# US 10,499,644 B2 · Substituted oxadiazoles for combating phytopathogenic fungi

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- Number: US 10,499,644 B2
- Document ID: US10499644B2
- Status: Granted
- Kind: B2
- Application number: 15/777,281
- Filed: 2016-11-16
- Published: 2018-11-15
- Granted: 2019-12-10
- Earliest claimed: 2015-11-19
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Violeta Terteryan-Seiser; Manuel Kretschmer; Wassilios Grammenos; Christine Wiebe; Maria Angelica Quintero Palomar; Marcus Fehr; Ian Robert Craig; Tobias Mentzel; Christian Harald Winter; Ana Escribano Cuesta; Jan Klaas Lohmann; Thomas Grote; Bernd Mueller; Erica Cambeis
- Web page: https://patentgrep.com/patent/US10499644B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 413/14: containing three or more hetero rings
- 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 the compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof and to their use for combating phytopathogenic harmful fungi, wherein the variables are defined as given in the description and claims. Further present invention relates to mixtures comprising at least one such compound of the formula I and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one such compound of the formula I and to agrochemical compositions further comprising seeds.

## Claims

### Claim 1

A compound of the formula I
wherein:
A is phenyl, wherein the group —C(R3R4)—NR1R2 is attached to the phenyl ring in a position para to the trifluoromethyloxadiazole group; and wherein the phenyl group is unsubstituted or substituted by 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;
R1, R2 independently of each other are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C(═O)—(C1-C6-alkyl), or C(═O)—(C1-C6-alkoxy); and wherein the cycloalkyl group is unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R1a;
wherein
R1a is halogen, 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 or C1-C6-alkylsulfonyl;
R3 and R4 together with the carbon atom to which they are bound form a 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside carbon atoms 1, 2 or 3 heteroatoms independently selected from the group consisting of N—RN, S, S(═O), S(═O)2 and O as ring member atoms; wherein RN is hydrogen, C1-C6-alkyl, SO2CH3, SO2C6H4CH3 or S02-aryl;
and wherein one or two CH2 groups of the cycle may be replaced by one or two groups independently selected from the group of C(═O) and C(═S); and wherein the carbocycle, heterocycle and aryl is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R3a; wherein
R3a is halogen, 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 or C1-C6-alkylsulfonyl;
or N-oxide or an agriculturally acceptable salt thereof;
with the exception of N-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]cyclopropyl]propanamide.

### Claim 2 (depends on 1)

The compound of claim 1, wherein A is unsubstituted.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring.

### Claim 4 (depends on 2)

The compound of claim 2, wherein
R3 and R4 together with the carbon atom to which they are bound form a 3- to 7-membered carbocycle, wherein one or two CH2 groups of the cycle may be replaced by one or two groups independently selected from the group of C(═O) and C(═S); and wherein the carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R3a; wherein
R3a is halogen, 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 or C1-C6-alkylsulfonyl.

### Claim 5 (depends on 1)

A mixture comprising at least one compound of the formula I of claim 1 and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators.

### Claim 6 (depends on 1)

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, of claim 1.

### Claim 7 (depends on 6)

The agrochemical composition of claim 6, wherein the auxiliary is selected from the group consisting of anionic, cationic and nonionic surfactants.

### Claim 8 (depends on 6)

The agrochemical composition of claim 6, further comprising a seed, 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.

### Claim 9 (depends on 1)

A method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, 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.

### Claim 10 (depends on 9)

The method of claim 9, wherein A is unsubstituted.

### Claim 11 (depends on 9)

The method of claim 9, wherein
R3 and R4 together with the carbon atom to which they are bound form a 3- to 7-membered carbocycle, wherein one or two CH2 groups of the cycle may be replaced by one or two groups independently selected from the group of C(═O) and C(═S); and wherein the carbocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R3a; wherein
R3a is halogen, 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 or C1-C6-alkylsulfonyl.

### Claim 12 (depends on 11)

The method of claim 11, wherein R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring.