# US 11,076,596 B2 · Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi

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- Number: US 11,076,596 B2
- Document ID: US11076596B2
- Status: Granted
- Kind: B2
- Application number: 16/644,733
- Filed: 2018-09-10
- Published: 2020-08-20
- Granted: 2021-08-03
- Earliest claimed: 2017-09-18
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Wassilios Grammenos; Violeta Terteryan-Seiser; Maria Angelica Quintero Palomar; Thomas Grote; Bernd Mueller; Michael Seet; Ian Robert Craig; Georg Christoph Rudolf; Jan Klaas Lohmann; Christian Winter; Marcus Fehr; Tobias Mentzel; Christine Wiebe
- Web page: https://patentgrep.com/patent/US11076596B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 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 RA; wherein
RA is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
L is —C(═O)— or —C(═S)—;
R1 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 R11, R12, R13 and R14; wherein R11 is #=N—O—R3; R12 is #=N—N(R4)2; R13 is #-C(═N—O—R3)R5; R14 is #-C(═N—N(R4)2)R5; 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 R1a;
R1a is halogen, oxo, cyano, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, —NHSO2—C1-C4-alkyl, (C═O)—C1-C4-alkyl, C(═O)—C1-C4-alkoxy, C1-C6-alkylsulfonyl, hydroxyC1-C4-alkyl, C(═O)—NH2, C(═O)—NH(C1-C4-alkyl), C1-C4-alkylthio-C1-C4-alkyl, aminoC1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, diC1-C4-alkylamino-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl;
R2 is hydrogen, formyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy or C3-C8-cycloalkyl;
R3 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-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, C1-C6-alkyl and C3-C8-cycloalkyl;
R4 is independently selected from the group consisting of hydrogen, halogen, cyano, formyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C(═O)—(C1-C6-alkyl), C(═O)—(C1-C6-alkoxy), phenyl-C1-C4-alkyl, heteroaryl-C1-C4-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-C1-C4-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, C1-C6-alkyl and C3-C8-cycloalkyl;
R5 is hydrogen, C1-C6-alkyl, amino, cyano, C1-C4-alkylamino, diC1-C4-alkylamino, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C(═O)—(C1-C6-alkyl), C(═O)—(C1-C6-alkoxy), phenyl-C1-C4-alkyl, heteroaryl-C1-C4-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-C1-C4-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, C1-C6-alkyl and C3-C8-cycloalkyl;
with the exception of compounds, wherein the group —NR2— and a radical selected from the group consisting of R13 and R14 are attached to the same ring member atom of the carbocycle of R1.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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 RA, L, R1 and R2 are as defined in claim 1 for compounds of the formula I; with the exception of compounds, wherein the group —NR2— and a radical selected from the group consisting of radicals R13 and R14 are attached to the same ring member atom of the carbocycle of R1.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R1 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 —NR2—.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R2 is hydrogen, formyl, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethyoxy, propyloxy, allyl, propargyl or cyclopropyl.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R3 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C8-cycloalkyl; 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, C1-C6-alkyl and C3-C8-cycloalkyl.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R4 is independently selected from hydrogen, formyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C(═O)—(C1-C6-alkyl), C(═O)—(C1-C6-alkoxy) and phenyl; 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, C1-C6-alkyl and C3-C8-cycloalkyl.

### Claim 9 (depends on 3)

The compound according to claim 3, or the N oxide, or the agriculturally acceptable salt thereof,
wherein
n is 0;
L is —C(═O)—;
R1 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 —NR2—;
R2 is hydrogen, formyl, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethyoxy, propyloxy, allyl, propargyl or cyclopropyl;
R3 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, allyl, propargyl or cyclopropyl.

### Claim 10 (depends on 9)

The compound according to claim 9, wherein R2 is hydrogen.

### Claim 11 (depends on 1)

An agrochemical composition comprising an auxiliary and at least one compound as defined in claim 1.

### Claim 12 (depends on 11)

The agrochemical composition according to claim 11, 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.

### Claim 13 (depends on 1)

The compound as defined in claim 1 for use in combating phytopathogenic harmful fungi.

### Claim 14 (depends on 1)

A method for combating phytopathogenic harmful fungi, comprising treating the fungi, 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.