# US 9,775,353 B2 · Pesticidally active heterocyclic derivatives with sulphur containing substituents

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- Number: US 9,775,353 B2
- Document ID: US9775353B2
- Status: Granted
- Kind: B2
- Application number: 15/323,983
- Filed: 2015-07-02
- Published: 2017-06-08
- Granted: 2017-10-03
- Earliest claimed: 2014-07-08
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Andre Stoller; Andre Jeanguenat; Andrew Edmunds; Pierre Joseph Marcel Jung; Daniel Emery; Michel Muehlebach; Peter Renold
- Web page: https://patentgrep.com/patent/US9775353B2

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 471/04: Ortho-condensed systems
- C07F 5/025: {Boronic and borinic acid compounds}
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.

## Claims

### Claim 1

A compound of formula I,
wherein
A represents CH or N;
each R is, independently from each other, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylsulfanyl, C1-C4haloalkylsulfanyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, C1-C6alkylamino, C2-C8dialkylamino, halogen, cyano, cyanoC1-C4alkyl, tri(C1-C4alkyl)silyl, C1-C4alkoxyC1-C4alkoxy, C1-C4alkylsulfanylC1-C4alkoxy or nitro;
or each R is, independently from each other, phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, imidazolyl, pyrazolyl, oxazolyl or oxadiazolyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C1-C6alkyl and cyano;
n is 0, 1, 2, 3, 4 or 5;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl, C3-C6cycloalkyl mono-, di- or trisubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl; or R1 is C3-C6cycloalkyl-C1-C4alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl;
or R1 is C2-C6alkenyl, C2-C6haloalkenyl or C2-C6alkynyl;
R2 is halogen, C1-C4haloalkyl or C1-C4haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano;
or R2 is C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, O(C1-C4haloalkyl) or —C(O)C1-C4haloalkyl;
or R2 is C3-C6cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl; and
X1 is O, S or NR3, wherein R3 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy-C1-C4alkyl or C3-C6cycloalkyl;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1, represented by the compounds of formula I-1
wherein
R, R2 and n are as defined under formula I in claim 1;
Xa1 is S, SO or SO2; and
Ra1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

### Claim 3 (depends on 2)

A compound of formula I-1 according to claim 2, wherein
n is 1 and R is halogen, cyano or C1-C4haloalkyl.

### Claim 4 (depends on 1)

A compound of formula I according to claim 1, represented by the compounds of formula I-2
wherein
R, R2 and n are as defined under formula I in claim 1;
Xa2 is S, SO or SO2; and
Ra2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

### Claim 5 (depends on 4)

A compound of formula I-2 according to claim 4, wherein
n is 1 and R is halogen, cyano or C1-C4haloalkyl.

### Claim 6 (depends on 1)

A compound of formula I according to claim 1, represented by the compounds of formula Ia
wherein
X2 is SO2;
X3 is N—C1-C4alkyl;
R4 is C1-C4alkyl;
R5 is halogen, C1-C4haloalkyl, cyano or C1-C4alkoxy;
n is 1, 2 or 3; and
R6 is C1-C4haloalkyl.

### Claim 7 (depends on 1)

A compound of formula I according to claim 1, represented by the compounds of formula Ib
wherein
A is N or CH;
X2 is S or SO2;
X3 is N—C1-C4alkyl;
R7 is C1-C4alkyl;
R8 is halogen, cyano, C1-C4haloalkyl or C1-C4alkoxy;
n is 0, 1, 2 or 3; and
R9 is C1-C4haloalkyl.

### Claim 8 (depends on 1)

A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.