# US 4,400,199 A · Thiolcarbamate compounds and their use as herbicides

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- Number: US 4,400,199 A
- Document ID: US4400199A
- Status: Granted
- Kind: A
- Application number: 06/316,305
- Filed: 1981-10-29
- Granted: 1983-08-23
- Earliest claimed: 1981-10-29
- Assignees: Asahi Kasei Kabashiki Kaisha
- Inventors: Shigeo Yokoyama; Teruyuki Misumi; Einosuke Fujimoto; Yutaka Kobayashi
- Web page: https://patentgrep.com/patent/US4400199A

## CPC

- C07D 295/21: Radicals derived from sulfur analogues of carbonic acid
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N 47/16: the nitrogen atom being part of a heterocyclic ring
- C07D 211/16: with acylated ring nitrogen atom
- C07D 223/04: with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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

Chloroalkylthiolcarbamate compounds of the formula: ##STR1## wherein Z represents ##STR2## and when Z is ##STR3## n is an integer of 4 to 10, whereas when Z is ##STR4## n is an integer of 3 to 10. These compounds are useful as effective herbicides having no harmful effect on the ecosystem, particularly extremely low toxicity to fish, and can be obtained, for example, by reacting the corresponding thiolcarbamate derivatives with a chloroalkyl halide.

## Claims

### Claim 1

A compound represented by the formula ##STR42## wherein Z represents ##STR43## and when Z is ##STR44## n is an integer of 4 to 10, whereas when Z is ##STR45## n is an integer of 3 to 10.

### Claim 2

S-(4-chlorobutyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate.

### Claim 3

S-(3-chloropropyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate.

### Claim 4

S-(4-chlorobutyl)-(2-methyl)-piperidine-1-carbothioate.

### Claim 5

A herbicidal composition which comprises as an active ingredient a herbicidally effective amount of a compound represented by the formula ##STR46## wherein Z represents ##STR47## and when Z is ##STR48## n is an integer of 4 to 10, whereas when Z is ##STR49## n is an integer of 3 to 10 and an agriculturally acceptable carrier.

### Claim 6 (depends on 5)

A herbicidal composition according to claim 5, wherein said compound is selected from the group consisting of
S-(4-chlorobutyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate,
S-(3-chloropropyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate and
S-(4-chlorobutyl)-(2-methyl)-piperidine-1-carbothioate.

### Claim 7 (depends on 5)

A herbicidal composition according to claim 5, wherein said compound is contained in an amount of 0.1 to 99% by weight based on the composition.

### Claim 8

A method for the destruction of undesirable weeds which comprises applying to said weeds a herbicidal amount of a compound represented by the formula ##STR50## wherein Z represents ##STR51## and when Z is ##STR52## n is an integer of 4 to 10, whereas when Z is ##STR53## n is an integer of 3 to 10.

### Claim 9 (depends on 8)

A method according to claim 8, wherein said compound is selected from the group consisting of
S-(4-chlorobutyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate,
S-(3-chloropropyl)-3,6-dimethyl-hexahydro-1H-azepine-1-carbothioate and
S-(4-chlorobutyl)-(2-methyl)-piperidine-1-carbothioate.

### Claim 10 (depends on 8)

A method according to claim 8, wherein said herbicidal amount is within the range of 10 g to 1000 g of said compound per 10 ares.