Pesticide benzyloxy- and phenetyl-substituted phenyl-amidine derivatives

1. An phenyl-amidine derivative of formula (I):

wherein

X═O or CH 2 ;

R 1 represents H, a substituted or non substituted C 1 -C 12 -alkyl, a substituted or non substituted C 2 -C 12 -alkenyl, a substituted or non substituted C 2 -C 12 -alkynyl, SH or a substituted or non substituted S—C 1 -C 12 -alkyl ;

R 2 represents a substituted or non substituted C 1 -C 12 -alkyl;

R 3 represents a substituted or non substituted C 2 -C 12 -alkyl, substituted or non substituted C 3 -C 6 -cycloalkyl, substituted or non substituted C 2 -C 12 -alkenyl, substituted or non substituted C 2 -C 12 -alkynyl, halogeno- C 1 -C 12 -alkyl; or

R 1 and R 2 , R 1 and R 3 or R 2 and R 3 can form together a substituted or non substituted 5 to 7-membered heterocycle ;

R 4 represents a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl , substituted or non substituted O—C 1 -C 12 -alkyl or cyano;

R 5 represents a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano;

R 6 represents H, a substituted or non substituted C 1 -C 6 -alkyl, a halogen atom or halogeno-C 1 -C 6 -alkyl;

m represents 0, 1, 2, 3, 4 or 5;

R 7 , which may the same or different, represents H, a halogen atom, nitro, cyano, trialkylsilyl, C 1 -C 8 -alkyl, substituted or non-substituted C 1 -C 4 -alkyl-phenyl, substituted or non-substituted phenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 8 -alkylthio, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -halogenalkoxy or C 1 -C 6 -halogenoalkylthio, substituted or non substituted C 1 -C4-alkoxy-phenyl like benzyloxy, substituted or non substituted phenoxy, substituted, non substituted alkylamino-C 1 -C 8 —NR 5 R 9 , substituted or non substituted NR 8 R 9 , C 1 -C 8 -alkyl-S(O) n —R 10 , —S(O) n R 10 , C 1 -C 8 -alkyl-SO 2 NR 8 R 9 , —SO 2 NR 9 R 10 , alkyl-C(O)R 11 , —CR 10 ═N—O—R 12 ;

two substituents R 7 can form a carbocyclic or heterocyclic ring, which may comprise one or more heteroatoms selected in the list consisting of O, N, S;

n represents 0, 1 or 2;

R 8 and R 9 , which may the same or different, represent H, substituted or non-substituted C 1 -C 6 -alkyl;

R 8 and R 9 can form a heterocyclic ring, which may comprise one or more heteroatoms selected in the list consisting of O, N, S;

R 10 represents H, substituted or non-substituted, linear or branched C 1 -C 8 -alkyl, alkenyl, C 1 -C 8 -alkinyl;

R 11 represents H, substituted or non-substituted, linear or branched C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, NR 8 R 9 ;

R 12 represents H, substituted or non-substituted, linear or branched C 1 -C 8 -alkyl, alkyl-phenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, substituted or non-substituted C 1 -C 4 -alkyl-phenyl, substituted or non-substituted phenyl;

R 10 and R 12 can form a heterocyclic ring, which may comprise one or more heteroatoms selected in the list consisting of O, N, S;

as well as salts and optically active or geometric isomers thereof.

2. A compound of formula (I) according to claim 1 wherein

R 1 represents H, C 1 -C 12 -alkyl or SH; or

R 2 represents methyl; or

R 3 represents C 2 -C 12 -alkyl, C 2 -C 12 -alkenyl; C 3 -C 6 -cycloalkyl; or

R 2 and R 3 can form together a substituted or non substituted 5- to 7-membered heterocycle; or

R 4 represents C 1 -C 12 -alkyl, a halogen atom or trifluoromethyl; or

R 5 represents C 1 -C 12 -alkyl, a halogen atom or trifluoromethyl or

R 6 represents H or a non substituted C 1 -C 6 -alkyl; or

m represents 1, 2, 3 or 4; or

R 7 , which may be the same or different, represents H; F, Cl, Br, I; nitro; cyano C 1 -C 6 -alkyl; C 1 -C 4 -alkyl-phenyl which may be non substituted or substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -halogenoalkyl; phenyl which may be non substituted or substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -halogenoalkyl; C 1 -C 6 -alkoxy; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;

C 1 -C 6 -alkylthio; C 1 -C 6 -halogenoalkyl; C 1 -C 6 -halogenalkoxy C 1 -C 6 -halogenoalkylthio; C 1 -C 6 -alkoxy; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; C 1 -C 6 -alkylthio benzyloxy which may be non substituted or substituted by halogen; phenoxy which may be non substituted or substituted by a halogen atom or CF 3 ; NR 8 R 9 ; C 1 -C 4 -alkyl-NR 8 R 9 ; S(O) n R 10 ; C 1 -C 4 -alkyl-S(O) n R 10 ; OR 11 ; C 1 -C 4 -alkyl-COR 11 ; —CR 11 ; —R 10 ═N—O—R 12 ; or

R 8 and R 9 , which may be the same or different, represent H or C 1 -C 6 alkyl; or

R 8 and R 9 can form a heterocyclic ring comprising further heteroatoms selected from the group consisting of O, S and N; or

R 10 represents H, methyl or ethyl; or

R 11 represents H, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or NR 8 R 9 ; or

R 12 represents H; C 1 -C 4 -alkyl; C 1 -C 4 -halogenoalkyl; C 1 -C 4 -alkyl-phenyl wherein phenyl may be substituted by F, Cl, Br, I, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -halogenoalkoxy; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; phenoxy; benzyloxy; or

R 10 and R 12 can form a 5- or 6-membered heterocyclic ring comprising a further heteroatom selected from the group consisting of O, S and N.

3. A compound of formula (I) according to claim 1 wherein

R 1 represents C 1 -C 12 -alkyl; or

R 3 represents a non substituted C 2 -C 4 -alkyl, C 3 -C 4 -alkenyl or cyclopropyl; or

R 2 and R 3 can form together a 6-membered heterocycle; or

R 4 represents a non substituted C 1 -C 12 -alkyl, a fluorine or a chlorine atom; or

R 5 represents a non substituted C 1 -C 12 -alkyl, a fluorine or a chlorine atom; or

R 6 represents methyl or ethyl; or

m represents 1, 2 or 3.

4. A compound of formula (I) according to claim 1 wherein

R 1 represents methyl; or

R 3 represents ethyl, n-propyl, i-propyl, propenyl or allyl or

R 2 and R 3 can form together a pipiridinyl or a pyrrolidinyl; or

R 4 represents methyl and ethyl; or

R 5 represents methyl or ethyl.

5. A compound of formula (I) according to claim 1 wherein R 2 and R 3 form together a 2-alkylated-pyrrolidinyl.

6. A compound of formula (I) according to claim 5 wherein R 2 and R 3 form together a 2-methyl-pyrrolidinyl.

7. A method for controlling phytopathogenic fungi of crops, comprising applying an agronomically effective and non-phytotoxic quantity of a compound according to claim 1 to soil where a plant grows and/or is capable of growing, to leaves and/or fruit of a plant and/or to a seed of a plant.

8. A method for controlling damaging insects comprising applying a compound of formula (I) according to claim 1 to a seed, a plant and/or to fruit of a plant or to soil wherein a plant is growing or wherein a plant is desired to grow.

9. A method for preparing a compound of claim 1 comprising reacting a compound of formula (IV):

with one of the following:

wherein B 1 and B 2 each independently represent an alkyl or together a cycloalkykl; or

c. the combination of formula (VII) and formula (VIII)

wherein B 1 , B 2 , and B 3 each independently represent an alkyl, to generate a compound of formula (Ia)

10. The method of claim 9 further comprising the step of reacting a compound of formula (II)

with a compound of formula (IX)

wherein X represents Cl, Br, I, tosylate, SOMe, mesylate, or triflate,

to generate the compound of formula (IV).

11. A method for preparing a compound of claim 1 comprising reacting a compound of formula (III):

with a compound of formula (IX)

wherein X represents Cl, Br, I, tosylate, SOMe, mesylate, or triflate,

to generate a compound of formula (Ia)

12. The method of claim 11 further comprising the step of reacting a compound of formula (II)

with one of the following:

wherein B 1 and B 2 each independently represent an alkyl or together a cycloalkykl; or

c. the combination of formula (VII) and formula (VIII)

wherein B 1 , B 2 , and B 3 each independently represent an alkyl,

to generate the compound of formula (III).

13. A method for preparing a compound of claim 1 comprising reacting a compound of formula (XIV):

with one of the following:

wherein B 1 and B 2 each independently represent an alkyl or together a cycloalkykl; or

c. the combination of formula (VII) and formula (VIII)

wherein B 1 , B 2 , and B 3 each independently represent an alkyl,

to generate a compound of formula (Ib)

14. The method of claim 13 further comprising the step of reacting a compound of formula (XII):

with H 2 to generate the compound of formula (XIV)

15. The method of claim 14 further comprising the step of reacting a compound of formula (X)

wherein X is selected from the group consisting of Cl, Br, I, OTos, and OTf, with a compound of formula (XV)

to generate the compound of formula (XII)

16. A method for preparing a compound of claim 1 comprising the step of reacting a compound of formula (XII):

with H 2 to generate the compound of formula (XIV)

17. The method of claim 16 further comprising the step of reacting a compound of formula (XI)

wherein X represents Cl, Br, I, tosylate, SOMe, mesylate, or triflate,

with a compound of formula (XV)

to generate the compound of formula (XIII)

18. The method of claim 17 further comprising the step of reacting a compound of formula (X)

wherein X is selected from the group consisting of Cl, Br, I, OTos, and OTf,

with one of the following:

wherein B 1 and B 2 each independently represent an alkyl or together a cycloalkykl; or

c. the combination of formula (VII) and formula (VIII)

wherein B 1 , B 2 , and B 3 each independently represent an alkyl,

to generate the compound of formula (XI).