Substituted oxadiazoles for combating phytopathogenic fungi

Patent metadata

Field	Value
Publication number	US-11425910-B2
Application number	US-201816487121-A
Country	US
Kind code	B2
Filing date	Feb 13, 2018
Priority date	Feb 21, 2017
Publication date	Aug 30, 2022
Grant date	Aug 30, 2022

Abstract

The present invention relates to novel trifluoromethyloxadiazoles of the formula I, or the N-oxides, or the agriculturally useful salts thereof; and to their use for controlling phytopathogenic fungi; and to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of the formula I; and to agrochemical compositions further comprising seeds.

First claim

The invention claimed is:

1. A compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof;

wherein:
R A is independently selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy;
n is 0, 1 or 2;
L is —(C═S)—;
R 1 is C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; wherein any of the aliphatic groups are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum possible number of identical or different radicals selected from the group consisting of hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkyl;
R 2 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, phenyl, C(═O)—(C 1 -C 6 -alkyl) or C(═O)—(C 1 -C 6 -alkoxy); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkyl;
R 3 , R 4 independently of each other are selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy;
or R 3 and R 4 together with the carbon atom to which they are bound form a saturated 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1, 2 or 3 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group R N ; wherein
R N is hydrogen, C 1 -C 6 -alkyl or halogen;
and wherein said S ring member atom is unsubstituted or substituted with 1 or 2 oxo radicals; and wherein one or two CH 2 groups of the saturated carbocycle or of the saturated heterocycle may be replaced by one or two groups independently selected from —C(═O)— and —C(═S)—; and wherein the carbon ring member atoms of the saturated carbocycle or of the saturated heterocycle are unsubstituted or substituted with a total number of 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkyl;

with the exception of compounds of the formula I wherein R 3 and R 4 both are hydrogen.

2. The compound of claim 1 having formula I.1, or an N-oxide, or an agriculturally acceptable salt thereof

wherein n is 0 or 1.

3. The compound of claim 1 , wherein n is 0.

4. The compound of claim 1 , wherein R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl; or R 3 and R 4 together with the carbon atom to which they are bound form a cyclopropyl ring; with the exception of compounds of the formula I wherein R 3 and R 4 both are hydrogen.

5. The compound of claim 1 , wherein R 3 is hydrogen and R 4 is methyl or trifluoromethyl.

6. The compound of claim 1 , wherein R 3 and R 4 together with the carbon atom to which they are bound form a cyclopropyl ring.

7. The compound of claim 1 , wherein R 1 is C 1 -C 6 -alkyl; unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkyl.

8. The compound of claim 1 , wherein R 2 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl or phenyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy.

9. The compound of claim 1 , wherein R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, ethynyl, propargyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl or phenyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen and C 1 -C 6 -alkyl; and R 1 is C 1 -C 6 -alkyl.

10. An agrochemical composition, which comprises an auxiliary and at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, as defined in claim 1 .

11. The agrochemical composition of claim 10 , wherein the auxiliary is selected from the group of ionic or non-ionic surfactants.

12. Seed treated with the composition of claim 10 , wherein the amount of the compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed.

13. A method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof, as defined in claim 1 .

14. The method of claim 13 , wherein the compound of formula I is a compound of formula I.1, or an N-oxide, or an agriculturally acceptable salt thereof

wherein n is 0 or 1.

15. The method of claim 13 , wherein R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl; or R 3 and R 4 together with the carbon atom to which they are bound form a cyclopropyl ring; with the exception of compounds of the formula I wherein R 3 and R 4 both are hydrogen.

16. The method of claim 13 , wherein R 3 is hydrogen and R 4 is methyl or trifluoromethyl.

17. The method of claim 13 , wherein R 3 and R 4 together with the carbon atom to which they are bound form a cyclopropyl ring.

18. The method of claim 13 , wherein R 1 is C 1 -C 6 -alkyl; unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of C 1 -C 6 -alkoxy and C 3 -C 8 -cycloalkyl.

19. The method of claim 13 , wherein R 2 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl or phenyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy.

20. The method of claim 13 , wherein R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, ethynyl, propargyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl or phenyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen and C 1 -C 6 -alkyl; and R 1 is C

Assignees

• Basf Se

Inventors

• Grammenos Wassilios
• Terteryan-Seiser Violeta
• Quintero Palomar Maria Angelica
• Craig Ian Robert
• Wiebe Christine
• Mentzel Tobias
• Fehr Marcus
• Escribano Cuesta Ana
• Winter Christian Harald
• Lohmann Jan Klaas
• Mueller Bernd
• Grote Thomas
• Cambeis Erica
• Seet Michael

Classifications

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• A01N47/12

  containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring · CPC title

• A01P3/00

  Fungicides · CPC title

• C07D271/06 Primary

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title