WO2015071260A1 - Pesticides - Google Patents

Abstract

The present application relates to novel insecticidal compounds, to processes for their preparation, to r their use for controlling animal pests including arthropods and in particular insects.

Description

PESTICIDES

Introduction

[0001] The present invention describes novel pesticides, procedures for their production and manufacturing, and their use as active ingredients, especially as insecticides and parasiticides.

[0002] 2-Azolyl-l,l-diphenylpropan-l-ols have been described before in EP 0 158 448 A2, EP 1 940 64 A2, and WO 1986/002072A1 as pesticides.

[0003] Novel substituted 2-(lH-pyrazol-l-yl)-l,l-diphenylethanes substituted at the 4- position of 1H- pyrazol-l-yl were found having excellent insecticidal, acaricidal and/or parasicidal activity.

Sumary of the invention

[0004] The present invention provides novel insecticidally, acaricidally and/or parasiticidally active compounds of the formula (I)

wherein

A represents (Ci-C i)alkyl, (C3-C6)cycloalkyl, (Ci-C₄)haloalkyl or (C3- C6)halocycloalkyl, preferably methyl;

Pv¹ represents mono- or disubstituted 1-pyrazolyl (= N-pyrazolyl) wherein at least one substituent is at position 4 of the 1-pyrazolyl and wherein a substituent is independently selected from the group consisting of halo, cyano, (Ci-C i)alkyl, (C3-C6)cycloalkyl, (Ci-C i)alkoxy, (Ci-C4)haloalkyl, (C3-C6)halocycloalkyl, or (Ci-C i)haloalkoxy. n represents 0, 1, 2, 3, 4 or 5; preferably 1, 2 or 3;

R² represents independently, halo, (Ci-C i)alkyl, (Ci-C i)haloalkyl, (Ci-C i)alkoxy, (Ci-C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0- (Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0- (Ci-C₄)alkyl, or -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)haloalkyl; or - - two R at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6-membered carbocyclic or heterocyclic system; m represents 0, 1 , 2, 3, 4 or 5; preferably 0, 1 , 2 or 3, more preferably 1 or 2;

R represents independently, halo, (Ci-C i)alkyl, (Ci-C i)haloalkyl, (Ci-C i)alkoxy,

(Ci-C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0- (Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0- (Ci-C₄)alkyl, or -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)haloalkyl; or two R³ at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6-membered carbocyclic or heterocyclic system;

R⁴ represents hydrogen, hydroxyl, halo, (Ci-C₄)alkoxy, (Ci-C₄)haloalkoxy, 0-(C2-

Cs)acyl, or 0-(C2-Cs)haloacyl; and also salts, N-oxides and tautomeric forms of the compounds of the formula (I).

[0005] In one preferred embodiment, the compounds of formula (I) are characterized in that A represents (Ci-C₂)alkyl, preferably methyl.

[0006] In one preferred embodiment, the compounds of formula (I) are characterized in that

R represents k represents 1 or 2, and

R⁵ represents cyano, (Ci-C₄)alkyl, (Ci-C₄)haloalkyl, (Ci-C₄)alkoxy, (Ci- C₄)haloalkoxy or halo, preferably fluoro, chloro or cyano, more preferably fluoro or cyano, under the proviso that at least one substituent R⁵ is at position 4 of the 1 -pyrazolyl.

[0007] In one preferred embodiment, the compounds of formula (I) are characterized in that

R represents and represents cyano, (Ci-C i)alkyl, (Ci-C4)haloalkyl, (Ci-C i)alkoxy, (Ci- C4)haloalkoxy or halo, preferably fluoro, chloro or cyano, more preferably fluoro or cyano. [0008] In one preferred embodiment, the compounds of formula (I) are characterized in that R represents methyl, (Ci-C3)haloalkyl, (Ci)haloalkoxy, (Ci)halothioalkyl, fluoro or chloro; or two R² at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted, preferably fluorosubstituted, 5-membered heterocycle comprising two hetero atoms selected from the group consisting of N or O, preferably O. [0009] In one preferred embodiment, the compounds of formula (I) are characterized in that R³ represents methyl, halomethyl, (Ci)haloalkoxy or halo such as fluoro or chloro.

[0010] In one preferred embodiment, the compounds of formula (I) are characterized in that a compound of formula (I) is a compound of formula (la)

wherein R², R³, R⁵, are as defined herein and n is 1 , 2, or 3 and m is 1 , 2 or 3, preferably wherein R⁵ cyano, chloro or fluoro, more preferably cyano or fluoro.

[001 1 ] In one preferred embodiment, the compounds of formula (I) are characterized in that compound of formula (I) is a compound of formula (lb)

- - wherein R², R³, R⁵, n, and m are as defined herein, preferably wherein R⁵ is cyano, chloro or fluoro, more preferably cyano or fluoro; and A represents (Ci-C i)alkyl.

[0012] In one preferred embodiment, the compounds of formula (I) are characterized in that a compound of formula (I) is a compound of formula (lc) or the enantiomer of a compound of formula (lc) or a mixture of both enantiomers,

wherein A, R², R³, R⁵, n, and m are as defined herein preferably wherein R⁵ is cyano, chloro or fluoro and A is methyl.

[0013] Another aspect of the present invention refers to a composition characterized in that it comprises at least one compound of the formula (I) as described herein and customary extenders and/or surfactants.

[0014] Another aspect of the present invention refers to a method for controlling insectic pests, characterized in that a compound of the formula (I) as described herein or a composition as described herein is allowed to act on the pests and/or their habitat.

[0015] Another aspect of the present invention refers to a use of compounds of the formula (I) as described herein or of compositions as described herein for controlling insects.

[0016] Another aspect of the present invention refers to a method for producing a compound (lc) as described herein characterized by reacting a compound of formula

with a compound of formula (V)

resulting in a compound of formula (lb)

wherein R², R³, R⁵, n, and m are as defined herein, preferably wherein R⁵ is cyano, chloro or fluoro, more preferably cyano or fluoro; and A represents (Ci-C i)alkyl. [0017] Another aspect of the present invention refers to a compound according to formula (V)

wherein R³, R⁵ and m are as defined herein.

Definitions [0018] The person skilled in the art is aware that the terms "a" or "an", as used in the present application, may, depending on the situation, mean "one (1)" "one (1) or more" or "at least one (1)".

[0019] Isomers: Depending on the nature of the substituents, the compounds of the formula (I) may be in the form of geometric and/or optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers.

[0020] Halogen, unless defined otherwise: elements of the 7th main group, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine and even more preferably fluorine and chlorine. Halo: halogen radicals, e.g. fluoro, chloro, bromo, iodo. - -

[0021 ] Alkyl, unless defined otherwise: saturated straight-chain or branched hydrocarbon radicals having preferably (C1-C4)-, (C1-C3)- or (Ci-C2)-carbon atoms. Examples: methyl [=(Ci)alkyl], ethyl [=(C₂)alkyl], propyl [=(C₃)alkyl], 1 -methylethyl [=(C₃)alkyl], butyl [=(C₄)alkyl], etc.

[0022] Cycloalkyl, unless defined otherwise: cyclic hydrogenalkyl radicals having preferably (C3-C6)-, or (C3)-carbon atoms. Examples: cyclopropyl, cyclopentyl, cyclobutyl, cyclohexyl. Cycloalkyl as defined herein may comprise an -CH2- linker (which can optionally be substituted by one or two halo) which connects the cyclic alkyl with the basic structure. Examples: Methylcyclopropyl [=methyl- (C3)cycloalkyl].

[0023] Alkoxy (alkyl radical -0-), unless defined otherwise: an alkyl radical which is attached via an oxygen atom (-0-) to the basic structure. For example, methoxy refers to (Ci)-alkoxy, i.e. CH3-O-. Alkoxy is preferably (C1-C4), (C1-C3) or (Ci-C2)alkoxy. Examples: methoxy, ethoxy, propoxy, 1 - methylethoxy, etc.

[0024] Thioalkyl, unless defined otherwise: an alkyl radical which is attached via -S- to the basic structure. For example, thiomethyl refers to (Ci)thioalkyl, i.e. CH3-S-. Thioalkylthio is preferably (Ci- C₄), (C1-C3) or (Ci-C₂)thioalkyl.

[0025] Acyl, unless defined otherwise: a -C(=0)H group (formyl) or an alkyl radical which is attached via a -C(=0)- group to the basic structure. For example, (Ci)-acyl refers to CH3-C(=0)-, (Co)-acyl refers to -C(=0)H. Acyl is preferably formyl, (C1-C4), (C1-C3) or (Ci-C₂)Ac l. Examples: CH₃C(=0)-, C₂H₅C(=0)-. [0026] Hetero atom: for example N, O, S, P, B, Si.

[0027] Carbocyclic system, unless defined otherwise: an optionally halosubstituted monocyclic 5 or 6- membered carbon system of which two positions, preferably two adjacent positions, are also part of a phenyl moiety. Thus, said system consists of an alkyl- or alkenyl-bridge (e.g., -(0¾)_ζ-, wherein z represents 1 to 4) that connects two positions, preferably two adjacent positions, which are also part of a phenyl moiety of a compound of formula (I) or any sub-structure derived thereof or intermediate for the production thereof, with each other. Such a system can form an aromatic system, as well. For example a carbocyclic system forms together with a phenyl moiety an indanyl moiety or a indenyl moiety or a dihydronaphtyl moiety or a naphtyl moiety. A carbocyclic system according to the invention can be substituted by at least one halogen, Ci-C₂-alkyl, Ci-C₂-haloalkyl (e.g., halogenated carbocyclic system, i.e. at least one C-H is replaced by one C-halo).

[0028] Heterocyclic system, unless defined otherwise: an optionally halosubstituted 5 or 6-membered heterocyclyl system or heteroaryl system of which two positions, preferably two adjacent positions, are also part of a phenyl moiety. In other words, a heterocyclic system comprises at least 2 carbon atoms (which are also part of a phenyl moiety of a compound of formula (I) or any sub-structure derived thereof or intermediate for the production thereof) and a bridge of at least one heteroatom preferably selected from the group consisting of N, S and O, and optionally carbon atoms (e.g., -CH2-O-CH2- or - N=CH-NH-). Such a system can form an aromatic system, as well. A heterocyclic system can be substituted by at least one halogen, Ci-C₂-alkyl, Ci-C₂-haloalkyl (e.g., halogenated heterocyclic system, i.e. at least one C-H is replaced by one C-Halo).

[0029] Heterocyclyl system, unless defined otherwise: an optionally halosubstituted monocyclic, non- aromatic 5 or 6-membered ring system of carbon atoms and 1 , 2 or 3 hetero atom preferably selected from the group consisting of N, O and S. [0030] Heteroaryl system, unless defined otherwise: an optionally halosubstituted aromatic monocyclic 5- or 6-membered heterocyclic ring system of carbon atoms and at least one heteroatom preferably selected from the group consisting of N, O and S. Examples: furan, thiophene, pyrrole, oxazole, isoxazolthiazole, 1,2,3-oxadiazole, pyridine, pyran, oxazine, thiazine, thiine, pyridazine.

[0031] Haloalkyl, halocycloalkyl, halothioalkyl, haloalkoxy, or haloacyl unless defined otherwise: an alkyl, cycloalkyl, thioalkyl, alkoxy or acyl wherein at least one C-H is replaced by a C-halo. In one embodiment, all C-H of one of said groups is replaced by C-Halo (perhalogenated). Examples: fluoromethyl, diflouromethyl, trifluoromethyl, fluoroethyl, digluoroethyl, trifluoromethyl, pentafluoroethyl, fluoromethoxy, fluorothiomethyl etc.

[0032] In the following, embodiments of the present application are described. The skilled person is aware that these embodiments can be combined. Not included are combinations which are against natural laws and which the person skilled in the art would therefore exclude based on his/her expert knowledge.

Description of the invention

[0033] It is obvious to the person skilled in the art that all embodiments can be present alone or in combination.

[0034] Depending on the nature of the substituents, the compounds of the formula (I), the formula (II) and the formula (A) may, if appropriate, be present as salts, tautomers, geometrical and/or optically active isomers or corresponding isomer mixtures of varying compositions.

[0035] If appropriate, the compounds according to the invention can be present in various polymorphic forms or as mixture of various polymorphic forms. The invention provides both the pure polymorphs and the polymorph mixtures, and both can be used in accordance with the invention.

[0036] Embodiments of the compounds of the formula (I) are described in more detail below: [0037] Compounds of formula (I)

wherein

A represents (Ci-C i)alkyl, (C3-C6)cycloalkyl, (Ci-C i)haloalkyl or (C3-C6)halocycloalkyl;

R¹ represents mono- or disubstituted 1 -pyrazolyl wherein at least one substituent is at position 4 of the 1 -pyrazolyl and wherein a substituent is independently selected from the group consisting of halo, cyano, (Ci-C i)alkyl, (C3-C6)cycloalkyl, (Ci-C i)alkoxy, (Ci-C₄)haloalkyl (C3- C6)halocycloalkyl, or (Ci-C i)haloalkoxy; n represents 0, 1 , 2, 3, 4 or 5; preferably 1 , 2 or 3;

R² represents independently halo, (Ci-C i)alkyl, (Ci-C₄)haloalkyl, (Ci-C₄)alkoxy, (Ci- C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0- (Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)alkyl, or -(Ci-C₄)haloalkyl-C(0)0-(Ci- C₄)haloalkyl; or two R² at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6-membered carbocyclic or heterocyclic system; m represents 0, 1 , 2, 3, 4 or 5; preferably 0, 1 , 2 or 3, more preferably 1 or 2;

R³ represents independently halo, (Ci-C4)alkyl, (Ci-C4)haloalkyl, (Ci-C4)alkoxy, (Ci- C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0- (Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)alkyl, or -(Ci-C₄)haloalkyl-C(0)0-(Ci- C₄)haloalkyl; or two R³ at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6-membered carbocyclic or heterocyclic system; - -

R represents hydroxyl, halo, (Ci-C4)alkyl, (Ci-C4)haloalkyl, (Ci-C4)alkoxy, (Ci-C4)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, 0-(C₂-C₅)acyl, or 0-(C₂-C₅)haloacyl; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).

[0038] One preferred embodiment refers to compounds of formula (I) wherein A represents (Ci- C4)alkyl, more preferably (Ci-C₂)alkyl, even more preferably methyl.

[0039] Another preferred embodiment refers to compounds of formula (I) wherein

R¹ represents ^* , and wherein k represents 1 or 2, and R⁵ represents independently from each other cyano, (Ci-C4)alkyl, (Ci- C4)haloalkyl, (Ci-C4)alkoxy, (Ci-C4)haloalkoxy or halo, under the proviso that at least one substituent R⁵ is at position 4 of the 1 -pyrazolyl. More preferably, R⁵ represents independently from each other cyano, methyl, halomethyl such as trifluoromethyl or trichloromethyl, methoxy, halomethoxy such as trifluoromethoxy or trichloromethoxy, fluoro or chloro under the proviso that at least one substituent R⁵ is at position 4 of the 1 -pyrazolyl. Most preferably, R⁵ at position 4 of the 1 -pyrazolyl is fluoro or cyano.

[0040] One more preferred embodiment refers to compounds of formula (I) wherein R¹ represents

, and R⁵ represents (Ci-C4)alkyl, (Ci-C4)alkoxy, cyano, or halo, preferably (Ci-C2)alkyl, (Ci- C2)alkoxy, cyano, or halo, more preferably methyl, methoxy, cyano or halo such as fluoro, chloro or bromo, even more preferably cyano or fluoro, most preferably fluoro.

[0041 ] One more preferred embodiment refers to compounds of formula (I) wherein R⁵ represents fluoro.

[0042] Another preferred embodiment refers to compounds of formula (I) wherein R⁴ represents -OH, - 0-(Ci-C₄)acyl or -0-(Ci-C₄)haloacyl, preferably -OH.

[0043] Yet another preferred embodiment refers to compounds of formula (I) wherein n represents 0, 1 , 2, or 3, preferably 1 , 2 or 3.

[0044] Yet another preferred embodiment refers to compounds of formula (I) wherein n represents 1 , 2, or 3 and at least one R² is at position 4 (para) of the phenylmoiety of the basic structure. - -

[0045] Another preferred embodiment refers to compounds of formula (I) wherein R represents independently from each other (Ci-C i)alkyl, (Ci-C i)haloalkyl, (Ci-C i)alkoxy, (Ci-C4)haloalkoxy, (Ci- C₄)thioalkyl, (Ci-C₄)halothioalkyl, (Ci-C₄)haloalkyl-phenyl (e.g. -CF₂-Ph), or halo; or two R² at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted 5-membered heterocycle comprising one or two hetero atoms selected from the group consisting of N, O or S. More preferably, R² represents (Ci-C2)alkyl, (Ci- C3)haloalkyl, (Ci-C3)haloalkoxy, (Ci-C3)halothioalkyl (Ci-C₂)haloalkyl-phenyl, fluoro, chloro, bromo, or iodo; or two R² at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted 5-membered heterocycles comprising two hetero atoms selected from the group consisting of N, O or S. Even more preferably, R² represents methyl, (Ci-C3)haloalkyl such as (Ci-C3)fluoroalkyl (e.g., trifluoromethyl, tetrafluoroethyl or heptafluoropropyl), (Ci)haloalkoxy such as (Ci)fluoroalkoxy (e.g. difluoromethoxy or trifluoromethoxy), (Ci)halothioalkyl such as (Ci)fluorothioalkyl (e.g., trifluorothiomethyl), fluoro or chloro or two R² at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted 5-membered heterocycle comprising two hetero atoms selected from the group consisting of N or O, preferably O (e.g., two R² represent a -O- CF2-O- moiety which is bound at position 4 and 3 to the phenyl-ring of the basic structure).

[0046] Yet another preferred embodiment refers to compounds of formula (I) wherein m represents 1 , 2, or 3, more preferably 1 or 2, even more preferably 1. [0047] Yet another preferred embodiment refers to compounds of formula (I) wherein m represents 1 , 2, or 3, more preferably 1 or 2, even more preferably 1 , and at least one R³ is at position 4 (para) of the phenylmoiety of the basic structure.

[0048] Another preferred embodiment refers to compounds of formula (I) wherein R³ represents independetly from each other (Ci-C4)alkyl, (Ci-C4)haloalkyl, (Ci-C i)alkoxy, (Ci-C i)haloalkoxy, (Ci- C i)thioalkyl, (Ci-C4)halothioalkyl, (Ci-C₂)haloalkyl-phenyl, or halo; or two R³ at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted 5-membered heterocycles comprising one or two hetero atoms selected from the group consisting of N, O or S. More preferably, R³ represents (Ci-C2)alkyl, (Ci-C3)haloalkyl, (Ci- C3)haloalkoxy, fluoro, chloro, bromo or iodo. Even more preferably, R³ represents methyl, halomethyl such as fluoromethyl (e.g., trifluoromethyl), (Ci)haloalkoxy such as (Ci)fluoroalkoxy (e.g. trifluoromethoxy) or halo such as fluoro.

[0049] In one preferred embodiment, halogenated groups such as halocarbocyclic systems, haloheterocyclic sytems, haloalkyl, halocycloalkyl, haloalkoxy and halothioalkyl are perhalogenated, preferably perfluorinated.

[0050] Another preferred embodiment refers to compounds of formula (la) - -

wherein R², R³, R⁵, are as defined herein, and n is 1 , 2 or 3 and m is 1 , 2 or 3, preferably wherein R⁵ is cyano or fluoro.

[0051 ] Another preferred embodiment refers to compounds of formula (lb)

wherein R², R³, R⁵, n, and m are as defined herein, preferably wherein R⁵ is cyano or fluoro; and A represents (Ci-C i)alkyl.

[0052] Another preferred embodiment refers to mixtures of comprising or consisting of compounds of formula (Ic) and (Ic')

wherein A, R², R³, R⁵, n, and m are as defined herein, preferably wherein R⁵ is cyano or fluoro and A is methyl.

Methods and uses

[0053] The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and/or their habitat. The control of the animal pests is preferably conducted in agriculture and forestry, and in material protection. Preferably excluded - - herefrom are methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods carried out on the human or animal body.

[0054] The invention furthermore relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents. [0055] In the context of the present application, the term "pesticide" in each case also always comprises the term "crop protection agent".

[0056] The compounds of the formula (I), having good plant tolerance, favourable homeotherm toxicity and good environmental compatibility, are suitable for protecting plants and plant organs against biotic and abiotic stressors, for increasing harvest yields, for improving the quality of the harvested material and for controlling animal pests, especially insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in aquatic cultures, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They can preferably be used as pesticides. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: pests from the phylum of the Arthropoda; from the class of the Chilopoda; from the order or the class of the Collembola; from the class of the Diplopoda; from the class of the Insecta, for example from the order of the Blattodea; from the order of the Coleoptera; from the order of the Diptera; from the order of the Hemiptera; from the suborder of the Heteroptera; from the order of the Hymenoptera; from the order of the Isopoda; from the order of the Isoptera; from the order of the Lepidoptera; from the order of the Orthoptera or Saltatoria; from the order of the Phthiraptera; from the order of the Psocoptera; from the order of the Siphonaptera; from the order of the Thysanoptera; from the order of the Zygentoma (= Thysanura); from the class of the Symphyla; pests from the phylum of the Mollusca, and also from the class of the Gastropoda; animal parasites from the phyla of the Plathelminthes and Nematoda; plant pests from the phylum of the Nematoda, i.e. phytoparasitic nematodes. [0057] Furthermore, it is possible to control, from the subkingdom of the Protozoa, the order of the Coccidia, for example Eimeria spp.

[0058] The compounds of the formula (I) can optionally, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds. - -

Formulations

[0059] The present invention further relates to formulations and use forms prepared therefrom as pesticides, for example drench, drip and spray liquors, comprising at least one compound of the formula (I). In some cases, the use forms comprise further pesticides and/or adjuvants which improve action, such as penetrants, e.g. vegetable oils, for example rapeseed oil, sunflower oil, mineral oils, for example paraffin oils, alkyl esters of vegetable fatty acids, for example rapeseed oil methyl ester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders, for example alkylsiloxanes and/or salts, for example organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate and/or retention promoters, for example dioctyl sulphosuccinate or hydroxypropyl guar polymers and/or humectants, for example glycerol and/or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0060] Customary formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and further possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations, in addition to one or more compounds of the formula (I), optionally comprise further agrochemically active compounds. [0061] These are preferably formulations or use forms which comprise auxiliaries, for example extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or further auxiliaries, for example adjuvants. An adjuvant in this context is a component which enhances the biological effect of the formulation, without the component itself having any biological effect. Examples of adjuvants are agents which promote retention, spreading, attachment to the leaf surface or penetration.

[0062] These formulations are prepared in a known way, for example by mixing the compounds of the formula (I) with auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or other auxiliaries such as, for example, surfactants. The formulations are prepared either in suitable facilities or else before or during application. [0063] The auxiliaries used may be substances suitable for imparting special properties, such as certain physical, technical and/or biological properties, to the formulation of the compounds of the formula (I), or to the use forms prepared from these formulations (for example ready-to-use pesticides such as spray liquors or seed dressing products). - -

[0064] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).

[0065] If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.

[0066] In principle, it is possible to use all suitable solvents. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, and also water.

[0067] In principle, it is possible to use all suitable carriers. Useful carriers include especially: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers can likewise be used. Useful carriers for granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

[0068] Liquified gaseous extenders or solvents can also be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellant gases, such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide. - 5 -

[0069] Examples of emulsifiers and/or foam- formers, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants, are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, hgnosulphite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the compounds of the formula (I) and/or one of the inert carriers is insoluble in water and when the application takes place in water.

[0070] It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc as further auxiliaries in the formulations and the use forms derived therefrom.

[0071] Additional components may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability. Foam formers or antifoams may also be present.

[0072] Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids may also be present as additional auxiliaries in the formulations and the use forms derived therefrom. Further possible auxiliaries are mineral and vegetable oils.

[0073] Optionally, further auxiliaries may be present in the formulations and the use forms derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreaders. In general, the compounds of the formula (I) can be combined with any solid or liquid additive commonly used for formulation purposes.

[0074] Useful retention promoters include all those substances which reduce the dynamic surface tension, for example dioctyl sulphosuccinate, or increase the viscoelasticity, for example hydroxypropylguar polymers.

[0075] Suitable penetrants in the present context are all those substances which are usually used for improving the penetration of agrochemical active compounds into plants. Penetrants are defined in this context by their ability to penetrate from the (generally aqueous) application liquor and/or from the - - spray coating into the cuticle of the plant and thereby increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, for example rapeseed oil methyl ester or soya oil methyl ester, fatty amine alkoxylates, for example tallowamine ethoxylate (15), or ammonium and/or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate.

[0076] The formulations preferably comprise between 0.00000001 and 98% by weight of the compound of the formula (I) or, with particular preference, between 0.01% and 95%> by weight of the compound of the formula (I), more preferably between 0.5%> and 90%> by weight of the compound of the formula (I), based on the weight of the formulation.

[0077] The content of the compound of the formula (I) in the use forms prepared from the formulations (in particular pesticides) may vary within wide ranges. The concentration of the compound of the formula (I) in the use forms is usually between 0.00000001 and 95%> by weight of the compound of the formula (I), preferably between 0.00001 and 1%> by weight, based on the weight of the use form. The compounds are employed in a customary manner appropriate for the use forms.

Mixtures

[0078] The compounds of the formula (I) may also be employed as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial species, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and/or plant growth regulators, in order thus, for example, to broaden the spectrum of action, to prolong the duration of action, to increase the rate of action, to prevent repulsion or prevent evolution of resistance. In addition, such active compound combinations may improve plant growth and/or tolerance to abiotic factors, for example high or low temperatures, to drought or to elevated water content or soil salinity. It is also possible to improve flowering and fruiting performance, optimize germination capacity and root development, facilitate harvesting and improve yields, influence maturation, improve the quality and/or the nutritional value of the harvested products, prolong storage life and/or improve the processability of the harvested products.

[0079] Furthermore, the compounds of the formula (I) can be present in a mixture with other active compounds or semiochemicals such as attractants and/or bird repellants and/or plant activators and/or growth regulators and/or fertilizers. Likewise, the compounds of the formula (I) can be used to improve plant properties such as, for example, growth, yield and quality of the harvested material.

[0080] In a particular embodiment according to the invention, the compounds of the formula (I) are present in formulations or the use forms prepared from these formulations in a mixture with further compounds, preferably those as described below. - 7 -

[0081] If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included even if not explicitly mentioned in each case.

Insecticides/acaricides/nematicides

[0082] The active compounds identified here by their common names are known and are described, for example, in the pesticide handbook ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or can be found on the Internet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S -methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion- methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel antagonists, such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.

(3) Sodium channel modulators / voltage-gated sodium channel blockers such as, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)- trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(lR)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)- isomer)], tralomethrin and transfluthrin or DDT or methoxychlor. - -

Nicotinergic acetylcholine receptor (nAChR) agonists, such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

Allosteric activators of the nicotinergic acetylcholine receptor (nAChR) such as, for example, spinosyns, e.g. spinetoram and spinosad.

Chloride channel activators, such as, for example, avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.

Juvenile hormone imitators such as, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

Active compounds with unknown or nonspecific mechanisms of action such as, for example, alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic.

Selective antifeedants, for example pymetrozine or flonicamid.

Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazin or etoxazole.

Microbial disruptors of the insect gut membrane, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl .

Oxidative phosphorylation inhibitors, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon;

Oxidative phosphorylation decouplers acting by interrupting the H proton gradient such as, for example, chlorfenapyr, DNOC and sulfluramid.

Nicotinergic acetylcholine receptor antagonists such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.

Chitin biosynthesis inhibitors, type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

Chitin biosynthesis inhibitors, type 1 , for example buprofezin.

Moulting inhibitors (in particular for Diptera, i.e. dipterans) such as, for example, cyromazine. - -

(18) Ecdysone receptor agonists such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists such as, for example, amitraz.

(20) Complex-Ill electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat.

(24) Complex-IV electron transport inhibitors such as, for example, phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.

(25) Complex II electron transport inhibitors, such as, for example, cyenopyrafen and cyflumetofen.

(28) Ryanodine receptor effectors, such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide, further active compounds such as, for example, afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim, flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and also the following compounds: 3-bromo-N- {2-bromo-4-chloro-6-[(l- cyclopropylethyl)carbamoyl]phenyl}-l -(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamide (known from WO2005/077934) and l- {2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl} -3- (trifluoromethyl)-lH-l,2,4-triazole-5-amine (known from WO2006/043635), {l'-[(2E)-3-(4- chlorophenyl)prop-2-en-l-yl]-5-fluorospiro[indol-3,4'-piperidin]-l(2H)-yl}(2-chloropyridin-4- yl)methanone (known from WO2003/106457), 2-chloro-N-[2- {l-[(2E)-3-(4-chlorophenyl)prop-2-en-l- yl]piperidin-4-yl} -4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494), 3-(2,5- dimethylphenyl)-4-hydroxy- 8 -methoxy- 1,8- diazaspiro [4.5] dec-3 - en-2- one (known from

WO2009/049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl- ethylcarbonate (known from WO2009/049851), 4-(but-2-yn-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5- fluoropyrimidine (known from WO2004/099160), 4-(but-2-yn-l -yloxy)-6-(3-chlorophenyl)pyrimidine - -

(known from WO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2), 4-[5-(3,5-dichlorophenyl)-5- (trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl-N- {2-oxo-2-[(2,2,2- trifluoroethyl)amino]ethyl}benzamide (known from WO2005/085216), 4- {5-[3-chloro-5- (trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl}-N- {2-oxo-2-[(2,2,2- trifluoroethyl)amino] ethyl} -1-naphthamide (known from WO2009/002809), methyl 2-[2-({[3-bromo-l- (3-chloropyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2- methylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[2-({[3-bromo-l-(3- chloropyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2- ethylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[2-({[3-bromo-l-(3-chloropyridin- 2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[3,5-dibromo-2-({[3-bromo-l-(3-chloropyridin-2-yl)-lH- pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from WO2005/085216), 1- (3 -chloropyridin-2-yl)-N- [4-cyano-2-methyl-6-(methylcarbamoyl)phenyl] -3 - { [5 -(trifluoromethyl)-2H- tetrazol-2-yl]methyl}-lH-pyrazole-5-carboxamide (known from WO2010/069502), N-[2-(5-amino- l,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5- carboxamide (known from CN102057925), 3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(l, 1,1,2,3,3,3- heptafluoropropan-2-yl)-2-methylphenyl]phthalamide (known from WO2012/034472), 8-chloro-N-[(2- chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imidazo[l,2-a]pyridine-2-carboxamide (known from WO2010/129500), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2- methyl-N-(l-oxidothietan-3-yl)benzamide (known from WO2009/080250), 4-[5-(3,5-dichlorophenyl)-5- (trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxidothietan-3-yl)benzamide (known from WO2012/029672), l-[(2-chloro-l,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[l,2- a]pyrimidin-l-ium-2-olate (known from WO2009/099929), l-[(6-chloropyridin-3-yl)methyl]-4-oxo-3- phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium-2-olate (known from WO2009/099929), (5S,8R)-l-[(6- chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-lH-5,8-epoxyimidazo[l,2-a]azepine (known from WO2010/069266), (2E)-l-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2- pentylidenehydrazinecarboximidamide (known from WO2010/060231), 4-(3- {2,6-dichloro-4-[(3,3- dichloroprop-2-en-l-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-l-(3-chloropyridin-2-yl)-3- (fluoromethoxy)-lH-pyrazole-5-carboxamide (known from WO2008/134969).

Fungicides

[0083] The active compounds specified herein by their common name are known and described, for example, in "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides).

(1) Inhibitors of ergosterol biosynthesis such as, for example, (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.1 1) dodemorph acetate, (1.12) epoxiconazole, - -

(1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50) triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole, (1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57) uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60) l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l -yl)cycloheptanol, (1.61) methyl l-(2,2-dimethyl-2,3-dihydro-lH-inden-l-yl)-lH-imidazole-5-carboxylate, (1.62) N'- {5- (difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N'- {2-methyl-5-(trifluoromethyl)-4-[3-

(trimethylsilyl)propoxy]phenyl}imidoformamide and (1 -64) 0-[l-(4-methoxyphenoxy)-3,3- dimethylbutan-2-yl] - 1 H-imidazole- 1 -carbothioate, (1.65) pyrisoxazole.

(2) Respiration inhibitors (respiratory chain inhibitors) such as, for example, (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9) furametpyr, (2.10) furmecyclox, (2.11) isopyrazam mixture of the syn-epimeric racemate 1RS,4SR,9RS and the anti-empimeric racemate 1RS,4SR,9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam (anti- epimeric enantiomer 1 S,4R,9R), (2.15) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1 S,4R,9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad, (2.22) sedaxane, (2.23) thifluzamide, (2.24) l-methyl-N-[2-(l ,l,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-lH- pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-l -methyl-N-[2-(l ,l,2,2-tetrafluoroethoxy)phenyl]- lH-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(l , 1,2,3,3, 3- hexafluoropropoxy)phenyl] - 1 -methyl- 1 H-pyrazole-4-carboxamide, (2.27) N- [ 1 -(2,4-dichlorophenyl)- 1 - methoxypropan-2-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.28) 5,8-difluoro-N- [2-(2-fluoro-4- {[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine, (2.29) benzovindiflupyr, (2.30) N-[(lS,4R)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4-methanonaphthalen- 5-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide and (2.31) N-[(lR,4S)-9- (dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3 -(difluoromethyl)- 1 -methyl- 1 H- pyrazole-4-carboxamide, (2.32) 3-(difluoromethyl)-l-methyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden- 4-yl)-lH-pyrazole-4-carboxamide, (2.33) l,3,5-trimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl)-lH-pyrazole-4-carboxamide, (2.34) l-methyl-3-(trifluoromethyl)-N-(l ,l,3-trimethyl-2,3-dihydro- lH-inden-4-yl)-lH-pyrazole-4-carboxamide, (2.35) l-methyl-3-(trifluoromethyl)-N-[(3R)-l,l,3- trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazole-4-carboxamide, (2.36) 1 -methyl-3 -(trifluoromethyl)- - -

N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (2.37) 3-

(difluoromethyl) - 1 -methyl-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazole-4- carboxamide, (2.38) 3-(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]- lH-pyrazole-4-carboxamide, (2.39) l,3,5-trimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl]-lH-pyrazole-4-carboxamide, (2.40) l,3,5-trimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden- 4-yl]-lH-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N-(l ,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl)pyridine-3-carboxamide, (2.43) isofetamid

(3) Respiration inhibitors (respiratory chain inhibitors) acting on complex III of the respiratory chain such as, for example, (3.1) ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.5) dimoxystrobin, (3.8) enestroburin, (3.9) famoxadone,

(3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20) pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23) (2E)-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2- (methoxyimino)-N-methylethanamide, (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2- { [( {(IE)- 1 - [3- (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide, (3.25) (2E)-2- (methoxyimino)-N-methyl-2- {2- [(E)-( { 1 - [3 -

(trifluoromethyl)phenyl] ethoxy } imino)methyl]phenyl} ethanamide, (3.26) (2E)-2- {2- [( { [( 1 E)- 1 -(3 - {[(E)-l-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)- N-methylethanamide, (3.27) (2E)-2- {2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2- ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.28) 2-chloro-N-(l ,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl)pyridine-3-carboxamide, (3.29) 5-methoxy-2-methyl-4-(2- {[({(lE)-l-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l,2,4- triazol-3-one, (3.30) methyl (2E)-2- {2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyprop-2-enoate, (3.31) N-(3-ethyl- 3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide, (3.32) 2- {2-[(2,5- dimethylphenoxy)methyl]phenyl} -2-methoxy-N-methylacetamide, (4) inhibitors of mitosis and cell division such as, for example, (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8) pencycuron, (4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7-(4- methylpiperidin-l-yl)-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo[l,5-a]pyrimidine and (4.14) 3-chloro-5- (6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds having multisite activity such as, for example, (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper preparations such as copper hydroxide, (5.6) copper naphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) copper sulphate, (5.10) dichlofluanid,

(5.11) dithianon, (5.12) dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) folpet, - -

(5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zinc metiram, (5.27) copper-oxine, (5.28) propamidine, (5.29) propineb, (5.30) sulphur and sulphur preparations such as, for example calcium polysulphide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram and (5.35) anilazine.

(6) Resistance inducers such as, for example, (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin.

(7) Inhibitors of amino acid and protein biosynthesis such as, for example, (7.1) , (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) pyrimethanil, (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline and (7.9) oxytetracycline and (7.10) streptomycin.

(8) ATP production inhibitors such as, for example, (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.

(9) Inhibitors of cell wall synthesis such as, for example, (9.1) benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) valifenalate and (9.10) polyoxin B.

(10) Inhibitors of lipid and membrane synthesis such as, for example, (10.1) biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb,, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene and (10.15) tolclofos-methyl.

(11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid, (11.2) diclocymet, (1 1.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon, (1 1.6) tricyclazole and (11.7) 2,2,2-trifluoroethyl {3- methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

(12) Inhibitors of nucleic acid synthesis such as, for example, (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8) hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14) octhilinone.

(13) Signal transduction inhibitors such as, for example, (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8) proquinazid.

(14) Decouplers such as, for example, (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap. - -

(15) Further compounds such as, for example, (15.1) benthiazole, (15.2) bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat, (15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid, (15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15) difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine, (15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21) fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl- sodium, (15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin, (15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35) nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38) oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40) phenothrin, (15.41) phosphoric acid and its salts, (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph, (15.45) (2E)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (15.46) (2Z)-3-(4-tert- butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50) tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid, (15.54) (3S,6S,7R,8R)-8-benzyl-3-[( {3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-yl 2-methylpropanoate, (15.55) l-(4- {4-[(5R)- 5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (15.56) l-(4- {4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro- l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l - yl]ethanone, (15.57) l-(4- {4-[5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2- yl} piperidin- 1 -yl)-2- [5-methyl-3 -(trifluoromethyl)- 1 H-pyrazol- 1 -yl] ethanone, (15.58) l-(4- methoxyphenoxy)-3,3-dimethylbutan-2-yl lH-imidazole-l-carboxylate, (15.59) 2,3,5, 6-tetrachloro-4- (methylsulphonyl)pyridine, (15.60) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61) 2,6- dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole-l,3,5,7(2H,6H)-tetrone, (15.62) 2-[5-methyl-3- (trifluoromethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5R)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2- yl}piperidin-l -yl)ethanone, (15.63) 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l -yl]-l-(4- {4-[(5S)-5- phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)ethanone, (15.64) 2-[5-methyl-3- (trifluoromethyl)- 1 H-pyrazol- 1 -yl]- 1 - {4- [4-(5-phenyl-4,5-dihydro- 1 ,2-oxazol-3 -yl)- 1 ,3-thiazol-2- yl]piperidin-l-yl} ethanone, (15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66) 2-chloro-5- [2-chloro-l-(2,6-difluoro-4-methoxyphenyl)-4-methyl-lH-imidazol-5-yl]pyridine, (15.67) 2- phenylphenol and salts, (15.68) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6- difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6- dimethylpyridazine, (15.72) 5-amino-l,3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N'-phenyl-N'-(prop-2- yn-l-yl)thiophene-2-sulphonohydrazide, (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76) 5-methyl-6- octyl[l,2,4]triazolo[l,5-a]pyrimidine-7-amine, (15.77) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78) N'-(4- {[3-(4-chlorobenzyl)-l,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N- - 5 - methylimidoformamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-l- yloxy)phenyl]propanamide, (15.80) N- [(4-chlorophenyl)(cyano)methyl] -3 - [3 -methoxy-4-(prop-2-yn- 1 - yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4- dichloronicotinamide, (15.82) N- [ 1 -(5-bromo-3 -chloropyridin-2-yl)ethyl] -2,4-dichloronicotinamide, (15.83) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (15.84) N- {(E)- [(cyclopropylmethoxy)imino] [6-(difluoromethoxy)-2,3 -difluorophenyl]methyl} -2-phenylacetamide, (15.85) N- {(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2- phenylacetamide, (15.86) N'- {4-[(3-tert-butyl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}- N-ethyl-N-methylimidoformamide, (15.87) N-methyl-2-(l- {[5-methyl-3-(trifluoromethyl)-lH-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N-( 1 ,2,3 ,4-tetrahydronaphthalen- 1 -yl)- 1 ,3 -thiazole-4-carboxamide, (15.88) N-methyl-2-( 1 - { [5-methyl-3 -(trifluoromethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [( 1 R)- 1 ,2,3,4- tetrahydronaphthalen- 1 -yl] - 1 ,3 -thiazole-4-carboxamide, (15.89) N-methyl-2-( 1 - { [5 -methyl-3 - (trifluoromethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [(1S)-1 ,2,3 ,4-tetrahydronaphthalen- 1 -yl] - l,3-thiazole-4-carboxamide, (15.90) pentyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl} carbamate, (15.91) phenazine- 1 -carboxylic acid, (15.92) quinolin-8-ol, (15.93) quinolin-8-ol sulphate (2: 1), (15.94) tert-butyl {6-[({[(l-methyl-lH- tetrazol-5-yl)(phenyl)methylene]amino} oxy)methyl]pyridin-2-yl}carbamate, (15.95) 1 -methyl-3- (trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (15.96) N-(4'- chlorobiphenyl-2-yl)-3-(difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide, (15.97) N-(2',4'- dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (15.98) 3- (difluoromethyl)-l-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (15.99) N-(2',5'-difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, (15.100) 3- (difluoromethyl)- 1 -methyl-N- [4'-(prop- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 H-pyrazole-4-carboxamide, (15.101) 5-fluoro-l,3-dimethyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (15.102) 2- chloro-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]nicotinamide, (15.103) 3-(difluoromethyl)-N-[4'-(3,3- dimethylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 -methyl- 1 H-pyrazole-4-carboxamide, (15.104) N- [4'-(3 ,3 - dimethylbut- 1 -yn- 1 -yl)biphenyl-2-yl] -5-fluoro- 1 ,3 -dimethyl- 1 H-pyrazole-4-carboxamide, (15.105) 3 - (difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-l -methyl- lH-pyrazole-4-carboxamide, (15.106) N-(4'- ethynylbiphenyl-2-yl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, (15.107) 2-chloro-N-(4'- ethynylbiphenyl-2-yl)nicotinamide, (15.108) 2-chloro-N- [4'-(3 ,3 -dimethylbut- 1 -yn- 1 -yl)biphenyl-2- yl]nicotinamide, (15.109) 4-(difluoromethyl)-2-methyl-N- [4'-(trifluoromethyl)biphenyl-2-yl] -1,3- thiazole-5-carboxamide, (15.110) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l,3- dimethyl-lH-pyrazole-4-carboxamide, (15.111) 2-chloro-N- [4'-(3-hydroxy-3 -methylbut- 1-yn-l- yl)biphenyl-2-yl]nicotinamide, (15.112) 3 -(difluoromethyl)-N- [4'-(3 -methoxy-3 -methylbut- 1 -yn- 1 - yl)biphenyl-2-yl]-l -methyl- lH-pyrazole-4-carboxamide, (15.113) 5-fluoro-N-[4'-(3-methoxy-3- methylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 ,3 -dimethyl- 1 H-pyrazole-4-carboxamide, (15.114) 2-chloro-N- [4'- (3 -methoxy-3 -methylbut- l-yn-l-yl)biphenyl-2-yl]nicotinamide, (15.115) (5-bromo-2-methoxy-4- methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (15.116) N-[2-(4- {[3-(4- - - chlorophenyl)prop-2-yn-l -yl]oxy} -3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide, (15.117)

4- oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118) but-3-yn-l-yl {6-[( {[(Z)-(l-methyl-lH-tetrazol-

5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.119) 4-amino-5- fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), (15.120) propyl 3,4,5- trihydroxybenzoate, (15.121) l,3-dimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazole- 4-carboxamide, (15.122) l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazole-4-carboxamide, (15.123) l,3-dimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]- lH-pyrazole-4-carboxamide, (15.124) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol- 4-yl](pyridin-3-yl)methanol, (15.125) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.126) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127) 2- {[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran- 2-yl]methyl} -2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.128) l- {[3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol-5-yl thiocyanate, (15.129) 5-(allylsulfanyl)- 1 - { [3 - (2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazole, (15.130) 2-[l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3 -thione, (15.131) 2- {[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difl

triazole-3 -thione, (15.132) 2- {[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.133) l- {[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol-5-yl thiocyanate, (15.134) 1 - { [rel(2R,3R)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (15.135) 5- (allylsulphanyl)- 1 - { [rel(2R,3 S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazole, (15.136) 5-(allylsulphanyl)-l - {[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazole, (15.137) 2-[(2S,4S,5S)-l-(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.138) 2-[(2R,4S,5S)-l- (2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.139) 2-[(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- l,2,4-triazole-3 -thione, (15.140) 2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.141) 2-[(2S,4S,5R)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3 -thione, (15.142) 2-[(2R,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (15.143) 2-[(2R,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.144) 2-[(2S,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (15.145) 2-fluoro-6-

(trifluoromethyl)-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)benzamide, (15.146) 2-(6- benzylpyridin-2-yl)quinazoline, (15.147) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2- yl]quinazoline, (15.148) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (15.149) abscisic acid, (15.150) 3-(difluoromethyl)-N-methoxy-l -methyl-N-[l -(2,4,6-trichlorophenyl)propan-2- yl]-lH-pyrazole-4-carboxamide, (15.151) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2-yloxy)-2- - 7 - methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (15.152) Ν'- {5-bromo-6-[l -(3,5- difluorophenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.153) N'- {5- bromo-6-[(lR)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamide, (15.154) N'- {5-bromo-6-[(lS)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin- 3-yl} -N-ethyl-N-methylimidoformamide, (15.155) N'- {5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.156) N'- {5-bromo-6-[(trans-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.157) N- cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l -methyl-lH-pyrazole-4-carboxamide, (15.158) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-l -methyl- lH-pyrazole-4- carboxamide, (15.159) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (15.160) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5- fluoro- 1 -methyl- 1 H-pyrazole-4-carboxamide, (15.161) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl- 3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3- (difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l -methyl-lH-pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l -methyl- lH-pyrazole-4- carboxamide, (15.164) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide, (15.165) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-l -methyl- lH-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, (15.167) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (15.168) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5- methylbenzyl)-l -methyl- lH-pyrazole-4-carboxamide, (15.169) N-cyclopropyl-N-(2-cyclopropyl-5- methylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (15.170) N-(2-tert- butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (15.171) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5- fluoro-1 -methyl- lH-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l - methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-lH-pyrazole-4-carboxamide, (15.173) N-[2-chloro-6- (trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (15.174) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-

(difluoromethyl)-5-fluoro-l -methyl- lH-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3- (difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro- 1 -methyl- 1 H-pyrazole-4-carboxamide, (15.176) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4- carbothioamide, (15.177) 3-(difluoromethyl)-N-(7-fluoro-l , 1 ,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-l - methyl- lH-pyrazole-4-carboxamide, (15.178) 3-(difluoromethyl)-N-[(3R)-7-fluoro-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-l -methyl-lH-pyrazole-4-carboxamide, (15.179) 3-(difluoromethyl)-N-[(3S)-7- fluoro- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-pyrazole-4-carboxamide, (15.180) N'- (2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (15.181) N'- {4-[(4,5-dichloro-l,3- thiazol-2-yl)oxy]-2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (15.182) N-(4-chloro-2,6- - - difluorophenyl)-4-(2-chloro-4-fluorophenyl)- 1 ,3-dimethyl- 1 H-pyrazole-5-amine. All mixing components mentioned in classes (1) to (15) can, if they are capable on the basis of their functional groups, optionally form salts with suitable bases or acids.

Biological pesticides as mixing components [0084] The compounds of the formula (I) can be combined with biological pesticides.

[0085] Biological pesticides comprise in particular bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

[0086] Biological pesticides comprise bacteria such as spore-forming bacteria, root-colonising bacteria and bacteria which act as biological insecticides, fungicides or nematicides. Safener as mixing components

[0087] The compounds of the formula (I) can be combined with safeners such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl)-l,3-oxazolidine (CAS 52836-31-4).

Plants and plant parts

[0088] All plants and plant parts can be treated in accordance with the invention. Here, plants are to be understood to mean all plants and plant parts such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soya bean, potato, sugar beet, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, oilseed rape, and also fruit plants (with the fruits apples, pears, citrus fruits and grapevines). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights. Plant parts should be understood to mean all parts and organs of the plants above and below ground, such as shoot, leaf, flower and root, examples given being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also tubers, roots and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. - -

Transgenic plant, seed treatment and integration events

[0089] The transgenic plants or plant cultivars (those obtained by genetic engineering) which are to be treated with preference in accordance with the invention include all plants which, through the genetic modification, received genetic material which imparts particular advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processability of the harvested products. Further and particularly emphasized examples of such properties are increased resistance of the plants against animal and microbial pests, such as against insects, arachnids, nematodes, mites, slugs and snails owing, for example, to toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and also combinations thereof), furthermore increased resistance of the plants against phytopathogenic fungi, bacteria and/or viruses.

Crop protection - types of treatment

[0090] The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seed, furthermore as a powder for dry seed treatment, a solution for liquid seed treatment, a water-soluble powder for slurry treatment, by incrusting, by coating with one or more coats, etc. It is furthermore possible to apply the compounds of the formula (I) by the ultra- low volume method or to inject the application form or the compound of the formula (I) itself into the soil.

Treatment of seed

[0091] The control of animal pests by treating the seed of plants has been known for a long time and is the subject of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with, or at least reduce considerably, the additional application of pesticides during storage, after sowing or after emergence of the plants. It is furthermore desirable to optimize the amount of active compound employed in such a way as to provide optimum protection for the seed and the germinating plant from attack by animal pests, but without damaging the plant itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic insecticidal or nematicidal properties of pest- - - resistant or -tolerant transgenic plants in order to achieve optimum protection of the seed and also the germinating plant with a minimum of pesticides being employed.

[0092] The present invention therefore in particular also relates to a method for the protection of seed and germinating plants, from attack by pests, by treating the seed with one of the compounds of the formula (I). The method according to the invention for protecting seed and germinating plants against attack by pests furthermore comprises a method where the seed is treated simultaneously in one operation or sequentially with a compound of the formula (I) and a mixing component. It also comprises a method where the seed is treated at different times with a compound of the formula (I) and a mixing component. [0093] The invention likewise relates to the use of the compounds of the formula (I) for the treatment of seed for protecting the seed and the resulting plant from animal pests.

Animal health

[0094] In the animal health field, i.e. in the field of veterinary medicine, the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasites includes in particular helminths and protozoans, such as coccidia. Ectoparasites are typically and preferably arthropods, in particular insects and acarids.

[0095] In the field of veterinary medicine the compounds of the formula (I) are suitable, with favourable homeotherm toxicity, for controlling parasites which occur in animal breeding and animal husbandry in livestock, breeding, zoo, laboratory, experimental and domestic animals. They are active against all or specific stages of development of the parasites.

[0096] Agricultural livestock include, for example, mammals, such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeers, fallow deers, and in particular cattle and pigs; or poultry such as turkeys, ducks, geese, and in particular chickens; fish and crustaceans, for example in aquaculture; and also insects such as bees. [0097] Domestic animals include, for example, mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and in particular dogs, cats, cage birds, reptiles, amphibians and aquarium fish.

[0098] According to a preferred embodiment, the compounds of the formula (I) are administered to mammals.

[0099] According to another preferred embodiment, the compounds of the formula (I) are administered to birds, namely cage birds and in particular poultry. - -

[0100] By using the compounds of the formula (I) to control animal parasites, it is intended to reduce or prevent illness, cases of deaths and performance reductions (in the case of meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible and better animal well-being is achievable. [0101 ] The term "control" or "controlling" as used herein with regard to the animal health field, means that the compounds of the formula (I) are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels. More specifically, "controlling", as used herein, means that the compound of the formula (I) is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation. Arthropods include: from the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; from the order of the Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; from the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; from the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; as well as nuisance and hygiene pests from the order of the Blattarida. Arthropods furthermore include: from the subclass of the Acari (Acarina) and the order of the Metastigmata, for example from the family of argasidae like Argas spp., Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order of mesostigmata like Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp., Acarapis spp.; from the order of the Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; and from the order of the Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., - -

Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Parasitic Protozoa include:

Mastigophora (Flagellata) such as, for example, Trypanosomatidae, for example, Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as, for example, Trichomonadidae, for example, Giardia lamblia, G. canis.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example, Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp., Harmanella sp. Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis,

E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans,

E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec, Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec, I. suis, Cystisospora spec, Cryptosporidium spec, in particular C. parvum; such as

Toxoplasmadidae, for example, Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example, Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, such as Leucozoidae, for example,

Leucozytozoon simondi, such as Plasmodiidae, for example, Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, such as Piroplasmea, for example, Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, such as Adeleina, for example, Hepatozoon canis, H. spec.

Pathogenic endoparasites, which are helminths, include Platyhelmintha (e.g. Monogenea, cestodes and trematodes), nematodes, Acanthocephala, and Pentastoma. Further helminths include:

Monogenea: e.g.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.

Cestodes: from the order of the Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.

From the order of the Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., - -

Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.

Trematodes: from the class of the Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.

Nematodes: Trichinellida for example: Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp.

From the order of the Tylenchida for example: Micronema spp., Strongyloides spp. From the order of the Rhabditina for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp. From the order of the Spirurida, for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp.

Acanthocephala: from the order of the Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp.; from the order of the Polymorphida, for example: Filicollis spp.; from the order of the Moniliformida, for example: Moniliformis spp. - -

From the order of the Echinorhynchida, for example, Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of the Porocephalida, for example, Linguatula spp.

In the veterinary field and in animal keeping, administration of the compounds of the formula (I) is carried out by methods generally known in the art, such as enterally, parenterally, dermally or nasally in the form of suitable preparations. Administration can be carried out prophylactically or therapeutically.

Thus, one embodiment of the present invention refers to the use of a compound of the formula (I) as medicament.

A further aspect refers to the use of a compound of the formula (I) as an antiendoparasitic agent, in particular a helminthicidal agent or antiprotozoic agent. Compounds of the formula (I) are suitable for use as an antiendoparasitic agent, in particular a helminthicidal agent or antiprotozoic agent, for example in animal husbandry, in animal breeding, in animal housing and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula (I) as an antiectoparasitic, in particular an arthropodicide such as an insecticide or an acaricide. A further aspect relates to the use of a compound of the formula (I) as an antiectoparasitic, in particular an arthropodicide such as an insecticide or an acaricide, for example in animal husbandry, in animal breeding, in stables or in the hygiene sector.

Vector control

[0102] The invention also comprises the use of a compound of the formula (I) or an insecticidal composition comprising a compound of the formula (I) in vector control (in other words, compounds of the formula (I) according to the invention can be used in the control of vectors, in particular in the control of mosquitoes, lice, fleas, flies, mites and ticks).

[0103] For the purpose of the present invention, a vector is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as, for example, viruses, worms, single-cell organisms and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted either mechanically (for example trachoma by non-stinging flies) to a host, or by injection (for example malaria parasites by mosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are: 1) Mosquitoes - Anopheles: malaria, filariasis; - 5 -

- Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms;

- Aedes: yellow fever, dengue fever, filariasis, other viral diseases;

- Simuliidae: transmission of worms, in particular Onchocerca volvulus; 2) Lice: skin infections, epidemic typhus; 3) Fleas: plague, endemic typhus;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo haemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia canis canis).

[0104] Examples of vectors in the sense of the present invention are insects, for example aphids, flies, leafhoppers or thrips, which are capable of transmitting plant viruses to plants. Other vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.

[0105] Further examples of vectors in the sence of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks capable of transmitting pathogens to animals and/or humans.

[0106] Vector control is also possible if the compounds of the formula (I) are resistance-breaking.

[0107] Compounds of the formula (I) are suitable for use in the prevention of diseases and/or pathogens transmitted by vectors. Thus, a further aspect of the present invention is the use of compounds of the formula (I) for vector control, for example in agriculture, in horticulture, in gardens and in leisure facilities, and also in the protection of materials and stored products.

Protection of industrial materials

[0108] The compounds of the formula (I) are suitable for protecting industrial materials against attack or destruction by insects, for example from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0109] Industrial materials in the present context are understood to mean inanimate materials, such as preferably plastics, adhesives, sizes, papers and cards, leather, wood, processed wood products and coating compositions. The use of the invention for protecting wood is particularly preferred. - -

[01 10] In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and/or at least one fungicide.

[01 1 1 ] In a further embodiment, the compounds of the formula (I) are present as a ready-to-use pesticide, i.e. they can be applied to the material in question without further modifications. Suitable further insecticides or fungicides are in particular those mentioned above.

[01 12] Surprisingly, it has also been found that the compounds of the formula (I) can be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling. Likewise, the compounds of the formula (I), alone or in combinations with other active compounds, can be used as antifouling agents. Control of animal pests in the hygiene sector

[01 13] The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be applied in the domestic sector, in the hygiene sector and in the protection of stored products, especially for controlling insects, arachnids and mites encountered in enclosed spaces such as dwellings, factory halls, offices, vehicle cabins. For controlling animal pests, the compounds of the formula (I) are used alone or in combination with other active compounds and/or auxiliaries. They are preferably used in domestic insecticide products. The compounds of the formula (I) are effective against sensitive and resistant species, and against all developmental stages.

[01 14] These pests include, for example, pests from the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.

[01 15] They are used, for example, in aerosols, pressure- free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.

Synthetic schemes

[01 16] The compounds of formula (lb), wherein R², R³, R⁵, n and m are as previously defined and A represents (Ci-C i)alkyl can be prepared by the methods illustrated in Scheme A: - 7 -

Scheme A

[0117] Step (a) of Scheme A is an iron-catalysed cross-coupling reaction of aroyl chlorides (II) with Grignard-type reagents (B. Scheiper, M. Bonnekessel, H. Krause, and A. Fiirstner, J. Org. Chem. 2004, 69, 3943-3949).

[0118] Step (b) of Scheme A is an a-bromination of the aryl alkyl ketones (III). Mild a-bromination of ketones can be achieved with pyridinium tribromide in dichloromethane (C. Djerassi, C. R. Scholz, J. Am. Chem. Soc. 1948, 70, 417-418). Other possible reagent systems include e.g. N-bromosuccinimide or bromine in acetic acid.

[0119] In step (c) of Scheme A the a-bromo alkyl aryl ketone (IV) reacts with a pyrazole to give a- pyrazolyl alkyl aryl ketone (V).

[0120] Step (d) of Scheme A is a Grignard arylation of a-pyrazolyl alkyl aryl ketone (V) with an asymmetric induction at the a-carbon, which leads mainly to one of the possible diastereomers of (Ic) (e.g., greater 70:30, 80:20 or even 90:10). The stereoselectivity can be attributed to the fact that the magnesium cation, both in the reactant (V) and in the product (Ic), complexes with a nitrogen of the pyrazolyl moiety and the carbonyl oxygen forcing the formation of a particular diastereomer (B. N. Hitesh Kumar, V. Murugesan, T. Prakasam, P. S. Srinivasan, D. V. Ramana, Tetrahedron, Asymmetry 2009, 20, 2773-2779). The relative stereochemistry of (Ic) was confirmed by X-ray analysis of example 1-2 (see Figure 1). - -

[0121 ] Arylmagnesium compounds are commercially available or can be prepared e.g. by a LiCl- mediated Br/Mg exchange using the isopropylmagnesium chloride lithium chloride complex (A. Krasovskiy, P. Knochel, Angew. Chem. Int. Ed. 2004, 43, 3333-3336).

[0122] The compounds of formula (Id), wherein R² and R³ n and m are identical and R² and n, R⁵ are as previously defined and A is (Ci-C i)alkyl, preferably methyl, may also be prepared by the methods illustrated in Scheme B wherein R⁶ is (Ci-C i)alkyl and Q is a leaving group, preferably chloro or bromo, as has been described previously in EP 0 158 448, EP 0 194 064, and WO 1986/002072:

Scheme B

(VI) (VII) (Id) [0123] An a-halopropionic ester (VI) is reacted with a pyrazol to give the corresponding a-(lH- pyrazol-l -yl) propionic ester (VII). The latter is then reacted with two equivalents of an aryl Grignard- reagent to give the corresponding 1 ,1 -symmetrically disubstituted 2-(lH-pyrazol-l -yl)propanols (Id).

[0124] The compounds of formula (lb), wherein Q, R², R³, R⁵, m and n are as previously defined and A is (Ci-C i)alkyl, preferably methyl, may also be prepared by the methods illustrated in Scheme C as has been described previously in EP 0 158 448 and WO 1986/002072:

- -

Scheme C

[0125] An a-halo propiophenone (VIII) is reacted with an aryl Grignard-species to give oxirane (IX) which is then reacted with a pyrazole to give the corresponding 1,1-disubstituted 2-(lH-pyrazol-l- yl)propanols (lb).

Examples Key Intermediates

Preparation of 2-(4-fluoro-lH-pyrazol-l-yl)-l-[4-(trifluoromethoxy)phenyllpropan-l-one (V-l)

[0126] A solution of ethylmagnesium chloride (2 M in THF, 9.38 mL, 18.77 mmol) was added over 50 min to a solution of 4-(trifluoromethoxy)benzoyl chloride (II-l) (purity 98%, 5.00 g, 21.82 mmol) and iron(III) acetylacetonate (385 mg, 1.09 mmol) in THF (70 mL) at -20°C under argon. After stirring for 10 min at that temperature, the reaction mixture was quenched with 1 N HCl and the mixture was repeatedly extracted with CH2CI2. The combined organic layers were washed with 2 N NaOH, dried over Na2S04 and evaporated to yield l-[4-(trifluoromethoxy)phenyl]propan-l -one (III-l) (purity 90%, 4.95 g, 93%). ¾ NMR (400 MHz, DMSO-de) δ 1.09 (t, 3H), 3.07 (q, 2H), 7.50 (d, 2H), 8.10 (d, 2H).

Step 2

[0127] To a solution of l-[4-(trifluoromethoxy)phenyl]propan-l-one (III-l) (purity 80%, 15.87 g, 58.19 mmol) in dichloromethane (200 mL) was added in portions pyridinium tribromide (purity 90%, 20.68 g, 58.19 mmol). After stirring at room temperature overnight, the reaction mixture was quenched with 1 N HCl. The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica (cyclohexane/ethyl acetate, 99.5/0.5 to 97/3) provided 2-bromo-l-[4- - -

(trifluoromethoxy)phenyl]propan-l-one (IV-1) (purity 98%, 11.19 g, 63%). ¾ NMR (400 MHz, CDC1₃) δ 1.91 (d, 3H), 5.23 (q, 1H), 7.31 (d, 2H), 8.09 (d, 2H).

Step 3

[0128] To a solution of 4-fluoro-lH-pyrazole (purity 97.5%, 1.02 g, 11.55 mmol) in acetonitrile (30 mL) was added successively anhydrous potassium carbonate (1.92 g, 13.86 mmol) and a solution of 2- bromo-l-[4-(trifluoromethoxy)phenyl]propan-l-one (IV-1) (purity 98%, 3.50 g, 11.55 mmol) in acetonitrile (10 mL). After stirring at room temperature overnight, the reaction mixture was poured into water and repeatedly extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica (cyclohexane/ethyl acetate, 100/0 to 87/13) provided 2-(4-fluoro-lH-pyrazol- l-yl)-l -[4-(trifluoromethoxy)phenyl]propan-l-one (V-l) (2.76 g, 79%). ¾ NMR (400 MHz, DMSO-de) δ 1.61 (d, 3H), 6.19 (q, 1H), 7.46 (d, 1H), 7.51 (d, 2H), 8.09 (m, 3H).

Preparation of 2-(4-fluoro-lH-pyrazol-l-yl)-l-(4-methylphenyl)propan-l-one (V-2)

(IV-2) (V-2)

[0129] To a solution of 2-bromo-l-[4-methylphenyl]propan-l-one (IV-2) (commercially available, purity 90%, 1.60 g, 6.34 mmol) in acetonitrile (45 mL) was added successively anhydrous potassium carbonate (1.05 g, 7.61 mmol) and 4-fluoro-lH-pyrazole (546 mg, 6.34 mmol). After stirring at room temperature overnight, the reaction mixture was filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica (cyclohexane/ethyl acetate, 98/2 to 70/30) provided 2-(4-fluoro-lH-pyrazol-l-yl)-l-[4-methylphenyl]propan-l-one (V-2) (purity 98%, 1.37 g, 91%). ¾ NMR (400 MHz, DMSO-de) δ 1.60 (d, 3H), 2.37 (s, 3H), 6.14 (q, 1H), 7.33 (d, 2H), 7.44 (d, 1H), 7.87 (d, 2H), 8.06 (d, 1H). - -

[0130] The following compounds were prepared using procedures analogous to those described above for the synthesis of intermediate (V-l) or (V-2) using the appropriate starting materials which are commercially available or prepared using preparations well-known to those skilled in the art.

Table 1

Int.

R⁵ A (R³)_m Characterization

No.

¾ NMR (400 MHz, DMSO-de) δ 1.61 (d, 3H), 6.19 (q, 1H), 7.46 (d,

V-l F CH₃ 4-OCF₃

1H), 7.51 (d, 2H), 8.09 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.60 (d, 3H), 2.37 (s, 3H), 6.14 (q,

V-2 F CH₃ 4-CH₃

1H), 7.33 (d, 2H), 7.44 (d, 1H), 7.87 (d, 2H), 8.06 (d, 1H).

¾ NMR (400 MHz, CDC1₃) δ 1.75 (d, 3H), 5.96 (q, 1H), 7.29 (d,

V-3 CI CH₃ 4-OCF₃

2H), 7.44 (s, 1H), 7.54 (s, 1H), 8.04 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.76 (d, 3H), 5.99 (q, 1H), 7.29 (d,

V-4 Br CH₃ 4-OCF₃

2H), 7.48 (s, 1H), 7.57 (s, 1H), 8.04 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.81 (d, 3H), 6.13 (q, 1H), 7.34 (d,

V-5 CN CH₃ 4-OCF₃

2H), 7.81 (s, 1H), 8.04 (s, 1H), 8.05 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.73 (d, 3H), 2.05 (s, 3H), 5.92 (q,

V-6 CH₃ CH₃ 4-OCF₃

1H), 7.26 (m, 3H), 7.33 (s, 1H), 8.03 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.72 (d, 3H), 3.72 (s, 3H), 5.86 (q,

V-7 OCH₃ CH₃ 4-OCF₃

1H), 7.14 (s, 1H), 7.26 (m, 3H), 8.02 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.62 (d, 3H), 6.23 (q, 1H), 7.45 (d,

V-8 F CH₃ 4-CF₃

1H), 7.89 (d, 2H), 8.11 (m, 3H). - -

Examples

Preparation of rg/-(li?,2i?)-l-[3,5-difluoro-4-(trifluoromethyl)phenyll-2-(4-fluoro-lH-pyrazol-l- yl)-l-[4-(trifluoromethoxy)phenyllpropan-l-ol (I-l)

[0131] A solution of isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 0.59 mL, 0.76 mmol) was added to 5-bromo-l,3-difluoro-2-(trifluoromethyl)benzene (purity 97%, 197 mg, 0.73 mmol) at 0°C under argon. After stirring at that temperature for 30 min, a solution of 2-(4-fluoro- lH-pyrazol-l-yl)-l-[4-(trifluoromethoxy)phenyl]propan-l-one (V-1) (purity 99%, 80 mg, 0.26 mmol) in 1 mL THF was added. After stirring at room temperature for 40 min, the reaction mixture was quenched with 10%) aqueous HC1, dried over Na2SO i, filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica (cyclohexane/acetone, 97/3 to 92/8) provided re/-(lR,2R)-l-[3,5-difluoro-4-(trifluoromethyl)phenyl]-2-(4-fluoro-lH-pyrazol-l-yl)-l-[4- (trifluoromethoxy)phenyl]propan-l-ol (I-l) (purity 97%, 82 mg, 62%). ¾ NMR (400 MHz, DMSO-de) δ 1.35 (d, 3H), 5.76 (q, 1H), 6.68 (s, 1H), 7.33 (d, 1H), 7.42 (m, 4H), 7.83 (m, 3H). Preparation of rg/-(li?,2i?)-l-(3,4-difluorophenyl)-2-(4-fluoro-lH-pyrazol-l-yl)-l-[4- methylphenyllpropan-l-ol (1-2) - 5 - ntiom

[0132] To a solution of 2-(4-fluoro-lH-pyrazol-l-yl)-l-[4-methylphenyl]propan-l-one (V-2) (83 mg, 0.36 mmol) in THF (5 mL) was added a solution of 3,4-difluorophenyl magnesium bromide (0.5 M in THF, 0.93 mL, 0.47 mmol). After being stirred at room temperature for 2 h, the reaction mixture was quenched with 1 N HC1, dried over Na2SO i, filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica (cyclohexane/acetone, 100/0 to 0/100) provided rel-(\R,2R)- 1 -(3,4-difluorophenyl)-2-(4-fluoro- 1 H-pyrazol- 1 -yl)- 1 -[4-methylphenyl]propan- 1 - ol (1-2) (purity 97%, 82 mg, 64%). ¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 2.27 (s, 3H), 5.59 (q, 1H), 6.17 (s, 1H), 7.15-7.25 (m, 2H), 7.17 (d, 2H), 7.30 (d, 1H), 7.38 (m, 1H), 7.51 (d, 2H), 7.79 (d, 1H).

[0133] The following compounds were prepared using procedures analogous to those described above for the synthesis of example (I-l) or (1-2) using the appropriate starting materials which are commercially available or prepared using preparations well-known to those skilled in the art.

Table 2 orr

- -

Ex.

R⁵ A Characterization

No. (R³)_m (R²)n

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

3- F,

2.27 (s, 3H), 5.59 (q, 1H), 6.17 (s, 1H), 7.20 (m,

1-2 F CH₃ 4-CH₃

2H), 7.17 (d, 2H), 7.30 (d, 1H), 7.38 (m, 1H),

4- F

7.51 (d, 2H), 7.79 (d, 1H).

¾ NMR (400 MHz, CDC1₃) δ 1.46 (d, 3H), 5.12 (q, 1H), 6.00 (s, 1H), 7.03 (d, 2H), 7.19 (d,

1-3 CI CH₃ 4-OCF₃ 4-OCF₃

2H), 7.30 (s, 1H), 7.31 (s, 1H), 7.40 (d, 2H), 7.59 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.46 (d, 3H), 5.15 (q, 1H), 6.00 (s, 1H), 7.03 (d, 2H), 7.19 (d,

1-4 Br CH₃ 4-OCF₃ 4-OCF₃

2H), 7.32 (s, 1H), 7.35 (s, 1H), 7.40 (d, 2H), 7.59 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.51 (d, 3H), 5.28 (q, 1H), 5.51 (s, 1H), 7.04 (d, 2H), 7.21 (d,

1-5 CN CH₃ 4-OCF₃ 4-OCF₃

2H), 7.39 (d, 2H), 7.60 (d, 2H), 7.69 (s, 1H), 7.77 (s, 1H).

¾ NMR (400 MHz, CDC1₃) δ 1.46 (d, 3H),

1-6 F CH₃ 4-OCF₃ 4-OCF₃ 5.05 (q, 1H), 6.04 (s, 1H), 7.03 (d, 2H), 7.20

(m, 4H), 7.41 (d, 2H), 7.59 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.44 (d, 3H),

1-7 CH₃ CH₃ 4-OCF₃ 4-OCF₃ 1.92 (s, 3H), 5.09 (q, 1H), 6.58 (s, 1H), 7.00 (m,

3H), 7.18 (m, 3H), 7.40 (d, 2H), 7.60 (d, 2H).

¾ NMR (400 MHz, CDC1₃) δ 1.44 (d, 3H), 3.61 (s, 3H), 5.02 (q, 1H), 6.31 (s, 1H), 6.94 (s,

1-8 OCH₃ CH₃ 4-OCF₃ 4-OCF₃

1H), 7.02 (d, 2H), 7.12 (s, 1H), 7.19 (d, 2H), 7.41 (d, 2H), 7.59 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H), 5.67 (q, 1H), 6.29 (s, 1H), 7.21 (d, 2H), 7.31 (d,

1-9 F CH₃ 4-OCF₃ CI

1H), 7.36 (d, 2H), 7.46 (d, 2H), 7.75 (d, 2H), 7.79 (d, 1H).

¾ NMR (400 MHz, DMSO-de) δ 1.48 (d, 3H),

2-F,

5.71 (q, 1H), 6.57 (s, 1H), 7.05 (m, 2H), 7.13

1-10 F CH₃ 4-OCF₃

(d, 1H), 7.36 (d, 2H), 7.68 (m, 3H), 7.77 (d, 4-OCF₃

1H).

2-F, ¾ NMR (400 MHz, DMSO-de) δ 1.51 (d, 3H),

1-11 F CH₃ 4-OCF₃ 5.77 (q, 1H), 6.68 (s, 1H), 7.13 (d, 1H), 7.38

4-CF₃ (m, 4H), 7.69 (d, 2H), 7.80 (m, 2H). - 7 -

Ex.

R⁵ A

No. (R³)_m (R²)n Characterization

¾ NMR (400 MHz, DMSO-de) δ 1.30 (d, 3H),

3- CH₃,

2.15 (s, 3H), 5.67 (q, IH), 6.26 (s, IH), 7.09 (m,

1-12 F CH₃ 4-OCF₃

IH), 7.31 (d, IH), 7.38 (m, 3H), 7.45 (d, IH),

4- CF₃

7.77 (d, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H),

1-13 F CH₃ 4-OCF₃ 4-CH₃ 2.15 (s, 3H), 5.66 (q, IH), 6.10 (s, IH), 6.96 (d,

2H), 7.34 (m, 5H), 7.72 (d, 2H), 7.80 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

3- F,

5.67 (q, IH), 6.38 (s, IH), 7.23 (m, 2H), 7.32

1-14 F CH₃ 4-OCF₃

(d, IH), 7.37 (d, 2H), 7.45 (m, IH), 7.78 (m,

4- F

3H).

3- F,

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

1-15 F CH₃ 4-OCF₃ 4- F, 5.69 (q, IH), 6.51 (s, IH), 7.36 (m, 5H), 7.80

(m, 3H).

5- F

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H), 5.69 (q, IH), 6.16 (s, IH), 7.06 (m, IH), 7.16 (t,

1-16 F CH₃ 4-OCF₃ H

2H), 7.30 (d, IH), 7.33 (d, 2H), 7.47 (d, 2H), 7.75 (d, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.36 (d, 3H),

3- (OCF₃),

5.67 (q, IH), 6.54 (s, IH), 7.22 (d, IH), 7.40 (d,

1-17 F CH₃ 4-OCF₃

2H), 7.46 (m, 2H), 7.55 (s, IH), 7.75 (d, IH),

4- (OCF₃)

7.81 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 5.69 (q, IH), 6.38 (s, IH), 7.19 (d, IH), 7.30

1-18 F CH₃ 4-OCF₃ 3,4 -OCF2O- (m, 2H), 7.37 (d, 2H), 7.46 (m, IH), 7.78 (d, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.37 (d, 3H),

3- CF₃, 5.67 (q, IH), 6.61 (s, IH), 7.21 (d, IH), 7.41 (d,

1-19 F CH₃ 4-OCF₃

4- OCF₃ 2H), 7.46 (m, IH), 7.73 (m, 2H), 7.78 (d, IH),

7.82 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.26 (d, 3H),

2-CH₃, 2.09 (s, 3H), 5.57 (q, IH), 6.41 (s, IH), 6.95 (s,

1-20 F CH₃ 4-OCF₃

4-OCF₃ IH), 7.05 (d, IH), 7.34 (m, 3H), 7.50 (d, 2H),

7.81 (d, IH), 7.90 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.35 (d, 3H), 5.68 (q, IH), 6.38 (s, IH), 7.23 (d, IH), 7.39 (d,

1-21 F CH₃ 4-OCF₃ 4-CF(CF₃)₂

2H), 7.45 (d, 2H), 7.66 (d, 2H), 7.72 (d, IH), 7.80 (d, 2H). - -

Ex.

R⁵ A Characterization

No. (R³)_m (R²)n

¾ NMR (400 MHz, DMSO-de) δ 1.30 (d, 3H), 5.68 (q, IH), 6.25 (s, IH), 6.96 (d, 2H), 7.12 (t,

1-22 F CH₃ 4-OCF₃ 4-OCHF2

IH), 7.32 (d, IH), 7.37 (d, 2H), 7.50 (d, 2H), 7.75 (d, 2H), 7.80 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.33 (d, 3H), 5.69 (q, IH), 6.37 (s, IH), 7.07 (m, IH), 7.27

1-23 F CH₃ 4-OCF₃ 3-OCF₃

(d, IH), 7.30 (d, IH), 7.38 (m, 3H), 7.43 (d, IH), 7.77 (d, IH), 7.79 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.34 (d, 3H),

1-24 F CH₃ 4-OCF₃ 4-CF₃ 5.75 (q, IH), 6.42 (s, IH), 7.28 (d, IH), 7.37 (d,

2H), 7.53 (d, 2H), 7.67 (d, 2H), 7.79 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.33 (d, 3H),

1-25 F CH₃ 4-OCF₃ 4-SCF₃ 5.71 (q, IH), 6.38 (s, IH), 7.27 (d, IH), 7.37 (d,

2H), 7.50 (d, 2H), 7.60 (d, 2H), 7.78 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 5.67 (q, IH), 6.29 (s, IH), 6.73 (tm, IH), 7.05

1-26 F CH₃ 4-OCF₃ 4-CF2CHF2

(d, 2H), 7.29 (d, IH), 7.37 (d, 2H), 7.51 (d, 2H), 7.78 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 5.69 (q, IH), 6.29 (s, IH), 7.30 (m, 3H), 7.35

1-27 F CH₃ 4-OCF₃ 4-CF2PI1

(d, 2H), 7.43 (m, 5H), 7.56 (d, 2H), 7.77 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H), 5.75 (q, IH), 6.23 (s, IH), 7.07 (t, IH), 7.17 (t,

1-28 F CH₃ 4-CF₃ H

2H), 7.32 (d, IH), 7.49 (d, 2H), 7.72 (d, 2H), 7.80 (d, IH), 7.87 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H), 2.15 (s, 3H), 5.72 (q, IH), 6.17 (s, IH), 6.97 (d,

1-29 F CH₃ 4-CF₃ 4-CH₃

2H), 7.33 (d, IH), 7.37 (d, 2H), 7.70 (d, 2H), 7.82 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H), 5.73 (q, IH), 6.36 (s, IH), 7.22 (d, 2H), 7.32 (d,

1-30 F CH₃ 4-CF₃ 4-Cl

IH), 7.47 (d, 2H), 7.73 (d, 2H), 7.81 (d, IH), 7.87 (d, 2H).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 5.74 (q, IH), 6.40 (s, IH), 7.16 (d, 2H), 7.30 (d,

1-31 F CH₃ 4-CF₃ 4-OCF₃

IH), 7.57 (d, 2H), 7.74 (d, 2H), 7.80 (d, IH), 7.88 (d, 2H). - -

- 5 -

Ex.

R⁵ A ation

No. (R³)_m (R²)n Characteriz

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H), 5.65 (q, IH), 6.25 (s, IH), 7.13 (d, 2H), 7.19 (t,

1-42 F CH₃ 4-F 4-OCF₃

2H), 7.28 (d, IH), 7.53 (d, 2H), 7.67 (dd, 2H), 7.77 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H), 5.63 (q, IH), 6.21 (s, IH), 7.18 (m, 4H), 7.30

1-43 F CH₃ 4-F 4-Cl

(d, IH), 7.44 (d, 2H), 7.65 (dd, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H), 2.15 (s, 3H), 5.66 (q, IH), 6.07 (s, IH), 6.96 (d,

1-44 F CH₃ 3-F 4-CH₃

2H), 7.04 (m, IH), 7.32 (d, IH), 7.40 (m, 3H), 7.37 (d, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

3- F,

5.68 (q, IH), 6.35 (s, IH), 7.14 (d, 2H), 7.28 (d,

1-45 F CH₃ 4-OCF₃

IH), 7.46 (m, 2H), 7.53 (d, 2H), 7.70 (m, IH),

4- F

7.75 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H), 2.14 (s, 3H), 2.24 (s, 3H), 5.58 (q, IH), 5.90 (s,

1-46 F CH₃ 4-CH₃ 4-CH₃

IH), 6.92 (d, 2H), 7.12 (d, 2H), 7.30 (d, IH), 7.32 (d, 2H), 7.47 (d, 2H), 7.80 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H),

3- F,

5.66 (q, IH), 6.31 (s, IH), 7.22 (d, 2H), 7.30 (d,

1-47 F CH₃ 4-Cl

IH), 7.44 (m, 2H), 7.47 (d, 2H), 7.68 (m, IH),

4- F

7.76 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

3- F,

5.67 (q, IH), 6.35 (s, IH), 7.10 (m, IH), 7.25

1-48 F CH₃ 3-F

(m, 2H), 7.32 (d, IH), 7.47 (m, 4H), 7.78 (d,

4- F

IH).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H), 2.15 (s, 3H), 5.62 (q, IH), 6.02 (s, IH), 6.95 (d,

1-49 F CH₃ 4-F 4-CH₃

2H), 7.15 (t, 2H), 7.31 (d, IH), 7.34 (d, 2H), 7.62 (dd, 2H), 7.79 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.28 (d, 3H),

3- F,

2.16 (s, 3H), 5.65 (q, IH), 6.12 (s, IH), 6.97 (d,

1-50 F CH₃ 4-CH₃

2H), 7.32 (d, IH), 7.36 (d, 2H), 7.42 (m, 2H),

4- F

7.62 (m, IH), 7.77 (d, IH).

¾ NMR (400 MHz, DMSO-de) δ 1.32 (d, 3H),

3- F, 3- F,

5.66 (q, IH), 6.40 (s, IH), 7.24 (m, 2H), 7.32

1-51 F CH₃

(d, IH), 7.46 (m, 3H), 7.71 (m, IH), 7.77 (d,

4- F 4- F

IH). -5 -

- 5 -

Ex.

R⁵ A

N (R³)_m (R²)n Characterization

o.

3- F, ¾ NMR (600 MHz, CD₃CN) δ 1.18 (t, 3H),

1-62 F CH₃ CH₂CH₃ 1.38 (d, 3H), 2.61 (q, 2H), 5.43 (q, 1H), 5.81 (s,

4- OCF₃ 1H), 7.20-7.57 (m, 9H).

¾ NMR (600 MHz, CD₃CN) δ 1.17 (t, 3H), 1.38 (d, 3H), 2.60 (q, 2H), 5.46 (q, 1H), 5.75 (s,

1-63 F CH₃ CH₂CH₃ 4-OCF₃

1H), 7.08 (d, 2H), 7.21 (m, 3H), 7.50 (d, 2H), 7.56 (m, 3H).

¾ NMR (400 MHz, CD₃CN) δ 1.17 (t, 3H), 1.39 (d, 3H), 2.60 (q, 2H), 5.50 (q, 1H), 5.82 (s,

1-64 F CH₃ CH₂CH₃ 4-CF₃

1H), 7.22 (m, 3H), 7.49 (dd, 4H), 7.58 (d, 1H), 7.68 (d, 2H).

¾ NMR (400 MHz, CD₃CN) δ 1.38 (d, 3H),

1-65 F CH₃ 4-SCH₃ 4-OCF₃ 2.45 (s, 3H), 5.43 (q, 1H), 5.79 (s, 1H), 7.09 (d,

2H), 7.26 (m, 5H), 7.55 (m, 3H).

¾ NMR (400 MHz, CD₃CN) δ 1.40 (d, 3H),

1-66 F CH₃ 4-SCH₃ 4-CF₃ 2.45 (s, 3H), 5.48 (q, 1H), 5.88 (s, 1H), 7.21 (m,

2H), 7.50 (m, 5H), 7.67 (dd, 2H).

3- F, ¾ NMR (400 MHz, CD₃CN) δ 1.37 (d, 3H),

2.30 (s, 3H), 5.35 (q, 1H), 5.83 (s, 1H), 7.20 (m,

1-67 F CH₃ 4-CH₃ 4- F, 5H), 7.47 (d, 2H), 7.57 (d, 1H).

5- F

¾ NMR (400 MHz, CD₃CN) δ 1.37 (d, 3H),

1-68 F CH₃ 4-SCH₃ 4-OCF₃ 5.49 (q, 1H), 6.00 (s, 1H), 7.20 (m, 5H), 7.58

(m, 3H), 7.70 (m, 6H).

¾ NMR (400 MHz, DMSO-de) δ 1.34 (d, 3H),

1-69 F CH₃ 4-OCF₃ 4-CN 5.74 (q, 1H), 6.45 (s, 1H), 7.27 (d, 1H), 7.36 (d,

2H), 7.64 (s, 4H), 7.76 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.34 (d, 3H),

1-70 F CH₃ 4-OCF₃ 4-C0₂CH₃ 3.78 (s, 3H), 5.74 (q, 1H), 6.37 (s, 1H), 7.27 (d,

1H), 7.36 (d, 2H), 7.60 (d, 2H), 7.76 (m, 5H).

¾ NMR (400 MHz, DMSO-de) δ 1.31 (d, 3H),

1-71 F CH₃ 4-1 4-OCF₃ 5.62 (q, 1H), 6.25 (s, 1H), 7.13 (d, 2H), 7.28 (d,

1H), 7.44 (d, 2H), 7.51 (d, 2H), 7.70 (m, 3H).

¾ NMR (400 MHz, DMSO-de) δ 1.33 (d, 3H),

1-72 F CH₃ 4-1 4-CF₃ 5.70 (q, 1H), 6.35 (s, 1H), 7.27 (d, 1H), 7.46 (d,

2H), 7.48 (d, 2H), 7.64 (d, 2H), 7.72 (d, 2H), -5 -

Ex.

R⁵ A

N R³)_m (R²)n Characterization o. (

7.80 (d, 1H).

- 5 - Biological Examples Boophilus microplus - Iniectiontest (BOOPMI Inj)

Solvent: dimethyl sulfoxide

[0134] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with solvent to the desired concentration.

[0135] Five adult engorged female ticks (Boophilus microplus) are injected with 1 μΐ compound solution into the abdomen. Ticks are transferred into replica plates and incubated in a climate chamber.

[0136] After 7 days the egg deposition of fertile eggs is monitored. Eggs where fertility is not visible are stored in a climate chamber till hatching after about 42 days. An efficacy of 100 % means that all eggs are infertile; 0 % means that all eggs are fertile.

[0137] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 2(^g/animal: 1-1, 1-9, 1-24, 1-30, 1-67, 1-69

[0138] In this test, for example, the following compounds from the preparation examples showed good activity of 98% at an application rate of 20μg/animal: 1-6

Cooperia curticei - Test (COOPCU)

Solvent: dimethyl sulfoxide

[0139] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with "Ringer's solution" to the desired concentration.

[0140] Approximately 40 nematode larvae (Cooperia curticei) are transferred into a test tube containing the compound solution.

[0141] After 5 days percentage of larval mortality is recorded. 100 % efficacy means all larvae are killed; 0%> efficacy means no larvae are killed.

[0142] In this test for example, the following compounds from the preparation examples showed good activity of 90%> at an application rate of lOOppm: 1-30

Ctenocephalides felis - oral test (CTECFE)

Solvent: dimethyl sulfoxide [0143] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with cattle blood to the desired concentration.

[0144] Approximately 20 adult unfed cat fleas (Ctenocephalides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom, are filled with cattle blood supplied with compound solution and placed on the gauze covered top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37 °C whereas the flea chamber is kept at room temperature.

[0145] After 2 days mortality in % is determined. 100 % means that all the fleas have been killed; 0 % means that none of the fleas have been killed.

[0146] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of lOOppm: 1-30

Lucilia cuprina - test (LUCICU) solvent: dimethyl sulfoxide

[0147] 10 mg active compound are dissolved in 0,5 ml Dimethylsulfoxid. Serial dilutions are made to obtain the desired rates. [0148] Approximately 20 1st instar larvae of the Australian sheep blowfly (Lucilia cuprina ) are transferred into a test tube containing minced horse meat and compound solution of the desired concentration.

[0149] After 2 days mortality in % is determined. 100 % means that all the larvae have been killed; 0 % means that none of the larvae have been killed. [0150] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of lOOppm: 1-1, 1-3, 1-4, 1-5, 1-6, 1-9, 1-24, 1-30, 1-69, 1-70.

Musca domestica - test (MUSCDO)

Solvent: dimethyl sulfoxide

[0151] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.

[0152] 10 adult house flies (Musca domestica) are transferred into a container, containing a sponge soaked with a mixture of sugar solution and compound solution of the desired concentration.

[0153] After 2 days mortality in % is determined. 100 % means that all the flies have been killed; 0 % means that none of the flies have been killed. - 5 -

[0154] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of lOOppm: 1-1, 1-5, 1-6, 1-9, 1-24

[0155] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of lOOppm: 1-30, 1-70

[0156] In this test, for example, the following compounds from the preparation examples showed good activity of 80%> at an application rate of lOOppm: 1-3, 1-4

Meloidogyne incognita - test (MELGIN)

Solvent: 125.0 parts by weight of acetone

[0157] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration.

[0158] Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of the southern root-knot nematode (Meloidogyne incognita) and salad seeds. The salad seeds germinate and the seedlings grow. Galls develop in the roots.

[0159] After 14 days the nematicidal activity is determined on the basis of the percentage of gall formation. 100%) means that no galls were found; 0%> means that the number of galls found on the roots of the treated plants was equal to that in untreated control plants.

[0160] In this test, for example, the following compounds from the preparation examples showed good activity of 100%> at an application rate of 20ppm: 1-47

[0161] In this test, for example, the following compounds from the preparation examples showed good activity of 90%> at an application rate of 20ppm: 1-1, 1-24, 1-51, 1-72

[0162] In this test, for example, the following compounds from the preparation examples showed good activity of 80%> at an application rate of 20ppm: 1-48, 1-49 Myzus persicae - spray test (MYZUPE)

Solvent: parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylarylpolyglycolether [0163] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0164] Chinese cabbage (Brassica pekinensis) leaf- disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient of the desired concentration.

[0165] After 6 days, mortality in % is determined. 100 % means all aphids have been killed; 0 % means none of the aphids have been killed.

[0166] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500g/ha: 1-3, 1-6, 1-14, 1-45, 1-56, 1-71

[0167] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500g/ha: 1-9, 1-13, 1-15, 1-21, 1-26, 1-55, 1-70

[0168] In this test, for example, the following compounds from the preparation examples showed good activity of 90%> at an application rate of 1 OOg/ha: 1-7 Spodoptera frugiperda - spray test (SPODFR)

Solvent: 78.0 parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylarylpolyglycolether

[0169] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water. - 5 -

[0170] Maize (Zea mays) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda).

[0171] After 7 days, mortality in % is determined. 100% means all caterpillars have been killed and 0% means none of the caterpillars have been killed.

[0172] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500g/ha: 1-1 , 1-3, 1-5, 1-6, 1-9, 1-13, 1-22, 1-24, 1-31 , 1-45, 1-54, 1-55, 1-56, 1-57, 1-58, 1-60, 1-65, 1-69, 1-70, 1-71, 1-72

[0173] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 500g/ha: 1-27, 1-36, 1-39, 1-42, 1-47, 1-59, 1-65

[0174] In this test, for example, the following compounds from the preparation examples showed good activity of 80%> at an application rate of 500g/ha: 1-21

[0175] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of lOOg/ha: 1-4, 1-8, 1-70 (100%), 1-71 (100%) Tetranychus urticae - spray test OP-resistant (TETRUR)

Solvent: parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylarylpolyglycolether

[0176] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0177] French beans (Phaseolus vulgaris) which are heavily infested with all stages of the two spotted spidermite (Tetranychus urticae), are sprayed with a preparation of the active ingredient of the desired concentration.

[0178] After 6 days mortality in %> is determined. 100%) means all spider mites have been killed and 0%> means none of the spider mites have been killed.

[0179] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500g/ha: 1-1, 1-3, 1-5, 1-9, 1-22, 1-55, 1-69 - 5 -

[0180] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500g/ha: 1-21, 1-24, 1-25, 1-30, 1-59, 1-65, 1-66, 1-70, 1-71

Anopheles Test (ANPHGB treated surface contact bioassay)

Solvent: Acetone [0181] To create an appropriate active ingredient formulation 2 mg of active substance were dissolved in 1 ml of acetone. This solution was pipetted onto a glazed tile. After evaporation of the acetone adult mosquitoes of the species Anopheles gambiae (homozygous kdr) were placed onto the treated tile. The exposure time was 30 minutes.

[0182] 2 Hours after contact to the treated surface the test animals with knock-down symptoms were counted. Here, efficacy of 100% means that all mosquitoes showed knock-down symptoms; efficacy of 0%> means that none of the mosquitoes showed knock-down symptoms.

[0183] In this test, the following examples of the present invention reveal an efficacy of 90-100%) at a concentration of 100 mg/m²: 1-56, 1-57, 1-59, 1-62, 1-63, 1-64, 1-55, 1-54, 1-3, 1-6, 1-7, 1-8, 1-10, 1-26, 1-9, 1-25, 1-1, 1-12, 1-11, 1-16, 1-13, 1-14, 1-15, 1-17, 1-18, 1-22, 1-24, 1-30, 1-29, 1-31 , 1-32, 1-33, 1-36, 1-38, 1- 35, 1-34, 1-40,1-50, 1-42, 1-58, 1-45, 1-2.

Example Concentration [mg/m²] Efficacy [%]

0.8 90

EP 0 158 448, ex. XIX 0.8 30 -

Aedes Test (AEDSAE treated surface contact bioassay)

Solvent: Acetone

[0184] To create an appropriate active ingredient formulation 2 mg of active substance were dissolved in 1 ml of acetone. This solution was pipetted onto a glazed tile. After evaporation of the acetone adult mosquitoes of the species Aedes aegypti were placed onto the treated tile. The exposure time was 30 minutes.

[0185] 2 Hours after contact to the treated surface the test animals with knock-down symptoms were counted. Here, efficacy of 100% means that all mosquitoes showed knock-down symptoms; efficacy of 0%> means that none of the mosquitoes showed knock-down symptoms. [0186] In this test, the following chemical compounds of the patent examples show an efficacy of 90- 100% at a concentration of 100mg/m²: 1-56, 1-57, 1-59, 1-62, 1-63, 1-64, 1-51, 1-55, 1-54, 1-3, 1-4, 1-6, 1-7, 1-8, 1-10, 1-26, 1-9, 1-25, 1-1, 1-12, 1-11, 1-16, 1-13, 1-14, 1-15, 1-17, 1-18, 1-19, 1-20, 1-22, 1-21, 1-23, 1-24, 1-28, 1-30, 1-29, 1-31, 1-32, 1-33, 1-36, 1-37, 1-39, 1-38, 1-34, 1-35, 1-41, 1-40, 1-48, 1-43, 1-52, 1-47, 1-46, 1- 50, 1-42, 1-58, 1-45, 1-53, 1-2, 1-67, 1-68.

Example Concentration [mg/m²] Efficacy [%] -6 0.8 100

EP 0 158 448, ex. XIX 0.8 10

Culex Test (CULXFA treated surface contact bioassay)

Solvent: Acetone

[0187] To create an appropriate active ingredient formulation 2 mg of active substance were dissolved in 1 ml of acetone. This solution was pipetted onto a glazed tile. After evaporation of the acetone adult mosquitoes of the species Culex quinquefasciatus were placed onto the treated tile. The exposure time was 30 minutes.

[0188] 2 Hours after contact to the treated surface the test animals with knock-down symptoms were counted. Here, efficacy of 100% means that all mosquitoes showed knock-down symptoms; efficacy of 0%> means that none of the mosquitoes showed knock-down symptoms.

[0189] In this test, the following chemical compounds of the patent examples shows efficacy of 90- 100% at a concentration of 100 mg/m²: 1-57, 1-59, 1-6, 1-52, 1-58.

Example Concentration [mg/m²] Efficacy [%]

0.8 100

EP 0 158 448, ex. XIX 0.8 60

Claims

Claims:

Compounds of the formula (I)

wherein represents (Ci-C₄)alkyl, (C3-C6)cycloalkyl, (Ci-C₄)haloalkyl or (C3-C6)halocycloalkyl, preferably methyl; represents mono- or disubstituted 1 -pyrazolyl wherein at least one substituent is at position 4 of the 1 -pyrazolyl and wherein a substituent is independently selected from the group consisting of halo, cyano, (Ci-C4)alkyl, (C3-C6)cycloalkyl, (Ci-C4)alkoxy, (Ci- C₄)haloalkyl (C3-C6)halocycloalkyl, or (Ci-C₄)haloalkoxy; represents 0, 1, 2, 3, 4 or 5; preferably 1, 2 or 3; represents independently halo, (Ci-C₄)alkyl, (Ci-C₄)haloalkyl, (Ci-C₄)alkoxy, (Ci- C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, (C₃-C₆)cycloalkyl, (C₃- C₆)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)alkyl, or -(Ci- C₄)haloalkyl-C(0)0-(Ci-C₄)haloalkyl; or two R² at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6- membered carbocyclic or heterocyclic system; represents 0, 1, 2, 3, 4 or 5; preferably 0, 1, 2 or 3, more preferably 1 or 2; represents independently halo, (Ci-C₄)alkyl, (Ci-C₄)haloalkyl, (Ci-C₄)alkoxy, (Ci- C₄)haloalkoxy, (Ci-C₄-thioalkyl, (Ci-C₄)halothioalkyl, (C₃-C₆)cycloalkyl, (C₃- C₆)halocycloalkyl, cyano, nitro, -CO(0)-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)alkyl, -(Ci-C₄)alkyl-C(0)0-(Ci-C₄)haloalkyl, -(Ci-C₄)haloalkyl-C(0)0-(Ci-C₄)alkyl, or -(Ci- C₄)haloalkyl-C(0)0-(Ci-C₄)haloalkyl; or two R³ at adjacent ring positions of the phenyl ring of the basic structure can form together with said two adjacent ring positions an optionally halosubstituted 5 or 6- membered carbocyclic or heterocyclic system;

R⁴ represents hydroxyl, halo, (Ci-C i)alkyl, (Ci-C i)haloalkyl, (Ci-C4)alkoxy, (Ci- C₄)haloalkoxy, (Ci-C₄)thioalkyl, (Ci-C₄)halothioalkyl, 0-(C₂-C₅)acyl, or 0-(C₂- Cs)haloacyl; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).

2. Compound of formula (I) according to Claim 1, wherein A represents (Ci-C2)alkyl, preferably methyl.

3. Compound of formula (I) according to Claim 1 or Claim 2, wherein

R¹ represents

k represents 1 or 2, and

R⁵ represents cyano, (Ci-C4)alkyl, (Ci-C4)haloalkyl, (Ci-C i)alkoxy, (Ci-C i)haloalkoxy halo, preferably fluoro, chloro or cyano, more preferably fluoro or cyano, under the proviso that at least one substituent R⁵ is at position 4 of the 1 -pyrazolyl.

Compound of formula (I) according to any one of claims 1 to 3, wherein

R¹ represents ^* and

R⁵ represents cyano, (Ci-C4)alkyl, (Ci-C4)haloalkyl, (Ci-C4)alkoxy, (Ci-C4)haloalkoxy or halo, preferably fluoro, chloro or cyano, more preferably fluoro or cyano, most preferably fluoro.

5. Compound of formula (I) according to any one of claims 1 to 4, wherein R² represents methyl, (Ci-C3)haloalkyl, (Ci)haloalkoxy, (Ci)halothioalkyl, fluoro or chloro; or two R² at adjacent ring positions of the phenyl ring of the basic structure form together with said two adjacent ring positions an optionally halosubstituted, preferably fluorosubstituted, 5-membered heterocycle comprising two hetero atoms selected from the group consisting of N or O, preferably O.

Compound of formula (I) according to any one of claims 1 to 5, wherein R³ represents methyl, halomethyl, (Ci)haloalkoxy or halo such as fluoro or chloro. 7. Compound of formula (I) according to any one of claims 1 to 7, wherein a compound of formula (I) is a compound of formula (la)

wherein R², R³, R⁵, are as defined in any one of claims 1 to 6 and n is 1 , 2 or 3 and m is 1 , 2 or 3, preferably wherein R⁵ is cyano, chloro or fluoro, more preferably cyano or fluoro, most preferably fluoro.

Compound of formula (I) according to any one of claims 1 to 8, wherein a compound of formula

(I) is a compound of formula (lb)

wherein R², R³, R⁵, n, and m are as defined in any one of claims 1 to 6, preferably wherein R⁵ is cyano, chloro or fluoro, more preferably cyano or fluoro and A represents (Ci-C i)alkyl.

9. Compound of formula (I) according to any one of claims 1 to 8, wherein a compound of formula (I) is a compound of formula (lc) or the enantiomer of a compound of formula (lc) or a mixture of both enantiomers

wherein A, R², R³, R⁵, n, and m are as defined in any one of claims 1 to 9 preferably wherein R⁵ is cyano or fluoro and A is methyl.

Composition, characterized in that it comprises at least one compound of the formula (I) according to any one of Claims 1 to 9 and customary extenders and/or surfactants.

11. Method for controlling insectic pests, characterized in that a compound of the formula (I) according to any of Claims 1 to 9 or a composition according to Claim 10 is allowed to act on the pests and/or their habitat.

12. Use of compounds of the formula (I) according to any of Claims 1 to 9 or of compositions according to Claim 10 for controlling insects.

Method for producing a compound (lb) according to claim 8 characterized by reacting a compound of formula

with a compound of formula (V)

resulting in a compound of formula (Ic)

wherein R , R , R , n, and m are as defined in any one of claims 1 to 6, preferably wherein R cyano, chloro or fluoro, more preferably cyano or fluoro.

Compound according to formula (V)

wherein R , R and m are as defined in any one of claims 1 to 6.