BRPI0712923A2 - anthranilic acid diamide derivatives with heteroaromatic and heterocyclic substituents - Google Patents

Abstract

DIAMIDE DERIVATIVES OF ANTHRANILIC ACID WITH HETEROAROMATIC AND HETEROCYCLIC SUBSTITUTES. The present invention relates to new insecticides of formula (I), in which R1, R2, R3, R4, R5, R6, A, Q and n can have the meanings mentioned in the specification, several processes for their preparation and their use as active substances, especially their use as pesticide compositions.

Description

Patent Descriptive Report for "anthranilic acid diamide derivatives with heteroaromatic and heterocyclic substituents".

The present invention relates to novel insecticides, various processes for their preparation and their use as active substances, especially their use as pesticide compositions.

It is well known that certain anthranilamides (e.g., WO 01/70671, WO 03/015519, WO 03/016284, WO 03/015518, WO 03/024222, WO 03/016282, WO 03/016283, WO 03/062226 , WO 03/027099, WO 04/027042, WO 04/033468, WO 2004/046129, WO 2004/067528, WO 2005/118552, WO 2005/077934, WO 2005/085234, WO 2006/023783, WO 2006/000336 , WO 2006/040113, WO 2006/111341, WO 2007/006670, WO 2007/024833, WO 2007/020877) have insecticidal properties. The effectiveness of these substances is good, but in some cases is lacking.

New anthranilamides of formula (I) have been developed.

<formula> formula see original document page 2 </formula> in which

R1 represents hydrogen, amino, hydroxy or C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl in each case optionally substituted one or more times, the same or different, wherein the independent substituents from each other can be selected from halogen, cyano, nitro, hydroxy, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, (C1-C4-alkoxy) carbonyl, C1 -C4-alkylamino, di- (C1-C4-alkyl) amino, C3-C6-cycloalkylamino or (C1-C4-alkyl) C3-C6-cycloalkylamino, R2 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl , C2-C6-

alkynyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylamino, di (C1-C4-alkyl) amino, C3-C6-cycloalkylamino, C2-C6-alkoxycarbonyl or C2-C6-alkylcarbonyl,

R3 represents hydrogen or C1 -C6 alkyl, C1 -C6 alkoxy, C2 -C6 alkenyl, C2 -C6 alkynyl in each case optionally substituted one or more times, the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C 1 -C 4 alkylsulfinino, C 1 -C 4 alkylsulfimino-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinino-C 2 -C 5 alkylcarbonyl, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoxim-C 2 C5-alkylcarbonyl, C2-C6-alkoxycarbonyl, C2-C6-alkylcarbonyl or C3-C6-trialkylsilyl

R 3 further represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl in each case optionally substituted one or more times, the same or different, wherein the substituents independently of one another may be selected from amino, C3 -C6 cycloalkylamino or a 5- or 6-membered heteroaromatic ring,

R3 likewise furthermore represents C3 -C12 cycloalkyl, C3 -C12 cycloalkyl C1 -C6 alkyl and C4 -C12 bicycloalkyl, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, amino, C1 -C6 alkyl, C3 -C6 cycloalkyl, C3 -C6 cycloalkylamino, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfonyl, C1 -C4 C 1 -C 4 alkylsulfinimino, C 1 -C 4 alkylsulfinino C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinino C 2 -C 5 alkylcarbonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkylC 2 -C 5 alkylcarbonyl C6-alkoxycarbonyl, C2-C6-alkylcarbonyl, C3-C6-trialkylsilyl or a 5- or 6-membered heteroaromatic ring,

R 2 and R 3 together may be bonded through two to six carbon atoms and form a ring, which may further contain another nitrogen, sulfur or oxygen atom and may eventually be substituted one to four times with C1 -C2 alkyl, halogen, cyano, amino or C1 -C2 alkoxy,

R21R3 further together represent = S (C1 -C4 alkyl) 2, = S (O) (C1 -C4 alkyl) 2,

R4 represents hydrogen, halogen, cyano, nitro, C1 -C4 alkyl, C1 -C4 haloalkyl, C2 -C6 alkenyl, C2 -C6 haloalkenyl, C2 -C6 alkynyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, SF5, C1 -C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, di- (C1-C4-alkyl) amino, C3- C6-cycloalkylamino, (C1-C4-alkoxy) imino, (C1-C4-alkyl) (C1-C4-alkoxy) imino, (C1-C4-haloalkyl) (C1-C4-alkoxy) imino or Cs-C6-trialkylsilyl or

two R4, through adjacent carbon atoms, form a ring representing - (CH2) 3-, - (CH2) 4-, - (CH2) 5-, - (CH = CH-) 2-, -OCH2O- , -O (CH2) 2O-, -OCF2O-, - (CF2) 2O-, -O (CF2) 2O-, - (CH = CH-CH = N) - or - (CH = CH- N = CH) -,

two R4's, furthermore, through adjacent carbon atoms, form the following ring-rings, which may be substituted one or more times, the same or different, wherein the substituents independently of one another may be selected from hydrogen, CrC6. C 1 -C 6 -cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, halogen, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio (C 1 -C 6 alkyl), C 1 -C 4 alkylsulfinyl (C 1 -C 6 alkyl) C 1 -C 4 alkylsulfonyl (C 1 -C 6 alkyl), C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino or C 3 -C 6 cycloalkylamino,

<formula> formula see original document page 4 </formula>

η represents O to 3, R5 represents C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C6 haloalkyl, C1 -C6 halocycloalkyl, C2 -C6 alkenyl, C2 -C6 haloalkenyl, C2 -C6 alkynyl, C2 -C6 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, halogen, cyano, C6-trialkylsilyl,

R6 represents hydrogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C6 cycloalkyl, C1 -C6 haloalkyl, C2 -C6 haloalkenyl or

<formula> formula see original document page 5 </formula>

R6 further represents C3 -C6 cycloalkoxy,

R 7 independently of each other represents hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 -haloalkylthio,

m represents 0 to 4,

X represents N, CH, CF, CCI, CBr or Cl,

A represents -CH 2 -, -CH 2 O-, -CH 2 OCH 2 -, -CH 2 S-, -CH 2 SCH 2 -, -CH 2 N (C 1 -C 6 alkyl) -, -CH 2 N (C 1 -C 6 alkyl) CH 2 -, -CH [C 2 -C 11 C6-alkyl) -, -CH (CN) -, -CH (C1 -C6 -alkyl) -, -C (di-C1 -C6 -alkyl) -, -CH2CH2- or -C = NO (C1-C6-alkyl) - ,

Q represents a 5 or 6 membered heteroaromatic ring or an 8, 9 or 10 membered aromatic ring heterobicyclic ring system, wherein the ring or ring system is optionally substituted one or more times, the same or different and in whereas substituents independent of each other may be selected from hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 C 1 -C 8 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1 -C4-alkoxy, C1 -C4-haloalkoxy, C1 -C4-alkylthio, C1 -C4-alkylsulfonyl, C1-C4-haloalkyl, C1 -C4-haloalkyl C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, di (C 1 -C 6 alkyl) amino, C 3 -C 6 cycloalkylamino, (C 1 -C 6 alkyl) carbonyl, (C 1 -C 6 alkoxy) carbonyl, (C 1 -C 6 alkyl) aminocarbonyl, di- (C1 -C4 alkyl) aminocarbonyl, tri- (C1 -C2) alkylsilyl, (C1 -C4 alkyl) (C1 -C4 alkoxy) imino,

Q further represents a 5- or 6-membered heteroaromatic or heterocyclic ring or an 8, 9 or 10-membered aromatic ring heterobicyclic ring system, wherein the ring or ring system is optionally substituted one or more times by or different and wherein the substituents independent of each other may be selected from hydrogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C6 cycloalkyl, C1 -C6 haloalkyl, C2- C6-Allylalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1-C4-alkoxy, C1 -C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfinyl alkylsulfonyl, C1 -C4 haloalkylthio, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl, C1 -C4 alkylamino, di (C1 -C4 alkyl) amino, (C3 -C6 alkyl) carbonyl, (C1 -C6 alkoxy) carbon C6-alkyl) aminocarbonyl, di (C1 -C4 -alkyl) aminocarbonyl, tri- (C1-C2) alkylsilyl, (C1-C4-alkyl) (C1-C4-alkoxy) imino,

or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein the phenyl or ring may optionally be substituted one or more times, the same or different with C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, halogen, CN, NO 2, OH, C1 -C4 alkoxy, C1 -C4 haloalkoxy,

The compounds of formula (I) further comprise N-oxides and salts.

Finally, it has been found that the compounds of formula (I) according to the invention have very good insecticidal properties and can be used both to protect plants and to protect materials against unwanted parasites such as insects. .

The compounds according to the invention may optionally be present as mixtures of various possible isomeric forms, especially stereoisomers such as, for example, E and Z isomers, threo and erythro, as well as optical isomers, but optionally. also of tautomers. Both E and Z isomers, as well as threo and erythro isomers as well as optical isomers, desired mixtures of these isomers as well as possible tautomeric forms are claimed.

Anthanilamides according to the invention are generally defined by formula (I). Preferred radical definitions of the formulas mentioned above and below are mentioned below. These definitions apply to the end products of formula (I), as do all intermediate products.

R 1 preferably represents hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkynyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, cyano (C 1 -C 6 alkyl), C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkyl, C 1 -C 4 -alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl or C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl.

R1 is particularly preferably hydrogen, methyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl.

R1 most particularly preferably represents hydrogen.

R2 preferably represents hydrogen or C1 -C6 alkyl.

R 2 particularly preferably represents hydrogen or

methyl,

R 2 very particularly preferably represents hydrogen.

R 3 preferably represents hydrogen or C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein the substituents independently of one another may be selected from halogen, cyano, nitro, hydroxy, C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfimino, C1 -C4 alkylsulfimino-C1 -C4 C 1 -C 4 alkylsulfinino-C 2 -C 5 alkylcarbonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximino-C 2 -C 5 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl C3 -C6 alkylcarbonyl or trialkylsilyl,

R 3 further preferably represents C 3 -C 12 cycloalkyl and C 4 -Ccybicycloalkyl, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 C 1-4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinino-C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinino-C 2 -C 5 alkylcarbonyls, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximine C 2 -C 5 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl or C 3 -C 6 trialkylsilyl,

R 3 is particularly preferably hydrogen or C 1 -C 6 alkyl, C 1 -C 6 alkoxy optionally substituted one or more times each time, the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfimino, C1 -C4 alkylsulfimino-C1 -C4 alkyl C 1 -C 4 alkylsulfimino-C 2 -C 5 alkylcarbonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylsulfoximino C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximino-C 2 -C 5 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 C3 -C6 alkylcarbonyl or trialkylsilyl,

R3 furthermore particularly preferably represents optionally substituted one or more times, one or more times, the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C6 -alkyl. C 1 -C 6 alkylcycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinino, C 1 -C 4 alkyls C 1 -C 4 alkyl C 2 -C 5 alkylsulfimino C 1 -C 6 alkylcarbonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylsulfoximino C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximino C 2 -C 5 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl -C6-trialkylsilyl,

R3 most particularly preferably represents C1 -C4 alkyl (methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or tert-butyl) or cyano-C1-C3-alkyl (cyanomethyl, 1-cyanomethyl, 2-cyanoethyl, 1-cyano-n-propyl, 2-cyano-n-propyl, 3-cyano-n-propyl, 1-cyano-isopropyl, 2-cyano-isopropyl).

R3 is especially preferably methyl, isopropyl or cyanomethyl.

R4 preferably represents hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, halogen, cyano, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio or C1 -C4 haloalkylthio.

In addition, preferably two adjacent R4 radicals represent - (CH2) 3-, - (CH2) 4-, - (CH2) 5-, - (CH = CH-J2-, -OCH2O-, -O (CH2) 2O-, -OCF 2 O-, (CF 2) 2 O-, -O (CF 2) 2 O-, - (CH = CH-CH = N) - or - (CH = CH-N = CH) -.

R4 is particularly preferably hydrogen, C1 -C4 alkyl, C1 -C2 haloalkyl, halogen, cyano or C1 -C2 haloalkoxy.

In addition, particularly preferably, two adjacent R4 radicals represent - (CH2) 4-, - (CH = CH-) 2-, -O (CH2) 2O-, -O- (CF2) 2O-, (CH = CH-CH = N) - or - (CH = CH-N = CH) -

R4 most particularly preferably represents hydrogen, methyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, iodine or trifluoromethoxy. Furthermore, most particularly preferably, two adjacent R4 radicals represent - (CH2) 4- or - (CH = CH-) 2-.

R4 especially preferably represents chlorine or bromine.

R4 furthermore preferably represents iodine or cyano. In addition, two adjacent R4 radicals particularly preferably represent - (CH = CH-) 2-.

R5 preferably represents C1 -C4 alkyl, C3 -C6 cycloalkyl, C1 -C4 haloalkyl, C1 -C6 halocycloalkyl, C2 -C6 alkenyl, C2 -C6 haloalkenyl, C2 -C4 alkynyl, C2 -C4 haloalkyl, C1 -C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, halogen, cyano, C3-nitro -trialkylsilyl.

R5 is particularly preferably C1 -C4-alkyl, C3 -C6 -C1C16a-alkyl, C1 -C4 -haloalkyl, C1-C6-halocycloalkyl, C2-C6-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, fluoro, chloro, bromo, iodo, cyano, nitro or C 5 -C 6-trialkylsilyl.

R5 most particularly preferably represents methyl, fluorine, chlorine, bromine or iodine.

R5 especially preferably represents methyl or chlorine.

R6 preferably represents C1 -C6 alkyl or

<formula> formula see original document page 10 </formula>

R 6 further preferably represents C 3 -C 6 cycloalkoxy,

R6 particularly preferably represents methyl or

<formula> formula see original document page 10 </formula>

R7 independently of one another preferably represents hydrogen, halogen, cyano, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkoxy, C1 -C4 haloalkylsulfonyl or (C1 -C4 alkyl) C1 -C4 alkoxyimino,

R7 independent of each other, particularly preferably represents hydrogen, halogen or C1 -C4 haloalkyl,

R7 most particularly preferably represents fluorine, chlorine or bromine,

R7 represents especially preferably chlorine,

m preferably represents 1, 2 or 3,

m is particularly preferably 1 or 2,

m very particularly preferably represents 1,

X preferably represents N, CH, CF, CCI, CBr or Cl,

X is particularly preferably N, CH, CF, CCI or CBr,

X is most particularly preferably N, CCI or CH.

A preferably represents -CH2-, -CH2O-, -CH2OCH2-, -CH2S-

, -CH 2 SCH 2 -, -CH 2 N (C 1 -C 6 alkyl) -, -CH 2 N (C 1 -C 6 alkyl) CH 2 -, -CH (CN) -, - CH (C 1 -C 6 alkyl) -, -C (di-C 1 -C 6 alkyl) - , -CH 2 CH 2 -, -C = NO (C 1 -C 6 alkyl) -,

A particularly preferably represents -CH 2 -, -CH (CH 3) 1 C (CH 3) 2 or CH 2 CH 2,

Moreover, it particularly particularly represents - CH (CN) -,

A is very particularly preferably CH2 or CH (CH3),

Q preferably represents a 5- or 6-membered aromatic heterocyclic ring optionally substituted one or more times from the Q-1 to Q-53 series or a 9-membered aromatic ring heterobicyclic ring system Q-54 to Q-56, wherein the substituents independently of one another can be selected from C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C2 alkoxy, halogen, cyano, hydroxy, nitro or C1 -C2 haloalkoxy.

Q further preferably represents a 5- or 6-membered aromatic heterocyclic ring optionally substituted one or more times from the Q-1 to Q-53 and Q-54 to Q-59 series, an aromatic annular ring heterobicyclic ring system 9-membered Q-54 through Q-56, as well as a 5-membered heterocyclic ring Q-60 through Q-61, wherein the substituents independently of one another may be selected from C1 -C3 alkyl, C1 -C3- haloalkyl, C1 -C2 alkoxy, halogen, cyano, hydroxy, nitro or C1 -C2 haloalkoxy, or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring wherein the phenyl or the ring may optionally be substituted one or more times, the same or different with C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C6 cycloalkyl, C1 -C6 haloalkyl, C2- C6-haloalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, NO2, OH, C1-C4-alkoxy, C1-C4-haloalkoxy,

Q particularly preferably represents a 5- or 6-membered aromatic heterocyclic ring optionally substituted one or more times from the Q-36 to Q-40 series or a 9-membered aromatic ring heterobicyclic ring system Q-54 to Q-56 wherein the substituents independent of each other may be selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 2 alkoxy, halogen, cyano, hydroxy, nitro or C 1 -C 2 haloalkoxy.

Q further particularly preferably represents a 5- or 6-membered aromatic heterocyclic ring optionally substituted one or more times from the Q-36 to Q-40 and Q-58 to Q-59 series, an aromatic ring-heterocyclic aromatic ring system. 9-member Q-54 through Q-56, as well as a 5-membered heterocyclic ring Q-60 through Q-61, wherein the independent substituents may be selected from C1-C3-alkyl, C1-C3 -haloalkyl, C1 -C2 alkoxy, halogen, cyano, hydroxy, nitro or C1 -C2 haloalkoxy, or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring may optionally be substituted one or more times, the same or different with C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, NO2, C1-C4-alkoxy, C1-C4-haloalkoxy,

Q most particularly preferably represents an aromatic heterocyclic ring optionally substituted one or more times from the Q-37, Q-38, Q-39, Q-40, Q-58 and Q-59 series, as well as a 5-membered heterocyclic ring. Q-60 members, wherein the substituents independently of one another may be selected from C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C2 alkoxy, halogen, cyano, hydroxy, nitro or C1 -C2 haloalkoxy,

or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein the phenyl or ring may optionally be substituted one or more times, the same or different with CrC6- alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkyl, C 3 -C 6 -halocycloalkyl, halogen, CN, NO 2, C1 -C4 alkoxy, C1 -C4 haloalkoxy,

Q more particularly preferably represents an aromatic heterocyclic ring optionally substituted one or more times from the Q-37, Q-38, Q-39, Q-40, Q-58 and Q-59 series, as well as a 5-membered 5-membered heterocyclic ring Q-60, wherein substituents independent of each other may be selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, cyano, nitro or C 1 -C 2 haloalkoxy,

or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein the phenyl or ring may optionally be substituted one or more times, the same or different with CrC6- alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, halogen, CN, NO 2, C1 -C4 alkoxy, C1 -C4 haloalkoxy,

Q is especially preferably an aromatic heterocyclic ring, optionally substituted once, twice or three times by carbon atoms Q-37, Q-40, Q-58 and Q-59, as well as a 5-membered heterocyclic ring. Q-60 members, as well as a 5-membered Q-60 heterocyclic ring, wherein the substituents independent of each other may be selected from chlorine, fluorine, iodine, bromine, cyano, trifluoromethyl and pentafluoroethyl,

or wherein the substituents independent of each other may be selected from phenyl, wherein the phenyl ring may optionally be substituted one or more times, the same or different with C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C2-C6-Squinyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, NO2, C1-C4-haloalkoxy,

Q furthermore particularly preferably represents an aromatic heterocyclic ring optionally substituted one or more times from the Q-37, Q-40, Q-58 and Q-59 series, as well as a five-membered heterocyclic ring Q-60 in whereas substituents independent of each other may be selected from chlorine, fluorine, iodine, cyano, trifluoromethyl and pentafluoroethyl,

or wherein the substituents independent of each other may be selected from phenyl, wherein the phenyl ring may optionally be substituted one or more times, the same or different with chlorine, fluorine, iodine,

bromine, cyan, trifluoromethyl and pentafluoretyl,

<formula> formula see original document page 14 </formula> Emphasis is placed on the compounds of formula (1-1)

<formula> formula see original document page 15 </formula>

wherein R1, R21 R3, R41 R51 R71 A1 Q and X have the general, preferred, particularly preferred, very particularly preferred and especially preferred meanings mentioned above.

Halogen substituted radicals, for example haloalkyl, are halogenated one or more times to as many substituents as possible. In multiple halogenation, halogen atoms may be equal or different. In this case, halogen represents fluorine, chlorine, bromine or iodine, especially represents fluorine, chlorine or bromine.

Particularly preferred, particularly particularly preferred and especially preferred, compounds are compounds, which in each case carry the substituents mentioned as being preferred, particularly preferred, very particularly preferred and especially preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, also together with heteroatoms, such as, for example, in alkoxy, where possible, may in each case be straight chain or branched.

Optionally substituted radicals may be substituted one or more times, and in multiple substitutions the substituents may be the same or different.

The definitions of radicals or elucidations generally cited above or in the preferred scopes, however, may also be arbitrarily combined with each other, that is, between their respective scopes and preferred scopes. They are valid for end products as well as correspondingly for pre-products and intermediate products. 15

Furthermore, it has been found that anthranilamides of formula (I) are obtained by one of the following processes.

Anthanilamides of formula (I)

<formula> formula see original document page 16 </formula>

wherein A, R11 R2, R31 R4, R51 R6, Q and η have the meanings mentioned above are obtained

(A) reacting anilines of formula (II)

<formula> formula see original document page 16 </formula>

wherein A, R1, R2, R3, R4, R5 and η have the meanings mentioned above with carboxylic acid chlorides of formula (III)

<formula> formula see original document page 16 </formula>

wherein R6, A and Q have the meanings mentioned above, in the presence of an acid binding agent, (B) reacting anilines of formula (II)

<formula> formula see original document page 16 </formula>

wherein A, R1, R2, R3, R4, R5 and η have the meanings mentioned above, with a carboxylic acid of formula (IV)

<formula> formula see original document page 17 </formula>

wherein R6, A and Q have the meanings mentioned above, in the presence of a condensing agent or wherein

(C) for the synthesis of anthranilamides of formula (I), wherein R1 represents hydrogen, benzoxazinones of formula (V) are reacted. <formula> formula see original document page 17 </formula> wherein R4 R5, R6, A , Q and η have the meanings mentioned above with an amine of formula (XV)

<formula> formula see original document page 17 </formula>

wherein R2 and R3 have the meanings mentioned above, in the presence of a diluent. Elucidation of processes and intermediate products Process (A) Using, for example, 2-amino-5-chloro-3, N-dimethylbenzamide and 5- (3,5-bistrifluormethylpyrazol-1-ylmethyl) -2-acid chloride - (3-chloropyridin-2-yl) -2H-pyrazol-3-carboxylic acid as starting materials, so the course of process (A) according to the invention may be shown by the following scheme of formula.

<formula> formula see original document page 17 </formula> 17

The aminobenzamides required as starting materials in carrying out process (A) according to the invention are generally defined by formula (II). In this formula (II) A, R1, R21 R31 R41 R5 and η preferably represent, particularly preferably, most particularly preferably or especially preferably those meanings, which have already been mentioned in the context with the description of the above. substances of formula (I) according to the invention as being preferred, particularly preferred and the like for such radicals.

Process (A) according to the invention is performed in the presence of an acid binding agent. For this purpose, the usual inorganic or organic bases suitable for such copulation reactions are suitable. Preferably alkali earth or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, may be used. sodium ethylate, potassium tert-butylate, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, diisopropylethylamine, β, β-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCOon) or diazabicyclone (DB) diazabicycloundecene (DBU). Likewise, polymer protected acid binding agents may be used, such as, for example, polymer-bound diisopropylamide and polymer-bound dimethylaminopyridine.

Process (A) according to the invention may optionally be carried out in the presence of an inert organic diluent usual for such reactions. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptan, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichlorethane or trichlorethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides such as β, β-dimethylformamide, β, β-dimethylacetamide, N-methylformalide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; their mixtures with water or pure water. Toluene, tetrahydrofuran and β, β-dimethylformamide are particularly preferably usable.

Reaction temperatures in carrying out process (A) according to the invention may vary over a wider range. In general, it works at temperatures of OcC to 150 ° C, preferably at temperatures of 20 ° C to 100 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under high or reduced pressure - generally between 0.1 bar and 10 bar,

Aminobenzamides of formula (II) are known (compare, for example, MJ Kornet, J. Heterocycl. Chem. 1992, 29, 103-105; GP Lahm et al., Bioorg. Med. Chem. Letters 2005, 15, 4898-4906 WO2003 / 016284, WO 2006/062978).

Pyrazolecarboxylic acid chloride of formula (III) is new. They may be prepared, for example, (D) by reacting pyrazolecarboxylic acid derivatives of formula (IV).

<formula> formula see original document page 19 </formula>

wherein A, Q and R6 have the meanings mentioned above with a chlorinating agent (eg thionyl chloride and oxalyl chloride) in the presence of an inert diluent (eg toluene and dichloromethane) in the presence of a catalytic amount of Ν, Ν-dimethylformamide.

Pyrazolecarboxylic acid derivatives of formula (IV) are new. 19

They can be prepared, for example,

(E) reacting pyrazolecarboxylic acid esters of formula (VI)

<formula> formula see original document page 20 </formula>

wherein A, Q and R6 have the meanings mentioned above and R represents C1 -C6 alkyl,

with an alkali metal hydroxide (eg sodium hydroxide or potassium hydroxide) in the presence of an inert diluent (eg dioxane / water or ethanol / water).

Pyrazolecarboxylic acid esters of formula (VI) are new. They may be prepared, for example, (F) by reacting pyrazolecarboxylic acid ester derivatives of formula (VII).

<formula> formula see original document page 20 </formula>

wherein A, Q and R6 have the meanings mentioned above and Z represents chloro, bromo, iodo, methylsulfonyl or toluenesulfonyl, with a heteroaromatic compound of formula (VIII) or with a boronic acid or a boronic acid ester of the formula ( IX) wherein R 'represents H, CH3, C2H5 or R1-R1 represents C (CH3) 2C (CH3) 2 and Q has the meanings mentioned above in the presence of a transition metal (e.g. tetramed ( triphenylphosphin) palladium (0)) and a base (eg potassium carbonate or sodium carbonate) in the presence of a solvent (eg tetrahydrofuran, acetonitrile or dioxane).

<formula> formula see original document page 20 </formula>

Heteroaromatic compounds and heterocycles of formula (VIII) are known, in part, even commercially available or can be obtained by known methods (compare, e.g., V. Days and others, Organometallics 1996, 15, 5374-5379 D. Threadgill et al., J. Fluorine Chem. 1993, 65, 21-23; M. Abdul-Ghani et al., J. Fluorine Chem. .1990, 48, 149-152; T. Kitazaki, Chem Pharm Bull 1996, 44, 314-327; DE 1995-19504627; WO 2004080984, WO 2005095351).

Heterocyclic boronic acids or boronates of formula (IX) are known, in part, even commercially available or can be obtained by known methods (compare, for example, W. Li1 DP Nelson, MS Jensen, RS Hoermer, D. Cai, RD Larsen, PJ Reider, J. Org. Chem. 2002, 67, 5394-5397).

Pyrazolecarboxylic acid ester derivatives of formula (VII) may be prepared, for example, (G) by reacting alcohols of formula (X)

<formula> formula see original document page 21 </formula>

wherein R, R6 and A have the meanings mentioned above, with a sulfonyl chloride (eg methylsulfonic acid chloride or toluenesulfonic acid chloride) or with a halogenating agent (eg thionyl chloride) optionally in the presence of a solvent (e.g. dichloromethane) and optionally in the presence of a base (e.g. triethylamine or pyridine).

Reaction temperatures in the process (G) according to the invention may vary over a broader range. In general, it works at temperatures of 0 ° C to 150 ° C, preferably at temperatures of 0 ° C to 60 ° C.

Alcohols of formula (X) may be prepared, for example, (H) by reacting pyrazoldicarboxylic acid esters of formula (XI)

<formula> formula see original document page 21 </formula> 21

wherein R and R 6 have the meanings mentioned above with a reducing agent (e.g. lithium aluminum hydride or diisobutyl aluminum hydride) in the presence of a solvent (e.g. tetrahydrofuran or diethyl ether).

Reaction temperatures in the process (H) according to the invention may vary over a wider range. In general, it works at temperatures from -100 ° C to 20 ° C, preferably at temperatures from -78 ° C to 0 ° C.

Pyrazoldicarboxylic acid esters of formula (XI) may be prepared, for example, by

(I) reacting hydrazines or their corresponding salts of formula (XII)

<formula> formula see original document page 22 </formula>

wherein R has the meaning mentioned above and R "represents methyl or ethyl or R" -R "represents (CH 2) 4 or (CH 2) 2 O (CH 2) 2, in the presence of a solvent (e.g. methanol or ethanol ).

Hydrazines or their corresponding salts of formula (XII) are known in part commercially available or may be prepared by general synthetic methods (compare, for example, Advanced Organic Chemistry, Fourth Edition, Jerry March, John Wiley & Sons, Inc. New York, 1992, page 1288).

Tricetones of formula (XIII) are known and can be prepared by general synthesis methods (compare for example, Cvetovich, Raymond J.; Pipik, Brenda; Hartner, Frederick W.; Grabowski, Edward JJ; Tetrahedron Lett 2003, 44). , 5867 - 5870).

Reaction temperatures in carrying out process (I) according to the invention may vary over a wider range. In general, it operates at temperatures of from 0 ° C to 80 ° C, preferably at temperatures of 40 ° C to 60 ° C. Process (B)

Using, for example, 2-amino-5-chloro-3 H, N -dimethylbenzamide and 5- (3,5-bis-trifluoromethyl-pyrazol-1-ylmethyl) -2- (3-chloro-pyridin-2-yl). 2-yl) -2H-pyrazol-3-carboxylic as starting materials, so the course of process (B) according to the invention may be shown by the following scheme of formula.

<formula> formula see original document page 23 </formula>

The anthranilamides of formula (II) required as starting materials in carrying out process (B) according to the invention have already been described in the context of process (A) according to the invention.

Heterocyclic carboxylic acids required, furthermore, as starting materials in carrying out process (B) according to the invention, are generally defined by formula (IV). In this formula (IV), R 6, A and Q preferably, particularly preferably, most particularly preferably or especially preferably represent those meanings, which have already been mentioned in the context of the description of the substances of formula (I) according to particularly preferred, and others for such radicals.

Process (B) according to the invention is performed in the presence of a condensing agent. For this purpose all usual agents for such copulation reactions are suitable. For example, mention should be made of acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride, anhydride builders such as ethyl ester.

chloroform acid, chloroform acid methyl ester, chloroform acid isopropyl ester, chloroform acid isobutyl ester or methanesulfonyl chloride; carbodiimides such as Ν, Ν'-dicyclohexylcarbodiimide (DCC) or other usual condensing agents such as phosphorus pentoxide, polyphosphoric acid, 1,1'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline ( EEDQ), triphenylphosphine / carbon tetrachloride, bromo-tripyrrolidinophosphonium hexafluorophosphate, bis (2-oxo-3-oxazolidinyl) phosphine chloride or benzotriazol-1-yloxytris (dimethylamino) -phosphonium hexafluorophosphate. Polymer supported reagents, such as, for example, polymer-linked cyclohexylcarbodiimide, may also be used.

Process (B) according to the invention is optionally carried out in the presence of a catalyst. For example, 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide are mentioned.

Process (B) according to the invention may optionally be carried out in the presence of an inert organic diluent usual for such reactions. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides such as N, N-dimethylformamide, N, β-dimethylacetamide, N-methylformalide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; their mixtures with water or pure water. Dichloromethane and α-β-dimethylformamide are particularly preferred.

Reaction temperatures in carrying out process (B) according to the invention may vary over a wider range. In general, it operates at temperatures of 0 ° C to 150 ° C, preferably at temperatures of 0 ° C to 80 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under high or reduced pressure - generally between 0.1 bar and 10 bar -. Process (C)

Using 2- [3 - {[3,5-bis (trifluoromethyl) -1H-pyrazol-1-yl] methyl} -1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] -6-chloro-8-methyl-4H-3,1-benzoxazin-4-one and methylamine, so the course of process (C) according to the invention can be shown by the following scheme of formula.

<formula> formula see original document page 25 </formula>

The benzoxazines required as starting materials in carrying out process (C) according to the invention are generally defined by formula (V). In this formula (V), R 4, R 5, R 6, A, Q and η preferably preferably, particularly particularly preferably or especially preferably those meanings, which have already been mentioned in the context with the description of the substances of the invention. formula (I) according to the invention as being preferred, particularly preferred and others for such radicals.

Benzoxazinones of formula (V) are new. They are obtained, for example,

(J) reacting pyrazolecarboxylic acid derivatives of formula (IV)

<formula> formula see original document page 25 </formula> where R6, A and Q have the meanings mentioned above with anthranilic acids of formula (XIV)

<formula> formula see original document page 26 </formula>

wherein R4, R5 and η have the meanings mentioned above, in the presence of a base (eg triethylamine or pyridine) and in the presence of a sulfonic acid chloride (eg methanesulfonic acid chloride) as well as possibly in the presence of a diluent (e.g. acetonitrile).

The pyrazolecarboxylic acid derivatives required as starting materials in carrying out process (J) according to the invention have already been described above in the context of process (A) according to the invention.

Anthranilic acids, furthermore necessary as starting materials in the execution of process (J), are generally defined by formula (XIV). In this formula (XIV) R 4, R 5 and η preferably preferably, particularly preferably, most particularly preferably or especially preferably those meanings, which have already been mentioned in the context with the description of the substances of formula (I) according to particularly preferred, and others for such radicals.

Anthranilic acids of formula (XIV) are known and may be prepared by general synthetic methods (compare, for example, Baker et al., J. Org. Chem. 1952, 149-153; G. Reissenweber et al., Angew. Chem. 1981, 93, 914-915, PJ Montoya-Pelaez, J. Org. Chem. 2006, 71, 5921-5929; FE Sheibley, J. Org. Chem. 1983, 3, 414-423, WO .2006023783).

The compounds of formula (I) may optionally be present in various polymorphic forms or as a mixture of various polymorphic forms. Both pure polymorphs and polymorph mixtures are both subject to the invention and may be used in accordance with the invention. With good plant tolerance, favorable toxicity for warm-blooded animals and good environmental tolerance, the active substances according to the invention are suitable for protecting plants and plant organs, to increase crop yield, improve the quality of harvested material and to combat animal parasites, especially insects, arachnids, helminths, nematodes and molluscs, which occur in farming, horticulture, livestock, forests, garden and leisure facilities, protection of stored food and material, as well as in the hygiene sector. They may preferably be used as preparations to protect plants. They are effective against normally sensitive and resistant species, as well as all or some stages of development. The parasites mentioned above include:

From the order of the Anoplura (Phth ri rapte ra), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

From the Arachnida class, for example, Acarus siro, Aeeria sheldeni, Aeulops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranyehus spp., Epitrimerus pyri, Eutetranyehus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodeetus mactans, Metatetranyehus spp., Oligonyehus spp., Ornithodoros spp. Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sareoptes spp., Seorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranyehus spp.

From the Bivalva class, for example, Dreissena spp ..

From the order of the Chilopoda, for example, Geophilus spp., Seutige spp.

Of the order Coleoptera, for example, Aeanthoseelides obtectus, Adoretus spp., Agelastiea alni, Agriotes spp., Amphimallon solstitialis, Anobium punetatum, Anoplophora spp., Anthonomus spp., Apogonia spp., Aogoma spp. Attagenus spp., Bruehidius obteetus, Bruehus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopoliters spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabroti spp. Faustinus eubae, Gibbium psylloides, Heteronyehus arator, Hylamorpha elegans, Hylotrupes bajulus, Fake Hyperothus, Hypothenemus spp. , Migdolus spp., Monoehamus spp., Naupae- tus xanthographus, Niptus hololeueus, Oryetes rhinoeeros, Oryzaephilus suinamensis, Otiorrhynehus suleatus, Oxycetonia jueunda, Phaedon cochleariae, Phyllophaia japi, Phyllophaga japi. Premnotrypes spp., Psylliodes e-hrysoeephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominiea, Sitophilus spp., Sphenophorus spp., Symphyletes spp., Tenebrrio molitor, Tribolium spp. Tyehius spp., Xylotreehus spp., Zabrus spp.

From the order of the Collembola, for example, Onyehiurus armatus.

From the order of the Dermaptera, for example, Forfieula aurieularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythroeephala, Ceratitis eapitata, Chrysonia spp., Coehliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra olea, Daeus olea. , Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Lueiomyza spp., Musea spp., Nezara spp. Oseinella frit, Pegomyia hyoseyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tanya spp., Tipula paludosa, Wohlfahrtia spp.

From the Gastropoda class, for example, Arion spp., Biomphalia spp., Bulinus spp., Deroeeras spp., Galba spp., Lymnaea spp., Oneomelia spp., Sueeinea spp.

Of the helminth class, for example Ancylostoma duodenale, Ancylostoma eeylanieum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubicoides, Ascaris spp., Brugia malayi, Bunugomum spp., Chabertia spp., Clonorchis spp. Dicrocoelium spp, Dictyocau- 28

Ius filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinoeoceus multiloeularis, Enterobius vermieularis, Faeiola spp., Haemonehus spp., Heterakis spana. . Onehoeerea volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stereoralis, Stronyloides spp., Taenia saginata, Taenia solium Trichostronagulus spp., Triehuris triehuria, Wuchereria banerofti.

In addition, protozoa such as Eimeria can be fought.

From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Caloeoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Diehelops fureatus, Dieonoeoris hewetti, Dono ., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horbil nobilellus, Leptoeorisa spp., Leptoglossus phyllopus, Lygus spp., Maeropes exeavatus, Miridae, Nezara spp., Oebalus spp., Penomata quadratus, Piesma quadrata Piezodorus spp., Psallus seriatus, Pseudaeysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraea spp., Triatoma spp.

From the order of Homoptera, for example, Aeyrthosipon spp., Aeneolamia spp., Agonoseena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasea spp., Anuraphis eardui, Aonidiella spp. spp., Arboridia apiealis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Braehycaudus heliehrysii, Brachycolus spp., Brevieoryne brassieae ., Chatosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandieola, Chrysomphalus fieus, Cieadulina mbila, Coccomytilus halli, Cocusus ribis, Dalbulus spp., Dialeuror spp. Spp. Doralis spp., Drosieha spp., Dysaphis spp., Dysmieoeeus spp., Empoasea spp., Eriosoma spp., Erythroneura spp. Idioscopus spp., Laodelphax striatellus, Leeanium spp., Lepidosaphes spp., Lipaphis erysimi, Maerosiphum spp., Mahanarva fimbriata, Melanaphis saeehari, MeteaIfieIIa spp. photettix spp., Nilaparvata lugens, Oneometopia spp., Orthezia praelonga, Parabemisia myrieae, Paratrioza spp., Parlatoria spp., Pemphigus spp. Pinnaspis aspidistrae, Planoeoeeus spp., Proto-pulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudoeoceus spp., Psyl-la spp., Pteromalus spp., Quadraspidiotus spp. Seaphoides titanus, Sehizaphis graminum, Selenaspidus artieulatus, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictoeephala festina, Tenalaphara malayensis, Tinoleal earyaefoliae, Tomaspis spp., Toxoptera sp. vaporario rum, Trioza spp., Typhloeyba spp., Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoploeameam spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare, Oniseus asellus, Porcellio seaber.

From the order of the Isoptera, for example, Retieulitermes spp., Odonotermes spp ..

From the order of the Lepidoptera, for example, Aeronieta major, Aedia leueomelas, Agrotis spp., Alabama argillaeea, Antiearsia spp. ., Choristomura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproetis ehrysorrhoea, Euxoa spp., Feltia spp., Helioveris spp. , Laphygma spp., Lithocolletis blaneardella, Lithophane antennata, Loxagrotis albieosta, Lymantria spp., Malaeosoma neustria, Maestra brassieae, Moeis repanda, Mythimna septata, Oria spp., Oulema oryza, Panolis flammea spp. ., Plutella xylostella, Prodenia spp., Pseudoplasia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermia gemmatais, Tinea IIione IIa, Tineola bisse Ilie lia, Tortrix virida na, Trochoplusia spp.

From the order of Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca greek.

From the order of the Siphonaptera, for example Ceratophyllus spp., Xenopsylla cheopis.

From the order of the Symphyla, for example, Seutigerella immaeulata.

From the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hereinothrips femoralis, Kakothrips spp., Rhipiphorothrips eruentatus, Scirtothrips spp., Taeniot-hrips eardamp.

From the order of the Thysanura, for example, Lepisma saeeharina.

Phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Dithylenehus dipsaei, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogy spp. spp., Radopholus similis, Rotylenehus spp., Triehodorus spp., Tylenehorhynehus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

The compounds according to the invention may optionally be used in certain concentrations or amounts of application, also as herbicides, protectors, growth regulators or agents for improving plant properties or as microbicides, for example. as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Myco-plasma-like-organism) and RLO (Rickettsia-like-organism). Eventually they may also be used as intermediate products or preproducts for the synthesis of other active substances. Active substances can be converted to common formulations such as solutions, emulsions, spray powders, water and oil based suspensions, powders, spray powders, pastes, soluble powders, soluble granules, dispersion, emulsion-suspension concentrates, active substance-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers, and very fine encapsulations in polymeric substances.

Such formulations are prepared in a known manner, for example by mixing the active substances with diluents, i.e. liquid solvents and / or solid excipients, optionally with the use of surfactants, i.e. emulsifiers and / or dispersing agents and / or foaming agents. The preparation of the formulations is carried out either in suitable facilities or before or during application.

As adjuvants those suitable substances may be used to lend particular properties to the composition itself and / or to preparations derived therefrom (eg spray broths, seed disinfectants) such as certain technical properties. and / or also particular biological properties. Typical adjuvants are: diluents, solvents and excipients.

Suitable diluents are, for example, water, polar and nonpolar organic chemical liquids, for example from the aromatic and non-aromatic hydrocarbon classes (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which they may also be substituted, etherified and / or esterified) from ketones (such as acetone, cyclohexanone), esters (also greases and oils) and (poly) ethers from amines, amides, substituted and simple lactams (such as N-alkylpyrrolidones) and lactones from sulfones and sulfoxides (such as dimethyl sulfoxide).

When using water as a diluent, for example, organic solvents may also be used as auxiliary solvents. Liquid solvents essentially include: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example, petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfon - oxide as well as water.

Solid excipients are taken into account: for example, ammonium salts and natural stone powders such as kaolin, clays, talc, chalk, quartz, attapulgite, montmorillonite or infusory earth and synthetic stone powders such as silicic acid highly dispersed, aluminum oxide and silicates as solid granular excipients are considered: for example, broken and fractionated natural stones such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic flour granules inorganic and organic materials as well as granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifiers and / or foaming agents are considered: for example, nonionogenic and anionic emulsifiers such as polyoxyethylene fatty acid ester, polyethylene fatty alcohol ether, for example alkylaryl polyglycol ether, sulfonates of alkyl, alkyl sulfates, aryl sulfonates as well as alumina hydrolysates; Dispersing agents include: non-tonic and / or ionic substances, for example, from the classes of alcohol-POE ethers and / or POP ethers, acid and / or POP-POE esters, alkyl ethers. and / or POP-POE, lipid and / or POP-POE addition products, derived from POE and / or POP-polyol, POE and / or POP-sorbitan or sugar addition products, alkyl sulfates or aryl, sulfonates and phosphates or the corresponding PO-ether addition products. In addition, suitable oligomers and polymers, for example starting from vinyl, acrylic acid, EO and / or PO monomers alone or in combination, for example, with (poly) alcohols or (poly) amines. In addition, lignin and its sulfonic acid derivatives, simple and modified celluloses

aromatic and / or aliphatic sulfonic compounds, as well as their formaldehyde addition products.

Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or latex form such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids such as cephalins and Iecithins and synthetic phospholipids.

Dyes such as inorganic pigments may be used, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and phthalocyanine metal dyes and traces of nutritional substances such as iron salts , manganese, boron, copper, cobalt, molybdenum and zinc.

Other additives may be perfumes, possibly modified vegetable or mineral oils, waxes and nutrients (also micronutrients) such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

In addition, stabilizers such as cold stabilizers, preservatives, oxidation protection agents, sunscreen agents or other chemical and / or physical enhancing agents may be contained.

In general, the formulations contain from 0.01 to 98% by weight of active substance, preferably from 0.5 to 90%.

The active substance according to the invention may be present in its usual commercial formulations as well as in the application forms prepared from such formulations in admixture with other active substances such as insecticides, decoys, sterilizers, bactericides, acaricides, nematicides, fungicides, growth regulating substances, herbicides, protectors, fertilizers or semi-chemicals.

Particularly favorable mixing participants are, for example, the following: Fungicides:

Inhibitors of benalaxyl nucleic acid synthesis, benalaxyl-M, bupirimat, chiralaxil, clozilacon, dimethirimol, etirimol, furalaxil, himexazole, metalaxyl, metallaxyl, oxurixil, oxolinic acid Inhibitors of mitosis and benomyl diethyl carbendazole, carbenazole, fuberidazole, pencicuron, thiabendazole, thiophanate-methyl, zoxamide Respiratory chain complex inhibitors I diflumetorim Respiratory chain complex inhibitors Il boscalid, carboxin, fenfuram, flutolanil, furametpir, mepronil, oxicarboxin, pentiopirad, tifluzamide complex azoxystrobin, ciazofamid, dimoxystrobin, enestrobin, famoxadon, fenamidon, fIuoxastrobin, kresoxim-methyl, metominostrobin, orisastrobin, picoxistrobin, trifloxistrobin Dinocap uncouplers, fluazinam phosphate inhibitors of fentin, hydrofluorine inhibitors of fentin, hydrochloride inhibitors of amino acid and protein biosynthesis prim, blasticidin-S, cyprodinil, kasugamycin, ca-sugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil Signal transduction inhibitors fenpiclonil, fludioxonil, quinoxifen Lipid and membrane synthesis inhibitors clozolinat, iprodion, procimidon, vinclozolin, vinclozolin, vinclozolin, ampropylphos, edifenphos, iprobenfos (IBP) 1 isoprothiolan, pyrazophos, tolclofosmethyl, biphenyl, iodocarb, propamocarb, propamocarb hydrochloride inhibitors biosynthesis of ergosterol fenexamide, azaconazole, bitertanol, bromuconazole diprobenazole, diprobenazole -M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, miclobutrazol, penconazole, propiconazole, protioconazole, simecononazole, trebimethiazole, tebuconazole , triticonazole, uniconazole, voriconazole, imazalil, imazalyl sulfate, oxpoconazole, fe narimol, flurprimidol, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorf, dodemorf, dodemorf acetate, fenpropimorf, tridemorf, fenpropidin, spiroxamine, naphthifin, pyributicarb, terbinafin. Cell Wall Synthesis Inhibitors

bentiavalicarb, bialaphos, dimetomorph, flumorf, iprovalicarb, polyoxins, polyoximine, validamycin A Melanin biosynthesis inhibitors

capropamide, diclocimet, phenoxanil, phthalid, pyroylon, tricyclazole Acibenzolar-S-methyl resistance induction, probenazole, thiadinyl Multisite

captafol, captan, ciorotalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxin-copper and Bordeaux mixture, diclofluanid, dithianon, dodin, free base dodin, ferbam, folpet, fluorofolpet, guazatine, guazatine acetate, iminoctadin, iminoctadinalbesilate, iminoctadin triacetate, mancobre, mancozeb, maneb, meth, meth, zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, tiramide, , zineb, ziram. Unknown engine

amibromdol, bentiazole, betoxazin, capsimycin, carvon, quinomethionate, chloro-picrin, cufraneb, ciflufenamid, cimoxanil, dazomet, debacarb, dichlomenzine, dichlorophen, dichloran, difenzoquat, difenzo-sulfonate, ethamphenamide, diphenoxamide, , fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, metasulfocarb, metrophenon, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrotalisopropyl, octylinon, oxamenthol, pentachenthen, phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrrolinitrine, quintozen, keyboardoftalam, tecnazen, triazoxide, triclamide, zarylamide and, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- ( 4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolcarboxamide, 2-chloro-N (2,3-dihydro-1,1 1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin -3-yl] pyridine, cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, 2,4-dihydro-5-methoxy-2-one methyl-4 - [[[[[1- [3- (trifluoromethyl> phenyl] ethyliden] amino] oxy] methyl] phenyl] -3H-1,2,3-triazol-3-one (185336) -79-2), methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazol-5-carboxylate, .3,4,5-trichloro Methyl -2,6-pyridinedicarbonitrile, methyl 2 - [[[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] alpha- (methoxymethylen) benzacetate, 4-chloro-alpha-propynyloxy-N- [ 2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] - 3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorphenyl) [ 1,2,4] triazolo [1,5-a] pyrimidimine, 5-chloro-6- (2,4,6-trifluorphenyl) -N - [(1 R) -1,2,2-trimethylpropyl] [1 2,4] triazolo [1,5-a] pyrimidin-7-amine, 5-chloro-N - [(1 R) .1,2-dimethylpropyl] -6- (2,4,6-trifluorphenyl) [ 1,2,4] triazolo [1,5-a] pyrimidin-7-amine, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4- dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronicotinamide, 2-butoxy-6-iodo-3-propylbenzopyran-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorphenyl] methyl} -2-benzacetamide, N- (3-ethyl-3,5,5-trimethyl-cyclohexyl) -3-formylamino-2 -hydroxy-benzamide, 2 - [[[[[1- [3- (1-fluor-2-phenylethyl) oxy] phenyl] ethylene] amino] oxy] methyl] -alpha- (methoximino) -N-methyl-alphaE -benzacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3 ', 4'-dichloro-5'-fluorobiphenyl- 2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-carboxamide, N- (6-methoxy-3-pyridinyl) cyclopropan carboxamide, 1 - [(4-methoxyphenoxy) methyl] - .2,2-dimethylpropyl-1 H -imidazol-1-carboxylic acid 0- [1 - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazol-1-carbothioic acid, 2 - (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluorpyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide. Bactericides:

bronopol, dichlorophene, nitrapirin, nickel dimethyl dithiocarbamate, kasugamycin, octylinon, furanecarboxylic acid, oxytetracycline, probenazole, streptomycin, keyophthalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: Acetylcholinesterase (AChE) carbamates inhibitors,

for example alanicarb, aldicarb, aldoxycarb, alixicarb, aminocarb, bendicarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, closulfan, cloetocarb, dimethylan, ethiofencarbate, phenobarbate, phenobarbate , metam-sodium, methocarb, methomyl, metolcarb, oxamyl, pyrimicarb, promecarb, propoxur, thiodicarb, thiophanx, trimetacarb, xylylcarb, triazamate, Organophosphates,

for example acetate, azametiphos, azinphos (methyl) ethyl, bromophosethyl, bromophenvinphos (methyl), butathiophos, cadusaphos, carbofenotion, chlorideoxyphos, chlorphenvinphos, chlormephos, chlorpyrites (methyl / ethyl), coumaphos, cyanofos , cyanophos, chlorphenvinphos, demeton-S-methyl, demeton-S-methylsulfone, dialiphos, diazinon, diclofention, dichlorvos / DDVP, dichrotophos, dimethoate, dimethylvinphos, dioxabenzophos, disulfoton, EPN, etion, etphophosphenates, etphophosphamides fenitrotion, fensulfotion, fention, flupirazophos, phonophos, formotion, fosmetil, fostiazate, heptenophos, iodophenphos, iprobenfos, isazofos, isofenphos, isopropyl-O-salicylate, isoxation, malation, mecarbam, methacridophosphoridate , monocrotophos, naled, ometoate, oxidemeton-methyl, paration (-methyl / ethyl), phentoate, phorate, fosalon, fosmet, phosphamidon, phosphocarb, foxim, pyrimiphos (-methyl / ethyl), profenofos, propafos, propetamfos, protiofos , protoate, piraclofos, pyridafention, pyridation, q uinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, triclorfon, vamidotion. Sodium Channel Modulators / Voltage Dependent Sodium Channel Blockers Pyrethroids,

for example acrinatrin, aletrin (d-cis-trans, d-trans), beta-ciflutrin, bifentrin, bioaletrin, bioaletrin-S-cyclopentyl isomer, bioetanometrin, biopermetrin, bioresmetrin, clovaportrin, cis-cypermetrin, cis-resmetrin cis-permetrin, clocitrin, cycloprotrin, citlutrin, cyhalotrin, cypermetrin (alpha, beta, theta, zeta), cyphentrin, deltametrin, empentrin (1R isomer), esfenvalerate, etofenprox, fenflutrin, fenpropatrin, fenpropatrin, fenpropatrin , flubrocitrinate, flucitrinate, flufenprox, flumetrin, fluvalinate, fubfenprox, gamma-cyhalotrin, imiprotrin, kadetrin, lambda-cihalotrin, metoflutrin, permethrin (eis-, trans-), fenotrin (1Retrin, prof, trans-isomer) protrifenbuto, piresmetrin, resmetrin, RU 15525, silafluofen, tau-fluvalinate, teflutrin, teraletrin, tetrametrin (1R isomer), trolometrin, transflutrin, ZXI 8901, pyrethrins (pyretrum) DDT

Oxadiazines, e.g. indoxacarb, Semicarbazones, e.g. metaflumizone (BAS 3201)

Chloronicotinyl acetylcholine receptor agonists / antagonists,

for example acetamiprid, clotianidin, dinotefuran, imidacloprid, nitenpiram, nitiazine, thiacloprid, thiametoxam. Nicotine bensultap cartap

Acetylcholine receptor modulators spinosine, for example spinosad.

GABA organochlorine-regulated chloride channel antagonists,

e.g. camfeclor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor Fiprols e.g., acetoprol, etiprol, fipronil, pirafluprol, pyriprole, vaniliprol Mectin chloride channel activators,

for example abamectin, emamectin, emamectin benzoates, ivermectin, lepimectin, milbemycin. Juvenile hormone mimetics, for example, diofenolan, epofenonane, phenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene. Eedison diacyl hydrazine agonists / disruptors,

e.g. chromafenozide, halofenozide, methoxyphenozide, tebufenozide Chitin biosynthesis inhibitors

benzoylureas,

for example bistrifluron, clofluazuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron Buprofezine Ciromazine. buprofezine cyromazine

Oxidative Phosphorylation Inhibitors, ATP Diafentiuron Disruptors

Organotin compounds, for example azocyclotine, cyhexatin, fenbutatin oxide

Decouplers of oxidative phosphorylation by interrupting the gradient of proton H pyrroles,

for example chlorphenapyr Dinitrophenols,

e.g. binapacril, dinobuton, dinocap, DNOC Side I electron transport inhibitors METI1S,

e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpirad, tolfenpirad Hidramethylnon Dicofol

Il rotenone electron transport inhibitors

Ill-side electron transport inhibitors acequinocil, fluacripirim

Insect microbial membrane disrupters of Bacillus thuringiensis strains Inhibitors of tetronic acid lipid synthesis,

e.g. spirodiclofen, spiromesifen tetramic acids,

e.g. spirotetramate, cis-3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1-azaspiro [4,5] dec-3-en-2-one carboxamides, e.g. flonicamid Octopaminergic agonists e.g. amitraz

Magnesium-stimulated ATPase inhibitors, for example propargitis Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium Ryanodine receptor agonists, benzoic acid dicarboxamides, for example, flubendiamide anthranilamides,

for example, rinaxapyr (3-bromo-N- {4-chloro-2-methyl-6 - [(methylamino) carbonyl] phenyl} -1- (3-chloropyridin-2-yl) -1H-pyrazol-5-carboxamide ) Biological, hormones or pheromones

azadiractin, Bacillus spec., Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticillium spec. Active substances with unknown or unspecific mechanisms of action Gasification agents, eg aluminum phosphides, methyl bromides, sulfuryl fluorides Devouration inhibitors, eg cryolite, flonicamid, pimetrozine Mite growth inhibitors, for example , clofentezine, ethoxazole, hexithiazox amidoflumet, benclothiaz, benzoxime, biphenazate, bromopropylate, buprofenin, quinomethionate, clordimeform, chlorobenzylate, chloropicrin, clotiazoben, cycloprene, cifluometofen, dicyclinulfonyl, fenbenzamin, flyxulfin, japonilure, methoxyadiazine, petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon, tetrasul, triaratene, verbutin.

It is also possible to mix with other known active substances such as herbicides, fertilizers, growth regulators, protectors, semi-chemicals or also with agents to improve the characteristics of plants.

When used as insecticides, the active substances according to the invention may furthermore be present in their commercially available formulations as well as in the application forms prepared from such formulations in admixture with synergists. Synergists are compounds whereby the effect of active substances increases without the added synergist himself having to be actively effective. Especially ammonium or phosphonium salts and / or penetration enhancers may be added to increase the effect.

When used as insecticides, the active substances according to the invention may furthermore be present in their commercially available formulations as well as in the application forms prepared from such formulations in admixture with inhibitory substances. , which reduce degradation of the active substance after application to plant arbor- ers, the surface of plant parts or plant tissues.

The active substance content of the application forms prepared from commercially available formulations may vary widely. The concentration of active substance of the application forms may be from 0.00000001 to 95% by weight of active substance, preferably from 0.00001 to 1% by weight.

Application takes place in the usual manner adapted to one of the application forms.

According to the invention, all plants and parts of plants can be treated. In this case, plants are all plants and plant populations, such as wild plants or desirable and undesirable cultivated plants (including cultivated plants of natural origin). Cultivated plants may be plants, obtained by conventional cultivation and optimization methods or by biotechnological and genetic methods or combinations of these methods, including transgenic plants and even plant species that are protected or not protected by species protection laws. By plant parts is meant all the aerial and underground parts and plant organs such as bud, leaf, flower and root, being listed for example, leaves, thorns, stems, trunks, flowers, fruit body, fruits and seeds, as well as roots, tubers and rhizomes. Plant parts also include harvesting material as well as vegetative and generative growth material, for example cuttings, tubers, rhizomes, tanks and seeds.

Treatment of plants and plant parts with the active substance combinations according to the invention is effected either directly or by action on their environment, living space or deposit according to the usual treatment methods, for example by immersion. spraying, evaporating, nebulizing, scattering, coating, injecting and in the case of growth material, especially in the case of seed, furthermore by coating one or more layers.

As already mentioned above, according to the invention, it is possible to treat all plants and parts thereof. In a preferred embodiment, plant types and wild plant species or those obtained by conventional biological cultivation methods, such as crossing or fusion of protoplasts, as well as parts thereof, are treated. In another preferred embodiment, transgenic plants and plant species, which have been obtained by genetic engineering methods, possibly in combination with conventional methods (Genetically Modified Organisms) and parts thereof, are treated. The terms "parts" or "parts of plants" or "parts of plants" have been explained above.

Particularly preferably, plants of the plant species in each case commercially available or in use are treated according to the invention. Plant species means plants with new traits, which have been cultivated either by conventional cultivation, by mutagenesis or by recombinant DNA techniques. These can be species, biotypes and genotypes.

Depending on plant types or plant species, their location and growing conditions (soils, climate, growing season, nutrition) may also occur superadditive ("synergistic") effects through treatment according to the invention. Thus, for example, reduced application amounts and / or increases in action spectrum and / or enhanced effect of the applicable substances and compositions according to the invention, better plant growth, high tolerance are possible. high or low temperature resistance, high drought or salt tolerance in water or soil, high flowering power, easier harvesting, accelerated ripening, higher harvesting yield, higher quality and / or higher nutritional value of harvested products , greater storage capacity and / or processing capacity of harvested products that exceed the effects to be expected.

Transgenic (genetically engineered) plants or plant species which should preferably be treated in accordance with the invention include all plants which, by virtue of genetic modification, have received genetic material, which confer valuable traits. particularly advantageous to such plants. Examples of such properties are better plant growth, high tolerance against high or low temperatures, high tolerance against drought or salt content in water or soil, high flowering power, easier harvesting, accelerated ripening, higher yields. harvesting, higher quality and / or higher nutritional value of harvested products, higher storage capacity and / or processing capacity of harvested products. Other particularly prominent examples of such properties are a high defense of plants against animal and microbial parasites, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, as well as high toxicity.

plant veranance against certain herbicidal active substances. Examples of transgenic plants include important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetable species, cotton, tobacco, rapeseed, as well as fruit plants (such as apple, pear, citrus and grapes), particularly maize, soy, potato, cotton, tobacco and rapeseed. Traits include the high defense of plants against insects, arachnids, nematodes and snails due to toxins formed in plants, especially those which are produced in plants by the genetic material of Bacillus Thuringiensis (eg. CrylA (a), CrylA (b), CrylA (c), CrylIA, CrylllA, CrylllB2, Cry9c, Cry2Ab, Cry3Bb and CrylF genes and combinations thereof (hereinafter "BT plants"). Particularly noteworthy are traits of plants against fungi, bacteria and viruses through acquired systemic resistance (SAR), systemin, phytoalexin, elicitors, as well as resistance genes and proteins and toxins expressed in a similar manner. correspondent. Other traits include the high tolerance of plants against certain herbicidal active substances, eg imidazolinones, sulfonylureas, glyphosate or phosphorothricin (eg gene 'PAT'). ). Genes that confer the desired properties in question can also occur in combinations with each other in transgenic plants. Examples of "Bt plants" include maize species, cotton species, soybean species and potato species, which are sold under the trade names Yl-ELD GARD® (eg maize, cotton, soy), KnockOut. ® (eg maize), StarLink® (eg maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants include maize species, cotton species and soybean species, which are sold under the trade names Roundup Ready® (glyphosate tolerance, eg maize, cotton, soybean) , Liberty Link® (tolerance against phosphinothricin, eg rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulphonylureas, eg corn). Herbicide-resistant plants (conventionally grown for herbicide tolerance) include species sold under the name Clearfield® (eg maize). Of course, this information is also valid for plant species to be developed in the future or to come to market in the future with these genetic properties or to be developed in the future (traits).

The listed plants may be particularly advantageously treated according to the invention, the compounds of general formula I or the mixtures of active substances according to the invention. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures especially listed in this text.

The active substances according to the invention act not only against plant parasites, hygiene and stored food, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites) such as breastplate ticks, ticks. leather, scabies, runner mites, flies (biters and lickers), parasitic fly larvae, lice, nits, feather nits and fleas. These parasites include:

Of the order Anopluride, for example, Haematopinus spp., Lingnathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the Amblycerina suborders as well as Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Lepikentron spp., Damalina spp., Tri-ehodectes spp. spp ..

From the order of the Diptera and the suborders Nematoeerina as well as Braehyeerina, for example, Aedes spp., Anopheles spp., Culex spp., Simuli- spp., Phybotomus spp., Lutzomyia spp., Culicoides spp. spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopot spp., Philipomyia spp., Braula spp., Musea spp., Stomoxys spp., Haematobia spp., Morellia spp. , Fannia spp., Glossina spp., Cal-46

Iiphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Hasterobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapteride, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..

Of the order Heteropteride, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..

From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..

From the subclass of Acari (Acarina) and from the orders of Meta- as well as Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Boophilus spp., Dermaeentor spp., Ha- emophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..

Of the order Actinedida (Prostigmata) and Aearidida (Astigmata), for example, Aearapis spp., Cheyletiella spp., Ornithoeheyletia spp., Myobia spp., Demorex spp., Trombieula spp., Listrophorus spp. ., Tyrophagus spp., Caloglyphus spp., Hypodeetes spp., Pteroleeus spp., Psoroptes spp., Chorioptes spp., Otodeetes spp., Notoedres spp., Knemidoeoptes spp., Cytodiop spp. ..

The active substances of formula (I) according to the invention are also suitable for combating arthropods which attack domestic agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes. , rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals, such as dogs, cats, cage birds, aquarium fish, as well as so-called guinea pigs, such as hamsters, guinea pigs of India, rats and mice. By combating these arthropods, deaths and yield reductions (in the case of meat, milk, wool, skins, eggs, honey and others) should be reduced so that the use of the active substances according to the invention makes it possible to more economical and simpler livestock. The application of the active substances according to the invention to the veterinary and livestock sector is known in the known manner by enteral administration in the form, for example, of tablets, capsules, beverages, drains, granulates, pastes, cakes, from the process ". suppositories by parenteral administration, such as, for example, by injections (intramuscular, subcutaneous, intravenous, intraperitoneal and others), implants, by nasal application, dermal application by dipping, spraying, pour-on and spot-on, washing, dusting as well as the aid of molded articles containing active substance such as a collar, earmarks, tails marks, joint straps, halters, marking devices and others.

For application in livestock, poultry, domestic animals and others, the active substances of formula (I) may be employed as formulations (eg, powders, emulsions, flow agents) containing the active substances in an amount of 1 up to 80% by weight, either directly or after dilution 100 to 10,000 times or they can be applied as a chemical bath.

Furthermore, it has been found that the compounds according to the invention show a high effect against insects, which destroy technical materials.

For example and preferably - without, however, limiting - the following insects are mentioned:

beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufoviliosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus rugus, Lyctus planus, Tricus lupus , Xyleborus spee., Tryptodendron spee., Apate monaehus, Bostryehus capueins, Heterobostrychus brunneus, Sinoxylon spee., Dinodeorus minutus.

Hymenoptera such as Sirex juveneus, Uroeerus gigas, Uroeerus gigas taignus, Uroeerus augur. Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterothermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Retieuliemes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotalmes formosanus.

5 Moths such as Lepisma saccharina.

Technical materials in the present context are non-living materials, such as preferably plastic materials, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paint products.

Ready-to-use compositions may optionally contain further insecticides and optionally one or more fungicides.

With respect to possible additional mixing participants, reference should be made to the insecticides and fungicides mentioned above.

At the same time, the compounds according to the invention can be used for protection against fouling of objects, especially ship bodies, sieves, nets, buildings, moorings and bells, which come into contact with each other. with seawater or brackish water.

In addition, the compounds according to the invention may be used alone or in combination with other active substances as antifouling agents.

Active substances are also suitable for combating animal parasites in domestic, hygienic and stored food protection, especially insects, arachnids and mites, which occur in enclosed environments such as homes, factory patios, offices, car cabs and others. They can be used individually or in combination with other active substances and adjuvants in household insecticide products to combat these parasites. They are effective against sensitive and resistant species as well as against all stages of development. These parasites include:

From the order of Scorpionidea, for example, Buthus occitans.

From the order of the Acarina, for example Argas persicus, Argas, Retexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides ptermatopusuminae.

From the order of the Araneae, for example, Aviculariidae, Araneidae. From the order of the Opions, for example, Pseudoscorpiones chelfer, Pseudoscorpiones eheiridium, Opiiiones phalangium.

From the order of the Isopoda, for example, Oniseus aselius, Porcellio seaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp ..

From the order of the Chilopoda, for example, Geophilus spp ..

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saeeharina, Lepismodes inquilinus.

Of the order of the Blattaria, for example, Blatta orientalis, Blattella germaniea, Blattella asahinai, Leucophaea maderae, Panehlora spp., Parcoblatta spp.

From the order of the Saltatoria, for example, Aeheta domestieus.

From the order of the Dermaptera, for example, Forfieula aurieularia.

From the order of the Isoptera, for example, Kalotermes spp., Reticuliotheres spp.

From the order of the Psoeopterai for example, Lepinatus spp., Liposeelis spp.

Of the order Coleoptera, for example, Anthrenus spp., Attageus spp., Dermestes spp., Lathetieus oryzae, Neerobia spp., Ptinus spp.

From the order of the Diptera, for example Aedes aegypti, Aedes albopietus, Aedes taeniorhynehus, Anopheles spp., Calliphora erythroeephala, Chrysozona pluvialis, Culex pipiens, Culex tarsalis, Drosophila spp. ., Sareophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa. From the order of the Lepidoptera, for example Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineo- la bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera, for example, Camponotus hercu- leanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Citi lectularius, Rhodnius prolixus, Triatoma infestans.

Application within domestic insecticides is performed alone or in combination with other suitable active substances such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active substances of other known classes of insecticides.

The application is carried out on aerosols, non-pressurized atomizing agents, for example, pump and spray sprays, automatic nebulizers, nebulizers, foams, gels, evaporators with cellulose or plastic evaporators, liquid evaporators, gel evaporators and membranes, propeller-driven evaporators, powerless or passive evaporation systems, moth papers, moth bags and moth gels such as pellets or powders in spreading bait or bait stations.

The following examples of preparation and use illustrate without limiting the invention. Preparation Examples Example 1

Acid 5- (3,5-Bis-trifluoromethyl-pyrazol-1-ylmethyl) -2- (3-chloro-pyridin-2-yl) -2H (4-chloro-2-methyl-6-methylcarbamoyl-phenyl) -amide -pyrazol-3-carboxylic acid (1-1 -1): .300 mg (509 pmol) of 2- [5- (3,5-bis-trifluoromethyl-pyrazof-1-ylmethyl) -2- (3-chloro) (iridin-2-yl) -2H-irazol-3-yl] -6-chloro-8-methyl-benzo [d] [1,3] oxazin-4-one are previously introduced into 3.3 ml of tetrahydrofuran and 764 μΙ (1.53 mmol) of a 2 M methylamine solution is added dropwise in tetrahydrofuran. Stir for 1 hour at 50 ° C, after cooling, remove the solvent in vacuo and purify the residue on silica gel (cyclohexane / ethyl acetate = 2: 1-4 1: 1). Yield: 200 mg (logP: 3.67).

In a manner analogous to the example (1-1-) shown above, as well as to the general description, the following compounds of formula (1-1) are obtained.

<formula> formula see original document page 52 </formula>

Table 1

<table> table see original document page 52 </column> </row> <table> <table> table see original document page 53 </column> </row> <table> <table> table see original document page 54 < / column> </row> <table> <table> table see original document page 55 </column> </row> <table> <table> table see original document page 56 </column> </row> <table> <table> table see original document page 57 </column> </row> <table> <table> table see original document page 58 </column> </row> <table> <table> table see original document page 59 < / column> </row> <table> 59

<table> table see original document page 60 </column> </row> <table> <table> table see original document page 61 </column> </row> <table> <table> table see original document page 62 < / column> </row> <table> <table> table see original document page 63 </column> </row> <table> <table> table see original document page 64 </column> </row> <table> <table> table see original document page 65 </column> </row> <table> <table> table see original document page 66 </column> </row> <table> <table> table see original document page 67 < / column> </row> <table> <table> table see original document page 68 </column> </row> <table> <table> table see original document page 69 </column> </row> <table> <table> table see original document page 70 </column> </row> <table> <table> table see original document page 71 </column> </row> <table> <table> table see original document page 72 < / column> </row> <table> <table> table see original document page 73 </column> </row> <table> <table> table see original document page 74 </column> </row> <table> <table> table see original document page 75 </column> </row> <table> <table> table see original document page 76 </column> </row> <table> <table> table see original document page 77 </column> </row> <table> <table> table see original document page 78 </column> </row> <table> <table> table see original document page 79 </column> </row> <table> <table> table see original document page 80 </column> </row> <table> <table> table see original document page 81 </column> </row> <table> <table> table see original document page 82 </column> </row> <table> <table> table see original document page 83 </column> </row> <table> <table> table see original document page 84 </column> </row> <table>

In a manner analogous to the examples shown above, as well as to the general description, the following compounds of formula (1-2) are obtained. <formula> formula see original document page 85 </formula>

Table 2

<table> table see original document page 85 </column> </row> <table> <table> table see original document page 86 </column> </row> <table> <table> table see original document page 87 < / column> </row> <table>

In a manner analogous to the examples shown above, as well as to the general description, the following compounds of formula (1-3) are obtained.

<formula> formula see original document page 87 </formula>

Table 3

<table> table see original document page 87 </column> </row> <table>

1H-NMR data of selected compounds:

.1-1-21 (400 MHz1 DMSO): 1.11 (d, 6 H), 2.14 (s, 3 H), 3.91 (m, 1 H), 5.55 (s, .2 H), 7.12 (s, 1 H), 7.28 (s, 1 H), 7.39 (s, 1 H), 7.55 (dd, 1 H), 7.76 (d, 1 7.99 (s, 1H), 8.08 (d, 1H), 8.43 (d, 1H), 8.61 (s, 1H), 10.12 (s, 1 H). .1-1-22 (400 MHz1 DMSO): 1.18 (d, 6 H), 2.14 (s, 3 H), 3.90 (m, 1 H), 5.87 (s, .2 H), 7.24 (s, 1 H), 7.42 (s, 1 H), 7.53 (s, 1 H), 7.55 (dd, 1 H), 7.80 (d, 1 H) .8.08 (d, 1 Η), 8.44 (d, 1 Η), 10.07 (s, 1 Η). 1-1-26 (400 MHz, DMSO): 2.14 (s, 3 H), 2.67 (d, 3 H), 5.93 (s, 2 H), 7.21 (s, 1 H ), 7.33 (s, 1 H), 7.40 (s, 1 H), 7.55 (dd, 1 H), 8.00 (d, 1 H), 8.08 (d, 1 H ), 8.45 (d, 1H), 10.12 (s, 1H). .1-1-48 (400 MHz, DMSO): 2.13 (s, 3 H), 5.69 (s, 2 H), 7.18 (s, 1 H), 7.41 (s, 2) H), 7.55 (dd, 1 H), 8.10 (d, 1 H), 8.45 (d, 1 H), 8.80 (s, 1 H), 10.19 (s, 1) H). .1-1-65 (400 MHz, DMSO): 1.06 (d, 6 H), 2.17 (s, 3 H), 3.95 (m, 1 H), 5.58 (s. 2 H), 7.15 (s, 1 H), 7.31 (s, 1 H), 7.42 (s, 1 H), 7.58 (dd, 1 H), 7.78 (d, 1 H), 7.92 (s, 1 H), 8.09 (d, 1 H), 8.46 (d, 1 H), 8.47 (s, 1 H), 10.04 (s , 1 H). .1-1-75 (400 MHz, DMSO): 1.09 (d, 6 H), 2.00 (s, 3 H), 2.15 (s, 3 H), 2.44 (dd. 1 H), 2.53 (dd, 1 H), 3.99 (m, 1 H), 5.86 (s, 2 H), 7.23 (s, 1 H), 7.33 (s, 1 H), 7.42 (s, 1 H), 7.55 (dd, 1 H), 7.92 (d, 1 H), 8.09 (d, 1 H), 8.44 (d , 1 H), 10.04 (s, 1 H).

.1-1-88 (400 MHz, DMSO): 2.14 (s, 3 H), 2.67 (d, 3 H), 5.38 (s, 2 H), 7.28 (s, 1 H), 7.33 (s, 1 H), 7.40 (s, 1 H), 7.55 (dd, 1 H), 7.96 (d, 2 H), 8.00 (d, 1 H), 8.08 (d, 1 H), 8.17 (d, 2 H), 8.46 (d, 1 H), 10.10 (s, 1 H). 1-104 (400 MHz, DMSO): 2.13 (s, 3 H), 2.64 (d, 3 H), 6.18 (s, 2 H), 7.28 (s, 1 H), 7.32 (s, 1 H), 7.40 (s, 1 H), 7.55 (dd, 1 H), 7.92 (d, 2 H), 8.00 (d, 1 H), 8.09 (d, 1 H), 8.30 (d, 2 H), 8.45 (d, 1 H), 10.10 (s, 1 H). .1-1-117 (400 MHz, DMSO): 1.02 (d, 6 H), 2.15 (s, 3 H), 3.34 (s, 3 H), 3.92 (m. 1H), 5.10 (s, 2 H), 7.17 (s, 1 H), 7.29 (s, 1 H), 7.39 (s, 1 H), 7.55 (dd, 1 H), 7.78 (d, 1H), 8.09 (d, 1H), 8.44 (d, 1H), 10.01 (s, 1H). -1-1-126 (400 MHz, DMSO): 0.99-1.10 (m, 4 H), 1.03 (d, 6 H), 2.15 (s, 3 H), 00-3.08 (m, 1 H), 3.92 (m, 1 H), 5.05 (s, 2 H), 7.16 (s, 1 H), 7.29 (s, 1 H ), 7.40 (s, 1 H), 7.55 (dd, 1 H), 7.78 (d, 1 H), 8.09 (d, 1 H), 8.44 (d, 1 H), 10.01 (s, 1H).

.1-1-139 (400 MHz, DMSO): 1.38 (s, 6 H), 2.14 (s, 3 H), 2.89 (s, 3 H), 3.68 (s,. 2H), 5.87 (s, 2 H), 7.21 (s, 1 H), 7.31 (s, 1 H), 7.40 (s, 1 H), 7.55 (dd, 1 H), 7.79 (s, 1H), 8.09 (d, 1H), 8.44 (d, 1H), 9.93 (s, 1H). .1-1-148 (400 MHz, DMSO): 2.14 (s, 3 H), 2.66 (d, 3 H), 6.18 (s, 2 H), 7.29 (s, 1 H), 7.32 (s, 1 H), 7.40 (s, 1 H), 7.55 (dd, 1 H), 7.70 (d, 1 H), 8.09 (d, 1 H), 8.11 (d, 1 H), 8.45 (s, 1 H), 8.46 (d, 1 H), 9.07 (s, 1 H), 10.10 (s , 1 H). 88

1-1-161 (400 MHz1 DMSO): 1.04 (d, 6 Η), 1.31 (s, 9 Η), 2.14 (s, 3 Η), 3.90 (m, 1 Η) , 5.46 (s, 2 Η), 7.11 (s, 1 Η), 7.29 (s, 1 Η), 7.39 (s, 1 Η), 7.55 (dd, 1 Η) , 7.78 (d, 1 Η), 8.09 (d, 1 Η), 8.40 (s, 1 Η), 8.44 (d, 1 Η), 10.10 (s, 1 Η) . 1-1-172 (400 MHz, DMSO): 1.04 (d, 6 H), 2.15 (s, 3 H), 3.90 (m, 1 H), 5.58 (s, 2 H ), 7.16 (s, 1 H), 7.55 (dd, 1 H), 7.70 (s, 1 H), 7.78 (s, 1 H), 7.93 (d, 1 H ), 8.09 (d, 1 H), 8.38 (s, 1 H), 8.45 (d, 1 H), 10.32 (s, 1 H). 1-1-175 (400 MHz, DMSO): 2.21 (s, 3 H), 4.16 (d, 1 H), 5.57 (s, 2 H), 7.16 (s, 1 H ), 7.55 (dd, 1 H), 7.70 (s, 1 H), 7.78 (s, 1 H), 7.86 (d, 1 H), 8.09 (d, 1 H ), 8.37 (s, 1H), 8.46 (d, 1H), 10.32 (s, 1H). 1-1-176 (400 MHz, DMSO): 2.19 (s, 3 H), 2.68 (d, 1 H), 5.88 (s, 2 H), 7.25 (s, 1 H ), 7.55 (dd, 1 H), 7.80 (s, 1 H), 7.97 (s, 1 H), 8.09 (d, 1 H), 8.15 (d, 1 H ),

8.44 (d, 1H), 10.40 (s, 1H).

1-1-180 (400 MHz, DMSO): 2.21 (s, 3 H), 4.16 (d, 1 H), 5.87 (s, 2 H), 7.27 (s,

1H), 7.55 (dd, 1 H), 7.77 (s, 1 H), 7.86 (s, 1 H), 8.09 (d, 1 H), 8.46 (d, 1 H), 8.96 (d, 1H), 10.34 (s, 1H).

1-1-182 (400 MHz, DMSO): 1.04 (d, 6 H), 2.19 (s, 3 H), 3.92 (m, 1 H), 5.57 (s,

2H), 6.74 (s, 1 H), 7.15 (s, 1 H), 7.55 (dd, 1 H), 7.70 (s, 1 H), 7.78 (s, 1 H), 7.91 (d, 1 H), 8.06 (s, 1 H), 8.09 (d, 1 H), 8.45 (d, 1 H), 10.30 (s, 1) H). 1-1-190 (400 MHz, DMSO): 2.21 (s, 3 H), 4.15 (d, 1 H), 5.69 (s, 2 H), 7.18 (s,

1 H), 7.53 (s, 1 H), 7.55 (dd, 1 H), 7.76 (s, 1 H), 7.85 (s, 1 H), 8.07 (d, 1 H),

8.45 (d, 1H), 8.95 (s, 1H), 10.30 (s, 1H).

1-1-195 (400 MHz, DMSO): 1.11 (d, 6 H), 2.00 (s, 3 H), 2.15 (s, 3 H), 2.44 (dd, 1 H ), 2.53 (dd, 1 H), 4.02 (m, 1 H), 5.57 (s, 2 H), 7.08 (d, 1 H), 7.15 (s, 1 H ), 7.20 (d, 1 H), 7.55 (dd, 1 H), 7.84 (d, 1 H), 8.09 (d, 1 H), 8.37 (s, 1 H ), 8.45 (d, 1H), 10.30 (s, 1H).

1-1-196 (400 MHz, DMSO): 2.15 (s, 3 H), 4.34 (d, 1 H), 5.57 (s, 2 H), 6.19 (d, 1 H ), 6.29 (d, 1 H), 7.10 (s, 1 H), 7.13 (d, 1 H), 7.22 (d, 1 H), 7.43 (s, 1 H) ), 7.55 (dd, 1 H), 8.08 (d, 1 H), 8.38 (s, 1 H), 8.46 (d, 1 H), 8.55 (t, 1 H ), 10.30 (s, 1H). 1-1-201 (400 MHz, DMSO): 2.14 (s, 3 H), 4.33 (d, 1 H), 5.57 (s, 2 H), 6.19 (d, 1 H ), 6.29 (d, 1 H), 7.10 (s, 1 H), 7.33 (s, 1 H), 7.44 (2 d, 2 H), 7.55 (dd, 1 H), 8.08 (d, 1 H), 8.37 (s, 1 H), 8.45 (d, 1 H), 8.55 (t, 1 H), 10.34 (s, 1 H). 1-1-208 (400 MHz1 DMSO): 2.14 (s, 3 Η), 4.33 (d, 1 Η), 5.57 (s, 2 Η), 6.19 (d,

.1Η), 6.29 (d, 1 Η), 7.13 (s, 1 Η), 7.45 (s, 1 Η), 7.55 (dd, 1 Η), 7.75 (s, 1 Η), .7.80 (s, 1 Η), 8.08 (d, 1 Η), 8.38 (s, 1 Η), 8.69 (br s, 1 H), 8.55 ( t, 1H), 10.34 (s, 1H).

.1-1-241 (400 MHz, DMSO): 1.02 (d, 3 H), 2.11 (s, 3 H), 3.91 (m, 1 H), 5.57 (s,

(2H), 7.12 (s, 1 H), 7.55 (dd, 1 H), 7.57 (s, 1 H), 7.69 (s, 1 H), 7.76 (d, 1 H),

.8.08 (d, 1 H), 8.37 (s, 1 H), 8.45 (d, 1 H), 10.02 (s, 1 H).

.1-1-243 (400 MHz, DMSO): 2.10 (s, 3 H), 2.67 (d, 3 H), 3.07 (q, 2 H), 5.57 (s, 2 H), 7.13 (s, 1 H), 7.55 (dd, 1 H), 7.60 (s, 1 H), 7.70 (s, 1 H), 7.98 (d, 1H), 8.10 (d, 1H), 8.38 (s, 1H), 8.45 (d, 1H), 10.09 (s, 1H).

.1-1-244 (400 MHz, DMSO): 0.99 (t, 3 H), 2.11 (s, 3 H), 3.07 (q, 2 H), 5.87 (s. 2 H), 7.21 (s, 1 H), 7.55 (dd, 1 H), 7.59 (s, 1 H), 7.70 (s, 1 H), 7.98 (s, 1 H),

.8.09 (d, 1 H), 8.45 (d, 1 H), 10.05 (s, 1 H).

.1-1-248 (400 MHz, DMSO): 1.01 (d, 6 H), 2.10 (s, 3 H), 3.89 (m, 1 H), 5.56 (s. 2 H), 6.73 (s, 1 H), 7.11 (s, 1 H), 7.55 (dd, 1 H), 7.56 (s, 1 H), 7.76 (s, 1 H), 7.75 (d, 1 H), 8.04 (s, 1 H), 8.09 (d, 1 H), 8.45 (d, 1 H), 10.01 (s , 1 H). -1-1-274 (400 MHz, DMSO): 0.99 (t, 3 H), 2.10 (s, 3 H), 3.07 (q, 2 H), 5.68 (s, 2H) ), 7.15 (s, 1 H), 7.55 (dd, 1 H), 7.60 (s, 1 H), 7.97 (s, 1 H), 8.08 (d, 1 H ), 8.45 (d, 1H), 10.09 (s, 1H). -1-1-275 (400 MHz, DMSO): 0.40-0.47 (m, 2 H), 0.55-0.60 (m, 2 H), 2.10 (s, 3 H) , 2.65-2.71 (m, 1 H), 5.69 (s, 2 H), 7.17 (s, 1 H), 7.55 (dd, 1 H), 7.56 (s , 1 H), 7.69 (s, 1 H), 8.00 (d, 1 H), 8.08 (d, 1 H), 8.45 (s, 1 H), 8.79 (d , 1 H) .10.05 (s, 1 H).

-1-1-276 (400 MHz, DMSO): 0.41-0.45 (m, 2 H), 0.56-0.61 (m, 2 H), 2.10 (s, 3 H) , 2.65-2.71 (m, 1 H), 5.57 (s, 2 H), 7.14 (s, 1 H), 7.55 (dd, 1 H), 7.55 (s , 1 H), 7.69 (s, 1 H), 8.01 (d, 1 H), 8.08 (d, 1 H), 8.38 (s, 1 H), 8.46 (d 1 H) .10.02 (s, 1 H).

-1-1-279 (400 MHz, DMSO): 1.34-1.60 (m, 6 H), 1.71-1.78 (m, 2 H), 2.10 (s, 3 H) 4.01-4.08 (m, 1 H), 5.87 (s, 2 H), 7.21 (s, 1 H), 7.55 (dd, 1 H), 7.57 (s , 1 H), 7.70 (s, 1 H), 7.85 (d, 1 H), 8.07 (d, 1 H), 8.43 (s, 1 H), 10.02 (s , 1 H). -1-1-280 (400 MHz, DMSO): 1.13-1.51 (m, 20 H), 1.71-1.78 (m, 2 H), 2.07 (s, .3H) , 3.93-3.96 (m, 1 H), 5.83 (s, 2 H), 7.13 (s, 1 H), 7.55 (dd, 1 H), 7.61 (s , 90

Δ), 7.68 (d, 1 Η), 8.02 (s, 1 Η), 8.07 (d, 1 Η), 8.43 (s, 1 Η), 10.02 (s, 1) Η). 1-1-282 (400 MHz, DMSO): 1.36 (s, 2 Η), 1.56-1.65 (m, 2 Η), 1.84-1.94 (m, 2 Η), 2.07 (s, 3 Η), 4.18-4.24 (m, 1 Η), 5.87 (s, 2 Η), 7.18 (s, 1 Η), 7.55 (dd, 1 Η), 7.59 (s, 1 Η), 7.70 (d, 1 Η), 8.07 (s, 1 Η), 8.19 (d, 1 Η), 8.43 (s, 1 Η), 10.02 (s, 1 Η).

1-1-290 (400 MHz, CDCl 3): 2.90 (d, 3), 5.74 (s, 2), 6.10 (d, 1), 7.23 (s, 1) ), 7.23 (s, 1), 7.28 (s, 1), 7.40 (dd, 1), 7.87 (d, 1), 8.46 (d, 1) ), 9.74 (s, 1).

1-1-296 (400 MHz, CDCl 3): 5.54 (s, 2), 5.62 (s, 1), 6.11 (s, 1), 7.12 (s, 1) ), 7.39 (s, 1), 7.40 (dd, 1), 7.48 (s, 1), 7.90 (d, 1), 7.94 (s, 1) ), 8.48 (d, 1 Η), 9.45 (s, 1 Η).

1-1-310 (400 MHz, CDCl3): 4.18 (d, 2 Η), 5.48 (s, 2 Η), 6.74 (t, 1 Η), 7.08 (s, 1 Η) ), 7.32 (s, 1), 7.43 (dd, 1), 7.48 (s, 1), 7.92 (d, 1), 7.94 (s, 1) ), 8.50 (d, 1), 8.93 (s, 1). 1-1-314 (400 MHz, CDCl3): 1.10 (d, 6), 4.08 (m, 1), 5.50 (s, 2), 5.92 (d, 1) ), 6.57 (s, 1 Η), 7.15 (s, 1 Η), 7.28 (s, 1 Η), 7.39 (s, 1 Η), 7.40 (dd, 1 Η ), 7.57 (s, 1), 7.87 (d, 1), 8.48 (d, 1), 9.65 (s, 1). 1-1-324 (400 MHz1 CDCl3): 1.24 (d, 3 Η), 2.10 (s, 3 Η), 2.60 (m, 2 Η), 4.22 (m,

1Η), 5.51 (d, 1 Η), 5.58 (d, 1 Η), 6.13 (d, 1 Η), 7.17 (s, 1 Η), 7.35 (s, 1 Δ), 7.39 (s, 1 Η), 7.40 (dd, 1 Η), 7.87 (d, 1 Η), 7.90 (s, 1 Η), 8.48 (d, 1 Η), 9.60

(s, 1).

1-1-331 (400 MHz, CDCl3): 0.55 (m, 2 Η), 0.85 (m, 2 Η), 2.16 (s, 3 Η), 2.77 (m, 1 Η) ), 5.57 (s, 2), 6.18 (d, 1), 7.12 (s, 1), 7.18 (s, 1), 7.24 (s, 1) ), 7.41 (dd, 1), 7.88 (d, 1), 8.35 (s, 1), 8.48 (d, 1), 10.15 (s, 1) ). 1-1-334 (400 MHz, CDCl3): 1.24 (d, 6 Η), 2.23 (s, 3 Η), 4.18 (m, 1 Η), 5.58 (s,

2Η), 5.99 (d, 1 Η), 7.12 (s, 1 Η), 7.28 (s, 1 Η), 7.40 (dd, 1 Η), 7.58 (d, 1 Δ), 7.88 (d, 1 Η), 8.36 (s, 1 Η), 8.48 (d, 1 Η), 10.62 (s, 1 Η).

1-1-340 (400 MHz, CDCl3): 1.24 (d, 6), 4.08 (m, 1), 5.58 (s, 2), 5.92 (d, 1) ), 7.21 (s, 1), 7.30 (s, 1), 7.32 (s, 1), 7.40 (dd, 1), 7.77 (d, 1) ), 8.36 (s, 1), 8.48 (d, 1), 10.06 (s, 1).

1-1-345 (400 MHz, CDCl3): 0.55 (m, 2), 0.85 (m, 2), 2.77 (m, 1), 5.58 (S, 2) ), 6.20 (d, 1 Η), 7.14 (s, 1 Η), 7.20 (s, 1 Η), 7.22 (s, 1 Η), 7.40 (dd, 1 Η ), 7.88 (d, 1 Η), 8.32 (s, 1 Η), 8.45 (d, 1 Η), 10.12 (s, 1 Η). .1-1-354 (400 MHz, CDCl3): 1.21 (d, 6), 4.15 (m, 1), 5.58 (s, 2), 7.16 (s,. 1 Η), 7.18 (s, 1 Η), 7.40 (dd, 1 Η), 7.58 (s, 1 Η), 7.75 (s, 1 Η), 7.84 (d, 1 δ), 8.38 (s, 1 Η), 8.48 (d, 1 Η), 10.95 (s, 1 Η).

Δ-2-4 (400 MHz, CDCl3): 1.74 (m, 3 Η), 2.16 (m, 2 Η), 2.40 (m, 1 Η), 2.86 (d, .3 Η), 3.70 (m, 1 Η), 3.88 (m, 1 Η), 5.75 (s, 2 Η), 5.80 (m, 1 Η), 6.45 (s, 1 Δ) .6.80 (S, 1 Η), 7.16 (S, 1 Η), 7.42 (s, 1 Η), 7.56 (s, 1 Η), 9.08 (s, 1 Η). Δ-2-7 (400 MHz, CDCl3): 1.24 (m, 6 Η), 1.74 (m, 3 Η), 2.20 (m, 2 Η), 2.40 (m, .1 Η), 3.70 (m, 1 Η), 3.88 (m, 1 Η), 4.10 (m, 1 Η), 5.80 (m, 3 Η), 6.25 (s, 1 Δ) .6.80 (s, 1 Η), 7.40 (s, 1 Η), 7.52 (s, 1 Η), 8.85 (s, 1 Η).

Determination of the 1 H-NMR data shown above is performed with a Bruker Avance 400 equipped with a BEST system (60 μΙ cell volume) or with a Bruker Avance 400 with tetramethylsilane as reference (0.0 ppm) and with CDCl3 at 298 Kelvin or d6-DMSO at 304 Kolvin. Signal dissociation is characterized by s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = double doublet.

The determination of the IogP values given in the tables and preparation examples above is carried out in accordance with EEC 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18 ). Temperature: 43 ° C.

Determination with LC-MS on acidity scale is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as eluents; linear gradient from 10% acetonitrile to .95% acetonitrile.

Calibration is performed with unbranched alkan-2-ones (with .3 to 16 carbon atoms), whose IogP values are known (determination of IogP values based on retention times by linear interpolation between two alkanones). successive).

Lambda-max values are determined on the basis of UV spectra from 200 nm to 400 nm at the maximum of the chromatographic signals. Preparation of starting materials of formula (V) 92

Example 2

2-5- (3,5-bistrifluoromethylpyrazol-M-ylmethyl) -2- (3-chlorop 6-chloro-8-methylbenzoyl), 31oxazin-4-one

Under argon 0.12 ml (1.60 mmol) of methanesulfonic acid chloride in 3 ml of acetonitrile are cooled to 0 ° C and then a solution of 540 mg (1.228 mmol) of 5- (3, 5-bis-trifluoromethyl-pyrazol-1-ylmethyl) -2- (3-chloro-pyridin-2-yl) -2H-pyrazol-3-carboxylic acid in 0.17 ml (2.09 mmol) of pyridine and 6 ml of acetonitrile is added to the drops. Stir for 15 minutes at this temperature and then add a solution of 228 mg (1.228 mmol) of 2-amino-5-chloro-3, N-dimethyl benzamide in 0.35 mL (4 mL). , 30 mmol) pyridine and 6 ml acetonitrile. After a further 15 minutes at 0 ° C, 0.12 ml (1.60 mmol) of methanesulfonic acid chloride is added and overnight slowly warmed to room temperature. Remove the solvent in vacuo, add 15 ml of water and aspirate the crystals formed. Yield: 500 mg (logP: 5.11). Preparation of starting materials of formula (IV)

Example 3

5- (3,5-Bistrifluormethyl-pyrazol-1-ylmethyl) -2- (3-chloro-pyridin-2-yl) -2H-pyrazol-3-carboxylic acid:

To a solution of 610 mg (1.34 mmol) of 5- (3,5-bis-trifluoromethyl-pyrazol-1-ylmethyl) -2- (3-chloro-pyridin-2-yl) -2H acid methyl ester -pyrazol-3-carboxylic acid in 9 ml of ethanol is added dropwise with a solution of 699 mg (1.78 mmol) of sodium hydroxide in 7 ml of water. Stir for 2 hours at room temperature, concentrate on the rotary evaporator to about 5 ml. 5 ml of tert-butyl methyl ether is added and then the organic phase is washed with water. The combined aqueous phases are adjusted to a pH of about 3 with concentrated hydrochloric acid and extracted three times with 50 ml each of ethyl acetate. The combined organic phases are dried over magnesium sulfate and then the solvent is removed on the rotary evaporator. Yield: 560 mg (logP: 2.86). Preparation of starting materials of formula (IV) Example 4

5- (3,5-Bis-trifluoromethylpyrazol-1-ylmethyl) -2- (3-chloropyridin-2-yl) -2H-pyrazol-3-carboxylic acid methyl ester:

A solution of 700 mg (2.03 mmol) of? 2- (3-chloropyridin-2-yl) -5-methanesulfonyloxymethyl-2H-pyrazol-3-carboxylic acid methyl ester in 15 ml of acetonitrile is successively added to 336 mg (2.43 mmol) of potassium carbonate and 413 mg (2.03 mmol) of 3,5-bis (trifluoromethyl) pyrazole and then stirred for one hour at 60 ° C. After cooling to room temperature, the solvent is concentrated on the rotary evaporator, added to water and extracted three times with 50 ml each of ethyl acetate. The combined organic phases are dried over magnesium sulfate and then the solvent is removed on the rotary evaporator. Yield: 970 mg (logP: 3.71).

Preparation of starting materials of formula (VII) Example 5

2- (3-Chloropyridin-2-yl) -5-methanesulfonyloxymethyl-2H-pyrazol-3-carboxylic acid methyl ester

Under argon, 2.10 g (7.85 mmoles) of 2- (3-chloropyridin-2-yl) -5-hydroxymethyl-2H-pyrazol-3-carboxylic acid methyl ester are previously added to 13 ml of dichloromethane, cooled to 0 ° C and successively added dropwise to 1.64 ml (11.8 mmols) triethylamine and 0.67 ml (8.63 mmols) methanesulfonic acid chloride. It is allowed to stir for 30 minutes at this temperature, diluted with dichloromethane (50 ml) and successively washed with 50 ml saturated aqueous sodium hydrogen sulfate solution, 10% aqueous hydrochloric acid and sodium chloride solution respectively. saturated aqueous. The organic phase is dried over magnesium sulfate and then the solvent is removed on the rotary evaporator. Yield: 2.65 g (logP: 1.55)

Preparation of starting materials of formula (X)

Example 6

2- (3-Chloropyridin-2-yl) -5-hydroxymethyl-2H-pyrazol-3-carboxylic acid methyl ester:

Under argon, 12.3 g (41.7 mmols) of 1- (3-chloropyridin-2-yl) -1 H -pyrazol-3,5-dicarboxylic acid dimethyl ester are previously introduced into 430 ml of cold tetrahydrofuran at -72 ° C and added dropwise to 100 ml (100 mmol of a 1 M solution in hexane) of diisobutylammonium hydride. Allow to warm overnight to 0 ° C and carefully add 65 ml of water. The solvents are removed on the rotary evaporator and the residue is exhaustively extracted on the Soxhlet with methanol. After removing the solvent, the residue is purified on silica gel (cyclohexane / ethyl acetate = 2: 1 → 1: 1).

Yield: 9.26 g (logP: 1.26).

Preparation of starting materials of formula (XI)

Example 7

1- (3-Chloropyridin-2-yl) -1H-pyrazol-3,5-dicarboxylic acid dimethyl ester

To a solution of 15.6 g (64.8 mmol) of 2-pyrrolidine-4-oxo-2-pentenedicarboxylic acid dimethyl ester and 20.4 g (64.8 mmol) of 3-chloro-2-pyridin-2-pyridinecarboxylic acid. 2-ylhydrazine toluenesulfonic acid salt in 84 ml methanol, a pinch of toluenesulfonic acid is placed and heated for 5 hours at 50 ° C. Then 12.3 g (64.8 mmol) of toluenesulfonic acid monohydrate is added and stirred initially for 1 hour at 50 ° C and 1 hour under reflux. After cooling to 0 ° C, precipitated crystals are aspirated and filtered through silica gel (cyclohexane / acetic ester = 1: 1). Yield: 8.56 g (logP: 1.97).

Examples regarding the biological efficacy of the compounds according to the invention

Example # 1

Heliothis virescens test

Solvent: 1% N-Methylpyrrolidone (NMP)

.1% diacetonic alcohol

Dye: Shiny sulfoflavin to dye water.

To produce a suitable active ingredient preparation, the active substance is mixed with the indicated solvent amounts and the concentrate is diluted with tinted water to the desired concentration.

Heliothis virescens eggs are treated with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100% means that all eggs / larvae have been killed; 0% means that none of the eggs / larvae have been killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table. Heliothis virescens test

active substance concentration of active substance in ppm mortality rate after 6-7 days in% 1-1-13 300 100 1-1-14 300 100 1-1-15 300 100

Example # 2

Mvzus persicae Test

Solvent: 1% N-Methylpyrrolidone (NMP)

1% Diacetonic Alcohol Dye: Brilliant sulfoflavin to dye water.

To produce a suitable active ingredient preparation, the active substance is mixed with the indicated solvent amounts and the concentrate is diluted with tinted water to the desired concentration.

An active substance preparation of the desired concentration for absorption is made available to Myzus persicae.

After the desired time, the effect is determined in%. In this case, 100% means that all aphids have been killed; 0% means that the aphids were not killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table. Myzus persicae test

active substance active substance concentration in ppm mortality rate after 6-7 days in% 1-1-13 30 100 1-1-14 30 100 1-1-15 30 100

Example # 3

Aedes aeqypti Test

Solvent: 1% N-Methylpyrrolidone (NMP)

1% Diacetonic Alcohol Dye: Brilliant sulfoflavin to dye water.

To produce a suitable active ingredient preparation, the active substance is mixed with the indicated solvent amounts and the concentrate is diluted with tinted water to the desired concentration.

Aedes aegypti larvae are treated with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100% means that all Aedes aegypti were killed; 0% means that the Aedes aegypti were not killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table Test with Aedes aegypti

active substance active substance concentration in ppm mortality rate after 2-4 days in% 1-1-13 30 100 1-1-14 30 100 1-1-15 30 100

Example # 4

Thesis with Diabrotica undecimpunctata

Solvent: 1% N-Methylpyrrolidone (NMP)

1% Diacetonic Alcohol 97

Dye: Shiny sulfoflavin to dye water.

To produce a suitable active ingredient preparation, the active substance is mixed with the indicated solvent amounts and the concentrate is diluted with tinted water to the desired concentration.

Diabrotica undecimpunctata eggs are treated with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100% means that all eggs / larvae have been killed; 0% means that none of the eggs / larvae have been killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table Test with Diabrotica undecimpunctata

<table> table see original document page 98 </column> </row> <table>

Example # 5

Phaedon test (spray treatment) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: 0.5 parts by weight alkyl polyglycolic ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Chinese cabbage (Brassica pekinensis) discs are sprayed with an active substance preparation of the desired concentration and then dried, infested with horseradish beetle (Phaedon cochleariaé) larvae.

After the desired time, the effect is determined in%. In this case, 100% means that all larvae of the beetle have been killed; 0% means that the larvae were not killed.

In this test, for example, the following compounds of the preparation examples show> 80% efficacy with an application amount of 100 g / ha: Example No. 1-1-2, 1-1-3, 1-1- 4, 1-1-5, 1-1-6, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, .1-1-15 , 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-22, 1-1-23, 1-1-24, 1-1-25, 1 -1-28, 1-1- .29, 1-1-30, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1- 1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-217, 1-1-218, 1-1-219, 1-1 -220, 1-1-222, 1-1-223, 1-1-224, 1-1-225, 1-1- .226, 1-1-38, 1-1-42, 1-1- 43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1-50, .1-1-51 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1 -1-60, 1-1- .61, 1-1-62, 1-1-63, 1-1-64, 1-1-65, 1-1-66, 1-1-68, 1- 1-69, 1-1-70, 1-1-71, 1-1-72, 1-1-73, 1-1-74, 1-1-75, 1-1-76, 1-1 -77, 1-1-78, 1-1-79, 1-1-80, 1-1-81, 1-1-82, 1-1-83, .1-1-84, 1-1- 85, 1-1-86, 1-1-87, 1-1-92, 1-1-93, 1-1-97, 1-1-99, 1-1-100, 1-1-101, 1-1-113, 1-1-120, 1-1-121, 1-1-125, 1-1-128, 1-1-129, 1-1-130, 1-1 -131, 1-1-134, 1-1-135, 1-1-137, 1-1-138, 1-1-139, 1-1-140, 1-1-141, 1-1- 142, 1-1-144, 1-1-145, 1-1-146, 1-1-147, 1-1-148, 1-1-149, 1-1-150, 1-1-151 , 1-1-152, 1-1-155, 1-1-156, 1-1-157, 1-1-158, 1-1-163, 1-1-165, 1-1-166, 1-1-167, 1-1-168, 1-1-169, 1-1-170, I- .1-171, 1-1-172, 1-1-173, 1-1-174, 1 -1-175, 1-1-176, 1-1-177, 1-1-178, 1-1-179, 1-1-180, 1-1-181, 1-1-182, 1- 1-183, 1-1-184, 1-1-185, 1-1-186, 1-1-187, 1-1-188, 1-1-189, 1-1-190, 1-1 -191, 1-1-192, 1-1-193, 1-1-195, 1-1-196, 1-1-199, 1-1-201, 1-1-203, 1-1- 204, 1-1-206, 1-1-207, 1-1-208, 1-1-209, 1-1-210, 1-1-211, 1-1-212, I- .1-213 , 1-1-214, 1-1-215, 1-1-216, 1-1-227, 1-1-228, 1-1-230, 1-1-231, 1-1-233, I -1-234, 1-1-235, 1-1-236, 1-1-237, 1-1-238, 1-1-239, 1-1-240, 1-1-241, 1- 1-242, 1-1-243, 1-1-244, 1-1-245, 1-1-246, 1-1-247, 1-1-248, 1-1-251, 1-1 -252, 1-1-253, 1-255, 1-1-258, 1-1-259, 1-1-260, 1-1 -267, 1-1 -272,1-1- 273, 1-1 -274, 1-1-275, 1-1-276, 1-1-277, 1-1-279, 1-1-282, 1-1-283, 1-1-284 , 1-1-285 , 1-1-286, 1-1-287, 1-1- .288, 1-1-289, 1-1-290, 1-1-291, 1-1-292, 1-1-293, 1-1-294, 1-1-295, 1-1-296, 1-1- .297, 1-1-298, 1-1-299, 1-1-300, 1-1-302, 1 -1-303, 1-1-304, 1-1-305, 1-1-307, 1-1- .308, 1-1-309, 1-1-310, 1-1-312, 1- 1-313, 1-1-324, 1-1-326, 1-1-327, 1-1-328, 1-1- .329, 1-1-330, 1-1-331, 1-1 -332, 1-1-333, 1-1-334, 1-1-335, 1-1-336, 1-1-337, 1-1- .338, 1-1-339, 1-1- 340, 1-1-342, 1-1-343, 1-1-346, 1-1-347, 1-1-348, 1-1-349, 1-1- .350, 1-1-352 , 1-1-353, 1-1-354, 1-1-355, I-2-2. 99

Example # 6

Spodoptera frugiperda test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylpolyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by soaking the active substance preparation of the desired concentration and infested with beet caterpillars (Spodoptera frugiperda) while the leaves are still moist.

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table.

Spodoptera frugiperda test

<table> table see original document page 100 </column> </row> <table> active substance active substance concentration in g / ha mortality rate after 7 days in% 1-1-14 100 100 1-1-15 100 100 1-1-16 100 100 1-1-17 100 100 1-1-18 100 100 1-1-19 100 100 1-1-20 100 100 1-1-21 100 100 1-1-22 100 100 1-1-23 100 100 1-1-24 100 100 1-1-25 100 100 1-1-26 100 100 1-1-27 20 83 1-1-28 100 100 1-1-29 100 100 1-1-30 100 100 1-1-31 100 100 1-1-32 100 100 1-1-33 100 100 1-1-34 100 100 1-1-35 100 100 1-1-36 100 100 1-1-37 100 100 1-1-39 100 100 1-1-40 100 100

Example # 7

Spigoptera test small

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with emulsifier-containing water. to the desired concentration. If it is necessary to add ammonium salts, penetration enhancers or ammonium salts and penetration enhancers, these are added by pipetting at a concentration of 1000 ppm after dilution in each case to the prepared preparation solution. Examples 1-1-3, 1-1-5, 1-1-6, 1-1-8, 1-1-22 are tested without addition of ammonium salts or penetration enhancers.

Cabbage (Brassica oleracea) plants are treated by spraying the active substance preparation to the desired concentration and infested with beet pupae (Spodoptera exigua) caterpillars while the leaves are still moist.

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 4 ppm:

Example No. 1-1-3, 1-1-5, 1-1-6, 1-1-8, 1-1-11, 1-1-31, 1-1-35, 1-1-47 1-1-48, 1-1-52, 1-1-53, 1-1-55, 1-1-57, 1-1-170, 1-1-291, 1-1-295, 1 -1-296, 1-1-297, 1-1-299, I-1-54.

Example # 8

Plutella xylostella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. If it is necessary to add ammonium salts, penetration enhancers or ammonium salts and penetration enhancers, these are added by pipetting at a concentration of 1000 ppm after dilution in each case to the prepared preparation solution. Examples 1-1-3, 1-1-5, 1-1-6, 1-1-8, 1-1-22 are tested without addition of ammonium salts or penetration enhancers.

Cabbage leaves (Brassica oleracea) are treated by spraying the active substance preparation to the desired concentration and infested with cockroach cockroach (Plutella xylostella) caterpillars, while the leaves are still moist.

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 20 ppm:

Example No. 1-1-3, 1-1-5, 1-1-6, 1-1-8, 1-1-22, 1-1-65, 1-1-239, 1-1-240 1-1-245, 1-15 1-217, 1-1-220, 1-1-223, 1-1-224, 1-1-31, 1-1-55, 1-1-56, 1-1-57, 1-1-63, 1-1-66, I- 1-68, 1-1-69, 1-1-76, 1-1-92, 1-1-97, 1- 1-98, 1-1-101, 1-1-113, 1-1-121, 1-1-147, 1-170, 1-1-192, 1-1-195, 1-1- 204, 1-1-206, 1-1-209, 1-1-210, 1-1-212, 1-1-215, I-1-238, 1-1-244, 1-1-247, 1-1-248, 1-1-249, 1-1-250, 1-1-251, 1-1-274, 1-1-275, I-1-276, 1-1-291, 1- 1-295, 1-1-296, 1-1-297, 1-1-299, 1-1-25, 1-1-35, 1-1-36, 1-1-38, 1-1- 43, 1-1-46, 1-1-47, 1-1-48, 1-1-52, 1-1-53, 1-1-54, 1-1-104, 1-1-106, 1-1-107, 1-108, 1-1-143, 1-1-88, 1-1-139.

Example # 9

Spodoptera frugiperda test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by soaking the active substance preparation of the desired concentration and infested with beet caterpillars (Spodoptera frugiperda) while the leaves are still moist.

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table.

Spodoptera fruqiperda test

<table> table see original document page 104 </column> </row> <table>

Example # 10

Heliothis armiqera test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. If it is necessary to add ammonium salts, penetration enhancers or ammonium salts and penetration enhancers, these are added by pipetting at a concentration of 1000 ppm after dilution in each case to the prepared preparation solution. Examples 1-1-3, 1-1-5, 1-1-6, 1-1-8 and 1-1-22 are tested without addition of ammonium salts or penetration enhancers.

Cotton plants (Gossypium hirsutum) are treated by spraying the desired concentration of active substance preparation and infested with caterpillars of the encapsulated cotton worm (Heliosthis armigera) while the leaves are still moist. 104

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 20 ppm:

Example No. 1-1-3, 1-1-5, 1-1-6, 1-1-8, 1-1-22, 1-1-63, 1-1-65, 1-1-66 , 1-1-68, 1-1-69, 1-1-192, 1-1-240, 1-1-245, 1-1-217, 1-1-220, 1-1-223, 1 -1-224, 1-1-31, 1-1-35, 1-1-36, 1-1-38, 1-1-43, 1-1-46, 1-1-47, 1-1 -48, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1- 56, 1-1-57, 1-1-76, 1-1-88 1-1-131, 1-1-139, 1-1-92, 1-1-97, 1-1-98, 1-1-100, 1-1-101, 1-1-113, 1 -1-121, 1-1-147, 1-1-170, 1-1-195, 1-1-204, 1-1-206, 1-1-212, 1-1-215, 1-1 -238, 1-1-244, 1-1-247, 1-1-248, 1-1-249, 1-1-250, 1-1-251, 1-1-274, 1-1-275 , 1-1-276, 1-1-291, 1-1-295, 1-1-296, 1-1-297, 1-1-299, 1-1-104, 1-1-106, 1 -1-107, 1-1-108, 1-1-143. Example # 11

Spodoptera test is small; resistant strain Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylpolyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. If it is necessary to add ammonium salts, penetration enhancers or ammonium salts and penetration enhancers, these are added by pipetting at a concentration of 1000 ppm after dilution in each case to the prepared preparation solution. Examples 1-1-5, 1-1-6,1-1-22 are tested without addition of ammonium salts or penetration enhancers.

Cabbage (Brassica oleracea) plants are treated by spraying the active substance preparation to the desired concentration and infested with beet pupae (Spodoptera exigua, resistant strain), while the leaves are still moist.

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that the caterpillars were not killed.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 4 ppm:

Example 1-1-5, 1-1-6, 1-1-22, 1-1-31, 1-1-35, 1-1-38, 1-1-46, 1-1-47 1-1-48, 1-1-52, 1-1-53, 1-1-54, 1-1-56, 1-1-57, 1-1-170, 1-1-295, 1 -1-296, 1-1-297, 1-1-299.

Example # 12

Liriomyza trifolii

Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylpolyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Bean leaf discs (Phaseolus vulgaris), which are infested with fly larvae (Liriomyza trifolii), are sprayed with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100%, that all mine flies were killed; 0% means that the mine flies were not killed.

In this test, for example, the following compounds of the preparation examples show good efficacy: see table.

Liriomvza trifolii test

<table> table see original document page 106 </column> </row> <table>

Example # 13

Test with Lucilia cuprina 106

Solvent: Dimethyl Sulfoxide

To produce a suitable preparation of the active substance, 1 part by weight of the active substance is mixed with the indicated amount of water and the concentrate is diluted with water to the desired concentration.

Containers, which contain horse meat, which has been treated with the active substance preparation of the desired concentration, are infested with Lucilia cuprina larvae.

After the desired time, mortality is determined in%. In this case, 100% means that all the larvae were killed; 0% means that the larvae were not killed.

In this test, for example, the following compounds of the preparation examples show an effect of> 80% with an application amount of 100 ppm:

Example No. 1-1-1, 1-1-2, 1-1-3, 1-1-4, 1-1-5, 1-1-6, 1-1-7, 1-1-8 , 1-1-9, 1-1-12, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1 -1-21, 1-1-22, 1-1-29, 1-1-30, 1-1-31, I-1-217, 1-1-220, 1-1-223, 1-1 -224, 1-1-42, 1-1-43, 1-1-46, 1-1-47, 1-1-48, 1-1-52, I-1-53, 1-1-54 1-1-55, 1-1-56, 1-1-57, 1-1-64, 1-1-65, 1-1-66, 1-1-67, 1-1-68, 1 -1-74, 1-1-88, 1-1-92, 1-1-97, 1-1-104, 1-1-107, 1-1-108, 1-1-109, 1-1 -111, 1-1-114, 1-1-122, 1-1-123, 1-1-192, 1-1-238, 1-1-239, 1-1-240, 1-1-244 1-1-247, 1-1-274, 1-1-275, 1-1-291, 1-1-295, 1-1-296, 1-1 -297, 1-1-299, 1 -1323. Example # 14

Boophilus microplus test (injection) Solvent: dimethyl sulfoxide

To produce a suitable preparation of the active substance, 1 part by weight of the active substance is mixed with the indicated amount of water and the concentrate is diluted with water to the desired concentration.

The active substance solution is injected into the abdomen (Boophilus microplus), the animals are transferred to capsules and stored in a climate-controlled environment.

After the desired time, the effect is determined in%. In this case, 100% means that none of the ticks laid fertile eggs.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 20 Mg / animal:

Example No. 1-1-1, 1-1-2, 1-1-3, 1-1-4, 1-1-5, 1-1-6, 1-1-7, 1-1-8 , 1-1-9, 1-1-12, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1 -1-21, 1-1-29, 1-1-30, 1-1-31, 1-1-217, 1-1-222, 1-1-223, 1-1-224, 1-1 -42, 1-1-43, 1-1-46, 1-1-47, 1-1-48, 1-1-52, 1-1-53, I-1-54, 1-1-55 1-1-56, 1-1-57, 1-1-64, 1-1-65, 1-1-66, 1-1-67, 1-1-68, 1-1-74, 1 -1-88, 1-1-92, 1-1-97, 1-1-104, 1-1-107, 1-1-108, 1-1-109, 1-1-111, 1-1 -114, 1-1-122, 1-1-123, 1-1-192, 1-1-238, 1-1-239, 1-1-240, 1-1-244, 1-1-247 , 1-1-274, 1-1-275, 1-1- 291, 1-1-295, 1-1-296, 1-1-297, 1-1-299, 1-1-323. Example # 15

Domestic Musca Test Solvent: Dimethylsulfoxide

To produce a suitable preparation of the active substance, 1 part by weight of the active substance is mixed with the indicated amount of water and the concentrate is diluted with water to the desired concentration.

Containers, which contain a sponge that has been treated with the active ingredient preparation of the desired concentration, are infested with adult Musca domestica.

After the desired time, mortality is determined in%. In this case, 100% means that all the flies were killed; 0% means that the flies were not killed. Examples 1-1-16, 1-1-19 and 1-1-30 are a knock-down effect.

In this test, for example, the following compounds of the preparation examples show a> 80% effect with an application amount of 100 ppm:

Example No. 1-1-16, 1-1-19, 1-1-30, 1-1-217, 1-1-42, 1-1-43, 1-1-46, 1-1-47 1-1-48, 1-1-52, 1-1-53, 1-1-55, 1-1-64, 1-1-66, 1-1-107, 1-1-114, 1 -1-192, 1-1-274, 1-1-275, 1-1-296, 1-1-297, 1-1-299. Example # 16

Spodoptera fruqiperda test (spray treatment) Solvent: 78.0 parts by weight of acetone

1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylpolyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Maize leaf discs (Zea mays) are sprayed with an active substance preparation of the desired concentration and then dried, infested with beet caterpillars (Spodoptera frugiperda).

After the desired time, the effect is determined in%. In this case, 100% means that all caterpillars were killed; 0% means that no caterpillar has been killed.

In this test, for example, the following compounds of the preparation examples show> 80% efficacy with an application amount of 100 g / ha:

Example No. 1-1-217, 1-1-218, 1-1-219, 1-1-220, 1-1-221, 1-1-222, 1-1-223, 1-1-224 1-1-38, 1-1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1 -1-49, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1 -57, 1-1-58, 1-1-59, 1-1-60, 1-1- 61, 1-1-62, 1-1-63, 1-1-64, 1-1-65 , 1-1-66, 1-1-68, 1-1-69, 1-1-70, 1-1-71, 1-1-72, I-1-73, 1-1-74, 1 -1-75, 1-1-76, 1-1-77, 1-1-78, 1-1-79, 1-1-80, 1-1-81, 1-1-82, 1-1 -83, 1-1-84, 1-1-85, 1-1-86, 1-1-87, 1-1-92, 1-1-93, 1-1-97, 1-1-99 1-1-100, 1-1-101, I-1-102, 1-1-103, 1-1-113, 1-1-116, 1-1-117, 1-1-118, 1 -1-119, 1-1-120, 1-1-121, I-1-125, 1-1-126, 1-1-127, 1-1-128, 1-1-129, 1-1 -130, 1-1-131, 1-1-134, 1-1-135, 1-1-136, 1-1-137, 1-1-138, 1-1-139, 1-1-140 , 1-1-141, 1-1-142, 1-1-144, 1-1-145, I-1-146, 1-1-147, 1-1-148, 1-1-149, 1 -1-150, 1-1-151, 1-1-152, 1-1-153, 1-1-154, I-1-155, 1-1-156, 1-1-157, 1-1 -158, 1-1-160, 1-1-161, 1-1-163, 1-1-165, 1-1-166, I-1-167, 1-1-168, 1-3-1 , 1-1-169, 1-1-170, 1-1-171, 1-1-172, 1-1-173, 1-1-174, 1-1- 175, 1-1-176, 1-1-177, 1-1-178, 1-1-179, 1-1-180, 1-1-181, 1-1-182, 1-1-183, 1-1- 184, 1-1-185, 1-1-186, 1-1-187, 1-1-188, 1-1-189, 1-1-190, 1-1-191, 1- 1-192, 1-1-193, 1-1-195, 1-1-196, 1-1-199, 1-1-200, 1-1-201, 1-1-202, 1-1- 203, 1-1-204, 1-1-205, 1-1-206, 1-1-207, 1-1-208, 1-1-209, 1-1-210, 1-1-211, 1-1-212, 1-1-213, 1-1-214, 1-1-215, 1-1-216, 1-1-225, 1-1-226, 1-1-227, 1- 1-228, 1-1-231, 1-1-233, 1-1-234, 1-1-235, 1-1-237, 1-1-238, 1-1-239, 1-1- 240, 1-1-241, 1-1-242, 1-1-243, 1-1-244, 1-1-245, 1-1-246, 1-1-247, 1-1-248, 1-1-249, 1-1-250, 1-1-251, 1-1-252, 1-1-253, 1-1-255, 1-1-257, 1-1-258, 1- 1-259, 1-1-260, 1-1-261, 1-1-262, 1-1-263, 1-1- 264, 1-1-266, 1-1-267, 1-1- 268, 1-1-269, 1-1-270, 1-1-271, 1-1-272, 1-1-273, 1-1-274, 1-1-275, 1-1-276, 1-1-277, 1-1-279, 1-1-282, 1-1-283, 1-1-284, 1-1-285, 1-1- 286, 1-1-287, 1- 1-289, β-2-8, 1-2-12, 1-2-17, 1-2-19, 1-1-290, 1-1-291, 1-1-292, 1-293, 1-1-294, 1-1-295, 1-1-296, 1-1-297, 1-1-298, 1-1-299, 1-1-300, 1-1-301, 1- 302, 1-1-303 , 1-1-304, 1-1-305, 1-1-307, 1-1-308, 1-1-309, 1-1-310, 1-1-311, 1-312, 1-1 -313, 1-1-314, 1-1-315, 1-1-318, 1-1-324, 1-1-326, 1-1-327, 1-1-328, 1-329, 1 -1-330, 1-1-331, 1-1-332, 1-1-333, 1-1-334, 1-1-335, 1-1-336, 1-1-337, 1-338 , 1-1-339.1-1 -341, 1-1 -343, 1-1 -344, 1-1 -346, 1-1 -347, 1-1 -348, 1-1 -349, 1 -1-350, 1-1-351, 1-1-352, 1-1-353, 1-1-354, 1-1-355, Ι-2-2, Ι-2-3.

Example η ° 17

Myzus Test (Spray Treatment)

Solvent: 78.0 parts by weight of acetone

1.5 parts by weight of dimethylformamide

Emulsifier: 0,5 part by weight of alkylaryl polyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.

Chinese cabbage leaf (Brassica pekinensis) discs, which are infested by all stages of the peach green aphid (Myzus persicaé), are sprayed with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100% means that all aphids have been killed; 0% means that the aphids were not killed.

In this test, for example, the following compounds of the preparation examples show an effect of> 80% with an application amount of 100 g / ha:

Example 1-1-64, 1-1-68, 1-1-74, 1-1-75, 1-1-76, 1-1-77, 1-1-78, 1-1-80 , 1-1-81, 1-1-83, 1-1-84, 1-1-92, 1-1-97, 1-1-99, 1-1-100, 1-1-101, 1 -1-113, 1-1-116, 1-1-117, 1-1-118, 1-1-120, 1-1-121, 1-1-126, 1-1-127, 1-1 -128, 1-1-130, 1-1-131, 1-1-134, 1-135, 1-1-36, 1-1-137, 1-1-138, 1-1-139 1-1-142, 1-1-144, 1-1-145, 1-1-146, 1-1-150, 1-1-152, 1-1-163, 1-1-174, 1 -1-176, 1-1-177, 1-1-178, 1-1-179, 1-1-180, 1-1-188, 1-1-185, 1-1-186, 1-1 -198, 1-1-203, 1-1-207, 1-1-209, 1-1-211, 1-1-212, 1-1-216, 1-1-272, 1-2-10 1-1-308, 1-1-326, 1-1-327, 1-1-329, 1-1-330, 1-1-331, 1-1-331, 1-1-333, 1 -1-336, 1-1-338, 1-1-339, 1-1-354.

Example # 18

Aphis qossypii test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable active substance preparation, 1 part by weight of active substance is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. If it is necessary to add ammonium salts, penetration enhancers or ammonium salts and penetration enhancers, these are added by pipetting at a concentration of 1000 ppm after dilution in each case to the prepared preparation solution.

Cotton leaves (Gossypium hirsutum), which are heavily infested by the cotton aphid (Aphis gossypii), are sprayed with an active substance preparation of the desired concentration.

After the desired time, the effect is determined in%. In this case, 100% means that all aphids have been killed; 0% means that the aphids were not killed.

In this test, for example, the following compounds of the preparation examples show an effect of> 80% with an application amount of 100 g / ha:

example 1-1-68, 1-1-75, 1-1-76, 1-1-88, 1-1-98, 1-1-99, 1-1-104, 1-1-108 , 1-1-113, 1-1-131, 1-1-139, 1-1-143, 1-1-176, 1-1-251.

Claims (13)

1. Compounds of formula (I) (wherein formula R1 represents hydrogen, amino, hydroxy or C1-Ceralkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3- C6-cycloalkyl in each case optionally substituted one or more times, the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, (C1 -C4 alkoxy) carbonyl, C1 -C4 alkylamino, di (C1 -C4 alkyl) amino, C3 -C6 cycloalkylamino or (C1 -C4 alkyl) C3 -C6 cycloalkylamino, R2 represents hydrogen, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C6 cycloalkyl, C1 -C4 alkoxy, C1 -C4 alkylamino, di (C1 -C4 alkyl) amino, C3 -C6 C 2 -C 6 cycloalkylamino, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 alkylcarbonyl, R 3 represents hydrogen or C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 cycloalkyl, C 3 -C 12 cycloalkyl C1 -C6 alkyl and C4 -C 12-bicycloalkyl, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, amino, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylamino, C1-C4-alkoxy C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfinino, C 1 -C 4 alkylsulfinino-C 1 -C 4 alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 4 alkylsulfinyl C 1 -C 6 alkylsulfoximine-C 1 -C 6 alkyl, C 1 -C 6 alkylsulfoximino C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkylcarbonyl, C 3 -C 6-trialkylsilyl or a 5 or 6 membered heteroaromatic ring, R 2 and R 3 together may be attached through two to six carbon atoms and form a ring, which may further contain another nitrogen, sulfur or oxygen atom and which may be substituted one to four times with C1 -C2 alkyl, halogen, cyano. , amino or C1-C2-alkoxy or R2 and R3 together represent = S (C1-C4-alkyl) 2, = S (0) ( C 1 -C 4 alkyl) 2, R 4 represents hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1- C4-alkoxy, C1-C4-haloalkoxy, SF5, C1-C4-alkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino di- (C1-C4-alkyl) amino, C3-C6-cycloalkylamino, (C1-C4-alkoxy) imino, (C1-C4-alkyl) (C1-C4-alkoxy) imino, (C1-C4-haloalkyl) ( C1-C4-alkoxy) imino or C3-C6-trialkylsilyl or two R4 through adjacent carbon atoms form a ring which represents - (CH2) 3-, - (CH2) 4-, - (CH2) 5- , - (CH = CH-J2-, -OCH2O-, -O (CH2) 2O-, -OCF2O-, - (CF2) 2O-, -O (CF2) 2O-, - (CH = CH-CH = N ) - or - (CH = CH- N = CH) - or two R4, through adjacent carbon atoms, form the following ring rings, which may be substituted one or more times, the same or different, wherein the independent substituents are one or more. others can be selected from hid rogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 C 6 halocycloalkyl, halogen, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio (C 1 -C 6 alkyl), C 1 -C 4 alkylsulfinyl (C 1 -C 6 (C6-alkyl), C1-C4-alkylsulfonyl (C1-C6-alkyl), C1-C4-alkylamino, di (C1-C4-alkyl) amino or C3-C6-cycloalkylamino, > formula see original document page 114 </formula> η represents O to 3, R5 represents C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C6 haloalkyl, C1 -C6 halocycloalkyl, C2 -C6 alkenyl, C2 -C6 -haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkyl, C1-C4-alkoxy, C1-Qrhaloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylthio, C1-C4-haloalkyl , C1-C4-haloalkylsulfonyl, halogen, cyano, nitro or C3-C6-trialkylsilyl, R6 represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6 -cycloalkoxy, C1-C6-haloalkyl, C2-C6-haloalkenyl or <formula> formula see original document page 114 </formula> R7 independently of each other represents hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, halogen, cyano, nitro, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, m represents 0 to 4, X represents N, CH, CF, CCI, CBr or Cl, A represents -CH2-, -CH2O-, -CH2OCH2-, -CH2S-, -CH2SCH2-, - CH2N (C1-C6-alkyl) -, -CH2N (C1-C6-alkyl) CH2-, -CH [CO2 (C1-C6-alkyl)] -, - CH (CN) -, -CH (C1-C6- alkyl) -, -C (di-C1-C6-alkyl) -, -CH2CH2- or -C = NO (C1-4 Ce-alkyl) -, Q represents a 5- or 6-membered heteroaromatic ring or a ring system 8-, 9- or 10-membered, heterobicyclic, aromatic ring wherein the ring or ring system is optionally substituted one or more times, the same or different and wherein the substituents independent of each other may be selected from hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 C 1 -C 8 alkoxy, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 C 6 -C 11 -aloalkyl, C 3 -C 6 halocyclone alkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylthio, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl, C1 -C4 alkylamino, di (C1 -C4 alkyl) amino, C3 -C6 cycloalkylamino, (C1 -C6 alkyl) carbonyl, (C1 -C6 alkyl) ) aminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, tri- (C 1 -C 4) alkylsilyl, (C 1 -C 4 alkyl) (C 1 -C 4 alkoxy) imino or Q represents a 5- or 6-membered heteroaromatic or heterocyclic ring or a heterocyclic, 8-, 9- or 10-membered aromatic ring, wherein the ring or ring system is optionally substituted one or more times, the same or different and wherein the substituents independent of each other may be selected from hydrogen, C1 -C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6 -Ilyoalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen , CN , CO2H, CO2NH2, NO2, OH, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylthio, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkyl, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 3 -C 6 cycloalkylamino, (C 1 -C 6 alkyl) carbonyl, (C 1 -C 6 alkoxy) carbonyl, (C 1 -C 6 alkyl) aminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl tri- (C 1 -C 2) alkylsilyl, (C 1 -C 4 alkyl) (C 1 -C 4 alkoxy) imino, or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring phenyl or the ring may optionally be substituted one or more times, the same or different with C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 C 1 -C 10 Alkyl, C 1 -C 6 haloalkyl, C2 -C6 haloalkenyl, C2 -C6 haloalkyl, C3 -C6 halocycloalkyl, halogen, CN1 NO2, OH, C1 -C4 alkoxy, C1 -C4 haloalkoxy, as well as their N-oxides and salts. Compounds of formula (I) according to claim 1, wherein R 1 represents hydrogen, amino, hydroxy or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl in each optionally substituted one or more times the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 - alkylsulfonyl, (C1 -C4 alkoxy) carbonyl, C1 -C4 alkylamino, di (C1 -C4 alkyl) amino, C3 -C6 cycloalkylamino or (C1 -C4 alkyl) C3 -C6 cycloalkylamino, R2 represents hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 3 -C 6 cycloalkylamino, C 2 C6-alkoxycarbonyl or C2-C6-alkylcarbonyl, R3 represents hydrogen or C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, in each case optionally substituted one or m sometimes the same or different, wherein the substituents independent of each other may be selected from halogen, cyano, nitro, hydroxy, C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1-4. C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkylsulfimino, C1-C4-alkylsulfimino, C1 -C4-alkyl, C1-C4-alkylsulfinino-C2-C5-alkylcarbonyl, C1 -C4-alkylsulfoximine, C1-C4 C 1 -C 4 alkylsulfoximino C 1 -C 4 alkyls C 1 -C 4 alkylsulfoximino C 2 -C 5 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl or C 3 -C 6 trialkylsilyl, R 4 represents hydrogen, halogen, cyano, nitro, C 1 C4-alkyl, C1-C4-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, SF5, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-4 C4-alkylsulfonyl, C1 -C4 -haloalkylthio, C1 -C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, di (C1-C6-cycloalkylamino, (C1-C4-alkoxy) imino, -alkyl) (C C 1 -C 4 alkoxy) imino, (C 1 -C 4 haloalkyl) (C 1 -C 4 alkoxy) imino or C 3 -C 6 trialkylsilyl or two R 4, through adjacent carbon atoms, form a ring representing - (CH 2) 3, - (CH2) 4-, - (CH2) 5-, - (CH = CH-) 2-, -OCH2O-, -O (CH2) 2O-, -OCF2O-, - (CF2) 2O-, -O ( CF2) 2 O-, - (CH = CH-CH = N) - or - (CH = CH-N = CH) -, η represents O to 3, R5 represents C1 -C6 alkyl, C3 -C6 cycloalkyl, C1 -C6-haloalkyl, C1-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylthio, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl, halogen, cyano, nitro or C3 -C6 trialkylsilyl, R6 represents hydrogen, C1 -C6 alkyl, C2 -alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl or <formula> formula see original document page 117 </formula> R7 represents hydrogen, CI -C6 alkyl, C3 -C6 cycloalkyl C1 -C6 haloalkyl, halogen, cyano, nitro, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio or C1 -C4 haloalkylthio, m represents O to 4. X represents N, CH, CF, CCI, CBr or Cl, A represents -CH 2 -, CH (CH) 3, C (CH 3) 2 or CH 2 CH 2, Q represents a 5- or 6-membered heteroaromatic ring-ring aromatic heterobicyclic ring system wherein the ring or ring system is optionally substituted one or more times, the same or different and wherein the substituents independent of each other may be selected from hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkyl, C3-C6-halocycloalkyl, halogen, CN, CO2H, CO2NH2, NO2, OH, CrC4-alkoxy, C1- -C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-ylalalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylamino, di- (C1-C4) alkyl) amino, C3 -C6 -cyclo alkylamino, (C1-C6-alkyl) carbonyl, (C1-C-alkoxy) carbonyl (C1-C6-alkyl) aminocarbonyl, di- (C1-C4-alkyl) aminocarbonyl, tri- (C1-C2) alkylsilyl, (C1 (C4-alkyl) (C1 -C4-alkoxy) imino, as well as their N-oxides and salts. 3. Compounds of formula (1-1) <formula> formula see original document page 118 </formula> wherein R1 represents hydrogen, R2 represents hydrogen, R3 represents C1-C4 alkyl (methyl, ethyl, n-propyl, isopropyl) , n-butyl, iso-butyl, sec-butyl or tert-butyl) or cyano-C1 -C3 alkyl (cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyano-n-propyl, 2-cyano-n- propyl, 3-cyano-n-propyl, 1-cyano-isopropyl, 2-cyano-isopropyl), R4 represents hydrogen, methyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, iodine or trifluoromethoxy, R5 represents methyl fluorine, chlorine, bromine or iodine, R7 represents fluorine, chlorine or bromine, X represents N, CCl or CH, A represents CH2 or CH (CH3), Q represents an aromatic heterocyclic ring optionally substituted one or more times from the Q- series. 37, Q-38, Q-39, Q-40, Q-58 and Q-59, as well as a five-membered Q-60 heterocyclic ring, wherein the substituents independent of each other may be selected from Cr C3- alkyl, C1-C3-haloal C 1 -C 2 alkoxy, halogen, cyano, hydroxy, nitro or C 1 -C 2 haloalkoxy, or wherein the substituents independent of each other may be selected from phenyl or a 5- or 6-membered heteroaromatic ring wherein phenyl or the ring may optionally be substituted one or more times, the same or different with C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 Haloalkyl, C3 -C6 halocycloalkyl, halogen, CN, NO2, C1 -C4 alkoxy, C1 -C4 haloalkoxy, as well as their N-oxides and salts. Pyrazolecarboxylic acid derivatives of formula (IV) wherein A, Q, R6 have the meaning mentioned in claims 1 to 2. Pyrazolecarboxylic acid esters of formula (VI) wherein A, Q and R 6 have the meaning mentioned in claims 1 to 2 and R represents C 1 -C 6 alkyl. Alcohols of formula (X) wherein A and R 6 have the meaning mentioned in claims 1 to 2 and R represents C 1 -C 6 alkyl. Use of compounds of formula (I) as defined in claims 1 to 2 for the control of animal parasites. A process for combating animal parasites, characterized in that compounds of formula (I) according to claims 1 to 2 act on animal parasites and / or phytopathogenic fungi and / or their habitat and / or seed. Process for the production of agrochemical compositions, characterized in that compounds of formula (I) as defined in claims 1 to 2 are mixed with diluents and / or surfactants. Use of compounds of formula (I) as defined in claims 1 to 2 for seed treatment. Use of compounds of formula (I) as defined in claims 1 to 2 for the treatment of transgenic plants. Use of compounds of formula (I) as defined in claims 1 to 2 for the treatment of seed of transgenic plants. Seed which has been treated with a compound of formula (I) as defined in claims 1 to 2.