# US 9,751,865 B2 · Dihydro-hydantoin derivatives with herbicidal activity

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- Number: US 9,751,865 B2
- Document ID: US9751865B2
- Status: Granted
- Kind: B2
- Application number: 15/107,777
- Filed: 2014-12-17
- Published: 2016-11-03
- Granted: 2017-09-05
- Earliest claimed: 2013-12-23
- Assignees: Syngenta Limited
- Applicants: Syngenta Participations AG; Syngenta Limited
- Inventors: James Alan Morris; Ravindra Sonawane; Mangala Phadte; Jake Goodwin-Tindall; Jutta Elisabeth Boehmer; Timothy Robert Desson; Claire Janet Russell; Alan Joseph Hennessy; Matthew Brian Hotson
- Web page: https://patentgrep.com/patent/US9751865B2

## CPC

- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

The invention relates to substituted dihydro-hydantoin derivatives of the formula (I) wherein X, Ra, Rb, Rc, 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 10 to control or inhibit plant growth.

## Claims

### Claim 1

A compound of formula (I)
wherein
X is selected from S and O;
Ra is selected from hydrogen, C1-C6 alkyl and C1-C6 haloalkyl;
Rb is selected from hydrogen, formyl, hydroxyl, halogen, nitro, cyano, C1-C6 alkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C1-C6 haloalkyl, C1-C6 alkylthio, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, C1-C6 alkoxy C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 cyanoalkenyl, C2-C6 cyanoalkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C2-C6 haloalkenyloxy, C2-C6 haloalkynyloxy, C1-C6 alkoxy C2-C6 alkenyl, C1-C6 alkoxy C2-C6 alkynyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfonyloxy, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C2-C6 alkenylcarbonyl, C2-C6 alkynylcarbonyl, C2-C6 haloalkenylcarbonyl, C2-C6 haloalkynylcarbonyl, tri C1-C6 alkylsilyl C2-C6 alkynyl, a group R5R6N—, a group R5C(O)N(R6)—, a group R5R6NC(O)—, a group R5S(O2)N(R6)—, a group R5R6NSO2—, a C6-C10 aryl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C6-C10 aryloxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C6-C10 benzyl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C6-C10 benzyloxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C3-C6 heterocyclyl group optionally substituted by from 1 to 3 groups independently selected from C1-C4 alkyl and a C3-C6 cycloalkyl group optionally substituted with from 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
Rc is selected from hydrogen, halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl;
or Ra and Rb together with the nitrogen and carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl;
or Rb and Rc together with the carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl;
R1 is selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 haloalkyl;
R2 is selected from hydrogen, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 haloalkyl, C1-C3 haloalkoxy and C1-C4 cyanoalkyl;
or R1 and R2 together with the nitrogen and carbon atoms to which they are attached form a 3-7 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 or C1-C6 haloalkyl;
R3 is selected from halogen, hydroxyl, —NR10R11 and any one of the following groups
R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl and C2-C6 alkynyl;
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 and a C6-C10 aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 or R7 and R8 together with the atoms to alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, or R7 and R8 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 and benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy; and
R10 and R11 are, independently, selected from hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C2-C20 alkenyl and C2-C20 alkynyl.

### 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 Ra is selected from hydrogen, methyl and ethyl or Ra and Rb together with the nitrogen and carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Rb is selected from hydrogen, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C5 alkenyl, a C6-C10 aryl group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy and a C3-C6 heteroaryl group optionally substituted by from 1 to 3 groups independently selected from C1-C4 alkyl, or Ra and Rb together with the nitrogen and carbon atoms to which they are attached form a 3-7 membered saturated or partially unsaturated ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from C1-C6 alkyl or Rb and Rc together with the carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl.

### Claim 5 (depends on 4)

The compound of claim 4, wherein Rb is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl and C1-C4 alkoxy.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Rc is selected from hydrogen, methyl and cyano or Rb and Rc together with the carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R1 is selected from C1-C4 alkyl, C1-C4 alkoxy and C1-C4 haloalkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R2 is selected from hydrogen, hydroxyl, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkoxy-C1-C3 alkyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R3 is selected from hydroxyl, halogen, C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy and C6-C10 aryloxycarbonyloxy wherein the aryl group may be substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy.

### Claim 10 (depends on 1)

The compound of claim 1, wherein X is O, R1 is selected from hydrogen, C1-C3 alkyl and C1-C3 alkoxy, R2 is selected from hydrogen, hydroxyl, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkoxy-C1-C3 alkyl, R3 is hydroxyl, Ra is C1-C3 alkyl, Rb is selected from C1-C4 alkyl and C1-C3 haloalkyl or Ra and Rb together with the nitrogen and carbon atoms to which they are attached form a 3-7 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, C1-C6 alkyl and C1-C6 haloalkyl and Rc is selected from hydrogen and cyano.

### Claim 11 (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 12 (depends on 11)

A composition according to claim 11 further comprising an herbicide in addition to the compound of formula I.

### Claim 13 (depends on 11)

A composition according to claim 11 further comprising a safener.

### 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.