Pyridine derivatives as fungicidal compounds
View Patent ↗Compound of general formula (I): Process for preparing this compound. Novel intermediate of general formula (E): for the preparation of compound of general formula (I) Fungicidal composition comprising a compound of general formula (I). Method for treating plants by applying a compound of general formula (I) or a composition comprising it.
1. A compound of the general formula (I):
in which:
X is an oxygen atom;
each Y is independently selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxy, C1-C6-alkoxy-C1-C6-alkylcarbonyl, a carboxyl group, a C 1 -C 8 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylamino, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylthio, a C 1 -C 6 -halogenoalkylthio having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkinyloxy, a C 3 -C 8 -halogenoalkinyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -alkylsulphinyl, a C 1 -C 8 -alkylsulphonyl, a C 1 -C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms and a C 1 -C 6 -alkoximino-C 1 -C 6 -alkyl, provided that at least one Y substituent is a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms;
R 1 is selected from the group consisting of a hydrogen atom, a cyano group, a nitro group, a formyl group, a C 1 -C 6 -alkyl, a C 1 -C 6 -alkylcarbamoyl, a C 2 -C 6 -alkenyl, a C 2 -C 6 -alkynyl, a C 1 -C 6 -halogenoalkyl having 1 to 7 halogen atoms, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, a C 1 -C 6 -cyanalkyl, a C 1 -C 6 -aminoalkyl, a C 3 -C 6 -cycloalkyl, a C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -halogenalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -alkylsulfanyl and a C 1 -C 6 -halogenalkylsulfanyl having 1 to 5 halogen atoms;
n is 1, 2, 3 or 4; and
Het is selected from the group consisting of substituted 6-membered heterocyclic moieties selected from the group consisting of:
wherein:
R 51 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -akylthio, a C 1 -C 4 -halogenoakylthio having 1 to 5 halogen atoms or a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms;
R 52 , R 53 and R 54 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl or a C 1 -C 4 -alkylsulphonyl; provided that at least one of R 51 , R 52 , R 53 , and R 54 is not hydrogen;
wherein:
R 55 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, an amino group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 5 -alkylthio, a C 2 -C 5 -alkenylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a phenyloxy optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, or a phenylthio optionally substituted by a halogen atom or a C 1 -C 4 -alkyl;
R 56 , R 57 and R 58 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl, a C 1 -C 4 -alkylsulphonyl or a N-morpholine optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, or a thienyl optionally substituted by a halogen atom or a C 1 -C 4 -alkyl; provided that at least one of R 55 , R 56 , R 57 , and R 58 is not hydrogen; and
wherein
R 59 , R 60 , R 61 and R 62 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl or a C 1 -C 4 -alkylsulphonyl; provided that at least one of R 59 , R 60 , R 61 , and R 62 is not hydrogen;
Het being linked by a carbon atom, as indicated.
2. The compound of claim 1 wherein n is 1 or 2.
3. The compound of claim 2 wherein n is 2.
4. The compound of claim 1 wherein there is at least one Y substituent that is selected from the group consisting of a halogen atom, a C 1 -C 8 -alkyl, and a C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl.
5. The compound of claim 1 wherein at least one Y substituent is —CF 3 .
6. The compound of claim 1 wherein the 2-pyridyl group of the (pyridin-2-yl)-ethyl moiety is substituted in the 3- and/or in the 5-position.
7. The compound of claim 5 wherein the 2-pyridyl group of the (pyridin-2-yl)-ethyl moiety is substituted in the 5-position by —CF 3 .
8. A fungicidal composition comprising an effective amount of a compound according to claim 1 , and an agriculturally acceptable support.
9. The fungicidal composition of claim 8 further comprising a surfactant.
10. The fungicidal composition of claim 8 , comprising from 0.05% to 99% by weight of the compound of formula I.
11. The compound of claim 6 wherein the 2-pyridyl group of the (pyridin-2-yl)-ethyl moiety is substituted in the 5-position by —CF 3 .
12. The fungicidal composition of claim 9 , comprising from 0.05% to 99% by weight of the compound of formula I.
13. A method for combating and/or controlling phytopathogenic fungi selected from the group consisting of Alternaria brassicae and Pyrenophora teres comprising applying an effective and non-phytotoxic amount of a compound of the general formula (I):
in which:
X is an oxygen atom;
each Y is independently selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxy, a C1-C6-alkoxy-C1-C6-alkylcarbonyl, a carboxyl group, a C 1 -C 8 -alkyl, a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylamino, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylthio, a C 1 -C 6 -halogenoalkylthio having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkinyloxy, a C 3 -C 8 -halogenoalkinyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -alkylsulphinyl, a C 1 -C 8 -alkylsulphonyl, a C 1 -C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms and a C 1 -C 6 -alkoximino-C 1 -C 6 -alkyl, provided that at least one Y substituent is a C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms;
R 1 is selected from the group consisting of a hydrogen atom, a cyano group, a nitro group, a formyl group, a C 1 -C 6 -alkyl, a C 1 -C 6 -alkylcarbamoyl, a C 2 -C 6 -alkenyl, a C 2 -C 6 -alkynyl, a C 1 -C 6 -halogenoalkyl having 1 to 7 halogen atoms, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, a C 1 -C 6 -cyanalkyl, a C 1 -C 6 -aminoalkyl, a C 3 -C 6 -cycloalkyl, a C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -halogenalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl, a C 1 -C 6 -alkylsulfanyl and a C 1 -C 6 -halogenalkylsulfanyl having 1 to 5 halogen atoms;
n is 1, 2, 3 or 4; and
Het is selected from the group consisting of substituted 6-membered heterocyclic moieties selected from the group consisting of:
wherein:
R 51 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -akylthio, a C 1 -C 4 -halogenoakylthio having 1 to 5 halogen atoms or a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms;
R 52 , R 53 and R 54 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl or a C 1 -C 4 -alkylsulphonyl; provided that at least one of R 51 , R 52 , R 53 , and R 54 is not hydrogen;
wherein:
R 55 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, an amino group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 5 -alkylthio, a C 2 -C 5 -alkenylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a phenyloxy optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, or a phenylthio optionally substituted by a halogen atom or a C 1 -C 4 -alkyl;
R 56 , R 57 and R 58 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 1 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl, a C 1 -C 4 -alkylsulphonyl or a N-morpholine optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, or a thienyl optionally substituted by a halogen atom or a C 1 -C 4 -alkyl; provided that at least one of R 55 , R 56 , R 57 , and R 58 is not hydrogen; and
wherein
R 59 , R 60 , R 61 and R 62 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl or a C 1 -C 4 -alkylsulphonyl; provided that at least one of R 59 , R 60 , R 61 ,and R 62 is not hydrogen;
Het being linked by a carbon atom, as indicated;
to plant seeds or to the plant leaves and/or to fruits of plants or to soil in which plants are growing or in which the plants are desired to grow.
14. The method of claim 13 wherein Het represents a heterocycle of the general formula (XXII)
in which: R 51 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms and a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms; and R 52 , R 53 and R 54 , are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl and a C 1 -C 4 -alkylsulphonyl.
15. The method of claim 13 wherein Het represents a heterocycle of the general formula (XXIII)
in which:
R 55 is selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C5-alkylthio, a C 2 -C5-alkenylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a phenyloxy optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, and a phenylthio optionally substituted by a halogen atom or a C 1 -C 4 -alkyl;
R 56 , R 57 and R 58 are independently selected form the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkyl-sulphinyl, a C 1 -C 4 -alkylsulphonyl, a N-morpholine optionally substituted by a halogen atom or a C 1 -C 4 -alkyl, and a thienyl optionally substituted by a halogen atom or a C 1 -C 4 -alkyl.
16. The method of claim 13 wherein Het represents a heterocycle of the general formula (XXIV)
in which R 59, R 60 , R 61 and R 62 are independently selected from the group consisting of a halogen atom, a hydroxy group, a cyano group, a C 1 -C 4 -alkyl, a C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 4 -alkoxy, a C 1 -C 4 -alkylthio, a C 1 -C 4 -halogenoalkylthio having 1 to 5 halogen atoms, a C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 4 -alkylsulphinyl and a C 1 -C 4 -alkylsulphonyl.
17. The method of claim 13 wherein n is 1 or 2.
18. The method of claim 17 wherein n is 2.
19. The method of claim 13 wherein there is at least one Y substituent that is selected from the group consisting of a halogen atom, a C 1 -C 8 -alkyl, and a C 1 -C 6 -alkoxy-C 1 -C 6 -alkylcarbonyl.
20. The method of claim 13 wherein at least one Y substituent is —CF 3 .
21. The method of claim 13 wherein the 2-pyridyl group of the (pyridin-2-yl)-ethyl moiety is substituted in the 3- and/or in the 5-position.
22. The method of claim 20 wherein the 2-pyridyl group of the (pyridin-2-yl)-ethyl moiety is substituted in the 5-position by —CF 3 .
23. The method of claim 21 wherein the 2-pyridyl group of the (pyridin-2-yl )-ethyl moiety is substituted in the 5-position by —CF 3 .