Aminoacetonitrile compounds for control of endoparasites in warm-blooded productive cattle and in domestic animals

FIELD: organic chemistry, veterinary science.

SUBSTANCE: invention describes using aminoacetonitrile compounds of the formula (I): wherein Ar1 and Ar2 mean independently of one another unsubstituted phenyl or phenyl substituted with halide; Q means -C(R1)(R2) wherein R1 and R2 or independently of one another mean hydrogen atom, or in common with carbon atom to which they are bound form (C2-C6)-alkylene; d = 1; R3 means hydrogen atom, (C1-C6)-alkyl or (C2-C6)-alkynyl; each among R4, R5, R6, R7 and R8 means independently of one another hydrogen atom, (C1-C6)-alkyl or (C3-C6)-cycloalkyl; or R4 and R5 mean in common (C2-C6)-alkylene; W means oxygen atom; a and b mean independently of one another 0 or 1, and optionally of their enantiomers in control of endoparasitic pests in warm-blooded productive cattle and domestic animals. Also, the invention describes the composition and a method for control of endoparasitic pests. Above said compounds are used for control of endoparasites, especially, helminthes in warm-blooded productive cattle and in domestic animals.

EFFECT: valuable properties of compounds.

6 cl, 3 tbl, 5 ex

 

The present invention relates to the use of known aminoacetonitrile derivatives in combating endoparasites, especially helminths in warm-blooded productive livestock and domestic animals.

Attempts have been made to deal with worms, in which antiparasitary nematodes can cause serious diseases in mammals and poultry, by applying several small classes of active ingredients, for example, milbemycin. However, the active ingredients disclosed in the literature up to the present time, may not always meet the requirements regarding the efficacy and spectrum of activity. There is therefore a need in the active ingredients with improved pesticidal properties. It was found that derivatives of aminoacetonitrile described in the invention possess exceptional properties against endoparasites.

Derivatives aminoacetonitrile with pesticidal, especially insecticidal activity of plant protection are described, for example, in EP 0953565 A2. It was unexpectedly found that the following range of compounds of formula I also has an extremely good activity against endoparasites of warm-blooded animals and is extremely easy to carry pet-owner.

The compounds correspond to the General formula

where

Ar1 and Ar2mean independently from one another unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be selected independently of one another from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenyl, halogen(C2-C6)alkenyl, (C2-C6)quinil, (C3-C6)cycloalkyl, (C2-C6)-alkenylamine, halogen(C2-C6)alkenylamine, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonate, halogen(C1-C6)alkylsulfonate, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C2-C6)alkanity, halogen(C2-C6)alkanity, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C1-C6)alkylamino, di(C1-C6)alkylamino, (C1-C6)alkylsulfonyl, halogen(C1-C6) alkylsulfonyl, (C1-C6)alkylsulphonyl, halogen(C1-C6)alkylsulphonyl, (C1 -C6)alkoxycarbonyl, unsubstituted phenyl or phenyl which is substituted once or many times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl; the unsaturated phenoxy or phenoxy, which is substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl; unsubstituted phenylacetylene or phenylacetylene, substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-the 6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy. (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl; unsubstituted, pyridyloxy or pyridyloxy, which is substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl; unsubstituted pyridyl or pyridyl, which is substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenylamine, halogen(C2-C6)alkenylamine, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(the 1-C6)alkylsulfonyl, (C2-C6)alkanity, halogen(C2-C6)alkanity, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C1-C6)alkylamino and di(C1-C6)alkylamino; or

unsubstituted naphthyl or naphthyl, which is substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenylamine, halogen(C2-C6)alkenylamine, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C2-C6)alkanity, halogen(C2-C6)alkanity, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C1-C6)alkylsulfonyl and halogen(C1-C6)alkylsulfonyl, (C2-C6)alkanesulfonyl, halogen(C2-C6)alkanesulfonyl, (C1-C6)alkylamino and di(C1-C6)alkylamino;

<> Q means C(R1)(R2), CH=CH or C≡C;

R1and R2means independently of one another hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy or unsubstituted (C3-C6)cycloalkyl or (C3-C6)cycloalkyl, which is substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen and (C1-C6)alkyl; or means together with the carbon to which they relate, (C2-C6)alkylene, which is unsubstituted or substituted one or more times, whereby the substituents may be independent of one another and selected from the group comprising halogen, (C1-C6)alkyl and (C1-C6)alkoxy;

d is 0 or 1;

R3means hydrogen, (C1-C6)alkyl, halogen(C1-C6)alkyl, cyano(C1-C6)alkyl, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C2-C6)alkenyl or (C2-C6)quinil; R4, R5, R6, R7and R8denote each independently of one another hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C3-C6)cycloalkyl, which is either unsubstituted or substituted one who does several times, moreover, the substituents can be independent of one another and selected from the group comprising halogen and (C1-C6)alkyl; phenyl that is either unsubstituted or substituted once or many times, whereby the substituents may be independent of one another and selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6) alkoxy, halogen(C1-C6)alkoxy, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylsulfonyl, halogen(C1-C6)alkylsulfonyl, (C1-C6)alkylamino or di(C1-C6)alkylamino; or

R4and R5means together With2-C6)alkylen;

W stands for oxygen, sulfur, SO2or NR9;

R9means hydrogen or (C1-C6)alkyl; and a and b denote independently from one another 0, 1, 2, 3 or 4, and not necessarily their enantiomers, and W does not mean oxygen, if d is 0.

Alkyl as a group in itself and as structural element of other groups and compounds, such as haloalkyl, alkoxy, alkylthio, means in each case with due consideration of the specific number of carbon atoms in the group or in discussing the connection or line CE is the point, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl or branched chain, for example isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl.

Cycloalkyl as a group in itself and as structural element of other groups and compounds, such as kalodzishchy, cycloalkane, cycloalkene, in each case with due consideration of the specific number of carbon atoms in the group or in discussing the connection means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

Alkenyl as a group in itself and as structural element of other groups and compounds in each case with due consideration of the specific number of carbon atoms in the group or in discussing the connection means or linear chain, for example allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienyl or 1,3-octadiene or branched chain, for example Isopropenyl, Isobutanol, isoprenyl, tert.-pentenyl, isohexanol, isoheptane or isooctanol.

Quinil as a group in itself and as structural element of other groups and compounds in each case with due consideration of the specific number of carbon atoms in the group or in negotiated connection and conjugated or isolated double bonds means or linear chain, such as propargyl, 2-bout the Nile, 3-pentenyl, 1-hexenyl, 1-heptenyl, 3-HEXEN-1-inyl or 1.5-heptadien-3-inyl or branched chain, such as 3-methylbut-1-inyl, 4-ethylpent-1-inyl, 4-metrex-2-inyl or 2-methylhept-3-inyl.

Aryloxy means phenyloxy or 1-or 2-naphthyloxy.

Typically, the halogen means fluorine, chlorine, bromine or iodine. The same applies to halogen in combination with other values, such as haloalkyl or haloethanol.

Substituted by halogen carbon-containing groups and compounds can be gorodilova partially or completely, and in case of repeated haloiding halide substituents may be identical or different. Examples of haloalkyl as a group by itself and as structural element of other groups and compounds, such as haloalkoxy or haloalkylthio, are methylene, monosubstituted to trisemester fluorine, chlorine and/or bromine, such as CHF2or CF3; ethyl monosubstituted to pentamidine fluorine, chlorine and/or bromine, such as CH2CF3, CF2CF3, CF2CCl3, CF2CHCl2, CF2CHF2, CF2CFCl2, CF2CHBr2, CF2CHClF, CF2CHBrF or CClFCHClF; propyl or isopropyl, monosubstituted to heptathletes fluorine, chlorine and/or bromine, such as CH2CHBrCH2Br, CF2CHFCF3CH2CF2CF3or CH(CF3 2; and butyl or one of its isomers, monosubstituted to nonsliding fluorine, chlorine and/or bromine, such as CF(CF3)CHFCF3or CH2(CF2)2CF3; pencil or one of its isomers substituted 1-11 times by fluorine, chlorine and/or bromine, such as CF(CF3)(CHF)2CF3or CH2(CF2)3CF3; and hexyl or one of its isomers substituted by 1-13 times by fluorine, chlorine and/or bromine, such as (CH2)4CHBrCH2Br, CF2(CHF)4CF3CH2(CF2)4CF3or(CF3)2(CHF)2CF3.

Alkoxygroup preferably have a chain length from 1 to 6 carbon atoms. Alkoxy means, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, Deut.-butoxy and tert.-butoxy, as well as isomers pentyloxy, hexyloxy; preferably methoxy and ethoxy. Haloalkoxy preferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy means, for example, formatosi, deformedarse, triptoreline, 2,2,2-triptoreline, 1,1,2,2-tetrafluoroethoxy, 2-floratone, 2-chloroethoxy, 2,2-diflorasone and 2,2,2-trichloroethane; preferably deformedarse, triptoreline.

A preferred variant of the embodiment in the scope of the invention are as follows.

(1) Compound of formula I where Ar1and Ar2means independently of the Rog from each other phenyl, which is, or is not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group. comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenyl, halogen(C2-C6)alkenyl, (C2-C6)quinil, (C3-C6)cycloalkyl, (C2-C6)alkenylamine, halogen(C2-C6)alkenylamine, (C1-C6)alkylsulphonyl, halogen(C1-C6)alkylsulphonyl, (C1-C6)alkoxycarbonyl; phenyl that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; phenylacetylene that is either not substituted or substituted once or many times, whereby the substituents may be independent of each other and SEL is the selection of groups, comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; and pyridyloxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; or pyridyl, or is not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenylacyl or halogen(C2-C6)alkenylamine;

mainly independently of each other phenyl that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; and phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group, what with halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; or

pyridyl, or which is not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy;

in particular, independently of the other phenyl which is substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; and phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy.

(2) the Compound of formula I, where Q means C(R1)(R2) or CH=CH; especially C(R1)(R2).

(3) the Compound of formula I, where R1and R2mean independently from each other hydrogen, halogen, (C1-C6)alkyl, (C1-C6)alkoxy or (C 3-C6)cycloalkyl; or together with the carbon to which they relate, mean (C2-C6)alkylen;

in particular, independently from each other hydrogen or (C1-C6)alkyl; or together with the carbon to which they relate, (C2-C4)alkylen; especially hydrogen or together with the carbon to which they relate, (C2-C4)alkylen.

(4) the Compound of formula I, where d means 1.

(5) the Compound of formula I, where R3means hydrogen, (C1-C6)alkyl or halogen(C1-C6)alkyl, especially hydrogen, and (C1-C6)alkyl; most specifically hydrogen.

(6) the Compound of formula I, where R4, R5, R6, R7and R8mean independently from each other hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C3-C6)cycloalkyl; phenyl that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; mostly independently from each other hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl or (C3-C6)cycloalkyl; in particular, independently from each other hydrogen, halogen, (C -C6)alkyl, halogen(C1-C6)alkyl.

(7) the Compound of formula I, where W stands for oxygen, sulfur or N(R9); especially oxygen or N(R9); in particular, oxygen.

(8) the Compound of formula I, where R9means hydrogen or (C1-C4)alkyl, especially hydrogen or (C1-C2)alkyl, in particular methyl.

(9) the Compound of formula I, where a and b denote independently from each other 0, 1, 2 or 4; mainly, independently from each other 0, 1 or 4; in particular, independently of each other 0 or 1.

(10) the Compound of formula I where Ar1and Ar2means independently of the other phenyl which is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenyl, halogen(C2-C6)alkenyl, (C2-C6)quinil, (C3-C6)cycloalkyl, (C2-C6)alkenylamine, halogen(C2-C6)alkenylamine, (C1-C6)alkylsulphonyl, halogen(C1-C6)alkylsulphonyl, (C1-C6)alkoxycarbonyl; phenyl that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and selected from the C group, comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy; phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy; phenylacetylene that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy; and pyridyloxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy; or pyridyl, or is not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy, (C2-C6)alkenylacyl and halogen(C2-C6)alkenylamine;

Q means C(R1)(R2) or CH=CH;

R1and R2mean independently from each other hydrogen, halogen, (C1-C6)alkyl, (C1-C6)alkoxy or (C3-C6)cycloalkyl; or together with the carbon to which they are attached, mean (2-C6)alkylen;

d means 1;

R3means hydrogen, (C1-C6)alkyl or halogen(C1-C6)alkyl;

R4, R5, R6, R7and R8mean independently from each other hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C3-C6)cycloalkyl; phenyl that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy;

W stands for oxygen, sulfur or N(R9);

R9means hydrogen or (C1-C4)alkyl; and

(11) the Compound of formula I where Ar1and Ar2means independently of the other phenyl which is either not substituted or substituted once or many times, whereby the substituents may be independent of each other and the choice is are stated from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; and phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy; or pyridyl, or is not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy;

Q means C(R1)(R2);

R1and R2mean independently from each other hydrogen or (C1-C6)alkyl; or together with the carbon to which they relate, mean (C2-C4)alkylen;

d means 1;

R3means hydrogen or (C1-C4)alkyl;

R4, R5, R6, R7and R8mean independently from each other hydrogen, halogen, (C1-C6)alkyl, halogen(C1-C6)alkyl or (C3-C6)cycloalkyl;

W stands for oxygen or N(R9);

R9means hydrogen or (C1 -C2)alkyl; and a and b denote independently from each other 0, 1 or 4, and

(12) the Compound of formula I where Ar1and Ar2means independently of the other phenyl which is substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy, halogen(C1-C6)alkoxy; and phenoxy that is either not substituted or substituted once or many times, whereby the substituents may be independent from each other and are selected from the group comprising halogen, nitro, cyano, (C1-C6)alkyl, halogen(C1-C6)alkyl, (C1-C6)alkoxy and halogen(C1-C6)alkoxy;

Q means C(R1)(R2);

R1and R2mean hydrogen or (C1-C6)alkyl; or together with the carbon to which they relate, mean (C2-C4)alkylen;

d means 1;

R3means hydrogen;

R4, R5, R6, R7and R8mean independently from each other hydrogen, halogen, (C1-C6)alkyl or halogen(C1-C6)alkyl;

W stands for oxygen;

R9means methyl; and

a and b denote independently from each other 0 or 1.

The compounds I can exist in the form of one of the possible isomers or in the when asked their mixtures, for example, depending on the number, absolute and relative configuration of asymmetric carbon atoms in the form of pure isomers, such as antipodes and/or diastereoisomers, or as mixtures of isomers, such as mixtures of enantiomers, such as racemates, diastereoisomeric mixtures or racemic mixtures; the invention relates both to the pure isomers and to all possible isomeric mixtures, and should be understood as such above continue, even if stereochemical details are not specifically mentioned in each case. The synthesis of compounds described, for example, in EP 0953565 A2.

Compounds of formula I mentioned in the following table 1, are representative examples. Further examples are mentioned in the tables EP 0953565 A2.

Table 1

The compounds I according to the invention is distinguished by their broad spectrum of activity and are valuable active ingredients in the field of pest control in animals, in particular, including combating endoparasites, especially helminths, and at the same time very portable warm-blooded animals, fish and plants. Pests include endoparasites nematodes that can cause serious diseases in mammals and poultry, for example, sheep, pigs, goats, cattle the cat horses, donkeys, dogs, cats, Guinea pigs and exotic birds. Typical nematodes in this reading are: At, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. The particular advantage of the compounds of the formula I is their effectiveness against those parasites that are resistant to the action of active ingredients on the basis of benzimidazole. Some pest species of Nematodirus, Cooperia and Oesophagostonum infect the intestinal tract of an animal host, while other species At and Ostertagia parasites in the stomach, and the pest species of Dictyocaulus Lodge in the lung tissue. Parasites of the families Filariidae and Setariidae can be detected in the intracellular basis and in organs such as the heart, blood vessels, lymph vessels, and subcutaneous basis. Especially noticeable parasite is a heart worms in dogs, Dirofilaria immitis. The compounds of formula I are highly effective against these parasites.

In addition, the compounds of formula I useful for combating pathogenic parasites of man. From these typical representatives that appear in the digestive tract, are parasites of the species Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Trichuris and Enterobius. Compounds of the present invention are also effective against species Wuchereria, Brugia, Onchocerca and Loa from families who tion Filariidae, which appear in the blood, in tissue and in various organs, as well as against Dracunculus and parasites of the species Strongyloides and Trichinella, which population, in particular the gastrointestinal tract.

The good pesticidal activity of the compounds of formula I corresponds to the percentage of mortality of at least 50-60% of the mentioned parasites. The compounds of formula I are especially notable for the exceptional duration of effective action.

The compounds of formula I are preferably used in unmodified form or preferably together with auxiliary substances commonly used in the field of composition, and therefore they can be processed in a known manner to give, for example, emulsifiable concentrates, directly dilutable solutions, dilute emulsions, soluble powders, granules or microcapsules of polymeric substances. As for the compositions, the methods of application are chosen in accordance with the intended objectives and the prevailing circumstances.

Dosage form, i.e. the agents, preparations or compositions containing the active ingredient of the formula I, or combinations of these active ingredients with other active ingredients and optionally a solid or liquid auxiliary substance, produced by a method which is known in itself, for example, by carefully what additional mixing and/or dispersion of the active ingredients with the spreading of the compositions, for example with solvents, solid carriers and optionally with surface-active compounds (surfactants).

Discussing the solvent may include: alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, simple dipropyleneglycol ether, ethylene glycol, simple onomatology or monotropy ether of ethylene glycol, ketones, such as cyclohexanone, isophorone or diacetolol alcohol, cinnaprarie solvents, such as N-methyl-2-pyrrolidone, dimetilan oxide, dimethylformamide or water, vegetable oils, such as rapeseed, castor, coconut or soya oil, and, if appropriate, silicone oils.

A preferred form of application for use on warm-blooded animals in combating helminths include solutions, emulsions, suspensions (fluids in the oral cavity), food additives, powders, tablets including effervescent tablets, boluses, capsules, microcapsules and wetting form, and must take into account the compatibility of excipients pharmaceutical form.

Binders for tablets and boluses can be chemically modified natural polymer substances, which are soluble in water or alcohol, such as starch derivatives, cellulose or protein (e.g., methylcellulose, carbox is methylcellulose, metilgidroxiatilzelllozu, proteins such as Zein, gelatin and the like), as well as synthetic polymers such as polyvinyl alcohol, polyvinylpyrrolidone, etc. Tablets also contain fillers (e.g. starch, microcrystalline cellulose, sugar, lactose, etc.), sliding substances and disintegrators.

If anthelminthic substances are present in the form of food concentrates, used by the media are, for example, productive forage, feed grains and protein concentrates. Such food concentrates or compositions, not to mention the active ingredients may also contain additional substances, vitamins, antibiotics, chemotherapeutic agents or other pesticides, primarily bacteriostatic, fungistatic, coccidiostatic or even hormone preparations, substances having anabolic effect, or substances that promote growth, which affect the quality of the meat of slaughtered animals, or which are useful for the body otherwise. If the composition or contained active ingredients of the formula I is administered directly into feeders or waterers, then developed food or drink contains active ingredients preferably in a concentration of approximately of 0.0005 to 0.02% of the mass (5-200 ppm).

The compounds of formula Po invention can be applied individually or in combination with other biocides. They can be combined with pesticides, with activity in the same area, for example, to increase the activity, or with substances having activity in another area, in order to expand the range of activity. It may also make sense to add so-called repellents.

If the range of activity should be extended to the endoparasites, such as helminths, the compounds of formula I, respectively, combined with substances having antiendomysium properties. Of course, they can also be used in combination with antibacterial compositions. Since the compounds of formula I are adulticide, i.e. because they are effective against the intended parasites especially at the stage of adult individuals, the addition of pesticides, which instead are at the stage of young individuals, can be very useful. This method will cover the greatest part of those parasites that cause enormous economic damage. Moreover, this action will greatly help to avoid the formation of sustainability. Many combinations can also lead to synergistic effects, i.e. the total amount of the active ingredient can be reduced, which is desirable from an environmental point of view. A preferred group of agents combinations and particularly preferred agents to the combination cited below moreover, the combination may include one or more of these agents in addition to the compound of formula I.

The relevant agents of the mixture can be biocides such as insecticides and acaricides with changing mechanism activity, which are named below and well-known specialist in this field for a long period of time, such as chitin synthesis inhibitors, growth regulators; active ingredients which act as juvenile hormones; active ingredients which act as connection, effective at the stage of adult broadband insecticides, broadband acaricides and nematicides; and is also well known for anthelminthic substances and substances that slow the growth of insects and/or mites, the aforementioned repellents or detacher.

Not limiting the invention, examples of appropriate insecticides and acaricides are:

46. Cyhexatin
1. The abamectin32. Carbophenothion65. Ethiofencarb
2. AC 303 63033. Cartap66. Ation
3. Arafat34. Cloethocarb67. Etofenprox
4. Acrinathrin35. Chlorine is amoksibos 68. Ethoprophos
5. AlankarÇ6. Chlorfenapyr69. Etrimfos
6. Aldicarb37. Chlorfluazuron70. Fenamiphos
7. α-Cypermethrin38. Chlormephos71. Fenazaquin
8. Alphamethrin39. The chlorpyrifos72. Fenbutatin
9. Amitraz40. CIS-Resmethrin73. Penetration
10. Avermectin141. Glazirin74. Fenobucarb
11. AZ 6054142. Clofentezine75. Fanatical
12. Azinphos And43. Cyanophos76. Fenoxycarb
13. Azinphos M44. Cicloprofen77. Fenpropathrin
14. Azinphos-methyl45. Cyfluthrin78. Feneral
15. Azocyclotin79. Fenpyroximate
16. The toxin of Bacillus subtil.47. D 234180. Fenthion
17. Bendiocarb48. Deltamethrin81. Fenvalerate
18. Benfuracarb49. Demeton M82. Fipronil
50. Demeton S83. Fluazinam
19. Bensultap51. Demeton-S-methyl84. Fluazuron
20. β-Cyfluthrin52. Dibutylamino85. Flucycloxuron
21. Bifenthrin53. Dichlofenthion86. Flucythrinate
22. VRMS54. Declivous87. Flufenoksuron
23. Papenbrock55. Diation88. Plutopress
24. Bromophos And56. Diflubenzuron89. Fonofos
25. Bofenkamp7. Timeout90. Formation
26. Buprofezin58. Dimethylene91. Fosthiazate
27. Butocarboxim59. Dioxathion92. Tupfenrock
28. Butylparaben60. DPX-MP06293. NSN
29. Cadusafos61. Edifenphos94. Heptenophos
30. Carbaryl62. Emamectin95. Hexaflumuron
31. The carbofuran63. Endosulfan96. Hexythiazox
64. Esfenvalerate97. The hydroprene

98. Imidacloprid127. Oxydemeton M160. Tebufenozide
99. Mushrooms-insecticides128. Oxidation161. Tebufenpyrad
129. Parathion162. Tebupirimfos
100. Nematodes-insecticides130. Parathion-methyl163. Teflubenzuron
131. Permethrin164. Tefluthrin
101. Viruses insecticides132. Pintout165. Temephos
133. Port166. Terram
102. Iprobenfos134. Fosalan167. Terbufos
103. Isofenphos135. Phosmet168. Tetrachlorvinphos
104. Isoprocarb136. Phoxim169. Titanox
105. Isoxathion137. Pirimicarb170. Thiodicarb
106. Ivermectin138. Pirimiphos And171. Thiofanox
107. λ-Cigalotrin139. Pirimiphos M172. Thionazin
108. Lufenuron140. Promecarb173. Thuringiensis
109. Malathion141. Propafol174. Tralomethrin
110. Mecarbam142. Propoxur175. Threaten
111. Resultados143. Prothiofos176. Triazamate
112. Metaldehyde144. Procoat177. Triazophos
113. Methamidophos145. Pyraclofos178. Treasure
114. Methiocarb146. Predatation179. Trichlorfon
115. Methomyl147. Prismatron180. Triflumuron
116. Methoprene148. Feverfew181. Timetaken
117. Metolcarb149. Pyridaben182. Validation
118. Mevinphos150. Pyrimidifen183. CMS (3,5-Xylylenediisocyanate)
119. Milbemectin151. Pyriproxifen /td>
120. Moxidectin152. RH5992
121. Naled153. RH-2485184. Xiller
122. NC 184154. Coalition185. YI 5301/5302
123. NI-25, Acetamiprid155. Sabots186. ζ-Cypermethrin
156. Selflove187. Decamethrin
124. Nitenpyram157. Spinosad
125. Omethoate158. Sulfotep
126. Oxamyl159. Alphaprofit

Not limiting the invention, examples of relevant anthelminthic substances are given below, some typical representatives, in addition to the anthelminthic activity, have activity against insects and mites and partially already listed above.

(A1) Praziquantel = 2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline

(A2) Closantel = 3,5-did-N-[5-chloro-2-methyl-4-(α-Sapo-4-Chlorobenzyl)phenyl]salicylamide

(A3) the Trick is abendazole = 5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole

(A4) Levamisole = L-(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole

(A5) Mebendazole = methyl ester (5-benzoyl-1H-benzimidazole-2-yl)carbamino acid

(A6) Omphalotin = macrocyclic product of fermentation mushroom Omphalotus olearius, described in WO 97/20857

(A7) Abamectin = avermectin B1

(A8) Invermectin = 22,23-dihydroavermectin B1

(A9) Moxidectin = 5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)milbemycin

(A10) Doramectin = 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl " avermectin A1A

(A11) Milbemectin = mixture milbemycin A3 and milbemycin A4

(A12) Milbemycin = 5-oxime milbemectin

Not limiting the invention, examples of appropriate repellents and Betaseron are:

(R1) REET (N,N-diethyl-m-toluamide)

(R2) KBR 3023 (N-butyl-2-oxycarbonyl-(2-hydroxy)piperidine)

(R3) Zemiata (N-2,3-dihydro-3-methyl-1,3-thiazol-2-ilidene-2,4-xylidene

The above-mentioned agents in the mixture is well known to specialists in this field. Most are described in various publications Pesticide Manual, The British Crop Protection Council, London, and others in various editions of The Merck Index, Merck and Co., Inc., Rahway, New Jersey, USA or in the patent literature.

Therefore, the following listing is limited to a few sources where you can find them in the form of an example.

(I) 2-Methyl-2-(methylthio)Propionaldehyde-O-methylcarbamate (Aldicarb), from The Pesticide Manual, 11ththe ZV. (1997), The British Crop Protection Council, London, p.26;

(II) S-(3,4-dihydro-4-oksobenzo[d][1,2,3]triazine-3-ylmethyl)-O,O-dimethyl-phosphorodithioate (Azinphos-methyl), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.67;

(III) ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-jocstarbunny-(methyl)aminothio]-N-isopropyl-β-alaninate (Benfuracarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.96;

(IV) 2-methylbiphenyl-3-ylmethyl-(Z)-(1RS)-CIS-3-(2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (Bifenthrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, page 118;

(V) 2-tert.-Butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one (Buprofezin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.157;

(VI) 2,3-dihydro-2,2-dimethylbenzofuran-7-illecillewaet (Carbofuran), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London,str;

(VII) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl(dibutylamino)methylcarbamate (Carbosulfan), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(VIII) S,S'-(2-dimethylaminomethylene)-bis(THIOCARBAMATE) (Cartap), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(IX) 1-[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-differentail)urea (Chlorfluazuron), from The Pesticide Manual, 11th ed. (1997), The British Crop Protection Council, London, str;

(X) o,O-diethyl-O-3,5,6-trichloro-2-redifferentiate (chlorpyrifos), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London,str;

(XI) (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS, 3RS;1RS, 3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Cyfluthrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XII) Mixture of (S)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2-chloro-3,3,3-tryptophanyl)-2,2-dimethylcyclopropanecarboxylate and (R)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2-chloro-3,3,3-tryptophanyl)-2,2-dimethylcyclopropanecarboxylate (lambda Cigalotrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XIII) the racemate comprising (S)-α-cyano-3-phenoxybenzyl-(2)-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (R)-α-cyano-3-phenoxybenzyl-(15,35)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (alpha-Cypermethrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl-(1RS, 3RS, 1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Zeta-Cypermethrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London,str;

(XV) (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate (Deltamethrin), from The Pesticide Manual, 11th ed. (1997), The British Crop Protection Council, London, str;

(XVI) (4-chlorophenyl)-3-(2,6-differentail)urea (Diflubenzuron), from The Pesticide Manual, 11th. (1997), The British Crop Protection Council, Lonon, str;

(XVII) (1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-rebismart)-sulfite (Endosulfan), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XVIII) α-ethylthio-o-trimethylarsine (ethiofencarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XIX) o,O-dimethyl-O-4-nitro-m-califoruia (Fenitrothion), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XX) 2-sec.-butylphenylmethyl (Fenobucarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXI) (RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate (Fenvalerate), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXII) S-[formyl(methyl)carbamoylmethyl]-Oh,Oh-dimethylphosphorodithioate (Formation), from The Pesticide Manual, 11thed. (1997), The British Crop. Protection Council, London, str;

(XXIII) 4-methylthio-3,5-xylylenediisocyanate (Methiocarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXIV) 7-chlorobicyclo[3.2.0]hepta-2,6-Dien-6-endimetriosis (Heptenophos), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamino (Imidacloprid), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXVI) 2-isopropylaminocarbonyl (Isoprocarb), from The Pesticide Manual, 11thed. (1997), The British Crop Prtection Council, London, str;

(XXVII) O,S-dimethylphosphorodithioate (Methamidophos), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXVIII) of S-methyl-N-(methylcarbamoyl)thioacetimidate (Methomyl), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXIX) methyl-3-(diethoxyphosphoryloxy)but-2-ENOAT (Mevinphos), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXX) o,O-diethyl-O-4-nitrophenylphosphate (Parathion), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXXI) o,O-dimethyl-O-4-nitrophenylphosphate (Parathion-methyl), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London,str;

(XXXII) S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-o,O-diethyl-phosphorodithioate (Vocalon), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXXIII) 2-dimethylamino-5,6-dimethylpyrimidin-4-ultimatecarpage (Pirimicarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXXIV) 2-isopropoxybenzonitrile (Propoxur), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXXV) 1-(3,5-dichloro-2,4-differenl)-3-(2,6-differentail)urea (Teflubenzuron), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XXXVI) S-tert.-butylthioethyl-0,0-dimethylphosphorodithioate(Terbufos), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Coucil, London,str;

(XXXVII) ethyl-(3-tert.-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazole-5-ylthio)-acetate (Triazamate), from The Pesticide Manual, 11^ ed. (1997), The British Crop Protection Council, London, str;

(XXXVIII) Abamectin, from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, page 3;

(XXXIX) 2-sec.-butylphenylmethyl (Fenobucarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XL) N-tert.-butyl-N'-(4-ethylbenzoyl)for 3,5-dimethylbenzophenone (Tebufenozide), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLI) (±)-5-amino-1-(2,6-dichloro-(α,α,α-Cryptor-n-tolyl)-4-triftormetilfullerenov-3-carbonitrile (Fipronil), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLII) (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS;1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (beta-cyfluthrin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLIII) (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane (Selfloader), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLIV) of tert.-butyl(E)-α-(1,3-dimethyl-5-Phenoxyethanol-4-ylmethylamino-hydroxy)-n-toluate (Fenpyroximate), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLV) 2-tert.-butyl-5-(4-tert.-butylbenzyl)-4-chloropyridin-3(2P)-he (Pyridaben), from The Pesticide Manual, 11thed. (1997), The British Crop rotection Council, London, str;

(XLVI) 4-[[4-(1,1-dimetilfenil)phenyl]ethoxy]hinzelin (Fenazaquin), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London,str.507;

(XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl ether (Pyriproxifen), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLVIII) 5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4-amine (Pyrimidifen), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(XLIX) (E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitropyridinium (Nitenpyram), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(L) (E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamide (NI-25, Acetamiprid), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, page 9;

(LI) Avermectin B1from The Pesticide Manual, 11thed. (1997). The British Crop Protection Council, London, page 3;

(LII) insect-active extract from a plant, particularly (2R,6aS,12aS)-1,2,6,6A,12,12A-hexahydro-2-Isopropenyl-8,9-dimethoxypropane[3,4-b]furo[2,3-b]chromen-6-he (Rotenone), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, CTR; and an extract from Azadirachta indica, especially azadirachtin, from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.59; and

(LIII) a drug which contains insect-active nematodes, preferably Heterorhabditis bacteriophora and Heterorhabditis megidis from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str; Steinernema feltiae from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str and Steinernema scapterisd from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(LIV) preparation derived from Bacillus subtilis, from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.72; or from a strain of Bacillus thuringiensis, with the exception of the compounds selected from GC91 or NCTC11821; The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.73;

(LV) product that contains insect-active mushrooms, preferably Verticillium lecanii from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str; Beauveria brogniartii from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.85 and Beauveria bassiana from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, p.83;

(LVI) a drug which contains insect-active viruses, preferably NPV Neodipridon Sertifer from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str; NPV Mamestra brassicae from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str and the virus of Cydia pomonella granulosis from The Pesticide Manual, 11th ed. (1997), The British Crop Protection Council, London, str.291;

(CLXXXI) 7-chloro-2,3,4A,5-tetrahydro-2-[methoxycarbonyl-(4-trifloromethyl)carbarnoyl]indole[1,2-e]oxazoline-4-carboxylate (DPX-MP062, Indoxacarb), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, str;

(CLXXXII) N'-tert.-butyl-N'-(3,5-dimethylbenzoyl)-3-is ethoxy-2-methylbenzhydryl (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11thed. (1997), The British Crop Protection Council, London, CTR; and

(CLXXXIII) isopropyl ester N′-[4-methoxybiphenyl-3-yl]hydrazinecarboxamide acid (D 2341), Brighton Crop Protection Conference, 1996, 487-493;

(R2) Abstracts 212thNational Congress of American chemical society, Orlando, FL, August 25-29 (1996), AGRO-020. Ed.: American chemical society, Washington, D.C.CONEN: 63 BFAF.

As a consequence of the above information further aspect of the present invention relates to compound drugs for combating parasites of warm-blooded animals, characterized in that, in addition to the compounds of formula I, they contain at least one additional active ingredient having the same or a different type of activity and at least one physiologically acceptable carrier. The present invention is not limited to dual combinations.

As a rule, anthelmintic compositions according to the invention contain 0.1 to 99 wt.%, especially 0.1 to 95 wt.% the active ingredient of the formula I, la or mixtures thereof, 99,9-1 wt.%, especially 99,8-5 wt.% solid or liquid mixture, including 0-25 wt.%, especially 0.1 to 25 wt.% surface-active substances.

The introduction of the compositions according to the invention is an animal that must be processed, can occur locally, orally, parenterally or subcutaneously, and the song finds the I in the form of solutions, emulsions, suspensions (injections), powders, tablets, boluses, capsules and wetting dosage forms.

The method of wetting or stain formation consists of applying the compounds of formula I on a particular area of skin or hair coat, mainly on the neck or spine of the animal. This is implemented by, for example, using a swab or spray wetting or forming a spot of the dosage form in a relatively small area of the coat, where the active substance is distributed in fact involuntarily over large surfaces wool due to the spreading nature of the components in the dosage form and facilitate animal movements.

Accordingly wetting and forming a spot dosage forms contain media that contribute to the rapid spread over the surface of the skin and wool cover an animal host and, generally regarded as the flowing oil. Appropriate carriers are, for example, oil solutions; alcohol and isopropanol solutions, such as solutions of 2-octyldodecanol or olejowego alcohol; solutions in esters of monocarboxylic acids, such as isopropylmyristate, isopropyl, ester of lauric alcohol and oxalic acid, ester olejowego alcohol and oleic acid, complex EF the R delovogo alcohol and oleic acid, exellent, decillia, esters of capric acid and saturated fatty alcohols with a chain length of C12-C18; solutions of esters of dicarboxylic acids, such as dibutyl phthalate, diisopropylnaphthalene, complex diisopropyl ether, adipic acid, di-n-butylacetat or also solutions of esters of aliphatic acids, for example, glycols. Can take advantage of the additional presence of a dispersing agent, such as a dispersing agent, known in the pharmaceutical or cosmetic industry. Examples are 2-pyrrolidone, 2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and its simple or complex esters, propylene glycol or synthetic triglycerides.

Oil solutions include, for example, vegetable oils such as olive oil, oil of groundnuts, sesame oil, pine oil, linseed oil or castor oil. Vegetable oil can also be present in epoxydecane form. Can also be used paraffins and silicone oils.

Wetting or forming a spot dosage form typically contains 1-20 wt.% the compounds of formula I, 0.1 to 50 wt.% dispersing agent and 45-98,9 wt.% the solvent.

The method of wetting or stain formation is particularly advantageous for use in herd animals such as cattle, horse the, sheep or pigs, in which it is difficult or takes a long time processing of all animals orally or by injection. Due to its simplicity, this method can certainly be used for all other animals, including domestic animals or Pets, and has earned great location, pet owners, as it can often be implemented without the presence of a specialist vet.

Although commercial products are preferably designed as concentrates, the end user will normally employ dilute composition.

To achieve special effects such compositions may also contain additional additives, such as stabilizers, preventing foaming agents, viscosity regulators, binders or substance to improve the adhesiveness, as well as other active ingredients.

Anthelmintic compositions of this type, which are used by the end user, also form part of the present invention.

In each of the methods according to the invention for pest control or in each of the compositions for pest control according to the invention the active ingredients of the formula I can be used in all of their spatial configurations, or their mixtures.

The invention also includes a method of prevention for the of ITA's warm-blooded animals, especially productive livestock, domestic animals and Pets, against parasitic helminths, which differs in that the active ingredients of the formula I or compositions of active ingredients derived from them, is administered to animals as feed or drinking supplements or also in solid or liquid form, orally, by injection or parenteral. The invention also includes compounds of formula I according to the invention for use in one of the mentioned methods.

The following examples merely serve to illustrate the invention, without limitation, the term "active ingredient" means a substance listed in tables 1-3.

In particular, the preferred compositions are made as follows: (% means mass%)

Examples of songs
1. The granulate(a)(b)
The active ingredient from table 15%10%
Kaolin94%-
Finely dispersed silicic acid1%-
Attapulgite-90%

The active ingredient is dissolved in methylene chloride, dispersed in the carrier, and the solvent is then concentrated by which paravane in vacuum. The granules of this type can be mixed with food animals.

2. The granulate

The active ingredient from table 13%
Polyethylene glycol (mol. weight 200)3%
Kaolin94%

(mol. the weight mean molecular weight)

The finely ground active ingredient is uniformly applied, in a mixer on kaolin, which has been moistened with polyethylene glycol. This way get free from powder granules coated.

3. Tablets or boluses

I. the Active ingredient from table 133,0%
The methylcellulose0,80%
Silicic acid fine0,80%
Corn starch8,40%
II. Lactose crystal22,5%
Corn starch17,00%
Microcrystalline cellulose16,5%
Magnesium stearate1,00%

I. Methylcellulose vmeshivat in the water. After swelling substances vmeshivat silicic acid and the mixture is suspended until smooth. The active ingredient and the corn starch are mixed. Aqueous suspension of whom are in this mixture and knead until the paste-like state. The resulting mass granularit through a sieve 12 M and dried.

II. All four of the filler are thoroughly mixed.

III. Pre-mixture obtained in accordance with sections I and II are mixed and pressed into tablets or boluses.

4. Means for injection

A. Oil filler (slow release)

1. The active ingredient from table 10.1 to 1.0 g
Oil of groundnutsTo 100 ml
2. The active ingredient from table 10.1 to 1.0 g
Sesame oilTo 100 ml

Receiving: the active ingredient is dissolved in part of the oil with stirring and, if necessary, at low heat, then after cooling is brought to the desired volume and spend sterile filtering through a suitable membrane filter with a pore size 0,22 mm

B. Mixed with water, the solvent (the average rate of release)

The active ingredient from table 10.1 to 1.0 g
4-Hydroxymethyl-1,3-dioxolane40 g
(clearinterval)
1,2-PropandiolTo 100 ml
The active ingredient from table 1 0.1 to 1.0 g
Dimethylacetal glycerin40 g
1,2-PropandiolTo 100 ml

Receiving: the active ingredient is dissolved in part of the solvent with stirring, cook until the desired volume and filtered under sterile conditions through a suitable membrane filter with a pore size 0,22 mm

C. an Aqueous solution (quick release)

1. The active ingredient from table 10.1 to 1.0 g
Polyethoxysiloxane castor oil (4010 g
ethyleneoxide units)
1,2-Propandiol20 g
Benzyl alcohol : 1 g
Water for injectionTo 100 ml
2. The active ingredient from table 10.1 to 1.0 g
Polyethoxysiloxane monooleate8 g
sorbitan (20 ethyleneoxide units)
4-Hydroxymethyl-1.3-dioxolane20 g
(clearinterval)
Benzyl alcohol : 1 g
Water for injectionTo 100 ml

Receiving: the active ingredient is dissolved in the solvents, the surface-active substance and bring water to the desired volume. Spend sterile filtering through a suitable membrane filter with a pore size 0,22 mm

5. Wetting

A. the Active ingredient from table 15 g
Isopropylmyristate10 g
IsopropanolTo 100 ml
B. Active ingredient from table 12 g
Exellent5 g
Triglycerides medium chain length15 g
EthanolTo 100 ml
C. the Active ingredient from table 12 g
Aerolef5 g
N-Organic40 g
IsopropanolTo 100 ml

The water system can also preferably be used for oral and/or intraruminal introduction.

The composition may also contain additional additives, such as stabilizers, for example, in case of appropriate epoxydecane vegetable oils (epoxidizing coconut oil, rapeseed oil or soybean oil); substances that prevent foaming, for example silicone oil, preservatives, viscosity regulators, binders, substances for improving adhesiveness, and t is the train pollinators or other active ingredients for achieving specific effects.

Additional biologically active substances or additives which are neutral with respect to compounds of formula I and have no harmful effects on an animal host that is to be processed, as well as mineral salts or vitamins may also be added to the desired compositions.

Biological examples

In vivo test on Trichostrongylus colubriformis and At contortus clawed at the Mongolian gerbil (Meriones unguiculatus) using oral administration

Clawed Mongolian gerbils aged 6-8 weeks were infected by artificial feeding with approximately 2000 larvae in the third age stage each of .colubriformis and .contortus. 6 days after infection, the animals were given a light General anesthesia with N2O and was treated with oral investigational compounds, dissolved in a mixture of 2 parts DMSO and 1 part of polyethylene glycol (PEG 300), in quantities of 100, 32 and 10-0,1 mg/kg On the ninth day (3 days after treatment), when most are still present .contortus was on the fourth age stage larvae and most .colubriformis was immature adults, gerbils were scored for counting the number of worms. Efficiency was calculated as the percentage reduction in the number of worms in each gerbils compared with the geometric mean number of worms in eight infected and untreated gerbils.

Below is a detailed description of the conducted research.

2 μl of a 5%solution of the test compound in dimethyl sulfoxide or methanol is diluted with an additional amount (ml) of solvent and tubes for testing moisten the inside of this solution. After drying at each test tube add 2 ml of agaragar. Then each of these tubes is subjected to inoculation of 100 fresh eggs At the contortus in deionized water, the tubes shut cotton wool and placed in an incubator at a temperature of from 34 to 36°and at a humidity of from 60 to 100%. 24 hours after hatching, the larvae add 30 ál of the culture fluid with bacteria so that the bacteria entered together with eggs, could be reproduced. The amount of water should be such that the tubes were filled to about one third. The effect is determined on the basis of the rate of hatching of larvae, larval development until the third age, paralysis or death of the larvae or other stages of development. As typical representatives of the individual compounds 1.17 1.7 and table 1 (page 13 of the description. These compounds and the results obtained are presented below (table 2). Na - At contortus, Tc - Trichostrongylus colubriformis.

In addition, data for some compounds included in the scope of paragraph 1, which prodemo is there the same efficiency in biological tests, showing that they all kill nematodes with a degree of at least 95% at a given concentration (table 3).

1. The use of compounds of the formula

where Ar1and Ar2mean independently from one another unsubstituted phenyl or phenyl which is substituted by halogen;

Q means C(R1)(R2);

R1and R2or independently of one another denote hydrogen, or together with the carbon to which they relate, mean (C2-C6)alkylen;

d means 1;

R3means hydrogen, (C1-C6)alkyl or (C2-C6)quinil;

R4, R5, R6, R7and R8denote each independently of one another hydrogen, (C1-C6)alkyl, or (C3-C6)cycloalkyl; or

R4and R5together imply (C2-C6)alkylen;

W stands for oxygen;

a and b denote independently from one another 0 or 1,

and not necessarily their enantiomers, in the fight against endoparasites pests in warm-blooded productive livestock and domestic animals.

2. Composition for combating endoparasites pests, which contains as active ingredient at least one compound of formula I according to claim 1, the number is the firmness of from 0.1 to 99 wt.% and optionally carriers and/or dispersants in an amount of from 0 to 25 wt.%.

3. The way to deal with endoparasitism pests, where active as a pesticide, at least one compound of formula I according to claim 1 is applied against pests.

4. The use of the compounds of formula I in the method of dealing with parasites of warm-blooded animals.

5. The use of the compounds of formula I according to claim 1 for obtaining a pharmaceutical composition against parasites of warm-blooded animals.



 

Same patents:

The invention relates to derivatives of 2-cyano-3-hydroxyamide formula Iwhere R1represents a group-C(R13)= C(R14, R15), (-CH2)n, R13)C=C (R14, R15), -CCH, where R13- R15is a hydrogen atom or a C1-C3-alkyl; n = 1, 2, 3; R2is a hydrogen atom; R3- R7is a hydrogen atom, nitro or cyano, a halogen atom, a C1-C3the alkyl group of the formula -(CH2)m-CF3or-O-(CH2)mCF3or-S-(CH2)m-CF3where m = 0 or R3-R7group of the formulawhere R8-R12is a hydrogen atom, halogen, CF3

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new compounds of the formula (I): and formula (II): , and to their esters that can be used for treatment of the cellular proliferation disorders. Also, invention relates to a pharmaceutical composition used for modulation of cellular proliferation and comprising compound of the formula (I) or its ester.

EFFECT: valuable medicinal property of compounds and composition.

62 cl, 2 tbl, 25 dwg, 58 ex

FIELD: medicine, cosmetology.

SUBSTANCE: one should apply acid composition onto patient's skin scar, moreover, this composition consists of the following ratio of components, weight%: alpha-hydroacid 0.1-70; gamma-lactone of 2,3-dehydro-L-gulonic acid 0.1-10; 1,2,3-propanetriol 1-10; strontium nitrate 0.5-10, water - the rest. Moreover, for steady penetration of this composition for desired depth against scars and surrounding skin one should treat them with alcoholic solution of beta-hydroxyacid for 3-7 d, and for improved regeneration one should lubricate it with an ointment supplemented with hydroxyacid for 7 d.

EFFECT: higher efficiency of therapy.

2 cl, 2 ex

The invention relates to medicine, namely to the development of new dosage forms for oral administration

Antitumor agent // 2215525
The invention relates to the field of medicine and relates to antitumor agents

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The invention relates to new immunotherapeutics compounds of the formula

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in which X represents-O - or -(CnH2n)-, in which n is 0, 1, 2 or 3; R1represents alkyl containing from 1 to 10 carbon atoms, or monocyclohexyl containing up to 10 carbon atoms; R2represents hydrogen, lower alkyl or lower alkoxy; R3represents (1) phenyl or naphthalene, unsubstituted or substituted by one or more than one Deputy each independently selected from nitro, halogeno, amino, amino substituted by alkyl containing 1-5 carbon atoms, alkyl containing up to 10 carbon atoms, cycloalkyl containing up to 10 carbon atoms, alkoxy containing up to 10 carbon atoms, cycloalkane containing up to 10 carbon atoms, phenyl or methylendioxy; (2) pyridine; each of R4and R5taken separately, represent hydrogen, or R4and R5taken together, represent a carbon-carbon bond; Y is-COZ, -CN or lower alkyl containing from 1 to 5 carbon atoms; Z represents R7represents an alkyl

The invention relates to the field of medicine and is suitable for the treatment of acute and chronic coronary insufficiency, stable and unstable angina, supraventricular tachycardia and arrhythmia, arterial hypertension and hypertensive crisis

The invention relates to derivatives of 2-cyano-3-hydroxyamide formula Iwhere R1represents a group-C(R13)= C(R14, R15), (-CH2)n, R13)C=C (R14, R15), -CCH, where R13- R15is a hydrogen atom or a C1-C3-alkyl; n = 1, 2, 3; R2is a hydrogen atom; R3- R7is a hydrogen atom, nitro or cyano, a halogen atom, a C1-C3the alkyl group of the formula -(CH2)m-CF3or-O-(CH2)mCF3or-S-(CH2)m-CF3where m = 0 or R3-R7group of the formulawhere R8-R12is a hydrogen atom, halogen, CF3

The invention relates to medicine, in particular to Oncology

The invention relates to diphenylethylene derived

FIELD: agents for plant protection useful in controlling of plant diseases of viral, bacterial and fungal etiology as well as in controlling of hookworms and arthropods.

SUBSTANCE: claimed agent contains (wt. %): water soluble product of iodine interaction with organic reagent 7-70; organic solvent 2-20; non-ionic surfactant 1-10; and water 1-90. Abovementioned organic reagent represents polyethylene glycol alkyl or alkylphenyl ester; and organic solvent represents ethylene glycol, triethylene glycol or polyethylene glycol. Weight ratio of iodine and organic reagent is from 1:2 to 1:10. As non-ionic surfactant preferably proxanol or oxyethylated alkylphenol based on polymer distillate is used.

EFFECT: simplified agent for plant protection.

3 cl, 3 tbl, 10 ex

FIELD: agents for plant protection useful in controlling of plant diseases of viral, bacterial and fungal etiology as well as in controlling of hookworms and arthropods.

SUBSTANCE: claimed agent contains (wt. %): water soluble product of iodine interaction with organic reagent 7-70; organic solvent 2-20; non-ionic surfactant 1-10; and water 1-90. Abovementioned organic reagent represents polyethylene glycol alkyl or alkylphenyl ester; and organic solvent represents ethylene glycol, triethylene glycol or polyethylene glycol. Weight ratio of iodine and organic reagent is from 1:2 to 1:10. As non-ionic surfactant preferably proxanol or oxyethylated alkylphenol based on polymer distillate is used.

EFFECT: simplified agent for plant protection.

3 cl, 3 tbl, 10 ex

FIELD: agents for plant protection useful in controlling of plant diseases of viral, bacterial and fungal etiology as well as in controlling of hookworms and arthropods.

SUBSTANCE: claimed agent contains (wt. %): water soluble product of iodine interaction with organic reagent 7-70; organic solvent 2-20; non-ionic surfactant 1-10; and water 1-90. Abovementioned organic reagent represents polyethylene glycol alkyl or alkylphenyl ester; and organic solvent represents ethylene glycol, triethylene glycol or polyethylene glycol. Weight ratio of iodine and organic reagent is from 1:2 to 1:10. As non-ionic surfactant preferably proxanol or oxyethylated alkylphenol based on polymer distillate is used.

EFFECT: simplified agent for plant protection.

3 cl, 3 tbl, 10 ex

FIELD: agents for plant protection useful in controlling of plant diseases of viral, bacterial and fungal etiology as well as in controlling of hookworms and arthropods.

SUBSTANCE: claimed agent contains (wt. %): water soluble product of iodine interaction with organic reagent 7-70; organic solvent 2-20; non-ionic surfactant 1-10; and water 1-90. Abovementioned organic reagent represents polyethylene glycol alkyl or alkylphenyl ester; and organic solvent represents ethylene glycol, triethylene glycol or polyethylene glycol. Weight ratio of iodine and organic reagent is from 1:2 to 1:10. As non-ionic surfactant preferably proxanol or oxyethylated alkylphenol based on polymer distillate is used.

EFFECT: simplified agent for plant protection.

3 cl, 3 tbl, 10 ex

FIELD: agriculture, veterinary.

SUBSTANCE: claimed formulation contains (mass %): deltametrin 0.01-0.05; acetone 5.0-10.0; dimethyl formamide 5.0-10.0; butanol 5.0-10.0; and balance: emulsifier.

EFFECT: preparation of increased activity.

2 cl, 1 tbl, 12 ex

FIELD: agriculture.

SUBSTANCE: claimed method includes treatment of feed crop goat'-rue seeding with aqueous solution of "decys" chemical preparation, 2.5 % concentrated emulsion in amount of 0.5 l/hectare on budding stage in morning at daily average temperature 12°C or more to control of bedbug, flea-beetle, sitona, clover weevil and to increase of seed yield of goat'-rue.

EFFECT: decreased population of insect pest and increased seed yield of goat'-rue.

1 tbl, 1 ex

Acaricide // 2280983

FIELD: agriculture.

SUBSTANCE: invention relates to acaricidal agent containing (mass %): alpha-cypermetrin 0.15-0.25; imiprotrin 0.10-0.35; N-octylbicycloheptadicarboximide 0.8-1.2; triethylene glycol 1.0-2.0; solvent 43.0-50.0; and balance: hydrocarbon propellant.

EFFECT: acaricide of increased effectiveness against red ticks (Rhipiceplalus everti).

2 cl, 4 tbl

FIELD: organic chemistry.

SUBSTANCE: invention describes C2-phenyl-substituted cyclic ketoenols of the general formula: wherein W means hydrogen atom, alkyl with 1-6 carbon atoms; X means alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms; Y means hydrogen atom, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethynyl; Z means hydrogen atom, alkyl with 1-6 carbon atoms under condition that at least one of residues W, X, Y or Z means a chain with at least 2 carbon atoms but only one of residues X and Y can mean alkenyl with 2-6 carbon atoms; CKE means one of the following groups: , , and wherein A means hydrogen atom, alkyl with 1-6 carbon atoms; B means hydrogen atom, alkyl with 1-6 carbon atoms; A and B in common with carbon atom to which they are bound mean cycloalkyl with 5-6 carbon atoms wherein the ring carbon atom can be substituted with oxygen atom and can be substituted with alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms; A and B in common mean group of the formula: D means hydrogen atom or phenyl substituted with fluorine atom if CKE means group of the formula (4); G means hydrogen atom (a) or one of groups of the formula: or wherein R1 means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms; R2 means alkyl with 1-4 carbon atoms; A and Q1 in common mean alkanediyl with 3-4 carbon atoms; Q2 means hydrogen atom. Invention provides preparing compound of the formula (I) possessing with insecticide, acaricide and herbicide activity.

EFFECT: valuable properties of compounds.

2 cl, 8 tbl, 32 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes C2-phenyl-substituted cyclic ketoenols of the general formula: wherein W means hydrogen atom, alkyl with 1-6 carbon atoms; X means alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms; Y means hydrogen atom, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethynyl; Z means hydrogen atom, alkyl with 1-6 carbon atoms under condition that at least one of residues W, X, Y or Z means a chain with at least 2 carbon atoms but only one of residues X and Y can mean alkenyl with 2-6 carbon atoms; CKE means one of the following groups: , , and wherein A means hydrogen atom, alkyl with 1-6 carbon atoms; B means hydrogen atom, alkyl with 1-6 carbon atoms; A and B in common with carbon atom to which they are bound mean cycloalkyl with 5-6 carbon atoms wherein the ring carbon atom can be substituted with oxygen atom and can be substituted with alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms; A and B in common mean group of the formula: D means hydrogen atom or phenyl substituted with fluorine atom if CKE means group of the formula (4); G means hydrogen atom (a) or one of groups of the formula: or wherein R1 means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms; R2 means alkyl with 1-4 carbon atoms; A and Q1 in common mean alkanediyl with 3-4 carbon atoms; Q2 means hydrogen atom. Invention provides preparing compound of the formula (I) possessing with insecticide, acaricide and herbicide activity.

EFFECT: valuable properties of compounds.

2 cl, 8 tbl, 32 ex

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