Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi

Patent metadata

Field	Value
Publication number	US-11076596-B2
Application number	US-201816644733-A
Country	US
Kind code	B2
Filing date	Sep 10, 2018
Priority date	Sep 18, 2017
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

The present invention relates to novel trifluoromethyloxadiazoles of the formula I as defined herein, or an N-oxide and/or their agriculturally useful salts and to their use for controlling phytopathogenic fungi; to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or 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; to a process for preparing compounds of the formula I; 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 formula I, or an N-oxide, or an agriculturally acceptable salt 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;
L is —C(═O)— or —C(═S)—;
R 1 is a saturated or partially unsaturated monocyclic 3- to 8-membered carbocycle; wherein 1 or 2 ring member atoms of the carbocycle are substituted with radicals independently selected from the group consisting of R 11 , R 12 , R 13 and R 14 ; wherein R 11 is #=N—O—R 3 ; R 12 is #=N—N(R 4 ) 2 ; R 13 is #-C(═N—O—R 3 )R 5 ; R 14 is #-C(═N—N(R 4 ) 2 )R 5 ; and wherein # indicates the position which is attached to the ring member atom of the carbocycle; and wherein the ring member atoms of the carbocycle are further unsubstituted or further substituted with additional 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals R 1a ;
R 1a is halogen, oxo, cyano, NO 2 , OH, SH, NH 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkyl, —NHSO 2 —C 1 -C 4 -alkyl, (C═O)—C 1 -C 4 -alkyl, C(═O)—C 1 -C 4 -alkoxy, C 1 -C 6 -alkylsulfonyl, hydroxyC 1 -C 4 -alkyl, C(═O)—NH 2 , C(═O)—NH(C 1 -C 4 -alkyl), C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aminoC 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, diC 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, aminocarbonyl-C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
R 2 is hydrogen, formyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy or C 3 -C 8 -cycloalkyl;
R 3 is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, phenyl, phenyl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl, or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle; and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms 1, 2 or 3 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 above-mentioned 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, C 1 -C 6 -alkyl and C 3 -C 8 -cycloalkyl;
R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C(═O)—(C 1 -C 6 -alkyl), C(═O)—(C 1 -C 6 -alkoxy), phenyl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl, phenyl, naphthyl, a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle and a 3- to 10-membered saturated or partially unsaturated bicyclic carbocycle; 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 said 5- or 6-membered aromatic heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the aromatic heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms further 1, 2 or 3 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 any of the above-mentioned 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, C 1 -C 6 -alkyl and C 3 -C 8 -cycloalkyl;
R 5 is hydrogen, C 1 -C 6 -alkyl, amino, cyano, C 1 -C 4 -alkylamino, diC 1 -C 4 -alkylamino, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C(═O)—(C 1 -C 6 -alkyl), C(═O)—(C 1 -C 6 -alkoxy), phenyl-C 1 -C 4 -alkyl, heteroaryl-C 1 -C 4 -alkyl, phenyl, naphthyl, a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle or a 3- to 10-membered saturated or partially unsaturated bicyclic carbocycle; 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 said 5- or 6-membered aromatic heterocycle include besides carbon atoms 1, 2 or 3 heteroatoms selected from N, O and S as ring member atoms with the provision that the aromatic heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the ring member atoms of said 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle include besides carbon atoms further 1, 2 or 3 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 any of the above-mentioned 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, C 1 -C 6 -alkyl and C 3 -C 8 -cycloalkyl;
with the exception of compounds, wherein the group —NR 2 — and a radical selected from the group consisting of R 13 and R 14 are attached to the same ring member atom of the carbocycle of R 1 .

2. The compound according to claim 1 , wherein A in formula I is phenyl.

3. The compound according to claim 1 , wherein the compound is of formula 1.1 or an N-oxide or an agriculturally acceptable salt thereof,

wherein n is 0, 1 or 2, and wherein the meaning of the variables R A , L, R 1 and R 2 are as defined in claim 1 for compounds of the formula I; with the exception of compounds, wherein the group —NR 2 — and a radical selected from the group consisting of radicals R 13 and R 14 are attached to the same ring member atom of the carbocycle of R 1 .

4. The compound according to claim 1 , wherein L is —C(═O)—.

5. The compound according to claim 1 , wherein R 1 is selected from the group consisting of R1.1, R1.2, R1.3, R1.4, R1.5, R1.19 and R1.20,

wherein # denotes the position which is bound to the group —NR 2 —.

6. The compound according to claim 1 , wherein R 2 is hydrogen, formyl, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethyoxy,

Assignees

• Basf Se

Inventors

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

Classifications

• A01N43/80

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

• A01N43/82 Primary

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

• C07D271/06 Primary

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

• C07D413/12

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