Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi

Patent metadata

Field	Value
Publication number	US-2020315177-A1
Application number	US-201816765524-A
Country	US
Kind code	A1
Filing date	Nov 7, 2018
Priority date	Nov 23, 2017
Publication date	Oct 8, 2020
Grant date	—

Abstract

The present invention relates to trifluoromethyloxadiazoles of the formula (I), or the N-oxides, or the agriculturally useful salts thereof; to a process for preparing compounds of the formula (I); to intermediates which are useful in the preparation of compounds of the formula (I); to the use of compounds of the formula (I) for controlling phytopathogenic fungi; 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), or an N-oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions further comprising seeds.

First claim

1 . Compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof,

wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle; wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the phenyl ring or the aromatic heterocycle is unsubstituted or substituted with 1, 2, 3 or 4 identical or different groups R A ; wherein
R A is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy;

W is a 3- or 4-membered non-aromatic heterocycle containing as ring member atoms besides carbon atoms 1 nitrogen atom; wherein the heterocycle is bound to the group L through said nitrogen ring member atom; and wherein the heterocycle is bound to the group A through one of the carbon ring member atoms; and wherein the heterocycle is further unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R W ; wherein
R W is halogen, cyano, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy or C 1 -C 3 -haloalkoxy;

L is —C(═O)—, —C(═S)—, —S(═O) p —, —C(═O)—O-#, —C(═O)NR 2 -# or —C(═S)NR 2 -#; wherein # denotes the position, which is bound to radical R 1 ; and wherein
p is 0, 1 or 2;
R 2 is hydrogen, formyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 5 -cycloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkyl;

R 1 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyloxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkynyloxyimino-C 1 -C 4 -alkyl, C 3 -C 11 -cycloalkyl, C 3 -C 11 -cycloalkenyl, C 3 -C 11 -cycloalkyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and
wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(═O) and C(═S); and wherein the heterocyclyl group in heterocyclyl-C 1 -C 4 -alkyl is a 3- to 10-membered saturated, partially unsaturated, mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from 0 and S; and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(═O) and C(═S); and

wherein the heteroaryl group in heteroaryl-C 1 -C 4 -alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the provision that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R 1 are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different groups R 1a ; wherein R 1a is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy.

2 . Compounds according to claim 1 , wherein A in compounds of the formula I is phenyl.

3 . Compounds according to claim 2 , which are of the formula I..1, or the N-oxides, or the agriculturally acceptable salts thereof,

wherein n is 0, 1 or 2, and wherein the meaning of the variables R A , W, L, R 1 and R 2 , are as defined in claim 1 for compounds of the formula I.

4 . Compounds according to claim 1 , wherein W is selected from the group consisting of W.a, W.b and W.c,

wherein # denotes the position, which is attached to the group A, and the dashed line denotes the position, which is attached to R 1 .

5 . Compounds according to claim 1 , wherein L is —C(═O)—.

6 . Compounds according to claim 1 , wherein L is —S(═O) 2 —.

7 . Compounds according to claim 1 , wherein L is —C(═O)NR 2 -# or
—C(═S)NR 2 -#; wherein # denotes the position, which is bound to radical R 1 .

8 . Compounds according to claim 1 , wherein R 1 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl or C 3 -C 11 -cycloalkyl.

9 . Compounds according to claim 1 , wherein R 1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

10 . Intermediate compounds of the formula II

wherein the variables A, R A , W and R W are as defined in claim 1 for compounds of the formula I.

11 . Intermediate compounds of the formula XV

wherein the variables A, R A , W, R W , L, p, R 1 and R 2 are as defined in claim 1 for compounds of the formula I.

12 . An agrochemical composition, which comprises an auxiliary and at least one compound as defined in claim 1 .

13 . An agrochemical composition according to claim 12 , further comprising seed, wherein the amount of the at least one compound is from 0.1 g to 10 kg per 100 kg of seed.

14 . (canceled)

15 . A method for combating phytopathogenic harmful fungi, which process comprises treating the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound as defined in claim 1 .

Assignees

• Basf Se

Inventors

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

Classifications

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/82 Primary

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