Chemical compounds

Patent metadata

Field	Value
Publication number	US-9611248-B2
Application number	US-201314906138-A
Country	US
Kind code	B2
Filing date	Aug 5, 2013
Priority date	Aug 5, 2013
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

The invention relates to pyrrolone compounds of the formula (I)

wherein X, R 1 , R 2 , R 3 and A are as defined in the specification. Furthermore, the present invention relates to processes and intermediates for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control plant growth.

First claim

The invention claimed is:

1. A herbicidal compound of the formula (I)

wherein
X is selected from S and O;
A is selected from

R a is selected from hydrogen and halogen;
R b is selected from hydrogen, formyl, hydroxyl, halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cyanocycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxy, C 1 -C 6 alkthio C 1 -C 6 alkyl, aryl C 1 -C 6 alkylthio, C 3 -C 6 cycloalkoxy, aryl C 1 -C 6 alkoxy, aryl C 1 -C 6 alkoxy C 1 -C 6 alkoxy, C 1 -C 6 cyanoalkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 cyanoalkenyl, C 2 -C 6 cyanoalkynyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 2 -C 6 haloalkenyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkoxy C 2 -C 6 alkenyl, C 1 -C 6 alkoxy C 2 -C 6 alkynyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, a group R 10 O(O)C—, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 haloalkenylcarbonyl, C 2 -C 6 haloalkynylcarbonyl, C 1 -C 6 alkoxycarbonyloxy, C 1 -C 6 alkenyloxycarbonyloxy, C 1 -C 6 alkynyloxycarbonyloxy, C 1 -C 6 haloalkoxycarbonyloxy, tri C 1 -C 6 alkylsilyl C 2 -C 6 alkynyl, a group R 5 R 6 N—, a group R 5 C(O)N(R 6 )—, a group R 5 S(O 2 )N(R 6 )—, a group R 5 R 6 NC(O)—, a group R 5 R 6 NC(O)O—, a group R 5 R 6 NSO 2 —, a C 6 -C 10 aryl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy and C 1 -C 6 alkyl S(O 2 )— or any two groups on adjacent carbon atoms together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N; a C 5 -C 10 heteroaryl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; a C 6 -C 10 aryloxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; a C 6 -C 10 benzyl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; a C 6 -C 10 benzyloxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; a C 3 -C 6 heterocyclyl group optionally substituted by from 1 to 3 groups independently selected from C 1 -C 4 alkyl; a C 5 -C 10 heteroaryl C 1 -C 6 alkoxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; a heterocyclyl C 1 -C 6 alkoxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; and a C 3 -C 6 cycloalkyl ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen or C 1 -C 6 alkyl; or R b and R c together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen or C 1 -C 6 alkyl;
R c is selected from hydrogen, formyl, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cyanocycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 cyanoalkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 cyanoalkenyl, C 2 -C 6 cyanoalkynyl, C 2 -C 6 alkenyloxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 2 -C 6 haloalkenyloxy, C 1 -C 6 alkthio C 1 -C 6 alkyl, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, a group R 5 R 6 N— and, when R b is other than hydrogen or methyl, nitro; or R b and R c together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen or C 1 -C 6 alkyl;
R d is selected from hydrogen, cyano and halogen;
R 1 is C 1 -C 6 alkyl or C 1 -C 3 alkoxy and R 2 is chlorine or bromine, C 2 -C 6 alkenyloxy, C 1 -C 6 haloalkyloxy or C 1 -C 3 alkoxy with the proviso that R 1 and R 2 are not both C 1 -C 3 alkoxy;
R 3 is selected from halogen, hydroxyl, or any one of the following groups

R 5 and R 6 are independently selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl C 1 -C 6 alkyl, or R 5 and R 6 together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen or C 1 -C 6 alkyl;
R 7 and R 8 are independently selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl; 5 to 10 membered heteroaryl which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S, optionally substituted with 1 to 3 groups independently selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 1 -C 3 alkoxy; C 6 -C 10 aryl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy; or R 7 and R 8 together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen or C 1 -C 6 alkyl;
R 9 is selected from C 1 -C 6 alkyl or benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, and C 1 -C 3 haloalkoxy;
R 10 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;
with the provisos that (i) if R b is methylthio, methoxy, methoxycarbonyl, fluorine or trifluoromethyl and R 2 is chlorine or bromine, R c cannot be hydrogen and (ii) if R b is tri C 1 -C 6 alkylsilyl C 2 -C 6 alkynyl, R 2 cannot be chlorine or bromine;
or an N-oxide or salt fo

Assignees

• Syngenta Participations Ag
• Syngenta Ltd

Inventors

• Dowling Alan John
• Clough John Martin
• Boehmer Jutta Martin
• Phadte Mangala
• Sonawane Ravindra
• Longstaff Adrian
• Morris James Alan
• Desson Timothy Robert
• Hotson Matthew Brian
• Russell Sally
• Ling Kenneth
• Barnett Susan Patricia
• Bacon David Philip
• Moseley Donn Warwick
• Mound William Roderick

Classifications

• A01N43/40

  six-membered rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• A01N43/58

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title