Pyrazole derivative, agent for insect control comprising thereof as active component and methods for its preparing

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-pyridylalkylaminopyrazole represented by the following formula (1): wherein X represents C-halogen; R1 represents halogenalkyl group comprising from 1 to 4 carbon atoms with exception of perhalogenalkyl group; R2 represents hydrogen atom; R3 represents hydrogen atom; R4 represents hydrogen atom. Also, invention describes an agent used for control of insects comprising this derivative as an active component. Invention describes two methods for preparing compound of the formula 91). Compounds of the formula (1) are useful for control of insects in agriculture and for domestic animals.

EFFECT: improved preparing methods, valuable properties of compound and agent.

7 cl, 7 tbl, 7 ex

 

The scope of the invention

The present invention relates to new derivatives of 1-aryl-3-cyano-5-pyridylacetonitrile and to an agent for combating pests, in particular to the insecticide containing as the active ingredient.

Background of the invention

In the field of agriculture and horticulture developed and brought into practical use for the purposes of control of various insect pests a large number of insecticides as agents for pest control.

For example, pyrazole compounds having insecticidal activity, derivatives of Z-cyano-1-phenylpyrazole having an amino group as a substituent in the 5-position described in the Japan patent JP-A-62-228065, JP-A-63-316771 and JP-A-3-118369, substituted derivatives of 1-aryl-3-cyano-5-(het)arylmethylidene described in Japan patent JP-A-5-148240, and substituted derivatives of 1-aryl-5-(het)arylmethylidene described in Japan patent JP-A-64-47768.

However, the compounds described in the above literature, are not necessarily satisfactory in respect of all insecticidal action, spectrum of insecticidal impact, safety and the like, and for this reason it is desirable to develop new compounds to overcome these problems. As a consequence, new derivatives of 1-aryl-3-cyano-5-heterooligomerization who have been described as compounds, demonstrating high security in the Japan patent JP-A-10-338676.

However, the compounds described in Japan patent JP-A-10-338676 and the like are excellent in insecticidal activity and have lower toxicity than the known compounds, but find problems associated with the fact that the compounds have insufficient performance, from the point of view of their systemic activity, as compounds having high system activity, have a lack of security. From the viewpoint of effective use of the agent for pest control and application to soil, especially effective against organisms pests, such as sucking the liquid pests, system activity is an important factor. In addition, in recent years, increased security requirements in relation to organisms other than the target insect pests, and the environment, and then were taken strict measures to protect the environment. For this reason, in order of development of pesticides that meet more stringent limitations, an important problem of finding compounds with higher security.

Description of the invention

As a result of intensive studies to solve the above problems, the authors of the present invention have found that compounds the tion, with improved systemic activity and high safety is obtained by using peredelnoj group as a heteroaryl group attached to alkylamine in the 5-position of the pyrazol ring derivatives of 1-aryl-3-cyano-5-heterooligomerization, and additional use of partially halogenated specific ancilliary as a substituent in the 4-position of the pyrazol ring, and thus have accomplished the present invention.

Namely, the present invention relates to derivatives of 1-aryl-3-cyano-5-pyridylacetonitrile, represented by the following formula (1):

where X represents N or C-halogen (carbon atom substituted by a halogen atom); R1is halogenating group, except perhalogenated group; R2represents a hydrogen atom or alkyl group; R3represents a hydrogen atom, alkyl group or acyl group; and R4represents a hydrogen atom, hydroxyl group, alkyl group, halogenation group, alkoxygroup, halogenlampe, allylthiourea, alkylsulfonyl group, alkylsulfonyl group, a halogen atom, a nitro-group, or cyano, and agent for pest control containing the derivative as active Ingram the rate, and the way to get the connection.

The best way of carrying out the invention

Further, the present invention is explained in detail. In the present invention, the substituent R1in the compounds represented by the above formula (1)is a partially halogenated alkyl group with straight or branched chain, such as permetrina group, deformational group, 2-florachilena group, 2-chloraniline group, 2,2,2-triptorelin group, 2,2,2-trichlorethylene group, 3-chloropropylene group, 3-bromopropyne group, 3,3,3-cryptosporella group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2-dichloro-3,3,3-cryptosporella group, 2,2-dichloro-3,3,3-cryptosporella group, 3,3,3-trichloropropane group 4-garbatella group, 4,4,4-triptorelin group, or 3,3,4,4,4-pentafluorobutane group. Among them, halogenation group having 1-4 carbon atoms is preferred, and halogenation group having 1-2 carbon atoms, such as permetrina group, and deformational group, are particularly preferred.

R2represents a hydrogen atom; alkyl group with straight or branched chain, such as methyl group, ethyl group, n-sawn group, isopropyl group, n-bucilina group, isobutylene group, W is p-bucilina group or tert-bucilina group. Among them, a hydrogen atom and an alkyl group having 1-4 carbon atoms, are preferred, and hydrogen atom is particularly preferred.

R3represents a hydrogen atom; alkyl group with straight or branched chain, such as methyl group, ethyl group, n-sawn group, isopropyl group, n-bucilina group, isobutylene group, sec-bucilina group, or tert-bucilina group; or an acyl group, straight or branched chain, such as methylcarbamyl group, acylcarnitine group, n-propellerblade group, isopropylcarbodiimide group, n-butylcellosolve group, isobutylamine group, sec-butylcellosolve group or tert-butylcellosolve group. As the above alkyl groups and acyl groups, groups having 1-4 carbon atoms, are preferred. As R3the hydrogen atom is particularly preferred.

R4represents a hydrogen atom; hydroxyl group; alkyl group with straight or branched chain, such as methyl group, ethyl group, n-sawn group, isopropyl group, n-bucilina group, isobutylene group, sec-bucilina group, or tert-bucilina group; halogenation group with a straight or branched chain, such as deformational group, t is ivermectina group, 2-florachilena group, 2-chloraniline group, 2,2,2-triptorelin group, 2,2,2-trichlorethylene group, 3-chloropropylene group, 3-bromopropyne group, 3,3,3-cryptosporella group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2-dichloro-3,3,3-cryptosporella group, 2,2-dichloro-3,3,3-cryptosporella group, 1,3-debtor-2-through the group, 1,1,1,3,3,3-hexamer-2-through the group, 3,3,3-trichloropropane group, 4-garbatella group, 4,4,4-triptorelin group or 3,3,4,4,4-pentafluorobutane group; alkoxygroup straight or branched chain, such as methoxy group, ethoxypropan, n-propoxy group, isopropoxy, n-butoxypropyl, isobutoxy, second-butoxypropan or tert-butoxypropan; halogenlampe straight or branched chain, such as dipterocarp, tripterocarpa, 2-floratone group, 2-chlorethoxyfos, 2,2,2-triftoratsetata, 2,2,2-trilobitomorpha, 3-chloroptera, 3-brontophobia, 3,3,3-cryptocracy, 2,2,3,3-tetrafluoropropoxy, 2,2,3,3,3-pentafluoropropyl, 2,2-dichloro-3,3,3-cryptocracy, 2,2-dichloro-3,3,3-cryptocracy 1,3-debtor-2-propoxylate, 1,1,1,3,3,3-hexamer-2-propoxylate, 3,3,3-trichloropropane, 4-chlorotoxin, 4,4,4-tripcomputer or 3,3,4,4,4-pentafluorobutane; alkylthiols with p the pit or branched chain, such as methylthiourea, ethylthiourea, n-PropertyGroup, isopropylthio, n-butylthiourea, isobutylthiazole, second-butylthiourea or tert-butylthiourea; alkylsulfonyl group with a straight or branched chain, such as methylsulfinyl group, ethylsulfinyl group, n-propylsulfonyl group, isopropylaniline group, n-butylsulfonyl group, isobutylphenyl group, sec-butylsulfonyl group or tert-butylsulfonyl group; alkylsulfonyl group with a straight or branched chain, such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylaniline group, n-butylsulfonyl group, isobutylphenyl group, second-butylsulfonyl group or tert-butylsulfonyl group; halogen atom such as chlorine atom, fluorine atom or bromine atom; a nitro-group; or cyano. Among them, as the above alkyl group, halogenoalkanes group, alkoxygroup, halogenlampe, allylthiourea, alkylsulfonyl group and alkylsulfonyl groups, groups having 1-4 carbon atoms, are preferred. In particular, as R4the atom of hydrogen and an alkyl group are preferred, and a hydrogen atom is most preferable.

Among connection the settings of the above formula (1) compounds, derived from the combination of the preferred substituents on each of R1-R4are more preferable.

Examples of preferred combinations of the above substituents include compounds where R1is partially halogenated alkyl group having 1-2 carbon atoms, and R2, R3and R4represent hydrogen atoms. Among them, groups, where R1is pharmacylow group or deformational group, are preferred, since they exhibit a high insecticidal activity (i.e. sufficient insecticidal effect is obtained even at low concentrations of the compounds when they are used as active ingredients, agents for combating pests, in particular insecticides. The most preferred compound, as shown below, is a 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile.

As a method of obtaining compounds of the present invention represented by the above formula (1)may be used a method of obtaining described in Japan patent JP-A-10-338676. In addition, the methods depicted in the following schemes of reactions 1-4, may be considered as preferable compared the structure with other methods.

(Where R1, R2, R3, R4and X have the same meanings as described above.)

The reaction scheme 1 depicts a method of obtaining a pyrazole derivative of the formula (1), which includes the processing of the pyrazole derivative of the formula (2) with R1SX1where R1has the same meaning as in the formula (1), and X1represents a chlorine atom, a bromine atom, alkylsulfonyl group or arylsulfonyl group. X1represents preferably a chlorine atom. Specific examples of R1SX1include differetialoperatoren (CHF2SCl), and the connection can be obtained using the method described in J. Org. Chem., Vol.44, №10, 1708 (1979).

In this reaction, R1SX1used in quantities of from 0.5 to 10.0 molar equivalents, preferably from 0.8 to 5 molar equivalents relative to the compound represented by formula (2), and the interaction is carried out at 0°C-150°C, preferably 0°S-100°usually within 1-24 hours, preferably 1-4 hours, which may vary, depending on the scale of the response.

The solvent for use in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; a ketone, such as acetone and methyl ethyl ketone; halogenated hydrocarbons, such as chlorof the RM and methylene chloride; ethereal solvent, such as ether, diisopropyl ether and tetrahydrofuran; an aprotic polar solvent such as N,N-dimethylformamide (DMF) and dimethylsulfoxide; and the like. Among them, toluene and dichloromethane are preferred.

The reaction is preferably carried out in the presence of a base, and an amine, such as pyridine or triethylamine, is used as the base.

The reaction scheme 2 illustrates a method of obtaining a pyrazole derivative of the formula (1), which includes the processing of the pyrazole derivative of the formula (3) using halogenosilanes agent.

Examples halogenosilanes agent for use in the reaction include formatlibrary, deformational, trimethylsilyldiazomethane and the like.

The solvent for use in the reaction include ether solvents such as tetrahydrofuran, diethyl ether and dimethoxyethane; a hydrocarbon solvent such as toluene and hexane; halogenated hydrocarbon solvent, such as dichloromethane and chloroform; and the like. Among them, tetrahydrofuran is preferred.

In response, halogenaryloxy agent is used in amounts of from 0.5 to 10.0 molar equivalents, preferably from 0.8 to 5 molar equivalents relative to the compound represented by formula (3), and interaction of the journey is carried out at -20° S-120°C, preferably from 0°C to room temperature, usually within 1-24 hours, preferably 1-4 hours, which may vary, depending on the scale of the response.

The reaction scheme 3 depicts a method of obtaining a pyrazole derivative of the formula (1), which includes the processing of the pyrazole derivative of the formula (4) using halogenosilanes agent.

Examples halogenosilanes agent include halogenaryloxy agent having halogenmethyl group. Halogenaryloxy agent having halogenmethyl group represents, preferably, a compound that deformational group, and more preferably a compound known as deformability predecessor. Examples diftorkarbenovogo predecessor include compounds described in Organofluorine Compounds, p.107-111, Hiyama, Springer, and specific examples include deformational, Hortiflorexpo acid, salt Hortiflorexpo acid with metals, esters Hortiflorexpo acid and the like.

The solvent for use in the reaction include aprotic polar solvent such as N,N-dimethylformamide (DMF) and dimethylsulfoxide (DMSO); alcohol solvent such as methanol, ethanol, and isopropanol; a hydrocarbon solvent such as toluene and hexane; halogenated hydrocarbon solution of the tel, such as dichloromethane and chloroform; alkaline solvent, such as triethylamine and liquid ammonia; and the like. Among them, a polar solvent, such as DMF or alcoholic solvent, such as ethanol and isopropanol, are preferred.

The interaction is carried out at -20°s-200°C, preferably at 0°C-150°C for 1-24 hours, preferably 1-4 hours.

Furthermore, the reaction can be carried out also in the form of a two-phase system. In this case, the solvent includes a two-layer system of a polar solvent, such as dioxane, or a hydrocarbon solvent such as toluene or xylene, and the concentrated aqueous solution of sodium hydroxide. The interaction is carried out in the presence of a catalyst phase transfer, such as tetrabutylammonium bromide, at the reaction temperature -20°to 120°C, preferably from 0°C to room temperature, usually within 1-24 hours, preferably 1-4 hours, which may vary, depending on the scale of the response.

The reaction scheme 4 depicts a method of obtaining a pyrazole derivative of the formula (1), which includes the processing of the pyrazole derivative of the formula (5) using halogenosilanes agent.

In response, the interaction is carried out in the presence of a reducing agent, if the mu is Dimo.

Examples of the reducing agent include hydrides, such as borohydride sodium, borohydride zinc and lithium aluminum hydride; metal zinc; hydrazine; and the like. The number that should be used is in the range of 1 to 20-fold molar excess, preferably 1-5-fold molar excess, relative to the substrate.

Other reagents and conditions that should be used are the same as in the explanation concerning the above formula (3).

In this respect, the compound of the above formula (3), (4) or (5) can be obtained using known methods using the compounds of formula (2) as the starting material.

In the case of 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile, which is the most preferred of the compounds of the present invention, the methods shown in reaction scheme 1 and scheme of reaction 4', are considered as examples of particularly preferred ways of receiving.

Next is described a method of obtaining a pyrazole derivative represented by the formula (2). Two methods are given as examples of ways to obtain a pyrazole derivative represented by the formula (2).

1) the Method for converting the side chain PR is izvorovo of pyrazole.

2) Method to obtain the target compounds by synthesis of pyrazole skeleton.

In the method of conversion of the side chain derivative of pyrazole 1) can be applied a method of obtaining an amine, which is well-known (for example, the method described in Organic Functional Group Preparations I, p.377, chapter 13 (Amines), Academic Press, 1983). Specifically, a pyrazole derivative represented by the formula (2)can be obtained by using compounds represented by formula (6), (7) or (8)as raw material, using the methods depicted in schemes reactions 5-8.

(Where X, R2, R3and R4have the same meanings as in the formula (1); X5represents a removable group such as a halogen atom or a hydroxyl group; X6represents a halogen atom, a hydroxyl group, or alkoxygroup; X7represents a halogen atom and a is an R4- pyridyloxy group.)

In the reactions of condensation, in the above reaction schemes, each of them can be carried out in accordance with the known method.

Moreover, as a reducing agent can be used reagent for the recovery of the imine, amide or halogenide, and use the hydrogen or substance-donor hydrogen. When using hydrogen, usually used in isoamsa catalyst, such as palladium or platinum. Examples of substances donor hydrogen include organic chemicals, hydrogen donors, such as formic acid and isopropanol; inorganic chemicals, hydrogen donors, such as hydrazine; metal hydrides; and the like. Metal hydrides include a complex of borane-THF, borohydride sodium, cyanoborohydride sodium, borohydride lithium, lithium aluminum hydride and the like. In the case of reaction scheme 8 is also effective so-called reductive amination, where exercise and education iminovogo connection (10) and (b) the formation of a derivative of pyrazole (2) by restoring on the same stage.

The solvent for use in the reaction include polar solvent, e.g. an ether, such as diethyl ether, dioxane, and tetrahydrofuran; alcohol, such as methanol, ethanol and propanol; and the like.

The interaction is carried out at a temperature from -20°to 120°C, preferably from 0°C to room temperature for 1-24 hours, preferably 1-4 hours.

Gloriouse agent for use in galogenirovannyie includes pentachloride phosphorus, phosphorus oxychloride, thionyl chloride and the like.

The solvent for use in the reaction includes a non-polar solvent, such as benzene, toluene, and xylene; g is agenerally solvent, such as carbon tetrachloride, chloroform, and dichloromethane; an ethereal solvent, such as dimethoxyethane and tetrahydrofuran; and the like.

The interaction is carried out at a temperature from 0°to 200°C, preferably from room temperature to 150°within 1-24 hours, preferably 1-4 hours.

As a way to obtain the target compounds by synthesis of pyrazole skeleton (2), various General methods described in Japan patent JP-A-10-338676, but the method represented by reaction scheme 9, is an example of a preferred method.

Agent for pest control, containing the compound of the present invention as an active ingredient, has an impact in the fight against pests such as insects and mites, and is effective to deter, to the exclusion of pests and to control them in a great many cases, for example in agriculture, forestry, livestock, fisheries and for the conservation of the products of these industries, and in public health.

In particular, the compound of the present invention exhibits an excellent effect as an insecticide and acaricide for use in deterrence and exclusion of pests and their control in agriculture, forest management is iste and the like, in particular, pests, damaging agricultural crops during their growth, harvest, trees, ornamental plants, and the like, and pests in cases of health.

Specific cases of application, target pests, application methods and the like described below, but the present invention is not limited to them. Moreover, the target pests are not limited to those specifically described, and pests include adult stage, larvae, eggs and the like.

(A) Cases, including agriculture and forestry

Agent for pest control, containing the compound of the present invention as an active ingredient, is effective to deter pests and to deal with such pests as arthropods, mollusks, nematodes, various fungi, and the like, which damage agricultural crops such as food crops (e.g. rice, oats, corn, potatoes, sweet potatoes, beans), vegetables (e.g., mustard (brassicaceous) culture, pumpkin, eggplant, tomatoes, onions), fruit trees (e.g. citrus, apples, grapes, peaches), processed industrially plants (such as tobacco, tea, sugar beets, sugar cane, cotton, olives), culture for pasture and fodder (for example the EP, eucalyptus, grass pastures, green), ornamentals (e.g., grass, lawn, flowers and flowering plants, garden trees) during the growth of these crops. In addition, the compound of the present invention is also effective to deter pests and to control them when storing the collected fruits of the above crops, such as grains, fruits, nuts, spices and tobacco, and products obtained when they are subjected to processing, such as drying or grinding. In addition, the connection is also effective to protect living trees, fallen trees, processed logs, wood stock from damage by pests such as termites or beetles.

Specific examples of pests that belong to Arthropoda, Mollusca and Nematoda are described below. Examples of Arthropoda Insecta are described below.

Examples of Lepidoptera include Noctuidae, such as Leucania unipuncta, Heliothis assulata, Barathra brassicae, and Plusia peponis; Putellidae, such as Plutella xylostella; Tortricidae such as Homona magnanima and Grapholita molesta; Psychidae, such as Canephora asiatica; Review, such as Lyonetia clerkella; Lithocolletidae, such as Lithocolletis ringoniella; Acrolepiidae, such as Acrolepia alliella; Aegeriidae, such as Aegeria molybdoceps; Heliodinidae, such as Kakivoria flavofasciata; Gelechiidae such as Pectinophora gossypiella; Carposinidae such as Carposina nipponensis; Heterogeneidae, such as Cnidocampa flavescens; Pyralidae such as Cnaphalocrocis medinalis, Chilo suppressalis and Natarcha derogate; Hesperiidae, such as Parnara quttata Papilionidae, such as Papilio machaon); Pieridae such as Pieris rapae; Lycaenidae, such as Lampides boeticus; Geometridae, such as Ascotis selenaria cretacea; Sphingidae, such as Herse convolvuli; Notodontidae, such as Phalera flavescens; Lymantriidae such as Euproctis subflava; Arctiidae such as Hyphantria cunea; and the like.

Examples of Coleoptera include Scarabaeidae such as Anomala cuprea, Oxycetonia jucunda and Popillia japonica; Buprestidae, such as Agrilus auriventris; Elateridae, such as Melanotus legatus; Coccinellidae, such as Epilachna vigintioctopunctata; Cerambycidae, such as Anoplophora malasiaca and Xylotrechus pyrrhoderus; Chrysomelidae, such as Aulacophora femoralis, Phyllotreta striolata and Donacia provostii; Attelabidae, such as Phynchites heros; Brenthidae, such as Cylas formicarius; Curculionidae, such as Curculio sikkimensis and Echinocnemus squameus; and the like.

Examples Hemiptera include Pentatomidae, such as Plautia stali and Halyomorpha halys; Urostylidae, such as Urochela luteovaria; Coreidae, such as Cletus punctiger; Alydidae, such as Leptocorisa chinensis; Pyrrhocoridae, such as Dysdercus cingulatus; Tingidae, such as Stephanitis nashi; Miridae, such as Deraeocoris amplus; Cicadidae, such as Platypleura kaempferi; Aphrophoridae, such as Dophoara vitis; Tettigellidae, such as Oniella leucocephala; Cicadellidae, such as Arhoridia apicalis and Empoasca onukii; Deltocephalidae, such as Nephotettix cincticeps; Delphacidae, such as Laodelphax striatellus and Nilaparvata lugens; Flatidae, such as Geisha distinctissima; Psylloidae, such as Psylla pyrisuga; Aleyrodidae, such as Trialeurodes vaporariorum and Bemisia argentifolii; Phylloxeridae, such as Moritziella costaneivora; Pemphigidae, such as Eriosoma lanigera; Aphididae, such as Aphis gossypii, Myzus persicae and Rhopalosiphum rufiabdominalis; Margarodidae, such as Icerya purchasi; Pseudococcidae, such as Planococcus citri; Cocidae, such as Ceroplastes rubens; Diaspididae, such as Quadraspidiotus perniciosus and Pseudaulacaspis pentagana; and the like.

Examples Thysanoptera include Thripidae such as Frankliniella occidentalis, Scirtothrips dorsalis, Thrips palmi; Phlaeothripidae, such as Ponticulothrips diospyrosi and Haplothrips aculeatus; and the like.

Examples Hymenoptera include Tenthredinidae, such as Athalia japonica; Argidae, such as Arge mali; Cynipidae, such as Dryocosmus kuriphilus; Megachilidae, such as Megachile nipponica; and the like.

Examples Dioptera include Keys such as Asphondylia sp.; Tephiridae, such as Zeugodacus cucurbitae; Ephydridae, such as Hydrellia griseola; Drosophilidae, such as Drosophila suzukii; Agromyzidae, such as Chromatomyia horticola and Liriomyza trifolii; Anthomyiidae such as Hylemya antiqua; and the like.

Examples of Orthoptera include Tettigoniidae, such as Homorocoryphus nitidulus; Gryllidae, such as Calyptotrypes hihinonis; Gryllotalpidae, such as Gryllotalpa africana; Acrididae, such as Ochoa japonica; and the like.

Examples of Collembola include Sminthuridae, such as Sminthurus viridis; Onychiuridae, such as Onychiurus matsumotoi; and the like.

Examples Isoptera include Termitidae, such as Odontotermes formosanus, and the like. Examples of Dermaptera include Labiduridae, such as Labidura riparia, and the like.

Examples of Arthropoda Crustacea and Arachnida are described below.

Examples of Crustacea Isopoda include Armadillidiidae, such as Armadillidium vulgare, and the like.

Examples of Arachnida Acarina include Tarsonemidae such as Hemitarsonemus latus and Tarsonemus pallidus; Eupodidae, such as Penthaleus major; Tenuipalpidae, that is their as Brevipalpus lewisi; Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi; Eriophyidae such as Aculus pelekassi, Aculus schlechtendali and Eriophyyes chibaensis; Acaridae such as Tyrophagus putrescentiae; and the like.

As Mollusca Gastropoda, examples Gastropoda Mesogastropoda include Pomacea canaliculata and the like. Examples Stylommatophora include Achatina fulica, Incilaria bilineata, Milax gagates, C limax vaginal maximus, Acusta despecta, and the like.

Examples Nematoda Secernentea and Adenophorea described below.

Examples of Secernentea Tylenchida include Anguinidae, such as Ditylenchus destructor; Tylenchorhynchidae, such as Tylenchorhynchus claytoni; Pratylenchidae, such as Pratylenchus penetrans and Pratylenchus coffeae; Hoplolaimidae, such as Helicotylenchus dihystera; Heterodehdae, such as Heterodera rostochiensis; Meloidogynidae, such as Meloidogyne incognita; Criconematidae, such as Criconemoides; Nothotylenchidae, such as Nothotylencus acris; Aphelenchoidae, such as Aphelenchoides fragariae; and the like.

Examples Adenophorea Dorylaimida include Longidoridae, such as Xiphinema americanum; Trichdoridae, such as Paratrichodorus porosus; and the like.

In addition, the compound of the present invention is also effective to deter pests, pest control, exclusion of pests, damaging natural forest, artificial forest, trees in urban areas of green space or affect them, and the like. In this case, specific pests are described below. Examples of Arthropoda Insecta and Arachnida are described below.

Examples of Lepidoptera include Lymantriidae such Dasychira argentata and Lymantria disper japonica; Lasiocampidae, such as Dendrolimus spectabilis and Malacosoma neustria; Pyralidae such as Dioryctria abietella; Noctuidae, such as Agrotis fucosa; Tortricidae such as Ptycholomoides aeriferana, Laspeyresia kurokoi, and Cydia cryptomeriae; Arctiidae such as Hyphantria cunea; Nepticulidae, such as Stigmella malella; Heterogeneidae, such as Parasa consocia; and the like.

Examples of Coleoptera include Scarabaeidae such as Anomala rufocuprea and Heptophylla picea; Buprestidae, such as Agrilus spinipennis; Cerambycidae, such as Monochamus alternates; Chrysomelidae, such as Lypesthes itoi; Curculionidae, such as Scepticus griseus and Shirahoshizo coniferae; Rhynchophoridae, such as Sipalinus gigas; Scolytidae, such as Tomicus piniperda and Indocryphalus aceris; Bostrychidae, such as Rhizopertha dominica; and the like.

Examples Hemiptera include Aphididae, such as Cinara todocola; Adelgidae, such as Adelges japonicus; Diaspidiae, such as Aspidiotus cryptomeriae; Coccidae such as Ceroplastes pseudoceriferus; and the like.

Examples Hymenoptera include Tenthredinidae, such as Pristiphora erichsoni; Diprionidae, such as Nesodiprion japonica; Cynipidae, such as Dryocosmus kuriphilus; and the like.

Examples Dioptera include Tipulidae, such as Tipula aino; Anthomyiidae such as Hylemya platura; Cecidomyiidae, such as Contarinia inouyei and Contarinia matsusintome; and the like.

Examples of Arachnida Acaria include Oligonychus hondoensis, Oligonychus unuguis and the like.

Examples Nematoda Secernentea Tylenchida include Paracytaphelenchidae, such as Bursaphelenchus xylophilus, and the like.

Agent for pest control, containing the compound of the present invention as an active ingredient, which can be used in the form of any drug or in any usable form, prepared by using a drug that is effective in the cases mentioned above, related to agriculture or forestry, by itself or in combination, or in the form of a mixed drug together with other active compounds, such as insecticides, acaricide, nematicide, fungicide, synergist, plant growth regulator, herbicide, and toxic dressing. Specific examples of the above other active compounds are described below, but are not limited to this.

As active compounds, such as insecticides or acaricides, examples of organophosphorus agents include dichlorvos, fenitrothion, Malathion, naled, chlorpyrifos, diazinon, tetrachlorvinphos, fenthion, isoxathion, mitigation, salicion, Arafat, demeton-S-methyl, disulfoton, monocrotophos, azinphos-methyl, parathion, fosalan, pirimiphos-methyl and prothiofos. Examples of urethane agents include metolcarb, fenobucarb, propoxur, carbaryl, ethiofencarb, pirimicarb, bendiocarb, carbosulfan, carbofuran, methomyl, thiodicarb, and the like. Examples of organochlorine agents include lindane, DDT, endosulfan, Aldrin, chlordan and the like. Examples of PYRETHROID agents include permethrin, cypermethrin, deltamethrin, cigalotrin, cyfluthrin, acrinathrin, fenvalerate, etofenprox, selflove, fluvalinate, flucythrinate, Biff is trine, allethrin, phenothrin, fenpropathrin, cyphenothrin, permethrin, resmethrin, transferrin, prallethrin, flufenamic, halftracks, imiprothrin and the like. Examples neonicotinoids agents include Imidacloprid, nitenpyram, acetamiprid, dinotefuran, thiamethoxam, thiacloprid, clothianidin and the like.

Examples of insect growth regulators, such as phenylbenzophenone include diflubenzuron, chlorfluazuron, triflumuron, flufenoxuron, hexaflumuron, lufenuron, teflubenzuron, buprofezin, tebufenozide, chromafenozide, methoxyfenozide, cyromazine, and the like.

Examples of agents based on the juvenile hormones include pyriproxyfen, fenoxycarb, methoprene, hydroprene, and the like.

Examples of insecticidal substances produced by microorganisms include abamectin, milbemectin, nikkomycin, emamectin benzoate, ivermectin, spinosad and the like.

Examples of other insecticides include cartap, bensultap, chlorfenapyr, diafenthiuron, nicotine sulfate, metaldehyde, fipronil, pymetrozine, indoxacarb, toppenberg, pyrazolyl and the like.

Examples of acaricides include dicofol, venezolanos, Bancomat, tetradifon, polydactyly, amitraz, propargite, the oxide penbutolol, hydroxide tricyclohexyl, tebufenpyrad, pyridaben, fenpyroximate, pyrimidifen, fenazaquin, clofentezine, g is xaliasx, acehenese, chinomethionat, fanatical, etoxazole, bifenazate, flociprin and the like.

Examples of active compounds of nematicides include methyl isocyanate, fosthiazate, oxamyl, resolvents, cadusafos and the like.

Examples of toxic fertilizers include monohloruksusnoj acid, warfarin, coumatetralyl, diphacinone and the like.

Examples of active compounds, fungicides include inorganic copper compounds, organic compounds of copper, sulfur, MANEB, thiram, thiadiazin, Captan, CHLOROTHALONIL, iprobenfos, thiophanate methyl, benomyl, thiabendazole, iprodione, procymidone, pencycuron, metalaxyl, sandhofen, Breton, triflumizole, fenarimol, triforine, dithianon, triazine, fluazinam, provenzal, dietphenterm, isoprothiolane, pyroxylin, iminoctadine acetate, elemetal, dazomet, kresoxim methyl, cropropamide, diclocil, tricyclazole, provenzal, ipconazole, AZOXYSTROBIN, metamyosyn, acibenzolar-S-methyl, phenoxyl connection code No. NNF-9850 (Nihon Nohyaku Co., Ltd.), connection code No. BJL-003 (BASF), a compound represented by the code № DF-391 (Dainippon Ink &Chemicals, Incorporated), and the like.

Examples of active compounds synergists include bis(2,3,3,3-tetrafluoropropyl) a simple ester, N-(2-ethylhexyl)bicyclo[2,1,1]hept-5-ene-2,3-dicarboximide, α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-prop is toluol and the like.

Examples of active compounds of herbicides include bialaphos, sethoxydim, trifluralin, mefenacet and the like. Examples of active compounds of plant growth regulators include introcaso acid, ethephon, 4-CPA, and the like.

Examples of active compounds of repellents include Karan-3,4-diol, N,N-diethyl-m-triamide (Deet), limonene, linalool, citronellal, Menton, hinokitiol, menthol, geraniol, eucalyptol and the like.

Agent for pest control according to the present invention can be used in any form, and the compound of formula (1) is prepared together with auxiliary substances for pesticides, to obtain drugs, such as wettable powders, wettable granules, aqueous solutions, emulsions, liquids, flowing agents, including suspension in water emulsions in water, capsules, powdered drugs (Farrukh Dustov), pellets and sprays, which are then used. The preparations can contain any amount of the active ingredient compounds such as the compound of the present invention, but usually the content is selected in the range from 0.001 to 99.5 wt.%, as the total number of active ingredients, the decision is taken accordingly, in accordance with various conditions such as the form of the drug and the method of its application. For example, it is preferable to produce p is aparaty thus, to the content of the active ingredients was in the range of from about 0.01 to 90 wt.%, preferably from 1 to 50 wt.%, in wettable powders, wettable granules, aqueous solutions, emulsions, liquids, flowing agents, capsules and the like; from about 0.1 to 50 wt.%, preferably from 1 to 10 wt.%, in pulverulent preparations and granules; or from about 0.001 to 20 wt.%, preferably from 0.01 to 2 wt.%, in aerosols, and the like.

Auxiliary substances for pesticides used for the purpose of improving repellent effect, the overwhelming effect and preemptive action against pests, improve stabilization and dispersive ability of the pigment, and the like. Examples include carriers (diluents), wetting agents, emulsifiers, wetting agents, dispersants and leavening agents. Liquid carriers include water; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, butanol and glycol; ketones, such as acetone; amides such as dimethylformamide; sulfoxidov, such as dimethyl sulfoxide; methylnaphthalene; cyclohexane; animal or vegetable oils; fatty acids; and the like. Solid carriers include clay, kaolin, talc, diatomaceous earth, silicon oxide, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, aluminum oxide, sawdust, nitrocellulose, starch, resin drag the Kant and the like. As emulsifiers or dispersants can be used conventional surfactants. For example, usable are anionic, cationic, nonionic or amphoteric surfactants such as sulfates of sodium, higher alcohols, steartrimonium chloride, polyoxyethylene alkylphenolate ethers, and lauryl betaine. In addition, can be used wetting agents, such as polyoxyethylene nonylphenols simple ether and polyoxyethylene auriferous simple ether; such wetting agents are dialkyl sulfosuccinate; fixing agents, such as carboxymethyl cellulose and polyvinyl alcohol; and leavening agents such as sodium lignin sulfonate and sodium lauryl sulfate.

For example, in the case of wettable powders, bulk powder is prepared by mixing the compounds of formula (1) as an active ingredient with a solid carrier, a surface-active substance, and so forth, and bulk powder may be applied after dilution when using up to a prescribed concentration with water. In the case of emulsions, the amount of liquid or emulsion is prepared by mixing the above compounds as the active ingredient with solvents, surface-active agent and the like, and the volume of liquid can bitnaneun after dilution when using to the desired concentration with water. In the case of powdered drugs (dust) powdered drug is prepared by mixing the above compounds as the active ingredient with a solid carrier, and the like, and it can be used as such. In the case of granules, the granules are prepared by mixing the above compounds as the active ingredient with a solid carrier, a surface-active agent and the like, followed by granulation. The granules may be used as such. Methods for preparing the above-described preparations of various forms not limited to the above methods, and specialists in this field can optionally select the appropriate method, depending on the type of active ingredient, application and the like.

Usage varies depending on the type and number of pests and species, forms of cultivation and the state growth target plants, trees and the like, but against arthropods, gastropods, nematodes and similar products can generally be applied when the amount of the active ingredient, in the range of 0.1 to 1000 g, preferably from 1 to 100 g, 10 ar, on the area where the damage due to pests or where predicting the occurrence of the damage.

As for the specific method of application, the criminal code is mentioned above wettable powders, wettable granules, aqueous solutions, emulsions, liquids, flowing agents, including suspension in water emulsions in water, capsules and the like can be diluted with water and sprayed on plants, trees and the like in amounts in the range of 10 to 1000 liters per 10 ar, depending on the type, form of cultivation and the state growth target plants, trees and the like.

In addition, in cases of pulverulent preparations, granules and aerosol preparations can be applied as such on plants, trees and the like, within the limits described in the above usage.

In the case when the target pests mainly damage plants, trees and the like in the soil, wettable powders, wettable granules, aqueous solutions, emulsions, liquids, flowing agents, including suspension in water emulsions in water, capsules and the like, may be, for example, diluted with water and applied, in General, in number, in the range of 5 to 500 liters per 10 ar. At this time, the drugs can be sprayed on the soil surface, uniformly, across the field, where they should be applied, or the soil can be watered. When drugs are powdered drugs or granules, drugs as they can uniformly sprayed on the soil surface throughout the area where they will apply the Xia. In addition, when spraying or watering drugs can be applied only in the vicinity of seeds, plants, trees and the like, which must be protected from damage by pests, or soil can be processed by the cultivator during spraying or after him, to dispersing the active ingredient mechanically.

The occurrence of the disease and the appearance of pests can also be suppressed over a long period of time through the use of the compounds of the present invention for coating seeds and sowing. As a concrete method, the seeds are covered wettable powder, Sol or powdered product prepared in such a way that it contains the compound of the present invention, applied to the moistened seeds. In this case, wettable powder, Sol or powdered drug is preferably used in an amount of from 1 to 1000 g, preferably from 10 to 200 g per 100 g of seeds. When sown in the usual way seeds with coating, thus prepared, can be prevented not only the damage caused by pests in the soil, but also stems, leaves, flowers and fruits of plants, after their growth, can be protected from damage by pests.

Moreover, as methods for using the compounds of the present invention when planting, as examples, privadas the following ways. Granules containing the compound of the present invention, are mixed with the soil for planting, the soil is placed in the seed bed. Over time, the soil in which the deposited granules, can be used only as a ground for the bottom layer of the seed beds, the soil, which made pellets, can be used only for the top layer of the soil seed beds, or the soil may be used for the bottom soil layer and the top layer of the soil. In this case, the granules are preferably used in quantities of from 0.1 to 100 g, more preferably from 1 to 50 g per 1.0 kg of soil. Moreover, after the lower layer of soil is placed in the seed bed, the granules containing the compound of the present invention, can be made using the method of dispersing them around the place where sown the seeds, or by using a method of dispersing the granules in place, covered with soil after sowing. In this case, the granules are generally used in amounts of, preferably, from 1 to 1000 g, more preferably from 10 to 100 g, per capacity seed box (usually, one container (box) seed box corresponds to 0.5 and, at a fixed landing). In this regard, wettable powder, powdered drug or the like may be used instead of granules with similar applications.

In addition, the as methods for using the compounds of the present invention, from seed germination to commit seedlings (the period of the formation of the green shoots), as agent for use in crates, the following methods can be cited as examples.

Granules containing the compound of the present invention, are made in the seed box by their dispersion. Typically, pellets are generally used in amounts of preferably from 1 to 1000 g, more preferably from 10 to 100 g, per box seed box (usually one box seed box corresponds to 0.5 and at a fixed landing).

Moreover, in the case of emulsions of liquid or Sol (flowable agent) and the preparation of microcapsules they can be used by watering the seed box as such or after dilution with water. In the case of wettable powders, wettable granules, aqueous solution and an aqueous solution of granules, they can be used by watering the seed box after dilution with water. In this case, they are generally used in amounts of preferably from 1 to 1000 ml, more preferably from 10 to 100 ml, per box seed box (usually one box seed box corresponds to 0.5 and at a fixed landing).

In the case of protection described above living trees, fallen trees, processed logs stored wood from damage the pests, such as termites or beetles, methods of spraying, injection, irrigation or application of oil solution, emulsion, wettable powder or Sol or dispersion of the agent in the form of a powdered drug or granules, are given as examples. In such cases, the agent for pest control, containing the compound of the present invention as an active ingredient, can be used by itself or in combination, or in the form of a mixed drug together with other active compounds, such as insecticides, acaricide, nematicide, fungicide, repellent and a synergist.

The preparations can contain any amount of the active ingredient, such as a compound of the present invention, but usually the content is in the range from 0.0001 to 95 wt.%, as the total number of active ingredients. It is preferable that the active ingredient contained in amounts of 0.005 to 10 wt.% in oil solutions, powdered preparations, granules and the like in an amount of from 0.01 to 50 wt.% in emulsions, wettable powders, sols, and the like. Specifically, in the case of the displacement of termites or beetles, or struggle with them, the drugs can be sprayed on the soil surface or of logs and timber in the amount of from 0.01 to 100 g per 1 m2as the number of the active ingredient.

(C) cases Such as industrial is Eredivisie livestock and fishing industry

Agent for pest control, containing the compound of the present invention as an active ingredient, is effective to deter, to the exclusion of pests such as arthropods, nematodes, trematodes, cestodes and protozoa, which are internal or external parasites in animals and Pets arising from industrial livestock rearing, fisheries and dwellings, and which cause direct damage, such as destruction of the skin, or the like, and suck the blood or cause such damage as the disease spread, and control, and the agent can be used for prevention and treatment of diseases associated with these pests.

Target animals include vertebrates such as livestock, including cattle, sheep, goats, horses, pigs, and the like, and farmed fish; animals and experimental animals, such as poultry, dogs, cats, and the like, rodents, including mice, rats, hamsters, squirrels, and the like, Carnivora, including ferrets, and the like, fish, and the like.

Among the pests, examples of Arthropoda Insecta and Arachnida are described below. Examples Diptera include Tabanidae such as Chrysops japonica, Simulium iwatens, and Tabanus trigonus; Muscidae such as Ophyra leucostoma, Musca domestica and Stomoxys calcitrans; Gasterophlidae, such as Gasterophilus intestinalis; Hypodermidae, such as Hypoderma bovis; Calliphoridae, such as Phaenicia cuprina; Phoridae, such as Megaseria spiracularis; Sepsidae, such as Sepsis monostigma; Psychodidae, such as Telmatoscopus albipunctatus and Psychoda alternata; Culicidae, such as Anopheles hyrcanus sinensis, Culex tritaeniorhynchus and Aedes albopictus; Simuliidae, such as Prosimulium hirtipes; Ceratopogonidae, such as Culicoides oxystoma and Culicoides arakawai; and the like.

Examples Siphonaptera include Pulicidae, such as Ctenocephalides felis and Ctenocephalides canis, and the like.

Examples Anoplura include Echinophthiriidae, such as Haematopinus suis and Haematopinus eurysternus; Trichodectidae, such as Damalinia equi; Linognathidae, such as Linognathus vituli; Menoponidae, such as Menopon gallinae; and the like.

Examples of Arthropoda Arachnida Acarina include Ixodidae such as Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, and Aroblyomma testudinarium; Macronyssidae, such as Ornithonyssus sylviarum; Dermanyssidae such as Dermanyssus gallinae; Demodicidae, such as Demodex suis; Sarcoptidae, such as Notoederes cati and Sarcoptes sylvianum; Psoroptidae, such as Otodectes cynotis and Psoroptes bovis; and the like.

Examples Nematoda Phasmidia described below.

Examples Strongylida include Ancylostoma, Stephanurus dentatus, Metastrongylus elongatus, Trichostrongylus, the recommended dose rate, and the like. Examples Ascarida include Ascarus lumbricoides, Parascaris equorum, and the like.

Examples Platyhelminthes Trematoda include Schistosoma japonicum, Fasciola hepatica, Paramphistomum cervi, Paragonimus westermanii, Prosthogonimus japonicus and the like.

Examples Cestoda include Anoplocephala perfoliata, Moniezia expansa, Moniezia benedeni, Raillietina tetragona, Raillietina sp., Raillieina cesticillus and the like.

Examples of Protozoa Mastigophoca include Histomonas and the like Rhizomastigida; Leishmania, Trypanosoma, and the like, as Tripanpsomidae; Giardia and the like Polymastigida; and Trichomonas, and the like, as Trichomonadia.

In addition, examples of Sarcodina Amoebida include Entamoeba, and the like. Examples Sporozoa Piroplasmea include Theilaria, Babesia, and the like. Examples Telosporidia include Eimeria, Plasmodium, Toxoplasma, and the like.

Agent for pest control, containing the compound of the present invention as an active ingredient, can be used in the form of any drug or any usable form, prepared by using a drug that is effective in the above applications in agriculture or forestry, by itself, or in combination, or as a mixed preparation with other active compounds, such as insecticides, acaricide, nematicide, fungicide, synergist, plant growth regulator, herbicide or toxic dressing. Substances discussed in section(A), cases Such as agriculture and forestry, are cited as specific examples of the above other active compounds, but they are not limited to this.

Specific applications include incorporation into feed for livestock, Pets and the like; in oral administration in the form according to stuudy swallow oral compositions prepared, for example, tablets, pills, capsules, paste, gel, drink, medicated feed, medicinal drink, drug nutritional supplements, a large tablet with a slow release or sustained-release, which must persist in the gastrointestinal tracts containing a pharmaceutically acceptable carrier and the substance of the coating; and means for applying to the skin, such as a spray, a powder, a thick ointment, cream, ointment, emulsion, lotion, medication for local application, the preparation for the dive, shampoo, or something like that.

As methods for applying on the skin and for local application device (for example, collars, medallions and stickers on the ears) are attached to the animals so that they could be used, local or systemic, for combating arthropods.

Specific methods for oral introduction and application on the skin, in the case of worms, for livestock and domestic animals are described below, but in the present invention, methods of application are not limited to.

In the case of oral administration in the form of a medicinal drink suspension or dispersion can usually be obtained by dissolving the active ingredient in the corresponding non-toxic solvent or in water together with suspenders agent such as Bento is it a wetting agent, or with other fillers, and may contain protivovspenivayushchie agent, if necessary. The drink usually contains the active ingredient in an amount of from 0.01 to 1.0 wt.%, preferably from 0.01 to 0.1 wt.%.

In the case of oral administration in the form of standard dosage forms dried solid product is typically used capsule, pill or tablet containing a given amount of the active ingredient. These are suitable for use forms can be prepared by homogeneous mixing of the active ingredient with crushed appropriate diluent, filler, baking powder and/or binders such as starch, lactose, talc, magnesium stearate and vegetable resin, and the like. In the preparation of such unit dosage forms, the number and content of remedy against worms may optionally be determined depending on the form of an animal host that is being treated, the extent of spread of infection, a parasite and body weight of the host.

In case of introduction in the form of food can be considered the ways in which the connection of the active ingredient is homogeneous dispersed in the stern, the agent is used as a seasoning or in the form of flakes. To achieve impact against worms connection active ingredient contained in con cnom stern in the amount of from 0.0001 to 0.05 wt.%, preferably from 0.0005 to 0.01 wt.%.

In the case of a solution or dispersion of the filler in a liquid carrier, the drugs can be administered to animals parenterally, by proventricular or intramuscular, endotracheal or subcutaneous injection. For parenteral administration, the compound of the active ingredient preferably is mixed with a vegetable oil such as peanut oil or cottonseed oil. In this preparation, the connection of the active ingredient, as a rule, is contained in an amount of from 0.05 to 50 wt.%, preferably from 0.1 to 0.2 wt.%.

Moreover, the drug is mixed with a carrier, such as an aliphatic alcohol, a hydrocarbon solvent or the like, can be applied directly and locally superficially on livestock or domestic animals by spraying or pouring. In this preparation, the connection of the active ingredient, as a rule, is contained in an amount of from 0.05 to 50 wt.%, preferably from 1 to 20 wt.%. Also, in this case, in order to prevent precipitation of the active ingredient, it is preferred that the drug contained agents that inhibit crystallization, such as surface-active substances and agents, film forming.

By incorporating the active ingredient in the source material products for pest control,such as the collar and ear stickers, it can also indirectly be introduced livestock and domestic animals. In this case, the connection of the active ingredient, as a rule, is contained in an amount of from about 0.1 to 40 wt.%, preferably from about 1 to 15 wt.%. The source material may optionally be selected depending on the usable forms, and examples include a stamped articles of thermoplastic resins such as vinyl chloride resin and woven articles made of textile products such as cotton and polyester.

(C) Such cases as health

Agent for pest control, containing the compound of the present invention as an active ingredient is also effective to deter, to the exclusion of pests and their control in health care, where they adversely affect the environment, food, clothing and shelter, or to further damage the human body, or carry or carry pathogens, to maintain conditions suitable for health. Specifically, the agent for pest control according to the present invention is effective against Lepidoptera, beetles, book worms, cockroaches, fleas and ticks, which damage the house by themselves and logs inside or outside the house, woodwork, such as wood which I furniture, stored food, clothing, books, products of animal origin (leather, fur, wool, feathers and the like), products of vegetable origin (clothing, paper and the like), and the like, and has a negative impact on healthy life, and to deter them and displacement. Specific examples of pests for such cases of public health are described below.

Examples of Arthropoda Insecta described below. Examples of Lepidoptera include Lymantriidae such as Euproctis similis; Lasiocampidae, such as Dendrolimus undans flaveola; Heterogeneidae, such as Parasa consocia; Zygaenidae, such as Artona funeralis; Pyralidae such as Cadra cautella, Ephestia cautella and Plodia interpunctella; Gelechiidae such as Sitotroga cerearella; Tineidae such as Tinea pellionella and Tineola bisselliella; and the like.

Examples of Coleoptera include Oedemeridae, such as Xanthochroa vaterhousei; Meloidae, such as Epicauta gorhami; Staphylinidae, such as Paederus fuscipes; Rhynchophoridae, such as Sitophilus zeamais and Sitophilus oryzae; Bruchidae, such as Callosobruchus chinensis, Bruchus pisorum and Bruchus rufimanus; Tenebrionidae such as Triboliuim castaneum; Cucujidae, such as Oryzoephilus surinamensis and Placonotus testaceus; Anobiidae, such as Lasioderma serricorne and Stegobium paniceum; Dermestidae, such as Attagenus unicolor, Anthrenus verbasci and Dermestes maculatus; Ptinidae, such as Gibbium aeguinoctiale; Bostrychidae, such as Dinoderus minutus and Rhizopertha dominica; Lyctidae, such as Lyctus brunneus; and the like.

Examples Hymenoptera include Vespidae such as Vespa mandarinia; Formicidae, such as Brachyponera chinensis; Pompilidae, such as Batozonellus annulatus; and t the th similar.

Examples Diptera include Culicidae, such as Aedes jaonica; Ceratopogonidae, such as Culicoides sp.; Chironomidae, such as Chironomus dorsalis; Simuliidae, such as Simulium aokii; Tabanidae such as Chrysops japonicus; Muscidae such as Musca domestica; Anthomyiidae such as Fannia canicularis; Calliphoridae, such as Phormia regina; Sarcophagidae, such as Boettcherisca peregrina; Drosophilidae, such as Drosophila virilis; Piophilidae, such as Piophila casel; and the like.

Examples Siphonaptera include Pulicidae, such as Pulex irritans, and the like.

Examples of Collembola include Neogastruridae, such as Neogastruna communis, and the like.

Examples Blattaria include Blattellidae, such as Blattela germania and Asiablatta kyotensis; Blattidae, such as Periplaneta americana, Periplaneta fuliginosa and Periplaneta japonica; and the like.

Examples of Orthoptera include Gryllacridoidea, such as Diestrammena japonica and Steropelmatidae, and the like.

Examples Anoplura include Pedicuilidae, such as Pediculus humanus capitis; Pthiridae, such as Pthirus pubis; and the like.

Examples Hemiptera include Cimicidae, such as Cimex lectularius; Reduriidae, such as Isyndus obscurus; and the like.

Examples Isoptera include Phinotermitidae, such as Reticulitermes speratus and Coptotermes formosanus; Kalotermitidae, such as Cryptotermes domesticus; and the like. Examples of Psocoptera include Trogiidae, such as Lepinotus reticulatus; Liposcelidae, such as Liposcelis bostrichophilus; and the like. Examples Thysanura include Lepismatidae, such as Ctenolepisma villosa and Lepisma saccharina, and the like.

Examples of Arthropoda Arachnida opisyvayut is below.

Examples Acarina include Ixodidae such as Ixodes persulcatus; Macronyssidae, such as Ornithonyssus bacoti; Cheyletidae such as Chelacaropsis moorei; Pyemotidae, such as Pyemotes tritici; Demodicidae, such as Demodex folliculorum; Pyroglyphidae, such as Permatophagoides pteronyssius; Sarcoptidae, such as Sarcoptes scabiei; Trombiculidae, such as Leptotrombidum akamushi; Acaridae such as Tyrophagus putrescentiae and Lardoglyphus konoi; Carpoglyphidae, such as Carpoglyphus lactis; and the like.

Examples Araneae include Clubionidae, such as Chiracanthium japonicum; Heteropodidae, such as Heteropoda venatoria; Pholcidae, such as Spermophora senoculata and Pholcus phalangioides; Urocteidae, such as Uroctea compactilis; and Salticidae, such as Plexippus paykulli and Plexippus setipes; and the like.

Examples Scorpiones include Buthidae, such as Isometrus europaeus, and the like.

As other Arthropoda, examples Chilopoda Scolopendromorpha include Scolopendridae, such as Scolopendra subspinipes and Otostigmus multispinosus, and the like. Examples of Scutigeromorpha include Scutigeridae, such as Thereuonema hilgendorfi, and the like. Moreover, examples of Arthropoda Diplopoda Polydesmoidea include Strongylosomidae, such as Oxidus gracilis, and the like. Examples of Arthropoda Crustacea Isopoda include Oniscidae, such as Porcellio scaber, and the like. In addition, examples of Annelida Hirudinea Gnathobdellida include Haemadipsidae, such as Haemadipsa zeylanica japonica, and the like.

Agent for pest control, containing the compound of the present invention as an active ingredient, can be used as any pre the Arata or any usable form, obtained by using a drug that is effective in the above cases, health care, by itself or in combination, or as a mixed preparation with other active compounds, such as insecticides, acaricide, nematicide, fungicide, synergist, plant growth regulator, herbicide or toxic dressing. Substances discussed in section(A), cases Such as agriculture and forestry, are cited as specific examples of the above other active compounds, but they are not limited to this.

Suitable for use form agent for pest control according to the present invention can be any shape, and protection of the above products of animal origin and products of plant origin can be achieved by spraying an oil solution, emulsion, wettable powder, powdered drug or the like, placing the evaporating fogging agent-based resin, treatment with sadisuser agent or aerosol, placement of granules, tablets or toxic feeding, spraying aerosol or anything like that. The connection of the active ingredient, preferably, contained in the preparations in amounts of from 0.0001 to 95 wt.%.

Examples of the method of use against pests, for example, directly calling the damage arthropods, carrying diseases arthropods and the like, include ways of spraying, injection, irrigation and application of the oil solution, emulsion, wettable powder or the like, spraying powdered drug or the like, treatment with this drug, as a fumigant, mosquito coil, thermal spray, including zadilady agent snowspeeders type or chemically reactive aerosol zadilady agent, including misting, or ULV agent, and others. Also, for example, granules, tablets or toxic feeding can accommodate as other forms, or forms a dust in the air, powdered drug, granules or the like can be applied by adding them dropwise in the pipelines, wells, reservoirs, water tanks and other devices with running water or standing water.

In addition, Euproctis, which is also a pest in agriculture and forestry, can be controlled in a manner similar to the methods described in section (A), cases Such as agriculture and forestry". The way to enable the agent to fight to feed livestock, so that the manure contained the active ingredient is effective against fleas and method of evaporation in air using an electric spiral against the of schitov is also effective against mosquitoes.

Drugs that are suitable for use forms of drugs, can be represented as a mixed preparations together with the above-described other active compound, such as insecticide, acaricide, nematicide, fungicide, repellent or synergist, and the connection of the active ingredient, preferably, contained in these medications in the quantity of from 0.0001 to 95 wt.%, in General. In this connection is also possible using the drugs in combination with other used active connections.

In the case of the protection of homes, wooden furniture and the like, from damage by pests such as termites or beetles, can be considered ways of spraying, injection, irrigation or application of oil solution, emulsion, wettable powder or Sol or dispersion agent in the form of a powdered drug or granules inside houses, wooden furniture and the like, and near them. In such cases, the compound of the present invention can also be used by itself or in combination, or as a mixed preparation with other active compounds, such as insecticides, acaricide, nematicide, fungicide, repellent and a synergist.

Any number of connections active ingredient, such as a compound of the present invention, may contain drugs, but usually with the actual content is in the range from 0.0001 to 95 wt.% as the total number of active ingredients. It is preferred that the connections in the amount of 0.005 to 10 wt.% contained in oil solutions, powdered preparations, granules and the like in an amount of from 0.01 to 50 wt.% in emulsions, wettable powders, sols, and the like. Specifically, in the case of the displacement of termites or beetles, or struggle with them, the drugs can be dispersed near the surface or directly on it in the amount of from 0.01 to 100 g per 1 m2as the number of connections active ingredient.

When deterrence, displacement of the pests that harm the people or carry, or carry pathogens, and fight with them ways other than described above, may be considered oral administration in the form of a composition corresponding oral swallow medication, such as tablets, pills, capsules, paste, gel, drink, drug-food, drug drink, drug nutritional supplements, a large pill with a slow release, or delayed release, which must persist in the gastrointestinal tracts containing a pharmaceutically acceptable carrier and a substance for coating; and applying to the skin in the form of a spray, powder, thick ointment, cream, ointment, emulsion, lotion, medication for local application of the drug with water, shampoo or something similar.

Specific preparation can be performed in a manner similar to the methods described in section(C), cases Such as industrial livestock breeding and fisheries".

Examples

The present invention is explained in more detail with reference to examples, but the present invention is not limited to the following further examples, if they do not exceed the gist of it.

Example 1

Obtain 1-(2,6-dichloro-4-triptoreline)-4-formailty-5-(pyridine-4-ylmethylamino)pyrazole-3-carbonitrile (connection # 1):

To a mixture of 7.7 g of 5-amino-1-(2,6-dichloro-4-triptoreline)-4-formatiert-3-carbonitrile added to 2.2 g of 4-pyridinecarboxamide, 80 ml of toluene and 0.1 g of monohydrate p-toluensulfonate acid, and then heated under reflux for 10 hours while generated water is removed. After cooling to room temperature, to the mixture is added 30 ml of ice water, followed by extraction. The organic layer is dried over anhydrous sodium sulfate. The solvent is removed by distillation (distillation) under reduced pressure to obtain crude 1-(2,6-dichloro-4-triptoreline)-4-formailty-5-(pyridine-4-ylmethylamino)pyrazole-3-carbonitrile.

To a methanol solution (100 ml) thus obtained 1-(2,6-dichloro-4-triptoreline)-4-formailty-5-(pyridine-4-ylmethylamino)Piras the l-3-carbonitrile gradually add 0.4 g of sodium borohydride. After stirring at room temperature for 1 hour to the mixture add ice and ethyl acetate, followed by extraction. The organic layer was washed with saturated saline solution and then dried over anhydrous sodium sulfate. The residue is purified by column chromatography on silica gel, thus obtaining 7.6 g of the compound (No. 1), further described in the following table 1.

Melting point: 204°C.

1H NMR (CDCl3): to 4.41 (2H, d), and 4.68 (1H, t), of 5.39 (1H, s)to 5.56 (1H, s),? 7.04 baby mortality (2H, d), to 7.67 (2H, s), 8,49 (2H, d).

Example 2

Obtain 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile (connection # 2):

To a mixture of 8.0 g of 5-amino-1-(2,6-dichloro-4-triptoreline)-4-deformational-3-carbonitrile, 2.2 g of 2-pyridinecarboxamide add 60 ml of toluene and 20 mg of the monohydrate of p-toluensulfonate acid, and then heated under reflux for 3 hours, with the resulting water is removed. After cooling to room temperature, to the mixture is added 0.1 ml of triethylamine and 30 ml of ice water, followed by extraction. The organic layer is dried over anhydrous sodium sulfate. The solvent is removed by distillation under reduced pressure to obtain crude 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile.

To manolea solution (50 ml) thus obtained 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile gradually add 0.7 g of sodium borohydride. After stirring at room temperature for 1 hour to the mixture add ice and ethyl acetate, followed by extraction. The organic layer was washed with saturated salt solution, then dried over anhydrous sodium sulfate. The residue is purified by column chromatography on silica gel, thus obtaining a 8.4 g of the compound (No. 2), further described in the following table 1.

Melting point: 117-120°C.

1H NMR (CDCl3): of 4.57 (2H, d), 5,88 (1H, m), of 6.73 (1H, t), 7,19 (2H, t), 7,66 (1H, t), to 7.77 (2H, s), to 8.41 (1H, d).

Example 3

Compounds shown in table 1, are synthesized in accordance with methods described in examples 1 and 2.

No. of compounds and NMR data are presented below.

No. 3:

1H NMR (CDCl3): 4,47 (2H, d), of 4.67 (1H, users), 6,69 (1H, t), 7,05 (2H, d), 7,68 (2H, s), 8,51 (2H, d).

No. 4:

1H NMR (CDCl3): of 3.25 (2H, q), of 4.44 (2H, d), of 4.67 (1H, t),? 7.04 baby mortality (2H, d), to 7.64 (2H, s), 8,48 (2H, d).

Table 1
(R2=H, R3=H, X=C-Cl)
No. of connectionsSR1R4The position of substitutionTPL (°)
pyridine
1SCH2FH4-204
2SCHF2H2-117-120
3SCHF2H4-127-131
4SCH2CF3H4-164-167

Example obtain 1

Obtain 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile:

(1) In a three-neck flask is charged with 40 ml dry toluene, 10 g (31,1 mmol) 1-(2,6-dichloro-4-triptoreline)-5-aminopyrazole-3-carbonitrile, 4,55 g of 2-pyridinecarboxamide and 0.03 g of p-toluensulfonate acid and then refluxed under nitrogen atmosphere for 3 hours. After the above interaction, the solution washed three times with water, the organic phase is dried over magnesium sulfate. Then the magnesium sulfate is removed by filtration, and the solvent is removed by distillation, thus obtaining 12,63 g of 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile in the form of a solid product (purity: 98,6 LC%, 30.3 mmol, yield: 97.3 per cent).

(2) In a three-neck flask is charged with 2000 ml of dry methanol, 47,7 g (purity: 96%, by 109.9 mmol) 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-iletilerini is)pyrazole-3-carbonitrile and 2.0 g sodium tetrahydroborate, with the subsequent interaction in the atmosphere of nitrogen for 2 hours. After that formed in the reaction solution, the crystals are collected by filtration, washed with water and methanol, and then dried under vacuum, thus obtaining 42,84 g of 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile in the form of a solid product (purity: 97.5%of that of 101.3 mmol, yield: 84,1%).

Example of getting 2

Obtaining bis[1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(pyridine-2-ylmethylamino)pyrazole-4-yl]disulfide:

In test tube research load 1 ml of acetic acid, 3 ml of dry toluene, 200 mg (0,485 mmol) 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile and 40 mg monochloride sulfur (S2Cl2), with subsequent interaction in the atmosphere of nitrogen for 3 hours. After that formed in the reaction solution, the crystals are collected by filtration, neutralized with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate, and then separated from the liquid phase. Then the organic phase is dried over magnesium sulfate, the magnesium sulfate, and the ethyl acetate is removed by distillation, while receiving 200 mg of bis[1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(pyridine-2-ylmethylamino)pyrazole-4-yl)]disulfide (purity: 85,6%, rate of 0.193 mmol, yield: 79.7 per cent).

Example 4

Receiving the foster No. 2 using Chlorodifluoromethane:

In a 50 ml three-neck flask is charged with 500 mg (of 0.565 mmol) of bis[1-(2,6-dichloro-4-triptoreline)-3-cyano-5-(pyridine-2-ylmethylamino)pyrazole-4-yl]disulfide obtained using the method of example getting 2, and absolute ethanol (15 ml) under nitrogen atmosphere, then cooled to 3°C. To the mixture gradually add borohydride sodium (64 mg, 3.0 EQ.), under stirring. The mixture allow to stand for cooling to room temperature and stirred for 1 hour. After that, when the injection of Chlorodifluoromethane in the reaction solution tube to enter the gas in the reaction solution dropwise gradually add ethoxide sodium (192 mg, and 2.83 mmol, 5.0 equiv.) dissolved in 5 ml of absolute ethanol. After the interaction of the ethanol is removed by distillation, and to the mixture are added 20 ml of distilled water, followed by extraction with ethyl acetate (75 ml × 2). An ethyl acetate extracts are combined and the combined extract is washed with distilled water (30 ml) and dried over anhydrous magnesium sulfate. Then the magnesium sulfate, the ethyl acetate is removed by distillation, thus obtaining 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)-pyrazole-3-carbonitrile with the release of 64%.

Example 5

Receiving connection number 2 using diftormetilirovaniya:

The atmosphere is fere nitrogen 500 mg (1,21 mmol) 1-(2,6-dichloro-4-triptoreline)-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile suspended in 5.0 ml of dry dichloromethane, and to the mixture is added dropwise to 2.0 ml of dry dichloromethane containing 180 mg (of 1.52 mmol, 1.25 EQ.) diftormetilirovaniya, under stirring, at room temperature, with subsequent interaction within 2 hours. To the mixture are added ethyl acetate (100 ml)and the organic layer is successively washed with 20 ml saturated aqueous sodium bicarbonate solution and 20 ml of water, followed by drying over anhydrous magnesium sulfate. Then the magnesium sulfate, the solvent is removed by distillation under reduced pressure, and the crude product is recrystallized from a solvent mixture of hexane/ethyl acetate (3/1), while receiving 535 mg of 1-(2,6-dichloro-4-triptoreline)-4-deformality-5-(pyridine-2-ylmethylamino)pyrazole-3-carbonitrile (yield: 90%, purity: 96%).

Examples of the preparation of insecticides for agriculture and horticulture containing compound of the present invention as an active ingredient, are shown below, but usable forms of the present invention are not limited to.

Example composition 1

Wettable powder:

Twenty-mass parts of the compound of the present invention, 20 mass parts of Carplex #80 (white carbon black, produced Shionogi & Co., Ltd., trade name), 52 mass parts ST Kaolin Clay (kaolinite, is made by Tsuchiya Kaolin K.K., trade name the of), 5 mass parts of Sorpol 9047K (anionic surfactant, manufactured Toho Chemical Industry Co., Ltd., trade name) and 3 mass parts Runox P65L (anionic surfactant, manufactured Toho Chemical Industry Co., Ltd., trade name) are mixed and uniformly crushed, while receiving wettable powder containing 20 wt.% the active ingredient.

Example composition 2

Powdered drug (dust):

Two mass parts of the compound of the present invention, 93 mass parts of clay (manufactured by Nippon Talc K.K.) and 5 mass parts of Carplex #80 (white carbon black, produced Shionogi & Co., Ltd., trade name) are mixed and uniformly crushed, while receiving pulverized product containing 2 wt.% the active ingredient.

An example of a structure of 3

Emulsion:

In a solvent mixture of 35 mass parts of xylene and 30 mass parts of dimethylformamide is dissolved 20 mass parts of the compound of the present invention, and are added to a solution of 15 mass parts of Sorpol 3005X (a mixture of nonionic surfactants and anionic surfactants, is Toho Chemical Industry Co., Ltd., trade name), while receiving the emulsion containing 20 wt.% the active ingredient.

Example of part 4

Fluid agent:

Thirty-mass parts of the compound of the present invention, 5 mass h is the capacity of Sorpol 9047K, 3 mass parts Sorbon T-20 (nonionic surfactant, manufactured Toho Chemical Industry Co., Ltd., trade name), 8 mass parts of ethylene glycol and 44 mass parts of water are mixed and pulverized in a Dynomill (produced Shinmaru Enterprises Co.). To the resulting suspended mixture add 10 mass parts of a 1 wt.% aqueous solution of xanthan gums (natural polymer), followed by thorough mixing and grinding, while receiving fluid agent containing 20 wt.% the active ingredient.

Example of part 5

Pellet:

The two parts of the compound of the present invention, 40 parts of bentonite, 53 parts of clay and 5 parts of calcium ligninsulfonate mixed and uniformly crushed. Then, water is added, and the mixture was thoroughly mixed together, with stirring, the product ekstragiruyut and granularit, and the resulting product is dried and sorted by size, thus obtaining granules.

Example of compound 6

Granules:

After placing sand and silicon dioxide in a rotary granulator and hydration 2 parts of the compound of the present invention, 3 parts of calcium lignin sulfonate, 0.5 parts of polyvinyl alcohol (PVA), 0.5 parts of white carbon black and 94 parts of sand and silicon dioxide, which has previously been mixed and crushed, load it to create a cover, and then the obtained product is dried and sorted by size is, while receiving granules.

Example of compound 7

Granules from the seeds, covered with powdered preparation:

Powdered drug made by mixing and uniform grinding 2 parts of the compound of the present invention, 6 parts of calcium lignin sulfonate and 10 parts of polyvinyl alcohol, and 82 parts of clay are mixed with seeds soaked before that, and the mixture is dried in air, while receiving the seeds are coated.

Below are examples of studies of insecticides for agriculture and horticulture containing compound of the present invention as the active ingredient, but usable forms not limited to.

Example project 1

Insecticidal effect on larvae of brown rice cicadas (Nilaparvata lugens):

Rice seedlings are planted in a glass cylinder (inner diameter: 3 cm × length: 17 cm), and there freely placed five larvae of the 4th age Nilaparvata lugens. Insecticide for agriculture and horticulture of the present invention prepared in accordance with Example 3 and diluted with water, and 0.5 ml of the obtained diluted drug was dispersed in the above glass cylinder with irrigation device (produced Mizuho Rika) (twice, at the chosen concentration). The cylinder support in the room for the e with a constant temperature, at 25°and death and the agony of larvae examined 5 days after treatment, receiving mortality (%), given the moribund insects, such as1/2from a dead insect. The results obtained are shown in table 2 (the numbers of the compounds in the table correspond to the numbers in table 1).

Table 2
Connection # Concentration (ppm)Mortality (%)
1500100
2500100
3500100
4500100

Example research 2

Insecticidal effect on larvae of the cabbage moth (Plutella xylostella):

Disk (diameter: 6 cm)cut from the cabbage leaf, soaked for 1 minute in dilute water the insecticide for agriculture and horticulture of the present invention, prepared in accordance with Example 1, then dried in air and placed in a plastic Cup (inner diameter: 7 cm). Five larvae of the 3rd age Plutella xylostella freely placed in a Cup (twice, at the chosen concentration). The Cup is kept in a room with constant temperature at 25°and investigate the death and the agony is ichino 4 days after treatment, receiving mortality (%), given the moribund insects, such as1/2from a dead insect. The results are presented in table 3 (number of connections forth in the following table below correspond to the numbers in table 1).

Table 3
Connection # Concentration (ppm)Mortality(%)
1500100
2500100
3500100
4500100

Example research 3

Insecticidal effect on adult bean weevil (Callosobruchus chinensis):

Two Bob bean radiant placed in a glass cylinder (inner diameter: 3 cm × length: 15 cm), and there is a free place 10 adult Callosobruchus chinensis. Insecticide for agriculture and horticulture of the present invention prepared in accordance with Example 3 and diluted with water, and 0.3 ml of the obtained drug was dispersed in the above glass cylinder with a spray device (produced Mizuho Rika) (twice, at the chosen concentration). The cylinder is kept in a room with constant temperature at 25°and investigate the death and agony the larvae after 4 days after treatment, receiving mortality (%), given the moribund insects, such as1/2from a dead insect. The results obtained are presented in table 4 (number of connections in the table correspond to the numbers in table 1).

Table 4
Connection # Concentration (ppm)Mortality (%)
1500100
2500100
3500100
4500100

Example research 4

Insecticidal effect on larvae of the peach aphid (Myzus persicae):

Water is poured into the flask with screw-on lid (volume: 10 ml), and the petiole of Japanese horseradish placed there, and then infect 5-6 insects Myzus persicae on each petiole. After infection, the flask is placed in a glass cylinder (diameter: 3.5 cm; height: 15 cm, with lid from the grid), and insects provide an opportunity to multiply in a room with constant temperature at 25°within 3 days. Adults with leaves removed, and leaves dipped in diluted insecticide for agriculture and horticulture of the present invention, prepared in accordance with Example 3 (for about 5 seconds),and then return in a glass cylinder (two repeat at the chosen concentration). The cylinder is kept in a room with constant temperature at 25°and count the number of insects on the leaves on the 4th day after treatment, receiving mortality (%) on the basis of the obtained results. The results obtained are presented in table 5 (the number of connections in the table correspond to the numbers in table 1).

Table 5
Connection # Concentration (ppm)Mortality (%)
1500100
2500100
3500100
4500100

Example research 5

Insecticidal effect on larvae of brown rice cicadas (Nilaparvata lugens) through system activity:

The roots of young seedlings of rice (height: about 10 cm), germinated in a plastic vessel, washed with water, and wash away the soil so as not to damage the delicate roots. The stem is fixed in urethane tip (diameter: 3 cm, height: 2 cm), with the section line, and the roots are immersed in an Erlenmeyer flask, to which before that was placed 50 ml of a solution of the agent (insecticide for agriculture and horticulture of the present invention, razbam the military water prepared in accordance with Example composition 1) (2-3 young seedlings of rice/flask). Urethane tube split the shape of the throat of the flask to commit seedlings of rice. A glass tube (diameter: 3 cm height: 5 cm) placed in a urethane tube, fix and fix with tape. In this state, the flask is kept in a room with constant temperature at 25°within 3 days. Five larvae of Nilaparvata lugens placed in a glass tube, the tube urethane cover plate, followed by exposure in a room with constant temperature at 25°With (twice, at the chosen concentration). Investigate the death and the agony of larvae on day 4 after treatment, receiving mortality (%), given the moribund insects, such as1/2from a dead insect. This study was conducted on two solutions agent, differing in the concentration of the active ingredient. The results are presented in table 6 (the number of connections in the table correspond to the numbers in table 1).

In addition, as reference compounds similarly investigate the compounds I, II and III described in Japan patent JP-A-10-338676.

Table 6
With the Association No. Mortality (%)
of 3.1 ppm0,8 ppm
1100100
2100100
3100100
I100100
II5020
III00

Brown rice Cicada (Nilaparvata lugens) is a very problematic view of insect pests for agriculture and horticulture, but a sufficient effect cannot be obtained by applying the method of spraying agent on the stems and leaves, provided that pests find late or that does not apply to the roots sufficient amount of the agent.

Because this species has the characteristic of creating a region of its distribution around the roots of rice plants, or anything like that, and harm the plant by sucking the fluid, more efficient way of combating insects can be a way to handle the soil surface agent (processing granules) before the emergence of the wide distribution of insects. However, for high impact use of this method requires such a property agent as Prony is novenia and migration (system property) in plant tissues. As is obvious from table 6, all of the compounds of the present invention and the connection I have shown insecticidal activity in the form of a strong system properties in relation to this kind of very problematic insect pests. On the other hand, compounds II and III are obvious negative impact, due to their lower properties than the compounds of the present invention.

Example research 6

In vitro study of the inhibition of intercellular metabolic communication (IMC):

In this example, studies using inhibitory effect on intercellular communication through gap junction as an indicator, investigated the presence of Carcinogenicity (apokalyptische actions) connection.

In this study, the system of mixed cultures of lung fibroblasts Guinea pigs, line V79 (hgprt+)with hypoxanthineguanine phosphoribosyltransferase activity, and cells that do not have such activity (hgprt-), is treated by adding thereto the following compounds with 6-Tg (6-TG). When intercellular communication is normal, the toxic metabolite of 6-TG, which is formed in the cells hgprt+ (sensitive to 6-TG)is transferred into cells hgprt- (resistant to 6-TG) through the slotted contact, so that both cells die. On the other hand, when intercellular communication is giving inhibited using the compounds, only cells hgprt - survive and form colonies.

The study compound No. 2 of the present invention and comparative compound I, which shows high system activity in the above example, research 5, compound No. 2 of the present invention, as detected, is negative, but significant increase in the rate of formation of colonies observed at 7.5 and 15 μg/ml, in the case of compound I, and thus, the connection I discovered, is positive.

Accordingly, based on the research results, the compound of the present invention, as found, has a lower risk of carcinogenesis than compound I.

Example research 7

Insecticidal effect on cat flea:

On a round filter (diameter: 10 cm) are added dropwise 0.7 ml of a solution of the agent is diluted to a predetermined concentration. After drying, the filter is placed on the bottom of the cylinder (diameter: 10 cm × height: 30 cm). Ten fleas freely placed in it, and examined mortality on day 1 and day 2 after processing, calculating mortality (%) based on the results. The results are presented in table 7 (the number of connections in the table correspond to the numbers in table 1).

Table 7
No connectionTo icesto investigational agent (mg/filter) Mortality (%)
20,7100

The present invention is explained in detail with reference to specific embodiments, but for specialists in this field is obvious that various changes and modifications can be made without deviating from the spirit and scope of the present invention.

This application is based on patent application of Japan No. 2000-230238 registered on July 31, 2000, and its full content included in this application by reference.

Industrial applicability

Derivatives of 1-aryl-3-cyano-5-pyridylacetonitrile of the present invention are compounds suitable for use as new agents for combating pests, having a combination of characteristics of system activity and high safety in addition to excellent insecticidal activity and a broad spectrum insecticide exposure.

1. Derivative of 1-aryl-3-cyano-5-pyridylacetonitrile, represented by the following formula (I):

where X represents C-halogen; R1is halogenating group containing from 1 to 4 carbon atoms, except perhalogenated group; R2represents a hydrogen atom; R3represents the t of a hydrogen atom and R 4represents a hydrogen atom.

2. Agent for combating insects, containing a derivative of 1-aryl-3-cyano-5-pyridylacetonitrile according to claim 1 as an active ingredient.

3. The agent according to claim 2, representing the insecticide.

4. The agent according to claim 2, representing an insecticide for agriculture.

5. The agent according to claim 2, representing an insecticide for Pets.

6. The method of obtaining the derivative of 1-aryl-3-cyano-5-pyridylacetonitrile according to claim 1, which includes the interaction of a pyrazole derivative represented by the following formula (2), with R1SX1where R1has the same meaning as in the formula (1); and X1represents a chlorine atom or a bromine atom:

where X represents C-halogen; R2represents a hydrogen atom; R3represents a hydrogen atom and R4represents a hydrogen atom.

7. The method of obtaining the derivative of 1-aryl-3-cyano-5-pyridylacetonitrile according to claim 1, which includes processing halogenations agent pyrazole derivative represented by the formula (5)

where X represents C-halogen; R2represents a hydrogen atom; R3represents a hydrogen atom and R4represents the hydrogen atom in the presence of restore is his agent.



 

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; (2) group represented by the formula:

or ; (3) group represented by the formula:

; Xg represents -O-, -S-, C1-6-alkylene group or -N(Rg3)- (wherein Rg3 represents hydrogen atom); Yg represents optionally substituted C6-14-aryl group, optionally substituted 5-14-membered heterocyclic group including at least one heteroatom, such as nitrogen atom or sulfur atom, optionally substituted C1-8-alkyl group; Tg1 means (1) group represented by the following general formula:

; (2) group represented by the following general formula: . Other radical values are given in cl. 1 of the invention claim. Also, invention relates to a medicinal agent, pharmaceutical composition, angiogenesis inhibitor, method for treatment based on these compounds and to using these compounds. Invention provides preparing new compounds and medicinal agents based on thereof in aims for prophylaxis or treatment of diseases wherein inhibition of angiogenesis is effective.

EFFECT: improved treatment method, valuable medicinal properties of compounds and agents.

40 cl, 51 tbl, 741 ex

FIELD: organic chemistry, biochemistry.

SUBSTANCE: invention relates to compounds that inhibit binding ligands with α4β1-integrin (VLA-4) selectively. Compounds have the formula (I):

wherein W means unsubstituted phenyl or phenyl substituted with 1-3 substitutes taken among (C1-C6)-alkyl, halogen atom, (C1-C4)-alkoxy-group and halogen alkyl; W1 means unsubstituted phenylene or phenylene substituted with 1-3 substitutes taken among (C1-C6)-alkyl, halogen atom and (C1-C4)-alkoxy-group, pyridylene, pyridylene substituted with 1-3 substitutes taken among (C1-C6)-alkyl, halogen atom and (C1-C4)-alkoxy-group, 2-oxopyrrolylene or thiazolylene; A means oxygen atom (O); R means -(CH2)n- wherein n = 1 or 2; X means -C(O)-; M is taken among the following groups: a)

wherein means divalent 5- or 6-membered heterocyclic radical wherein nitrogen atom is located in the joining point to X wherein Q represents -CH2-, -O- or -S-; R1, R2 and R3 are taken independently among the group involving: hydrogen atom (-H), hydroxyl group (-OH), quinolinyloxy-group, -NH2, mono- or dialkylamino-group, (C1-C6)-alkylsulfonylamino-, arylsulfonylamino-, naphthyloxy-, phenyloxy-group substituted optionally with di-(C1-C6)-alkylamine, (C1-C6)-alkyl, benzyloxymethyl, halogen atom, phenyl, (C1-C4)-alkoxy-group; or two adjacent R1, R2 and R3 taken in common can form alkylene- or alkylenenedioxy-group substituted optionally with 1-3 alkyl groups; R4 means hydrogen atom (H), lower alkyl; Y is taken among a bond, (C2-C8)-alkenylene group, (C2-C8)-alkynylene group, -C(O)-, -C(O)NH- and -(CH2)kY2 wherein k is taken among 1, 2 and 3; Y2 means a direct bond or divalent radical taken among -O-, -S-, -S(O)-, -S(O)2- and -NY3- wherein Y3 is taken among hydrogen atom (H), lower alkyl; Z means (C3-C8)-cycloalkylene, optionally substituted phenylene, pyridylene, piperidylene, piperazinylene; A1 means a direct bond, -(CH2)t-alkynyl wherein t is taken among 1, 2 and 3; R5 means -OH, lower alkoxy-group, , ; b) means wherein R11 is taken among , -NR12- wherein R12 is taken among hydrogen atom (-H), optionally substituted lower alkyl, lower alkenyl, lower alkynyl, phenyl; Z3 is taken among a direct bond, (C1-C12)-alkyl wherein one or some carbon atoms can be replaced with -O- or -NR13- wherein R13 means hydrogen atom (-H), lower alkyl, wherein x = 0 or 1; y = 1, 2 or 3; R14 means hydrogen atom (-H), ; and when R11 means NR12 then Z3 is taken among: wherein 14Ra means hydrogen (H), halogen atom; , and ; Q2 means wherein R17 and R18 mean hydrogen atom (H), lower alkyl; or phenylene that can be substituted; L1 means -COOH or -COOR19 wherein R19 means lower alkyl. Compounds of the formula (I) inhibit activity of VLA-4-mediated adhesion of cells that allows their using in pharmaceutical compositions.

EFFECT: valuable medicinal properties of compounds and compositions.

21 cl, 11 tbl, 283 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel biologically active compounds. Invention describes compounds or their salts of the general formula (I): A-B-N(O)s (I) wherein s = 2; A means R-T1- wherein R represents radical of a medicinal substance under condition that a medicinal substance by the formula R-T1-Z or R-T1-OZ wherein Z represents hydrogen atom (H) or (C1-C5)-alkyl is taken among paracetamol, salbutamol, ambroxol, alendronic acid,, cetirizine, ampicillin, aciclovir, doxorubicin, simvastatin, diphylline, tacrine, clopidogrel, dimethylomeprazol, diclofenac, ferulic acid, enalapril, propranolol, benfurodil hemisuccinate, tolrestate or sulindac; T1 means (CO), oxygen atom (O) or NH; B means TB-X2-O- wherein TB means bivalent radical R1B-X-R2B wherein R1B and R2B are similar or different and represent linear or branched (C1-C6)-alkylenes and X represents a bond, oxygen (O), sulfur (S) atom or NR1C wherein NR1C represents hydrogen atom (H) or linear or branched (C1-C6)-alkyl; corresponding precursor B is represented by the formula -TB-X2-OH wherein TB means (CO) and free valence in TB represents -OZ wherein Z is determined above, or TB means oxygen atom (O), and free valence in TB represents hydrogen atom (H) under condition that in the formula (I) when X2 in precursor B represents linear or branched (C2-C20)-alkylene then a medicinal substance by the formula R-T1-Z or R-T1-OZ used in the formula (I) doesn't belong to the following substances: enalapril (ACE inhibitors) and diclofenac (NSAID). Also, invention describes pharmaceutical compositions for using in cases of oxidative stress and 4-nitroxybutanoic acid 4'-acetylaminophenyl ester. Invention provides preparing novel compounds possessing useful biological properties.

EFFECT: valuable medicinal properties of medicinal substances and compositions.

7 cl, 8 tbl, 32 ex

FIELD: organic chemistry, medicine, gastroenterology, pharmacy.

SUBSTANCE: invention relates to compounds represented by the formula (Ia) and compositions used in treatment of gastroenteric diseases based on thereof and their complexes being optionally in combination with compounds of the formula (Ib) . Also, invention describes pharmaceutical preparations and methods for their preparing these compounds. Invention provides preparing new compounds possessing useful biological properties.

EFFECT: valuable medicinal properties of compounds.

28 cl, 115 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: claim describes substituted anthranylamides of the general formula (I): wherein A means group =NR7; W means oxygen atom; D, E, F, G, X, Z, R1, R2, R7 and R9 have values given in the description and their isomers and salts also. Also, claim describes intermediate compounds used in preparing indicated anthranylamides. Also, invention relates to medicinal agents, their compositions and their using. Proposed compounds can be used in treatment of diseases associated with persistent angiogenesis that can be cause of different diseases, such as psoriasis, arthritis, for example, rheumatic arthritis, hemangioma, angiofibroma, ophthalmic diseases, for example, diabetic retinopathy, neovascular glaucoma, kidney diseases, for example, glomerulonephritis, diabetic nephropathy, malignant nephrosclerosis, thrombosis microangiopathy, rejection of transplants and glomerulopathy, fibrosis diseases, for example, hepatic cirrhosis, diseases associated with proliferation of mesangial cells and arteriosclerosis that can result to progression of these diseases. Invention provides the development of the corresponding medicinal agent designated for treatment of abovementioned diseases. The development of the preparation allows expanding assortment of agents used in treatment of such diseases.

EFFECT: valuable medicinal properties of compounds.

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: agriculture, in particular method for controlling of specific insect pests.

SUBSTANCE: invention relates to method for controlling of lepidopterous, homopterous, hemipterans, coleopterous, and physopods by contacting of said pests or environment thereof with effective amount of compound of formula I SSS1, N-oxide or agriculturally acceptable salt thereof being effective against abovementioned insects, wherein A and B are independently O or S; R1, R2 represent H, C1-C6-alkyl; R3 represents H, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or C3-C6-cycloalkyl; R4 represents H, C1-C6-alkyl, C2-C6-alkinyl, C1-C6-haloalkyl, CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, NO2;. R5 represents H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-hydroxyalkyl, CO2R11R12, halogen or C1-C4-alkoxy; R6 represents H, C1-C6-alkyl, C1-C6-haloalkyl; R7 represents H, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, phenyl ring, benzyl ring, or 5-6-membered heteroaromatic rind, naphthyl ring system, or 8-10-membered condensed heterodicyclic system. Also claimed are compound of formula I and benzoxazine derivative of formula 10 .

EFFECT: compounds effective against agriculture spineless depredators.

22 cl, 13 tbl, 1 dwg, 24 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

FIELD: organic chemistry, insecticides, chemical technology.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole of the general formula (1): wherein A means: (A-1) , (A-2) , (A-3) and (A-4) and wherein X represents C-halogen; R1 represents (C1-C4)-alkyl group or halogen-(C1-C4)-alkyl group; A represents any group among (A-1) - (A-4) wherein R4 represents hydrogen atom or (C1-C4)-alkyl group; n = 0, 1 or 2 under condition that R1 represents halogen-(C1-C4)-alkyl group with exception for perhalogenalkyl group when A represents (A-1) and n = 0, and that n doesn't equal 0 when A represents (A-4). Also, invention describes derivative of pyrazole of the formula (2): wherein A means: (A-1) and Y means: (Y-1) , (Y-2) and (Y-3) wherein X, R2, R3 and R4 have values given above; R5 represents hydrogen atom; A represents (A-1); Y means any group among (Y-1) - (Y-3); Z represents halogen atom that are intermediate compounds used for synthesis of the compound (1). Invention describes methods for preparing compounds of the formula (1) and (2) and insecticide comprising compound of the formula (1) as an active component. Insecticide shows high systemic activity, high safety and reduced harmful effect on environment in vicinity areas of its applying.

EFFECT: improved methods for preparing, valuable insecticide properties of compound.

11 cl, 9 tbl, 19 ex

FIELD: organic chemistry, agriculture, fungicide compositions.

SUBSTANCE: invention relates to compounds of formula I

, wherein R1 and R2 are hydrogen or C1-C4-alkyl; X is C3-C8-cycloalkyl, phenyl or styryl, as well as method for production thereof and fungicide composition containing the same. Compounds of present invention have fungicide activity and are useful in effective controlling of deleterious fungi.

EFFECT: compounds and fungicide composition with improved effectiveness.

3 cl, 2 tbl, 4 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

The invention relates to the field veterinariia and is intended for combating parasites in animals

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

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