MXPA06005335A - The use of n-arylhydrazine derivatives for combating pests in and on animals - Google Patents

Abstract

Use of compounds of formula (I) wherein Q is (II), (III), or (IV);X1 is chlorine, bromine, or fluorine;R1, R2 are each independently H, alkyl, alkenyl, alkynyl, or cycloalkyl, alkylamino, dialkylamino, alkylcarbonylamino, alkylsulfonyl, or alkylsulfinyl, wherein the carbon atoms in these groups may be substituted, or R1 and R2 may be taken together to form a ring represented by the structure (V);p,m are 1, 2 or 3;X'is oxygen, sulfur, amino, alkylamino, phenylamino, or methylene;Z is alkyl or phenyl;R3 is H, alkyl, alkenyl, alkynyl, cycloalkyl, wherein the carbon atoms in these groups may be substituted;R, R4 are H or alkyl, alkoxycarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl, wherein the carbon atoms in the these groups may be substituted;A is C-R5 or N;B is C-R6 or N;W is C-R7 or N;with the proviso that one of A, B and W is other than N;R5, R6, R7 are H, halogen, nitro, cyano, amino, mercapto, hydroxy, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, or alkylsulfinyl, wherein the carbon atoms in these groups may be substituted, a 5- to 6-membered aromatic ringsystem which may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which may be substituted;Y is hydrogen, halogen, cyano, nitro, amino, hydroxy, mercapto, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, or alkylsulfinyl, wherein the carbon atoms in these groups may be substituted;n is 0, 1, or 2;for combating parasites in and on animals.

Description

THE USE OF DERIVATIVES OF N-ARILHIDRAZEVA FOR COMBATLR PESTS IN AND ON ANIMALS The present invention relates to the use of hydrazine derivatives of formula I: in which What is it .

X1 is chlorine, bromine or fluorine; , 1 R, R are individually and independently hydrogen, C 1 -doalkyl, C 3 -C 8 alkynyl, C 3 -C 8 alkynyl, or C 3 -Cy 2 cycloalkyl, C 1 alkylamino, di ( alkyl-C? -C6) -amino, alkylcarbonylamino-Ci-Ce, alkylsulfonyl-C? -C6, or alkylsulfinyl-C? -C6, wherein the carbon atoms in these groups can be substituted with: 1 to 3 halogen, hydroxy, nitro, cyano, amino, mercapto, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylocyl, C 1 -C 6 alkylsulfonyl, C 1 -C 5 alkylsulfinyl; -C6, haloalkylsulfonyl-Ci-Cß, haloalkylsufinyl-CrCß, or C3-C6 cycloalkyl which may be substituted with 1 to 3 R groups, or R # is halogen, cyano, nitro, hydroxy, mercapto, amino, alkoxy-Ci -Cd, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, haloalkoxy-CrCe, C 1 -C 6 alkylthio, or C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfinyl, aicylamino -CrCe, di (C 1 -C 6 alkyl) -amino, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, or di (C 1 -C 6) alkylaminocarbonyl; formyl, alkylcarbonyl-d-Ce, C (= O) NRaRb, CO2Rc, Rd, Re, phenyl which may be substituted with 1 to 3 R # groups, or pyridyl which may be substituted with 1 to 3 R # groups, Ra, Rb, Rc are individually and independently hydrogen or C-C-alkyl which may be substituted with 1 to 3 R # groups; R ^ s NR'R 'or R, R are individually and independently hydrogen or C 1 -C 4 alkyl which may be substituted with 1 to 3 R # groups; p, m are individually and independently 0, 1, 2, or 3, with the proviso that p and m both are not 0. X is oxygen, sulfur, amino, alkylamino-C? -C4? or phenylamino, or, if p is 0 then X can also be phenoxy or C 1 -C-alkoxy; r is 0 or 1; Re is R, Rq are individually and independently hydrogen or C -C alkyl which can be substituted with 1 to 3 R # groups; or R1 and R2 can be taken together to form a ring represented by the structure p, m are 1, 2 or 3; X 'is oxygen, sulfur, amino, alkylamino-C? -C, phenylamino, or methylene; Z is C 1 -C alkyl or phenyl; R 3 is hydrogen, C 1 -C 0 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 7 cycloalkyl, wherein the carbon atoms in these groups may be partially or fully halogenated or substituted with 1 to 3 cyano, nitro, hydroxy, mercapto, amino, C alquilo-C6 alkyl, Cs-Ce cycloalkyl, CrCß alkoxy, C6 alkylamino, di (C6 alkyl) -amino, alkylthio groups -CrCß, alkylsulfony-C-? - C-6, or alkylsulphinyl-CrCß, wherein the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, an aromatic ring system with 5 to 6 members which may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which may be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 C 1 -C 6 alkyl, C 1 6 alkylthio, alkylsulfonyl C ? -C6, alkylsulfinyl-C-? -C-6, alkoxy-Ci-C?, Nitro, or cyano, where the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, or phenoxy, the It can be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 C6 alkyl groups, C12 alkylthio, C5 alkyl sulphonyl C-6, alkylsulfinyl-CrC ?, alkoxy-CrCβ, nitro or cyano, wherein the carbon atoms in these groups may be substituted with 1 to 3 halogen atoms, or a 3 to 6 membered ring system, saturated or partially unsaturated, which contains 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen and which may be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-C-α-C6, alkylthio-CrCd groups , alkylsulfonyl-Ci-C ?, alkylsulfinyl-C? -C6, alkoxy-CiC ?, nitro or cyano, wherein the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, a saturated or partially unsaturated ring system of 3 to 6 members, which contains 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen and which is unsubstituted or substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-d-Cß, alkylthio-Ci-Cß, alkylsulfonyl-CrC ?, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkoxy, nitro or cyano groups, wherein the carbon atoms in these groups can be substituted to 3 halogen atoms, R, R4 are individually and independently hydrogen or d-Cß alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 aicylaminocarbonyl, or di (C 1 -C 6 alkyl) -aminocarbonyl, wherein Carbon atoms in these groups can be substituted with 1 to 3 R # groups; A is C-R5 or N; B is C-R6 or N; W is C-R7 or N; with the proviso that one of A, B and W is different from N; R 5, R 6, R 7 are individually and independently hydrogen, halogen, nitro, cyano, amino, mercapto, hydroxy, C 1 -C 10 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 cycloalkyl C6, alkoxy-dC ?, alkylamino-C- | -C6, di (C6-alkyl) -amino, alkylthio-Ci-Ce, alkylsulfonyl-CrC6, or alkylsulfinyl-CrC6, wherein the carbon atoms in these groups can be substituted with 1 to 3 groups R # a system of aromatic rings of 5 to 6 members which can contain from 1 to 4 heteroatoms selected among oxygen, sulfur and nitrogen and which can be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-d-Cß, haloalkyl-C-pCe, C 1 -C 6 alkyl, haloalkylthio-d-Cß, C 1 -C 6 alkylsulfonyl, alkylsulfinyl-Ci-Cd, haloalkylsulfonyl-Ci-Cβ, haloalkylsulfinyl-C? -C6, alkoxy-CrCe, haloalkoxy-C? -C6, mercapto, hydroxy, amino, nitro or cyano, wherein the carbon atoms in these groups can be substituted with 1 to 3 R # groups; Y is hydrogen, halogen, cyano, nitro, amino, hydroxy, mercapto, C6-alkyl, C2-C2 alkenyl, C2-alkynyl, C3-C6 cycloalkyl, C6-alkoxy, alkylamino- CrC6, di (C? -C6) alkylamino, alkylthio-Ci-C?, Alkylsulfonyl-d-C6, or C -C6 alkylsulfinyl, where the carbon atoms in these groups may be substituted with 1 to 3 R # groups; n is 0, 1 or 2; or the enantiomers or diastereomers, salts or esters acceptable from the veterinary point of view thereof, to combat parasites in and on animals. It is generally an objective of agronomists and veterinarians to possess sufficient means to control parasites, when they try to invade or attack animals. An object of the present invention is to provide new methods for the control of parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is to provide pesticides for animals that can be used in lower doses than existing pesticides. Another object of the invention is to provide pesticides for animals which provide lasting residual control of the parasites.

These objects are achieved in whole or in part by the present invention. The invention also relates to compositions containing an amount effective to combat parasites of the compounds of formula I and an acceptable carrier, to combat parasites in and on animals. The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises administering or applying orally, topically or parenterally to animals an amount effective to fight parasites of a compound of formula I or a composition that comprises it. The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting a. the animals against infestation or infection by parasites which comprises an amount effective to fight parasites of a compound of formula I or a composition comprising it. Insecticidal and acaricidal activity in the protection of the cultures of some of the compounds of formula I has been described in EP-A 604 798, and also in J. A Furch et al., "Amidrazones: A New Class of Coleopteran Insecticides" , ACS Symposium Series 686, Am. Chem. Soo, 1998, Chapter 18, p. 178 ff, and also in D. G. Kuhn et al., "Cycloalkyl-substituted Amidrazones: A Novel Class of Insect Control Agents ", ACS Symposium Series 686, Am. Chem. Soc, 1998, Chapter 19, page 185. The activity of the compounds against agricultural pests does not suggest their suitability for the control of endo- and ectoparasites. in and on animals which requires, for example, low, non-emetic dosages, in the case of oral application, metabolic compatibility with the animal, low toxicity and safe handling.

Surprisingly it has now been discovered that the compounds of the formula I are suitable for combating endo- and ectoparasites in and on animals. The compounds of formula I can be prepared according to the preparation methods described or referenced in EP-A 604 798 or their modifications. In the definition of the formula I shown above, the substituents have the following meanings: "Halogen" shall be taken to mean fluorine, chlorine, bromine and iodine. The term "alkyl" as used herein refers to a saturated, branched or unbranched hydrocarbon group having from 1 to 10 carbon atoms, especially C 1 -C 6 alkyl such as methyl, ethyl, propyl, 1- methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1- dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.

The term "haloalkyl" as used herein refers to straight or branched chain alkyl groups having from 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in the these groups can be replaced by halogen atoms according to the aforementioned, for example haloalkyl-dd, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluomethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl; "Alkoxy" refers to a straight or branched chain alkyl group having 1 to 4 or 6 carbon atoms (as mentioned above) linked through an oxygen linkage, at any bond in the alkyl group.

Examples include methoxy, ethoxy, propoxy and isopropoxy. Likewise, the terms "alkylthio", "alkylamino", "dialkylamino", "alkylsulfonyl" and alkylsulfinyl "refers to an alkyl group straight chain or branched alkyl having 1 to 4 or 6 carbon atoms (as mentioned above) bound through a sulfur linkage, -NH-, -N-, -S (= O) 2-, or S (= O), respectively. The term "alkenyl" as used herein means a hydrocarbon, unsaturated, branched or unbranched group having from 3 to 10 carbon atoms and a double bond at any position, such as C3-C6 alkenyl such as 1 -propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyi, 2 -methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-penteniIo, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-Hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2- pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenium, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1, 1-dimethyl-3- butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-buteniIo, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2- butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1- ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; "Cycloalkyl" refers to rings of saturated carbon atoms of 3 to 6, 8, 10 or 12 members, monocyclic, for example C3-C8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. A 5-6 membered aromatic ring system containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen, for example means 5-membered hetaryl, containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom, for example, furyl, thienyl, pyrrolium, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, and tetrazolyl; or hetaryl 6 members, containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and one sulfur atom or oxygen, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl; system saturated or partially unsaturated rings, 3 to 6 members which contains 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen is for example a ring system of 3 to 6 membered saturated containing 1 to 3 heteroatoms selected between nitrogen and oxygen, such as aziridine, pyrrolidine, tetrahydrofuran, tetrahydropyran, or piperidine. By the term "salts acceptable from the veterinary point of view" is meant salts whose anions are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, for example, formed by the compounds of formula I containing a basic nitrogen atom, for example an amino group, include salts with inorganic acids, for example hydrochlorides, sulfates, phosphates and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfenic acid, methanesulfonic acid and succinic acid. With respect to the intended use of the compounds of formula I, particular preference is given to the following meanings of the substituents, in each case alone or in combination: Preference is given to compounds of formula I in which A denotes C-R5 .

Additionally, preference is given to compounds of formula I in which B denotes C-R6. Preference is also given to compounds of formula I in which W denotes C-R7. Particular preference is given to compounds wherein A denotes C-R5, B denotes C-R6, and W denotes C-R7. Also, preference is given to compounds of formula I wherein R5 is halogen or haloalkyl d-Cß, with halogen, especially chlorine, being most preferred. Preference is also given to compounds of formula I wherein R6 is hydrogen or halogen, especially hydrogen. Preference is furthermore given to compounds of formula I wherein R7 is halogen or haloalkyl d-C6, preferably haloalkyl d-C6, especially trifluoromethyl. Still further, preference is given to the compounds of formula I wherein Y is in the ortho position and is halogen or C-Cß haloalkyl. Particular preference is given to the compounds of formula 1 wherein Y is halogen, especially chloro.

Preference is given to compounds of formula I wherein n is 1. Preference is also given to compounds of formula I wherein Q denotes -N = [C (NR1R2) R3]. Additionally, preference is given to the compounds of formula I wherein X1 is chlorine. Preference is also given to compounds of formula I wherein R denotes alkyl d-d or hydrogen, preferably hydrogen. Preference is also given to compounds of formula I in which R and R 2 each independently is hydrogen, alkyl d-do which may be substituted by C 1 -C 4 alkoxy, or C 3 -C 10 cycloalkyl which may be substituted with 1 to 3 halogen. Additionally, preference is given to compounds of formula I in which R1 and R2 each independently is hydrogen, C4 alkyl, or cycloalkyl Especially preferred compounds are the compounds of formula I in which R 1 is hydrogen and R 2 is C 1 -C 10 alkyl which may be substituted with d-C alkoxy, or C 3 -cycloalkyl which may be substituted with 1 to 3 halogen. Compounds of formula I in which R 1 is hydrogen and R 2 is d-C 4 alkyl or C 3 -C 6 cycloalkyl are given special preference. In addition, preference is given to compounds of formula I in which R 3 is unsubstituted C 1 -C 10 alkyl or cycloalkyl d-do. e 'cua' may be substituted with 1 to 5 halogen atoms and / or 1 to 3 d-C6 alkyl groups. Particularly preferred are compounds of formula I in which R3 is tert-butyl.

Additionally, particularly preferred are the compounds of formula I in which R3 is cyclopropyl which may be substituted with d-C6 alkyl or halogen, especially 1-methyl-2,2-dichlorocyclopropyl. In addition, preference is given to compounds of formula I in which R4 is hydrogen or alkyl d-d- With respect to their use, particular preference is given to the compounds I-A compiled in the tables that appear later. Also, the groups mentioned for a substituent in the tables are by themselves, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question. With respect to its use, particular preference is also given to the adducts of hydrochloric acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfenic acid, methanesulfonic acid and succinic acid of the compounds of the tables below. Some of the compounds of formula I are new. These are also an object of this invention. Table 1 The compounds of the formula I-A in which R3 is methyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A.

Table 2 The compounds of the formula I-A in which R3 is ethyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A.

Table 3 Compounds of formula l-A in which R3 is ethyl and the combination of R1, R2, R5, R6, R7 and Yn correspond in each case to a row of Table A.

Table 4 The compounds of the formula I-A in which R3 is propyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A.

Table 5 The compounds of the formula lA in which R3 is isopropyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A. Table 6 The compounds of the formula lA in wherein R3 is isobutyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of the Table A.

Table 7 The compounds of the formula i-A in which R3 is ter-butiio and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of ia Table A. Table 8 The compounds of the formula IA in which R is neopentyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A. Table 9 The compounds of the formula I wherein R 3 is cyclopropyl and the combination of R 1, R 2, R 5, R 6, R 7 and Y n corresponds in each case to a row of Table A. Table 10 Compounds of formula lA in which R 3 is 1, 1-dimethyl-propyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of the Table A. Table 1 The compounds of the formula IA in which R3 is cyclopropyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A. Table 12 the formula IA in which R3 is 2,2-dichloro-cyclopropyl and the combination of R, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A. Table 13 The compounds of the formula lA wherein R3 is 2,2-dib-cyclopropyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A. Table 14 The compounds of the formula IA in which R3 is 1-methyl-cyclopropyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A.

Table 15 The compounds of the formula IA in which R3 is 1-methyl-2,2-dic.o-cyclopropyl and the combination of R1, R2, R5, Rd, R7 and Yp corresponds in each case to a row of Table A Table 16 The compounds of the formula IA in which R3 is 1-methyl-2,2-dibcyclopropyl and the combination of R1, R2, R5, R6, R7 and Yn corresponds in each case to a row of Table A.

Table A ? z 02 if I heard you? Z 02 ? \ 01 ZZ? Z oz? \ 01 ee? Z 02 ?? 01 te 9Z oz ?? I heard e sz oz SI 01 9e? Z 02 ?? I heard ze? z 02 ci 01 8e? Z 02 YES OT 6e C2 02 YES 01 OP 52 02 YES 01 It? Z 02 if I heard 2 efr S2 02 SI 01 S2 02 SI 01 9F S2 02 I 01 9 S2 02 I 01 Zfr S2 02 SI 01 8 The compounds of the formula I-B are particularly preferred with respect to the intended use in the present invention. wherein R7 is chloro or trifluothyl; R5 and Y are individually and independently chlorine or bne; R2 is d-d alkyl, C3-C6 alkenyl, C3-C6 alkynyl, or C3-d cycloalkyl which may be substituted with 1 to 3 halogen atoms, or d-C4 alkyl which is substituted with d-C alkoxy; R31 and R32 are alkyl d- or they may be taken together to form C3-d cycloalkyl which may be unsubstituted or substituted with 1 to 3 halogen atoms; R33 is hydrogen or d-d alkyl, or its enantiomers or salts acceptable fthe veterinary point of view. Preference is given to compounds of formula I-B in which R7 is trifluothyl.

Further preference is given to the compounds of formula I-B wherein Y and R5 are both chloro. Also preferred are compounds of formula I-B wherein R 2 is d-d alkyl, especially ethyl. Further preference is given to the compounds of formula I-B in which R31 and R32 are both methyl. Additionally, compounds of formula I-B in which R31 and R form a cyclopropyl ring which is unsubstituted or substituted by 1 to 3 halogen atoms, especially chlorine and bne, are referred to. In addition, compounds of formula I-B in which R31 and R32 form a cyclopropyl ring which is substituted by 2 halogen atoms are particularly preferred. Moreover, compounds of formula I-B in which R31 and R32 form a cyclopropyl ring which is substituted with 2 chloro atoms are preferred. Particularly preferred are compounds of formula l-B in which R31 and R32 forms a 2,2-dichlorocyclopropyl ring. Additionally, preference is given to the compounds of formula I-B in the 33 is alkyl d-d, especially methyl. Particularly preferred are compounds of formula l-B in which R31, 33 R32 and R33 ssoonn ttooddooss mmeettiilloo. Also, particularly preferred are compounds of formula I-R31, R32 and R33 form a 1-methyl-2,2-dichlorocyclopropyl moiety. Preference is further given to compounds of formula I-B in which R7 is trifluoromethyl; Y and R5 are independently and independently chlorine or bromine; R2 is C6 alkyl; R31 and R32 are d-C6 alkyl or can be taken together to form d-C6 cycloalkyl which is substituted with 1 to 2 halogen atoms; R33 is alkyl d-d; or its enantiomers or salts acceptable from the veterinary point of view. Particular preference is given to N-ethyl-2,2-dimethylpropionamid-2- (2,6-dichloro-a, a-trifluor-p-tolyl) hydrazone and N-Ethyl-2,2-dichloro-1- methylcyclopropan-carboxamide-2- (2,6-dichloro-a, a, a-trifluor-p-tolyl) hydrazone. Additionally, particular preference is given with respect to the use in the present invention to the compound of formula 1-1 (N-ethyl-2,2-dimethylpropionamide-2- (2,6-dichloro-a, a, a-trifluor-p -tolol) -hydrazone): Additionally, particular preference is given with respect to the use in the present invention to the compound of formula I-2 (N-Ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2- (2,6-dichloro-a, , α-trifluor-p-tolyl) hydrazone): The compounds of formula I and the compositions comprising them are preferably used to control or prevent infestations and infections in animals including warm-blooded animals (including humans) and fish. The compounds are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffalo, donkeys, deer. and reindeer, and also in animals with fur such as mink, chinchilla and raccoon, birds such as chickens, geese, turkeys and ducks and fish such as freshwater and saltwater fish such as trout, carp and eels. The compounds of formula I and the compositions comprising them are preferably used to control and prevent infestations and infections in domestic animals, such as dogs or cats. Infestations in warm-blooded animals and fish include, but are not limited to, louse, itchy louse, mites, nasal prongs, sheep mites, spicy flies, mossy flies, flies, myiasitic fly larvae, chiggers, mosquitoes, mosquitoes and flies. The compounds of formula I and the compositions comprising them are suitable for the systemic and / or non-systemic control of ecto- and / or endoparasites. They are active against all or some stages of development. The compounds of formula I are especially useful for combating ectoparasites. The compounds of formula I are especially useful for controlling parasites of the following orders and species, respectively: fleas (Siphonaptera), for example Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irrítans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria - Blattodea), for example Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta oríentalis, flies, mosquitoes (Diptera), for example Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens , Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, macellaria Chrysomya, Chrysops discalis, Chrysops siliceous, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthrop ophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycory pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys caicitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (ftirápteros), for example Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Soleno potos capillatus. parasitic mites and mites (Parasitiformes): mites (Ixodida), for example Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Omithodorus turicata and parasitic mites (Mesostigmata) , for example Ornithonyssus bacoti and Dermanyssus gallinae, Actinédids (Prostigmata) and Acaridids (Astigmados) for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp. ., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp, Insects (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus, Anópluros, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp., Mallophagida (suborders Amblycerina and Ischnocerina), for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., And Felicola spp., Roundworm nematodes: roundworms and Trichinosis (Trichosyringida), for example Trichinellidae (Trichinella spp.), (TrichuridaeJ Trichuris spp., Capillaria spp., Rhabditida, for example Rhabditis spp, Strongyloides spp., Helicephalobus spp, Strongylida, for example Strongylus spp., Ancylostoma spp., Necator amerícanus, Bunostomum spp. (Intestinal worm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp. , Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale, Intestinal worms (Ascarid), for example Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Ascaride), Toxocara canis, Toxascaris leonine, Skrjabinema spp., And Oxyuris equi, Camallanida, by example Dracunculus medinensis (species of filaria) Spirurida, for example Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp., Worms with spiny heads (Acanthocephala), for example Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Ondeola spp, Planarians (Plathelminthes): Worms (Trematodes), for example Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp. , Alaria alata, Paragonimus spp., And Nanocyetes spp, Cercomeromorpha, in particular Cestodos (Tenias), for example Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., And Hymenolepis spp. The compounds of formula I and the compositions containing them are particularly useful for the control of pests of the orders Diptera, Siphonaptera and Ixodida. Also, the use of the compounds of formula I and compositions containing them to combat mosquitoes is especially preferred. The use of the compounds of formula I and compositions containing them to combat fleas is a further preferred embodiment of the present invention. In addition, the use of the compounds of formula I and the compositions containing them to combat fleas is especially preferred.

The use of the compounds of formula I and compositions containing them to combat mites is a further preferred embodiment of the present invention. The compounds of formula I are also especially useful for combating endoparasites (roundworm nematodes, spiny head worms and planarians). The administration can be carried out both prophylactically and therapeutically. The administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically / dermally or parenterally. For oral administration to warm-blooded animals, the compounds of formula I can be formulated as animal feeds, premixes of animal feeds, animal feed concentrates, pills, solutions, pastes, suspensions, potions, gels, tablets, boluses and capsules Additionally, the compounds of formula I can be administered to the animals in their drinking water. For oral administration, the selected dosage form should provide the animal 0.01 mg / kg to 100 mg / kg body weight of the animal per day of the compound of formula I, preferably 0.5 mg / kg to 100 mg / kg of body weight of the animal per day. Alternatively, the compounds of formula I can be administered to animals parenterally, for example, by intra-ruminal, intramuscular, intravenous or subcutaneous injection. The compounds of formula I can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of formula I can be formulated in an implant for subcutaneous administration. Additionally, the compound of formula I can be administered transdermally to the animals. For parenteral administration, the chosen dosage form should provide the animal 0.01 mg / kg to 100 mg / kg body weight of the animal per day of the compound of formula I. The compounds of formula I can also be applied topically to the animals in the form of baths, powders, collars, medallions, sprays, shampoos, formulations of local application and pouring and in ointments or emulsions oil in water or water in oil. For topical application, baths and sprays generally contain 0.5 ppm up to 5,000 ppm and preferably 1 ppm up to 3,000 ppm of the compound of formula I. In addition, the compounds of formula I can be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep. The suitable preparations are: - Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, local pouring formulations, gels; - Emulsions and suspensions for oral or dermal administration; semi-solid preparations; - Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base; - Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalations and shaped articles that contain the active compound. Suitable compositions for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding other ingredients such as acids, bases, buffer salts, preservatives and solubilizers. The solutions are filtered and sterile loaded. Suitable solvents are physiologically tolerable solvents such as water, alkanes such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof. The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection. Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation.

Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Suitable preservatives are benzyl alcohol, trichlorobutanol, esters of p-hydroxybenzoic acid, and n-butanol. Oral solutions are administered directly. The concentrates are administered orally after or before dilution at the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as previously described for solutions for injection, sterile procedures are not necessary. Solutions for use on the skin are applied in the form of drip, scattered, rubbed, sprayed or sprayed on the skin.

The solutions for use on the skin are prepared according to the state of the art and according to what was described above for solutions for injection, sterile procedures are not necessary. Other suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ether, for example dipropylene glycol monomethyl ether, ketones such as acetone, methyl ethyl ketone, aromatic hydrocarbons, vegetable oils and synthetics, dimethylformamide, dimethylacetamide, transcutol, solketal, propylene carbonate, and mixtures thereof. It may be advantageous to add thickeners during the preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates. Those that are applied or spread on the skin or introduced into body cavities. The gels are prepared by treating solutions which have been prepared as described in the case of injection solutions with sufficient thickener that a transparent material having an ointment-like consistency is obtained. The thickeners used are the thickeners provided above. Pouring formulations are poured or sprayed over limited areas of the skin, the active compound penetrates the skin and acts systemically. Pouring formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable solvents or solvent mixtures compatible with the skin. If appropriate, other auxiliaries such as colorants, substances that promote bioabsorption, antioxidants, light stabilizers, adhesives are added.

The suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, butyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N-methylpyrrolidone , 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane and glycerol formal. Suitable colorants are all colorants allowed for use in animals and which can be dissolved or suspended. Substances that promote adequate absorption are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and their copolymers with polyethers, fatty acid esters, triglycerides, fatty alcohols. Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylhydroxyanisole, tocopherol. Suitable light stabilizers are, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin. The emulsions can be administered orally, dermally or as injections. The emulsions are of the water-in-oil type or the oil-in-water type.

They are prepared by dissolving the active compound in either the hydrophobic or hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as dyes, substances promoting absorption, preservatives, antioxidants, light stabilizers, substances that increase viscosity. Suitable hydrophobic phases (oils) are: liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric biglyceride, mixture of triglycerides with vegetable fatty acids. chain length C8-C12 or other specially selected natural fatty acids, mixtures of partial glycerides of saturated or unsaturated fatty acids possibly also containing hydroxyl, mono and diglycerides groups of C8-do fatty acids, - esters of fatty acids such as ethyl stearate, adipate of di-n-butyryl, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C3, isopropyl myristate, isopropyl palmitate, acid esters caprylic / capric saturated fatty alcohols of chain length C12-Ci8, stearate Sopropyl, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, esters of waxy fatty acids such as fats of the coccygeal gland of synthetic duck, dibutyl phthalate, diisopropyl adipate, and mixtures of esters related thereto, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof. Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof. Suitable emulsifiers are: non-ionic surfactants, for example polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, aikilphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulphates, monoethanolamine salt of mono / dialkyl polyglycol ether orthophosphoric acid ester; cation-active surfactants, such as cetyltrimethylammonium chloride. Suitable additional auxiliaries are: substances which increase the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methylvinyl ether and anhydride maleic, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the mentioned substances. The suspensions can be administered orally or topically / dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with the addition of other auxiliaries such as wetting agents, colorants, bioabsorption promoting substances, preservatives, antioxidants, light stabilizers.

The liquid suspension agents are all solvents and homogeneous solvent mixtures. Suitable wetting agents (dispersants) are the emulsifiers provided above. Other auxiliaries which may be mentioned are those provided above. Semi-solid preparations can be administered orally or topically / dermally. They differ from the suspensions and the emulsions described above only by their superior viscosity. For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with the addition of auxiliaries, and brought to the desired shape. Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. The inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, titanium oxide, silicic acids, clay soils, colloidal or precipitated silica, or phosphates. The organic substances are, for example, sugar, cellulose, food substances and foods such as milk powder, animal feed, grain flours and shredded rations, starches. Suitable auxiliaries are preservatives, antioxidants and / or dyes which have been mentioned above. Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration promoting substances such as crosslinked starch or polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose. .

The compositions which can be used in the invention can generally comprise between about 0.001 and 95% of the compound of formula I. Generally, it is favorable to apply the compounds of formula I in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg a 50 mg / kg per day. The ready-to-use preparations contain the compounds that act against the parasites, preferably the ectoparasites, in concentrations of 10 ppm to 80 weight percent, preferably between 0.1 and 65 weight percent, more preferably between 1 and 50 weight percent. percent by weight, more preferably between 5 and 40 percent by weight. The preparations which are diluted before use contain the compounds that act against the ectoparasites in concentrations of 0.5 to 90 weight percent, preferably 1 to 50 weight percent. In addition, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 percent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent in weigh. In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I are applied dermally / topically. In a further preferred embodiment, topical application is carried out in the form of shaped articles containing compounds such as collars, medallions, ear tags, bands to attach to body parts, and adhesive strips and sheets. In general, it is favorable to apply solid formulations which release the compounds of formula I in total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, more preferably 25 mg / kg to 160 mg / kg body weight of the animal treated over the course of three weeks.

For the preparation of the shaped articles, thermoplastics and flexible plastics are used as well as elastomers and thermoplastic eiastomers. Suitable plastics and elastomers are polyvinyl, polyurethane, polyacrylate resins, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester, which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as the methods of Preparation for the shaped articles are provided for example in WO 03/086075. The active compounds can also be used as a mixture with synergists or with other active compounds which act against pathogenic endo- and ectoparasites. The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, although not to impose any limitations: Organophosphates: Acefato, Clorfenvinfós, Diazinón, Diclorvós, Dicrotofós, Dimethoate, Ethion, Fenitrothion, Fenthion, Isoxatión, Malathion, Fentoato, Fosalona, Fosmet, Foxim, Pirimifós-methyl, Profenofós, Protiófós, Sulprofós, Triazofós, Trichlorfón, Quintiophos, Coumafós, Clorfoxim, Bromofós-etiio, 2,3-p-DioxanditioI- S, S-bis (O, O-dietilfosforoditionat); Carbamates: Alanicarb, Benfuracarb, Carbaryl, Carbosulfan, Phenoxycarb, Furathiocarb, Indoxacarb, Triazamate; Pyrethroid: alpha-Cypermethrin, Deltamethrin, Etofenprox, Fenvalerate, Cihalotrina, Lambda-Cihalotrina, Permetrina, Silafiuofen, Tau-Fluvalinato, Tralometrina, Zeta-Cypermetrina, Flumetrina, Ciflutrina and its enantiómeros and estereómeros, Cipermetrina; Regulators of the growth of arthropods: a) inhibitors of the synthesis of chitin: benzoylureas: Clorfluazuron, Cromazine, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron; Buprofezin, Diofenolan, Hexitiazox, Etoxazole, Clofentazine; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoides: Pyriproxyfen, Metoprene, Phenoxycarb; d) inhibitors of iipidic biosynthesis: Spirodiclofen; Neonicotinoids: Acetamiprid, Clotianidin, Flonicamid, lmidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Synthetic compounds for coccidiosis, polyether antibiotics: Amprolium, Robenidin, Toltrazuril, Monensin, Salinomicin, Maduramicin, Lasalocid, Narasin, Semduramicin; Miscellaneous: Abamectin (Avermectins), Acequinocil, Amitraz, Azadiractin, Bifenazate, Bacillus thuringiensis, Bacillus subtilis, Cartap, Clorfenapyr, Clordimeform, Ciromazine, Diafentiuron, Dinetofuran, Diofenolan, Emamectin, Endosulfan, Epsiprantel, Etiprole, Fenazaquin, Fipronil, Formetanato, Formetanato hydrochloride, Hydramethion, Indoxacarb, 4-. { (2Z) -2- ( { [4- (trifluor-methoxy) anilino] carbonyl, hydrazono) -2- [3- (trifluoromethyl) -phenyl] ethyl} Benzo-nitrile, L-2,3,5,6-tetrahydro-6-phenyl-imidazothiazole, Levamisole, Milbemectin (Milbemycins), Moxidectin, Praziquantel, Pirantel, Pyridaben, Pimetrozine, Selamectin, Spinosad, Sulfur, Tebufenpirad, and Tiociclam. In general, "effective amount to fight parasites" means the amount of active ingredient necessary to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction or otherwise decrease of occurrence and activity of the target organism. The amount effective to fight parasites may vary for the various compounds / compositions used in the invention. An effective amount for controlling parasites of the compositions will also vary according to the prevailing conditions such as the desired parasiticidal effect and the duration, the target species, mode of application and the like. Examples of action against parasites 1. Selection method for testing contact activity against barn fly, yellow fever mosquito, household mosquito, malaria mosquito, cat flea and brown dog mite by contact with glass. glass jars (20 ml scintillation flasks) with 0.5 ml of an active ingredient solution in acetone. Each bottle was rolled uncovered for almost 10 minutes to allow the i. to. completely covers the bottle and to allow a complete drying of the acetone. Insects or mites were placed in each jar. The flasks were kept at 22 ° C and were observed to determine the effects of the treatment at various time intervals. The results are presented in Table I. 2. Selection method for testing the contact activity against yellow fever mosquito larvae, southern home mosquito, and malaria mosquito by means of water treatment. plates of wells as test grounds. The active ingredient was dissolved in acetone and diluted with water to obtain the necessary concentrations. The final solutions containing approx. 1% acetone was placed in each well. Approximately 10 mosquito larvae (4th chrysalis) in 1 ml of water were added to each well. The larvae were fed a drop of liver powder each day. The dishes were covered and kept at 22 ° C. Mortality was recorded daily and dead larvae and live or dead nymphs were removed daily. At the end of the test, the remaining live larvae were recorded and the mortality percentage was calculated. The results are shown in Table I.

Each trial was replicated at least 3 times. Results The tests carried out with the compounds of formula 1-1 and I-2 showed the following results: Table I. Activity against various species. 3. Activity against the cat flea in an "artificial dog" apparatus The active ingredient was dissolved in acetone and mixed with an appropriate volume of blood from defibrated cattle. 5 ml of treated blood was poured into a feeding chamber equipped with a paraffin wax film membrane. The chamber with the treated blood was placed on a flea feeding chamber. The test was repeated for each of the 5 concentrations of the doses of each of the active ingredients. The effects of the treatment, including knockdown, non-feeding after 24 hours, egg-laying, etc., were observed at various intervals. Control tests were carried out with acetone / blood mixtures. Results The tests carried out with 100 ppm of the compounds of formula I-1 and I-2 showed an extermination rate of more than 60% of Ctenocephalides felis.

Claims (10)

1. CLAIMS Having thus specially described and determined the nature of the present invention and the manner in which it is to be put into practice it is claimed to claim as property and exclusive right: 1. The use of the compounds of formula I in which What is it X1 is chlorine, bromine or fluorine; R 1, R 2 are independently and independently hydrogen, C 1 -C 6 alkyl, C 3 -C 3 alkenyl, C 3 -C 8 alkynyl, or cycloalkyl-dC-12, alkylamino-dd, di (alkyl) -C6) -amino, alkylcarbonylamino-Ci-d, alkylsulfonyl-dd, or alkylsulfinyl-C? -C6, wherein the carbon atoms in these groups can be substituted with; 1 to 3 halogen, hydroxy, nitro, cyano, amino, mercapto, alkoxy-dd, haloalkoxy-dd, alkylthio-d-C6, haloalkytiio-dd, alkylsulfonyl-d-C6, alkylsulfinyl-C? -C6, haloalkylsulfonyl-dd, haloalkylsulfonyl-C? -C6, or cycloalkyo-C3-C6 which can be substituted with 1 to 3 R # groups, or R # is halogen, cyano, nitro, hydroxy, mercapto, amino, alkoxy-dd, alkenyloxy- dd, alkynyloxy-dd, haloalkoxy-dd, alkylthio-dd, or haloacylthio-dd, alkylsulfonyl-dd, alkylsulfinyl-dd, alkylamino-C? -C6, di (alk-C6) -amino, alkylcarbonyl-dd, alkoxycarbonyl -dd, or di-alkyl (C C6) aminocarbonyl; formyl, alkylcarbonyl-Ci-C ?, C (= O) NRaRb, CO2Rc, Rd, Re, phenyl which may be substituted with 1 to 3 R # groups, or pyridyl which may be substituted with 1 to 3 R # groups , Ra, Rb, Rc are individually and independently hydrogen or alkyl-dd which can be substituted with 1 to 3 R # groups; Rdes NR¡Rj or R ', RJ are individually and independently hydrogen or a-qu-d-C4 which can be substituted with 1 to 3 R # groups; p, m are individually and independently 0, 1, 2, or 3, with the proviso that p and m both are not 0; X is oxygen, sulfur, amino, alkylamino-C? -C4, or phenylamino, or, if p is 0 then X can also be phenoxy or alkoxy-d-d; r is 0 or 1; Re is Rk, Rq are individually and independently hydrogen or alkyl-d-C4 which can be substituted with 1 to 3 R # groups; or R1 and R2 can be taken together to form a ring represented by the structure p, m are 1, 2 or 3; X 'is oxygen, sulfur, amino, alkylamino-C? -C, phenylamino, or methylene; Z is aikyl-d-d or phenyl; R 3 is hydrogen, C 1 -C 4 alkyl, alkenyl-d-do, C 2 -C 8 alkynyl, C 3 -C 6 cycloalkyl, wherein the carbon atoms in these groups can be partially or totally halogenated or substituted with 1 to 3 groups cyano, nitro, hydroxy, mercapto, amino, alkyl-Ci-d, cycloalkyl-dd, alkoxy-dd, alkylamino-dd, di (alkyl-C? -Ce) -amino, alkylthio-C-rd, alkylsulfonyl-dd, or C al-C6 alkylsulfinyl) wherein the carbon atoms in these groups may be substituted with 1 to 3 halogen atoms, an aromatic ring system with 5 to 6 members which may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which may be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-d-C6, alkylthio-dd, alkylsulfonyl-dd, alkylsulfinyl-dd, alkoxy-dd, nitro, or cyan, where the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, or phenoxy, which may be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-dd groups, alkylthio-dd, alkylsulfonyl-d-CQ, alkylsulfinyl-Ci-d, alkoxy- dd, nitro or cyano, wherein the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, or a 3 to 6 membered ring system, saturated or partially unsaturated, which contains 1 to 3 selected heteroatoms between oxygen, sulfur, and nitrogen and which may be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-d-C6, alkylthio-C6, aminosilylonitrile-dd, alkylsulfinium-dd, alkoxy- dd, nitro or cyano, wherein the carbon atoms in these groups can be substituted with 1 to 3 halogen atoms, a 3 to 6 member ring system, saturated or partially unsaturated, which contains 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen and which is unsubstituted or substituted by any combination of 1 to 5 halogen atoms , 1 to 3 alkyl-dd groups, alkylthio-dd, alkylsulfonyl-dd, alkylsulfinyl-dd, alkoxy-dd, haloalkoxy-dd, nitro or cyano, wherein the carbon atoms in these groups may be substituted with 1 to 3 atoms of halogen, R, R4 are individually and independently hydrogen or alkyl dd, alkoxycarbonyl-dd, alkylaminocarbonyl-dd, or di (C1-C6 alkyl) -aminocarbonyl, wherein the carbon atoms in these groups can be substituted with 1 to 3 groups R #; A is C-R5 or N; B is C-R6 or N; W is C-R7 or N; with the proviso that one of A, B and W is different from N; R 5, R 6, R 7 are individually and independently hydrogen, halogen, nitro, cyano, amino, mercapto, hydroxy, C 1 -C 6 alkyl, alkenyl-d-Cio, aikinyl-d-do, cycloalkyl-dd, alkoxy- dd, alkylamino-dd, di (alkyl-d-C6) -amino, alkylthio-dd, alkylsuifonyl-dd, or alkylsulfinyl-C? -C6, wherein the carbon atoms in these groups can be substituted with 1 to 3 groups R * a system of aromatic rings of 5 to 6 members which can contain from 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which can be substituted with any combination of 1 to 5 halogen atoms, 1 to 3 alkyl-dd, haloalkyl-d-C6, alkytio-d-C6, haloalkyl-C6, alkylsulfonyl-dd, alkylsulfinyl-C? -6, haloalkylsulfonyl-d-C6, haloalkylsulfinyl-dd, alkoxy groups -C? -C6, haloalkoxy-dd, mercapto, hydroxy, amine, nitro or cyano, wherein the carbon atoms in these groups can be substituted with 1 to 3 R groups; Y is hydrogen, halogen, cyano, nitro, amino, hydroxy, mercapto, alkyl-d-C6, alkenyl-d-do, C2-C10 alkynyl, cyclo-C3-C6 cycloalky, d-alkoxy, alkylamino-d-C6, di (C 1 -C 6) alkyl amino, alkylthio-dd, C 1 -C 6 alkylsulfonyl, or C 6 C alkylsulfinyl, wherein the carbon atoms in these groups can be substituted with 1 to 3 R # groups; n is 0, 1 or 2; or the enantiomers or diastereomers, salts or esters acceptable for veterinary use thereof, to combat parasites in and on animals.
2. 2. The use according to claim 1 wherein the compounds of formula I are compounds of formula l-B wherein R7 is chloro or trifluoromethyl; R5 and Y are individually and independently chlorine or bromine; R2 is C6 alkyl, C3-C6 ayenyl, C3-C6 alkynyl, or C3-C6 cycloalkyl which may be substituted by 1 to 3 halogen atoms, or C2-C alkyl which is substituted by C4-C4 alkoxy; R31 and R32 are d-C6 alkyl or can be taken together to form cycloalkyl - which may be unsubstituted or substituted by 1 to 3 halogen atoms; R33 is hydrogen or d-d alkyl, or its enantiomers or salts acceptable from the veterinary point of view.
3. 3. The use according to claim 1 or 2 wherein the compound of formula I is a compound of formula 1-1.
4. 4. The use according to claims 1 or 2 wherein the compound of formula I is a compound of formula I-2.
5. 5. The use according to claims 1 to 4 wherein the parasites are selected from the orders of the Diptera, Siphonaptera and Ixodida.
6. 6. The use according to claims 1 to 5 wherein the animals are cats or dogs.
7. 7. A method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises administering or applying orally, topically or parenterally to animals an anti-parasite effective amount of a compound of formula I as defined in Any of claims 1 to 4. The method according to claim 7 wherein the parasites are selected from the orders of the Diptera, Siphonaptera and Ixodida. The method according to claims 7 or 8 in which the animals are cats or dogs. 10. A process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises an anti-parasite effective amount of a compound of formula I as defined in any of the claims 1 to 4. SUMMARY OF THE INVENTION The use of the compounds of formula in which Q is X1 is chlorine, bromine or fluorine; R1, R2 are individually and independently H, alkyl, alkenyl, alkynyl or cycloalkyl, alkylamino, dialkylamino, alkylcarbonylamino, alkylsulfonyl or alkylsulfinyl, wherein the carbon atoms in these groups may be substituted, or R1 and R2 may be taken together to form a ring represented by the structure p, m are 1, 2 or 3; X 'is oxygen, sulfur, amino, alkylamino, phenylamino, or methylene; Z is alkyl or phenyl; R3 is H, alkyl, alkenyl, alkynyl, cycloalkyl, wherein the carbon atoms in these groups may be substituted; R, R4 are H or alkyl, alkoxycarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl, wherein the carbon atoms in these groups may be substituted; A is C-R5 or N; B is C-R6 or N; W is C-R7 or N; with the proviso that one of A, B and W is different from N; R5, R6, R7 are H, halogen, nitro, cyano, amino, mercapto, hydroxy, alkyl, alkeniio, alkynyl, cycloalkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, or alkylsulfinyl, wherein the carbon atoms in these groups they may be substituted, a system of aromatic rings of 5 to 6 members which may contain from 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which may be substituted; Y is hydrogen, halogen, cyano, nitro, amino, hydroxy, mercapto, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, or alkylsulfinyl, where the carbon atoms in these groups may be substituted; n is 0, 1 or 2; to fight parasites in and on animals.