Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-10499640-B2
Application number	US-201515524936-A
Country	US
Kind code	B2
Filing date	Nov 3, 2015
Priority date	Nov 7, 2014
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

The invention relates to substituted pyrrolone derivatives of the formula (I) wherein X, A, R 1 , R 2 and R 3 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 or inhibit plant growth.

First claim

The invention claimed is:

1. A compound of formula (I)

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

R b is selected from unsubstituted C 1 -C 6 alkyl or substituted C 1 -C 6 alkyl substituted with one or more groups independently selected from hydroxyl, halogen, cyano and C 1 -C 6 alkoxy;
R c is selected from hydrogen, halogen, cyano, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 1 is selected from hydrogen, C 1 -C 6 alkyl optionally substituted with NR 10 R 11 , C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy and C 2 -C 6 alkynyl; wherein R 10 and R 11 are independently selected from hydrogen, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 2 is selected from hydrogen, hydroxyl, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, and the group NR 12 R 13 wherein R 12 and R 13 are independently selected from hydrogen and C 1 -C 6 ;
or R 1 and R 2 together with the nitrogen and carbon atoms to which they are attached form a 3-5 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 hydroxyl, ═O, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 3 is selected from halogen, hydroxyl, —NR 5 R 6 , or any one of the following groups

R 5 and R 6 are, independently, selected from hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 2 -C 20 alkenyl and C 2 -C 20 alkynyl, 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 and 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, a C 5 -C 10 heteroaryl group which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S and 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, a C 6 -C 10 aryl group 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 9 together with the 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;
or an N-oxide or salt form thereof;
with the provisos that
(i) when R 1 is methyl, A is

R b is C 1 -C 6 cyanoalkyl or C 1 -C 6 haloalkyl then R 2 is not C 1 -C 4 alkoxy or C 1 -C 4 alkoxy-C 1 -C 4 -alkyl;

(ii) when R 1 is C 1 -C 3 alkyl, R 2 is hydrogen, hydroxyl, methyl or allyl, R b is not substituted C 1 -C 6 alkyl substituted by halogen or C 1 -C 6 alkoxy;
(iii) when R 1 is C 1 -C 3 alkyl, R 2 is H, A is

then R b is not substituted C 1 -C 6 alkyl substituted by halogen;

(iv) R b can only be unsubstituted C 1 -C 6 alkyl when R 1 or R 2 is C 2 -C 6 alkynyl, or one of R 1 or R 2 is C 2 or C 3 alkyl and the other is not H, or R 1 and R 2 together form a 3-5 membered ring structure; and
(v) when R 1 is hydrogen, methyl, R 1 is hydrogen, and R c is hydrogen, chlorine or bromine, R b is not substituted alkyl substituted by halogen.

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

3. The compound of claim 1 , wherein R c is hydrogen.

4. The compound of claim 1 , wherein R 3 is selected from halogen, hydroxyl, —NR 5 R 6 or any of the following groups

5. The compound of claim 1 , wherein R b is —C(CH 3 ) 2 Y and wherein Y is selected from halogen, hydroxyl, cyano and C 1 -C 6 alkoxy.

6. The compound of claim 5 , wherein R 1 is selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkyl or R 1 and R 2 together with the nitrogen and carbon atoms to which they are attached form a 3-5 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 hydroxyl, ═O, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl.

7. The compound of claim 5 , wherein R 2 is selected from hydrogen, hydroxyl, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 alkoxy-C 1 -C 3 alkyl or R 1 and R 2 together with the nitrogen and carbon atoms to which they are attached form a 3-5 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 hydroxyl, ═O, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl.

8. The compound of claim 1 , wherein (i) at least one of R 1 and R 2 is C 2 -C 6 alkynyl or (ii) one of R 1 or R 2 is C 2 or C 3 alkyl and the other is not H, or (iii) R 1 and R 2 together with the nitrogen and carbon atoms to which they are attached form a 3-5 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 hydroxyl, ═O, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl.

9. The compound of claim 8 , wherein R b is —C(CH 3 ) 3 .

10. A herbicidal composition comprising a compound of formula (I) as defined in claim 1 together with at least one agriculturally acceptable adjuvant or diluent.

11. The composition according to claim 10 which comprises a further herbicide in addition to the compound of formula (I).

12. The composition according to claim 10 which comprises a safener.

13. The compound of claim 1 , wherein when R 1 is C 1 -C 3 alkyl or hydrogen, R 2 is hydrogen, hydroxyl, methyl or allyl, R b is not C 1 -C 6 alkyl substituted by halogen or C 1 -C 6 alkoxy.

14. A method of controlling weeds in crops of useful plants, comprising applying to said weeds or to the locus of said weeds, or to said useful plants or to the locus of said useful plants, a compound of formula (I) as defined in claim 1 .

Assignees

• Syngenta Participations Ag

Inventors

• Morris James Alan
• PHADATE Mangala
• Sonawane Ravindra
• Russell Claire Janet
• Moseley Donn Warwick
• Longstaff Adrian
• Hotson Matthew Brian
• Hennessy Alan Joseph

Classifications

• C07D413/04

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

• A01N43/80 Primary

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title