# US 5,350,736 A · Iminothiazolines, their production and use as herbicides, and intermediates for their production

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,350,736 A
- Document ID: US5350736A
- Status: Granted
- Kind: A
- Application number: 07/933,110
- Filed: 1992-08-21
- Granted: 1994-09-27
- Earliest claimed: 1991-08-23
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Shinichi Kawamura; Keiichi Izumi; Junichi Sato; Yuzuru Sanemitsu; Ryo Sato; Tatsuhiro Hamada; Hideyuki Shibata
- Web page: https://patentgrep.com/patent/US5350736A

## CPC

- C07D 277/40: Unsubstituted amino or imino radicals
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- C07D 277/46: by carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D 277/48: by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- 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

There is disclosed an iminothiazoline compound of the formula: ##STR1## wherein R.sup.1 is halogen, halo(lower)alkyl, halo(lower)alkoxy or halo(lower)alkylthio; R.sup.2 is lower alkyl, chlorine; bromine or iodine; R.sup.3 is (lower alkyl)carbonyl, (lower cycloalkyl)carbonyl, (lower cycloalkoxy)carbonyl, (lower alkoxy)carbonyl or (lower alkyl)sulfonyl, all of which are optionally substituted with at least one substituent selected from halogen, lower alkyl, lower alkoxy, lower cycloalkyl and lower cycloalkoxy; and R.sup.4 is halogen. Also disclosed are a process for producing this compound, a herbicidal composition comprising this compound as an active ingredient, and a method for controlling undesired weeds by use of this compound as a herbicide.

## Claims

### Claim 1

An iminothiazoline compound of the formula: ##STR29## wherein R.sup.1 is halogen, halo(lower)alkyl, halo(lower)alkoxy or halo(lower)alkylthio; R.sup.2 is lower alkyl, chlorine, bromine or iodine; R.sup.3 is (lower alkyl)carbonyl, (lower cycloalkyl) carbonyl, (lower cycloalkoxy) carbonyl, (lower alkoxy)carbonyl or (lower alkyl)sulfonyl, all of which are optionally substituted with at least one substituent selected from halogen, lower alkyl, lower alkoxy, lower cycloalkyl and lower cycloalkoxy; and R.sup.4 is halogen.

### Claim 2

An iminothiazoline compound of the formula: ##STR30## wherein R.sup.1 is halogen, halo(C.sub.1 -C.sub.3)alkyl, halo(C.sub.1 -C.sub.3)alkoxy or halo(C.sub.1 -C.sub.3)alkylthio; R.sup.2 is C.sub.1 -C.sub.2 alkyl, chlorine, bromine or iodine; R.sup.3 is C.sub.1 -C.sub.6 alkylcarbonyl, C.sub.3 -C.sub.6 cycloalkylcarbonyl, C.sub.3 -C.sub.6 cycloalkoxycarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl or C.sub.1 -C.sub.6 alkylsulfonyl, all of which are optionally substituted with at least one substituent selected from halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.6 cycloalkyl and C.sub.3 -C.sub.6 cycloalkoxy; and R.sup.4 is halogen.

### Claim 3 (depends on 2)

A compound according to claim 2, wherein is R.sup.4 is present at the para position.

### Claim 4 (depends on 3)

A compound according to claim 3, wherein R.sup.4 is fluorine.

### Claim 5 (depends on 2)

A compound according to claim 2, wherein R.sup.1 is halo(C.sub.1 -C.sub.3)alkyl.

### Claim 6 (depends on 5)

A compound according to claim 5, wherein R.sup.1 is trifluoromethyl.

### Claim 7 (depends on 2)

A compound according to claim 2, wherein R.sup.2 is C.sub.1 -C.sub.2 alkyl.

### Claim 8 (depends on 2)

A compound according to claim 2, wherein R.sup.3 is C.sub.1 -C.sub.6 alkylcarbonyl or C.sub.3 -C.sub.6 cycloalkylcarbonyl, both of which are optionally substituted with at least one substituent selected from halogen, C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 alkoxy.

### Claim 9 (depends on 8)

A compound according to claim 8 wherein R.sup.2 is C.sub.1 -C.sub.2 alkyl.

### Claim 10 (depends on 9)

A compound according to claim 9, wherein R.sup.4 is fluorine at the para position.

### Claim 11 (depends on 1)

A herbicidal composition which comprises as an active ingredient a herbicidally effective amount of the compound according to claim 1, and an inert carrier or diluent.

### Claim 12 (depends on 1)

A method for controlling undesired weeds, which comprises applying a herbicidally effective amount of the compound according to claim 1 and an inert carrier or diluent to the area where undesired weeds grow or will grow.

### Claim 13 (depends on 12)

A method according to claim 12, wherein the compound is applied in the form of a composition.

### Claim 14 (depends on 1)

A compound according to claim 1, wherein R.sup.1 is selected from the ground consisting of --CF.sub.3 and --Cl; R.sup.2 is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5 and --Br; R.sup.3 is selected from the group consisting of --COCH.sub.3, --COCF.sub.3, --CO--i--C.sub.3 H.sub.7, --CO.sub.2 --i--C.sub.3 H.sub.7, ##STR31## --COCHF.sub.2, --CO.sub. C.sub.2 H.sub.5, --COCH.sub.2 --t--C.sub.4 H.sub.9, --CO--n--C.sub.5 H.sub.11, --COCH.sub.2 CH.sub.2 Cl, --COCH.sub.2 OCH.sub.3, ##STR32## --COC.sub.3 F.sub.7, --SO.sub.2 CF.sub.3, --CO.sub.2 --n--C.sub.6 H.sub.13, ##STR33## and --CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ; and R.sup.4 is selected from the group consisting of 4-F, 6-F, and 4-Cl.

### Claim 15 (depends on 1)

A compound according to claim 1, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the following definitions:
______________________________________ R.sup.1 R.sup.2 R.sup.3 R.sup.4 ______________________________________ CF.sub.3 CH.sub.3 COCH.sub.3 4-F CF.sub.3 CH.sub.3 COCF.sub.3 4-F CF.sub.3 CH.sub.3 CO-i-C.sub.3 H.sub.7 4-F CF.sub.3 CH.sub.3 CO.sub.2 -i-C.sub.3 H.sub.7 4-F CF.sub.3 CH.sub.3 COCF.sub.3 6-F CF.sub.3 CH.sub.3 CO.sub.2 -i-C.sub.3 H.sub.7 6-F CF.sub.3 CH.sub.3 COCH.sub.3 4-Cl CF.sub.3 CH.sub.3 COCF.sub.3 4-Cl CF.sub.3 CH.sub.3 ##STR34## 4-Cl CF.sub.3 CH.sub.3 COCHF.sub.2 4-F CF.sub.3 C.sub.2 H.sub.5 COCH.sub.3 4-F CF.sub.3 C.sub.2 H.sub.5 COCF.sub.3 4-F CF.sub.3 C.sub.2 H.sub.5 COCHF.sub.2 4-F Cl Br CO.sub.2 C.sub.2 H.sub.5 4-F CF.sub.3 CH.sub.3 COCH.sub.2 -t-C.sub.4 H.sub.9 4-F CF.sub.3 CH.sub.3 CO-n-C.sub.5 H.sub.11 4-F CF.sub.3 CH.sub.3 COCH.sub.2 CH.sub.2 Cl 4-F CF.sub.3 CH.sub.3 COCH.sub.2 OCH.sub.3 4-F CF.sub.3 CH.sub.3 ##STR35## 4-Cl CF.sub.3 CH.sub.3 COC.sub.3 H.sub.7 4-Cl CF.sub.3 CH.sub.3 SO.sub.2 CF.sub.3 4-Cl CF.sub.3 CH.sub.3 CO.sub.2 -n-C.sub.6 H.sub.13 4-F CF.sub.3 CH.sub.3 ##STR36## 4-F CF.sub.3 CH.sub.3 SO.sub.2 CH.sub.3 4-Cl CF.sub.3 CH.sub.3 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 4-Cl ______________________________________