MXPA99012073A

MXPA99012073A - 4-haloalkyl-3- heterocyclylpyridines and 4-haloalkyl -5-heterocyclylpyridines, method for the production thereof, agents containing the same and their use as pesticides

Info

Publication number: MXPA99012073A
Application number: MXPA/A/1999/012073A
Authority: MX
Inventors: Kern Manfred; Tiebes Jorg; Sanft Ulrich; Taapken Thomas; Rook Burkhard
Original assignee: Hoechst Schering Agrevo Gmbh 13509 Berlin De
Priority date: 1997-06-16
Filing date: 1999-12-16
Publication date: 2001-12-04

Abstract

The invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyridines of general formula (I), to a method for the production thereof, to agents containing the same and to the use of said compounds to control animal pests, specially insects, mites, ectoparasites and helminths. In general formula (I), Q stands for a 5-atom heterocyclic group optionally substituted by organic radicals, Y stands for halogen-C1-C6-alkyl, X represents CH or N and m means 0 or 1.

Description

4-HALOGENOALQUIL-3-HETEROCICLILPIRIDINAS Y 4- HALOGENOALQUIL-5-HETEROCICLILPIRIMIDINAS: METHOD FOR YOUR PRODUCTION: AGENTS CONTAINING THEM AND USING THEM AS PESTICIDES The present invention relates to 4-halogenoalkyl-3-heterocyclylpyridines and to 4-halogenoalkyl-5-heterocyclyl-pyrimidines, to processes for their preparation, to compositions comprising them and to the use of 4-halogenoalkyl-3-heterocyclylpi dines and 4-halogenoalkyl-5-heterocyclylpyrimidines for controlling pests of animals, in particular insects, arachnid mites, ectoparasites and helminths. It is already known that adequately substituted pyridines or pyrimidines have acaricidal and insecticidal activity. Thus, WO 95/07891 describes pyridines which carry a cycloalkyl radical in the 4-position, which is linked by means of a heteroatom and a group of various substituents in the 3-position. WO 93/19050 describes 4-cycloalkylamino- and 4-cycloalkoxypyrimidines which carry in the 5-position, among others, the alkyl, alkoxy or haloalkoxy groups. However, the desired activity against harmful organisms is not always sufficient. Additionally, these compounds often have undesirable toxicological properties towards mammals and aquatic living beings.

Pyridyl-1, 2,4-thiazole compounds having fungicidal properties are described in DE-A 42 39 727. The compounds described therein carry the thiadiazole ring in position 2, 3 or 4 of the unsubstituted pyridine. EP-A 0 371 925 describes some 1, 3,4-oxadiazolyl- and 1, 3,4-thiadiazolylpyrimidines having nematicidal and fungicidal properties. In the biologically effective compounds described in that publication, the pyrimidine carries the oxadiazolyl or thiadiazolyl ring: a) in the 5-position, and is optionally substituted with a thiomethyl group in the 2-position; or b) in position 2 and optionally substituted in position 4 and 6, in each case, with a methyl group. Aryltriazole derivatives for use as pesticides are known from EP-0 185 256. In addition to the phenyltriazoles, which are particularly preferred, three halogenoalkyl-3-pyridyltriazoles are described: • 3- (2-chlorophenyl) -1-methyl- 5- (4-trifluoromethyl-3-pyridyl) -1 H-1, 2,4-triazole, • 3- (2,6-difluorophenyl) -1-methyl-5- (4-trifluoromethyl-3-pyridyl) -1 H-1, 2,4-triazole; and • 3- (2-chloro-4-fluorophenyl) -1-methyl-5- (4-trifluoromethyl-3-pyridyl) -1 H-1, 2,4-triazole; however, its desired activity at low application rates is not always satisfactory, especially when controlling insects and arachnid mites.

Some commercially available 4-halogenoalkyl-3-heterocyclylpyridines are known from the Maybridge 1996/1997 Maybridge catalog Chemical Co. L d., Trevillett Tintagel, Great Britain: 3- 3,5-dichlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 4-trifluoromethyl-3- pyridyl) -3-phenyl-1, 2,4-oxadiazole, 4-trifluoromethyl-3-pyridyl) -5-phenyl-1, 2,4-oxadiazole, 2-chlorophenyl) -3- (4-trifluoromethyl) -3-pyridyl) -1, 2,4-oxadiazole, 3-chlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5- 4-chlorophenyl) -3- (4 -trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5- 2-fluorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 4-fluorophenyl) - 3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 2,4-dichlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5-3 , 4-dichlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 3,5-dichlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) ) -1, 2,4-oxadiazole, • 5,6-dichloro-4-pyridyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 3,5-bistrifluoromethylphenyl) -3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole, 2-chlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 3,4-oxadiazole, 3-chlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 3,4-oxadiazole, • 2-? 4-chlorophenyl) -5- (4-thluoromethyl-3-pyridyl) -1,4,4-oxadiazole, 2-trifluoromethoxy-phenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 3,4- oxadiazole, • 2- (4-trifluoromethoxy-phenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 3,4-oxadiazole, • 2- (4-trifluoromethyl-3-pyridyl) -5-phenyl-1, 3,4-oxadiazole, • 2- (4-trifluoromethyl-3-pyridyl) - 4-methylthiazolcarbohydrazide, • ethyl 2- (4-trifluoromethyl-3-pyridyl) -4-methylthiazolecarboxylate, • N- (4-chlorophenyl) carbonyl-N '- [2- (4-trifluoromethyl-3-pihdyl) -4 -methyl-5-thiazolyl] carbonylhydrazine, • 2- (4-trifluoromethyl-3-pyridyl) -4-thiazolecarbohydrazide, • 4- (4-chlorophenyl) -2- (4-trifluoromethyl-3-pihdil) -thiazole, 4- (4-cyanophenyl) -2- (4-trifluoromethyl-3-pyridyl) -thiazole, • N- (4-trifluoromethylphenyl) carbonyl-N '- [2- (4-trifluoromethyl-3-pyridyl ) -4-thiazolyl] carbonylhydrazine, • 2- (2- (4-trifluoromethyl-3-pyridyl) thiazolyl) -5-chloro-3-methyl-benzo [b] thiophene, • 2- (4-chlorophenylmethylthio) -5- (4-trifluoromethyl-3-pyridyl) -1-methyl-1H-1, 3,4-triazole, • 2- (4-chlorophenylcarbonylmethylthio) -5- (4-trifluoromethyl-3-) pyridyl) -1-methyl-1 H-1, 3,4-triazole; and • 2-ethoxycarbonylmethylthio-5- (4-trifluoromethyl-3-pyridyl) -1-methyl-1H-1, 3,4-triazole. However, until now a biological activity against harmful organisms has not been described.

It is an object of the present invention to provide compounds having good insecticidal and acaricidal properties and, simultaneously, low toxicity towards mammals and aquatic living beings. It has now been discovered that the compounds of the formula I, optionally as salts, have a broader spectrum of activity against animal pests and, simultaneously, more favorable toxicological properties towards mammals and aquatic living beings, than the compounds of the art. previous.

In the formula (I): Y is haloalkyl of 1 to 6 carbon atoms; X is CH or N; where: a) X1 = w, X2 = NRar X3 = CR R1 0 2 a l c) X1 = v, X = CR R \ X3 - NRb 0!} x1 = v \ • X2 = CRaR2. X3 = CR &R3 0 ß) x1 2 4 5 * V, X = CR R, X3 = CR6R7 0 f) x1 - NR3, X2 = CRbR1. x3 = GVR8; Ra and Rb together are a ligature; V is oxygen, sulfur or NR9; W is oxygen or sulfur; R1 is hydrogen, alkyl of 1 to 20 carbon atoms, alkenyl of 2 to 20 carbon atoms, alkynyl of 2 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms; Cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein the last six mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, hydroxyl, -C (= W) R10, -C (= NOR10) 10, ^ NNR ^ JR10- -C. { = J0R1 °, -C (-) NR102, - OC (=) R °, -0C (=) OR10, -NR10C (= W) R10, --C (-W) NR10.NR10 [C (= W) R10], -NR10-C (= W) NRl02l -NR ^ -N ^ C? SWJR ^^ r ^ -NtC ^ JR10] ^ -N [(C =) R10] -NR1 ° 2, NR1 ° -NR10l ( C = W) Rl03r -NR1C.NRi HC = W) WR10lJ NR10 (C = NR R1 ° 2 <O-NR102J -O-NR10 { C = 'W) R10t -S02NR1 D2I -NR1 ° S02R1 °, S020R10 -OS02R1 ° -OR10 ° 2, -SR10 -SiR1 ° 3, SeR1 ° l -PRl02l -P ^ W) R102, -SOR10, -S02R1 °, * PW2R1C, 2, -PW3R1 D2 > Y aryl and heterocyclyl; the two radicals mentioned at the end are optionally substituted with one or more radicals selected from the group of: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms, halogenoalkyl of 1 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, halogenoalkynyl of 2 to 6 carbon atoms, -OR10, -NR102, -SR10, SiR103, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -SOR10, -S02R10, nitro, cyano and hydroxyl; aril; which is optionally substituted with one or more radicals of the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein these six radicals mentioned above are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -OR10, -NR102, -SR10, -SOR10, -SO2R10, halogen, cyano, nitro, -C (= W) R10, -C (= NOR10) R10, -C (= NNR102) R10 < -C (-W) OR1 °, -C (= V) NR102l -OC (=.}. R1 0. -OC { = W) OR10, -NR10C (=.}. R101 ^ N [C (= W) R10] 2 > -NR1 ° CÍ = W) OR10, -OR10, -NR102l -SR10,, 10 OR 10 -SiR, v3, -P, ?? or? 2l ^ SORl u, -S02R '\ -PW2R, 1I 0U2 * -PW3 ° 2, heterocyclyl, which is optionally substituted with one or more radicals from the group of: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms , cycloalkenyl of 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; where the last six mentioned radicals are optionally substituted with one or more radicals from the group of: cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -CÍ =) NR 02l -NR10C (= W) R1 Ü, -N [C. { -W) R10] 2I -OC (-W) R10, -OC. { = W) OR10, -OR1 °. -NR102 -SR10, -SOR10 and 10 -S02R halogen, cyano, nitro, -C (= W) R10, -C (= W) OR10, -C (= W) NR102) OC (= W) E10, -NR102, -SR10, -SOR10 and -SO2R10, -C (=) NR1 ° 2, -OC (= W) R10, -aC (= W) QR1 Ü, -NR1 ° C. { = W) R10, -N [C. { = W) R10] 2, -NR10CC-WJOR1 °, -C (= W) NR10-NR102h -C (= W) R10-WR10 [C (= W) R10] l -NR1 ° C (-W) MR102 , -NR1 ° -NR10C (=) R10, -NR1 ° -NC (= W) R102, -N (C =) R1 D .NR102, -NRia-NR10 [(C =) R10], -NR1 ° -NRl0 [(C = W) WRi], -NR1 ^ NR10 [CC = W) NR1C2], -NRlCIC = NR1 V °. -NRTO (C = NR10) NR102l -O-NR102, -ONR10. { C =) R10, -S02NR1 ° 2, -NR1 ° S? 2R10, -S02OR10. * OS02R1 C > . -SC (= W) R10, -SC. { = W) OR10, -SC (= W) R10, -PR1 Ú2l -PW2R102 | .10?.? 10 P 3R 2, S? R '3 or halogen; R2 and R3, independently of each other, have the definitions given in R1; R2 and R3 together form a 5- to 7-membered ring which may be partially or fully saturated and may be interrupted by one or more atoms of the group of nitrogen, oxygen and sulfur; without the oxygen atoms being directly adjacent to each other, and the ring optionally being substituted with one or more, but at most five, radicals R1; R4 and R6, independently of each other, have the definitions given in R1; R4 and R6 together form a 4- to 7-membered ring, which may be partially or wholly unsaturated and may be interrupted by one or more nitrogen, oxygen and sulfur group atoms; without the oxygen atoms being directly adjacent to each other, and the ring being optionally substituted with one or more, but at most five, radicals R1; R5 and R7, independently of each other, are hydrogen; alkyl of 1 to 20 carbon atoms, alkenyl of 2 to 20 carbon atoms, alkynyl of 2 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein the last six mentioned radicals are optionally substituted with one or more radicals of the group: halogen, cyano, nitro, hydroxyl, -C (= W) R10, -C (= NOR10) R10, -C. { = NNR102) R10, -C. { = W) OR10, -C. { =) NR102h - DC (= W) R10, -OC (= W.}. OR10, .NR10C (= W) R10.-NíC (= W.}. R1 ° j2, -NR1 ° C (= W) OR10 , -C { = W) NR10-NR102, -C (=) NR1 ° -NR 1 ° IC { = W) R 1 ° J, -NR1 ° -C (= W) NR 1 ° 2, -NR1 ° -NR10C (= W) R10 -NR1 Q-NlC. { = W) R10] 2f -N [(C = W) R10] -NR1 t) 2R -NR ^ -NR ^ KG-WJR10], -NR10-NR1 ° [(CW) R10], -NR10 (C = NR °) NR102l0-NR102- 'ONR10IC = W) R10 ^ GR10, ° 2, -SR10, ^ iR103. -SeR10. -PR102, .P (=) R102, -SOR10, -S02R1 °. -PW2R102, ^ PW R102r aryl and heterocyclyl; of which the last two mentioned are optionally substituted with one or more radicals of the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms, halogenoalkyl of 1 to 6 carbon atoms, halogenoalkenyl of 2 to 6 carbon atoms, halogenoalkynyl of 2 to 6 carbon atoms, halogen , -OR10, -NR10, -SiR103, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -SOR10, -SO2R10, nitro, cyano and hydroxyl; aril; which is optionally substituted with one or more radicals of the group: alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; wherein these last six mentioned radicals are optionally substituted with one or more radicals of the group: halogen, cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, C- (= W) NR102, -OR10, -NR102, -SR19, -SOR10 and -S02R10; halogen, cyano, nitro, -C (= W) R10, -C (= NOR10) R10, -C (* NNR1W2) R1W, -C (= W) ORiy -C (= W) NR1U2. -OC. { = W) Ri ?, -OC (= W) OR1 °, -NR1 ° C. { =} R10, -N [C (= W) R1] 2l -NR1) OR10, -OR10, -NR102, -SR ™ -SlR103, -PR1 ° 2. 15 10 10 10 10 -SOR, -S02R, -PW2R 2 and -PW3R 2, pyridyl, which is optionally substituted with one or more radicals from the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl from 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; where the last six mentioned radicals are optionally substituted with one or more radicals of the group: cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -OR10, -NR102, -SR10, -SOR10 and -SO2R10; halogen, cyano, nitro, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -OC (= W) R10, -OR10, -NR102, -SR10, -SOR10 and -S02R10; -C (= W) R10, -C (= NOR10) R10, -C (= NNR102) R10, -C (= W) OR10, -C (= W) NR102, or halogen; R4 and R5 together form a 4 to 7 membered ring, which may be partially unsaturated and may be interrupted by one or more atoms of the nitrogen, oxygen and sulfur group; without the oxygen atoms being directly adjacent to each other, and the ring optionally being substituted with one or more, but at most five, radicals R1; R4 and R5 together form one of the groups = O, = S or = N-R9; R6 and R7 together form a 5- to 7-membered ring, which may be partially unsaturated and may be interrupted by one or more atoms of the group of nitrogen, oxygen and sulfur; without the oxygen atoms directly adjacent to each other; and the ring being optionally substituted with one or more, but at most five, radicals R1; R6 and R7 together form one of the groups = O, = S or = N-R9; R8 is hydrogen; alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms, cycloalkenyl from 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 atoms of carbon, C2-C6-alkynyl-C3-C8-cycloalkyl, C1-C6-C3-C3-C3-C3 alkyl, C2-C6-C3-C3-C3 alkenyl 4 to 8 carbon atoms; wherein the last fourteen mentioned radicals are optionally substituted with one or more radicals from the group: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy from 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, halogenoalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkoxy of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms- alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyloxy of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyloxy of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon-cycloalkoxy atoms of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms -cycloalkenyloxy of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkenyloxy of 2 to 6 carbon atoms, carbamoyl, mono- or dialkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, mono or dicycloalkyl of 3 to 8 carbon atoms - carbamoyl, alkoxy of 1 to 6 carbon atoms - carbonyl, cycloalkoxy of 3 to 8 carbon atoms - carbonyl, alkanoyloxy of 1 to 6 carbon atoms, cycloalkanoyloxy of 3 to 8 carbon atoms, halogenoalkoxy of 1 to 6 carbon-carbon atoms, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanoid of 1 to 6 at carbon atoms, halogenalkanoid of 1 to 6 carbon atoms, alkenanid of 2 to 6 carbon atoms, cycloalkenamide of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkanamide of 1 to 4 carbon atoms, alkylthio from 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio d 2 to 6 atoms of carbon, cycloalkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylthio of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylthio of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenyl sulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, halogenoalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, halogenoalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulphinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 'atoms of carbon, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfinyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms- alkenylsulphinyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkyl C 3 -C 8 -alkylsulfinyl, C 2 -C 6 -alkinyl-cycloalkylsulfinyl alkynyl of 3 to 8 carbon atoms, C 1-6 -alkyl-cycloalkenylsulfinyl alkyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon-cycloalkenylsulfinyl atoms of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, haloalkylsulfonyl of 1 to 6 carbon atoms, haloalkenylsulfonyl from 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 atoms of carbon, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 atoms carbon-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfonyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylsulfonyl of 1 to 4 carbon atoms, alkyl from 1 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 atoms of carbon, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, haloalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms carbon, cycle alkenylamino of 4 to 8 carbon atoms, halogenocycloalkano of 3 to 8 carbon atoms, halogenocycloalkenylamino of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon-alkenylamino atoms of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylamino of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aroyloxycarbonyl, arylalkoxy from 1 to 4 carbon atoms, aryl-alkenyloxy of 2 to 4 carbon atoms, aryl-alkylthio of 1 to 4 carbon atoms, aryl-alkenylthio of 2 to 4 carbon atoms, aryl-alkylamino of 1 to 4 carbon atoms, aryl-alkenylamino of 2 to 4 carbon atoms , aryl-dialkylsilyl of 1 to 6 carbon atoms, diaryl-alkylsilyl of 1 to 6 carbon atoms, triarylsilyl and 5- or 6-membered heterocyclyl; of which, the nineteen mentioned radicals at the end are optionally substituted in their cyclic portion with one or more substituents of the group: halogen, cyano, nitro, amino, hydroxyl, thio, alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogenoalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, halogenoalkylamino of 1 to 4 carbon atoms, formyl and alkanoyl of 1 to 4 carbon atoms, aryl, which is optionally substituted with one or more radicals from the group: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, haloalkynyloxy of 2 to 6 carbon atoms carbon, cycloa lkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, carbamoyl, mono- or dialkyl of 1 to 6 carbon atoms -carbamoyl, alkoxycarbonyl of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, halogenoalkoxy of 1 to 6 carbon atoms-carbonyl, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanamide of 1 to 6 carbon atoms, halogenoalkanamide of 1 to 6 carbon atoms, alkanamide of 2 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio of 2 to 6 carbon atoms, cycloalkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halo genocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 3 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenalkenylsulfinyl of 2 to 6 carbon atoms, halogenoalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms , halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl or of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, halogenoalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino of 4 to 8 carbon atoms, halogenocycloalkyl of 3 to 8 carbon atoms, and halogenocycloalkenylamino of 4 to 8 carbon atoms ,, -C (= W) R11, OR11 or NR112; R9 is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms; wherein the last nine mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, and halogenoalkyloxy of 1 to 6 carbon atoms; R10 is hydrogen; alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkyl of 3 to 8 v alkenyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms alkynyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyl of 4 to 8 carbon atoms; where the last fourteen mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 and alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, haloalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms , halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms - alkoxy of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyloxy of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms- alque niloxy of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon-cycloalkoxy atoms of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy from 1 to 4 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkenyloxy of 2 to 6 atoms carbon, carbamoyl; mono- or dialkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dicycloalkyl of 3 to 8 carbon atoms-carbamoyl, alkoxy of 1 to 6 carbon atoms -carbonyl, cycloalkoxycarbonyl of 3 to 8 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, cycloalkanoyloxy of 3 to 8 carbon atoms, halogenoalkoxycarbonyl of 1 to 6 carbon atoms, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanoid of 1 to 6 carbon atoms, halogenalkanoid of 1 to 6 carbon atoms, alkenanid of 2 to 6 carbon atoms, cycloalkanamide of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkanamide of 1 to 4 atoms of carbon, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio from 2 to 6 carbon atoms, cycle alkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylthio of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylthio of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms -cycloalkylthio of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 5 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, haloalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms no, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkenyl of 4 at 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfinyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms , alkyl of 1 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms or, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, haloalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms - alkylsulfonyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfonyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms -alkenylsulfonyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbons ono, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfonyl of 4 at 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms , halogenoalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino of 4 to 8 carbon atoms, halogenocycloalkyl of 3 to 8 carbon atoms, halogenocycloalkenylamino of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylamino of 2 to 4 carbon atoms, cycle alkenyl of 4 to 8 carbon atoms-alkenylamino of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkinyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, aryl, aryloxy, arylthio, arylamino, arylalkoxy of 1 to 4 carbon atoms carbon, aryl-alkenyloxy of 2 to 4 carbon atoms, aryl-alkylthio of 1 to 4 carbon atoms, aryl-alkenylthio of 2 to 4 carbon atoms, aryl-alkylamino of 1 to 4 carbon atoms, aryl-alkenylamino of 2 to 4 carbon atoms, aryl-dialkylsilyl of 1 to 6 carbon atoms, diaryl-alkylsilyl of 1 to 6 carbon atoms, triarylsilyl and 5- or 6-membered heterocyclyl; where the cyclic portion of the last fourteen mentioned radicals is optionally substituted with one or more radicals from the group: halogen, cyano, nitro, amino, hydroxyl, thio, alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 4 carbon atoms , cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogenoalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, halogenalkylamino of 1 to 4 carbon atoms, formyl and alkanoyl of 1 to 4 carbon atoms, aryl, heteroaromatic of 5 or 6 members, where the last two mentioned radicals are optionally substituted with one or more radicals of the group : halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms , halogenoalkenyloxy of 2 to 6 carbon atoms, halogenoalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon, carbamoyl, mono- or dialkyl atoms of carbon-carbamoyl, alkoxycarbonyl of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl of 1 to 6 carbon atoms, halogenoalkoxycarbonyl of 1 to 6 carbon atoms, alkanamide of 1 to 6 carbon atoms, halogenoalkanamide of 1 to 6 carbon atoms, alkenanid of 2 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms , alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio of 2 to 6 carbon atoms, cycloalkylthio 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms carbon, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, haloalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 with 8 carbon atoms, halogen-cycloalkylsulfinyl with 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl with 4 to 8 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkenylsulfonyl with 2 to 6 carbon atoms, alkynylsulfonyl with 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, haloalkynylsulfonyl of 2 to 6 carbon atoms bond, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, haloalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms , cycloalkenylamino of 4 to 8 carbon atoms, halogenocycloalkanimo of 3 to 8 carbon atoms, and halogenocycloalkenylamino of 4 to 8 carbon atoms, R11 is alkyl of 1 to 10 carbon atoms, haloalkyl, aryl, which is optionally substituted with one or more radicals of the group: halogen, cyano, nitro, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, amino, monoalkylamino of 1 to 4 carbon atoms, and dialkylamino of 1 to 4 carbon atoms ,, NR102, OR10 or SR10. The term "halogen" includes fluorine, chlorine, bromine and iodine. The term "C 1 -C 4 alkyl" is to be understood as a straight or branched chain hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl radical, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tertiary butyl. Correspondingly, alkyl radicals having a larger scale of carbon atoms should be understood as straight chain or branched saturated hydrocarbon radicals containing a number of carbon atoms corresponding to the scale indicated. Thus, the term "alkyl of 1 to 6 carbon atoms" includes the alkyl radicals mentioned above and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radicals. The term "alkyl of 1 to 10 carbon atoms" is to be understood as the alkyl radicals mentioned above and, for example, the nonyl radical, 1 -decyl or 2-decyl; and the term "alkyl of 1 to 20 carbon atoms" is to be understood as the alkyl radicals mentioned above and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical. The term "halogenalkyl of 1 to 4 carbon atoms" is to be understood as an alkyl group mentioned under the term "alkyl of 1 to 4 carbon atoms" in which one or more hydrogen atoms are replaced by the same number of same or different halogen atoms, preferably fluorine or chlorine, such as trifluoromethyl, the 1-fluoroethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl group, the fluoromethyl group, the difluoromethyl group and the group 1, 1, 2, 2-tetrafluoroethyl. "C 1 -C 4 alkoxy" is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term "C 1 -C 4 alkyl". The alkoxy groups comprising a larger scale of carbon atoms must be understood accordingly. The terms "alkenyl" and "alkynyl" having an indication of the scale of carbon atoms, denote a straight or branched chain hydrocarbon radical having a number of carbon atoms corresponding to the scale indicated, which comprises minus a multiple bond, which may be in any position of the unsaturated radical in question. Thus, for example, "alkenyl of 2 to 4 carbon atoms" is the group vinyl, allyl, 2-methyl-2-propene or 2-butenyl; "C2-C6 alkenyl" denotes the radicals mentioned above and, for example, the pentenyl, 2-methylpentenyl or hexenyl group. The term "alkenyl of 2 to 20 carbon atoms" is to be understood as the radicals mentioned above and, for example, the 2-decenyl or 2-eicosenyl group. "Alkynyl of 2 to 4 carbon atoms", for example, is the ethynyl, propargyl, 2-methyl-2-propynyl or 2-butynyl group. "Alkenyl of 2 to 6 carbon atoms" is to be understood as the radicals mentioned above and, for example, the 2-pentynyl or 2-hexynyl group. "Alkenyl of 2 to 20 carbon atoms" is to be understood as the radicals mentioned above and, for example, the 2-octinyl or 2-decinyl group. "Cycloalkyl of 3 to 8 carbon atoms" denotes moikanocyclic alkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radicals; and bicyclic alkyl radicals, such as the norbornyl radical. The term "C 3 -C 8 cycloalkyl-C 1 -C 4 alkyl" is to be understood, for example, as the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical; and the term "alkyl of 1 to 5 carbon atoms-cycloalkyl of 3 to 8 carbon atoms" is to be understood, for example, as the radical 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-terbutyl -cyclohexyl.

"Alkoxy of 1 to 4 carbon atoms-alkyloxy of 1 to 6 carbon atoms" is an alkoxy group as defined above, which is substituted with another alkoxy group, such as, for example, 1-ethoxyethoxy. "Cycloalkoxy of 3 to 8 carbon atoms" or "cycloalkylthio of 3 to 8 carbon atoms" should be interpreted as one of the cycloalkyl radicals of 3 to 8 carbon atoms, mentioned above, which is linked by an oxygen atom or a sulfur atom. "Cycloalkyl of 3 to 8 carbon atoms-alkoxy of 1 to 6 carbon atoms" is, for example, the group cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexyletoxy or the cyclohexylbutoxy group. The term "alkyl of 1 to 4 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms" is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or butylcyclohexyloxy group. "Alkylthio of 1 to 6 carbon atoms" is an alkylthio group whose hydrocarbon radical has the meaning given under the term "alkyl of 1 to 6 carbon atoms". Correspondingly, the term "C 1 -C 6 alkylsulfinyl" is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulphinyl group, and "alkylsulfonyl-1" 6 carbon atoms "is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group. "Alkylamino of 1 to 6 carbon atoms" is a nitrogen atom that is substituted with one or two identical or different alkyl radicals, from the definition given above.

The term "mono- or dialkylcarbamoyl of 1 to 6 carbon atoms" is a carbamoyl group having one or two hydrocarbon radicals having the meaning given under the term "alkyl of 1 to 6 carbon atoms" and which, in the case of two hydrocarbon radicals can be identical or different. Correspondingly, the term "dihaloalkyl carbamoyl of 1 to 6 carbon atoms" is a carbamoyl group bearing two haloalkyl radicals of 1 to 6 carbon atoms, according to the above definition, or a halogenoalkyl radical of 1 to 6 atoms of carbon and an alkyl radical of 1 to 6 carbon atoms, according to the definition given above. "Alkanoyl of 1 to 6 carbon atoms", for example, is the acetyl, propionyl, butyryl or 2-methylbutyryl group. The term "aryl" is to be understood as an isocitic aromatic radical, preferably having from 6 to 14, in particular from 6 to 12, carbon atoms; such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. "Aroyl", in such a manner, is an aryl radical as defined above, which is linked by a carbonyl group, such as, for example, the benzoyl group. The term "heterocyclic" denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated, and which may be interrupted by at least one or more identical atoms, from the group: nitrogen, sulfur or oxygen; however, the oxygen atoms are not directly adjacent to each other, and at least one carbon atom is present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole radical, isoxazole, pyrazole, 1,4-oxadiazole, 1,4-thiadiazole, 1,4-triazole, 1,4-oxadiazole, 1,4-thiadiazole, 1,4- triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1, 3,5-triazine, 1, 2,4-triazine, 1, 2,4, 5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1, u-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine, piperidine , pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyra no, isoxazolidine, or thiadiazole. The term "heteroaromatic" thus comprises, from among the meanings mentioned above under "heterocyclyl" in each case, the fully unsaturated aromatic heterocyclic compounds. "Aryl-C 1 -C 4 -alkoxy" is an aryl radical that is attached via an alkoxy group of 1 to 4 carbon atoms, for example, the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical. "Arylthio" is an aryl radical linked by means of a sulfur atom, for example, the phenylthio radical or the 1- or 2-naphthylthio radical. Correspondingly, "aryloxy" is, for example, the phenoxy radical or 1- or 2-naphthyloxy.

"Aryl-alkylthio of 1 to 4 carbon atoms" is an aryl radical which is linked by an alkylthio radical, for example, the benzylthio, naphthylmethylthio or phenylethylthio radical. The term "trialkylsilyl of 1 to 6 carbon atoms" denotes a silicon atom carrying three identical or different alkyl radicals, according to the above definition. Correspondingly, "aryl-dialkylsilyl of 1 to 6 carbon atoms" is a silicon atom bearing an aryl radical and two identical or different radicals, according to the above definition. "Diaryl-alkylsilyl of 1 to 6 carbon atoms" is a silicon atom carrying an alkyl radical and two identical or different aryl radicals, according to the above definition; and "triarylsilyl" is a silicon atom carrying three identical or different aryl radicals, according to the above definition. In cases where two or more radicals R10 are present in a substituent, such as, for example, in -C (= W) NR 02, these radicals can be identical or different. Preference is given to those compounds of formula I in which: Y is alkyl of 1 to 6 carbon atoms, which is mono- or polysubstituted with chlorine and / or fluorine; m is zero; Q is a heterocyclic group of 5 members: where: a) X2 = NRa and X3 = CRbR1; or b) X2 = CRaR2 and X3 = CRbR3; or c) X2 = CR4R5 and X3 = CR6R7; Ra and Rb together are a ligature; R1, R2, R3, R4 and R6, independently of one another, are hydrogen, halogen, alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, where the last four mentioned hydrocarbon radicals are optionally mono- or polysubstituted with identical or different radicals, of a group A1 consisting of: alkyl of 1 to 6 carbon atoms-carbonyl, alkylamino of 1 to 6 carbon-carbonyl atoms, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkylcarbonylamino of 1 to 6 carbon atoms, alkylsulfonylamino of 1 to 6 carbon atoms carbon, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino; wherein the first eleven mentioned radicals of the group A1 are optionally mono- or polysubstituted, each having identical or different radicals, of a group B 1 consisting of halogen, cyano, alkoxy of 1 to 3 carbon atoms, and phenyl, which is mono - or optionally polysubstituted with one or more halogen atoms, and where the last three mentioned radicals of group A1 are each, optionally mono- or polysubstituted with identical or different radicals of a group B2 consisting of H, halogen, cyano, nitro, alkyl of 1 to 3 carbon atoms, and alkoxy of 1 to 3 carbon atoms, or are alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, phenyl, pyridyl, furyl, thienyl, pyrrhyl, where the last eight mentioned radicals are optionally mono- or polysubstituted with identical or different radicals from group B1, or are OR10, SR10 or N (R10) 2; each of R5 and R7, independently of each other, is hydrogen, halogen, alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 atoms of carbon, wherein the last four mentioned hydrocarbon radicals are mono- or polysubstituted optionally with identical or different radicals, of a group A2 consisting of alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, alkoxy 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkylcarbonylamino of 1 to 6 carbon atoms, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino; where the first ten mentioned radicals of group A2 are optionally mono- or polysubstituted, each having identical or different radicals of group B1, and the last three mentioned radicals of group A2 are each optionally mono- or polysubstituted with identical or different radicals of group B2; or are alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, phenyl, pyridyl, furyl, thienyl, pyrryl, where the last eight radicals mentioned are optionally mono- or polysubstituted with identical or different radicals of group B1, or are OR10, SR10 or N (R10) 2; R10 is hydrogen, benzyl, alkyl of 1 to 6 carbon atoms, cycloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, alkylcarbonyl of 1 to 6 carbon atoms, or alkylsulfonyl of 1 to 6 carbon atoms, where the last eight radicals mentioned are mono- or polysubstituted optionally with identical or different halogen atoms; Particular preference is given to the compounds of the formula I in which: Y is trifluoromethyl; R1, R2, R3, R4 and R6 are each independently, halogen, alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms, where the last two mentioned radicals are mono- or polysubstituted optionally with identical or different radicals of the group A3, consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, alkylsulfonylamino of 1 to 4 carbon atoms, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; where the first eleven radicals mentioned in group A3 are each optionally mono- or polysubstituted with identical or different radicals of group B1, and the last three mentioned radicals of group A3 are each optionally mono- or polysubstituted with identical or different radicals from the group B2 or are OR10, SR10 or N (R10) 2; each of R 5 and R 7, independently of the other, is halogen, alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms, where the last two mentioned radicals are optionally mono- or polysubstituted with identical or different radicals of an A4 group consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms , alkylcarbonylamino of 1 to 4 carbon atoms, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; wherein the first ten radicals mentioned in group A4 are optionally mono- or polysubstituted, each with identical or different radicals of group B1; and the last three mentioned radicals of group A4 are optionally mono- or polysubstituted with identical or different radicals of group B2, or are OR10, SR10 or N (R10) 2; R10 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, alkylcarbonyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms carbon, where the last six mentioned radicals are mono- or polysubstituted optionally with identical or different halogen atoms.

Particular preference is given to the compounds of the formula I in which: each of R1, R2, R3, R4 and R6, independently of the others, is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 atoms carbon, where the last two mentioned radicals are mono- or polysubstituted optionally with radicals identical or different from a group A5 consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, alkylsulfonylamino of 1 to 4 carbon atoms, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; where the first eight mentioned radicals of group A5 are optionally mono- or polysubstituted, each with identical or different radicals of group B1 and the last three mentioned radicals of group A5 are optionally mono- or polysubstituted, each with identical or identical radicals different from group B2; each of R5 and R7, independently of the other, is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, where the last two mentioned radicals are mono- or polysubstituted optionally with identical or different radicals from a group A6 consisting of: alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; wherein the first seven mentioned radicals of group A6 are optionally mono- or polysubstituted, each with identical or different radicals of group B1, and the last three mentioned radicals of group A6 are optionally mono- or polysubstituted, each with radicals identical or different from group B2. Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl and other groups that induce acidic properties, those compounds can be reacted with bases to give salts. Suitable bases are, for example, the hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium; in addition, ammonia, primary, secondary and tertiary amines, having alkyl radicals of 1 to 4 carbon atoms, and also the mono-, di- and trialkanolamines of alkanols of 1 to 4 carbon atoms. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino and other groups that induce basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid; organic acids, such as acetic acid, oxalic acid; and acid salts, such as NaHS0 and KHS0. The salts that can be obtained in this way also have the insecticidal, acaricidal and nematicidal properties. The compounds of the formula I may have one or more asymmetric carbon atoms or stereoisomers in the double bonds. Therefore, enantiomers or diastereomers may be present. The invention comprises both the pure isomers and their mixtures. The mixtures of diastereomers can be separated to the isomers, by the usual methods, for example, by selective crystallization in suitable solvents, or by means of chromatography. The racemates can be separated from the enantiomers by the usual methods. The present invention also provides processes for preparing compounds of the formula I: To prepare compounds of the formula (I) in which: a). X1 = W, X2 = NRa, X3 = CRbR1 and Ra, Rb and R1 are as defined above, and W is oxygen; activated derivatives of the acid of the formula (II) are reacted: where X and Y are as defined previously, in the presence of a base, with a compound of the formula (III): wherein the radical R1 is as defined in formula (I). Suitable activated derivatives are, for example, acyl halides, esters and anhydrides. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine; the alkali metal hydroxides, the alkali metal alkoxides, such as sodium ethoxide or potassium terbutoxide, or the alkyl metal compounds, such as butyl lithium. Depending on the conditions, the reaction described above may be carried out as a one-step process or as a two-step procedure, by means of the intermediates of the formula The compounds of the formula (IV) can be cyclized to 1,2,4-oxadiazoles by heating in an inert solvent at temperatures up to 180 ° C. The compounds of the formula (IV) can also be obtained directly from the acid of the formula (II) and amidoximes of the formula (III), using a dehydrating reagent, such as dicyclohexyl-carbodiimide, 1-ethyl-3- (3 -dimethylaminopropyl) carbodiimide or N, N'-carbonyldiimidazole. Both the acids of the formula (II) and the amidoximes of the formula (III) are commercially available or can be prepared by methods known in the literature (see, for example, Houben-Weyl, Methoden der organischen Chemie, Volume X). / 4, pages 209-212; EP-A 0 580374; GF Hollan, JN Pereira, J. Med. Chem., 1967, 10, 149). In case a) mentioned above, where W is sulfur, the compounds of the formula (I) can be obtained in a manner known in the literature, by reacting a compound of the formula (VII) with an electrophilic amination reagent , such as hydroxylamino-O-sulfonic acid (Y. Lin, SA Lang, SR Petty, J. Org. Chem., 1980, 45, 3759).

(VII) (i) The compounds of the formula (VII), which are necessary as starting materials for this reaction, can be prepared by reacting the thioamides of the formula (VIII) with dialkylamide-dialkylacetals of the formula (IX), where R1 is as defined above. and each of R12 and R 13 is alkyl of 1 to 4 carbon atoms.

(VIII) (IX) (VII) To prepare the compounds of the formula (I) in which: b). X1 = NRa, X2 = CRbR1, X3 = W; and Ra, Rb and R1 are as defined above, and W is oxygen, amidoximes of the formula (V) can be reacted with activated derivatives of the acids of the formula (VI), or with the acids themselves of the formula (VI).

(V) (V I) (I) To prepare compounds of the formula (I) in which: c). X1 = V, X2 = CRaR1, X3 = NRb and Ra, Rb and R1 are as defined above and V is sulfur, N, N'-diacylhydrazines of the formula (XIII) can be cyclized with a thiolation reagent, such as a reagent from Lawesson (AA El-Barbary, S. Scheibyl, SO Lawesson, H. Fritz, Acta Chem. Scand., 1980, 597), in an inert solvent, such as toluene.

(XIII) (I) In the aforementioned case b), when W is oxygen, the compounds of the formula (I) can be prepared by reacting the acids of the formula (II) with hydrazines of the formula (X), where R1 is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride. (l l) (X) (l) It is also possible to react acid hydrazides of the formula (XI) with ortho-esters of the formula (XII), in which R1 is as defined above and R12 is alkyl of 1 to 4 carbon atoms.

(X I) (X I I) (l) The reaction can be carried out with or without solvent and with or without an activating reagent. Suitable solvents are hydrocarbons, such as toluene, or ethers, such as 1,2-dimethoxyethane. A suitable activating reagent, for example, is phosphorus oxychloride. The temperature of the reaction is generally the reflux temperature of the solvent. To prepare the compounds of the formula (I) in which: d). X1 = v, x2 = CRaR2, X3 = CRbR3; and Ra, Rb and R3 are as defined hereinabove, and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

(X I V) (I) Suitable dehydrating reagents are inorganic acyl chlorides, such as phosphorus oxychloride or thionyl chloride; inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methoden der organischen Chemie, volume E8a, pages 935-941). The reaction can be carried out with or without a solvent. Suitable solvents are inert solvents, such as toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. Advantageously, the reaction temperature is on a scale between 50 ° C and 150 ° C. The compounds of the formula (XIV) can be obtained, for example, by oxidation of the corresponding hydroxyl compound of the formula (XV), being possible to use all the reagents that are usually used for this purpose in organic chemistry (Milos Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington, DC, USA, 1990).

(XV) (XIV) In the aforementioned case, when V is sulfur, the compounds of the formula (I) can be prepared by condensation of the thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), where Z is halogen, particular chlorine or bromine; acyloxy or sulfonyloxy, and (XVII) (XVIII) (i) To prepare the compounds of the formula (I) in which: e). X1 = V, X2 = CR4R5, X3 = CR6R7; and R4, R5, R6 and R7 are as defined above and V is oxygen, the compounds of the formula (XV) are reacted with cyclization reagents, such as the Burgess reagent (GM Atkins, EM Burgess, J. Am. Chem. Soc, 1968, 90, 4744), in a solvent such as tetrahydrofuran and 1,4-dioxane, at a temperature that is on a scale from room temperature to the reflux temperature of the solvent.

(XV) (i) The compounds of the formula (XV) can be obtained by reacting the activated derivatives of the acid in the formula (II) with beta-aminoalcohols of the formula (XVI), if appropriate, in the presence of a base such as, for example, triethylamine , in an inert solvent, such as, for example, dichloromethane.

(X V I) An acyl halide or an anhydride can be used as an activated derivative of the acid. Numerous beta-aminoalcohols of the formula (XVI) are commercially available. For others, there are a large number of preparation procedures in the literature; for example, a re-recruitment of alpha-amino acids (B.M. Trost Comprehensive Organic Synthesis, Reduction, volume 8, Pergamon Press, Oxford, England, 1991). In the aforementioned case, case e), when V is sulfur, the compounds of the formula (I) can be prepared by reaction of the thioamides of the formula (XVII) with compounds of the formula (XIX); the two substituents Z being as defined above, and identical or different (A. R. Katritzky, Comprehensive Heterocyclic Chemistry, volume 6, pages 306-312, Pergamon Press, Oxford, England). (x v i i) (x ix) (i) The thioamides of the formula (XVII) can be obtained commercially or can be prepared by the addition of hydrogen sulphide to the corresponding carbonitriles, in the presence of a base. (A. S. Fairfull, J. L. Lowe, D. A. Peak, J. Chem. Soc, 1952, 742). To prepare compounds of the formula (I) in which: f). X1 = NRa; X2 = CRbR1; X3 = NR8; and Ra, Rb, R1 and R8 are as defined above, hydrazides of the formula (XX) are reacted: (X X) with a compound of the formula (XXI) or with thioamides of the formula (XXII).

(Houben-Weyl, Methoden der organischen Chemie, volume E8d, pages 510-512).

(X X I) (X X I I) This reaction can be carried out with or without the use of solvent; alcohols being suitable solvents, such as ethanol and propanol, or aromatic hydrocarbons, such as toluene and xylene. If the reaction is carried out in a solvent, the advantageously selected reaction temperature is the reflux temperature of the solvent. On the other hand, if the reaction is carried out without solvent, it is possible to heat up to 200 ° C, if appropriate. Once the group Q has been assembled, for example, by means of condensation, cyclization or cycloaddition reactions, the radicals R1 to R9 can be derived, if desired, using the arsenal of organochemical synthesis methods.

To assemble the compounds of the formula (I), in which m is 1, the compounds of the formula (I) in which m is 0 can be treated with an oxidizing agent, such as, for example, chloroperbenzoic The compounds of the formula (I) (hereinafter also referred to as "the active compounds") have good tolerance for the plants, favorable homothermal toxicity and advantageous properties with respect to aquatic organisms; and are suitable for controlling pests, in particular insects, arachnids (acarids), helminths and molluscs, especially, preferably, to control insects and arachnids found in agriculture, in animal husbandry, in forests, in the storage of stored products. and stored materials, and in the hygienic sector. They are active against normally sensitive and resistant species, and all stages or individual stages of development. The pests mentioned above include: From the order of the acarids, for example: Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp. From the order of the isopods, for example: Oniscus asselus, Armadium vulgaris and Procellio scaber. From the order of the diplópodos, for example: Blaniulus guttulatus.

From the order of the chilopoda, for example, Geophilus carpophagus and Scultigera spp. From the order of the symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of springtails, for example, Onychiurus armatus. From the order of the Orthoptera, for example: Blatta orientalis, Periplaneta americanam, Leucophaea madeirae, Germanic Blattella, Acheta domesticus, Gryllotalpa spp, Locusta migratory migratory, Melanoplus dlfferentialis and Schistocerca gregaria. From the order of the Isoptera, for example: Reticulitermes spp. From the order of the anophores, for example: Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. And Linognathus spp. From the order of the malophagous, for example: Trichodectes spp. and Damalinea spp. From the order of the Thysanoptera, for example: Hercinothrips femoralis, Thrips tabaci and Frankliniella spp. From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp. From the order of the Homoptera, for example: Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporarium, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp, Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticepts, Lecanium corni, Saissetia oleae, Laodelphax stritellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Paseudococcus spp. and Psylla spp. From the order of the Lepidoptera, for example: Pectinophora gossypiella, Bupalus piniarius, Cheimotobia brumata, Lithocolletis blancardella, Hyponemeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrostis spp., Euxoa spp. , Feltia spp., Earias insulana, Heliothis spp., The hygma exigua, Mamestra brasicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumirerana, Clysis ambiguella, Homona magnanimous, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp. From the order of coleoptera, for example: Anobium punctatum, Thisopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochieariae, Diabrotica spp., Psylloides chrusocephala, Epilachna varivestis, Atomaria spp., Aryzaephilus surinamensis, Anthonumus app., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Atagenus spp., Lyctys spp., Meligether aeneus, Ptinus spp., Niptus hololeucus, Gibbium pshylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp. From the order of Hymenoptera, for example: Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. From the order of Diptera, for example: Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp. Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrusomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit. , Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Typula paludosa. From the order of the siphonaptera, for example: Xenopsylla cheopsis and Ceratophyllus spp. From the order of arachnids, for example: Scorpio maurus and Latrodectus mactans. From the class of helminths, for example: Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strogyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Hetarakis, as well as Fasciola. From the class of gastropods, for example: Deroceras spp., Arion spp., Lymmaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., And Oncomelania spp.

From the class of bivalves, for example, Dreissena spp. The phytoparasitic nematodes that can be controlled according to the invention include, for example, soil nematodes, root parasites, such as, for example, those of the meloidoginous genera (nematode root nodules, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanicá); Heteros and globoderos (nematode formers of cysts, such as Globodera rostochiensis, Globodera paluda and Heterodera trifolii); and of the radofol genera (such as Radopholus similis), pratilencos (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus); tillencula (such as Tylenchulus semipenetrans), tilencorincos (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), rotilencos (such as Rotylencus robustus), heliocotilencos (as Heliocotylenchus multicinctus), belonoaimos (like Belonoaimus longicaudatus), longidores (like Longidorus elongatus), tricodoros (like Trichodorus primitivus) and xifinemos (like Xiphinema index). Additionally, the nematodes of the genera dithilencos (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), afelencoides can be controlled with the compounds according to the invention. (leaf nematodes, such as Aphelenchoides ritzemabosí) and angina (flower nematodes, such as Anguina tritici). This invention also relates to compositions, in particular to insecticidal and acaricidal compositions, which comprise the compounds of the formula (I) in addition to suitable formulation aids.

The compositions according to the invention comprise, in general, the active compounds of the formula (I) in an amount of 1 to 95% by weight. They can be formulated in different ways, depending on how determined by the biological and / or chemical-physical parameters. Therefore, the suitable formulation possibilities are: Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, spray solutions, dispersions based on oil or water; suspension concentrates (SC), suspension emulsions (suspoemulsions) (SE); sprinkling powders (DP), coatings for seeds, granules, in the form of microgranules, sprayed granules, absorption granules and adsorption granules; water dispersible granules (WG), ULV formulations, microcapsules, waxes or baits. These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchier, Chemische Technologie (Chemical Technology), Volume 7, C. Hauser Verlag Munich, Germany, 4a. edition, 1986; van Falkenberg, Pesticides Formulations, Marcel Dekker, NY, E. U. A., 2a. edition, 1972-73; K. Martens Spray Drying Handbook, 3a. 1979 edition, G. Goodwin Ltd., London, England. The necessary formulation aids, ie, carrier substances and surfactants, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2a. edition, Darland Books, Caldwell, NJ, E. U. A.; H. v. Olphen, Introduction to Clay Colloid Chemistry, 2a. edition, J. Wiley & Sons, NY, E. U. A., Marsden, Solvents Guide, 2a. edition, Interscience, NY, E. U. A., 1950; McCutcheon's, Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood, NJ, E. U. A .; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., NY, E. U. A. 1964; Schonfeldt, Grenzfláchenaktive Áthylenoxidaddukte (Surface-active ethylene oxide adducts), Wiss. Verlagsgesell., Stuttgart, Germany, 1967; Winnacker-Küchier, Chemische Technologie (Chemical Technology), volume 7, O Hauser Verlag, Munich, Germany, 4a. edition, 1986. It is possible to prepare combinations with other substances that have a pesticidal action, fertilizers and / or development regulators, on the basis of these formulations; for example, in the form of a ready-to-use formulation, or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, together with the active compound and in addition to a diluent or an inert substance, also absorb wetting agenes, for example, polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkylphenol or alkylphenol sulfonates. , and dispersing agents, for example: sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example: butanol, cyclohexanone, dimethylformamide, xylene or else aromatics or high-boiling hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers that can be used are, for example: calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; or non-ionic emulsifiers, such as polyglycol fatty acid esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters. Dusts are obtained by dusting the active compound with finely divided solid substances, for example, talc, clays that occur in nature, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Granules can be prepared, either by spraying the active compound on an inert granulated material, capable of adsorption, or by applying concentrates of the active compound to the surface of carrier substances, such as sand, kaolinites, or inert granular material, by means of adhesives, example: polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the usual manner for the preparation of fertilizer granules, if desired, as a mixture with the fertilizers. In wettable powders generally the concentration of active compound is generally around 10 to 90% by weight, the rest being up to 100% by weight, usual constituents of formulation. In emulsifiable concentrates the concentration of active compound may be about 5 to 80% by weight. Dust-like formulations usually comprise from 5 to 20% by weight of active compound and the spray solutions, from about 2 to 20% by weight. In the granules the content of active compound depends partially on whether the active compound is present in liquid or solid form, and which granulation aids, fillers and the like are being used. Additionally, the aforementioned active compound formulations comprise, if appropriate, customary thickeners, wetting agents, dispersing agents, emulsifiers, penetrating agents, solvents, fillers or carriers. For use, the concentrates in the form obtained in commerce, are diluted in the usual manner, if appropriate, for example, by means of water, in the case of wettable powders, emulsifiable concentrates, dispersions and, in some cases, also the microgranules. The powder-like or granulated formulations, as well as the spray solutions are usually not further diluted with additional inert substances, before use. The required amount applied varies with external conditions, such as temperature, humidity and the like. It can vary within wide limits; for example, between 0.0005 and 10.0 kg / ha or more of active substance; but preferably between 0.001 and 5 kg / ha. The active compounds of the invention may be present in their formulations as are commercially available, and in the forms of use prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides. , nematicides, fungicides, growth regulating substances or herbicides. Pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like. The agents participating in the mixtures are: 1.- From the group of phosphorus compounds: acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, demeton, demeton-S- methyl, demeton-S-methyl sulfone, dialiphos, diazinon, dichlorvos, dicrotophos, phosphorothioate of OO-1, 2,2,2-tetrachloroethyl (SD 208 304) dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos , fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, pehtroate, phorate , phosalone, phospholan, phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimmiphos-methil, profenofos, propaphos, proetamphos, prothiophos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetrachlorvinpho s, thiometon, triazophos, trichlorphon, vamidothion; 2. - from the group of carbamates: aldicarb, 2-sec-butylphenyl-methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiophencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenyl-butyryl (methyl) carbamate, oxamyl, pyrimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate ( OK 135), 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717); 3.- group of carboxylic acid esters: allethrin, alphametrin, (E) - (1 R) -cis-2 > 2-dimethyl-3- (2-oxothiolan-3-ylidemethyl) cyclopropanecarboxylate 5-benzyl-3-furylmethyl, bioallethrin, bioallethrin (isomer (S) -cyclopentyl), bioresmethrin, biphenate, (1 RS) -trans-3- (4-tert-butylphenyl) -2,2-dimethylcyclopropanecarboxylate of (RS) -1-cyano-1- (6-phenoxy-2-pyridyl) methyl (NCI 85193), cycloprothrin, cyhalotrhrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin , esfenvalerate, fenfluthrin, fenpropatrhrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin (isomer (R)), d-pralethrin, pyrethrins (products that occur in nature), resmethrin, tefluthrin, tetramethrin and tralomethrin; 4.- from the group of amidines: amitraz, chlordimeform; 5.- of the group of tin compounds: cyhexatin, fenbutatin oxide; 6.- Others: abamectin, Bacillus thuringiensis, benzultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron 2- (4-chlorophenyl) -4,5-diphenylthiophene (UBI-T 930), chlorfentezine, cypropropanecarboxylate 2 -naphthylmethyl (Ro 12-0470), cyromazine, N- (3,5-dichloro-4- (1,1-, 2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl) ethyl ester - 2-chloro-benzocarboximide; dicofol, N- (N- (3,5-dichloro-4- (1,1,1,2-tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron, N- (2,3 -dihydro-3-methyl-1, 3-thiazol-2-ylidene) -2,4-xylidene, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl) (dimethyl) (3- (3-phenoxyphenyl) propyl) -silane, (4-ethoxyphenyl) (3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane, phenoxycarb, ether 2-fluoro-5- (4- (4-ethoxyphenyl) -4-methyl-1- pentyl) diphenylic (MTI 800), granulosis and nuclear polyhedrosis virus, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl-3,4-dihydro- 6H-thiazine (DZ 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazoline-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid. The compounds participating in the combination, mentioned above, are known active compounds and most of them are described in Ch. R. Worthing, S.B. Walker, The Pesticide Manual, 7a. edition (1983), British Crop Protection Council. The content of active compound of the forms of use prepared from the formulations that can be obtained in commerce can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The active compounds are used in a customary manner, suitable for the forms of use. The active compounds according to the invention are also suitable for controlling endoparasites and ectoparasites in the field of veterinary medicine and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form, for example, of tablets, capsules, potions or granules, by means of dermal use in the form, for example, of dips, sprays, compounds for pouring, for spraying and sprinkling, and by parenteral use, for example, in the form of injection. The novel compounds of the formula (I), consequently, can also be advantageously used in the raising of cattle (for example, cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention compounds are orally administered to animals, if appropriate in suitable formulations (see above) and, if appropriate, with drinking water or food. Since the excretion in the feces takes place in an active way, the development of insects in the feces of the animals can very easily be prevented in that way. The doses and formulations suitable in each case depend in particular on the species and the stage of development of the livestock animals, and also on the infestation pressure, and can be determined easily and specifically by means of of usual methods. Novel compounds can be used in cattle, for example, in doses of 0.01 to 1 mg / kg of body weight. In addition to the methods of application mentioned above, the active compounds of the formula I according to the invention also have excellent systemic action. Therefore, the active compounds can be introduced into plants through the parts of the plant that are below the ground and above the ground (root, stem, leaves), when the active compounds are applied in liquid or solid form to the vicinity of the plants (for example, granules in application to the land, application in flooded rice fields). Additionally, the active compounds according to the invention are useful in particular for treating vegetative and generative propagation material, such as, for example, seeds, for example, of cereals, vegetables, cotton, rice, beet and other crops.; and of ornamental, of bulbs, cuts and tubers of other crops and ornamental propagated vegetatively. For this purpose, pre-planting or planting treatment can be carried out (for example, by special seed coating techniques, by impregnations for seed in liquid or solid form, or by treatment in seed box), during sowing or planting. planting, or after sowing or planting by special application techniques (for example, treatment in row of sowing). Depending on the application, the amount of active compound applied may vary within a relatively broad range. In general, the application regimes are between 1 g and 10 kg of active compound per hectare of the land surface. The examples that follow serve to illustrate the invention.

A.- EXAMPLES OF FORMULATION a) .- A powder for dusting is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as an inert substance, and crushing the mixture in an impact mill. b) .- A wettable powder is obtained which is easily dispersible in water, mixing 25 parts by weight of active compound, 65 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight. weight of sodium oleoylmethyltauride, as a wetting and dispersing agent, and grinding the mixture in a disk mill with peaks. c) .- A dispersion concentrate is prepared which can be easily dispersed in water, by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight d water, and grinding the mixture to a fineness of less than 5 microns, in a grinding bead mill. d) .- An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as a solvent, and 10 parts by weight of ethoxylated nonylphenol (10 OE), as an emulsifier. e) .- Granules of 2 to 15 parts by weight of active compound and an integumentary granule carrier material, such as attapulgite, pumice granules and / or quartz aena, can be prepared. A suspension of the wettable powder of example b) having a solids content of 30% is favorably used, and this is sprayed onto the surface of attapulgite granules and the components are dried and intimately mixed. The content by weight of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

B.- CHEMICAL EXAMPLES EXAMPLE No. 1 3-isopropyl-5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole (Table 1, No. 81) 2 g of methyl 4-trifluoromethylnicothi-nate were initially charged and 1. 56 g of isobutyramide oxime in 15 ml of ethanol and cooled to 0 ° C. 10 ml of a 1.2 molar solution of sodium ethoxide was added dropwise to that solution. The mixture was allowed to warm to room temperature over a period of two hours, and then stirring was continued at that temperature until the reaction was finished, according to thin layer chromatography (TLC). The reaction mixture was concentrated and the residue was sonicated in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. 1 H NMR (CDCl 3, 300 MHz): d = 1.41 (d, J = 6.9 Hz, 6H), 3.22 (m, 1 H), 7.78 (d, J = 5 Hz, 1 H), 9.02 (d, J) = 5 Hz, 1 H), 9.34 (s, 1 H) ppm.

EXAMPLE No. 2 3-isopropyl-5- (4-trifluoromethyl-5-pyrimidyl) -1, 2,4-oxadiazole (Table 1 No. 189) Initially, 2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were charged in 15 ml of ethanol and cooled to 0 ° C. 10 ml of a 1.2 molar solution of sodium ethoxide was added dropwise to this solution. The mixture was allowed to warm to room temperature for one hour and then heated to reflux until the reaction had ended according to TLC. The reaction mixture was concentrated and the residue was taken up in a saturated solution of ammonium chloride and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. 1 H-NMR (CDCl 3, 300 MHz): d = 1.43 (d, J = 7 Hz, 6 H), 3.22 (hept., J = 7 Hz, 1 H), 9.52 (s, 1 H), 9.58 (s, 1 H) ppm.

EXAMPLE No. 3 2-Methyl-5- (4-trifluoromethyl-3-pyridyl) -1,3,4-oxadiazole (Table 3, No. 549) 500 mg of 4-trifluoromethylnicotinic acid hydrazide in 3.5 ml of triethyl octoacetate was heated at reflux for two hours. Subsequently, the reaction mixture was concentrated and the residue was carefully mixed with 2 ml of phosphorus oxychloride. The mixture was stirred at room temperature for one hour, then poured onto ice and extracted with ethyl acetate. Chromatographic purification of the crude product obtained after drying and concentrating gave the desired compound as a yellowish oil. 1 H NMR (CDCl 3, 300 MHz): d = 2.67 (s, 3H); 7.75 (d, J = 5 Hz, 1 H), 8.99 (d, J = 5 Hz, 1 H), 9.34 (s, 1 H) ppm.

EXAMPLE No. 4 4- (Ethoxycarbonylmethyl) -2- (4-trifluoromethyl-3-pyridyl) thiazole (Table 4. No. 688) 500 mg of 4-trifluoromethylpyridin-3-thiocarboxyamide was dissolved and 440 mg of ethyl 4-chloroacetate in 5 ml of dimethylformamide, and heated at 100 ° C for four hours. After cooling, the reaction mixture was poured into ice water and extracted with diethyl ether. The diethyl ether phase was dried over magnesium sulfate, filtered and concentrated, and the residue was purified by chromatography. This gave the desired product in pure form, as a colorless oil. 1 H-NMR (CDCl 3, 300 MHz): d = 1.28 (t, J = 7.5 Hz, 3 H), 3.92 (s, 2 H), 4.22 (c, J = 7.5 Hz, 2 H), 7.43 (s, 1 H) , 7.68 (d, J = 5 Hz, 1 H), 8.86 (d, J = 5 Hz, 1 H), 8.97 (s, 1 H), ppm.

EXAMPLE No. 5 4-Ethyl-2- (4-trifluoromethyl-3-pyridyl, oxazole (Table 4. No. 762) 2.6 g of 4-trifluoromethylnicotinic acid was mixed with 20 ml of thionyl chloride and heated at reflux temperature for one hour. After cooling, excess thionyl chloride was distilled off and the remaining acyl chloride as a pale oil was taken up in 30 ml of dichloromethane. Subsequently, this solution was added dropwise to a solution of 2.4 g of 2-amino-1-butanol and 2.75 g of triethylamine in 30 ml of dichloromethane, retted in an ice bath. After the addition was complete, stirring was continued at room temperature for about 2 hours. The mixture was poured into ammonium chloride solution and extracted with ethyl acetate. 2.3 g of crude N- (1-hydroxy-2-butyl) -4-trifluoromethyln-cyanamide, obtained after drying and concentrating the ethyl acetate phase, was dissolved at room temperature in 100 ml of dichloromethane and mixed with 4.6 g of periodinane (Dess-Martin reagent). After the reaction had ended, according to TLC, the reaction mixture was concentrated and purified by column chromatography. 1.5 g of 2- (trifluoromethylpyridin-3-amido) butanal was dissolved in 30 ml of dimethylformamide, mixed with 2.72 g of phosphorus oxychloride and heated at 90 ° C for 15 minutes. The solution was poured onto ice and extracted with diethyl ether. Drying and concentration of the diethyl ether phase and chromatographic purification of the residue gave the product as a brownish oil. 1 H-NMR (CDCl 3, 300 MHz): d = 1.3 (t, J = 7.4 Hz, 3 H), 2.66 (cd, J = 7.4 Hz, J <1 H, 2 H), 7.58 (t, J <1 Hz, 1 H), 7.65 (d, J = 5 Hz, 1 H), 8.83 (d, J = 5 Hz, 1 H), 9.33 (d, J = 5 Hz, 1 H), ppm.

EXAMPLE No. 6 4-Ethyl-2- (4-trifluoromethyl-3-pyridyl) -4,5-dihydrooxazole (Table 5, No. 876) 1 g of 4-trifluoromethylnicotinic acid was mixed with 8 ml of thionyl chloride and heated at room temperature for one hour. After cooling, excess thionyl chloride was distilled off and the remaining acyl chloride was collected as a pale yellow oil in 10 ml of dichloromethane. Subsequently, this solution was added dropwise to a solution of 930 mg. 2-amino-1-butanol and 1.06 g of triethylamine in 10 ml of dichloromethane cooled in an ice bath. After the addition was complete, stirring was continued for about two hours at room temperature. The mixture was poured into an ammonium chloride solution and extracted with ethyl acetate. 1.03 g of crude N- (1-hydroxy-2-butyl) -4-trifluoromethylnicotinamide, obtained after drying and of concentrating the ethyl acetate phase, was dissolved at room temperature in 6 ml of tetrahydrofuran and mixed with 1.09 g of N - [(triethylammon) sulfonyl-J-methylcarbamate (Burgess reagent). The mixture was stirred at 60 ° C for three hours. After cooling, the filtrate was concentrated and the residue was taken up in water and extracted with ethyl acetate. Chromatographic purification of the crude product gave the product as a colorless oil. 1 H-NMR (CDCl 3, 200 MHz): d = 1.03 (t, J = 7.6 Hz, 3 H), 1.72 (m, 2 H), 4.15 (t, J = 7.5 Hz, 1 H), 4.32 (m, 1 H ), 4.58 (t, J = 7.5 Hz, 1 H), 7.6 (d, J = 5 Hz, 1 H), 8.87 (d, J = 5 Hz, 1 H), 9.06 (s, 1 H) ppm.

EXAMPLE No. 7 2- (3-Thienylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,4,4-oxadiazole (Table 3. No. 572) 880 mg of thiophene-3-acetic hydrazide was added to a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride and the mixture was heated at reflux for two hours. The reaction mixture was subsequently added, dropwise, to ice water; it was made neutral using concentrated ammonia solution and extracted with ethyl acetate. Drying over sodium sulfate, concentration and chromatographic purification gave 624 mg of the desired product as a light brown oil. 1 H-NMR (CDCl 3, 200 MHz): d = 4.38 (s 2 H), 7.1 (d, J = 5 Hz, 1 H), 7.23 (s, 1 H), 7.37 (dd, J = 5 Hz, J = 3 Hz, 1 H), 7.75 (d, J = 6 Hz, 1 H), 8.98 (d, J = 6 Hz, 1 H), 9.36 (s, 1 H) ppm.

EXAMPLE No. 8 5-Methyl-3- (4-trifluoromethyl-3-pyridyl) -1H-1,2,4-triazole (Table 6, No. 947) A mixture of 290 mg of ethylacetimidate hydrochloride and 100 mg of sodium hydroxide in 2 ml of ethanol, and 500 mg of 4-trifluoromethyl-3-pyridine-carbohydrazide was added, and the mixture was heated under reflux for three hours. The reaction mixture was concentrated and the residue was suspended in xylene and left to reflux for 4 hours. To work, the filtrate was diluted with ethyl acetate and washed with water. Chromatographic purification gave the pure product as a colorless solid. 1 H-NMR (CDCl 3, 300 MHz): d = 2.58 (s, 3 H), 7.64 (d, J = 5 Hz, 1 H), 8.85 (d, J = 5 Hz, 1 H), 9.19 (s, 1 H) ppm.

EXAMPLE 9 3- (N-isopropylcarba-t-oil-methyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole STEP 1: 3-amino-3- (4-trifluoromethyl-3-pyridincarbonyloxyimino) tert-butyl propionate Initially 30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid are charged in 150 ml of dry THF and, from time to time, mixed with 25.3 g of carbonyl-diimidazole. The mixture is stirred at room temperature for 30 minutes. 27.2 g of terbutoxycarbonylacetamide oxime dissolved in 150 ml of THF are added dropwise. The mixture is stirred overnight, the solvent is evaporated and the residue is taken up in ethyl acetate; Wash three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. The concentration of the ethyl acetate phase gives 28 g of the product as a pale yellow solid. 1 H NMR (CDCl 3, 300 MHz): d = 1.5 (s 9H), 3.3 (s, 2H), 5.55 (s broad, 2H), 7.83 (d, J = 5 Hz, 1 H), 8.97 (d, J = 5H, 1 H), 9.13 (s, 1 H) ppm.

Step 2: 3- (tert-butoxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole 28 g of 3-amino-3- (4-tifluoromethyl-3-pyridincarbonyloxyimino) tert-butyl propionate were dissolved in 380 ml of toluene and heated at reflux for 17 hours. Concentration and chromatographic purification of the residue on silica gel gives 14.4 g of the product as a pale brown oil. 1 H NMR (CDCl 3, 300 MHz): d = 1.5 (s 9H), 3.88 (s, 2H), 7.79 (d, J = 5 Hz, 1 H), 9.02 (d, J = 5 Hz, 1 H) , 9.33 (s, 1 H) ppm.

Step 3: 3- (Hydroxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole. 12.4 g of 3- (terbutoxycarbonylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and mixed with 57 ml of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 1.5 hours and subsequently concentrated under reduced pressure. The residue is repeatedly taken up in dichloromethane and reconcentrated to remove any remaining trifluoroacetic acid. Finally the mixture is triturated with diethyl ether, which gives 8.1 g of the product as a white solid.

Step 5: 3- (N-isopropylcarbamoylmethyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole Dissolve 1 g of the product from the previous step in 10 ml of THF and mix with 0.59 g of carbonyldiimidazole. The mixture is stirred at room temperature for 10 minutes. 0.22 g of isopropylamine are added dropwise and the mixture is allowed to react for another 1.5 hours, at room temperaturewith agitation. Subsequently the reaction mixture is concentrated and the residue is taken up in ethyl acetate and washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. The solid residue obtained is recrystallized after drying and concentrating the ethyl acetate phase in tert-butylmethyl ether, which gives 0.46 g of the pure product as a pale yellow solid. 1 H-NMR (CDCl 3, 300 MHz): d = 1.20 (d, J = 7.6 Hz, 6 H), 3.82 (s, 2 H), 4.12 (m, 1 H), 6.50 (broad s, 1 H), 7.81 ( d, J = 5 Hz, 1 H), 9.02 (d, J = 5 Hz, 1 H), 9.37 (s 1 H) ppm.

^^ ^ ^ ^ EXAMPLE No. 10 3- (N, N-dimethylaminocarbamoyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole Step 1: 2-amino-2- (4-trifluoromethyl-3-pyridine-carbonyloxyimino) ethyl acetate.

Initially, 17.3 g of carbonyldiimidazole are charged in 200 ml of 1,4-dioxane and, little by little, mixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. The mixture is stirred at room temperature for one hour and subsequently heated to 45 ° C for two hours. After cooling to 30 ° C, 14.5 g of ethoxycarbonylformamide oxime are added and the mixture is stirred at 45 ° C for three hours. The precipitated solid is filtered off with suction and the filtrate is concentrated to 50 ml and, together with the solid, is added to 250 ml of ice water. The solid is filtered off with suction and dried at 50 ° C under reduced pressure. This gives 28.7 g of the product as a white solid, with p. F. from 172-174 ° C.

Step 2: 3-ethoxycarbonyl-5- (4-tpfluoromethyl-3-pyridyl) -1,2,4-oxadiazole g of ethyl 2-amino-2- (4-trifluoromethyl-3-pyridincarbonyloxyimino) acetate are dissolved in 200 ml of a mixture of xylene and toluene, and mixed with 5 g of Amberlyst 15. The mixture is left to boil. at 125-130 ° C for six hours using a Dean-Stark apparatus. After the reaction has ended, it is cooled and the mixture is mixed with a small amount of diethyl ether. The mixture is filtered with suction through a glass filter pan and the solution is then concentrated. This gives 15.8 g of the product as a yellow oil.

Step 3: 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid.

Initially, 15.8 g of 3-ethoxycarbonyl-5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole are charged in 13 ml of methanol and, while cooling with ice at 0 ° C, it is added dropwise. a solution of 2.8 g of lithium hydroxide in 50 ml of water. The mixture is stirred at room temperature for two hours, 20 ml of ice water are added and the mixture is extracted with 200 ml of diethyl ether. The aqueous phase is adjusted to pH = 2 using dilute HCl, and the precipitated product is filtered off with suction. After drying 13.8 g of 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxylic acid is obtained, as a white solid, having a p. F. of 157-59 ° C.

Step 4: N, N-dimethyl-5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-3-carboxyamide .8 g of carbonyldiimidazole is initially charged in 90 ml of tetrahydrofuran and, little by little, it is mixed with 9 g of 5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole. The mixture is stirred at room temperature for 15 minutes and then heated at 50 ° C for two hours.

After cooling to room temperature, 2.3 g of dimethylamino is introduced into a very soft gas stream over a period of 2 hours. After a reaction time of 12 hours, the mixture is concentrated and taken up in 200 ml of diethyl ether. The mixture is washed with hydrochloric acid solution in an average concentration, cooled with ice, washed with saturated sodium bicarbonate solution, until neutral, dried over magnesium sulfate and concentrated under reduced pressure. This gives a slightly yellow oil that (lacuna) after several days changes to a solid with p. F. of 52-54 ° C. In a similar manner it is possible to prepare the compounds shown in the following tables 1 to 6: The abbreviations used denote: Ph = phenyl THP = 2-tetrahydropyranyl.

TABLE 1 INo. IX Y.m iW R! i.f.í'C] 1 iN iCCl. lO lO iCH,, N .cc-, 0 Or CH-CH Do not. iX, Y; m W 'R p.f. [TO]; 12 .CH | (CF;.; CHF; 0 0 'NHCH-' iNo X .Y m IVV iR p.f.f'C] Do not. , X And T? W IR P.f. [° C] 175 .CH iCF2C; 0, 0 CHAONHCH. 76 iCH | CF2CI O 0, OCH, I 1 > i 77 ¡CH ¡CF, CI O ¡O INHCHI I 78, CH CF,, 0 ¡O | CH, oil 79 ¡CH CF3, 0 0 | CH2CH, i oil 'l 80 CH CF3 0 0 | (CH2) 2CH, I oil i 81 iCH | CF3 0 0 ¡CH (CH,), I oil i i I i 82 ICH! CF3 0 0 Cycle-C3H5 I oil! I i 183 'CH ICF, O ¡O ¡(CH CH- oil iNo , X Y m ¡W ¡R • p.f. ° C,, ¡102 CH CF CF, 0,, CH (CH, CH..) (CH;> 5CH, 103 CH CH ICF., 0 O O ((CH,), CH, I! I 104 ¡CH | CF, ¡0, 0, (CH2j, -cicloC.H ,. 105 ¡CH ICF, ¡0 ¡O | (CH,) 9CH3 < '129 iCH ICF, 0 or 1CH: C = CH 1130 ¡CH ICF3 0 IO | CH: CH2C - CH ¡1 1 I I 1 1131 ¡CH ¡CF3 0 ¡O ICH-CH, CpCH ¡132 ICH CF3, 0 ¡o (CH,). CHCH ¡133 ICH ¡CF, lO | O CHFCF oil 1137 ICH ICF3 0 10 ICHjCOOCíCHjh oil No., X And m, VV ¡R .p. £. [ßC] 1156 ¡CH ¡CF, 0 0 2-Pyridyl 99- 101 157 ICH ¡CF,: 0 | :! 0 2-Furilo • 158 ¡CH ICF, .0 I i i | 0! 2-Thienyl! 106-108! 1159 CH CF, ¡0 ¡0 | CH, C = CCH, CH: 0THP I i I -! 160 ICH ¡CF, lO lO CH, CH, CI oil 161 ICH | CF, 0 ¡O ¡Si (CH3) 3 162 | CH | CF, 0 O | OC6H5 163 CH CF3 0 | O lOH ¡164 ¡CH ¡CF, 10 ¡O IOCH, INo. , X Y m, v: R p.f.í'C] 1210 iN CF, 0 0 CH: Cri = CH: iNo? And m i ¡R p. f .r]? 264 iN CF. 0 S, CH COOC'Cp-j. 265 iCH ?CH, CH;I CI 0 0 CH CH- 1 266, CH CH, CH 2 Cl 0 0 CH, CH 3 1 1267 CH ICH, CH 2 Cl > 0 0 | (CH.), CH3. 1 1 i 1 268 ICH | CH: CH: C1, 0 10 ICHfCH3) 2 ¡269 ICH CH: CH2C1? 0 10 CH SCßH5 i l I | 270 ICH iCH-.CH-.Cl 0 ¡0 CH2CONHCh: | ! I 1 ¡271 CH? CH2CH2CI ¡0 IO NH2! I i i I 272 ICH lCH2CH2C I 0 I INHCH2CH 273 I N, CH-CH I C O O 'CH, CH 1274, N, CH, CH, CI, 0 | 0 | NH- 1280 ICH ICHF- O ¡O | CH, CH = CH, 'I '291 IN CHF: 0 0? CH2CH I I292 IN iCHF- lO 0 ¡CH (CH,) (CH2) H ¡¡ I! l ¡293 IN? CHF ¡0 0 ICH2CH = CH, 299 'CH ICF, 1 OR CHFCF I307 ICH ICF, 0 S l (CH: ^ S (CH,) -, CN INo. , X Y m ¡VV ¡R p.f. [° C]; 318 ¡CH ICF, .0, S CH: .I6IN1HCH2CF 1 I | 319 ¡CH ICF,, 0 IS ¡(CH,), 0 (3-CH3) -C6H- 1 I '1 I' 1 I I326 CH ICF, 0 iO l (CH:) - NHCH, CF- ¡327 ¡CH! CF3, 0, 0, (CH: .NHCH, CN N ?. ? X Y, IW ¡R .f. [ßc] 356 ICH iCF, .0 .0 'CH; CH: 0 (CO? -cicloC, h-? Oil 357 ICH ICF, O ¡O ICH2CH, 0 (C0 CH, i oil 358 ICH ICF, O O lCH2- [2.4- (CH?): -? 85 - 86 379, CH, CF 0 ¡O CH CONCH, Cp, -c? CloAp- 35 380 CH | CF, O | CH2CONCH (CH3) (2-Naphthyl) 142 - 146 1381 ¡CH CF3 0 O (CH2) 3CI oil 382 ¡CH CF3 OR CH2CON-tert-C4H9 oil 383 ICH CF, ¡0 ¡O | CH, WITH (? So-C, H7) 2 | 70 - ^ 2 , 384 | CH, CF 0 O Ch: CON (Ch -CH 79 - 31 390 ICH ICF 0 'O (CHASCH.OIL, N?? X Y m? V i R p.f.l'Cl | .420 ICH iCF 0 0 i CH.CON-CA-, 215-217 'INo. , X Y m iW IR 'p.f. r. 1437 \ CH ¡CF, • 0 ¡O ¡CH-CONCH-cidoC-.p- acei e i! 438 CH CF3 O 0 | CH2CON (CH2) 5OH, oil i 439 CH CF, 10 10 CH2C0N (CH3) (CH2C0; CH,) oil I | -, CH-C N H, CH.O p - 448 iCH ¡CF, 0 ¡O | CH3CON- (2-OH) C6H. 162-164 449 CH CF, OR CH: CON-. { 3-OH) CoH4 oil 450 CH CF, OR CH2CON- (2-CH3) CéH- 163- 164 1454 ICH ÍCF3 ¡0 IO | CH, CON- (2.4-Cl2.}. C H, ¡120- 122 No.? X ¡Y m ¡W iR .f.r] i Do not. ,? And, m iW IR p.f. [° C] 4871 CH! < F: 0, 0, CH; C0N-? Z-CN-4-C /, C-rt 157 A 59 i 1 488 ICH CF; 0 | CH2CON- (3.5-C):? C.p- 167- 169 i 1 'I 489 ¡CH ICF, ¡0 O l CH2CON- (3.5-C,: - 4-OCF; ChF:, C H; 132- 134 1 1 I I 490 CH ÍCF3 ¡0 0 CH > CON-? 2.45-C; ,, C6h; 146 I I 491 CH CF3, 0 or CH2CON-l3.5-C,: - 4-OCF.CHFCF,) CA. 124 - 126 i | 492 iCH CF3 ¡0 I I I Io CH, CON- (2-CF, -4-C¡) C6H: 1136 I L04 No X Y <m W 'R, p. £. (ßC] , 510, CH iCF; 0 OR CONHCH, 127-129 1 1 1 1 1 1 1 511 ICH ICF, 0, 0 ICONHCH, CH = Ch: oil 1 I i 1 512 ICH | CF3 0 10 'CON (CH, CN) 2 90-92 I 513 ICH CF3 0, 0 .4- t-C4h5) -C6H4 ¡64-66 ¡I! 514 CH CF3, 0 10! 4-CF, -C6H4 -89-91 1515 CH | CF3 10 10 4-CH, -3-F-C6H3 '104-106 1 i | N ?. , X, Y m IW IR I p. f .rC] 529 ICH ICF, 0 10 'oil i 1' 534 ICH | CF3 0 or oil 535 ICH CF3 0 10 lCONH -? - C4H9 oil 536 ¡CH CF-, 10 lO oil 537 ICH CF3 O, CON (CH2) 4 168-70 538 CH | CF3 OR CON (CH, j-n-CH13 oil 539 ICH CF oil , No, X Y m W IR .f.r] Do not. , X ¡Y .m W IR íp.f.r] | 555 iCH ICF,, 0 O: CONH (CH2) 3C6H5 oil I? I | 556 ICH ¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡HCHH-3-Pyridyl ¡132-134 i , 572 ¡CH ¡CF, 0 O CONICCH iCH Cri oil i I I 1 1573 ICH CF, O CON (CH;) CH2CN oil 574 ICH ¡CF, ¡0 10? WITH (CH,) CH2CH2N (CH /: oil 575 CH | CF3 0 ¡O ¡CONHOCH2CH3 114-116 576 ICH CF, O 'CONHCHsCFj • to 577 CH CF3 10 IO CON (CH, CH, CI), oil '578, CH ICF, 0 OR CONH-c-C-h- oil 1583 ICH | CF, ¡O, 0 CONHOCIACA '26 -128 No. ¡X Y m i W l R, p.f. ['C], 591 ICH ¡CF, 0 0? CONHO-t-C-A 103-105 I No X Y t? iW R p. f. rc] i 1602 ICH ICF. 0 OR CONIC. CH,; Cp C-i OCh oil 603 ICH ICF, 0 p i oil '¡i > 604 ÍCF, or p oil 1605 ICH ¡CF,? O oil 617 ICH | CF3 10 10 oil 618 CH CF3 | 0 O | CON (CH3) CH2-d-CI- 3-Pyridyl oil 619 ¡CH | CF3 lO ¡O 1105-107 I I l 620 < : H CF3 0 P? CONHCH (CH3) CH (OCH3) 2 | I i oil | 621 ICH CF3 0, 0 CONHCH2CH2SCH3, oil 622 ¡CH ¡CF3 0 0 ICONHCH (CH3) CH2OCH3 70-72 I 623 ¡CH CF3 ¡0 0 CONHCH2CH, NHCOCH3 124-126 624 CH CF3 ¡0 0 CONH (CH2) 3OCH2CH, i oil 625 CH CF3 ¡0 O! CON (CH, CH,) CH, CH, CH3 i oil, I I I i INo. X ¡Y m iW ¡R p.f. rc] 1 1 1 643 ICH CF3 0 1 0, CONHCH, CH = CHCH2C1 oil 1 1 1 644 | CH CF3 0 0 ¡C0NH-4-C0NHCH, -C H .219-221 ! ! 645 CH CF3 0 0 CONHCH, CH, CH2Br oil i i I 646 CH CF3 0 or CONHCH2CH, CH2OCH3 oil 647 CH CF3 0 0 CONH-4-CH; CH3-C6H4 .97-99 648 ICH ¡CF3 ¡0 ¡OR ICONHCH2CH: OCH (CH3) 2 oil 14 TABLE 2 Nr., Y w im.p. I Í 684 iN, CF2 3CHF2? O CH3 17 iNo X Y W P-f-TC] 1 1 3 , 732 ¡CH ICF; P, CH, CN, 733 iCH ICF, 10 | CH.CHí-0-? CH:, 1 734 ICH | CF3 1? 1 ° CH, (4-0CH, P6H = i! I 735 ¡CH ¡CF, or CH2CH (OH) CH2SC, p- ¡1 '736 ¡CH ICF, 10 CH = CF: ¡1 1 ¡737 CH CF3 0 CC! = CHC! I 738 CH ICF, 0 1 2-Pyridyl 739 ¡CH CF3 10 OC6H5 740 ¡CH CF; O OH INo. X, Y W p.f. 816? N CF,, 'CH-?: ^ H 817 IN | CF3 ¡CHFCF ¡818 | N ICF PH, CH, OH 819 IN CF3? CH2COCC (CH3) 3 823 ICH ICHF2 O | CH3 824 CH ICHF; P 'CH, Ch- TABLE 3 ^ No Y im IV p.f.rc] 1840, N (CF:? PHF:? 0 10 ICH3 849 IN ¡CF3, 0 ¡O CH, CH, INo X Y 'm | V P.f. íßc] , N? X Y m? V R ¡p. f. 1000! CH iCHF; 0 ¡0 iNHCOCH-, 1001 ¡N, CF2CF. 0 IS | CH, > ,,, 1002 N CF2CF; , 0 S CH; CH, 1003 ¡N ¡CF2CF, 0 ¡s (CH2) 2Ch; ! i I 1004 | N ¡CF3 | 0 ¡s ICH, 1005 N CF3 0 IS ICHoCH, 1006 N CF, 0 ¡s | (CH;), CH, I i I 1007 N CF3 0 s CHFCF, l 11008 | N CF, 0 jS ¡CH2CH, OH | 1009 ¡N ICF- > 0, S, CH, COOCíCH; /: 11010 | CH | CF3 0 | S CH, 1017 ICH CF, 0, S CH, COOC (CH, 11018 | CH ICF, CH, CN TABLE 4 , 0 ?. No IX | Y m ¡V IR '| RJ, p.f. [ßC] '1019 IN, (CF 3CHF. 0 S H CH, CH, 1028 IN | CF, 0 S, CÍCh- H iNo X Y m iV 'R- R ", p.f. rc¡, , 1039 ¡CH 'CF: 3, 3, CÍCH; I. CCOCH.CH- I 1040 ¡CH ¡CF; 0 S iH CONHCH2CH, I 1041 ICH ICF-0, S iH CCN (CH, CH3., 1042, CH | CF, 0, S iH COOCH, Ch, l oil 1043 CH ICF-, 0? S | H CH: COOCH, CH, I oil I i 1044 ¡CH ¡CF-, 0 s H CH, CHO I I i I 1045 ICH ICF- 0 ¡s H CH-OCH3, 1046 CH | CF; 0 ¡s H, CH, OCH, Ph I I 11047 ICH ICF; 0? S IH H No X Y m R ", p.f.¡ 11067 CH ICF 0 S COOCH.CH H 11068, CH ¡CF 0 3, CH: CH: OH H, I! 1069 ¡CH ICF. 0 S, CH; CH, OCH. I! 11070 ¡CH | CF3 0 S, CH2COOC (CH ^ 3 H 1071 ¡CH ICF. 0 S CH, COCH, H 1072 I CH | CF- ¡0 S ¡COCH3? I "I I 1073 ICH CF, IO S lCH, Oph H 1074 CH CF3 ¡0 S, COPh H 'I' 1075 ¡CH ¡CF3 0 3 CO (4-C¡) -C6H4 H I075 iCH ¡CF 0 S CF, CH 1084 IN CF, 0 3 H Ch CIAOCH, No. X Y m p- R- 1095 iN ¡CF, ü i; H C OCH Ch 1096 ¡N | CF, 0 S? CH; Ch: C-CH OCH.CH No A Y TI V R- R 'p.f. ? "C], 1123 ¡¡CF ¡; 0, 0 rt, CH_ 1124.CH iCF: 0 ¡¡¡¡H cicloCHc 1125, Ch | CF4 3, 0 ¡H CH, CH, Ch I 1126 ¡CH ¡CF- 0, 0 ¡H ¡Ph, 103-104 I 1127 I CH ICF, 0 O, H 2-Pyridyl 1128 i Ch | CF; 0 ¡°! H 2-Furilo, 1129 ¡CH ¡CF3 ¡o 0 ¡icloCíhc; H; I 1130 Cri ICF3 ¡0 ¡O ICH, COOCH, CH3 I I! I I "11131 CH ICF, ¡0 ¡O | CH, POOH 1132 Ch iCF 0, 0, CH, CONH, 1140 ICH | CF, 0, 0 SCH, CH2C - Ch • H TABLE 5 TABLE 6, - N? , \ 0 A • R R p.f. C "295 CH ZF Cp C, \ OCH.F-1296 iCH CF CH, C \ OCONHP-1297 iCH CF, Cp: CN OCCNh- -FI-C-I 1298 ICH iCF, Crí OCH.CH OCH- 1299 ICH CF CH-OCACh OCH, Cr I 1300 iCH ICF, CH OCH, Cp OCHF. 1301 ¡CH CF CH, OCH, Ch OCH, Fn l ¡1302 ICH? CF, CH, OCH, CH PCONHP ^ I, "&"; I ¡1303 ¡CH ¡CF; | H CH,, 203-204 11313 ICH, CF3.ri Ch, Cp Cri = CH- 1324 ICH ¡CF,, ri CH, SPh 1325 ICH iCF: ¡¡¡CH, CONHCH3 '1326 \ Cn ¡CF, h, CH2COCH3 | 1327 ICH ¡CF,, H .COCH3 11328 ICH? CF3 ¡H ¡CH2Opn 1329 ICH ¡CF, ¡H ¡COPh 1330 CH | CF3 | H COÍ3-C¡) -C-.H4 11331 CH ICF,? CF2CH3 I C- BIOLOGICAL EXAMPLES EXAMPLE 1 A Petri dish is prepared whose bottom is covered with filter paper and containing about 5 ml of culture medium. It is immersed in the aqueous solution of the formulated preparation to be examined, for 5 seconds, pieces of filter paper with around 30 eggs of 24 hours of aging, of the American tobacco worm (Heliothis virescens), and subsequently placed in the Petri dish. Another 200 μl of the aqueous solution is spread on the culture medium. The Petri dish is closed and then kept at around 25 ° C in a heated chamber. After 6 days of storage the effect of the preparation on eggs and larvae that may have hatched from them is determined. At a concentration of 300 ppm (based on the content of active compound) the preparations of examples No. 79 and 88 effect a 90-100% mortality.

EXAMPLE 2 Germinated bean seeds (Vicia faba) are transferred with radicles to dark glass bottles filled with running water and subsequently populated with about 100 black bean aphids (Aphis fabae). The plants and aphids are then immersed for 5 seconds in an aqueous solution of the formulated preparation to be examined. After the solution has been drained, the plant and the animals are kept in a heated chamber (16 hours of light / day, 25 ° C, 40-60% of relative atmospheric humidity.) After 3 and 6 days of storage the effect of the preparation on aphids At a concentration of 300 ppm (based on the content of active compound) the preparations of examples No. 79, 78, 80, 81, 83, 84, 88, 133, 135, 136 , 137, 138, 139, 1117, 1229, 1230, 1231, 1246 and 1254, effect a mortality of 90 to 100% among the aphids.

EXAMPLE 3 The leaves of 12 rice plants having a stem length of 8 cm are immersed, for 5 seconds, in an aqueous solution of the formulated preparation to be examined. After the solution has been drained, the rice plants treated in this way are placed in a Petri dish, and they are populated with approximately 20 larvae (stage L3) of the rice leafhopper species Nilaparvata lugens. The Petri dishes are closed and stored in a heated chamber (16 hours of light / day, 25 ° C, 40-60% relative atmospheric humidity). After storage for six days, the mortality among the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound) the preparations of Examples No. 88, 139 and 927 effect a kill of 90-100%.

EXAMPLE 4 Germinated bean seeds (Vicia faba) are transferred with radicles to dark glass bottles filled with running water. Four milliliters of an aqueous solution of the formulated preparation to be examined is pipetted into the dark glass bottle. Subsequently, the beans are heavily populated with approximately 100 black bean aphids (Aphis fabae). Then plant and animals are stored in a heated chamber (16 hours of light / day, 25 ° C, 40-60% relative atmospheric humidity). After storage for 3 and 6 days, the root systemic activity of the preparation is determined on the aphids. At a concentration of 30 ppm (based on the content of active compound), the preparations of examples No. 78, 79, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 187, 1117, 1229, 1230, 1231, 1246 and 1254 carry out a mortality of 90-100% of the aphids, by systemic root action.

Claims

NOVELTY of the INVENTION CLAIMS

1. - A 4-halogenoalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclylpyrimidine of the formula I, if desired in the form of its salt: characterized in that Y is haloalkyl of 1 to 6 carbon atoms; X is CH or N; m is 0 or 1; Q is a group 5-member heterocyclic in which: -UÉ-i ü a-H- a) X1 = w, X2 = NRa, X3 = CR R1 0 i} x1 = v, - X2 = CRaR2. x3 t = CRV 0 < x1 S V, X = CR4R5r X3 = CRßRT 0 f) x1 - NRa, X2 = CRbR1. X3 = NR8; Ra and Rb together are a ligature; V is oxygen, sulfur or NR9; W is oxygen or sulfur; R1 is hydrogen, alkyl of 1 to 20 carbon atoms, alkenyl of 2 to 20 carbon atoms, alkynyl of 2 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein the last six mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, hydroxyl, -C (= W) R10, -C (= NOR10) 10, ^ C (-NNRt02) R1 °. -C (= WJ0R1 °, -C (-W) NR102 < - OC (= W) R1, -0C (= W) OR10. -NR10C (= W) R1 °, - N [C (= W) Ri 0] 2, -NR 0C (=) OR1 °, -C { -W) NR10-NR102, -C (= W) NR10.NR10 [C (=) R10] l -NR10-C (= W) NR102-NR10-NR10C (=) R101 -NR10 ^ [C (= W) R10] 2, -N [(C = W) R10] -NR1 ° 2, NR10-NR10 (C = W) RlQ] r -NR1C -NR10HC = W) WR10l, NR10 (C = NR1O) NR1 ° 2 < O-NR102l -0-NR1 tV W) R1 C \ -S02NR1D2. -NR ^ SOzR10, S020R10 -OS02R1 ° -OR10 ° 2, -SR10, -SiR103. SeR ^ .pR ?? 2 _p (í5W) R? O2? SOR10, -S02R10, -PW2R102. -P R1 ° 2l and aryl and heterocyclyl; the two radicals mentioned at the end are optionally substituted with one or more radicals selected from the group of: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms, halogenoalkyl of 1 to 6 carbon atoms, halogenoalkenyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms carbon, -OR10, -NR102, -SR10, SiR103, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -SOR10, -SO2R10, nitro, cyano and hydroxyl; aryl that is optionally substituted with one or more radicals from the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl from 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein these six radicals mentioned above are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -OR10, -NR102, -SR10, -SOR10, -S02R10, halogen, cyano, nitro, -C (= W) R10, -C (= NOR10) R10, -C (= NNRi s2) R10, -C (-W) OR10, .C (= W) NR102I -OC (= W.}. R1 ° > -OC { = W) OR1 °, -NR10C ( =) R10, ^ IC (=) R10] 2 > -NR10CÍ =) OR10P -OR10, -NR102, -SR 0 -SiR1 ° 3, -PR102. -SOR10. -PW2R1 ° 2 Y ^ P 3 10, heterocyclyl which is optionally substituted with one or more radicals from the group of: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; where the last six mentioned radicals are optionally substituted with one or more radicals from the group of: cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -NR10C (= W) R10, -N [C (= W) R10] 2, -OC (= W) R10, -OC (= W) OR10, -OR10, -NR102, -SR10, -SOR10 and -S02R10, halogen, cyano, nitro, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -OC (= W) E10, -NR102, -SR10, -SOR10 and-S02R10, -OR10, -R1 ° 2, -SR10 -SOR10 -S ^ R10 -C (= W) R1 °, -C (= N0R1 V ° -C (-NNR1Ü2) R10 -C (=) OR10 -C (=) NR102l -OC (r) R10, -OC (= W) OR1 Ü, -NR1 ° CÍ = W) R? 0 -N [C (= W) R10] 2l -NR 0C (-W) OR10. -C (= W) NR10-NR102 > -NR 0 -NR10C (= W) R10, -NR10-NC (= W.}. Ri02, -N (C = W) R10 -NR102, -NR10-NR10 [(C = W) R10]. -NR10- NR10 [(C = W) WR10], -NR10 (C = NR 0) NR1 ° 2, -O.NR102l -0-NR1 ° { C =.}. R10 -S 2NR102, -NR10SO2R10, -SO2OR10 * OS02R1 -SC (= W) R10, ^ SCÍ = W) OR1 ° P -SC (= W) R101 -PR102l -P 2R102l -PW3R102 > SiR103 or halogen; R2 and R3, independently of each other, have the definitions n in R1; R2 and R3 together form a 5- to 7-membered ring which may be partially or wholly unsaturated and may be interrupted by one or more atoms of the group of nitrogen, oxygen and sulfur; without the oxygen atoms being directly adjacent to each other, and the ring optionally being substituted with one or more, but at most five, radicals R1; R4 and R6, independently of each other, have the definitions n in R1; R4 and R6 together form a 4- to 7-membered ring, which may be partially or wholly unsaturated and may be interrupted by one or more nitrogen, oxygen and sulfur group atoms; without the oxygen atoms being directly adjacent to each other, and the ring being optionally substituted with one or more, but at most five, radicals R1; R5 and R7, independently of each other, are hydrogen; alkyl of 1 to 20 carbon atoms, alkenyl of 2 to 20 carbon atoms, alkynyl of 2 to 20 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms; wherein the last six mentioned radicals are optionally substituted with one or more radicals of the group: halogen, cyano, nitro, hydroxyl, -C (= W) R10, -C (= NOR10) R10, aryl and heterocyclyl; of which the last two mentioned are optionally substituted with one or more radicals of the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkynyl of 6 to 8 carbon atoms, halogenoalkyl of 1 to 6 carbon atoms, halogenoalkenyl of 2 to 6 carbon atoms, halogenoalkynyl of 2 to 6 carbon atoms, halogen , -OR10, -NR10, -SiR103, -C (= W) R10, -C (= W) OR10, -C (= W) NR102, -SOR10, -S02R1 °, nitro, cyano and hydroxyl; aryl that is optionally substituted with one or more radicals of the group: alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; wherein these last six mentioned radicals are optionally substituted with one or more radicals of the group: halogen, cyano, nitro, halogen, -C (= W) R10, -C (= W) OR10, -C (= W) NR102 > -OR10, -NR102, -SR19, -SOR10 and -S02R1 °; halogen, cyano, nitro, -C (= W) R10, -C (= NOR10) R10, -C (= NNR102) R10, -C (= W) OR10, -C (= W) NR102, -OC (= W) R10, -OC (= W) OR10, -NR10C (= W) R10, -N [C (= W) R10] 2, -NR10C (= W) OR10, -C. { = NNR102) R10, -C. { = W) OR10 -C. { = W) NR102t - OC (= W) R10, -OC (= W) OR10 -NR10C (= W) R1 °. - NíC (* W.}. R1 ° J2, -NR ° C (= W) OR1 °, -C { = W) NRT ° -NR1 ° 2, -C (= W) NR10-NR10? CÍ = W) R1 ° J, -NR10-C (= W) NR102, -NR10-NR10 [(C =) R10] P R10, ° 2, -SR10. ^ SiR103, -SeR1 -PR102, -P (= W) R102, -SOR10, -S02R1 °, -PW2R102, ^ PW R102r -OR10, -NR102, -SR10, -SiR 03, -PR102) -SOR10, -S02R10 , -PW2R102 and -PW3R102; pyridyl, which is optionally substituted with one or more radicals from the group: alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms and cycloalkynyl of 6 to 8 carbon atoms; where the last six mentioned radicals are optionally substituted with one or more radicals of the group: cyano, nitro halogen, -C (= W) R10 -C (= W) OR10, -C (= W) NR102, -OR10, -NR102, -SR10, -SOR10 and -S02R1 °; halogen cyano, nitro, -C (= W) R10, -C (= W) OR10, -C (= W) NR102 -OC (= W) R10, -OR10, -NR102, -SR10, -SOR10 and -S02R1 °; -C (= W) R10 -C (= NOR10) R10, -C (= NNR102) R10, -C (= W) OR10, -C (= W) NR102, or halogen; R4 and R5 together form a 4- to 7-membered ring, which may be partially unsaturated and may be interrupted by one or more atoms of the group of nitrogen, oxygen and sulfur; without the oxygen atoms being directly adjacent to each other, and the ring optionally being substituted with one or more, but at most five, radicals R1; R4 and R5 together form one of the groups = 0, = S or = N-R9; R6 and R7 together form a 5- to 7-membered ring, which may be partially unsaturated and may be interrupted by one or more atoms of the group of nitrogen, oxygen and sulfur; without the oxygen atoms directly adjacent to each other; and the ring being optionally substituted with one or more, but at most five, radicals R1; R6 and R7 together form one of the groups = 0, = S or = N-R9; R8 is hydrogen; alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms, cycloalkenyl from 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 atoms of carbon, C2-C6-alkynyl-C3-C8-cycloalkyl, C1-C6-C3-C3-C3-C3 alkyl, C2-C6-C3-C3-C3 alkenyl 4 to 8 carbon atoms; wherein the last fourteen mentioned radicals are optionally substituted with one or more radicals from the group: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy from 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, halogenoalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkoxy of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms- alkoxy of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyloxy of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyloxy of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon-cycloalkoxy atoms of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms -cycloalkenyloxy of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkenyloxy of 2 to 6 carbon atoms, carbamoyl, mono- or dialkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, mono or dicycloalkyl of 3 to 8 carbon atoms - carbamoyl, alkoxy of 1 to 6 carbon atoms - carbonyl, cycloalkoxy of 3 to 8 carbon atoms - carbonyl, alkanoyloxy of 1 to 6 carbon atoms, cycloalkanoyloxy of 3 to 8 carbon atoms, halogenoalkoxy of 1 to 6 carbon-carbon atoms, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanoid of 1 to 6 ato carbon atoms, halogenalkanoid of 1 to 6 carbon atoms, alkenanid of 2 to 6 carbon atoms, cycloalkenamide of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkanamide of 1 to 4 carbon atoms, alkylthio from 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio d 2 to 6 atoms of carbon, cycloalkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms - alkylthio 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylthio of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms carbon-alkenylthio from 1 to 4 át carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, halogenoalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 atoms of carbon-alkylsulphinyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfinyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylsulfinyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms carbon, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms - alkylsulfonyl from 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfonyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 atoms of carbon-alkenylsulfonyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkenyl ________________________i_i_____i______ of 2 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, halogenoalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino of 4 to 8 carbon atoms, halogenocycloalkano of 3 to 8 carbon atoms, halogenocycloalkenylamino of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylamino of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylamino of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms carbon, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aroyloxycarbonyl, aryl -alkoxy of 1 to 4 carbon atoms, aryl-alkenyloxy of 2 to 4 carbon atoms, aryl-alkylthio of 1 to 4 carbon atoms, aryl-alkenylthio of 2 to 4 carbon atoms, aryl-alkylamino of 1 to 4 carbon atoms, aryl-alkenylamino of 2 to 4 carbon atoms, aryl -dialkylsilyl of 1 to 6 carbon atoms, diaryl-alkylsilyl of 1 to 6 carbon atoms, triarylsilyl and 5- or 6-membered heterocyclyl; of which, the nineteen mentioned radicals at the end are optionally substituted in their cyclic portion with one or more substituents of the group: halogen, cyano, nitro, amino, hydroxyl, thio, alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogenoalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, halogenoalkylamino of 1 to 4 carbon atoms, formyl and alkanoyl of 1 to 4 carbon atoms, aryl, which is optionally substituted with one or more radicals from the group: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, haloalkynyloxy of 2 to 6 carbon atoms carbon, cycloalc oxi of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, carbamoyl, mono- or dialkyl of 1 to 6 carbon atoms -carbamoyl, alkoxycarbonyl of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, halogenoalkoxy of 1 to 6 carbon atoms-carbonyl, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanamide of 1 to 6 carbon atoms, halogenoalkanamide of 1 to 6 carbon atoms, alkanamide of 2 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio of 2 to 6 carbon atoms, cycloalkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, haloge nocicloalkyltil of 3 to 8 carbon atoms, halogenocycloalkenylthio of 3 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, haloalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alke nilamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, halogenoalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino of 4 to 8 carbon atoms, halogenocycloalkyl of 3 to 8 carbon atoms, and halogenocycloalkenylamino of 4 to 8 carbon atoms, -C (= W) R11, OR11 or NR112; R9 is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 at 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms , cycloalkenyl of 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms; wherein the last nine mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, and halogenoalkyloxy of 1 to 6 carbon atoms; R10 is hydrogen; alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkyl of 3 to 8 v alkenyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms alkynyl of 2 to 6 carbon atoms-cycloalkyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyl of 4 to 8 carbon atoms; where the last fourteen mentioned radicals are optionally substituted with one or more radicals from the group of: halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 and alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms, halogenoalkenyloxy of 2 to 6 carbon atoms, halogenoalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms , halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkoxy of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkoxy of 1 to 4 carbon atoms carbon, cycloalkyl of 3 to 8 carbon atoms-alkenyloxy of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenyloxy of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkinyl of 2 to 6 carbon atoms-cycloalkoxy of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms -cycloalkenyloxy of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms-cycloalkenyloxy of 4 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms carbon-alkenyloxy of 2 to 6 carbon atoms, carbamoyl; mono- or dialkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl, mono- or dicycloalkyl of 3 to 8 carbon atoms-carbamoyl, alkoxy of 1 to 6 carbon atoms -carbonyl, cycloalkoxycarbonyl of 3 to 8 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, cycloalkanoyloxy of 3 to 8 carbon atoms, halogenoalkoxycarbonyl of 1 to 6 carbon atoms, halogenoalcanoyloxy of 1 to 6 carbon atoms, alkanoid of 1 to 6 carbon atoms, halogenalkanoid of 1 to 6 carbon atoms, alkenanid of 2 to 6 carbon atoms, cycloalkanamide of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkanamide of 1 to 4 atoms of carbon, alkylthio of 1 to 6 carbon atoms, alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio 2 to 6 carbon atoms, cycloa alkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylthio of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylthio of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylthio from 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylthio of 3 to 8 carbon atoms, alkenyl of 2 to 6 atoms of carbon-cycloalkylthio of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 5 carbon atoms, alkenylsulfinyl of 2 to 6 atoms carbon, alkynylsulphinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, haloalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogenocycloalkylsulphinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms carbon-alkylsulfinyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylsulfinyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfinyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfinyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cic loyalkylsulfinyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms, halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms carbon, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkylsulfonyl of 1 to 4 carbon atoms, cycloalkyl of 3 at 8 carbon atoms-alkenylsulfonyl of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylsulfonyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-c icloalkylsulfonyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylsulfonyl of 3 to 8 carbon atoms, alkyl of 1 to 6 carbon-cycloalkenylsulfonyl atoms of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, haloalkynylamino of 2 to 6 carbon atoms, cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino of 4 to 8 atoms carbon, halogenocycloalkyl of 3 to 8 carbon atoms, halogenocycloalkenylamino of 4 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkylamino of 1 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms o-alkylamino of 1 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms-alkenylamino of 2 to 4 carbon atoms, cycloalkenyl of 4 to 8 carbon atoms-alkenylamino of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms, alkynyl of 2 to 6 carbon atoms-cycloalkylamino of 3 to 8 carbon atoms C 1 -C 6 -alkyl-cycloalkenylamino alkyl of 4 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms-cycloalkenylamino of 4 to 8 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, aryl, aryloxy , arylthio, arylamino, aryl-alkoxy of 1 to 4 carbon atoms, aryl-alkenyloxy of 2 to 4 carbon atoms, aryl-alkylthio of 1 to 4 carbon atoms, aryl-alkenylthio of 2 to 4 carbon atoms, aryl -alkylamino of 1 to 4 carbon atoms, aryl-alkenylamino of 2 to 4 carbon atoms, aryl-dialkylsilyl of and 1 to 6 carbon atoms, diaryl-alkylsilyl of 1 to 6 carbon atoms, triarylsilyl and 5- or 6-membered heterocyclyl; where the cyclic portion of the last fourteen mentioned radicals is optionally substituted with one or more radicals from the group: halogen, cyano, nitro, amino, hydroxyl, thio, alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 4 carbon atoms , cycloalkyl of 3 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogenoalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, halogenalkylamino of 1 to 4 carbon atoms, formyl and alkanoyl of 1 to 4 carbon atoms, aryl, heteroaromatic of 5 or 6 members, where the last two mentioned radicals are optionally substituted with one or more radicals of the group : halogen, cyano, nitro, hydroxyl, thio, amino, formyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, halogenoalkyloxy of 1 to 6 carbon atoms , he has logenoalkenyloxy of 2 to 6 carbon atoms, halogenoalkynyloxy of 2 to 6 carbon atoms, cycloalkoxy of 3 to 8 carbon atoms, cycloalkenyloxy of 4 to 8 carbon atoms, halogenocycloalkoxy of 3 to 8 carbon atoms, halogenocycloalkenyloxy of 4 to 8 carbon, carbamoyl, mono- or dialkyl atoms of carbon-carbamoyl, alkoxycarbonyl of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, mono- or dihaloalkyl of 1 to 6 carbon atoms-carbamoyl of 1 to 6 carbon atoms, halogenoalkoxycarbonyl of 1 to 6 carbon atoms, alkanamido of 1 to 6 carbon atoms, halogenoalkanamide of 1 to 6 carbon atoms, alkenanide of 2 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms , alkenylthio of 2 to 6 carbon atoms, alkynylthio of 2 to 6 carbon atoms, haloalkylthio of 1 to 6 carbon atoms, halogenoalkenylthio of 2 to 6 carbon atoms, haloalkynylthio of 2 to 6 carbon atoms, cycloalkylthio of 3 to 8 carbon atoms, cycloalkenylthio of 4 to 8 carbon atoms, halogenocycloalkylthio of 3 to 8 carbon atoms, halogenocycloalkenylthio of 4 to 8 carbon atoms, alkylsulfinyl of 1 to 6 carbon atoms, alkenylsulfinyl of 2 to 6 carbon atoms, alkynylsulfinyl of 2 to 6 carbon atoms, haloalkylsulfinyl of 1 to 6 carbon atoms, halogenoalkenylsulfinyl of 2 to 6 carbon atoms, haloalkynylsulfinyl of 2 to 6 carbon atoms, cycloalkylsulfinyl of 3 to 8 carbon atoms, cycloalkenylsulfinyl of 4 to 8 carbon atoms, halogen-cycloalkylsulfinyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfinyl of 4 to 8 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms, alkynylsulfonyl of 2 to 6 carbon atoms , halogenoalkylsulfonyl of 1 to 6 carbon atoms, halogenoalkenylsulfonyl of 2 to 6 carbon atoms, halogenoalkynylsulfonyl of 2 to 6 carbon atoms, cycloalkylsulfonyl of 3 to 8 carbon atoms, cycloalkenylsulfonyl of 4 to 8 carbon atoms, halogenocycloalkylsulfonyl of 3 to 8 carbon atoms, halogenocycloalkenylsulfonyl of 4 to 8 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkenylamino of 2 to 6 carbon atoms, alkynylamino of 2 to 6 carbon atoms, haloalkylamino of 1 to 6 carbon atoms, halogenoalkenylamino of 2 to 6 carbon atoms, haloalkynylamino of 2 to 6 carbon atoms. cycloalkylamino of 3 to 8 carbon atoms, cycloalkenylamino from 4 to 8 carbon atoms, halogenocycloalkanogen of 3 to 8 carbon atoms, and halogenocycloalkenylamino of 4 to 8 carbon atoms, R1 is alkyl of 1 to 10 carbon atoms, haloalkyl, aryl, which is optionally substituted with one or more radicals of the group: halogen, cyano, nitro, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, amino, monoalkylamino of 1 to 4 carbon atoms, and dialkyl amino of 1 to 4 carbon atoms, NR102, OR10 or SR10; provided that the compounds mentioned below are not included: 3- (2-chlorophenyl) -1-methyl-5- (4-trifluoromethyl-3-pyridyl) -1H-1, 2,4-triazole, 3- (2,6-difluorophenyl) -1-methyl-5- (4-trifluoromethyl-3-pyridyl) -1 H-1, 2,4-triazole; 3- (2-chloro-4-fluorophenyl) -1-methyl-5- (4-trifluoromethyl-3-pyridyl) -1 H-1, 2,4-triazole; 3- (3,5-dichlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole, 5- (4-trifluoromethyl-3-pyridyl) -3-phenyl- 1, 2,4-oxadiazole, 3- (4-trifluoromethyl-3-pyridyl) -5-phenyl-1, 2,4-oxadiazole, 5- (2-chlorophenyl) -3- (4-trifluoromethyl) - 3-pyridyl) -1, 2,4-oxadiazole, 5- (3-chlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5- (4-chlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5- (2-fluorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, - (4-fluorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole, 5- (2,4-dichlorophenyl) -3- (4-trifluoromethyl-3-) pyridyl) -1, 2,4-oxadiazole, 5- (3,4-dichlorophenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 5- (3,5- dichlorophenol) -3- (4-trifluoromethyl-3-pyridyl) -1,4,4-oxadiazole, 5- (2,6-dichloro-4-pyridyl) -3- (4-trifluoromethyl-3-) pyridyl) -1, 2,4-oxadiazole, 5- (3,5-bstrifluoromethylphenyl) -3- (4-trifluoromethyl-3-pyridyl) -1, 2,4-oxadiazole, 2- (2-chlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1,4,4-oxadiazole, 2- (3-chlorophenyl) -5- (4-trifluoromethyl-3-pyra) idyl) -1, 3,4-oxadiazole, 2- (4-chlorophenyl) -5- (4-trifluoromethyl-3-pyridyl) -1, 3,4-oxadiazole, 2- (2-trifluoromethoxy-phenyl) -5 - (4-trifluoromethyl-3-pyridyl) -1,4,4-oxadiazole, 2- (4-trifluoromethoxyphenyl) -5- (4-trifluoromethyl-3-pyridyl) -1,4,4-oxadiazole, 2 - (4-trifluoromethyl-3-pyridyl) -5-phenyl-1, 3,4-oxadiazole, 2- (4-trifluoromethyl-3-pyridyl) -4-methylthiazolecarbohydrazide, 2- (4-trifluoromethyl- 3-pyridyl) -4-methylthiazolecarboxylic acid ethyl ester, N- (4-chlorophenyl) carbonyl-N '- [2- (4-trifluoromethyl-3-pyridyl) -4-methyl-5-thiazolyl] carbonylhydrazine, 2- (4 -trifluoromethyl-3-pyridyl) -4- thiazolcarbohydrazide, 4- (4-chlorophenyl) -2- (4-trifluoromethyl-3-pyridyl) -thiazole, 4- (4-cyanophenyl) -2- (4-trifluoromethyl) -3-pyridyl) -thiazole, N- (4-trifluoromethylphenyl) carbonyl-N '- [2- (4-trifluoromethyl-3-pyridyl) -4-thiazolyl] carbonylhydrazine, 2- (2- (4-trifluoromethyl-3 - pyridyl) thiazolyl) -5-chloro-3-methyl-benzo [b] thiophene, 2- (4-chlorophenylmethylthio) -5- (4-5 trifluoromethyl-3-pyridyl) -1-methyl-1H-1, 3,4-triazole, 2- (4-chlorophenylcarbonyl-methylthio) - 5- (4-trifluoromethyl-3-pyridyl) -1-methyl-1 H-1, 3,4-triazole; and 2-ethoxycarbonylmethylthio-5- (4-trifluoromethyl-3-pyridyl) -1-methyl-1H-1, 3,4-triazole.

2. A 4-halogenoalkyl-3-heterocyclylpyridine or 4-halogenoalkyl-5-heterocyclylpyrimidine according to claim 1, characterized in that Y is also alkyl of 1 to 6 carbon atoms, which is monosubstituted or polysubstituted with chlorine and / or fluorine; m is zero; Q is a heterocyclic group of five members where: a) X2 = NRa and X3 = CRbR1; or 15 b) X2 = CRaR2 and X3 = CRbR3; or c) X2 = CR4R5 and X3 = CR6R7; Ra and Rb together are a ligature; R1, R2, R3, R4 and R6, independently of one another, are hydrogen, halogen, alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, where the last four hydrocarbon radicals mentioned are optionally mono- or polysubstituted with identical or different radicals, of a group A1 consisting of: alkyl of 1 to 6 carbon atoms-carbonyl, alkylamino of 1 to 6 carbon atoms-carbonyl, al of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, ----- ^ gg ^^^^ - ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^? j ^^ j ^ ^^^^^^^^^^^^^^^^^^^^^^^^ j ^^^^^ alkylamino of 1 to 6 carbon atoms, alkylcarbonylamino of 1 to 6 carbon atoms, alkylsulfonylamino of 1 to 6 carbon atoms, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino; wherein the first eleven mentioned radicals of the group A1 are optionally mono- or polysubstituted, each having identical or different radicals, of a group B 1 consisting of halogen, cyano, al of 1 to 3 carbon atoms, and phenyl, which is mono - or optionally polysubstituted with one or more halogen atoms, and where the last three mentioned radicals of group A1 are each, optionally mono- or polysubstituted with identical or different radicals of a group B2 consisting of H, halogen, cyano, nitro, alkyl of 1 to 3 carbon atoms, and al of 1 to 3 carbon atoms, or are alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, alcarbonyl of 1 to 6 carbon atoms, phenyl, pyridyl, furyl, thienyl, pyrrhyl, where the last eight mentioned radicals are optionally mono- or polysubstituted with identical or different radicals from group B1, or are OR10, SR10 or N (R10) 2; each of R5 and R7, independently of each other, is hydrogen, halogen, alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 atoms carbon, where the last four mentioned hydrocarbon radicals are mono- or polysubstituted optionally with identical or different radicals, of a group A2 consisting of alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, al 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, alkylcarbonylamino of 1 to 6 carbon atoms, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino; where the first ten mentioned radicals of group A2 are optionally mono- or polysubstituted, each having identical or different radicals of group B1, and the last three mentioned radicals of group A2 are each optionally mono- or polysubstituted with identical or different radicals of group B2; or are alkylcarbonyl of 1 to 6 carbon atoms, alkylaminocarbonyl of 1 to 6 carbon atoms, alcarbonyl of 1 to 6 carbon atoms, phenyl, pyridyl, furyl, thienyl, pyrryl, where the last eight radicals mentioned are optionally mono- or polysubstituted with identical or different radicals of group B1, or are OR10, SR10 or N (R10) 2; R10 is hydrogen, benzyl, alkyl of 1 to 6 carbon atoms, cycloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, alkylcarbonyl of 1 to 6 carbon atoms, or alkylsulfonyl of 1 to 6 carbon atoms, where the last eight radicals mentioned are mono- or polysubstituted optionally with identical or different halogen atoms.

3. A 4-halogenoalkyl-3-heterocyclylpyridine or 4-halogenoalkyl-5-heterocyclipyrimidine according to claim 2, further characterized in that: Y is trifluoromethyl; R1, R2, R3, R4 and R6 are each independently, halogen, alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms, where the last two mentioned radicals are mono- or polysubstituted optionally with identical or different radicals of the group A3, consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, alkylsulfonylamino of 1 to 4 carbon atoms, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; where the first eleven mentioned radicals of the group A3 are each optionally mono- or polysubstituted with radicals identical or different from the group B1, and the last three mentioned radicals of the group A3 are each optionally mono- or polysubstituted with identical or different radicals of the group. group B2 or are OR10, SR10 or N (R10) 2; each of R5 and R7, independently of the other, is halogen, alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms, where the last two The mentioned radicals are optionally mono- or polysubstituted with identical or different radicals of an A4 group consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 20 4 carbon atoms, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; wherein the first ten radicals mentioned in group A4 are optionally mono- or polysubstituted, each with identical or different radicals of group B1; and the last three radicals The mentioned groups of group A4 are optionally mono- or polysubstituted with identical or different radicals from group B2, or are OR10, SR10 or N (R10) 2; R10 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, alkylcarbonyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms where the last six mentioned radicals are mono- or polysubstituted optionally with identical or different halogen atoms.

4. A 4-halogenoalkyl-3-heterocyclylpyridine or 4-halogenoalkyl-5-heterocyclylpyrimidine according to claim 3, further characterized in that each of R1, R2, R3, R4 and R6, independently of the others, is alkyl 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, where the last two mentioned radicals are mono- or polysubstituted optionally with identical or different radicals of a group A5 consisting of alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, alkylsulfonylamino of 1 to 4 atoms carbon, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; where the first eight mentioned radicals of group A5 are optionally mono- or polysubstituted, each with identical or different radicals of group B1 and the last three mentioned radicals of group A5 are optionally mono- or polysubstituted, each with identical or identical radicals different from group B2; each of R5 and R7, independently of the other, is alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, where the last two mentioned radicals are mono- or polysubstituted optionally with identical or different radicals from a group A6 consisting of: alkylcarbonyl of 1 to 4 carbon atoms, alkylaminocarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, alkylcarbonylamino of 1 to 4 carbon atoms, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino; wherein the first seven mentioned radicals of group A6 are optionally mono- or polysubstituted, each with identical or different radicals of group B1, and the last three mentioned radicals of group A6 are optionally mono- or polysubstituted, each with radicals identical or different from group B2.

5. A process for preparing compounds of the formula I, as claimed in any of claims 1 to 4, characterized in that it comprises: A) if X1 = O, X2 = NRa, X3 = CRbR1, react activated derivatives of the acid of the formula (II): where X and Y are as defined above, in the presence of a base, with a compound of the formula (III): wherein the radical R1 is as defined in the formula (I); or B) if X1 = S, X2 = NRa, X3 = CRbR1, react compounds of the formula (VII) with an electrophilic amination agent: (VII) (I) or C) if X1 = NRa, X2 = CRbR1, X3 = O, react amidoximes of the formula (V) with activated derivatives of acids of the formula (VI) or with the acids of the formula (SAW): (V) (VI) (I) or D) if X1 = S, X2 = CRaR1, X3 = NR, reacting N, N'-diacylhydrazines of the formula (XIII), with a thiolating agent, such as a reagent of Lawesson, in an inert solvent: (XIII) (i) or E) if X1 = O, X2 = CRaR1, X3 = NRb, reacting acids of the formula (II) with hydrazides of the formula (X), wherein R1 is as defined above, using an activating reagent , such as phosphorus oxychloride or phosphorus pentachloride: (M) (X) (I) or reacting acid hydrazides of the formula (XI) with orthoesters of the formula (XII), wherein R1 is as defined above and R12 is alkyl of 1 to 4 carbon atoms: (XI) (XII) (I) OF) if X1 = O, X2 = CRaR2, X3 = CRbR3, and Ra, Rb and R3 are as defined above, react compounds of the formula (XIV) with a dehydrating agent , such as inorganic acid chlorides, inorganic acids and anhydrides: (XIV) (I) OG) if X1 = S, X2 = CRaR2, X3 = CRbR3, react thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), in which Z is halogen, in particular chlorine or bromine, acyloxy or sulphonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy: (XVII) (XVIII) (l) Or H) if X1 = S, X2 = CR4R5, X3 = CR6R7, react thioamides of the formula (XVII) with compounds of the formula (XIX), where the two substituents Z are as defined hereinabove; and may be identical or different: (XVII) (XIX) (i) or I) if X1 = NRa, X2 = CRbR \ X3 = NR8 and Ra, Rb, R1 and R8 are as defined above, reacting hydrazides of the formula (XX): (XX) with a compound of the formula (XXI) or with thioamides of the formula (XXII): (XXI) (XXII)

6. - A composition having insecticidal, acaricidal and / or nematicidal action, characterized in that it comprises at least one compound as claimed in any of claims 1 to 4.

7. - A composition having insecticidal, acaricidal and nematicidal action, according to claim 6, further characterized in that it is mixed with carriers and / or surfactants.

8. A composition according to claim 6 or 7, further characterized in that it contains an additional active compound from the group of acaricides, fungicides, herbicides, insecticides, nematicides or growth regulating substances.

9. A compound according to any of claims 1 to 4, or a composition according to claim 6 or 7, further characterized by being used as a veterinary drug, preferably to control endoparasites and ectoparasites.

10. A method for controlling insects, mites and harmful nematodes, characterized in that it comprises: applying an effective amount of a compound according to any of claims 1 to 4, or of a composition as claimed in any of claims 6 to 8, to the area in which the action is desired.

11. A method for protecting plants useful against the undesirable action of insects, mites and harmful nematodes, characterized in that it comprises using at least one of the compounds claimed in any of claims 1 to 4, to treat the seed of useful plants .

12. The use of the compounds claimed in any of claims 1 to 4, or of a composition as claimed in any of claims 6 to 8, for controlling insects, mites and harmful nematodes.