# US 10,499,640 B2 · Herbicidal compounds

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- Number: US 10,499,640 B2
- Document ID: US10499640B2
- Status: Granted
- Kind: B2
- Application number: 15/524,936
- Filed: 2015-11-03
- Published: 2017-11-09
- Granted: 2019-12-10
- Earliest claimed: 2014-11-07
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: James Alan Morris; Mangala Phadate; Ravindra Sonawane; Claire Janet Russell; Donn Warwick Moseley; Adrian Longstaff; Matthew Brian Hotson; Alan Joseph Hennessy
- Web page: https://patentgrep.com/patent/US10499640B2

## CPC

- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to substituted pyrrolone derivatives of the formula (I) wherein X, A, R1, R2 and R3 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.

## Claims

### Claim 1

A compound of formula (I)
wherein
X is selected from S and O;
A is:
Rb is selected from unsubstituted C1-C6 alkyl or substituted C1-C6 alkyl substituted with one or more groups independently selected from hydroxyl, halogen, cyano and C1-C6alkoxy;
Rc is selected from hydrogen, halogen, cyano, C1-C6 alkyl and C1-C6haloalkyl;
R1 is selected from hydrogen, C1-C6 alkyl optionally substituted with NR10R11, C1-C3 haloalkyl, C1-C6 alkoxy and C2-C6 alkynyl; wherein R10 and R11 are independently selected from hydrogen, C1-C6 alkyl and C1-C6 haloalkyl;
R2 is selected from hydrogen, hydroxyl, halogen, C1-C6 alkyl, C2-C6alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy C1-C6 alkyl, and the group NR12R13 wherein R12 and R13 are independently selected from hydrogen and C1-C6;
or R1 and R2 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, C1-C6 alkyl and C1-C6 haloalkyl;
R3 is selected from halogen, hydroxyl, —NR5R6, or any one of the following groups
R5 and R6 are, independently, selected from hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C2-C20 alkenyl and C2-C20 alkynyl, or R5 and R6 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 C1-C6 alkyl;
R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, a C5-C10 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, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 alkoxy, a C6-C10 aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3haloalkoxy, or R7 and R9 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 C1-C6 alkyl;
R9 is selected from C1-C6 alkyl or benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy;
or an N-oxide or salt form thereof;
with the provisos that
(i) when R1 is methyl, A is
Rb is C1-C6 cyanoalkyl or C1-C6 haloalkyl then R2 is not C1-C4 alkoxy or C1-C4 alkoxy-C1-C4-alkyl;
(ii) when R1 is C1-C3 alkyl, R2 is hydrogen, hydroxyl, methyl or allyl, Rb is not substituted C1-C6 alkyl substituted by halogen or C1-C6 alkoxy;
(iii) when R1 is C1-C3 alkyl, R2 is H, A is
then Rb is not substituted C1-C6 alkyl substituted by halogen;
(iv) Rb can only be unsubstituted C1-C6 alkyl when R1 or R2 is C2-C6 alkynyl, or one of R1 or R2 is C2 or C3 alkyl and the other is not H, or R1 and R2 together form a 3-5 membered ring structure; and
(v) when R1 is hydrogen, methyl, R1 is hydrogen, and Rc is hydrogen, chlorine or bromine, Rb is not substituted alkyl substituted by halogen.

### Claim 2 (depends on 1)

The compound of claim 1, wherein X is O.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Rc is hydrogen.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R3 is selected from halogen, hydroxyl, —NR5R6 or any of the following groups

### Claim 5 (depends on 1)

The compound of claim 1, wherein Rb is —C(CH3)2Y and wherein Y is selected from halogen, hydroxyl, cyano and C1-C6 alkoxy.

### Claim 6 (depends on 5)

The compound of claim 5, wherein R1 is selected from C1-C3alkyl, C1-C3 alkoxy and C1-C3 haloalkyl or R1 and R2 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, C1-C6 alkyl and C1-C6haloalkyl.

### Claim 7 (depends on 5)

The compound of claim 5, wherein R2 is selected from hydrogen, hydroxyl, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkoxy-C1-C3 alkyl or R1 and R2 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, C1-C6 alkyl and C1-C6 haloalkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein (i) at least one of R1 and R2 is C2-C6 alkynyl or (ii) one of R1 or R2 is C2 or C3 alkyl and the other is not H, or (iii) R1 and R2 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, C1-C6 alkyl and C1-C6 haloalkyl.

### Claim 9 (depends on 8)

The compound of claim 8, wherein Rb is —C(CH3)3.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 10)

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

### Claim 12 (depends on 10)

The composition according to claim 10 which comprises a safener.

### Claim 13 (depends on 1)

The compound of claim 1, wherein when R1 is C1-C3 alkyl or hydrogen, R2 is hydrogen, hydroxyl, methyl or allyl, Rb is not C1-C6 alkyl substituted by halogen or C1-C6 alkoxy.

### Claim 14 (depends on 1)

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.