IP Library Granted Patent US 9,174,987
Granted Patent B2
US 9,174,987 · App. 13/234,793 · Granted Nov 3, 2015

Spiroindolinepiperidine derivatives

Inventors: David John Hughes (Bracknell, GB); Paul Anthony Worthington (Bracknell, GB); Charles Adam Russell (Bracknell, GB); Eric Daniel Clarke (Bracknell, GB); James Edward Peace (Bracknell, GB); Mark Richard Ashton (Abington, GB); Thomas Stephen Coulter (Abington, GB); Richard Spurring Roberts (Barcelona, ES); Louis-Pierre Molleyres (Basel, CH); Fredrik Cederbaum (Stein, CH); Jerome Cassayre (Stein, CH); Peter Maienfisch (Stein, CH)
Assignees: Syngenta Limited; Syngenta Participations AG
C07D471/10A01N43/90A01N47/34A01N47/38C07D211/70C07D211/76C07D491/10C07B2200/11
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Quick Facts
Patent No.
US 9,174,987
App. No.
13/234,793
Granted
Nov 3, 2015
Kind
B2
Abstract

Insecticidal, acaricidal, nematicidal or molluscicidal compounds of formula (I) wherein Y is a single bond, C═O, C═S or S(O) q where q is 0, 1 or 2; and R 1 , R 2 , R 3 , R 4 , R 8 , R 9 are R 10 are as defined in the claims or salts or N-oxides thereof, processes for preparing them and compositions containing them.

Claims (75)

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):

wherein

Y is a single bond,

C═O or

SO 2 ;

R 1 is hydrogen,

C 1-6 alkyl,

C 1-6 haloalkyl,

C 1-6 alkoxy(C 1-6 )alkyl,

heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted by halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy),

phenyl(C 1-6 )alkyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN),

phenyl (which is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN),

heteroaryl (which is optionally substituted by halogen, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy),

C 1-6 alkoxy,

C 1-6 haloalkoxy,

C 2-6 alkenyl,

C 3-6 cycloalkyl,

heterocyclyl (which is optionally substituted by halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy or C 1-6 haloalkoxy), or

NR 13 R 14 where

R 13 and R 14 are independently hydrogen,

C 2-6 alkyl,

C 2-6 haloalkyl,

phenyl (which is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, or CN) or

heteroaryl (which is optionally substituted by halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, or C 1-6 haloalkoxy);

R 2 and R 3 are independently hydrogen or C 1-4 alkyl;

each R 4 is independently halogen,

cyano,

C 1-8 alkyl,

C 1-8 haloalkyl,

C 1-6 alkoxy(C 1-6 )alkyl,

C 2-6 alkynyl,

C 1-6 alkoxycarbonyl,

C 3-7 cycloalkyl,

C 1-3 alkyl (C 3-7 ) cycloalkyl,

phenyl (which is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, or CN),

heterocyclyl (which is optionally substituted by halogen,

nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy or C 1-6 haloalkoxy),

C 1-8 alkoxy, or

C 1-6 haloalkoxy,

n is 0, 1, 2, 3 or 4;

R 8 is C 1-6 alkyl,

C 1-6 haloalkyl,

phenyl(C 1-4 )alkyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , phenyl, heteroaryl, amino or dialkylamino),

heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , phenyl, heteroaryl, amino or dialkylamino),

C 2-6 alkenyl,

phenyl(C 2-6 )alkenyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , phenyl, heteroaryl, amino or dialkylamino),

C 2-6 alkynyl,

phenyl(C 2-6 )alkynyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , phenyl, heteroaryl, amino or dialkylamino); or

—C(R 51 )(R 52 )—[CR 53 ═CR 54 ]z-R 55 where

z is 1 or 2,

R 51 and R 52 are each independently H, or C 1-2 alkyl,

R 53 and R 54 are each independently H, halogen, or C 1-4 alkyl and

R 55 is phenyl (wherein the phenyl group is optionally substituted by one or more substituents independently selected from halogen) or

heteroaryl (wherein the heteroaryl group is optionally substituted by one or more substituents independently selected from halogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 3-7 cycloalkyl, nitro, or cyano);

R 9 and R 10 are independently hydrogen, or C 1-2 alkyl;

and salts or N-oxides thereof.

2. The method according to claim 1 wherein

Y is C═O.

3. The method according to claim 1 wherein

R 1 is pyridyl (which is optionally substituted by halo, C 1-3 alkyl or C 1-3 haloalkyl) or C 1-6 alkoxy.

4. The method according to claim 1 wherein

R 2 and R 3 are both hydrogen.

5. The method according to claim 1 wherein each R 4 is independently fluoro, chloro, bromo, C 1-4 alkyl or C 1-4 haloalkyl; n is 1 or 2.

6. The method according to claim 1 wherein

R 8 is —C(R 51 )(R 52 )—[CR 53 ═CR 54 ]z-R 55 where z is 1 or 2, R 51 and R 52 are each independently H, or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, or C 1-4 alkyl and R 55 is phenyl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, or NO 2 , or heteroaryl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, or NO 2 .

7. The method according to claim 1 wherein

R 9 and R 10 are both hydrogen.

8. The method according to claim 1 wherein

Y is C═O;

R 1 is pyridyl (which is optionally substituted by halogen, C 1-3 alkyl or C 1-3 haloalkyl) or C 1-6 alkoxy;

R 2 and R 3 are independently hydrogen or

methyl;

each R 4 is independently fluoro, chloro, bromo, C 1-4 alkyl or C 1-4 haloalkyl; n is 1 or 2;

R 8 is —C(R 51 )(R 52 )—[CR 53 ═CR 54 ]z-R 55 where z is 1 or 2, R 51 and R 52 are each independently H, or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, or C 1-4 alkyl and R 55 is phenyl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, or NO 2 , or heteroaryl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, or NO 2 ; and

R 9 and R 10 are both hydrogen.

Priority Claims (1)
GB 0213715.6 · Jun 14, 2002 · national
Continuity (2)
Division 10517957
Related Publication 20120010220A1 · Jan 12, 2012