Chemical compounds

Patent metadata

Field	Value
Publication number	US-9963445-B2
Application number	US-201314906073-A
Country	US
Kind code	B2
Filing date	Aug 5, 2013
Priority date	Aug 5, 2013
Publication date	May 8, 2018
Grant date	May 8, 2018

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 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, 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, a 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 and a C 3 -C 6 heterocyclyl group optionally substituted by from 1 to 3 groups independently selected from C 1 -C 4 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, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, a group R 5 R 6 N— and, when R b is other than hydrogen, 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 selected from chlorine, bromine and C 1 -C 3 alkoxy;
R 2 is selected from C 1 -C 6 alkyl, or C 1 -C 6 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 1 -C 6 cyanoalkyl, C 1 -C 6 cyanocycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl, or R 5 and R 6 together with the carbon atoms to which they are attached form a 3-6 membered 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 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;
or an N-oxide or salt form thereof.

2. The compound of claim 1 , wherein X is O.

3. The compound of claim 1 , wherein A is

4. The compound of claim 1 , wherein R a is selected from hydrogen and fluorine.

5. The compound of claim 1 , wherein R b is selected from hydrogen, halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy C 2 -C 6 alkenyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, a group R 10 O(O)C—, a group R 5 R 6 NC(O)—, a group R 5 C(O)N(R 6 )—, 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, a 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 3 -C 6 heterocyclyl group optionally substituted by from 1 to 3 groups independently selected from C 1 -C 4 alkyl.

6. The compound

Assignees

• Syngenta Participations Ag
• Syngenta Ltd

Inventors

• Clough John Martin
• Boehmmer Jutta Elisabeth
• 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
• Dowling Alan John

Classifications

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• G02B7/025

  using glue · CPC title

• A01N43/58

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

• A01N43/40

  six-membered rings · CPC title