# US 10,945,435 B2 · Imidazopyrimidine derivatives with sulfur containing phenyl and pyridyl substituents

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- Number: US 10,945,435 B2
- Document ID: US10945435B2
- Status: Granted
- Kind: B2
- Application number: 16/611,733
- Filed: 2018-05-02
- Published: 2020-04-02
- Granted: 2021-03-16
- Earliest claimed: 2017-05-08
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Andrew Edmunds; Sebastian Rendler; Michel Muehlebach; Daniel Emery
- Web page: https://patentgrep.com/patent/US10945435B2

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 487/04: Ortho-condensed systems
- 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

Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable 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
A1 is CH or N;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl or C3-C6cycloalkylC1-C4alkyl;
R2 is halogen, hydroxy, mercapto, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
R3 is hydrogen, C1-C6alkyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C3-C6alkenyl, C3-C6alkynyl, C3-C6halocycloalkylC1-C4alkyl, C1-C4alkoxyC1-C4alkyl, C1-C4alkoximinoC1-C4alkyl, C1-C4alkylsulfanylC1-C4alkyl, C1-C4alkylsulfinylC1-C4alkyl, C1-C4alkylsulfonylC1-C4alkyl, C1-C6cyanoalkyl, aminocarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl, di(C1-C4alkyl)aminocarbonylC1-C4alkyl, hydroxycarbonylC1-C4alkyl, C1-C4alkoxycarbonylC1-C4alkyl, C1-C6cyanohaloalkyl, aminocarbonylC1-C4haloalkyl, hydroxycarbonylC1-C4haloalkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, C1-C4alkoxycarbonimidoyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl;
or R3 is a four- to six-membered heterocyclic ring system which can be partially saturated or fully saturated, said ring system contains 1 to 2 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkoxy, C1-C4haloalkyl and oxo; wherein the sulfur can be present in the oxidation states of 0, 1 or 2;
R4 is hydrogen, halogen or C1-C4alkyl; and
R5 is hydrogen, halogen or C1-C4alkyl;
or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula (I).

### Claim 2 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R3 is hydrogen, C1-C6alkyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C3-C6alkenyl, C3-C6alkynyl, C3-C6halocycloalkylC1-C4alkyl, C1-C4alkoxyC1-C4alkyl, C1-C4alkoximinoC1-C4alkyl, C1-C4alkylsulfanylC1-C4alkyl, C1-C4alkylsulfinylC1-C4alkyl, C1-C4alkylsulfonylC1-C4alkyl, C1-C6cyanoalkyl, aminocarbonylC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl, di(C1-C4alkyl)aminocarbonylC1-C4alkyl, hydroxycarbonylC1-C4alkyl, C1-C4alkoxycarbonylC1-C4alkyl, C1-C6cyanohaloalkyl, aminocarbonylC1-C4haloalkyl, hydroxycarbonylC1-C4haloalkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, C1-C4alkoxycarbonimidoyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl; or R3 is a four- to six-membered heterocyclic ring system which can be partially saturated or fully saturated, said ring system contains 1 to 2 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl and oxo, wherein the sulfur can be present in the oxidation states of 0, 1 or 2; or
R3 is oxetanyl which can be mono-substituted by C1-C4alkyl.

### Claim 3 (depends on 1)

A 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 4 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R2 is C1-C2haloalkyl, halomethylsulfanyl, halomethylsulfinyl or halomethylsulphonyl.

### Claim 5 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R3 is C1-C4 cyanoalkyl, C1-C4alkylsulfanylC1-C4alkyl, C1-C4alkylsulfinylC1-C4alkyl or C1-C4alkylsulfonylC1-C4alkyl; or R3 is oxetanyl which can be mono-substituted by C1-C4alkyl.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R4 and R5 are both hydrogen.

### Claim 8 (depends on 1, 7)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 or 7 wherein R1 is ethyl and R2 is trifluoromethyl, pentafluoroethyl or trifluoromethylsulfanyl.

### Claim 9 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R3 is C1-C4 cyanoalkyl, C1-C2alkylsulfanylC1-C2alkyl, C1-C2alkylsulfinylC1-C2alkyl or C1-C2alkylsulfonylC1-C2alkyl.

### Claim 10 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R3 is —CH(CH3)CN, —C(CH3)2CN, methylsulfanylmethyl, methylsulfonylethyl, methylsulfinylmethyl, methylsulfinylethyl, methylsulfonylmethyl or methylsulfonylethyl.

### Claim 11 (depends on 1)

A compound according to claim 1 wherein
X is SO2;
R1 is ethyl;
R2 is trifluoromethyl, pentafluoroethyl or trifluoromethylsulfanyl; and
R4 and R5 are both hydrogen;
or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

### Claim 12 (depends on 1)

A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein A1 is N.

### Claim 13 (depends on 1)

A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1 and, optionally, an auxiliary or diluent.

### Claim 14 (depends on 1)

A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1.

### Claim 15 (depends on 13)

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 a composition according to claim 13.

### Claim 16 (depends on 13)

A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, or a composition as defined in claim 13.