Picolinamine derivatives and their use as fungicides

1. A compound of the general formula (I):

in which:

Y and G together with carbon atoms 3 and 4, form a 5 or 6 member ring selected from the group consisting of the following structures A to F:

in which:

each J is independently selected from the group consisting of oxygen and sulphur;

X is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and C 1 -C 4 halogenoalkyl;

K 1 and K 2 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 halogenoalkyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 alkythioalkyl, —OR 1 , —SR 1 , —SOR 1 , —SO 2 R 1 , —NHR 3 , —NR 1 R 3 and

X 1 and X 2 are independently selected from the group consisting of hydrogen, halogen, —CF 3 , a cyano group and a nitro group;

Q 1 is selected from the group consisting of —(CH 2 ) q —,

Q 2 is selected from the group consisting of —(O) n —R 5 , a cyano group,

R 1 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 halogenoalkyl, alkenyl, alkynyl, heterocyclyl, —CH═O, —(C—O)-alkyl and —(C═O)-Oalkyl;

R 2 is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 halogenoalkyl and aryl;

R 3 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 halogenoalkyl, C 1 -C 4 alkoxy, alkenyl, alkynyl, heterocyclyl, —CH═O, —(C═O)-alkyl and —(C═O)-Oalkyl;

R 4 is selected from the group consisting of halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxyalkyl;

R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, and C 1 -C 4 halogenoalkyl;

R 7 and R 8 are independently selected from the group consisting of hydrogen and halogen;

n is 0 or 1;

i, j, p, q and t are independently chosen as being 0,1,2,3 or 4;

r is 0, 1, 2 or 3;

as well as any optional N-oxides, optical isomers, enantiomers and/or diastereoisomers, tautomeric forms, and salts of the compounds of formula (I) as here-above defined.

2. The compound of claim 1 , wherein X 1 and X 2 represent a hydrogen atom.

3. The compound of claim 1 , wherein Y and G with carbon 3 and 4form a ring chosen from structures A to C.

4. The compound of claim 1 , wherein Q 1 is selected from the group consisting of:

5. The compound of claim 1 , wherein:

X 1 and X 2 each represent hydrogen,

Y and G together with carbon 3 and 4, form a 5 member ring chosen from structures A to C, and

Q 1 is selected from the

6. The compound of claim 5 , wherein:

X 1 and X 2 each represent hydrogen,

Y and G together with carbon 3 and 4, form a 5 member ring chosen from:

in which:

X is hydrogen

K 1 and K 2 are independently selected from the group consisting of hydrogen, alkyl and N,N-dialkylamino; and

Q 1 is selected from the group consisting of

7. The compound of claim 6 , wherein:

Y and G together with carbon 3 and 4, may form a 5 member ring of formula A:

in which:

J is oxygen,

X is hydrogen; and

Q 1 is selected from the group consisting of

8. Process for preparing the compound according to claim 1 which comprises reacting a compound of general formula (II)

in which X 1 , X 2 , Q 1 and Q 2 are as defined above and W is NH 2 or N 3 , with a phosgene or thiophosgene solution, an acid halide or a ketone in the presence is of solvent.

9. Process according to claim 8 for preparing the compound of general formula (I-A):

in which J, X, X 1 , X 2 , Q 1 and Q 2 are as defined above, characterised in that it comprises reacting the compound of general formula (II) where W is NH 2 in an apolar aprotic solvent.

10. Process according to claim 9 , characterised in that the solvent is an hydrocarbon solvent such as benzene and toluene and that it is carried out at reflux or at a temperature of between 20° C. and 200° C.

11. Process according to claim 8 for preparing the compound of general formula (I-B):

in which K 1 , X, X 1 , X 2 , Q 1 and Q 2 are as defined above, characterised in that it comprises reacting the compound of general formula (II) where W is NH 2 with acid chloride and a base such as triethylamine in a chlorinated solvent, the subsequent reduction of the intermediate being obtained with a reducing agents such as triphenyl phosphine or sodium borohydride in an alcoholic solvent such as ethanol or THF.

12. Process according to claim 11 , characterised in that the solvent is dichioromethane and that it is carried out at room temperature or at a temperature between −10° C. and +50° C., followed by addition of an amine.

13. Process according to claim 8 for preparing the compound of general formula (I-C):

in which X, K 1 , K 2 , X 3 , Q 1 and Q 2 are as defined above, characterised in that it comprises reacting the compound of general formula (II) in which W is NH 2 with alkyl or aryl ketone in an apolar aprotic solvent.

14. Process according to claim 13 , characterised in that the solvent is an hydrocarbon solvent such as benzene and toluene and that it is carried out at reflux or at a temperature of between 20° C. and 200° C.

15. A fungicidal composition comprising an effective amount of a compound according to claim 1 and an agriculturally acceptable support.

16. The fungicidal composition of claim 15 further comprising a surfactant.

17. The flungicidal composition of claim 15 , comprising from 0.05% to 99% by weight of active material.

18. Method for preventively or curatively combating the phytopathogenic fungi of crops, characterised in that an effective and non-phytotoxic amount of a composition according to claim 15 is applied to the plant seeds or to the plant leaves and/or to the fruits of the plants or to the soil in which the plants are growing or in which it is desired to grow them.

19. Method according to claim 18 , in which the dose of active material applied is between 10 g and 800 g of active material per hectare, in the case of foliar treatments.

20. Method according to claim 19 , in which the dose of active material applied is between 50 g and 300 g of active material per hectare in the case of foliar treatments.

21. Method according to claim 18 , in which the dose of active material applied is between 2 and 200 g of active material per 100 kg of seed, in the case of seed treatments.

22. The compound of claim 2 wherein Y and G with carbon 3 and 4form a ring selected from the group consisting of structures A to C.

23. The fungicidal composition of claim 16 , comprising from 0.05% to 99% by weight of active material.

24. The compound of claim 1 wherein the compound of the general formula (I) is selected from the group consisting of:

(A) compounds and intermediates of the formula:

wherein

X, X 1 , and X 2 are hydrogen;

J is oxygen or sulphur;

Q 1 is

Q 2 is

where R 5 is C 1 -C 4 halogenoalkyl; and

(B) compounds and intermediates of the formula:

wherein

X 1 and X 2 are hydrogen;

K 1 is C 1 -C 4 alkyl;

Q 1 is

and

Q 2 is a halogen or

where R 5 is C 1 -C 4 halogenoalkyl.