0-Carboxymethyl Oxime Ether Compounds for Combating Arthropod Pests

The present invention relates to new O-carboxymethyl oxime ether compounds which are useful for combating arthropod pests, in particular insects or arachnids. The invention also relates to a method for combating arthropod pests.

In spite of commercial pesticides available today, damage to crops, both growing and harvested, the damage of non-living material, in particular cellulose based materials such as wood or paper, and other nuisance, such as transmission of diseases, caused by arthropod pests still occur.

EP 0564928 discloses compounds of the general formula

R ¹ and R ² are, inter alia, hydrogen or optionally substituted alkyl, R ³ is, inter alia, hydrogen, optionally substituted alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, heteroaryl etc., n is 0 or 1 , Y is O, S, etc., W is hydrogen, halogen, alkyl or alkoxy, X is CHOCH ₃ , NOCH ₃ , CHCH ₃ or CHC ₂ H ₅ and Z can be amongst other NOR ⁷ , with R ⁷ being amongst other an unsubstituted or substituted CrC ₄ -alkyl.

EP-A 4754 discloses insecticidal oxime ether compounds of the formula

Ar

= N

R O-Q

wherein Ar is an aromatic radical, R is optionally substituted alkyl, alkenyl or cycloalkyl and Q is inter alia furylmethyl, thienylmethyl or benzyl.

EP-A 1125931 describes biocidal alkyl-substituted (hetero)aryl-ketoxime-O-ethers of the formula

wherein Ar ¹ and Ar ² independently of each other represent an optionally substituted aryl or hetaryl radical, m and n are independently O, 1 , 2 or 3, X is O, S, SO, SO ₂ , NH or NR, Y is H, CN, halogen, alkyl or alkoxy, R ^a and R ^b , independently of each other, might inter alia be hydrogen, halogen, alkyl, haloalkyl and the like and R ^c is hydrogen, alkyl, aryl, hetaryl, alkenyl, alkynyl or acyl. The compounds are suggested to have herbicidal, fungicidal or insecticidal activity.

DE-A 4213149 discloses heteroaryl-alkyl-ketoxime-0-ethers of the formula

wherein Ar ¹ and Ar ² independently of each other represent an optionally substituted aryl or hetaryl radical, m and n are independently O, 1 , 2 or 3, X is O, S, SO, SO ₂ , NH or NR, Y is H, CN, halogen, alkyl or alkoxy, and R is alkyl, alkenyl, alkinyl or cycloalkyl. The compounds are suggested to have acaricidal, nematicidal or insecticidal activity.

WO 02/081429 discloses oxime ether compounds of the formula

wherein A is substituted phenyl or heterocyclyl, B is H, alkyl or a radical C(O)R ¹ , C(S)R ¹ or SO ₂ R ² etc., with R ¹ , R ² being inter alia alkyl or cycloalkyl, R represents alkyl, alkenyl, haloalkyl or phenylalkyl, and X is alkyl, cycloalkyl etc. The compounds are useful for combating insects or acarides.

However, the activity of the oxime ether compounds of prior art against arthropod pests is not satisfactory.

Acetic acid [[[1 ,2-dimethyl-3-(4-methylphenyl)-2-propenylidene]amino]oxy] methyl ester ((CA INDEX NAME) (CHEMCATS, RN 717838-82-9)) is commercially available from Rare Chemicals GmbH. An insecticidal activity is not mentioned for this compound.

WO 2006/125637 discloses oxime ether compounds of the formula

wherein is absent or a covalent bond, k is 0, 1 , 2, 3, or 4, Ar is an aromatic ring, R ^x is a radical different from hydrogen, R ^a is inter alia hydrogen alkyl or haloalkyl, R ^b is inter alia hydrogen, halogen, cyano, alkyl, R ^c is inter alia hydrogen, halogen, cyano, alkyl, R ^d is inter alia hydrogen, halogen, cyano, alkyl or together with R ^b forms a bivalent radical, R ^e is inter alia hydrogen, alkyl, haloalkyl, etc. and R ^f is a cyclic radical.

There is continuing need to provide compounds which are useful for combating arthropod pests such as insects and arachnids.

It is an object of the present invention to provide further compounds having a good activity against arthropod pests such as insects and/or arachnids and thus are useful for combating said pests.

The inventors of the present application surprisingly found that this object is achieved by compounds of formula I as defined below and by the agriculturally or veterinably acceptable salts thereof.

Therefore, the present invention relates to O-carboxymethyl oxime ether compounds of the formula I

and to the agriculturally or veterinarily acceptable salt thereof, wherein

is absent or a covalent bond;

k is 0, 1 , 2, 3 or 4;

Cy is a 5- or 6-membered carbocyclic radical or a heterocyclic radical with 1 , 2, 3 or 4 heteroatoms which are selected, independently of one another, from O, N and

S;

R ^a independently of one another, are selected from the group consisting of halogen, cyano, nitro, hydroxy, CrCio-alkyl, Ci-Cio-haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ - halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -halo- alkynyl, CrCi _θ -alkoxy, CrCi _θ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -haloalkenyl- oxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi _θ -alkylthio, CrCi _θ -haloalkyl- thio, CrCi _O -alkylsulfinyl, CrCi _θ -haloalkylsulfinyl, CrCi _θ -alkylsulfonyl, C ₁ -C ₁ 0- haloalkylsulfonyl, (d-Cio-alkylJcarbonyl, (d-Cio-haloalkylJcarbonyl, (CrCi ₀ - alkoxy)carbonyl, (Ci-Ci ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl,

(C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ⁷ R ⁸ , CO-NR ⁷ R ⁸ and phenoxy, which itself may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents R ^b , independently of one another selected from the group consisting of halogen, cyano, nitro, hydroxy, CrCi _O -alkyl, CrCi _θ -haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, C ₁ -C ₁₀ - alkoxy, CrCi _θ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -haloalkenyloxy, C ₂ -Ci ₀ - alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi _θ -alkylthio, CrCi _θ -haloalkylthio, C ₁ -C ₁ 0- alkylsulfinyl, CrCi _θ -haloalkylsulfinyl, CrCi _θ -alkylsulfonyl, CrCi _θ -haloalkyl- sulfonyl, (CrCi _θ -alkyl)carbonyl, (CrCi _θ -haloalkyl)carbonyl, (CrCi _θ -alkoxy)- carbonyl, (CrCi _θ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl, (C ₂ -Ci ₀ - haloalkenyloxy)carbonyl, NR ⁹ R ¹⁰ and CO-NR ⁹ R ¹⁰ ; in case that k is 2, 3 or 4, two vicinal radicals R ^a together may also be a bivalent radical, thereby forming a 5- to 7-membered fused heterocycle, containing at least 2 atoms of O, S and/or N, both bound to the cyclic radical Cy.

R ¹ is hydrogen, CrCi _O -alkyl, CrCi _θ -haloalkyl, CrCi _θ -cyanoalkyl, CrCi _θ -hydroxy- alkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl,

C ₃ -Cio-alkynyl, C ₂ -Cio-haloalkynyl, or an aromatic ring selected from phenyl, pyridyl, pyrimidyl, furyl, pyranyl, pyrrolyl and thienyl, wherein the last 7 radicals may be substituted by cyano, nitro, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, CrCi ₀ - alkylthio, CrCi ₀ -haloalkylthio, CrCi ₀ -alkylsulfonyl, CrCi ₀ -haloalkylsulfonyl, (Ci-Cio-alkylJcarbonyl, (CrCi ₀ -haloalkyl)carbonyl, (CrCi ₀ -alkoxy)carbonyl,

(CrCio-haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyl- oxy)carbonyl, NR ¹¹ R ¹² , -CO-NR ¹¹ R ¹² ;

R ² is hydrogen, halogen, cyano, CrCi _O -alkyl, CrCi ₀ -haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ - haloalkynyl, CrCi ₀ -alkoxy, CrCi ₀ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -halo- alkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi ₀ -alkylthio, CrCi ₀ - haloalkylthio, hydroxy-Ci-Ci _θ -alkyl, Ci-Ci _θ -alkoxy-Ci-Ci _θ -alkyl, CrCi ₀ -haloalkoxy- Ci-Cio-alkyl, (Ci-Ci _θ -alkoxy)carbonyl-Ci-Ci _θ -alkyl, (CrCi ₀ -haloalkoxy)carbonyl- Ci-Ci _O -alkyl or phenyl which may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents R ^c , independently of one another selected from the group consisting of halogen, cyano, nitro, hydroxy, CrCi _O -alkyl, CrCi ₀ -haloalkyl, C ₃ -Ci ₀ -cyclo- alkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, CrCi ₀ -alkoxy, CrCi ₀ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ - haloalkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi ₀ -alkylthio,

Ci-Ci ₀ -haloalkylthio, CrCi _O -alkylsulfinyl, CrCi ₀ -haloalkylsulfinyl, CrCi _O -alkyl- sulfonyl, CrCi ₀ -haloalkylsulfonyl, (CrCi ₀ -alkyl)carbonyl, (CrCi ₀ -haloalkyl)- carbonyl, (CrCi ₀ -alkoxy)carbonyl, (CrCi ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyl- oxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ¹³ R ¹⁴ Or -CO-R ¹³ R ¹⁴ ;

R ³ is hydrogen, halogen, cyano, CrCi _O -alkyl, CrCi ₀ -haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ - haloalkynyl, CrCi ₀ -alkoxy, CrCi ₀ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -halo- alkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi ₀ -alkylthio, CrCi ₀ - haloalkylthio, hydroxy-Ci-Ci _θ -alkyl, Ci-Ci _θ -alkoxy-Ci-Ci _θ -alkyl, Ci-Ci _θ -alkoxy-Cr

Ci _θ -haloalkyl, (Ci-Ci _θ -alkoxy)carbonyl-Ci-Ci _θ -alkyl, CrCi ₀ -haloalkoxycarbonyl- CrCi _O -alkyl or phenyl which may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents R ^d , independently of one another selected from the group consisting of halogen, cyano, nitro, hydroxy, CrCi _O -alkyl, CrCi ₀ -haloalkyl, C ₃ -Ci ₀ -cyclo- alkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl,

C ₃ -Ci ₀ -haloalkynyl, CrCi ₀ -alkoxy, CrCi ₀ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ - haloalkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi ₀ -alkylthio, CrCi ₀ -haloalkylthio, CrCi _O -alkylsulfinyl, CrCi ₀ -haloalkylsulfinyl, CrCi _O -alkyl- sulfonyl, CrCi ₀ -haloalkylsulfonyl, (Ci-Cio-alkylJcarbonyl, (CrCi ₀ -haloalkyl)- carbonyl, (CrCi ₀ -alkoxy)carbonyl, (Ci-Ci ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyl- oxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ¹⁵ R ¹⁶ Or CO-NR ¹⁵ R ¹⁶ ;

R ⁴ is hydrogen, halogen, cyano, nitro, hydroxy, CrCio-alkyl, Ci-Cio-haloalkyl, C ₃ -Cio-cycloalkyl, C ₃ -C ₁₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, Ci-Cio-alkoxy, CrCio-haloalkoxy, C ₂ -Ci ₀ - alkenyloxy, C ₂ -Ci ₀ -haloalkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy,

CrCi _θ -alkylthio, CrCi _θ -haloalkylthio, CrCi _O -alkylsulfinyl, CrCi _θ -haloalkylsulfinyl, CrCi _θ -alkylsulfonyl, CrCi ₀ -haloalkylsulfonyl, (Ci-Cio-alkylJcarbonyl, (CrCi _θ -halo- alkyl)carbonyl, (CrCi _θ -alkoxy)carbonyl, (Ci-Ci ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ - alkenyloxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ¹⁷ R ¹⁸ , CO-NR ¹⁷ R ¹⁸ or phenoxy which may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents R ^e , independently of one another selected from the group consisting of halogen, cyano, nitro, hydroxy, C _r Ci ₀ -alkyl, CrCi _θ -haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ - halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -halo- alkynyl, CrCi _θ -alkoxy, CrCi _θ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -haloalkenyl- oxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyloxy, CrCi _θ -alkylthio, CrCi _θ -haloalkyl- thio, Ci-Ci _θ -alkylsulfinyl, CrCi _θ -haloalkylsulfinyl, CrCi _θ -alkylsulfonyl, CrCi ₀ - haloalkylsulfonyl, (CrCi _θ -alkyl)carbonyl, (CrCi _θ -haloalkyl)carbonyl, (CrCi ₀ - alkoxy)carbonyl, (CrCi _θ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ¹⁹ R ²⁰ Or CO-NR ¹⁹ R ²⁰ ;

or if Cy is phenyl,

R ² and R ⁴ together can also form a bivalent radical Z, which is selected from -O-, -S-, -S(O)-, S(O) ₂ -, -N(R ^b1 )-, -O-C(O)-, -S-C(O)-, -0-CH(R ^b2 )-, -C(0)-N(R ^b3 )-, -C(S)-N(R ^b4 )-, -C(R ^b5 )=N-, -N(R ^b6 )-CH(R ^b7 )-, -S-CH(R ^b8 )-, -S(O)-CH(R ^b9 )-,

-S(O) ₂ -CH(R ^b10 )-, thereby forming a 5- or 6-membered heterocyclic ring which is fused to Cy, wherein R ^b1 , R ^b2 , R ^b3 , R ^b4 , R ^b5 , R ^b6 , R ^b7 , R ^b8 , R ^b9 and R ^b1 ° are selected, independently of one another, from the group consisting of hydrogen, Ci-Cio-alkyl, CrCi _θ -haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl,

CrCi _θ -alkylsulfonyl, C _r Ci ₀ -haloalkylsulfonyl, (Ci-Cio-alkylJcarbonyl, (Ci-Cio-haloalkylJcarbonyl, (CrCi _θ -alkoxy)carbonyl, (Ci-Ci ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, NR ²¹ R ²² and CO-NR ²¹ R ²² and wherein R ^b2 and R ^b5 may also be selected from halogen, cyano or nitro;

R ^5a is hydrogen, halogen, cyano, nitro, CrCi _O -alkyl, CrCi _θ -haloalkyl, (d-C ₄ -alkoxy)-

C _r C ₄ -alkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ - haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, CrCi _θ -alkoxy, CrCi _θ -haloalkoxy, C ₂ -Ci ₀ -alkenyloxy, C ₂ -Ci ₀ -haloalkenyloxy, C ₂ -Ci ₀ -alkynyloxy, C ₃ -Ci ₀ -haloalkynyl- oxy, CrCi _θ -alkylthio, C _r Ci ₀ -haloalkylthio, Ci-Cio-alkylcarbonyl, CrCi _θ -haloalkyl-

carbonyl, (d-Cio-alkoxy)carbonyl, (Ci-C-io-haloalkoxyJcarbonyl, Ci-Ci _θ -aryl- carbonyl, (C ₂ -Ci ₀ -alkenyloxy)carbonyl, (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl, (C ₁ -C ₁ 0- alkylcarbonyl)thiomethyl, (CrCio-alkylcarbonyOoxymethyl, NR ²³ R ²⁴ , CO-NR ²³ R ²⁴ , thienyl, furyl, pyridyl, phenyl, benzyl and phenoxy, wherein the aromatic ring of the 6 last mentionend radicals may be unsubstituted or may carry 1 , 2, 3, 4 or substituents R ^f which, independently of one another, are selected from the group consisting of halogen, cyano, nitro, CrCio-alkyl, Ci-Cio-haloalkyl;

R ^5b is hydrogen, halogen, CrC ₄ -alkyl or CrC ₄ -alkoxy; or

R ^5a and R ^5b together can also form a bivalent radical Y, which together with the attached carbon atom forms a 3 to 7 membered or 5 to 7 membered saturated carbocycle which may be unsubstituted or may carry 1 to 6 substituents R ⁹ which are selected, independently of one another, from the group consisting of halogen, Ci-Ci _O -alkyl, Ci-Cio-haloalkyl or Ci-Cio-alkoxy;

R ⁶ is hydrogen, Ci-Ci _O -alkyl, Ci-Cio-haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halo- cycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, Ci-C ₄ -alkoxy-Ci-Cio-alkyl, d-C-io-alkylcarbonyl, benzyl and hetaryl-Ci-C ₄ -alkyl wherein the aromatic ring of the 2 last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or substituents R ^h which, independently of one another, are selected from the group consisting of halogen, cyano, nitro, CrCio-alkyl, Ci-Cio-haloalkyl or Ci-Cio-alkoxy;

R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ and R ²⁴ , are selected, independently of one another, from the group consisting of hydrogen, CrCio-alkyl, Ci-Cio-haloalkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ - alkenyl, C ₂ -Ci ₀ -haloalkenyl, C ₂ -Ci ₀ -alkynyl, C ₃ -Ci ₀ -haloalkynyl, (CrCi _O -alkyl)- carbonyl, (Ci-Cio-haloalkylJcarbonyl, phenyl, phenylcarbonyl or benzyl, wherein the phenyl ring of the 3 aromatic radicals may be unsubstituted or may carry 1 , 2,

3, 4 or 5 substituents R', which, independently of one another, are selected from the group consisting of halogen, cyano, nitro, hydroxy, CrCi _O -alkyl, CrCi _θ -halo- alkyl, C ₃ -Ci ₀ -cycloalkyl, C ₃ -Ci ₀ -halocycloalkyl, C ₂ -Ci ₀ -alkenyl, C ₂ -Ci ₀ -haloalkenyl, CrCi _θ -alkoxy, CrCi _θ -haloalkoxy, CrCi _θ -alkylthio, CrCi _θ -haloalkylthio, C ₁ -C ₁ 0- alkylsulfonyl, C-i-C-io-haloalkylsulfonyl, (d-Cio-alkylJcarbonyl, (CrCi _θ -haloalkyl)- carbonyl, (CrCi _θ -alkoxy)carbonyl, (Ci-Ci ₀ -haloalkoxy)carbonyl, (C ₂ -Ci ₀ -alkenyl- oxy)carbonyl or (C ₂ -Ci ₀ -haloalkenyloxy)carbonyl;

except from the embodiment according to formula I, wherein the compound is acetic acid, [[[1 ,2-dimethyl-3-(4-methylphenyl)-2-propenylidene]amino]oxy], methyl ester (CA INDEX NAME) (CHEMCATS, RN 717838-82-9).

Due to their excellent activity, the compounds of the general formula I can be used for controlling arthropod pests, in particular pests, selected from harmful insects and arachnids. The compounds of the formula I are especially useful for combating insects.

The invention also relates to a method for combating arthropod pests which comprises contacting the arthropod pest, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the arthropod pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from arthropod attack or infestation, with a pesticidally effective amount of at least one O-carboxymethyl oxime ethers of formula I, as defined above.

The invention provides in particular a method for protecting crops, including seeds, from attack or infestation by arthropod pests, in particular harmful insects and/or arachnids, said method comprises contacting a crop with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof.

The invention also provides a method for protecting non-living materials from attack or infestation by the aforementioned pests, which method comprises contacting the non- living material with a pesticidally effective amount of at least one compound of formula I as defined herein or with a salt thereof.

The invention also provides a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of an oxime ether compound of formula I as defined herein, or a veterinarily acceptable salt thereof. The parasites are preferably selected from insects, in particular from the Diptera, Siphonaptera and Ixodida orders.

Accordingly, the invention further provides compositions for combating such pests, preferably in the form of directly sprayable solutions, emulsions, pastes, oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprises a pesticidally effective amount of at least one compound of the general formula I or at least a salt thereof and at least one carrier which may be liquid and/or solid and which is preferably agriculturally or veterinarily acceptable, and/or at least one surfactant.

Suitable compounds of the general formula I encompass all possible stereoisomers (cis/trans isomers, enantiomers) which may occur and mixtures thereof. Stereoisomeric centers are e.g. the carbon atom of the C(R ² )=C(R ³ ) group, the 0-N=C(R ¹ ) group and the CH(R ^5a )(R ^5b ) moiety. According to the present invention both the pure enantiomers or diastereomers or mixtures thereof, the pure cis- and trans-isomers and the mixtures

thereof can be used. The compounds of the general formula I may also exist in the form of different tautomers if R ⁶ or Cy carry amino or hydroxy groups. The invention comprises the single tautomers, if separable, as well as the tautomer mixtures.

Salts of the compounds of the formula I are preferably agriculturally or veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH ₄ ⁺ ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by CrC ₄ -alkyl, Ci-C ₄ -hydroxyalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -alkoxy-Ci- C ₄ -alkyl, hydroxy-Ci-C ₄ -alkoxy-CrC ₄ -alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C ₄ -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C ₄ -alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C ₄ -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae Ia and Ib with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term "veterinarily acceptable salts" is meant salts the anions of which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C _n -C _m indicates in each case the possible number of carbon atoms in the group.

"Halogen" will be taken to mean fluoro, chloro, bromo and iodo.

The term "Ci-Ci _O -alkyl" as used herein (and also in Ci-Cio-alkylcarbonyl, Ci-Cio-alkyl- sulfinyl and CrCio-alkylsulfonyl) refers to a branched or unbranched saturated hydrocarbon group having 1 to 10 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl,

2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C ₄ -alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1 ,1-dimethylethyl.

The term "Ci-Ci ₀ -haloalkyl" as used herein (and also in Ci-Cio-haloalkylsulfinyl and Ci-Cio-haloalkylsulfonyl) refers to a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example CrC ₄ -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term d-C-io-haloalkyl in particular comprises CrC ₂ -fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.

Similarly, "Ci-Cio-alkoxy" and "CrCio-alkylthio" refer to straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group. Examples include CrC ₄ - alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further CrC ₄ -alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

Accordingly, the terms "CrCio-haloalkoxy" and " Ci-Cio-haloalkylthio" refer to straight- chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example CrC ₂ -haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro- 2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, further Ci-C ₂ -haloalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1 -fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,

2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2, 2-dichloro-2 -fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like. Similarly the terms CrC ₂ - fluoroalkoxy and CrC ₂ -fluoroalkylthio refer to d-C ₂ -fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.

The term "C ₂ -Ci ₀ -alkenyl" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,

1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,

3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl-2-butenyl, 1 ,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl,

1 -ethyl-1 -methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1 -ethyl^-methyl^-propenyl.

The term "C ₂ -Cio-haloalkenyl" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.

Similarly, the term "C ₂ -Ci ₀ -alkenyloxy" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkages, respectively, at any bond in the alkenyl group, for example ethenyloxy, propenyloxy and the like.

Accordingly, the term "C ₂ -Cio-haloalkenyloxy" as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, the alkenyl group being bonded through oxygen linkages, respectively, at any bond in the alkenyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.

The term "C ₂ -Ci ₀ -alkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.

The term "C ₃ -Ci ₀ -haloalkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond.

The term "C ₂ -Cio-alkynyloxy" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, the alkynyl group being bonded through oxygen linkages at any bond in the alkynyl group.

Similarly, the term "C3-Cio-haloalkynyloxy" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 3 to 10 carbon atoms and containing at least one triple bond, the group being bonded through oxygen linkages at any bond in the alkynyl group, where some or all of the hydrogen atoms in this group may be replaced by halogen atoms as mentioned above, with the proviso that the halogen atom is not directly bound to the triple bond.

The term "C ₃ -Cio-cycloalkyl" as used herein refers to a monocyclic 3- to 10-membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.

The term "C ₃ -Ci ₀ -halocycloalkyl" as used herein refers to a monocyclic 3- to 10-membered saturated carbon atom ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloro-, dichloro- and trichlorocyclopropyl, fluoro-, difluoro- and trifluorocyclopropyl, chloro-, dichloro-, trichloro, tetrachloro-, pentachloro- and hexachlorocyclohexyl and the like.

The term "C _r Cio-alkylcarbonyl" as used herein refers to CrCio-alkyl which is bound to the remainder of the molecule via a carbonyl group. Examples include CO-CH ₃ , CO-C ₂ H ₅ , CO-CH ₂ -C ₂ H ₅ , CO-CH(CH ₃ ) ₂ , n-butylcarbonyl, CO-CH(CH ₃ )-C ₂ H ₅ , CO-CH ₂ -CH(CH ₃ ) ₂ , CO-C(CH ₃ ) ₃ , n-pentylcarbonyl, 1 -methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1 -ethylpropylcarbonyl, n-hexylcarbonyl, 1 ,1-dimethylpropylcarbonyl, 1 ,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1 ,1-dimethylbutylcarbonyl, 1 ,2-dimethylbutylcarbonyl, 1 ,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1 ,1 ,2-trimethylpropylcarbonyl, 1 ,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1 -ethyl-2-methylpropylcarbonyl.

The term "CrCio-alkoxycarbonyl" as used herein refers to CrCio-alkoxy which is bound to the remainder of the molecule via a carbonyl group. Examples include CO-OCH ₃ , CO-OC ₂ H ₅ , CO-OCH ₂ -C ₂ H ₅ , CO-OCH(CH ₃ ) ₂ , n-butoxycarbonyl, CO-OCH(CH ₃ )-C ₂ H ₅ , CO-OCH ₂ -CH(CH ₃ ) ₂ , CO-OC(CH ₃ ) ₃ , n-pentoxycarbonyl, 1 -methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -ethylpropoxycarbonyl, n-hexoxycarbonyl, 1 ,1-dimethylpropoxycarbonyl, 1 ,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,

1 ,1-dimethylbutoxycarbonyl, 1 ,2-dimethylbutoxycarbonyl, 1 ,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1 ,1 ,2-trimethylpropoxycarbonyl, 1 ,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1 -ethyl-2-methylpropoxycarbonyl.

The term "halo-Ci-C-io-alkoxycarbonyl" as used herein refers to CrCio-haloalkoxy which is bound to the remainder of the molecule via a carbonyl group.

The terms "hydroxy-C _r Cio-alkyl", "CrC-io-alkoxy-Ci-C-io-alkyl", "halo-Ci-Cio-alkoxy-C _r Cio-alkyl", "Crdo-alkoxycarbonyl-Ci-Cio-alkyl", "halo-Ci-Cio-alkoxycarbonyl-Ci-Ci ₀ - alkyl" as used herein, refer to Ci-Ci _O -alkyl, as defined herein, in particular to methyl, ethyl, 1 -propyl or 2-propyl, which is substituted by one radical selected from hydroxy, Ci-Cio-alkoxy, C ₁ -C ₁ 0- haloalkoxy, CrCio-alkoxycarbonyl or d-Cio-haloalkoxycarbonyl.

The term "5- or 6-membered heterocyclic radical with 1 , 2, 3 or 4 heteroatoms which are selected, independently of one another, from O, N and S " comprises monocyclic 5- or 6-membered heteroaromatic rings and nonaromatic saturated or partially unsaturated 5- or 6-membered mono-heterocycles, which carry 1 , 2, 3, or 4 heteroatoms as ring members. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.

Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1 ,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like.

Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl.

With respect to the use according to the invention of the compounds of formula I, particular preference is given to the following meanings of the substituents, in each case on their own or in combination:

R ¹ is preferably hydrogen, Ci-Ci _O -alkyl, Ci-Ci ₀ -haloalkyl, more preferably hydrogen, CrC ₄ -alkyl or CrC ₄ -haloalkyl, and especially hydrogen. However, preference is also given to compounds I, wherein R ¹ is aryl or hetaryl, in particular phenyl or pyridyl.

R ² is preferably selected from hydrogen, halogen, cyano and Ci-C ₄ -alkyl, in particular from hydrogen, fluorine, chlorine, bromine, cyano, methyl or ethyl. In one embodiment R ² is different from cyano.

R ³ is preferably selected from hydrogen, halogen, Ci-C ₄ -alkyl and CrC ₄ -haloalkyl, with hydrogen being more preferred.

R ^5a is preferably selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-alkoxy, CrCio-alkylthio, halogen, (Ci-C ₄ -alkoxy)methyl, (CrCio-carbonyl)thiomethyl, arylcarbonyl and phenyl in particular from hydrogen and CrC ₄ -alkyl.

R ^5b is preferably selected independently of R ^5a from hydrogen, Ci-Cio-alkyl, d-C-io- alkoxy and halogen in particular from hydrogen and CrC ₄ -alkyl.

R ^5a and R ^5b together with the carbon atom, to which they are bound, may also form a 3- to 7-membered or 5- to 7-memberred saturated carbocycle, such as a cyclopropane, cyclopentane or cyclohexane radical.

Preference is given to compounds of formula I, wherein R ⁶ in formula I is CrCio-alkyl, C ₃ -Ci ₀ -cycloalkyl, C ₂ -Ci ₀ -alkenyl, Ci-Ci ₀ -alkoxy-Ci-C ₃ -alkyl or benzyl.

Cy is preferably cyclohexenyl, tetrahydropyranyl, furanyl, pyridyl, thiophenyl, N-substituted pyrrolyl, isoxazolyl or phenyl, which are unsubstituted or substituted by 1 , 2, 3 or 4 radicals R ^a as defined above.

In particular preference is given to phenyl, which is unsubstituted or substituted by 1 , 2 or 3 radicals R ^a as defined above, depending on the number k. A skilled person will appreciate that in case of R ⁴ being different from hydrogen, the total number of radicals on phenyl is k+1 , or, if R ⁴ together with R ² is the aforementioned bivalent radical, the total number of substituents on phenyl is k.

Preferably the radicals R ^a (and likewise R ⁴ ) are selected, independently of one another, from halogen, CN, d-C ₄ -alkyl, CrC ₄ -alkoxy, CrC ₄ -haloalkoxy and CrC ₄ -haloalkyl, more preferably F, Cl, CN, CrC ₃ -alkoxy, in particular methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy and methyl.

In a preferred embodiment of the invention the radical R ² and R ⁴ in formula I are monovalent radicals, i.e. R ² and R ⁴ together do not form a bivalent radical. In this embodiment R ² is preferably selected from hydrogen, halogen, Ci-C ₄ -alkyl, CrC ₄ - alkoxy, CrC ₄ -haloalkoxy and CrC ₄ -haloalkyl. More preferably R ² is hydrogen, fluorine, chlorine bromine, methyl or ethyl. Most preferably R ² is hydrogen or methyl. In this embodiment R ⁴ is hydrogen or a radical R ^a as defined above, in particular hydrogen. In this embodiment Cy in formula I is preferably phenyl, which is unsubstituted or substituted by 1 , 2, 3 or 4, in particular 1 , 2 or 3 radicals R ^a as defined above.

Another embodiment of the invention relates to compounds of the formula I, wherein R ⁴ together with R ² is a bivalent radical Y as defined above and which is preferably selected from O, S, N(R ^b1 ), CH=N, 0-CH ₂ , O-C(O) or NH-C(O), where in the last 4 moieties either the carbon atom or the heteroatom is attached to the phenyl ring, in particular from O, S, 0-CH ₂ and O-C(O), where in the last 2 moieties the heteroatom is attached to the phenyl ring. More preferably R ⁴ and R ² together are an oxygen atom or O-C(O), in particular O. In this embodiment Cy in formula I is phenyl, which is unsubstituted or substituted by 1 , 2 or 3, in particular 0, 1 or 2 radicals R ^a as defined above.

Apart from that, R ^b1 , R ^b2 , R ^b3 , R ^b4 and R ^b5 , if present, are preferably selected from hydrogen, Ci-C ₄ -alkyl and Ci-C ₄ -haloalkyl it is being possible that R ^b2 and R ^b5 may also be selected from halogen.

If present, R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ and R ²⁴ are preferably selected independently from one another from hydrogen and Ci-C ₄ -alkyl.

If present, R ^b and R ^c are preferably selected, independently from another, from halogen, C _r C ₄ -alkyl, CN, NO ₂ , OH, C _r C ₄ -haloalkyl, C _r C ₄ -alkoxy and C _r C ₄ - haloalkoxy.

A very preferred embodiment of the invention relates to compounds of the general formula Ia:

wherein k is O, 1 , 2 or 3, and wherein Cy, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^a are as defined above.

Examples of compounds Ia are given in the following tables 1 to 378.

Table 1

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 2

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is F and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 3

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 4

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 5

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 6

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 7

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 8

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 9

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 10

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 11

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluoro-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 12

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 13

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 14

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is OCH ₃ and Cy-

(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 15

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 16

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 17

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is CH ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 18

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 19

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is CF ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 20

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 21

Compounds of the formula Ia in which R ¹ is H, R ² is H, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 22

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 23

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is F and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 24

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 25

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 26

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 27

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 28

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 29

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is 3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 30

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 31

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 32

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluoro-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 33

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 34

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 35

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 36

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 37

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A

Table 38

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is CH ₃ and Cy-

(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 39

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 40

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is CF ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 41

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 42

Compounds of the formula Ia in which R ¹ is H, R ² is CN, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 43

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 44

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is F and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 45

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 46

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 47

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is Cl and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 48

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 49

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 50

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is Cl and

Cy-(R ^a ) _k is 3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 51

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 52

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 53

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 4-fluoro-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 54

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 55

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 56

Compounds of the formula Ia in which R ¹ is H, R ² is methyl H, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 57

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 58

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 59

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is CH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 60

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is 3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 61

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is CF ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 62

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 63

Compounds of the formula Ia in which R ¹ is H, R ² is methyl, R ³ is H, R ⁴ is H and

Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 64

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 65

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is F and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 66

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 67

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 68

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 69

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 70

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 71

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is 3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 72

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 73

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 74

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 4-fluoro-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 75

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 76

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 77

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl H, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 78

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 79

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 80

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is CH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 81

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is 3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 82

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is CF ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 83

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 84

Compounds of the formula Ia in which R ¹ is H, R ² is ethyl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 85

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 86

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is F and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 87

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 88

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 89

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 90

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 91

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 92

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 93

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 94

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 95

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluoro-3-trifluoromethylphenyl and the combination of R ⁵ and R ⁶ for a compound corresponds in each case to one row of table A.

Table 96

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 97

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 98

Compounds of the formula Ia in which R ¹ is H, R ² is Cl H, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 99

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 100

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 101

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is CH ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 102

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 103

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is CF ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 104

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 105

Compounds of the formula Ia in which R ¹ is H, R ² is Cl, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ⁵ and R ⁶ for a compound corresponds in each case to one row of table A.

Table 106

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is phenyl and the combination R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 107

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is F and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 108

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 109

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 110

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 11 1

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 112

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 113

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is Cl and Cy-(R ^a ) _k is

3-chlorophenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 114

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-difluoromethoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 115

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 116

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-fluoro-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 117

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methoxy-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 118

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

4-methylthio-3-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 119

Compounds of the formula Ia in which R ¹ is H, R ² is Br H, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 120

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 3-methoxyphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 121

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is OCH ₃ and

Cy-(R ^a ) _k is 4-trifluoromethylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 122

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is CH ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 123

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is

3-methylphenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 124

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is CF ₃ and Cy-(R ^a ) _k is phenyl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 125

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is fur-2-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 126

Compounds of the formula Ia in which R ¹ is H, R ² is Br, R ³ is H, R ⁴ is H and Cy-(R ^a ) _k is pyrid-3-yl and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Tables 127 to 252

Compounds of the formula Ia in which R ² , R ³ , R ⁴ and Cy-(R ^a ) _k are as defined in one of the tables 1 to 126, and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A and R ¹ is methyl instead of hydrogen.

Tables 253 to 378

Compounds of the formula Ia in which R ² , R ³ , R ⁴ and Cy-(R ^a ) _k are as defined in one of the tables 1 to 126, and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A and R ¹ is ethyl instead of hydrogen.

Table A:

Another very preferred embodiment of the invention relates to compounds of the general formula Ib:

wherein k is 0, 1 , 2 or 3, and wherein R ¹ , R ³ , R ⁵ , R ^5a , R ^5b , R ⁶ and R ^a are as defined above and Z is as defined above. Amongst the compounds Ib those are preferred, wherein Z is O, S, OC(O) or OCH ₂ and wherein R ¹ , R ³ , R ^a and k have the meanings given as preferred.

Examples of compounds Ib are given in the following tables 379 to 402:

Table 379 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is O, (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 380 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is O, (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 381 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is O, (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 382 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is S, (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 383 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is S, (R ^a ) _k is 5-CH ₃ and the

combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 384 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is S, (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 385 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OC(O), (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 386 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OC(O), (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 387 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OC(O), (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 388 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OCH ₂ , (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 389 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OCH ₂ , (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 390 Compounds of the formula Ib in which R ¹ is H, R ³ is H, Z is OCH ₂ , (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 391 Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is O, (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of

table A.

Table 392

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is O, (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 393

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is O, (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 394

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is S, (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 395

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is S, (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 396

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is S, (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 397

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OC(O), (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 398

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OC(O), (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 399

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OC(O), (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 400

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OCH ₂ , (R ^a ) _k is H and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 401

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OCH ₂ , (R ^a ) _k is 5-CH ₃ and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

Table 402

Compounds of the formula Ib in which R ¹ is CH ₃ , R ³ is H, Z is OCH ₂ , (R ^a ) _k is 5-CI and the combination of R ^5a , R ^5b and R ⁶ for a compound corresponds in each case to one row of table A.

The compounds of the formula I may be readily synthesized using standard techniques well known in the art of organic chemistry.

The compounds of formula I can be obtained for example by analogy to the methods described in WO 00/031024 or EP 579124. For instance, suitable O-alkylated hydroxylamines of the formula Il or their corresponding ammonium salts can be reacted with aldehydes or ketones of the formula III to obtain the compounds of the formula I (Scheme 1 ).

Scheme 1 :

I

O-alkylated hydroxylamines of the formula Il and their corresponding ammonium salts can be prepared by analogy to the methods described e.g. in DE 3615473 or WO 95/04032 or in references cited therein.

Alternatively, compounds of the general formula I can be prepared by applying the synthesis method depicted in scheme 2. This method comprises reacting aldehydes or ketones of the formula III with hydroxylamine or its ammonium salts to form oximes IV

which can be subsequently alkylated according to standard methods with compounds V to yield the compounds of the general formula I. In scheme 2 "L" is a conventional leaving group which can be replaced by O-nucleophiles, e.g. halogen, such as chlorine, bromine or iodine, (halo)alkylsulfonyloxy, such as methylsulfonyloxy (mesylat) or trifluormethylsulfonyloxy or arylsulfonyloxy such as benzenesulfonyloxy or toluenesulfonyloxy (tosylate).

Scheme 2:

III IV

If individual compounds I can not be prepared by the routes described in schemes 1 and 2, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described. The preparation of the compounds of formula I may lead to them being obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.

If not commercially available, aldehydes or ketones III can be obtained according to standard methods of organic synthesis, e.g. starting from benzaldehydes or heteroaromatic aldehydes and aliphatic ketones or aldehydes (Organikum, Johann Ambrosius Barth Verlag, Heidelberg, 1996, pp. 493-495).

The compounds of the formula I and their salts are in particular suitable for efficiently controlling arthropodal pests such as arachnids and insects.

In particular, they are suitable for controlling insect pests, such as

Insects from the order of Lepidoptera, for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, HeIIuIa undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera eridania, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,

from the order of Coleoptera (beetles), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, lps typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popilliajaponica, Sitona lineatus and Sitophilus granaria,

from the order of Diptera, for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae,

Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa,

from the order of Thysanoptera (thrips), e.g. Dichromothrips spp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

from the order of Hymenoptera e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,

from the order of Heteroptera, e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,

from the order of Homoptera, e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mail, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii,

from the order of lsoptera (termites), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis, and

from the order of Orthoptera, e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus

bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus.

The compounds of the formula I and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians {Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.

Compounds of the formula I are particularly useful for controlling insects of the orders Lepidoptera, Coleoptera, Diptera and Homoptera.

For use in a method according to the present invention, the compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries, which are suitable, are essentially:

water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used. carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers,

alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following are examples of formulations: 1. Products for dilution with water

A Soluble concentrates (SL)

10 parts by weight of a compound according to the invention are dissolved in water or in a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active ingredient dissolves upon dilution with water.

B Dispersible concentrates (DC)

20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.

C Emulsifiable concentrates (EC)

15 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). Dilution with water gives an emulsion.

D Emulsions (EW, EO)

40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). This mixture is introduced into water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.

E Suspensions (SC, OD) In an agitated ball mill, 20 parts by weight of a compound according to the invention are milled with addition of dispersant, wetters and water or an organic solvent to give a fine active ingredient suspension. Dilution with water gives a stable suspension of the active ingredient.

F Water-dispersible granules and water-soluble granules (WG, SG)

50 parts by weight of a compound according to the invention are ground finely with addition of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active ingredient.

G Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor- stator mill with addition of dispersant, wetters and silica gel. Dilution with water gives a stable dispersion or solution with the active ingredient.

2. Products to be applied undiluted

H Dustable powders (DP)

5 parts by weight of a compound according to the invention are ground finely and mixed intimately with 95% of finely divided kaolin. This gives a dustable product.

I Granules (GR, FG, GG, MG)

0.5 parts by weight of a compound according to the invention is ground finely and associated with 95.5% carriers. Current methods are extrusion, spray drying or the fluidized bed. This gives granules to be applied undiluted.

J ULV solutions (UL)

10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example xylene. This gives a product to be applied undiluted.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active ingredients according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.

The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.

In the method of this invention compounds I may be applied with other active ingredients, for example with other pesticides, insecticides, herbicides, fertilizers such

as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, but not to impose any limitation:

The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, but not to impose any limitation:

A.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos- methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate, heptenophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

A.2. Carbamates: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate;

A.3. Pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-, yfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, permethrin, phenothrin, prallethrin, resmethrin, RU 15525, silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin, ZXI 8901 ;

A.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen;

A.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium, and AKD1022.

A.6. GABA gated chloride channel antagonist compounds: chlordane, endosulfan, gamma-HCH (lindane); acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole, the phenylpyrazole compound of formula r ¹

A.7. Chloride channel activators: abamectin, emamectin benzoate, milbemectin, lepimectin;

A.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;

A.9. METI Il and III compounds: acequinocyl, fluacyprim, hydramethylnon;

A.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;

A.1 1. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon;

A.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

A.13. Synergists: piperonyl butoxide, tribufos;

A.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;

A.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;

A.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;

A.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;

A.18. Chitin synthesis inhibitors: buprofezin, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

A.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;

A.20. octapaminergic agonsits: amitraz;

A.21. ryanodine receptor modulators: flubendiamide;

A.22. Various: aluminium phosphide, amidoflumet, benclothiaz, benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate, phosphine, pyridalyl, pyrifluquinazon, sulfur, tartar emetic;

A.23. N-R'-2,2-dihalo-1-R"cyclo-propanecarboxamide-2-(2,6-dichloro -α,α,α-tri-fluoro-p- tolyl)hydrazone or N-R'-2,2-di(R'")propionamide-2-(2,6-dichloro-α,α,α-triflu oro-p-tolyl)- hydrazone, wherein R' is methyl or ethyl, halo is chloro or bromo, R" is hydrogen or methyl and R'" is methyl or ethyl;

A.24. Anthranilamides: chloranthraniliprole, the compound of formula F ²

A.25. Malononitrile compounds: CF ₃ (CH ₂ ) ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, CF ₃ (CH ₂ ) ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₅ CF ₂ H, CF ₃ (CH ₂ ) ₂ C(CN) ₂ (CH ₂ ) ₂ C(CF ₃ ) ₂ F, CF ₃ (CH ₂ ) ₂ C(CN) ₂ (CH ₂ ) ₂ (CF ₂ ) ₃ CF ₃ , CF ₂ H(CF ₂ ) _S CH ₂ C(CN) ₂ CH ₂ (CF ₂ ) _S CF ₂ H, CF ₃ (CH ₂ ) ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₃ , CF ₃ (CF ₂ ) ₂ CH ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, CF ₃ CF ₂ CH ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4- pentafluorobutyl)-malonodinitrile, and CF ₂ HCF ₂ CF ₂ CF ₂ CH ₂ C(CN) ₂ CH ₂ CH ₂ CF ₂ CF ₃ ;

A.26. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis;

The commercially available compounds of the group A may be found in The Pesticide Manual, 13 ^th Edition, British Crop Protection Council (2003) among other publications.

Thioamides of formula r ¹ and their preparation have been described in WO 98/28279. Lepimectin is known from Agro Project, PJB Publications Ltd, November 2004.

Benclothiaz and its preparation have been described in EP-A1 454 621. Methidathion and Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Acetoprole and its preparation have been described in WO 98/28277. Metaflumizone and its preparation have been described in EP-A1 462 456. Flupyrazofos has been described in Pesticide Science 54, 1988, p.237-243 and in US 4822779. Pyrafluprole and its preparation have been described in JP 2002193709 and in WO 01/00614. Pyriprole and its preparation have been described in WO 98/45274 and in US 6335357. Amidoflumet and its preparation have been described in US 6221890 and in JP 21010907. Flufenerim and its preparation have been described in WO 03/007717 and in WO 03/007718. AKD

1022 and its preparation have been described in US 6300348. Chloranthraniliprole has been described in WO 01/70671 , WO 03/015519 and WO 05/118552. Anthranilamide derivatives of formula r ² have been described in WO 01/70671 , WO 04/067528 and WO 05/118552. Cyflumetofen and its preparation have been described in WO 04/080180. The aminoquinazolinone compound pyrifluquinazon has been described in EP A 1 097 932. The malononitrile compounds CF ₃ (CH ₂ ) ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, CF ₃ (CH ₂ ) ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₅ CF ₂ H, CF ₃ (CH2)2C(CN)2(CH2)2C(CF3) ₂ F, CF3(CH2)2C(CN)2(CH2)2(CF ₂ )3CF3, CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF ₂ H, CF ₃ (CH2)2C(CN)2CH2(CF2)3CF ₃ , CF ₃ (CF ₂ ) ₂ CH ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, CF ₃ CF ₂ CH ₂ C(CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H, 2-

(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorob utyl)-malonodinitrile, and CF ₂ HCF ₂ CF ₂ CF ₂ CH ₂ C(CN) ₂ CH ₂ CH ₂ CF ₂ CF ₃ have been described in WO 05/63694.

The aforementioned compositions are particularly useful for protecting plants against infestation of said pests or to combat these pests in infested plants.

However, the compounds of formula I are also suitable for the treatment of seeds. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.

Compositions which are useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG) G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Dustable powders (DP, DS)

Preferred FS formulations of compounds of formula I for seed treatment usually comprise from 0.5 to 80% of the active ingredient, from 0.05 to 5 % of a wetter, from 0.5 to 15 % of a dispersing agent, from 0.1 to 5 % of a thickener, from 5 to 20 % of an anti-freeze agent, from 0.1 to 2 % of an anti-foam agent, from 1 to 20 % of a pigment and/or a dye, from 0 to 15 % of a sticker /adhesion agent, from 0 to 75 % of a filler/vehicle, and from 0.01 to 1 % of a preservative.

Suitable pigments or dyes for seed treatment formulations are pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Stickers / adhesion agents are added to improve the adhesion of the active materials on the seeds after treatment. Suitable adhesives are block copolymers EO/PO surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers and copolymers derived from these polymers.

For use against ants, termites, wasps, flies, mosquitos, crickets, or cockroaches, compounds of formula I are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.

The bait employed in the composition is a product which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or

cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

Formulations of compounds of formula I as aerosols (e.g. in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used.

The compounds of formula I and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

The compounds of formula I and its compositions can be used for protecting non-living material, in particular cellulose-based materials such as wooden materials e.g. trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of formula I are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also

be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

In the methods according to the invention the pests are controlled by contacting the target parasite/pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I or with a salt thereof or with a composition, containing a pesticidally effective amount of a compound of formula I or a salt thereof.

"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).

For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

In the treatment of seed, the application rates of the mixture are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of seed.

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m ² , preferably from 0.001 to 2O g per 100 m ² .

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m ² treated material, desirably from 0.1 g to 50 g per m

lnsecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and / or insecticide.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.

For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

Compounds of formula I and compositions comprising them may also be used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Compounds of formula I and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of formula I and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active

against all or some stages of development. The compounds of formula I are especially useful for combating ectoparasites.

The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.

The compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of the compounds of formula I and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of formula I and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of formula I and compositions containing them for combating fleas is especially preferred.

The use of the compounds of formula I and compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The compounds of formula I also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills,

solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.

The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

- Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of

the injection solutions with sufficient thickener that a clear material having an ointment- like consistency results. The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as N-methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene- 1 ,3-dioxolane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are:

liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C ₈ -Ci ₂ or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C ₈ -Ci ₀ fatty acids, - fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length Ci ₆ -Ci ₈ , isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length Ci ₂ -Ci ₈ , isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and - fatty acids such as oleic acid and mixtures thereof.

Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are:

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of formula I.

Generally it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day , preferably 1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.

Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.

Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I them are applied dermally / topically.

In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.

The active compounds can also be used as a mixture with synergists or with other active compounds which act against pathogenic endo- and ectoparasites.

In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis,

death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The present invention is now illustrated in further detail by the following examples.

I Preparation examples of compounds I

The products were characterized by coupled High Performance Liquid Chromatography / mass spectrometry (HPLC/MS), by NMR or by their melting points. HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % (TFA) in a ratio of from 5:95 to 95:5 within 5 minutes at 40°C. MS: Quadrupol electrospray ionisation, 80 V (positiv modus)

In the examples the following abbreviations are used: RT: retention time

DMF: dimethylformamide

Example 1 : (2-methyl-3-phenyl-allylideneaminooxy)-acetic acid 2-methoxy-ethyl ester (compound A12 of the following table)

a) Preparation of 2-methyl-3-phenyl-propenal oxime

A mixture of 2-methyl-3-phenyl-propenal (2.92 g, 20 mmol) and hydroxylamine hydrochlorid (1.39 g, 20 mmol) in methanol (2OmL) and triethylamine (2.77 mL, 20 mmol) was heated to reflux for 3 hours. After cooling to room temperature and evaporation of the solvent under reduced pressure the crude product was dissolved in dichloromethane (200 mL) and extracted with an acetic acid/sodium acetate buffer (pH 4.65, 75 mL) and subsequently with water (75 mL). The solution was dried over magnesium sulfate. After evaporation of the solvent the desired product (17.5 mmol, 2.82 g, 88%) was obtained. The compound was sufficiently pure for subsequent reactions (> 95% according to HPLC/MS; RT = 2.885 min, m/z = 162 [M+H] ⁺ ).

b) Preparation of (2-methyl-3-phenyl-allylideneaminooxy)-acetic acid 2-methoxy-ethyl ester

A mixture of 2-methyl-3-phenyl-3-yl-propenal oxime (0.5 mmol, 81 mg), chloro-acetic acid 2-methoxy-ethyl ester (0.5 mmol, 76 mg) and cesium carbonate (0.5 mmol,

163 mg) in DMF (2.5 mL) was heated to 50°C for 25 min in a microwave oven (max.

250 W). After cooling to room temperature the mixture was filtered through Celite and concentrated in vacuo. The crude product was dissolved in dichloromethane (4 ml_), washed twice with water (2 x 4 ml.) and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure the desired product was obtained (0.38 mmol, 105 mg, 76%, RT = 2.439 min, m/z = 253 [M+H] ⁺ ).

Likewise compounds A1 to A210, B1 to B38 and C1 to C47 given in following tables were prepared.

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The action of the compounds of the formula I against arthropod pests was demonstrated by the following experiments:

Il Activity against insects

11.1 Activity against Boll weevil (Anthonomus grandis)

The active compounds were formulated in DMSO : water (1 : 3). 10 to 15 eggs were placed into microtiterplates filled with 2% agar-agar in water and 300 ppm formaline. The eggs were sprayed with 20 μl of the test solution, the plates were sealed with pierced foils and kept at 24-26°C and 75-85 % humidity with a day/night cycle for 3 to 5 days. Mortality was assessed on the basis of the remaining unhatched eggs or larvae on the agar surface and/or quantity and depth of the digging channels caused by the hatched larvae. Tests were replicated 2 times.

In this test, the compounds A7, A13, A15, A17, A19-A22, A39, A53, A55, A63, A82, A99, A104, A105, A107, A109-A112, A132, A133, A140, A141 , A144, A189, A203- A208, B25, B29, B30, B36, B38, C1 , C16, C42 and C43 at a concentration of the test solution of 2500 mg/L showed a mortality of at least 50%.

11.2 Activity against Vetch aphid (Megoura viciae)

The active compounds were formulated in DMSO : water (1 : 3). Bean leaf disks were placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf disks were sprayed with 2.5 μl of the test solution and 5 to 8 adult aphids were placed into the microtiterplates which were then closed and kept at 22-24°C and 35 - 45% under fluorescent light for 6 days. Mortality was assessed on the basis of vital, reproduced aphids. Tests were replicated 2 times.

In this test, the compounds A13, A23, A36, A40, A77, A84, A85, A90, A104-A112, A124, A126-A129, A132, A133, A140, A141 , A144, A146-A148, A189, A193, A199, A200, A203, A204, A208, B3, B26, B29-B31 , B34, B35, C3, C15-C20, C22, C24, C33, C42 and C43 at a concentration of the test solution of 2500 mg/L showed a mortality of at least 50%.