# US 11,440,910 B2 · Pesticidally active heterocyclic derivatives with sulfur containing substituents

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- Number: US 11,440,910 B2
- Document ID: US11440910B2
- Status: Granted
- Kind: B2
- Application number: 16/487,278
- Filed: 2018-02-16
- Published: 2019-12-05
- Granted: 2022-09-13
- Earliest claimed: 2017-02-21
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Sebastian Rendler; Andrew Edmunds; Pierre Joseph Marcel Jung; Michel Muehlebach; Girish Rawal; Indira Sen; Vikas Sikervar
- Web page: https://patentgrep.com/patent/US11440910B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07C 323/62: having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07D 213/78: Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 213/79: Acids; Esters
- C07D 213/81: Amides; Imides
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 487/04: 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## 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 is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
G1 is N or CH;
X1 is O, S or NR3; wherein R3 is hydrogen or C1-C4alkyl;
R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is chlorine, bromine, iodine, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.

### Claim 2 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R1 is C1-C4alkyl or C3-C6cycloalkyl-C1-C4alkyl.

### Claim 3 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R2 is halogen, C1-C4haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl.

### Claim 4 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R7 is hydrogen, fluoro, cyano, C1-C4alkoxycarbonyl, C1-C4alkyl.

### Claim 5 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R8 is cyano or C1-C4alkyl.

### Claim 6 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein X1 is NR3, wherein R3 is C1-C4alkyl.

### Claim 7 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein X is S or SO2.

### Claim 8 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R1 is C1-C4alkyl or cyclopropylmethyl and R2 is halogen or C1-C3haloalkyl.

### Claim 9 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R7 is hydrogen methyl, ethyl or fluoro and R8 is methyl or ethyl.

### Claim 10 (depends on 1)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein
A is CH or N;
X is S or SO2;
G1 is N or CH;
X1 is NCH3;
R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;
R2 is C1-C2haloalkyl;
R7 is methyl; and
R8 is methyl or ethyl.

### Claim 11

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, of formula I,
wherein A is N;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
G1 is N or CH;
X1 is O, S or NR3; wherein R3 is hydrogen or C1-C4alkyl;
R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl.

### Claim 12

A compound of formula IX,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl;
G1 is N or CH;
R3 is hydrogen or C1-C4alkyl;
R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; or a regioisomer thereof, or an isomeric mixture thereof; or
a compound of formula XI,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; or
a compound of formula XII,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; or
a compound of formula XIII,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl;
R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
RLG is C1-C4alkyl and wherein the compound is not
or
a compound of formula XVI,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl;
R11 is C1-C4alkyl; and
RLG is C1-C4alkyl.

### Claim 13 (depends on 12)

The compound of claim 12, wherein the compound is the compound of formula IX.

### Claim 14 (depends on 13)

The compound of claim 13, wherein
A is N;
X is S or SO2;
R1 is ethyl;
R3 is methyl;
R2 is CF3;
R7 is methyl of fluoro; and
R8 is methyl or fluoro.

### Claim 15 (depends on 12)

The compound of claim 12, wherein the compound is the compound of formula XI.

### Claim 16 (depends on 15)

The compound of claim 15, wherein
A is N;
X is S or SO2;
R1 is ethyl;
R7 is methyl of fluoro; and
R8 is methyl or fluoro.

### Claim 17 (depends on 12)

The compound of claim 12, wherein the compound is the compound of formula XVI.

### Claim 18 (depends on 17)

The compound of claim 17, wherein
A is N;
X is S or SO2;
R1 is ethyl;
R7 is methyl of fluoro; and
R8 is methyl or fluoro.

### Claim 19 (depends on 12)

The compound of claim 12, wherein the compound is the compound of formula XIII.

### Claim 20 (depends on 19)

The compound of claim 19, wherein
A is N;
X is S or SO2;
R1 is ethyl;
R7 is methyl of fluoro;
R8 is methyl or fluoro; and
RLG is methyl or ethyl.

### Claim 21 (depends on 12)

The compound of claim 12, wherein the compound is the compound of formula XIII.

### Claim 22 (depends on 21)

The compound of claim 21, wherein
A is N;
X is S or SO2;
R1 is ethyl;
R11 is methyl or ethyl; and
RLG is methyl or ethyl.

### Claim 23

A compound of formula I,
wherein
A is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
G1 is N or CH;
X1 is O, S or NR3; wherein R3 is hydrogen or C1-C4alkyl;
R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
R7 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl; and
R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.

### Claim 24 (depends on 23)

A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 23 and, optionally, an auxiliary or diluent.

### Claim 25 (depends on 23)

A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of the pest, or to a plant susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 23.

### Claim 26 (depends on 24)

A method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with the composition according to claim 24.

### Claim 27 (depends on 23)

The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 23 wherein
A is CH or N;
X is S or SO2;
G1 is N or CH;
X1 is NCH3;
R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;
R2 is C1-C2haloalkyl;
R7 is methyl or fluoro; and
R8 is fluoro, methyl or ethyl.

### Claim 28

A compound selected from
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanedinitrile;
2-[5-ethylsulfonyl-6-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]-3-pyridyl]-2-methyl-propanenitrile;
2-ethyl-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]butanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]butanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanenitrile;
2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanedinitrile;
2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanedinitrile;
ethyl 2-cyano-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanoate;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-3-methyl-butanenitrile;
2-[3-ethylsulfanyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]-2-methyl-propanenitrile;
2-[3-ethylsulfonyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]-2-methyl-propanenitrile;
2-[3-ethylsulfanyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]propanenitrile;
2-[3-ethylsulfonyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]propanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-difluoro-acetonitrile;
2-[3-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-2-methyl-propanenitrile;
2-[3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-2-methyl-propanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-fluoro-propanenitrile;
2-[6-(6-bromo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-5-ethylsulfonyl-3-pyridyl]-2-methyl-propanenitrile;
2-[5-ethylsulfonyl-6-[3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
ethyl 2-cyano-2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanoate;
2-[5-ethylsulfonyl-6-(6-iodo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-3-pyridyl]-2-methyl-propanenitrile;
2-[6-(6-bromo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-5-ethylsulfanyl-3-pyridyl]-2-methyl-propanenitrile;
2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
ethyl 2-cyano-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetate; and
2-[5-ethylsulfanyl-6-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]-3-pyridyl]-2-methyl-propanenitrile.