4-substituted-picolinic acid amide derivatives useful as fungicides
View Patent ↗Compound of general formula (I) in which Y is chosen from the following groups Y 1 to Y 3 (I*), the other substituents being as defined in the description, process for preparing this compound, fungicidal composition comprising this compound, method for treating plants by applying this compound or composition.
1. A compound of the formula (I):
wherein:
Y is
k is 0, 1, or 2;
Het is a five- or six-membered saturated or partially unsaturated, or aromatic ring comprising from one to three heteroatoms independently selected from the group consisting of N, O, and S and which can be substituted with one or two —R 5 groups;
G is selected from the group consisting of —O—, —S—, and —NR 1 ;
Z is —R 1 ;
X 1 and X 2 are independently selected from the group consisting of hydrogen, halogen, —CE 3 , cyano, and nitro;
Q 1 is
Q 2 is —(O) n —R 9 ;
R 1 is hydrogen or C 1 -C 4 alkyl;
R 2 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 halogenoalkyl, and C 1 -C 4 halogenoalkoxy;
R 3 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, and 1 -C 4 alkoxyalkyl;
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;
R 9 is R 5 or
n is 0 or 1;
j, q, and t are independently 0, 1, 2, 3, or 4;
and the optional N-oxides, geometric and/or optical isomers, enantiomers and/or diastereoisomers, tautomeric forms, salts, metal and metalloid complexes of the compounds of formula (I) as they have just been defined.
2. A process for the preparation of a compound of the formula (I)
wherein
Y, X 1 , X 2 G, Z, Q 1 , and Q 2 are as defined in claim 1 ,
k=0, and
the Het group is directly linked to the rest of the structure by a nitrogen atom, comprising reacting a compound of the formula (IIIa) according to scheme S-II:
3. The compound of claim 1 wherein Y is selected from the group consisting of pyrroles, dimethylpyrroles and imidazole.
4. The compound of claim 1 wherein G is —O—.
5. A fungicidal composition comprising an effective amount of the compound of claim 1 and an agriculturally acceptable support.
6. The fungicidal composition of claim 5 further comprising a surfactant.
7. The fungicidal composition of claim 5 comprising from 0.05% to 99% by weight of active material.
8. The fungicidal composition of claim 6 , comprising from 0.05% to 99% by weight of active material.
9. A method for preventively or curatively combating the phytopathogenic fungi of crops comprising applying an effective and non-phytotoxic amount of the fungicidal composition of claim 5 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.
10. The method of claim 9 wherein the dose of active material applied is between 10 g and 800 g of active material per hectare in the case of foliar treatments.
11. The method of claim 10 wherein the dose of active material applied is between 50 g and 300 g of active material per hectare in the case of foliar treatments.
12. The method of claim 9 wherein 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.
13. The method of claim 12 wherein the dose of active material applied is between 3 g and 150 g per 100 kg of seed, in the case of seed treatments.