MX2007006538A - Hydrazide compounds for combating animal pests. - Google Patents

Hydrazide compounds for combating animal pests.

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Publication number
MX2007006538A
MX2007006538A MX2007006538A MX2007006538A MX2007006538A MX 2007006538 A MX2007006538 A MX 2007006538A MX 2007006538 A MX2007006538 A MX 2007006538A MX 2007006538 A MX2007006538 A MX 2007006538A MX 2007006538 A MX2007006538 A MX 2007006538A
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Mexico
Prior art keywords
alkyl
haloalkyl
compounds
alkoxy
phenyl
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MX2007006538A
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Spanish (es)
Inventor
Michael Rack
Michael Hofmann
Deborah L Culbertson
David G Kuhn
Douglas Anspaugh
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Basf Ag
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Publication of MX2007006538A publication Critical patent/MX2007006538A/en

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/42—Hydrazines having nitrogen atoms of hydrazine groups further singly-bound to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

The present invention relates to new hydrazide compounds which are useful for combating animal pests, in particular insects, arachnids and nematodes and to the salts thereof. The invention also relates to a method for combating insects, nematodes and arachnids. The hydrazide compounds of the invention are described by the general formula (I) wherein ..a???? is absent or a covalent bond; A is an optionally substituted cyclic radical selected from phenyl, naphthyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, the 5- or 6-membered heterocyclic radical may have a carbonyl group as ring member; Q is selected from the group consisting of a single bond, C<sub>1</sub>-C<sub>4</sub> alkylidene, O-C<sub>1</sub>-C<sub>4</sub> alkylidene, S-C<sub>1</sub>-C<sub>4</sub> alkylidene and NR<sup>9</sup>-C<sub>1</sub>-C<sub>4</sub> alkylidene, wherein the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, =O, halogen, C<sub>1</sub>-C<sub>4</sub> haloalkyl and C<sub>1</sub>-C<sub>4</sub> alkoxy; or A-Q may together be C<sub>1</sub>-C<sub>10</sub>-alkyl, which may be substituted by 1 or 2 substituents selected from the group consisting of =O, OH, C<sub>1</sub>-C<sub>4</sub>-alkoxy, C<sub>1</sub>-C<sub>4</sub>-alkylthio, halogen or C<sub>1</sub>-C<sub>4</sub>-alkylcarbonyloxy, X is C=O, C=S or SO<sub>2</sub>; Ar is an optionally substituted aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl; and R<sup>1</sup> to R<sup>6</sup> and R<sup>9</sup> are as described in the claims and the specification.

Description

HIDRAZIDE COMPOUNDS FOR COMBATING ANIMAL PESTS The present invention relates to novel hydrazide compounds which are useful for combating animal pests, in particular insects, arachnids and nematodes. The invention also relates to a method for combating insects, nematodes and arachnids. Despite commercial pesticides currently available, damage to crops, cultivated and harvested, damage to inanimate material, particularly cellulose-based materials such as wood or paper, and other difficulties such as disease transmission, continue to occur. for animal pests.
JP 2000169461 describes, inter alia, thiadiazolylcarbonylhydrazones of phenylketones with insecticidal or fungicidal activity. However, the insecticidal activity of these compounds is not satisfactory. AM Islam et al., Egyptian Journal of Chemistry 1986, 29 (4) S. 405-431 (CASREACT 111: 173716) describes various naphthalin-2-yl sulfonylhydrazones of aromatic aldehydes, which were analyzed for cotton leafworms ( Spodoptera literalis). However, the activity of these compounds with respect to other pests is not satisfactory. Accordingly, there is a continuing need to provide compounds that are useful for combating insects, nematodes and arachnids. T. M. Temerk et al. Bull. Soc. Chim. Belg. 89 (7), 1980, p. 489-498 describes polarographic reduction according to the following scheme: International application PCT / EP 2004/005681 describes compounds of the general formula Ar - (CH2) n - Y - NH - N wherein Ar is an optionally substituted cyclic radical selected from phenyl, naphthyl and heterocyclic radicals, n is 0 or 1, Y is inter alia CO or S02, R1a is H, C1-C10 alkyl, C1-C10 haloalkyl, C3 cycloalkyl -C 10, C 3 -C 10 halocycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkenyl, C 2 -C 0 alkynyl, C 2 -C 0 haloalkynyl or optionally substituted phenyl, R 2a and R 3a are, inter alia, H, C 1 -C 10 alkyl , C1-C10 haloalkyl, halogen, phenyl or optionally substituted cyano and R4a are, inter alia, optionally substituted aromatic radicals selected from phenyl, pyridyl, pyrimidyl, furyl and thienyl. These compounds are active against insects and arachnids. It is an object of the present invention to provide compounds with good activity against insects, nematodes and / or arachnids and consequently are useful for combating said pests. The inventors of the present application surprisingly found that this object is achieved by compounds of the formula I as defined below and their salts. These compounds have not been described yet, except for a compound of the formula I, wherein A and Ar are unsubstituted phenyl, Q is a single bond, X is C = 0 and R1, R2, R3, R5 and R6 are hydrogen. Accordingly, the present invention relates to compounds of the general formula I and its salts, where it is absent or a covalent bond; A is a cyclic radical selected from phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members that are independently selected from O, N and S, the heterocyclic radical from 5 or 6. members may have a carbonyl group as ring member, and wherein the cyclic radical may have 1, 2, 3, 4 or 5 substituents Ra which are independently selected from halogen, cyano, nitro, alkyl C.- C10, C?-C10 haloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 halocycloalkyl, C 2 -C 0 alkenyl, C 2 -C 10 haloalkenyl, C 2 -C 0 alkynyl, C 3 -C 0 haloalkynyl, alkoxy haloalkoxy C? -C10, C2-C10 alkenyl-oxy, haloalkenyl C2-C? 0- oxy, C2-C10 alkynyloxy, haloalkynyl C3-C? 0-ox ?, alkyl C? -C10-t? o, haloalkyl C < - C 10 -thyle, C 1 -C 10 alkyl sulfinyl, C 1 -C 10 halo sulfyl, C 1 -C 0 alkylsulfonyl, C 1 -C 6 haloalkyl sulfonyl, hydroxy, NR 7 R 8 , C 1 -C 4 alkoxycarbonyl, C 1 -C 10 -carbonyl haloalkoxy, C 2 -C 10 alkenyl-oxocarbon;, C2-C6-haloalkenyl? -oxycarbonyl, C ^ C ^ alkylcarbonyl, C? -C10-haloalkylcarbonyl, R7R8N-CO-, phenyl, benzyl and phenoxy, in which phenyl, benzyl and phenoxy can be substituted with 1, 2, 3, 4 or 5 Rb substituents which are independently selected from halogen, cyano, nitro, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, C 3 -C 0 cycloalkyl, C 3 - halocycloalkyl C10, C2-C10 alkenyl, C2-C6 haloalkenyl, C2-C0 alkynyl, C3-C10 haloalkynyl, C1-C10 alkoxy, C? -C10 haloalkoxy, C2-C? Alkenyl? -ox ?, C2- haloalkenyl C10-ox ?, C2-C10 alkynyloxy, haloalkynyl C3-C? O-ox ?, alkyl C? -C? Ot? O, haloalkyl C? -C? Ot? O, alkyl C? -C10-suif Only one, haloalkyl C? -C10-sulphonyl, alkyl d-Cio-sulfonyl, haloalkyl C? -C10-sulphonyl, hydroxy, NR7R8, alkoxy C? -C? 0-carbonyl, haloalkoxy C? -C10-carbonyl, C2-C? alkoxy? o-oxycarbonyl, C2-C10 haloalkenyl-oxocarbonyl, alkyl CiC-io-carbonyl, haloalkyl d-Cio-carbonyl and R7R8N-CO-, in which in each case two Rad radicals that are n linked to adjacent carbon atoms can form a radical CH = CH-CH = CH or a radical 0 -CH2-0, where in these two radicals 1 or 2 hydrogen atoms can be replaced by a radical Rb as defined by Priority, Q is selected from the group consisting of a single bond, C1-C4 alkylidene, 0-alkylene C1-C4, S-C1-C4 alkylidene and NR9-alkyl C1-C4, that the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, = 0, halogen, C -? - C4 haloalkyl and C- | -C4 alkoxy, or the remainder AQ can be C-? - C-, 0 alkyl together, which can be substituted with 1 or 2 substituents selected from the group consisting of = 0, OH, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, halogen or alkyl C? -C4-carbon? lox ?, X is C = 0, C = S or S02, Ar is an aromatic radical selected from phenyl, naphthyl, pindyl, pinmidyl, funlo and thienyl, where the aromatic radical can carry 1, 2, 3, 4 or 5 substituyent is Rc which are selected, independently from each other, from halogen, cyano, nitro, d-do alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, alkynyl C2-C10, C3-C10 haloalkynyl, C1-C10 alkoxy, haloalkoxy d-Cio, C2-C alkenyl 0-oxy, C2-C10 alkynyl-oxy, haloalkynyl C3-C? 0-oxy, alkyl d-do-thio, haloalkyl C? -do-t Or, alkyl d-C10-sulfinyl, haloalkyl C1-C? 0-sulfinyl, alkyl dC? O-sulfonyl, haloalkyl d-C10-sulfonyl, hydroxy, NR7R8, alkoxy d-C10-carbonyl, haloalkoxy C? Carbon-carbonyl, C2-C-alkenyl-0-oxycarbonyl, C2-C10-haloalkenyl-oxycarbonyl, C1-C10-alkylcarbonyl, C?-C?-Haloalkyl or carbonyl, C alqu-C?-Alkylcarbonyloxy, R7R8N -CO-, phenyl, benzyl and phenoxy, in which phenyl, benzyl and phenoxy can be unsubstituted or can be substituted with 1, 2, 3, 4 or 5 substituents Rb as defined above and in which two radicals Rc which are attached to adjacent carbon atoms can form a 0-CH2-0 moiety, wherein in said moiety 1 or 2 hydrogen atoms can be replaced by a radical Rb as defined above; R1 is selected from the group consisting of H, alkyl d-dC haloalkyl d-C10, cycloalkyl C3-C10, halocycloalkyl C3-C0, alkenyl C2-C10, haloalkenyl C2-C? O, C2-C10 alkynyl, haloalkynyl C2- C10, phenyl and a heterocyclic radical of 5 or 6 members with 1 to 4 heteroatoms that are selected, independently of each other, of O, N and S, being possible for the last two radicals mentioned above not to be substituted or substituted with 1, 2, 3, 4 or 5 substituents Ra as defined above; R2 is a monovalent radical selected from H, halogen, cyano, C? -C10 alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl, haloalkynyl C3-C10, d-C10 alkoxy, C1-C10 haloalkoxy, C2-C? O-oxy alkenyl, C2-do-oxy haloalkenyl, C2-C10 alkynyl-oxy, C3-C10 haloalkynyl-oxy, C? -C alkyl o-thio, haloalkyl d-C10-thio, hydroxy-d-C10 alkyl, d-Cio alkoxy-d-C10 alkyl, halo-d-C10 alkoxy-C? -C10 alkyl, alkoxy dC? o -carbonyl-alk D-C10, haloalkoxy d-C10-carbonyl-d-C10 alkyl and phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents Rb as defined above; R3 is selected from the group consisting of H, halogen, cyano, C? -C10 alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C6 haloalkenyl, C2- alkynyl? C? 0, C3-C10 haloalkynyl, C? -C10 alkoxy, C1-C10 haloalkoxy, C2-C? O-oxy alkenyl, C2-do-oxy haloalkenyl, C2-C? Alkynyloxy, C3-C10 haloalkynyl? oxy, alkyl dC? oti, haloalkyl d-do-thio, hydroxyalkyl dC? 0, alkoxy d-Cio-alkyl dC? 0, halo-alkoxy d-Cio-alkyi dC? 0, alkoxy d-Cio-carbonyl-d-C10 alkyl, haloalkoxy d-Cio-carbonyl-d-C10 alkyl and phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents Rb as defined above; R4 is hydrogen or has one of the meanings given for Rc or R4 together with R2 is a bivalent radical Y, which is selected from O, S, CR10 = N, N = N, 0-CR1 R12, S-CR11R12, N (R13) -CR1 R12, O-C (O), O-C (S), S-C (O); N (R13) -C (0) or N (R3) -C (S); R5 is selected from the group consisting of H, d-C10 alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C6 haloalkenyl, C2-C10 alkynyl, haloalkynyl C2 -C? 0, benzyl and phenyl, where benzyl and phenyl may be substituted with 1, 2, 3, 4 or 5 substituents Rd which are independently selected from halogen, cyano, nitro, d-C10 alkyl, haloalkyl d-C10, cycloalkyl C3-C0, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C10, alkynyl C2-C? 0, haloalquinil C3-C10, alkoxy C10, haloalkoxy d-C10, alkenyl C2 -C10-oxy, C2-C10-haloalkenyl-oxy, C2-C10-alkynyl-oxy, C3-C10-haloalkynyl-oxy, alkyl d-C10-thio, haloalkyl d-C10-thio, alkyl CT-CTO-sulfinyl, haloalkyl d- do-sulfinyl, d-C10-alkylsulfonyl, haloalkyl-d-do-sulfonyl, hydroxy, NR7R8, C? -C? alkoxycarbonyl, haloalkoxy d-C10-carbonyl, C2-C? alkenyl? -oxycarbonyl, haloalkenyl C2 -C10-oxycarbonyl, alkyl d-do-carbonyl, halo l-d-C10-carbonyl and R7R8N-C0-; R6 is selected from the group consisting of H, d-C10 alkyl optionally substituted by CN or N02, haloalkyl d-C10, cycloalkyl C3-C? Or, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C10, alkynyl C2 -C10, C2-C10 haloalkynyl, d-C10 alkyl thio, d-C10 haloalkyl thio, d-C10 alkyl sulfinyl, haloalkyl d-do sulfinyl, C? -C? Alkyl or sulfonyl, haloalkyl d-do -sulfonyl, d-doxycarbonyl, haloalkoxy d-Cio-carbonyl, C2-C-alkenyl-0-oxycarbonyl, haloalkenyl-C2-C-0-oxycarbonyl, alkyl d-do-carbonyl, where the alkyl residue of alkylcarbonyl may not is substituted or can be substituted with 1, 2 or 3 substituents selected from the group consisting of alkyl d-C10-thio, phenylthio, phenyl and phenoxy, haloalkyl d-do-carbonyl, C2-C? alkenyl? -carbonyl, hydroxyalkyl d -dc alkoxy d-do-alkyl d-C10, halo-alkoxy d-C10-alkyl d-Cio, alkoxy d-do-carbonyl-d-C10 alkyl, halo-alkoxy dC? 0-carbonyl-d-C10 alkyl, R7R8N-CO-, benzoyl (C6H5-CO-), cycloalkyl C3-C1 0-carbonyl, R6a-CO-, wherein R6a is d-C4-alkoxycarbonyl, phenoxy, naphthyl or a heterocyclic radical of 5 or 6 members with 1 to 4 heteroatoms that are selected, independently of each other, of O, N and S, being possible for phenoxy, naphthyl and the 5 or 6 membered heterocyclic radical not being substituted or substituted with 1 , 2, 3, 4 or 5 substituents Ra as defined above, and benzyl wherein benzyl may be substituted with 1, 2, 3, 4 or 5 substituents Rb as defined above; R7, R8 are independently selected from H, alkyl dCyclohaloalkyl d-C10, cycloalkyl C3-C0, halocycloalkyl C3-C10, alkenyl C2-C? O, haloalkenyl C2-C10, alkynyl C2- C? 0, C3-C10 haloalkynyl, phenyl, benzoyl, naphthyl or benzyl wherein the phenyl ring in the above-mentioned four radicals can be substituted with 1, 2, 3, 4 or 5 substituents which are selected, independently of each other , of halogen, cyano, nitro, C1-C10 alkyl, haloalkyl dC 0, cycloalkyl C3-C10, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C10, alkoxy C1-C10, haloalkoxy d-C10, alkyl C? -C10-thio, haloalkyl d-C10-tio, alkylC? -C10-sulfonyl, haloalkyl C? -C10-sulfonyl, hydroxy, alkoxy d-do-carbonyl, haloalkoxy d-C10-carbonyl, alkenyl C2-C ? 0- oxycarbonyl, C2-C10 haloalkenyl-oxycarbonyl, d-Cio-carbonyl alkyl and C? -C10 haloalkylcarbonyl; R9 is hydrogen, cyano, d-C10 alkyl, haloalkyl d-C10, cycloalkyl C3-C10, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C? 0, alkynyl C2-C? 0, haloalquinilo C3-C10, haloalkyl d-Cio-sulfonyl, alkyl d-Cio-carbonyl, haloalkyl C? -C? or -carbonyl, R7R8N-CO-, phenyl or benzyl, in which phenyl and benzyl can be substituted with 1, 2, 3, 4 or 5 Rb substituents; and R10 is hydrogen or has one of the meanings given for Rc; R11, R12 are selected, independently from each other, from H, d-C10 alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl and haloalkynyl C3-C10, alkoxy d-C10, haloalkoxy d-Cic alkyl d-C10-thio, haloalkyl d-do-thio, hydroxy-C1-C10 alkyl, alkoxy d-Cio-alkyl d-d0, halo-alkoxy d- d-C10-alkyl, C1-C10-alkoxy-carbonyl-d-C10-alkyl, halo-C0-C6-alkoxy-carbonyl-d-C10 alkyl, one of the radicals R11 or R12 can also be alkyl d-C10 -sulfonyl, haloalkyl d-Cysulfonyl, d-C10 alkoxycarbonyl, d-C10 haloalkoxycarbonyl, C2-C10 alkenyl-oxycarbonyl, C2-C10 haloalkenyl-oxycarbonyl, C? -C10 alkylcarbonyl, haloalkyl d-Cio -carbonyl or R7R8N-CO-, R13 is hydrogen, cyano, d-C10 alkyl, haloalkyl d-dC C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C20 alkynyl, C3-C10 haloalkynyl, haloalkyl C? -C? 0-sulfonyl, C alqu?-C? 0-carbonyl alkyl, d-C 10 -haloalkylcarbonyl, R 7 R 8 N -CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted with 1, 2, 3, 4 0 5 substituents Rb; except for a compound of formula I, in which A and Ar are unsubstituted phenyl, Q is a single bond, X is C = 0 and R1, R2, R3, R5 and R6 are hydrogen. Due to their excellent activity, the compounds of the general formula I can be used to control pests, selected from insects, arachnids and harmful nematodes. The compounds of the formula I are useful in particular for controlling insects. Accordingly, the invention also provides compositions for combating said pests, preferably in the form of solutions, emulsions, pastes, oily dispersions, powders, dispersion materials, directly sprayable or granular powders, comprising an amount of efficacy pesticide of at least one compound of the general formula I or at least one of its salts and at least one carrier which can be liquid and / or solid and which is preferably acceptable in agriculture and / or at least one surfactant. On the other hand, the invention provides a method for combating such pests, which comprises contacting said pests, their habitat, nutrient soil, food supply, plant, seed, soil, area, material or environment where the animal pests grow or can grow, or the materials or materials, plants, seeds, soils, surfaces or spaces to be protected from an attack or infestation of said pest with a pesticidally effective amount of a compound of the general formula I as defined herein or one of its salts. The invention provides in particular a method for protecting crops, including seeds, from attack or infestation by harmful insects, arachnids and / or nematodes, comprising contacting a crop with a pesticidally effective amount of at least one compound of the formula I as defined herein or with one of its salts. The invention also provides a method for protecting inanimate materials from attack or infestation by the aforementioned pests, which comprises contacting the inanimate material with a pesticidally effective amount of at least one compound of the formula I as defined in present or with one of its salts.
Suitable compounds of the general formula I include all possible stereoisomers (cis / trans isomers, enantiomers) that can be present and their mixtures. The stereoisomeric centers are, for example, the carbon atom of group C (R2) = C (R3) and the remainder C (R1). The present invention provides both the enantiomers and the pure diastereomers or mixtures thereof, the pure cis and trans isomers and mixtures thereof. The compounds of the general formula I can also exist in the form of different tautomers if A or Ar carry amino or hydroxy groups. The invention comprises the individual tautomers, if separable, as well as the tautomeric mixtures. The salts of the compounds of the formula I are preferably preferable salts in agriculture. They can be formed in a conventional method, for example, by reacting the compound with an acid of the anion in question when the compound of formula I has a basic functionality or by reaction with an acidic compound of formula I with an appropriate base. Suitable salts useful in agriculture include the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have an adverse effect on the action of the compounds according to the present invention. Suitable cations are, in particular, the alkali metal ions, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4 +) and substituted ammonium, wherein one to four of the hydrogen atoms are replaced by C 1 -C 4 alkyl, d-C 4 hydroxyalkyl, d-C 4 alkoxy, C 1 -C 4 alkoxy alkyl, hydroxy C 1 -C 4 alkyl alkoxy d-C 4, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium,. isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy) ethylammonium, bis (2-hydroxyethyl) ammonium, benzyltrimethylammonium and benzyltriethylammonium, also phosphonium ions, sulfonium ions, preferably tri ( alkyl d-C4) sulfonyl, and sulfoxonium ions, preferably tri (alkyl Ci-) sulfoxonium. The anions of salts by addition of useful acids are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of alkanoic acids dC, with Formate, acetate, propionate and butyrate preference. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. The organic residues mentioned in the above definitions of the variables are -as the term halogen- collective terms for individual lists of members of the individual group. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group. "Halogen" or "halo" is fluorine, chlorine, bromine and iodine. The term "alkylidene dd" refers to a linear or branched alkanediyl group having 1 to 4 carbon atoms such as methylene (= CH2), 1,2-ethanediyl (= CH2CH2), 1, 1-ethanediyl (= CH (CH3) ), 1,2-propandiyl, 1,3-propandiyl, 2,2-propandiyl, 1,4-butanediyl and the like. According to the invention, alkanoyl dC4 is unsubstituted or can carry 1, 2, 3 or 4 substituents selected from OH, = 0, halogen C? -Chaloalkyl and alkoxy d-C4. The substituent = 0 denotes a carbonyl group. The terms "O-C1-C4 alkylidene" and "S-C1-C4 alkylidene", respectively, refers to a linear or branched alkanediyl group having 1 to 4 carbon atoms, wherein a valence is attached to the skeleton by means of an oxygen or sulfur atom, respectively. The term "C 1 -C 10 alkyl" as used herein (and also in C 1 -C 10 alkyl-sulfinyl and alkyl d-do-sulfonyl) refers to a branched or unbranched saturated hydrocarbon group having 1 to 10 atoms carbon, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1,2-trimethylpropyl, 1-ethyl- 1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C 1 -C 4 alkyl means, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl. The term "haloalkyl d-C? 0" "as used herein (and also in haloalkyl d-doxylsulfinyl and haloalkyl C?-C? Or sulfonyl) refers to an alkyl group straight or branched chain having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example, haloalkyl d-C4, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, , 2,2-thluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term haloalkyl d-C10 comprises in particular C? -C2 fluoroalkyl, which is synonymous with methyl or ethyl, where 1, 2, 3, 4 or 5 hydrogen atoms are substituted with fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl , 1-f luoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl. Similarly, "alkoxy d-Cio" and "alkyl d-do-thio" refer to straight or branched chain alkyl groups having 1 to 10 carbon atoms (as mentioned above) bound through ligations of oxygen or sulfur, respectively, at any position in the alkyl group. Examples include C 1 -C 4 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, also alkyl d-C 4 -thi such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio. Accordingly, the terms "haloalkoxy d-C10" and "haloalkyl d-Cio-thio" refer to straight or branched chain alkyl groups having 1 to 10 carbon atoms (as mentioned above) attached through of oxygen or sulfur ligations, respectively, at any position in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example, haloalkoxy C -? - C2, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2.2, 2-thluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, further haloalkyl d-C2-thio, such as chloromethylthio, bromomethylthio, dichloromethylthio, triclo romethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like. Similarly, the terms fluoroalkoxy C? -C2 and fluoroalkyl C? -C -thio refer to fluoroalkyl C? -C which is attached to the rest of the molecule through an oxygen or sulfur atom, respectively. The term "C2-C10 alkenyl" as used herein comprises a linear or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond at any position, such as ethenyl, 1-propenyl, 2- propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl- 2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-J-dimethyl-2 -propene, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, -hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1-pentenyl, 4-metii-1 -pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2 -methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl--pentenyl, 4- methyl-4-pentenyl, 1 J-dimethyl-2-butenyl, 1 J-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl- 3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl- 1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1- ethyl- 1- butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 J, 2-trimethyl-2 -propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl. The term "C2-C10 haloalkenyl" as used herein includes a linear or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond at any position, where some or all of the hydrogen atoms in these groups they can be replaced by halogen atoms as mentioned above. Similarly, the term "C2-C10 alkenyl-oxy" as used herein includes a linear or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the group being attached alkenyl through an oxygen ligation, at any position in the alkenyl group, for example, ethenyloxy, propenyloxy and the like Accordingly, the term "haloalkenyl C2-do-ox?" as used herein includes a linear or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond at any position, being attached to the alkenyl group through an oxygen ligation, at any position in the group alkenyl, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above The term "C2-C10 alkynyl" as used herein refers to a linear or branched saturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1- butyl, 2-butynyl, and the like The term "C3-C10 haloalkynyl" as used herein refers to a linear or branched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least a triple bond, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound with the triple bond The term "alkynyl" C2-C10-ox? " as used herein refers to a linear or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, the alkynyl group being linked through an oxygen ligation at any position in the alkynyl group. Similarly, the term "C3-C10 haloalkynyl-ox." as used herein refers to a linear or branched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, the group being linked through oxygen ligations at any position in the group alkynyl, where some or all of the hydrogen atoms in this group may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bonded to the triple bond The term "C3-cycloalkyl" C10"as used herein refers to a 3 to 10 membered monocyclic saturated carbon atom ring, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, oclooctyl and cyclodecyl.
The term "C3-C10 halocycloalkyl" as used herein refers to a 3 to 10 membered monocyclic saturated carbon atom ring, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example, chloro-, dichloro- and trichlorocyclopropyl, fluoro-, difluor- and trifluorocyclopropyl, chloro-, dichloro-, trichloro , tetrachloro-, pentachloro- and hexachlorocyclohexyl and the like.
The term "C alqu-C?-Alkylcarbonyl" as used herein refers to alkyl -Cio which is attached to the rest of the molecule through a carbonyl group. Examples include CO-CH3, CO-C2H5, CO-CH2-C2H5, CO-CH (CH3) 2, n-butylcarbonyl, CO-CH (CH3) -C2H5, CO-CH2-CH (CH3) 2, CO- C (CH 3) 3, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1- methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1-trimethylpropylcarbonyl, 1, 2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl. The term "C 1 -C 6 alkoxycarbonyl" as used herein refers to alkoxy d-do which is attached to the rest of the molecule through a carbonyl group. Examples include CO-OCH3, CO-OC2H5, CO-OCH2-C2H5, CO-OCH (CH3) 2, n-butoxycarbonyl, CO-OCH (CH3) -C2H5, CO-OCH2-CH (CH3) 2, CO-OC (CH3) 3, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1-J-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, -methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1-J-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1, 2-trimethylpropoxycarbonyl, 1, 2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl.
The term "haloalkoxy C? -C10-carbonyl" as used herein refers to haloalkoxy -Cio which is attached to the rest of the molecule through a carbonyl group. The terms "hydroxy-C C-C 0 alkyl", "d-C 10 alkoxy-C?-C10 alkyl", "halo-d-alkoxy d-do-d-C alquilo alkyl", "d-dicarboxylalkyl-d alkoxy" -C10"," halo-alkoxyC? -C? O-carbonyl-C? -C10 alkyl "as used herein, refer to d-C10 alkyl, as defined herein, in particular to methyl, ethyl, 1- propyl or 2-propyl, which is substituted with a radical selected from hydroxy, d-C10 alkoxy, haloalkoxy d-Cio, d-C10-alkoxycarbonyl or d-C10 haloalkoxycarbonyl. The term "5- or 6-membered heterocyclic radical with 1, 2, 3 or 4 heteroatoms which are independently selected from O, N and S" comprises 5 or 6 membered monocyclic heteroaromatic rings and saturated non-aromatic monoheterocycles. or partially unsaturated of 5 or 6 members bearing 1, 2, 3 or 4 heteroatoms as ring members. The heterocyclic radical can be attached to the rest of the molecule through a carbon ring member or through a nitrogen ring member. Examples of non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxoleyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl. , oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like. Examples of 5- to 6-membered monocyclic heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl. With respect to the use according to the invention of the compounds of the formula I, particular preference is given to the following meanings of the substituents, in each case by themselves or in combination: Preference is given to the compounds of the formula I, in wherein A in formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl and wherein the cyclic radical may be unsubstituted or it can be substituted as it is described earlier. In particular, the aforementioned radicals are unsubstituted or substituted by 1, 2 or 3 radicals Ra as defined above. Preferred Ra radicals comprise halogen, CN, d-C4 alkyl, d-C4 alkoxy, haloalkoxy C1-C4, alkyl d-C4-thio and haloalkyl d-C4, in particular F, Cl, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. More preference is given to the compounds of the formula I, wherein A is a cyclic radical selected from phenyl, thienyl, furyl, isoxazolyl, pyrazolyl, imidazolyl, pyrazinyl, pyrimidinyl and pyridyl, in particular pyridyl, thienyl and phenyl, wherein the cyclic radical may be substituted with 1, 2 or 3 substituents Ra which are as defined above and which are preferably independently selected from halogen, Ci-d alkyl, C1-C4 alkoxy, haloalkoxy d-C4, alkyl dd-thio and C-α-C4 haloalkyl, in particular of F, Cl, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. Examples of preferred A radicals include: 2-thienyl, 3-bromothien-2-yl, 4-bromothien-2-yl, 5-bromothien-2-yl, 4,5-dibromothien-2-yl, 3-chlorothien- 2-yl, 4-chlorothien-2-yl, 5-chlorothien-2-yl, 3-chloro-methylthien-2-yl, 3-methylthien-2-yl, 4-Methylthien-2-yl, 5-methylthien-2-yl, 3-methoxy-thien-2-yl, 3-methoxy-5- (trifluoromethyl) thien-2-yl, 3-ethoxy-5- (trifluoromethyl) thien -2-yl, 2-bromo-, 5-dimethylthien-2-yl, pyridin-2-yl, 6-methylthiopyridin-2-yl, 3-fluoropyridin-2-yl, 3-methoxypyridin-2-yl, 6- methylpyridin-2-yl, 5-nitropyridin-2-yl, 3-fluoropyridin-2-yl, 6-bromopyridin-2-yl, 6-chloropyridin-2-yl, 4-chloropyridin-2-yl, 3,6- dichloropyridin-2-yl, 6-fluoropyridin-2-yl, 5- (trifluoromethyl) pyridin-2-yl, 4- (trifluoromethyl) pyridin-2-yl, 6- (trifluoromethyl) pyridin-2-yl, 6-hydroxypyridin-2-yl, 6-methoxypyridin-2-yl, 3-hydroxypyridin-2-yl, 6-phenylpyridin-2-yl, pyridin-3-yl, 6-chloropyridin-3-yl, 2.6 - dichloropyridin-3-yl, 5,6-dichloropyridin-3-yl, 2,6-dichloro-4-methylpyridin-3-yl, 6-fluoropyridin-3-yl, 6-bromopyridin-3-yl, 5-bromopyridin -3-yl, 2-phenoxypyridin-3-yl, 1- et il- 2-hydroxypyridin-3-yl, pyridin-4-yl, 2-chloropyridin-4-yl, 2,6-dichloropyridin-4-yl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2, 4-difluorophenyl, 2,5-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro- 6-fluorophenyl, 2-chloro- 4- fluorophenyl, 1, 2,3,4,5-pentafluorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 5-bromo-2-chlorophenyl, 4-chloro-2-methylphenyl, 3-fluoro-4- methylphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 2- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 4- (trifluoromethyl) phenyl, 2-fluoro-4- (trifluoromethyl) phenyl, 3,5-bis (trifluoromethyl) phenyl, 4- tert.-utilphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methoxy-3- (methylthio) phenyl, 2-nitrophenyl, 3 -nitrophenyl, 4-nitrophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-hydroxy-3-methoxyphenyl, 2-fluoro-4-hydroxyphenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 6-amino -2-fluorophenyl, 4- (dimethylamino) phenyl, 4-phenylphenyl, 4- (methylsulfonyl) -2-nitrophenyl, 5-methylpyrazin-2-yl, 3-aminopyrazin-2-yl, 2- furyl, 5-bromofuran- 2-yl, 2-methylfuran-3-yl, 5-isoxazolyl, 3-methylisoxazolyl, 3- (1-methylethyl) isoxazolyl, 5- (chloromethyl) isoxazolyl, 5- (hydroxymethyl) isoxazolyl, 1,3-bis (1 , 1,1-trifluoroet-2-yl) pyrazol-4-yl, 1-methyl-3- (trifluoromethyl) pyrazol-5-yl, 3-methylimidazol-2-yl, 4-methylimididazol-5-yl, -4 -amino-2-methylpyrimidin-2-yl, 6-hydroxy-2-methylpyrimidin-4-yl, The cyclic radical can also be naphthyl, 1, 2,3,4-tetrahydroisoquinolin-3-yl, 2-benzothienyl, benzo [1 , 3] - dioxol-5-yl, indolyl or benzimidazolyl, wherein the cyclic radical may be unsubstituted or may be substituted as described above. In particular, the aforementioned radicals are unsubstituted or substituted by 1, 2 or 3 radicals Ra as defined above. Examples of these radicals A include: - 3-hydroxynaphth-2-yl, 2-benzothienyl, 3-chloro-2-benzothienyl, 1-naphthyl, 2-naphthyl, 3- indolyl, 2-benzimidazolyl, 6,7-dimethoxy -3-methyl-1, 2,3,4-tetrahydroisoquinolinyl. Another embodiment of the invention relates to compounds of the formula I in which A is a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members that are selected, independently of each other, from O, N and S and may also have a carbonyl group as ring member, and may have 1, 2, 3, 4 or 5 substituents Ra as defined above. A very preferred embodiment of the invention relates to compounds of the formula I, wherein A is thienyl, in particular 2-thienyl which is unsubstituted or which is substituted with 1, 2 or 3 radicals Ra as defined above, the radicals Ra being preferably selected, independently of each other, from halogen, d-C4 alkyl, d-C4 alkoxy, alkyl d-C4-thio , haloalkoxy C1-C4 and haloalkyl d-C4, in particular of F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. Another embodiment of the invention of very special preference refers to compounds of the formula I, wherein A is furyl, in particular 2-furyl which is unsubstituted or which is substituted by 1, 2 or 3 Ra radicals such as it was previously defined, the radicals Ra being preferably selected, independently of each other, from halogen, C?-C 4 alkyl, C?-C 4 alkoxy, dι-C 4 -alkyloxy, haloalkoxy d-C 4 and haloalkyl C- C 4, in particular F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. Another embodiment of the invention of very special preference relates to compounds of the formula I, in which A is pyridyl, in particular 2- or 3-pyridyl, more preferably 2-pyridyl, which is unsubstituted or which is substituted with 1, 2 or 3 radicals Ra as defined above, the radicals Ra being preferably selected, independently of each other, from halogen, dC alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloalkoxy d-C4 and haloalkyl d-C4, in particular of F, Cl, Br, methyl, methoxy, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. Another very special embodiment of the invention relates to compounds of the formula I, in which A is phenyl, which is unsubstituted or is substituted by 1, 2 or 3 radicals Ra as defined above, the radicals R a being preferably selected, independently of one another, from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C haloalkoxy, C 1 -C 4 alkyl-thio, and d-C 4 haloalkyl, in particular from F , Cl, Br, methyl, methoxy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, trifluoromethoxy and difluoromethoxy. X is preferably C = 0. Q is preferably selected from the group consisting of a single bond, -CH2-, -CH2-CH2-, -0-CH2-, -0-CH2-CH2-, 0-CH2-CH2-CH2-, -NH-CH2 - CH2-, -NH-C (0) -CH2-, -S-CH2-, -S-CH2-CH2-, -0-CH (CH3) - and -S-CH (CH3) -, in particular from a simple bond, -CH2-, -0-CH2-, -S-CH2-, -0-CH (CH3) - and -S- CH (CH3) -. The heteroatom of Q is preferably linked to A. More preferably, Q is a single bond or -CH2- Preference is also given to compounds of formula I, wherein the AQ moiety is d-C10 alkyl, which may be substituted with 1 or 2 substituents selected from the group consisting of = 0, OH, C? -C4 alkoxy, C 1 -C 4 -thio alkyl, halogen or alkyl dd-carbonyloxy, in particular de = 0, OH and C 1 -C 2 alkoxy. Preferred examples of the AQ moiety include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, 4-hydroxybutyl, 5-hydroxypentyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl , methoxycarbonylmethyl or ethoxycarbonylmethyl, especially methyl. In one embodiment of this invention, R1 is H, d-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C20 alkynyl and haloalkynyl C2-C10. In this embodiment, R 1 is preferably hydrogen, d-C 10 alkyl, d-C 10 haloalkyl, more preferably hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, and especially hydrogen. In another embodiment of this invention, R1 is selected from the group consisting of phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are independently selected from O, N and S, being possible for phenyl and the 5- or 6-membered heterocyclic radical are unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Ra as defined above. In this embodiment, preference is given to compounds I, in which R1 is pyridyl, in particular 3-pyridyl, C3-C10 cycloalkyl, phenyl and more preferably C3-C6 cyclopropyl, R2 is preferably selected from hydrogen, halogen and C 1 -C 4 alkyl, in particular hydrogen, fluorine, chlorine, bromine, methyl or ethyl. R 3 is preferably selected from hydrogen, halogen and C 1 -C 4 alkyl, preferring more to hydrogen. R 5 is preferably selected from hydrogen, C-C 10 alkyl, haloalkyl d-do, C 3 -C 0 cycloalkyl, C 3 -C 0 halocycloalkyl, C 2 -C 10 alkenyl, C 2 -C 9 haloalkenyl, in particular hydrogen and C 1 -C 6 alkyl. -C4. In another embodiment, R6 is selected from the group consisting of H, alkyl d-do, which is optionally substituted with CN or N02, haloalkyl d-C10, cycloalkyl C3-C10, halocycloalkyl C3-C10, alkenyl C2-C10, C2-C10 haloalkenyl, C2-C2 alkynyl, C2-C10 haloalkynyl, d-C10 alkyl sulfinyl, haloalkyl dC0- sulfinyl, alkyl d-do-sulfonyl, haloalkyl C? -C? o -sulfonyl, alkoxy C ? -C? -carbonyl, haloalkoxy C? -C10-carbonyl, C2-C? Alkenyl? -oxycarbonyl, haloalkenyl d-Cioxycarbonyl, alkyl d-Cio-carbonyl, haloalkyl C? -C? Or -carbonyl, hydroxy -C1 alkyl- Cio, C 1 -C 10 alkoxy-d-do alkyl, halo-d-C 10 alkoxy-d-C 10 alkyl, d-C 10 alkoxy-carbonyl-C 1 -C 10 alkyl, halo-d-C 10 alkoxycarbonyl-d-C 10 alkyl , R7R8N-CO- and benzyl in which benzyl can be substituted with 1, 2, 3, 4 or 5 substituents Rb as defined above. In this embodiment, R6 is preferably hydrogen, C1-C4 alkyl, d-C4 haloalkyl, C?-C4-sulfonyl alkyl, d-C4 alkylcarbonyl, C?-C 4 alkyl sulfonyl or haloalkyl d -C 4 sulfonyl It, in particular hydrogen.
Preference is also given to the compounds of the formula I, wherein R6 is C 1 -C 0 alkyl-thio, haloalkyl d-do-thio, alkyl d-C 10 -carbonyl, where the alkyl moiety of the alkylcarbonyl is substituted with 1, 2 or 3 substituents selected from the group consisting of C 1 -C 0 alkyl-thio, phenylthio, phenyl and phenoxy, C 2 -C 10 alkenyl-carbonyl, benzoyl (C 6 H 5 -CO-), C 3 -C 10 cycloalkyl-carbonyl , R6a-CO-, in which R6a is alkoxy dC -carbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of each other, from O, N and S, it being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Ra as defined above. In this embodiment, R6 is preferably C 1 -C 4 -carbonyl alkyl, wherein the alkyl moiety of the alkylcarbonyl is substituted with a radical selected from phenyl, alkyl d-C4-thio, phenylthio and phenoxy, such as phenoxymethylcarbonyl, 2-methylsulfanylethylcarbonyl and phenylsulfanylmethylcarbonyl or benzoyl. Preference is also given to compounds of the formula I, wherein R6 is a benzoyl or a radical of the formula R5a-C (0) -, wherein R6a is d-C2-carbonyl alkoxy, phenoxy, a heterocyclic radical 5 or 6-membered aromatic with 1 or 2 heteroatoms that are independently selected from O, N and S, being possible for the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted with 1 or 2 substituents Ra as defined previously. Examples of preferred R6a radicals are phenoxy, 3-isoxazolyl, 5-isoxazolyl, 2-thienyl and 2-furyl and methoxycarbonyl. Ar is preferably phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4, in particular 1, 2 or 3 Rc radicals as defined above. One skilled in the art will appreciate that, in the case of R4 being different from hydrogen, R4 is one of the 1 to 4 radicals Rc as defined above or R4 together with R2 is the above-mentioned bivalent radical. Another embodiment of the invention relates to compounds I, in which Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl and wherein two Rc radicals that are bonded to adjacent carbon atoms can form a 0-CH2-0 moiety, wherein in said moiety 1 or 2 hydrogen atoms can be replaced by an R radical as defined above. In one embodiment, the radical Rc is halogen, cyano, nitro, alkyl d- or haloalkyl d-C10, cycloalkyl C3-C? 0, halocycloalkyl C3-C0, alkenyl C2-C10, haloalkenyl C2-C? 0 , C2-C? alqu alkynyl, C3-C10 haloalkynyl, d-do alkoxy, haloalkoxy d-do, C2-C?? alkynyl-oxy, C2-C alqu alkynyl-oxy, haloalkynyl C3-C? 0-oxy, alkyl d-do-thio, haloalkyl C? -C? 0-thio, alkyl C? -C10-sulfinyl, haloalkyl C? -C10-sulfinyl, alkyl d-C10-sulfonyl, haloalkyl d-do-sulfonyl, hydroxy, NR7R8 , alkoxy d-do-carbonyl, haloalkoxy dC? o-carbonyl, C2-C10 alkenyl-oxycarbonyl, haloalkenyl C2-C0-oxycarbonyl, alkyl d-C10-carbonyl, haloalkyl d-do-carbonyl, R7R8N-CO- , phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be unsubstituted or may be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above. Preferably, the radicals Rc are selected, independently of one another, from halogen, CN, d-C4 alkyl, C1-C alkoxy, d-C4 haloalkoxy and C? -C4 haloalkyl, more preferably F, Cl, CN, d-C3-alkoxy, in particular methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy and methyl. In another embodiment, the radical Rc is C 1 -C 4 alkyl or carbonyl. Another very special embodiment of the invention relates to compounds of the formula I, in which Ar is furyl, in particular 2-furyl which is unsubstituted or substituted by 1 radical Rc as defined above or thienyl, in particular 2-thienyl, which may be unsubstituted or which may be substituted with 1 radical Rc as defined above. In a preferred embodiment of the invention, the radical R2 in the formula I is a monovalent radical, ie R2 and R4 together do not form a bivalent radical. In this embodiment, R 2 is preferably selected from hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 haloalkyl. More preferably, R2 is hydrogen, fluorine, chlorine, bromine, methyl or ethyl. In this embodiment, R4 is hydrogen or a radical Rc as defined above, in particular hydrogen. In this embodiment, Ar in the formula I is preferably phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4, in particular 1, 2 or 3 Rc radicals as defined above. Another embodiment of the invention relates to compounds of the formula I, wherein R4 together with R2 is a bivalent radical Y as defined above and which is preferably selected from O, S, CH = N, 0-CH2, OC (O) or NH-C (O), where in the last 4 residues either the carbon atom or the heteroatom are attached to the phenyl ring , in particular of O, S, 0-CH2, and OC (O), where in the last 2 residues, the heteroatom is attached to the phenyl ring. More preferably, R4 and R2 are together an oxygen atom or OC (O) in particular O. In this embodiment, Ar in the formula I is preferably phenyl, which is unsubstituted or substituted by 1, 2 or 3, in particular 0, 1 or 2 Rc radicals as defined above.
Apart from this, Rb is preferably selected from halogen, Ci-C4 alkyl, C1-C4 alkoxy, haloalkoxy d-C4 and haloalkyl d-C4. If present, R7, R8 are preferably selected, independently from each other, of hydrogen and d-C4 alkyl. If present, R 9 is preferably selected from hydrogen, d-C 4 alkyl and d-C 4 alkylcarbonyl, in particular hydrogen. If present, R 10 is preferably selected from hydrogen, halogen and C 1 -C 4 alkyl, in particular hydrogen. If present, R11, R12 are preferably selected, independently from each other, of hydrogen and d-C4 alkyl, in particular hydrogen. If present, R 13 is preferably selected from hydrogen and d-C 4 alkyl, in particular hydrogen. A very preferred embodiment of the invention relates to compounds of the general formula la: wherein k is 0, 1, 2 or 3, and wherein A, Q, R1, R2, R3, R5 and Rc are as defined above. Among the compounds are preferred those in which Q, A, R1, R2, R3, R5 and Rc have the given meanings as preferred. Examples of the compounds are given in the following Tables 1 to 180: Table 1: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and k is 0 (ie ( Rc) k is absent) and where Q and A are given in Table A; Table 2: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4- fluorine and in which Q and A are given in Table A; Table 3: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 4: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 3- fluorine and in which Q and A are given in Table A; Table 5: Compounds of the formula la, in which R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 3-difluoromethoxy and wherein Q and A are given in Table A; Table 6: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 3-trifluoromethyl and wherein Q and A are given in Table A; Table 7: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in Table A; Table 8: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; Table 9: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A; Table 10: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 2-F and in which Q and A are given in Table A; Table 11: Compounds of the formula la, wherein R is H, R3 is H, R2 is H, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 12: Compounds of the formula la, wherein R is H, R3 is H, R2 is H, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 13: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 2-CF3 and wherein Q and A are given in Table A; Table 14: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is H, R5 is H and (Rc) k is 4-OCH3 and wherein Q and A are given in Table A; Table 15: Compounds of the formula la, wherein R is H, R3 is H, R2 is H, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Table 16: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and k is 0 (ie (Rc) k is absent) and wherein Q and A are given in Table A; Table 17: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4-fluorine and wherein Q and A are given in Table A; Table 18: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 19: Compounds of the formula la, wherein R is H, R3 is H, R2 is F, R5 is H and (Rc) k is 3-fluorine and wherein Q and A are given in Table A; Table 20: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 3- difluoromethoxy and wherein Q and A are given in Table A; Table 21: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 3- trifluoromethyl and wherein Q and A are given in Table A; Table 22: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in Table A; Table 23: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; Table 24: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A; Table 25: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 2-F and wherein Q and A are given in Table A; Table 26: Compounds of the formula la, wherein R is H, R3 is H, R2 is F, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 27: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 28: Compounds of the formula la, wherein R is H, R3 is H, R2 is F, R5 is H and (Rc) k is 2- CF3 and wherein Q and A are given in Table A; Table 29: Compounds of the formula la, wherein R is H, R3 is H, R2 is F, R5 is H and (Rc) k is 4- OCH3 and wherein Q and A are given in Table A; Table 30: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is F, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Table 31: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and k is 0 (ie (Rc) k is absent) and wherein Q and A are given in Table A; Table 32: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-fluorine and wherein Q and A are given in Table A; Table 33: Compounds of the formula la, in which R1 is H, and R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 34: Compounds of the formula la, in which R1 is H, and R3 is H, R2 is Cl, R5 is H and (Rc) k is 3-fluorine and wherein Q and A are given in Table A; Table 35: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 3-difluoromethoxy, and wherein Q and A are given in Table A; Table 36: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 3-trifluoromethyl and wherein Q and A are given in Table A; Table 37: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in Table A; Table 38: Compounds of the formula la, wherein R is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; Table 39: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A; Table 40: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 2-F and in which Q and A are given in Table A; Table 41: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 42: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 43: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 2-CF3 and wherein Q and A are given in Table A; Table 44: Compounds of the formula la, where R is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 4-OCH3 and wherein Q and A are given in Table A; Table 45: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Cl, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Table 46: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Br, R5 is H and k is 0 (ie (Rc) k is absent) and where Q and A are given in Table A; Table 47: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4- fluorine and wherein Q and A are given in Table A; Table 48: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 49: Compounds of the formula la, in which R1 is H, R3 is H, R2 is B, R5 is H and (Rc) k is 3- fluorine and in which Q and A are given in Table A; Table 50: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 3-difluoromethoxy and wherein Q and A are given in Table A; Table 51: Compounds of the formula la, in which R is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 3-trifluoromethyl and wherein Q and A are given in Table A; Table 52: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in Table A; Table 53: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; Table 54: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A; Table 55: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 2-F and in which Q and A are given in Table A; Table 56: Compounds of the formula la, in which R is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 57: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 58: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 2-CF3 and wherein Q and A are given in Table A; Table 59: Compounds of the formula la, in which R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 4-OCH3 and wherein Q and A are given in Table A; Table 60: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is Br, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Table 61: Compounds of the formula la, in which R1 is H, R3 is H, R2 is CH3, R5 is H and k is 0 (ie (Rc) k is absent) and where Q and A are given in Table A; Table 62: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-fluorine and wherein Q and A are given in Table A; Table 63: Compounds of the formula la, wherein R is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 64: Compounds of the formula la, in which R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 3- fluorine and in which Q and A are given in Table A; Table 65: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (RG) k is 3-difluoromethoxy and wherein Q and A are given in Table A; Table 66: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 3-trifluoromethyl and wherein Q and A are given in Table A; Table 67: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-fluoro-3-trifluoromethyl and wherein Q and A are given in Table A; Table 68: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; and Table 69: Compounds of the formula la, wherein R is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A. Table 70: Compounds of the formula la, in which R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 2-F and in which Q and A are given in Table A; Table 71: Compounds of the formula la, wherein R is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 72: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 73: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 2-CF3 and wherein Q and A are given in Table A; Table 74: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 4-OCH3 and wherein Q and A are given in Table A; Table 75: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH3, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Table 76: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and k is 0 (ie (Rc) k is absent) and wherein Q and A are given in Table A; Table 77: Compounds of the formula la, wherein R is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 4-fluorine and wherein Q and A are given in Table A; Table 78: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 4-chloro and wherein Q and A are given in Table A; Table 79: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 3- fluorine and wherein Q and A are given in Table A; Table 80: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 3-difluoromethoxy and wherein Q and A are given in Table A; Table 81: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 3-trifluoromethyl and wherein Q and A are given in Table A; Table 82: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 4-fluoro-3-trif luoromethyl and wherein Q and A are given in Table A; Table 83: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (R °) k is 4-methoxy-3-trifluoromethyl and wherein Q and A are given in Table A; Table 84: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 4-methylthio-3-trifluoromethyl and wherein Q and A are given in Table A; Table 85: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 2-F and wherein Q and A are given in Table A; Table 86: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 2-CH3 and wherein Q and A are given in Table A; Table 87: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 2-OCH3 and wherein Q and A are given in Table A; Table 88: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 2-CF3 and wherein Q and A are given in Table A; Table 89: Compounds of the formula la, wherein R1 is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 4-OCH 3 and wherein Q and A are given in Table A; Table 90: Compounds of the formula la, wherein R is H, R3 is H, R2 is CH2CH3, R5 is H and (Rc) k is 2-OCHF2 and wherein Q and A are given in Table A; Tables 91 to 180: Compounds of the formula la, wherein R1, R2, R3 and (Rc) k are as defined in one of Tables 1 to 90, Q and A are given in Table A and R5 is methyl instead of hydrogen. Table A: In Table A, the heteroatom of residue Q is linked to radical A.
Another embodiment of the invention of very special preference relates to compounds of the general formula la ': wherein k is 0, 1, 2 or 3, and wherein A, Q, R1, R2, R3, R5, R6 and Rc are as defined above. Among the compounds', those in which Q, A, R1, R2, R3, R5, R6 and Rc have the given meanings are preferred. The examples of the compounds are given in the following tables 181 to 360: Tables 181 to 270: Compounds of the formula f ', wherein R1 is H, R3 is H, R2 is H, R5 is H, R6 is CH3 and (Rc) k are as defined in one of Tables 1 to 90 and Q and A are given in Table A. Tables 271 to 360: Compounds of the formula la ', wherein R1 is H, R3 is H, R2 is H, R5 is CH3, R6 is CH3 and (R °) k are as defined in one of Tables 1 to 90 and Q and A are given in Table A. Another embodiment of the invention of very special preference refers to compounds of the general formula Ib: where k is 0, 1, 2 or 3, and where A, Q, R, R3, R5 and Rc are as previously defined and Y is as previously defined. Among the compounds la, those in which Y is O, OCH2 or S and in which Q, A, R1, R3, R5 and Rc have the given meanings are preferred. The examples of compounds Ib are given in the following tables 361 to 378: Table 361: Compounds of the formula la, in which Y is O, R1 is H, R3 is H, R5 is H and k is 0 (ie (Rc) k is absent) and where Q and A are given in Table A; Table 362: Compounds of the formula la, in which Y is O, R1 is H, R3 is H, R5 is CH3 and k is 0 (ie (Rc) k is absent) and wherein Q and A are given in Table A; Table 363: Compounds of the formula la, in which Y is S, R1 is H, R3 is H, R5 is H and k is 0 (ie (Rc) k is absent) and where Q and A are given in Table A; Table 364: Compounds of the formula la, in which Y is S, R1 is H, R3 is H, R5 is CH3, and k is 0 (ie (Rc) k is absent) and where Q and A are given in Table A; Table 365: Compounds of the formula la, wherein Y is O, R1 is H, R3 is H, R5 is H and (Rc) k is 4- Cl and wherein Q and A are given in Table A; Table 366: Compounds of the formula la, wherein Y is S, R1 is H, R3 is H, R5 is H and (Rc) k is 4- Cl and wherein Q and A are given in Table A; Table 367: Compounds of the formula la, wherein Y is O, R1 is H, R3 is H, R5 is CH3 and (R °) k is 4-CI and wherein Q and A are given in Table A; Table 368: Compounds of the formula la, in which Y is S, R1 is H, R3 is H, R5 is CH3 and (R °) k is 4-CI and in which Q and A are given in Table A; Table 369: Compounds of the formula la, in which Y is O, R1 is H, R3 is H, R5 is H and (Rc) k is 4- Cl, 5-N0 and wherein Q and A are given in Table A; Table 370: Compounds of the formula la, in which Y is S, R1 is H, R3 is H, R5 is H and (Rc) k is 4- Cl, 5-N02 and in which Q and A are given in Table A; Table 371: Compounds of the formula la, in which Y is O, R1 is H, R3 is H, R5 is CH3 and (Rc) k is 4-CI, 5-N02 and wherein Q and A are given in Table A; Table 372: Compounds of the formula la, in which Y is S, R1 is H, R3 is H, R5 is CH3 and (Rc) k is 4-CI, 5-N02 and wherein Q and A are given in Table A; Table 373: Compounds of the formula la, in which Y is OCH (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is H and k is 0 (ie (Rc) k is absent ) and where Q and A are given in Table A; Table 374: Compounds of the formula la, wherein Y is OCH2 (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is CH3 and k is 0 (ie (Rc) k is absent ) and where Q and A are given in Table A; Table 375: Compounds of the formula la, in which Y is OCH2 (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is H and (Rc) k is 4-CI and in the that Q and A are given in Table A; Table 376: Compounds of the formula la, wherein Y is OCH2 (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is CH3 and (Rc) k is 4-CI and in the that Q and A are given in Table A; Table 377: Compounds of the formula la, wherein Y is OCH2 (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is H and (Rc) k is 4-CI, 5- N02 and where Q and A are given in Table A; Table 378: Compounds of the formula la, wherein Y is OCH2 (the oxygen atom is attached to the phenyl ring), R1 is H, R3 is H, R5 is CH3 and (Rc) k is 4-CI, 5- N02 and wherein Q and A are given in Table A. The compounds of formula I can be easily synthesized using techniques generally known to chemists in organic synthesis. Scheme 1: The compounds of formula I, wherein R6 is H, can be obtained from compounds II by hydrogenation of the C = N double bond in II according to standard methods of organic chemistry well known in the art and described, by example, in US 2002022730, Tetrahedron 1994, 50, 4399 ^ .428, Tetrahedron 2002, 58, 7925-7932 or Trends in Heterocyclic Chemistry 1997, Vol 5, 17-36. Hydrazides I bearing substituents R6 other than hydrogen can be obtained by functionalizing hydrazides I with R6 = H by well known methods such as described in Letters in Peptide Science 2003, 10, 1-9, J. Am. Chem. Soc. 2004, 126, 5366-5367 or Synthetic Communications 2002, 32, 3603-3610 (see scheme 2). Scheme 2: If the individual compounds I can not be obtained by the route described above, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described. The preparation of the compounds of the formula I can lead to them by obtaining them as isomeric mixtures (stereoisomers, enantiomers). If desired, they can be solved by means of the usual methods for this purpose, such as crystallization or chromatography, also in optically active adsorbate, to give the pure isomers. The acylhydrazones of formula II are known in the art, for example, from PCT / EP 2004/005681, or can be obtained by applying synthetic methods described, for example, in WO 87/06133 by analogy. For example, the appropriate hydrides lll can react with aldehydes, esters or ketones IV according to scheme 3 to form acylhydrazones of the formula II. Scheme 3: l | H '(IV) (I I) The compounds of formula I are effective through contact (through the floor, glass, wall, bed elastic, carpet, parts of plants or parts of animals) and / or by ingestion (bait or plant part). The compounds of the formula I are particularly suitable for effectively controlling nematodes and insects. In particular, are suitable for controlling the following pests: insects of the order of Lepidoptera, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura Fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Elands insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterránea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliating, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Mal nematode, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella , Sparganothis pilleriana, Spodoptera eridania, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis: Coleoptera (cascarudos), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar , Anthonomus grandis, Anthonomus pomorum, Atomana lineans, Blastophagus pmiperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertmus, Cpocens asparagi, Diabrotica longicornis, Diabrotica 12 -punctata, Diabrotica virgifera, Epilachna vanvestis, Epitnx hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bihneata, Lema melanopus, Leptinotarsa decemlineata, Limomus californicus, Lissorhoptrus oryzophilus, Melanotus commums, Meligethes aeneus, Melolontha hippocastam , Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, O orrhynchus ovatus, Phaedon cochleapae, Phyllotreta chrysocephala, Phyllophaga sp, Phyllopertha horticultural, Phyllotreta nemorum, Phyllotreta stnolata, Popillia japonica, Sitona lineatus and Sitophilus granaria, Diptera, for example, Aedes aegypti, Aed es vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hommivorax, Chrysomya macellana, Contannia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia caniculans, Gasterophilus mtestinalis, Glossina morsitans, Haematobia irptans , Haplodiplosis equestps, Hylemyia platura, Hypoderma lineata, Lipomyza sativae, Lmomyza trifoln, Lucilia caprina, Lucilia cuprma, Lucilia sencata, Lycona pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella fnt, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Typula oleracea and Typula paludosa, Thysanoptera, for example, Dichromothnps spp, Franklmiella fusca, Frankhniella occidentalis, Franklmiella tptici, Scirtothpps citn, Thnps oryzae, Thnps palmi and Thrips tabací, hymenoptera , for example, Athalia rosae, Atta cephalotes, A tta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomonum pharaonis, Solenopsis geminata and Solenopsis invicta, heteroptera, for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus mtermedius, Eurygaster integnceps, Euschistus impictiventns, Leptoglossus phyllopus, Lygus lineolans, Lygus pratensis, Nezara vmdula, Piesma quadrata, Solubea insulans and Thyanta perditor, homoptera (in particular aphids), for example, Acyríhosiphon onobrychis, Adelges wool, Aphidula nasturtii, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis Sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus Horni, Cerosipha gossypii, Chaetosiphon fragaefolii , Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicóla, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilapan / ata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla pirí, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala , Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii, Isoptera (termites), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis, Orthoptera, for example, Acheta domestica, Blatta orientalis, Germanic Blattella, Forfícula aurícularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus, and Nematodes: plant parasitic nematodes such as root knot nematodes , Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cystic nematodes, Globodera rostochiensis, Globodera paluda, Globodera tabacum and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; seed nematodes, Anguina funesta, Anguina tritici and other Anguina species; nematodes of stems and leaves, Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi and other Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and others Bursaphelenchus species, annular nematodes, Cpconema species, Cpconemella species, Cnconemoides species, and Mesocriconema species, nematodes of stems and bulbs, Ditylenchus destructor, Ditylenchus dipsací, Ditylenchus myceliophagus and other Ditylenchus species, awl nematodes, Dolichodorus species, spiral nematodes, Helicotylenchus dihystera, Helicotylenchus multicinctus and other Helicotylenchus species, Rotylenchus robustus and other Rotylenchus species, pod nematodes, Hemicyc ophora species and Hemicpconemoides species, Hirshmanniella species, spear nematodes, Hoplolaimus columbus, Hoplolaimus galeatus and other Hoplolaimus species, false nematodes of root knots , Nacobbus aberrans and other Nacobbus species, needle nematodes, Longidorus elongates and other Longidorus species, needle nematodes, Paratylenchus species, insect nematodes, Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus goodeyi, F'ratylencus neglectus, Pratylenchus pen etrans, Pratylenchus scnbnep, Pratylenchus vulnus, Pratylenchus zeae and other Pratylench? s species; Radinaphelenchus cocophilus and other Radinaphelenchus species, excavating nematodes, Radopholus similis and other Radopholus species, reniform nematodes, Rotylenchulus reniformis and other Rotylenchulus species, Scutellonema species, short and coarse root nematodes, Trichodorus pnmitivus and other Tnchodorus species, Paratnchodorus minor and other Paratpchodorus species , atrophied nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species and Merlinius species, citrus nematodes, Tylenchulus semipenetrans and other Tylenchulus species, dagger nematodes, Xiphmema amencanum, Xiphmema index, Xiphmema diversicaudatum and other Xiphinema species, and other nematode species plant parasites The compounds of the formula I and their salts are also useful for controlling arachnids (Arachnoidea), such as Acariña, for example, from the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma amencanum, Amblyomma vapegatum, Argas persicu s, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricmus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnmi, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Epophyidae spp such as Aculus schlechtendali, Phyllocoptrata oleivora and Enophyes sheldoni, Tarsonemidae spp such as Phytonemus palhdus and Polyphagotarsonemus latus, Tenuipalpidae spp such as Brevipalpus phoenicis, Tetranychidae spp such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis. For use in a method according to the invention, the compounds I can be converted into customary formulations, for example, solutions, emulsions, suspensions, powders, powders, pastes and granules. The form of use depends on the particular purpose; they are intended in each case to ensure a fine and uniform distribution of the compound of the formula I according to the invention. The formulations are prepared in a known manner, for example, by spreading the ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants. The solvents / auxiliaries which are suitable are essentially: water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones ( for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, mixtures of solvents and the like, carriers such as ground natural minerals and ground synthetic minerals (eg, kaolin, chalk, talcum, chalk) and ground synthetic minerals (eg, high dispersion silica, silicates) can also be used.; emulsifiers such as nonionic and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin sulfite waste liquors and methylcellulose. Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, sulfates of acid alcohols, fatty acids and ethers of glycol sulfate acid alcohol, in addition to condensates of naphthalenesulfonate and derivatives of naphthalene with formaldehyde, condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, octylphenolpolyoxyethylene ether, ethoxylated sooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and alcohol acid / ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol acetal ether, sorbitol esters, lignosulfite waste liquors and methylcellulose. For the preparation of solutions, emulsions, pastes or oil dispersions for direct spray, mineral oil fractions with a medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable origin are suitable. animal, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone and water. Powders, dispersion materials and products that can be transformed into powder can be prepared by mixing or concomitant grinding of the active substances with a solid carrier. The granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, Fuller's earth, limestone, lime, chalk, clayey earth, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate , magnesium oxide, ground synthetic materials, fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and products of vegetable origin, such as cereal flour, tree bark meal, flour walnut shell wood and flour, cellulose powders and other solid carriers. In general, the formulations comprise from 0.01 to 95% by weight, preferably from OJ to 90% by weight of active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). The following are examples of formulations: 1. Products for dilution with water A) Water-soluble concentrates (SL) 10 parts by weight of a compound according to the invention are dissolved in water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound is dissolved by dilution with water. B) Dispersible concentrates (DC) 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water produces a dispersion. C Emulsifiable concentrates (EC) 15 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Dilution with water gives an emulsion. D Emulsions (EW, EO) 40 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced into water by means of an emulsifying machine (Ultraturrax) and becomes a homogeneous emulsion. Dilution with water gives an emulsion. E Suspensions (SC, OD) In a stirred circular mill, 20 parts by weight of a compound according to the invention are mixed with addition of dispersants and humectants and water or an organic solvent to give a fine suspension of active compound. By dilution with water a stable suspension of the active compound is obtained. F Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a compound according to the invention are finely milled with the addition of dispersants and wetting agents and prepared as hydrodispersing or water-soluble granules by a technical method (for example extrusion , spray tower, fluid bed). By dilution with water a stable dispersion or suspension of the active compound is obtained. G Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of dispersants, wetting agents and silica gel. By dilution with water a dispersion or solution of the active compound is obtained. 2. Products to be applied without dilution H Powders for forming powder (DP) 5 parts by weight of a compound according to the invention are ground finely and mixed well with 95% finely divided kaolin. So you get a product like dust.
I Granules (GR, FG, GG, MG) 0.5 parts by weight of a compound according to the invention are ground finely and associated with 99.5% carriers. The current methods are extrusion, spray drying or fluid bed. This way granules are obtained that are applied undiluted. J Solutions ULV (UL) 10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example, xylene. This way you get a product to apply undiluted. The active ingredients can be used as such, in the form of their formulations or the forms of use prepared therefrom, for example in the formulation of direct spray solutions, powders, suspensions or dispersions, emulsions, dispersions in oil, pastes, products dust formers, materials for dispersion, or granules, by spraying, atomizing, dusting, dispersing or pouring. The forms of use depend entirely on the proposed purposes; the intention is to ensure in each case the distribution as fine as possible of the active compounds according to the invention. Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. To prepare emulsions, pastes or oily dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by means of a humectant, viscosity, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetting agent, viscosifier, dispersant or emulsifier and, if appropriate, solvent or oil, and said concentrates are suitable for dilution with water. The concentrations of active compound in the ready-to-use preparations can be varied within relatively broad ranges. In general, they have from 0.0001 to 10%, preferably from 0.01 to 1%. The active ingredients can also be used successfully in the ultra-low volume process (ULV), by which it is possible to apply formulations comprising more than 95% by weight of active compound, or even to apply the active compound without additives. The compositions according to this invention may also contain other active ingredients, e.g. ex. pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients can be used sequentially or in combination with the compositions described above, if appropriate, they can also be added immediately. before use (tank mix) For example, the plants may be sprayed with a composition of this invention either before or after being treated with other active ingredients. These agents are usually mixed with the agents according to the invention in a ratio by weight from 1 100 to 100 1 The following list of pesticides, together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, without limitations Acetate organophosphates, azamethiphos, azinphos-methyl, chlorpipfos , clorpipfos-methyl, clorfenvinfos, diazinona, dichlorvos, dicrotofos, dimethoate, disulfotona, etiona, fenitroc ione, fenciona, isoxaciona, malaciona, methamidophos, metidaciona, methyl-paraciona, mevinfos, monocrotofos, oxidemetone-methyl, paraoxone, paraciona, fentoato, fosalona, fosmet, fosfamidona, phorate, phoxim, methyl-pipmifos, profenofos, protiofos, sulprofos, tetrachlorvinphos, terbufos, tpazofos, tpclorfona, carbamates alanicarb, aldicarb, bendiocarb, benfuracarb, carbaplo, carbofuran, carbosulfane, phenoxycarb, furathiocarb indoxacarb methiocarb, methomyl, oxamyl, pipmicarb, propoxur, thiodicarb, tpazamate, pyrethroids bifentpna, ciflutpna, cipermetpna, alfa- cypermetpna, deltametpna, esfenvalerate, etofenprox, fenpropatnna, fenvalerate, cihalotnna, lambda-cyhalothrin, permetpna, silafluofen, tau-fluvalinate, teflutpna, tralometpna, zeta-cipermetpna, growth regulators a) inhibitors of the synthesis of chitin benzoylureas chlorofluazurona, diflubenzurona, flucicloxurona, flufenoxurona, hexaflumurona, lufenurona, novalurona, teflubenzurona, tpflumurona, buprofezma, diofenolano, hexitiazox , etoxazole, clofentazm, b) antagonists of ecdysone halofenozide, methoxyfenozide, tebufenozide, c) juvenoides pipproxifen, methoprene, phenoxycarb, d) inhibitors of lipid synthesis spirodiclofen, Vanos abamectin, acequinocyl, acetamippd, amitraz, azadirachtin, bifenazate, cartap , chlorfenapyr, chlordimeform, cyromazine, diafentiurone, dinetofuran, diofenolane, emamectin, endosulfan, ethiprole, phenazaquin, fipronil formetanate, formetanate hydrochloride, hydramethylnon, imidaclopnda, indoxacarb, metaflumizone (= 4- { (2Z) -2- ( { [4- (trifluoromethoxy) anilino] carbonyl] -hydrazono) -2- [3- (trifluoromethyl) -phenyl-ethyl-phenyl} benzo-nitrile), nitenpyram, pyridaben, pymetrozine, spinosad, sulfur, tebufenpyrad, thiamethoxam, thiacloprid, thiocyclam, spiromesifen, spirodiclofen, pyridalyl and the pesticide of the following formula as described in WO 98/05638: Fungicides are those which are selected from the group consisting of acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl, amine derivatives such as aldimorf, dodin, dodemorf, fenpropimorf, fenpropidin, guazatin, iminoctadine, spiroxamine, tridemorph, anilinopyrimidines such as pyrimethanil, mepanipyrim or cirodinyl, • antibiotics such as cycloheximide, griseofulvin, casugamycin, natamycin, polyoxin or streptomycin, • azoles such as bitertanol, bromoconazole, ciproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, protioconazole, tebuconazole, triadimefonone, triadimenol, triflumizole, triticonazole, flutriafol • dicarboximides such as iprodione, myclozoline, procymidone, vinclozoline, • dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb, • heterocyclic compounds such as anilazine, benomyl, boscalide, carbendazim, carboxin, oxycarboxin, ciazofamide, dazomet, dithianone, famoxadone , fenamidone, fenarimol, fuberidazole, flutolanil, furametpir, isoprothiolane, mepronil, nuarimol, probenazole, proquinazide, pirifenox, pyroquilone, quinoxifene, siltiofam, thiabendazole, thifluzamide, thiophanate-methyl, thiadinyl, tricyclazole, triforin, • copper fungicides such as blending de Bordeaux, copper acetate, copper oxychloride, basic copper sulfate, • nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitroftalisopropyl • phenylpyrroles such as fenpiclonil or fludioxonil, • sulfur • other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamide, cymoxanil, diclomezine, diclocimet, dietofencarb, edifenfos, etaboxam, fenhexamida, fentina-acetate, fenoxanilo, ferimzona, fluazinam, fosetilo, fosetil-aluminum, iprovalicarb, hexachlorobenzene, metrafenona, pencicurona, propamocarb, ftalida, toloclofos-methyl, quintozene, zoxamida • strobilurinas such as azoxystrobin, dimoxystrobin, fluoxastrobina , cresoxim-methyl, methominostrobin, orisastrobin, picoxystrobin or trifloxystrobin, • sulfenic acid derivatives such as captafol, captan, diclofluanide, folpet, tolylfluanide • cinemides and analogs such as dimetomorph, flumetover or flumorf. The aforementioned compositions have particular utility to protect plants against infestation of said pests or to combat these pests in infested plants. However, the compounds of the formula I are also suitable for the treatment of seeds. Seed treatment compositions include for example fluid concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for treatment with WS slurries, water soluble SS powders and ES emulsion. The application to the seeds is done before sowing, either directly in the seeds or after they have pregerminated. Preferred FS formulations of the compounds of formula I for the treatment of seeds generally comprise from 0.5 to 80% of the active ingredient, from 0.05 to 5% of a humectant, from 0.5 to 15% of a dispersing agent, from 0J to 5% of a thickener, from 5 to 20% of an antifreeze agent, from 0J to 2% of an antifoam agent, from 1 to 20% of a pigment and / or a dye, from 0 to 15% of an adhesive / adhesion agent, 0 to 75% of a filler / vehicle, and 0.01 to 1% of a preservative. Suitable pigments or dyes for the seed treatment formulations are blue pigment 15: 4, blue pigment 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment Red 1 12, red pigment 48: 2, red pigment 48: 1, red pigment 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6 , brown pigment 25, basic violet 10, basic violet 49, red acid 51, red acid 52, red acid 14, acid blue 9, acid yellow 23, basic red 10, basic red 108. Adhesives / adhesion agents are added to improve the adhesion of the active materials on the seeds after the treatment. Suitable adhesives are OE / OP block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamines, polyethyleneimines (Lupasol®, Polymin®), polyethers and copolymers derived therefrom. polymers. Compositions useful for the treatment of seeds are for example: A soluble concentrates (SL, LS) D Emulsions (EW, EO, ES) E Suspensions (SC, OD, FS) F hydrodispersible granules and water-soluble granules (WG, SG) G water-dispersible powders and water-soluble powders (WP, SP, WS) H Sprayable powders (DP, DS) For use against ants, termites, wasps, flies, mosquitoes, crickets or cockroaches, the compounds of the formula are preferably used in a bait composition. The bait can be a liquid, solid or semi-solid preparation (for example, a gel). The solid baits can be formed with various configurations and forms suitable for the respective application, for example, granules, blocks, bars, discs. Liquid baits can be filled in various devices to ensure proper application, for example, open containers, spray devices, droplet sources or sources of evaporation. The gels can be based on aqueous or oily matrices, and can be formulated for particular needs in terms of adhesiveness, moisture retention or moisture characteristics. The bait used in the composition is a sufficiently attractive product to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attraction can be manipulated by using food stimulants or sex pheromones. Food stimulants are they choose, for example, but not exclusively, animal and / or vegetable proteins (meat, fish or blood meal, parts of insects, egg yolk), fats and oils of animals and / or of vegetable origin, or mono, oligo- or polyorganosccharides, especially sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or their specific parts can also serve as a food stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art. Formulations of compounds of formula I as aerosols (for example in spray cans), oil sprays or spray pumps are very suitable for the non-professional user for the control of pests such as flies, fleas, ticks, mosquitoes or cockroaches. Aerosol prescriptions are preferably composed of the active compound, solvents such as lower alcohols (eg, methanol, ethanol, propanol, butanol), ketones (eg, acetone, methyl ethyl ketone), paraffinized hydrocarbons (eg, kerosenes) with ranges boiling at about 50 to 250 ° C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, other auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate with 3-7 mole of ethylene, ethoxylated fatty alcohol, perfumed oils such as essential oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases. Oily spray formulations differ from aerosol containers in that no propellants are used. The compounds of formula I and their respective compositions can also be used in spirals against mosquitoes and fumigants, smoke spools, vaporizing plates or long-acting vaporizers and also in wetted papers, moistened pads or other independent heat vaporizing systems.
Methods to control infectious diseases transmitted by insects (for example, malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) with compounds of the formula I and their respective compositions also include the treatment of the surfaces of huts and dwellings, air spraying and the impregnation of curtains, tents , clothes, mosquito nets, tsetse fly traps or similar. Insecticidal compositions for application to fibers, fabrics, fabrics, yarns, netting or tarpaulins and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents, for example, are N, N-diethyl-meta-toluamide (DEET), N, N-diethylphenylacetamide (DEPA), 1- (3-cyclohexan-1-yl-carbonyl) -2-methylpiperine, lactone (2-hydroxymethylcyclohexyl) acetic acid, 2-ethyl-1, 3-hexanediol, indalone, methylneodecanamide (MNDA), a pyrethroid not used for the control of insects such as. { (+/-) - 3-allyl-2-methyl-4-oxocyclopent-2 - (+) - enyl - (+) - trans-chrysanthemate (esbiothrin), a repellent derived or identical from plant extracts such as limonene, eugenol , (+) - eucamalol (1), (-) - l-epi-eucamalol or crude plant extracts for plants such as Eucaliptus maculata, Vitex rotundifolia, Cimbopogan martinii, Cimbopogan citratus (lemon grass), Cimopogan nartdus (citronella). Suitable linkers are selected, for example, from polymers and copolymers of vinyl esters of aliphatic acids (such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate and acrylate. of methyl, mono- and diethylene-unsaturated hydrocarbons, such as styrene and aliphatic dienes, such as butadiene. The impregnation of curtains and mosquito nets is done mainly by immersion of the textile material in emulsions or dispersions of the insecticide or sprayed on the nets. The compounds of the formula I and their compositions can be used to protect inanimate material, in particular cellulose-based materials such as wood materials, e.g. eg, trees, fences, chairs, etc. and constructions such as houses, warehouses, factories, but also construction materials, furniture, leather, fibers, vinyl items, electric cables and wires, etc. against ants and / or termites, and to control ants and termites so that they do not harm crops or humans (eg when the plague invades homes or public buildings). The compounds of the formula I are applied not only to the surface of the surrounding soil or in the soil Under the floor, in order to protect wood materials, they can also be applied to woodwork items such as concrete surfaces under the floor, room posts, beams, plywood, furniture, etc., wooden articles such as agglomerate plates, countertops, etc. and vinyl items such as coated electrical cables, vinyl sheets, thermal insulating material such as styrene foams, etc. In the case of application against ants that damage crops or humans, the ant controller of the present invention is applied to the crops or the surrounding soil, or is applied directly on the anthills or the like. In the methods according to the invention the pests are controlled by contacting the parasite / target pest, its food source, habitat, feed site or locus with an effective pesticidal amount of at least one compound I, or its salt , or with a composition containing an effective amount as a pesticide of at least one compound I, or its salt. "Locus" means a habitat, feeding site, plant, seed, soil, area, material or environment in which a pest or parasite develops or may develop. In general, "pesticidally effective amount" means the amount of active ingredient necessary to achieve an observable effect on the development, including the effects of necrosis, death, retardation, prevention, and elimination, destruction, or otherwise reduction of the presence and activity of the target organism. The pesticidally effective amount may vary for the various compounds / compositions used in the invention. An effective pesticidal amount of the compositions will vary according to the prevailing conditions such as pesticide effect of interest and duration, weather, target species, locus, mode of application, and the like. The compounds of the invention can also be applied preventatively at the sites at which the pests are expected to appear. The compounds of the formula I can also be used to protect the developing plants against attack or infestation by pests upon contact with the plant effective amount as a pesticide of the compounds of the formula I. Thus, "contacting" includes direct contact (by application of the compounds / compositions directly on the pest and / or the plant, in general the foliage, stems or roots of the plant) and indirect contact (by application of the compounds / compositions to the locus of the plague and / or plant).
In the treatment of the seed, the application rates of the active compounds are generally from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2. The application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 of treated material, preferably from 0J g to 50 g per m2. Insecticidal compositions for use in the impregnation of materials generally contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent insecticide. For use in compositions as baits, the typical content of active ingredient is from 0.001% by weight to 15% by weight, preferably from 0.001% by weight to 5% by weight of active compound. For use in spray compositions, the content of active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and more preferably from 0.01 to 15% by weight. For use in crop plants under treatment, the application rate of active ingredients of this invention can be in the range of 0J to 4000g per hectare, desirably from 25g to 600g per hectare, more desirably from 50g to 500g per hectare, more desirably from 50g to 500g per hectare. hectare. In seed treatment, application rates of the mixture are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed. The present invention is also illustrated in more detail with the following examples. The products are characterized by high performance liquid chromatography / mass spectrometry (HPLC / MS) coupling, by NMR or by their melting points. HPLC Column: column RP-18 (Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water in a ratio of 5:95 to 95: 5 in 5 minutes at 40 ° C. In the examples the following abbreviations are used: p.f .: melting point THF: tetrahydrofuran MS: quadrupole ionization by electroaspersion, 80 V (positive modules) RT: retention time Example 1 (compound A-90 of Table B): 1.1 N-methyl-furan-2-carboxylic acid hydrazide A a mixture of 3.0 g (65 mmol) of methylahydrazine in 35 ml of dichloromethane is added 0.85 g (6.5 mmol) of furan-2-carboxylic acid chloride in 35 ml of dichloromethane at 0 ° C in 1 hour. The mixture was allowed to warm to room temperature and was stirred for 3 hours. After evaporation of the solvent, the oil obtained had sufficient purity to perform other reactions (HPLC / MS: RT = 0.707 min, m / z = 140 [M + H] +). 1.2 N-methyl-N '- [2-methyl-3- (2-fluorophenyl) -alylidene] -furan-2-carboxylic acid hydrazide A mixture of 95 mg (0.66 mmol) of N-methyl-hydrazide of furan-2-carboxylic acid and 98 mg (0.6 mmol) of 2-methyl-3- (2-fluorophenyl) acrolein in 5 ml of methanol was heated with reflux overnight. After cooling to room temperature and evaporation of the solvent, 168 mg (0.59 mmol, 98%) of the desired product was obtained. The compound had sufficient purity for the subsequent reactions (> 90% according to HPLC / MS, RT = 3.640 min, m / z = 287 [M + H] +). 1.3 N '- [3- (2-fluorophenyl) -2-methyl-allyl] -N-methyl-furan-2-carboxylic acid hydrazide A 14 mg (0.4 mmol) of N-methyl-N'- [2-methyl-3- (2-fluorophenyl) -alylidene] -furan-2-carboxylic acid hydrazide and 38 mg (0.64 mmol) of dimethylamine-borane complex in 1 ml of dichloromethane which was cooled to 0 ° C it was added 456 mg (2.4 mmol) of p-toluenesulfonic acid monohydrate in 2 ml of dichloromethane / methanol 3: 1. After stirring the mixture obtained at 0 ° C for 30 min, 2.5 ml of Na 2 CO 3 solution (10% w / v) was added and the mixture was heated to reflux for 30 min. After cooling to room temperature, the organic phase was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over MgSO4 and concentrated in vacuo. There was obtained 95 mg (0.33 mmol, 83%) of N '- [3- (2-fluorophenyl) -2-methyl-allyl] -N-methyl-hydrazide of furan-2-carboxylic acid with a purity > 90% according to HPLC / MS (RT = 3.217 min, m / z = 289 [M + H] +).
Example 2 (compound A-1 of Table B): 2J N '- (3- (3-fluorophenyl) -2-methyl-allylidene) 2-fluorobenzoic acid hydrazide The title compound was obtained by analogy with the method outlined in Example 1.2 by reacting the hydrazide of 2-fluorobenzoic acid with 2-methyl-3- (3-fluorophenyl) acrolein. 2.2 N '- [3- (3-fluorophenyl) -2-methyl-allyl] 2-fluorobenzoic acid hydrazide In a three-necked round bottom flask (50 ml), equipped with a reflux condensate and a thermometer 1, 00 g (3.33 mmol, 1.0 eq) of N '- (3- (3-fluorophenyl) -2-methyl-allylidene) 2-fluorobenzoic acid hydrazide and 314.7 mg (5.34 mmol, 1 , 6 eq) of dimethylamine-borane complex were equilibrated during 5 min in 10 ml of CH2Cl2 at 0 ° C. Then 3.804 g (20.00 mmol, 6.0 eq) of p-toluenesulfonic acid monohydrate was added with a solution in 6 ml of CH2Cl2 / MeOH 3: 1. After stirring at 0 ° C for 30 minutes, 12.5 ml of Na 2 CO 3 solution (10% w / v) and 4 ml MeOH were added and the mixture was refluxed for another 30 minutes. After cooling to room temperature, the organic phase was separated and the aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo. There was obtained 0.956 g (3 J7 mmol, 95%) of N '- (3- (3-fluorophenyl) -2-methyl-allyl) hydrazide of 2-fluorobenzoic acid with a purity > 95% according to HPLC / MS (H-NMR, d6-DMSO, 500MHz, d = 1, 9 (s, 3H), 3.5 (d, 2H), 5.5 (pt, 1H), 6 , 5 (s, 1 H), 7.0-7.15 (m, 3H), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 1 H), 7.4-7.55 (m, 2H), 9.75 ( d, 1 H)). Compounds A2 to A321 shown in Table B, Compounds B1 to B56 shown in Table C, Compounds Ci and C2 shown in Table D, Compounds D1 and D2 shown in Table E, Compounds E1 to E38 shown in table F, compound F1 shown in table G, compounds G1 to G3 shown in table H, compounds H1 to H55 shown in table j, compounds J1 to J26 shown in table K and compounds K1 to K10 shown in Table L were obtained by analogy with the methods of Examples 1 and 2.
Table B 00 or 00 or 00 00 00 oo oo s > 00 ^ 1 00 00 00 CD (Or o (D CD M CD O Table C: co CD The heteroatom of residue Q is linked to radical A C Table D: O Table E: CD Table F - > l co oo co co Table G: o o Table H Table J: or or or -P- Table K or or Table L or The pesticidal action of the compounds of the formula I was demonstrated by means of the following experiments: I Insect activity 1.1 Cotton aphids (aphis gossipii) The active compounds were formulated in 50:50 acetone: water and 100 ppm surfactant Kinetic®. Cotton plants in the cotyledon stage were infested before treatment by placing a heavily infested leaf from a main colony of aphids on the top of each cotyledon. The aphids were allowed to transfer overnight and the leaf was removed from the host. The infested cotyledons were then submerged and shaken in the test solution for and allowed to dry. After 5 days, mortality counts were made. In this test, compounds A10, A1 1, A16, A19, A21, A44, A47, A63, A68, B11, B20 and B25 at 300 ppm showed a mortality higher than 75% compared to untreated controls. 1.2 Green peach aphids (Mizus persicae) The active compounds were formulated in 50:50 acetone: water and 100 ppm of Kinetic® surfactant. Pepper plants in the 2 'leaf pair stage (' California Wonder 'variety) were infested with approximately 40 aphids bred in the laboratory by placing heavily infested leaves on top of the treated plants.
The leaf cuts were removed after 24 hours. The leaves of the intact plants were immersed in gradual solutions of the test compound and allowed to dry. The test plants were kept under fluorescent light in a 24-hr period at 25 ° C and 20-40% relative humidity. The mortality of the aphids in the treated plants, with respect to the mortality in the untreated control plants, was determined after 5 days. In this test, compounds A13, A51, A70, A74, A75, A79, A80, A81, A83, B1, B22 and B34 at 300 ppm showed more than 75% mortality compared to untreated controls. 1.3 Trips of orchids (dichromotrips corbetti) The adults of Dichromotrips corbetti used for the bioassay were obtained from a colony kept continuously under laboratory conditions. For the purpose of the test, the test compound was diluted to a concentration of 500 ppm (weight of the compound: vol diluent) in a 1: 1 mixture of acetone: water, plus 0.01% of Kinetic® surfactant. The thrips potency of each compound was evaluated by a floral immersion technique. Petri dishes were used as a test scenario. All petals of individual, intact orchid flowers were immersed in treatment solution for approximately 3 seconds and allowed to dry for 2 hours. The treated flowers were placed in individual Petri dishes together with 10-15 adult thrips. The petri dishes were then covered with lids. All test scenarios were kept under continuous light and at a temperature of approximately 28 ° C during the test. After 4 days, the number of live thrips in each flower was counted, and along the internal walls of each Petri dish. The thrips mortality level was extrapolated from the amounts of thrips prior to treatment. In this test, the compounds A1, A2, A12, A141, A149, A 155, A173, A218, A223, A260, A301, A303, A305, A319, C1, E3 and E42 at 300 ppm showed more than 75% mortality compared to untreated controls. Bean aphids (Aphis fabae) Nasturtium plants grown in Metro mix at the stage of the first pair of leaves (variety 'Mixed Jewel') were infested with approximately 2-30 aphids raised in the laboratory by placing infested plants cut on top of the plants test. The cut plants were removed after 24 h. Each plant was immersed in the test solution to provide full coverage of the foliage, stem, protruding seed surface and the surrounding cubic surface and allowed to dry in hood. The treated plants are maintained at approximately 25 ° C with continuous fluorescent light. The aphid mortality is determined after three days. In this test, compounds A93, A141, A305, E1, E3 and K6 at 300 ppm showed 75% mortality compared to untreated controls.

Claims (1)

  1. CLAIMS A method to combat selected pests of insects, arachnids and nematodes, which involves putting these pests in contact, their habitat, nutrient soil, food supply, plant, seed, soil, area, material or environment where animal pests grow or they may grow, or the material or materials, plants, seeds, soils, surfaces or spaces to be protected from an attack or infestation caused by said pest with a pesticidally effective amount of a hydrazide compound of the general formula I where it is absent or a covalent bond; A is a cyclic radical selected from phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms as ring members that are independently selected from O, N and S, the heterocyclic radical from 5 or 6. members may have a carbonyl group as ring member and wherein the cyclic radical may have 1, 2, 3, 4 or 5 substituents Ra which are independently selected from halogen, cyano, nitro, C? -C10 alkyl , C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl, C3-C10 haloalkynyl, C1-C10 alkoxy, haloalkoxy d-Cio, C2-C10 alkenyl -oxi, C2-C10 haloalkenyl-oxy, C2-C10 alkynyl-oxy, C3-C10 haloalkynyl-oxy, alkyl dC-io-thio, haloalkyl C? -C10-thio, C1-C10 alkyl sulfinyl, haloalkyl C? C ^ -sulfinyl, alkyl dC-io-sulfonyl, haloalkyl C? -C10-sulfonyl, hydroxy, NR7R8, alkoxy Ci-do-carbonyl, haloalkoxy C1-C10-carbonyl, alkenyl C2-C10 -oxycarbonyl, C2-C- [alpha] -O-oxycarbonyl haloalkenyl, C? -C? alkylcarbonyl, haloalkyl d-Ciocarbonyl, R7R8N- CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy can to be substituted with 1, 2, 3, 4 or 5 substituents Rb which are independently selected from halogen, cyano, nitro, Ci-do alkyl, d-Cio haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl , alkenyl C2-C10, C2-C10 haloalkenyl, C2-C10 alkynyl, C3-C10 haloalkynyl, alkoxy Ci-Cio, haloalkoxy C? -C10, C2-C10 alkenyl-oxy, haloalkenyl C2-C? 0-oxy, alkynyl C2-C? 0-oxy, haloalkynyl C3-C? 0-oxy, alkyl C? -C? other, Ci-Cio-thio haloalkyl, C? -C10 alkyl sulfinyl, C? -C? 0 -sulffinyl haloalkyl, Ccydo-sulphonyl alkyl, d-do-sulfonyl haloalkyl, hydroxy, NR7R8, alkoxy d-C10-carbonyl, haloalkoxy dC? 0 -carbonyl, C2-C10 alkenyl-oxycarbonyl, C2-C10 haloalkenyl-oxycarbonyl, alkyl d-C1C? -carbonyl, haloalkyl d-do-carbonyl and R7R8N-CO-, in where in each case two radicals Ra which are attached to adjacent carbon atoms can form a radical CH = CH-CH = CH or a radical 0 -CH2-0, where in these two radicals 1 or 2 hydrogen atoms can be replaced by a radical Rb as defined above; Q is selected from the group consisting of a single bond, alkylidene d-C4, O-alkylidene d-C4, S-alkylidene C1-C4 and NR9-alkylidene C? -C4, in which the alkylidene group in the last four radicals mentioned is not substituted or carries 1, 2, 3 or 4 substituents selected from OH, = 0, halogen, haloalkyl d-C4 and alkoxy d-C4; or AQ can be d-C1C? alkyl together, which can be substituted with 1 or 2 substituents selected from the group consisting of = 0, OH, d-C4 alkoxy, d-C4 alkyl thio, halogen or C? -C4 alkyl -carbonyloxy; X is C = 0, C = S or S02; Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, wherein the aromatic radical can carry 1, 2, 3, 4 or 5 substituents Rc which are independently selected from halogen, cyano , nitro, C 1 -C 10 alkyl, d-C 10 haloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 halocycloalkyl, C 2 -C 0 alkenyl, C 2 -C 10 haloalkenyl, C 2 -C 10 alkynyl, C 3 -C 10 haloalkynyl, alkoxy dC 0 , haloalkoxy d-C2-C10 alkenyl cyclo-oxy, C2-C10 alkynyl-oxy, C3-C10 haloalkynyl-oxy, C1-do-thio alkyl, haloalkyl d-cyclo-thio. alkyl d-do-suífinilo, haloalquí-C1-C10-sulfinilo, alkyl d-Cio-sulfonyl, haloalkyl d-C10-sulfonyl, hydroxy, NR7R8, alkoxy d-do-carbonyl, haloalkoxy d-C10-carbonyl, alkenyl C2-C? 0-oxycarbonyl, haloalkenyl C2-C10-oxycarbonyl , alkyl d-C10-carbonyl, haloalkyl C? -C? or -carbonyl, alkyl d-C10-carbonyloxy, R7R8N-CO-, phenyl, benzyl and phenoxy, wherein phenyl, benzyl and phenoxy may be unsubstituted or may be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above, and wherein two Rc radicals which are bonded to adjacent carbon atoms can form a 0-CH2-O moiety, wherein in said moiety 1 or 2 hydrogen atoms can be replaced by a radical Rb as defined above; R1 is selected from the group consisting of H, C1-C10 alkyl, C1-C10 haloalkyl, C3-C6 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl, haloalkynyl C2- C10, phenyl and a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of one another, from O, N and S, it being possible for the last two radicals mentioned above not to be substituted or substituted with 1, 2, 3, 4 or 5 substituents Ra as defined above; R2 is a monovalent radical selected from H, halogen, cyano, d-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-do alkenyl, C2-C10 haloalkenyl, C2-C20 alkynyl, C3-C10 haloalkynyl, Ci-do alkoxy, d-C10 haloalkyloxy, C2-C10 alkenyl-oxy, haloalkenyl C2-do-oxy, C2-C alkynyl-oxy, haloalkynyl C3-C? 0-oxy, alkyl C? -C? 0 -thio, haloalkyl d-do-thio, hydroxy-d-C10 alkyl, C? -C? Alkoxy or C1-C10 alkyl, haloalkoxy d-Cio-d-C10 alkyl, C? Alkoxy? C 10 -carbonyl-C 1 -C 10 alkyl, C 1 -C 10 haloalkoxy-carbonyl C 1 -C 10 alkyl and phenyl which may be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above; R3 is selected from the group consisting of H, halogen, cyano, alkyl C1-C10, haloalkyl d-C10, cycloalkyl C3-C-? 0, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C10, alkynyl C2-C10, haloalquinilo C3- C10, alkoxy d-do, haloalcoxi d- C10, C2-C10 alkenyl-oxy, C2-Cio-oxy haloalkenyl, C2-C10 alkynyl-oxy, C3-C10 haloalkynyl-oxy, alkyl d-do-thio, haloalkyl d-Cio-thio, hydroxy-alkyl d-d0 , C 1 -C 6 alkoxy-d-C 10 alkyl, haloalkoxy d-do-d-C 10 alkyl, C 1 -C 10 alkoxy -carbonyl-d-Cio alkyl, halo-d-C 10 alkoxycarbonyl-C1 alkyl -C10 and phenyl which may be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above; R4 is hydrogen or has one of the meanings given for Rc or R4 together with R2 is a bivalent radical, which is selected from O, S, CR10 = N, N = N, 0-CR11R12, S-CR1 R12, N (R13) -CR11R12, O-C (O), O-C (S), S-C (O); N (R13) -C (0) or N (R13) -C (S); R5 is selected from the group consisting of H, alkyl d-dC haloalkyl d-Cio, cycloalkyl C3-C10, halocycloalkyl C3-C10, alkenyl d- or, haloalkenyl C2-C? 0, alkynyl C2-C? 0, haloalkynyl C2 -C, benzyl and phenyl, wherein benzyl and phenyl may be substituted with 1, 2, 3, 4 or 5 substituents Rd which are independently selected from halogen, cyano, nitro, d-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl, C3-C0 haloalkynyl, d-do alkoxy, haloalkoxy d-do, C2 alkenyl -C10-oxy, C2-C10-haloalkenyl-oxy, C2-C0-alkynyl-oxyl, C3-C10-haloalkynyl-oxy, alkyl d-C10-thio, haloalkyl d-C10-thio, alkyl d- C-io- sulfinyl, haloalkyl d-do-sulfinyl, alkyl d-do-sulfonyl, halo C 1 -C 10 -sulfonyl, hydroxy, NR 7 R 8, C 1 -C 10 alkoxycarbonyl, C 1 -Cyclohexyl haloalkoxy, alkenyl d-doxycarbonyl, C2-C10 haloalkenyl- oxycarbonyl, alkyl dC? 0 -carbonyl, haloalkyl dC 10-carbonyl and R7R8N-CO-; R6 is selected from the group consisting of H, dC 0 alkyl, which is optionally substituted with CN or N02, haloalkyl d-do, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, alkynyl C2-C10, C2-C10 haloalkynyl, alkyl dC? Oty, haloalkyl d-C10-thio, alkyl d-C ^ -sulfinyl, haloalkyl d-do-sulfinyl, alkyl d-C10-sulfonyl, haloalkyl C? -C10 -sulfonyl, d-C10-alkoxycarbonyl, wherein the alkylcarbonyl alkyl moiety may be unsubstituted or may be substituted with 1, 2 or 3 substituents selected from the group consisting of alkyl d-do-thio, phenylthio, phenyl and phenoxy, haloalcoxy d-C10-carbonium, C2-C10 alkenylcarbonyl, C2-C2alkenyl 0 -oxycarbonyl, C2-dodoxycarbonyl haloalkenyl, d-Ciocarbonyl alkyl, d-C10 haloalkylcarbonyl, hydroxyC1-C10alkyl, alkoxy dC0- alkyl d-C10, haloalkoxy dC? 0- C? -C10 alkyl, alkoxy d-do-carbonyl-C? -C10 alkyl, haloalkoxy d-C10-carbonyl-d-C10 alkyl R7R8N-CO- , benzoyl (C6H5-CO-), C3-dodocarbonylcycloalkyl, R6a-CO-, wherein R6a is C1-C4 alkoxycarbonyl, phenoxy, naphthyl or a 5- or 6-membered heterocyclic radical with 1 to 4 heteroatoms which are selected, independently of each other, from O, N and S, being possible for phenoxy, naphthyl and the 5- or 6-membered heterocyclic radical to be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Ra as defined previously, and benzyl where benzyl can be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above; R7, R8 are independently selected from H, alkyl d-do, haloalkyl d-do, cycloalkyl C3-C10, halocycloalkyl C3-C? 0, alkenyl C2-C10, haloalkenyl C2-C10, alkynyl C2- C10, C3-C10 haloalkynyl, phenyl, benzoyl, naphthyl or benzyl wherein the phenyl ring in the above-mentioned four radicals can be substituted with 1, 2, 3, 4 or 5 substituents which are selected, independently of each other, from halogen, cyano, nitro, d-do alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, alkoxy C1-C10, haloalkoxy d-C10, alkyl d-do-thio, haloalkyl dC? Otio, C? -C? Alkyl or sulfonyl, haloalkyl C? -C? O -sulfonyl, hydroxy, C1-C10 alkoxy- carbonyl, haloalkoxy d-C10-carbonyl, alkenyl C2-do-oxycarbonyl, haloalkenyl C2-C? 0-oxycarbonyl, alkyl d-Cio-carbonyl and haloalkyl d-Cyclocarbonyl; R 9 is hydrogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 0 halocycloalkyl, C 2 -C 10 alkenyl, C 2 -C 0 haloalkenyl, C 2 -C 10 alkynyl, C 3 -C 10 haloalkynyl, haloalkyl. dC? 0-sulfonyl, C 1 -C 10 alkylcarbonyl, haloalkyl d-Ciocarbonyl, R 7 R 8 N -CO-, phenyl, benzoyl, naphthyl or benzyl, wherein the phenyl ring in the above-mentioned four radicals can be substituted with 1 , 2, 3, 4 or 5 substituents Rb; and R10 is hydrogen or has one of the meanings given for Rc; R11, R12 are independently selected from H, d-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C20 alkenyl, C2-C10 haloalkenyl, C2- alkynyl C10 and haloalkynyl C3-C0, alkoxy d-Cic haloalkoxy d-C10, alkyl d-C10-thio, haloalkyl dC? 0-thio, hydroxy-C1-C10 alkyl, alkoxy d-do-alkyl d-C10, halo- C1-Cι-C 1 -C 10 alkoxy, d-C 1 -C 10 alkoxy-C 1 -C 10 -alkyl, d-C 1 -C 10 -haloalkoxy-C 1 -C 10 -alkyl, one of the radicals R 11 or R 12 can also be alkyl d -do-sulfonyl, d-C10 haloalkyl sulfonyl, d-doxycarbonyl alkoxy, d-C10 haloalkoxycarbonyl, C2-C10 alkenyl-oxycarbonyl, C2-C10 haloalkenyl-oxycarbonyl, d-C10 alkylcarbonyl, haloalkyl d-do-carbonyl or R7R8N-CO-. R 13 is hydrogen, cyano, d-do alkyl, d-C 10 haloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 0 halocycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkenyl, alkynyl C2-C10, C3-C10 haloalkynyl, haloalkyl d-do-sulfonyl, alkyl d-C10-carbonyl, haloalkyl C? -C? Or -carbonyl, R7R8N-CO-, phenyl or benzyl, wherein phenyl and benzyl may be substituted with 1, 2, 3, 4 or 5 substituents Rb; or one of its salts. 2. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein Ar in the formula I is phenyl, which is unsubstituted or is substituted by 1 , 2, 3 or 4 Rc radicals as defined above. 3. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein X in the formula I is C = 0. 4. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein A in the formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl and pyridazinyl and wherein the cyclic radical can be substituted with 1, 2 or 3 substituents Ra as defined above. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein A in the formula I is a cyclic radical selected from phenyl, thienyl, and pyridyl , where the cyclic radical can be substituted with 1, 2 or 3 substituents Ra which are selected, independently of one another, of halogen, d-C4 alkyl, C? -C alkoxy, d-C4 haloalkoxy and C1-C4 haloalkyl. 6. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein A in the formula I is 2-thienyl which may be substituted with 1, 2 or 3 substituents Ra which are independently selected from each other of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and haloalkyl dC. 7. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein Q in the formula I is selected from a single bond, -CH2-, 0 -CH2-, -S-CH2-, -0-CH (CH3) - and -S-CH (CH3) -. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, where Q and A are together alkyl d-d0 which may be substituted with 1 or 2 substituents selected from the group consisting of = 0, OH and d-C2 alkoxy. . The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R1 is selected from the group consisting of d-Cio hydrogenalkyl and d-C? 0 haloalkyl. 0. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R2 in the formula I is selected from hydrogen, halogen and dC4 alkyl. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R3 in the formula I is selected from hydrogen, halogen and alkyl d- d . 12. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R3 in the follula I is hydrogen. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R 4 is hydrogen or a radical Rc as defined above. 14. The method according to claim 13, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein Ar is phenyl, which is unsubstituted or is substituted by 1, 2 or 3 radicals Rc which are independently selected from halogen, CN, dd alkyl, Ci-d alkoxy, d-C4 haloalkoxy and d-C4 haloalkyl. 15. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R4 together with R2 is -0-. 16. The method according to claim 15, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein Ar in the fistula I is phenyl, which is unsubstituted or which can carry 1. , 2 or 3 Rc radicals which are selected, independently of each other, from halogen, CN, C1-C4 alkyl, dC alkoxy, d-C4 haloalkoxy and d-C4 haloalkyl. 17. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, in where R5 is selected from the group consisting of H, alkyl d-do, haloalkyl d-C10, cycloalkyl C3-C? or, halocycloalkyl C3-C10, alkenyl C2-C10, haloalkenyl C2-C? 0. The method according to claim 1, wherein the compounds of the general formula I are selected from compounds or a salt thereof, wherein R6 is hydrogen. The method according to claim 1, wherein the pests are insects. A method to protect crops from an attack or infestation of selected pests of insects, arachnids and nematodes, comprising contacting a crop with a pesticidally effective amount of at least one compound of formula I as defined in claim 1 or with one of its salts. A method for protecting inanimate materials from attack or infestation of selected pests of insects, arachnids and nematodes, comprising contacting the inanimate material with a pesticidally effective amount of at least one compound of the formula I as defined in claim 1 or with one of its salts. A hydrazide compound of the general formula I according to claim 1 or a salt thereof, except for the compounds of the formula I, wherein A and Ar are unsubstituted phenyl, Q is a single bond, X is C = 0 and R1, R2, R3, R4, R5 and R6 are hydrogen; or A and Ar are unsubstituted phenyl, Q is a single bond, X is C = 0, R1 is CH2- CH = CH2 or C6H5 and R2, R3, R4, R5 and R6 are hydrogen; or Ar is unsubstituted phenyl, A together with Q is CH3, X is C = 0, R1 is hydrogen, CH3 or C6H5 and R2, R3, R4, R5 and R6 are hydrogen; or Ar is unsubstituted phenyl, A is 4-methylphenyl, Q is a single bond, X is S02, R1 is (CH2) 3CH3 and R2 is methyl, R3, R4, Rs and R6 are hydrogen; or Ar is unsubstituted phenyl, A is 4-methylphenyl, Q is a single bond, X is S02, R1 is C6H5 or CH3 and R2, R3, R4, R5 and R6 are hydrogen; or A is 5-methyl-3-phenylisoxazol-4-yl, Ar is pyridin-2-yl, Q is a single bond, X is C = 0, R1 is methyl and R2, R3, R4, R5 and R6 are hydrogen; or Ar is unsubstituted phenyl, X is C = S, R1 is methyl, R2 together with R4 is CH = N, R3, R5 and R6 are hydrogen and A together with Q form a radical that is selected from the group consisting of NHCH2 (C6H5), N (CH3) 2, pyrrolidin-1-yl, 4- methylpiperidin-1-yl, 4-phenylpiperidin-1-yl, 4-ethoxycarbonylpiperazin-1-yl and 2,6-dimethylmorpholin-4-yl. A hydrazide compound of the general formula I or a salt thereof, wherein A, X, Ar, R2, R3, R4, R5, R6, R7, R8, R9, R10, R1, R12 and R13 have one of the meanings given in claim 1, R1 is hydrogen and Q is selected from the group consisting of a single bond, alkylidene C1-C4, O-alkylidene C? -C, S-alkylidene d-C4 and NR9-alkylidene C? -C4, wherein the alkylidene group in the last four mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 substituents selected from OH, = 0, halogen, haloalkyl C -, - C4 and alkoxy d-C4; except for compounds of the formula I, wherein A and Ar are unsubstituted phenyl, Q is a simple bond, X is C = 0 and R1, R2, R3, R4, R5 and R6 are hydrogen. The compound according to claim 22 or 23, wherein A is a cyclic radical selected from phenyl and a heterocyclic radical of 5 or 6 members with 1 to 4 heteroatoms that are selected, independently of each other, from O, N and S, and where the cyclic radical can have 1, 2, 3, 4 or 5 Ra substituents that are selected, independently from each other yes, of halogen, cyano, nitro, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, alkenyl C2-C10, C2-C10 haloalkenyl, C-C10 alkynyl, C3-C10 haloalkynyl, d-haloalkoxy C-? -10 C alkoxy, C2-C10 alkenyl-oxy, C2-C10 haloalkenyl-oxy, C2-C20 alkynyl -oxi, C3-C10 haloalkynyl-oxy, C? -C10 alkylthio, haloalkyl d-do-thio, C? -C10 alkyl sulfinyl, haloalkyl d-do sulfinyl, alkyl dCylosulfonyl, haloalkyl d-? do-sulfonyl, hydroxy, NR7R8, C1-C10 alkoxycarbonyl, haloalkoxy d-C10-carbonyl, C2-C6 alkenyl or oxycarbonyl, C2-C10 haloalkenyl-oxycarbonyl, C6-C6 alkyl or carbonyl, haloalkyl d- C10-carbonyl, R7R8N-CO-, phenyl, benzyl and phenoxy, in which phenyl, benzyl and phenoxy can be substituted with 1, 2, 3, 4 or 5 substituents Rb which are selected, independently of each other , of halogen, cyano, nitro, d-C10 alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C2 alkynyl, C3-C10 haloalkynyl, C 1 -C 10 alkoxy, d-C 10 haloalkoxy, C 6 -do-oxy alkenyl, C 2 -C 0 haloalkenyl 0-oxy, alkynyl C 2-C10-oxy, haloalkynyl C3-C10-oxy, alkyl d-do-thio, haloalkyl d-C10-thio, alkyl d-C10-sulfinyl, C -C10 haloalkyl sulfinyl, C? -C10 alkyl sulphonyl, C? -C10 haloalkyl sulfonyl, hydroxy, NR7R8, d-Cio-carbonyl alkoxy, d-C10 haloalkoxycarbonyl, C2-C10 alkenyl-oxycarbonyl, haloalkenyl C2 -C? 0-oxycarbonyl, alkyl dC? O-carbonyl, haloalkyl C? -C? O -carbonyl and R7R8N-CO-, in which two radicals Ra which are bonded to adjacent carbon atoms can form a rest CH = CH-CH = CH or a residue 0-CH2-0, where in these two residues 1 or 2 hydrogen atoms can be replaced by a radical Rb as defined above; Ar is an aromatic radical selected from phenyl, naphthyl, pyridyl, pyrimidyl, furyl and thienyl, wherein the aromatic radical can carry 1, 2, 3, 4 or 5 substituents Rc which are independently selected from halogen, cyano , nitro, C1-C10 alkyl, haloalkyl d-do, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C2-C10 alkynyl, C3-C10 haloalkynyl, d-C10 alkoxy, haloalkoxy C1 -C10, C2-C alkenyl 0-oxy, C2-C10 alkynyloxy, haloalkynyl C3-do-oxy, alkyl d-do-thio, haloalkyl d-C10-thio, C1-C10 alkyl sulfinyl, haloalkyl d -C10- sulfinyl, alkyl d-C10-sulfonyl, haloalkyl C? -C10-sulfonyl, hydroxy, NR7R8, alkoxy d-do-carbonyl, haloalkoxy C? -C? 0 -carbonyl, C2-C10 alkenyl-oxycarbonyl, haloalkenyl C2 -C? 0-oxycarbonyl, alkyl dC? O-carbonyl, haloalkyl C? -C? O -carbonyl, R7R8N-CO-, phenyl, benzyl and phenoxy, in which phenyl, benzyl and phenoxy can be unsubstituted or they can be substituted with 1, 2, 3, 4 or 5 Rb substituents as defined above; R1 is selected from the group consisting of H, d-C10 alkyl, d-Cio haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2-C20 alkenyl, C2-C10 haloalkenyl, C2-C0 alkynyl and haloalkynyl C2 -C10; R6 is selected from the group consisting of H, alkyl dC 0, which is optionally substituted with CN or N02, haloalkyl d-C10, cycloalkyl C3-C10, halocycloalkyl C3-C? 0, alkenyl C2-C? Or, haloalkenyl C2 -C10, C2-C10 alkynyl, C2-C10 haloalkynyl, alkyl d-do-sulfinyl, C1-C10 haloalkylsulfinyl, alkyl d-do-sulfonyl, haloalkyl dC 0 -sulfonyl, d-C10 alkoxycarbonyl, haloalkoxy C -C-C10-carbonyl, C2-C10-alkenyl-oxycarbonyl, C2-C10-haloalkenyl-oxycarbonyl, d-C10-alkylcarbon, d-C10-haloalkylcarbonyl, hydroxy-C1-C10alkyl, d-C10-alkyloxy the d-dc haloalkoxy d-Cio-d-C10 alkyl, d-C10 alkoxy-carbonyl-d-dc alkyl halo- C10 alkoxy-carbonyl-d-C10 alkyl R7R8N-CO- and benzyl wherein benzyl can be substituted with 1, 2, 3, 4 or 5 R substituents as defined above; and R7, R8 are selected, independently from each other, of H, C-Cι alkyl, d-Cιhaloalkyl, C 3 -C 10 cycloalkyl, C 3 -C 0 halocycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkenyl, C 2- alkynyl C10, C3-C10 haloalkynyl, phenyl or benzyl in which phenyl and benzyl can be substituted with 1, 2, 3, 4 or 5 substituents which are independently selected from halogen, cyano, nitro, alkyl dC? 0, haloalkyl d-C10, cycloalkyl C3-C10, halocycloalkyl C3-C10, alkenyl C2-C10, C2-C10 haloalkenyl, C1-C10 alkoxy, C1-C10 haloalkoxy, alkyl cyclo-thio, haloalkyl C? -C? O-thio, C? -C? Alkyl or sulfonyl, C1-C10 haloalkyl - sulfonyl, hydroxy, C?-C?-alkoxy or -carbonyl, haloalkoxy d-Cι-carbonyl, C 2 -C 10 -alkenyl-oxycarbonyl, C 2 -C 10 -haloalkenyl-oxycarbonyl, alkyl d-do-carbonyl and haloalkyl d-C 10 -carbonyl the. The compound according to one of claims 22 or 23, wherein Ar in the formula I is phenyl, which is unsubstituted or which is substituted with 1, 2, 3 or 4 Rc radicals as defined above. The compound according to one of claims 22 or 23, wherein X in formula I is C = 0. The compound according to one of claims 22 or 23, wherein A in the formula I is a cyclic radical selected from phenyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoloyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl and wherein the cyclic radical can be substituted with 1, 2 or 3 substituents Ra as defined above. The compound according to one of claims 22 or 23, wherein A in the formula I is a cyclic radical selected from phenyl, thienyl, and pyridyl, wherein the cyclic radical may be substituted with 1, 2 or 3 substituents Ra are selected, independently from each other, from halogen, C1-C4 alkyl, d-C4 alkoxy, haloalkoxy d-C4 and haloalkyl d-C4. The compound according to one of the claims 22 or 23, wherein A in the follula I is 2-thienyl which can be substituted with 1, 2 or 3 substituents Ra which are selected, independently of each other, from halogen, C 1 -C 4 alkyl, C 4 alkoxy, haloalkoxy d 4 and haloalkyl d 4 C 4. 0. The compound according to one of claims 22 or 23, wherein Q in formula I is selected from a single bond, -CH2-, 0-CH2-, -S- CH2-, -0-CH (CH3) - and -S-CH (CH3) -. 31. The compound according to claim 22, wherein Q and A are d-C10 alkyl together which may be substituted with 1 or 2 substituents selected from the group consisting of = 0, OH and C1-C2 alkoxy. 32. The compound of the general formula I according to claim 22 or a salt thereof, wherein R1 is selected from the group consisting of C9-C10 hydrogen-alkyl and d-C10 haloalkyl. 33. The compound according to one of claims 22 or 23, wherein R2 in formula I is selected from hydrogen, halogen and C?-C4 alkyl. 34. The compound according to one of claims 22 or 23, wherein R3 in formula I is selected from hydrogen, halogen and C? -C4 alkyl. 35. The compound according to one of claims 22 or 23, wherein R3 in formula I is hydrogen. 36. The compound according to one of claims 22 or 23, wherein R4 is hydrogen or a radical Rc as defined above. 37. The compound according to claim 36, wherein Ar is phenyl, which is unsubstituted or substituted by 1, 2 or 3 Rc radicals which are independently selected from halogen, CN, alkyl C? -C4, d-C4 alkoxy, C? -C haloalkoxy and C1-C4 haloalkyl. 38. The compound according to one of claims 22 or 23, wherein R4 together with R2 is -O-. 39. The compound according to claim 38, wherein Ar in formula I is phenyl, which is unsubstituted or which can carry 1, 2 or 3 Rc radicals which are independently selected from halogen, CN, d-C4 alkyl, alkoxy d- C4, haloalkoxy C? -C and haloalkyl dC. 40. The compound according to one of claims 22 or 23, wherein R5 is selected from the group consisting of H, d-Cio alkyl, d-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C2 alkenyl. -C10, haloalkenyl 41. The compound according to one of claims 22 or 23, wherein R6 is hydrogen. 42. A composition for combating selected pests of insects, arachnids and nematodes, comprising an amount of pesticidal efficacy of at least one composed of the general formula I according to one of claims 22 or 23 and at least one inert carrier and / or at least one surfactant.
MX2007006538A 2004-12-01 2005-11-30 Hydrazide compounds for combating animal pests. MX2007006538A (en)

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