# US 10,118,906 B2 · Use of substituted oxadiazoles for combating phytopathogenic fungi

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- Number: US 10,118,906 B2
- Document ID: US10118906B2
- Status: Granted
- Kind: B2
- Application number: 15/316,399
- Filed: 2015-06-01
- Published: 2017-05-25
- Granted: 2018-11-06
- Earliest claimed: 2014-06-06
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Andy Wieja; Christian Winter; Claudia Rosenbaum; Doris Kremzow-Graw; Franz Roehl; Joachim Rheinheimer; Manojkumar Poonoth; Violeta Terteryan; Egon Haden; Ana Escribano Cuesta; Janosch Harald Achenbach; Tobias Mentzel; Christine Wiebe
- Web page: https://patentgrep.com/patent/US10118906B2

## CPC

- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 487/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

The present invention relates to the use of novel oxadiazoles of the formula I or an N-oxide and/or their agriculturally useful salts for controlling phytopathogenic fungi, or to 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; and to agrochemical compositions comprising at least one such compound and to agrochemical compositions further comprising seeds.

## Claims

### Claim 1

An agrochemical composition comprising an auxiliary and a compound of formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, NO2, OH, SH, NH2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl or C3-C8-cycloalkoxy; and wherein the aliphatic and alicyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; wherein
Ra 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 or C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl;
Y is O or S;
W is NR1R2; wherein
R1, R2 independently of each other are hydrogen, C1-C6-alkyl, 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 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 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-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a;
or R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 10-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms 1, 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(═O) and C(═S); and wherein the heterocycle is unsubstituted or carries 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, 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;
or an N-oxide or an agriculturally acceptable salt thereof.

### Claim 2 (depends on 1)

The composition of claim 1, wherein A is phenyl.

### Claim 3 (depends on 1)

The composition of claim 1, wherein Y is O.

### Claim 4 (depends on 1)

The composition of claim 1, wherein R1 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl and R2 is phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a.

### Claim 5 (depends on 4)

The composition of claim 4, wherein W is NR1R2 and wherein R1 and R2 independently of each other are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl; and wherein the alicyclic and the cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a.

### Claim 6 (depends on 1)

The agrochemical composition according to claim 1 further comprising at least one further pesticidally active substance.

### Claim 7 (depends on 1)

The agrochemical composition according to claim 1 further comprising 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 8 (depends on 1)

A method for combating phytopathogenic harmful fungi comprising treating fungi or materials, plants, soil or seeds to be protected against fungal attack, with an effective amount of the composition of claim 1.

### Claim 9 (depends on 8)

The method of claim 8, wherein A is phenyl.

### Claim 10 (depends on 8)

The method of claim 8, wherein Y is O.

### Claim 11 (depends on 8)

The method of claim 8, wherein R1 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl and R2 is phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a.

### Claim 12 (depends on 8)

The method of claim 8, wherein R1 and R2 independently of each other are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl; and wherein the alicyclic and the cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a.

### Claim 13 (depends on 1)

The composition of claim 1, wherein R1 is hydrogen and R2 is phenyl; and wherein the phenyl group is unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R1a; and wherein R1a is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-cycloalkyl.

### Claim 14 (depends on 1)

The composition of claim 1, wherein R1 is hydrogen and R2 heteroaryl-C1-C4-alkyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a; and wherein R1a is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-cycloalkyl.

### Claim 15 (depends on 8)

The method of claim 8, R1 is hydrogen and R2 is phenyl; and wherein the phenyl group is unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R1a; and wherein R1a is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-cycloalkyl.

### Claim 16 (depends on 8)

The method of claim 8, wherein R1 is hydrogen and R2 heteroaryl-C1-C4-alkyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a; and wherein R1a is halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-cycloalkyl.