C4halogenoalkanes, halogen, CN, C1-C4alkoxy or C1-C4halogenoalkane;

provided that

(i) at least one R4and at least one R7different from N;

(ii) J is different from optionally substituted 1,2,3-thiadiazole;

(iii) if J is an optionally substituted pyridine and R2is H, R3different from N or CH3;

(iv) if J is an optionally substituted pyrazole, tetrazole

or pyrimidine, R2and R3can't both be hydrogen.

2. The connection of claim 1, wherein J is a phenyl group substituted by from 1 to 2 R5and optionally substituted from 1 to 3 R6.

3. The compound according to claim 2, in which a and b both are About;

n is from 1 to 2;

R1is N or C1-C4by alkyl;

R3is N or C1-C4by alkyl;

R2is C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio and C1-C2alkylsulfonyl;

each R5independently is C1-C4halogenation, C1-C4halogenoalkane, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4what alkylsulfonyl, C1-C4allogenicity, C1-C4halogenated.sulphonated, CN, NO2or C1-C4alkoxycarbonyl or

(R5)2attached to adjacent carbon atoms may be taken together as-OCF2O-, -CF2CF2O - or-OCF2CF2O-; and

each R6independently is phenyl or 5 - or 6-membered heteroaromatic ring containing nitrogen atoms, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen, CN, C1-C4alkoxy or C2-C4alkylcarboxylic.

4. The compound according to claim 3 in which R1and R3both are N;

R2is C1-C4the alkyl, optionally substituted with halogen, CN, och3, SCH3or S(O)2CH3;

each R5independently is CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2The co2CF3, OCF2CHF2, S(O)pCH2CF3or S(O)pCF2CHF2;

each R6independently is phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN; and

p is 0, 1 or 2.

5. The compound according to claim 3 in which R 3is isopropyl or tert-bootrom.

6. The connection of claim 1, wherein J is a 5 - or 6-membered heteroaromatic ring, optionally substituted from 1 to 4 R7.

7. The connection according to claim 6, in which J is a 5 - or 6-membered heteroaromatic ring selected from the group including J-1, J-2, J-3, J-4 and J-5, where each J is optionally substituted from 1 to 3 R7,

Q is O, S or NR7and

W, X, Y and Z are independently N or CR7provided that in J-4 and J-5, at least one of W, X, Y or Z is N.

8. The connection according to claim 6 or 7, in which

A and b are About;

n is from 1 to 2;

R1is N or C1-C4by alkyl;

R3is N or C1-C4by alkyl;

R2is H, or C1-C6the alkyl, C2-C6alkenyl,2-C6the quinil or3-C6cycloalkyl, each of which is optionally substituted by one or more substituents selected from the group including halogen, CN, C1-C2alkoxy, C1-C2alkylthio and C1-C2alkylsulfonyl; each R7independently is H, C1 -C4the alkyl, C1-C4halogenation, halogen, CN, C1-C4halogenoalkane or C1-C4alkylthio, or a phenyl or 5 - or 6-membered heteroaromatic ring, where each ring optionally substituted C1-C4the alkyl, C2-C4alkenyl,2-C4the quinil, C1-C4halogenation,2-C4halogenation, halogen, CN, C1-C4alkoxy or C1-C4halogenoalkane.

9. The connection of claim 8, in which J is chosen from the group comprising pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazol and isoxazol, each of which is optionally substituted from 1 to 3 R7.

10. The connection according to claim 9, in which J is chosen from the group comprising pyridine, pyrimidine, pyrazole, thiophene and thiazole, each of which is optionally substituted from 1 to 3 R7;

R1and R3both are N;

R2is C1-C4the alkyl, optionally substituted with halogen, CN, och3, SCH3or S(O)2CH3;

each R7independently is phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, C1-C4alkoxy, C1-C4halogenic the XI, halogen or CN.

11. The connection of claim 10, in which J is pyridine, optionally substituted from 1 to 3 R7.

12. Connection by claim 11, in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

13. Connection by claim 11, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

14. The connection of claim 10, in which J is a pyrimidine, optionally substituted from 1 to 3 R7.

15. The connection 14, in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

16. The connection 14, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

17. The connection of claim 10, in which J is a pyrazole, optionally substituted from 1 to 3 R7.

18. The connection 17 in which one of R7is phenyl, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

19. Connect the s on 17, in which one of R7is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

20. The connection 17 in which R7is pyridine, optionally substituted C1-C4the alkyl, C1-C4halogenation, halogen or CN.

21. The compound according to claim 1, selected from the group including:

3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamid,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,

1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(2-forfinal)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and

3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-feast of the evil-5-carboxamide.

22. Arthropodicides composition comprising arthropodicides effective amount of the compounds of formula 1 according to claim 1 and at least one additional component selected from the group comprising surfactants, solid diluents and liquid diluents.

23. The method of control of arthropods, including the processing of arthropods or their environment arthropodicides effective amount of a compound according to claim 1 or the composition according to item 22.



 

Same patents:

FIELD: organic chemistry, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of amidines of the general formula (I):

wherein R1 means alkyl; R2 means alkyl, alkenyl, alkynyl or cyanoalkyl; R3 means hydrogen atom; n = 0 or 1; X means -(CH2)m- wherein m = 0 or 1; A means heterocyclic 5-membered aryl radical comprising sulfur atom (S), or to salts of these compounds, their preparing and using as medicinal agents. Also, invention relates to using abovementioned derivatives for preparing a medicinal agent designated for inhibition of activity of NO-synthases (NOS) and/or monoaminoxidases (MAO).

EFFECT: improved preparing method, valuable medicinal properties of compounds.

6 cl, 5 ex

The invention relates to 2,4,5-triple-substituted phenylethanol formula I, in which HET denotes one of the groups(1), (2), (3), (4), (5)

FIELD: organic chemistry, chemical technology, pesticides.

SUBSTANCE: invention describes a method for preparing a compound of the formula (I): in free form or as a salt wherein Q means -CH or nitrogen atom (N); Y means -NO2 or -CN; Z means -CHR3, oxygen atom (O), -NR3 or sulfur atom (S); R1 and R2 mean, for example, (C1-C8)-alkyl or form in common an alkylene bridge; R3 means hydrogen atom or free (C1-C12)-alkyl or substituted with radical R wherein R4 means unsubstituted or substituted aryl or heteroaryl group. In proposed method by variant a) compound of the formula (II): wherein X means the removing group is subjected for interaction with a chlorinating agent to form compound of the formula (III): in free form or as a salt, and by variant b) compound of the formula (III) prepared by such method is subjected for interaction with compound of the formula (IV): wherein R1, R2, Y, Z and Q have values given for the formula (I), and the chlorination process at the stage a) is carried out in the continuous regimen. Also, invention describes a method for preparing compound of the formula (III) in the correspondence of abovementioned stage a), and using compounds of formulae (II), (III) and (IV) in a method described above. Technical result of the invention involves improving method for preparing compound of the formula (I) used as pesticides.

EFFECT: improved preparing method.

5 cl, 5 ex

The invention relates to a method for obtaining compounds of formula I in each case in free form and in salt form, where Q denotes CH or N, Y represents the NO2or CN, Z means СНR3OH , NR3or S, R1and R2each independently of one another denotes hydrogen, unsubstituted or R4-substituted C1-C8alkyl or together form Allenby bridge of two or three carbon atoms, and Allenby bridge may optionally contain a heteroatom selected from the group comprising NR5, O or S, R3means H, unsubstituted or R4-substituted C1-C12lcil, R4means unsubstituted or substituted aryl or heteroaryl, R5means N or C1-C12alkyl, by transformation of compounds of formula II in which R is cyclohexyl, phenyl, benzyl or a group of formula (a)1means a leaving group, using a halogenation agent in the compound of formula IV, where X is halogen, the conversion of the compounds of formula IV by reacting with the compound of the formula V to the compound of formula VI, which is then transformed using glorieuses agent in the compound of formula I

The invention relates to new derivatives of cephalosporin of the General formula I and II where R1selected from the group consisting of-NНС(O)ZR3, -NR4R5; Z is selected from the group consisting of-CH2(X)m-, -C(NОR6)-; X is a sulfur atom; m = 0 - 1; R3- thiazolyl substituted by chlorine or amino group, and (CH2)T, where n = 1 to 6; T - guanidino; R4and R5each hydrogen; R6is hydrogen or may be a group which with the adjacent oxygen atom forms a protected hydroxyl group,2is hydrogen; each of G, H, L, and M - carbon; J is nitrogen; rings a, b, D and E are selected from the group consisting of thiazolyl and thiadiazolyl; R11is hydrogen; alk1- C1-6alkyl; alk2- C1-6alkyl, optionally substituted by a group selected from hydroxyl, amino, carboxamido; p is 0 to 1; R99selected from the group consisting of sulfur and SO2; q is 1; r = 1 - 3; R12- NR13R14group (a) or (b); R13-R17each is hydrogen, or its pharmaceutically acceptable salt

The invention relates to new substituted phenyl derivatives, which are strong blockers chlorine ion channels and as such are useful in the treatment of sickle cell anemia, cerebral edema that accompanies ischemia or tumor, diarrhea, hypertension (diuretic), osteoporosis and to reduce the intraocular pressure for the treatment of disorders such as glaucoma

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new derivatives of 5-phenylpyrimidine or their pharmaceutically acceptable acid-additive salts that elicit properties of antagonists of neuropeptide receptor neurokinin-1 (NK-1). This allows their applying for treatment of such diseases as Alzheimer's disease, cerebrospinal sclerosis, attenuating syndrome in morphine withdrawal, cardiovascular alterations and so on. Compounds of invention correspond to the general formula (I):

wherein R1 means hydrogen or halogen; R2 means hydrogen, halogen atom, (lower)-alkyl or (lower)-alkoxy-group; R3 means halogen atom, trifluoromethyl group, (lower)-alkoxy-group or (lower)-alkyl; R4/R4' mean independently hydrogen atom or (lower)-alkyl; R5 means (lower)-alkyl, (lower)-alkoxy-group, amino-group, hydroxyl group, hydroxy-(lower)-alkyl, -(CH2)n-piperazinyl substituted optionally with lower alkyl, -(CH)n-morpholinyl, -(CH2)n+1-imidazolyl, -O-(CH2)n+1-morpholinyl, -O-(CH2)n+1-piperidinyl, (lower)-alkylsulfanyl, (lower)-alkylsulfonyl, benzylamino-group, -NH-(CH2)n+1N(R4'')2, -(CH2)n-NH-(CH2)n+1N(R4'')2, -(CH2)n+1N(R4'')2 or -O-(CH2)n+1N(R4'')2 wherein R4'' means hydrogen atom or (lower)-alkyl; R6 means hydrogen atom; R2 and R6 or R1 and R6 in common with two ring carbon atoms can represent -CH=CH-CH=CH- under condition that n for R1 is 1; n means independently 0-2; X means -C(O)N(R4'')- or -N(R4'')C(O)-. Also, invention relates to a pharmaceutical composition.

EFFECT: valuable medicinal properties of compounds.

15 cl, 4 sch, 86 ex

The invention relates to new derivatives of 2-(O-[pyrimidine-4-yl]metalinox)phenylacetic acid, their salts and N-oxides of the General formula I, means for combating harmful fungi and pests, the method of production thereof and method of combating harmful fungi and pests with the use of compounds of General formula I

The invention relates to new derivatives of 5H-pyrano[2,3-d:6,5-d']dipyrimidine General formula I possess anti-microbial, antiviral and immunomodulatory effects

The invention relates to applicable in medicine new derived aminotriazole or its hydrate and its pharmaceutically acceptable salts

The invention relates to the derivatives of triazole, exhibiting antifungal activity

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

FIELD: organic chemistry, fungicides, agriculture.

SUBSTANCE: invention describes pyrazolcarboxamide of the formula (I) wherein if X means oxygen atom (O) then R1 represents (C1-C3)-alkoxy-(C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means fluorine (F), chlorine (Cl) or bromine atom (Br), and if X means sulfur atom (S) then R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means halogen atom. Also, invention describes a method for preparing compounds of the formula (I), a composition for control of microorganisms and prevention for their attack and damage of plants, and a method for control of phytopathogen organisms, and compound of the formula (V) wherein X means sulfur atom (S); R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means chlorine, bromide or iodine atom. Invention provides control and prevention in infection of plants with phytopathogenic microorganisms - fungi in agriculture and horticulture.

EFFECT: valuable agricultural properties of compounds.

9 cl, 4 tbl, 12 ex

The invention relates to N-piperidino-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-aripirazole-3-carboxamide, its pharmaceutically acceptable salt and solvate, which are strong antagonists of cannabinoid ST1receptors

The invention relates to substituted 1-phenylpyrazol-3-carboxamide formula (Ia) in which R1xis in position 4 or 5 and denotes the group-T-CONRaRbin which T represents a direct bond or (C1-C7-alkylen; NRaRbdenotes a group selected from (a), (b), (C); R5and R6denote, independently of one another, hydrogen, (C1-C6)-alkyl, (C3-C8)-alkenyl or R5and R6together with the nitrogen atom to which they are linked, represent a heterocycle selected from pyrrolidine, piperidine, research, piperazine, substituted in position 4 by Deputy R9; R7denotes hydrogen, (C1-C4)-alkyl or benzyl; R8denotes hydrogen, (C1-C4)-alkyl, or R7and R8together with the carbon atom to which they are attached, form a (C3-C5-cycloalkyl; R9denotes hydrogen, (C1-C4)-alkyl, benzyl or a group-X-NR'5R'6in which R'5and R'6represent, independently from each other, (C1-C6)-alkyl; R10denotes hydrogen, (C1-C4)-alkyl; s= 0-3; t=0-3, provided that (s+t) in the same group greater than or equal to 1; the divalent radicals a and E together with the atom is which in addition, may be substituted by one or more (C1-C4-alkilani; R2xand R3xdenote, independently of one another, hydrogen, (C1-C6)-alkyl, (C3-C8-cycloalkyl, (C3-C8-cyclooctylmethyl provided that R2xand R3xdo not simultaneously denote hydrogen or R2xand R3xtogether form tetramethylene group; and their pharmaceutically acceptable salts

The invention relates to new compounds for combating pests, in particular derivatives carbanilide and fungicide-insecticidal tool based on them

The invention relates to pyrazole derivative of the formula I, where1means the group - NRR1R2or group-OR2, g2- g6the same or different and independently of one another denote hydrogen, halogen, C1-4alkyl, C1-4alkoxyl, trifluoromethyl, or C1-4allylthiourea; w2-w6the same or different and independently of one another denote hydrogen, halogen, C1-4alkyl, C1-4alkoxy or trifluoromethyl, provided that at least one of the substituents g2-g6and one of the substituents w2-w6different from hydrogen; R1means hydrogen or C1-4alkyl; R2- nah3-15-carbocyclic radical, unsubstituted or mono - or multiply substituted WITH1-4by alkyl; R3is hydrogen or the group CH2-R6; R4and R5each independently of one another denote hydrogen or C1-4alkyl; or R4means hydrogen and R5and w6together form an ethylene radical; R6means hydrogen, or when the deputies of the g2g3, g4, g5and/or g6different from1-4of alkyl, R6means hydrogen, C1-4alkyl or C1-5alkoxyl, and their salts
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