# US 7,612,018 B2 · Insecticides

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- Number: US 7,612,018 B2
- Document ID: US7612018B2
- Status: Granted
- Kind: B2
- Application number: 11/575,436
- Filed: 2005-09-20
- Published: 2008-09-04
- Granted: 2009-11-03
- Earliest claimed: 2004-09-21
- Assignees: Syngenta Crop Protection AG
- Inventors: Andre Jeanguenat; Anthony Cornelius O'Sullivan
- Web page: https://patentgrep.com/patent/US7612018B2

## CPC

- A01N 47/24: containing the groups [IMAGE cpc-sch-A01N-0944.gif], [IMAGE cpc-sch-A01N-0945.gif] or[IMAGE cpc-sch-A01N-0946.gif]; Thio analogues thereof
- A01N 41/02: containing a sulfur-to-oxygen double bond
- A01N 41/10: Sulfones; Sulfoxides
- C07C 381/10: Compounds containing sulfur atoms doubly-bound to nitrogen atoms
- 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 and all stereoisomers and tautomeric forms of the compounds of formula I can be used as agrochemical active ingredients and can be prepared in a manner known per se.

## Claims

### Claim 1

A compound of formula I
wherein
n is 0 or 1;
R1 is halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylsulfonyloxy, C1-C8haloalkylsulfonyloxy or —OSO2F;
each of R2 and R3, which may be the same or different, represents hydrogen, halogen, cyano, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C8alkylsulfonyloxy, C1-C8haloalkylsulfonyloxy, —OSO2F;
or R2 together with R3 form a C2-C6alkylene or C3-C6alkenylene bridge which may be interrupted by nitrogene, oxygene and/or —C(O)—, or by —S(O)m—;
and said bridge may be mono- or poly-substituted by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, amino, hydroxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C1-C4alkylcarbonyl-C1-C3alkylthio, C1-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro and/or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C1-C4alkylcarbonyl-C1-C3alkylthio, C1-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano or nitro, and the substituents at the nitrogen atom in said bridge being other than halogen, and two oxygen atoms not being located next to one another;
m is 0, 1 or 2;
each of S1 and S2, which may be the same or different, represents hydrogen, halogen, cyano, nitro, C1-C8alkyl, C1-C8haloalkyl, C1-C8alkoxy, C1-C8haloalkoxy, C1-C8alkenyl, C2-C8haloalkenyl, C1-C8alkynyl, C2-C8haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl, C1-C8haloalkylsulfonyl, C1-C6alkylamino or di-(C1-C6alkyl)amino, whose C1-C6alkyl groups may be the same or different;
S3 is cyano, C1-C6alkyl, halo-C1-C6alkyl, C1-C6alkoxy, halo-C1-C6alkoxy, halo-C1-C6alkoxyhalo-C1-C6alkoxy, C1-C8alkylthio, C1-C8haloalkylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C1-C8alkylsulfonyl or C1-C8haloalkylsulfonyl; or
S3 is a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the phenyl ring directly or via a —O—, —S—, C1-C4alkylene, —CH═CH—, —C≡C—, —CH2O—, —CH2N(C1-C4alkyl)-, —CH2SO—, or —CH2SO2 group and it not being possible for each ring system to contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di-(C1-C2alkyl)aminosulfonyl, di-(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen;
each of R4 and R5, which may be the same or different, represents hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
Y1 is a C1-C6alkylene, C2-C6alkenylene or C3-C6alkynylene chain which may be mono-, di- or trisubstituted by R9, where the unsaturated bonds of the chain are not attached directly to the sulfur atom; or is C3-C6cycloalkylene, which may be mono-, di- or trisubstituted by R10;
R9 and R10 independently of one another are halogen, nitro, cyano, hydroxy, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy, C1-C6halo-alkoxy, benzyl or phenyl, where phenyl and benzyl for their part may be mono- or polysubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;
Y2 is a C1-C6alkylene, C2-C6alkenylene or C3-C6alkynylene chain which may be mono-, di- or trisubstituted by R11, where the unsaturated bonds of the chain are not attached directly to the sulfur atom; or is C3-C6cycloalkylene, which may be mono-, di- or trisubstituted by R12;
R11 and R12 independently of one another are halogen, nitro, cyano, hydroxy, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy, C1-C6halo-alkoxy, benzyl or phenyl, where phenyl and benzyl for their part may be mono-, di- or trisubstituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxyl or nitro;
Y3 is hydrogen or C1-C6alkyl;
Z is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio or C1-C6alkoxy-C1-C6alkyl; or C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkoxy, or C1-C6haloalkoxy; or Z is —C(O)R6, —C(O)O—R7, —CONR13R14, —SO2R15 or —OP(OR16)(OR17)—OR18;
R6 is C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl or C1-C6alkoxy-C1-C6alkyl; or
C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkoxy, or C1-C6haloalkoxy; R7, R13, R14, R15, R16, R17 and R18 independently of one another are C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl or C1-C6halocycloalkyl; or C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl or C1-C6halocycloalkyl substituted by C1-C6alkyl, C1-C6haloalkyl, C1-C6cycloalkyl, C1-C6halocycloalkyl, C1-C6alkoxy or C1-C6haloalkoxy; and
agronomically acceptable salts/isomers/enantiomers/tautomers of those compounds.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein Z is hydrogen, —C(O)R6, —C(O)O—R7, —CONR13R14, —SO2R15 or —OP(OR16)(OR17)—OR18.

### Claim 3 (depends on 1)

A pesticidal composition, which comprises at least one compound according to claim 1 of the formula I 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.

### Claim 4 (depends on 3)

A composition according to claim 3 for controlling insects or representatives of the order Acarina.

### Claim 5 (depends on 3)

A method for controlling pests, which comprises applying a composition according to claim 3 to the pests or their environment.

### Claim 6 (depends on 5)

A method according to claim 5 for controlling insects or representatives of the order Acarina.

### Claim 7 (depends on 5)

A method according to claim 5 for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted.

### Claim 8 (depends on 7)

Plant propagation material treated in accordance with the method described in claim 7.