# US 4,398,940 A · N-Amides of 2-benzothiazolinone

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- Number: US 4,398,940 A
- Document ID: US4398940A
- Status: Granted
- Kind: A
- Application number: 06/311,359
- Filed: 1981-10-15
- Granted: 1983-08-16
- Earliest claimed: 1977-12-16
- Assignees: Monsanto Company
- Inventors: John J. D'Amico
- Web page: https://patentgrep.com/patent/US4398940A

## CPC

- C07D 277/68: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- 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

N-amides of 2-benzothiazolinone have been found to be effective in regulating the growth of leguminous plants.

## Claims

### Claim 1

A method of regulating the growth of leguminous plants which comprises applying to the plant locus an effective plant growth regulating amount of an N-amide of 2-benzothiazolinone having the formula ##STR28## wherein T is trifluoromethyl and halo, n is 0 or 1; m is an integer from one to four; and R is selected from the group consisting of ##STR29## wherein X and Y are independently selected from the group consisting of hydrogen, halogen, lower alkyl and trifluoromethyl; R.sub.1 is hydrogen or lower alkyl; and (II) heterocyclics selected from the group consisting of morpholino, cis- and trans-2,6-dimethylmorpholino, cis- and trans-2,5-dimethylpyrrolidino, 3-azabicyclo (3.2.2) nonyl, and ethyl N-piperazinocarboxylate.

### Claim 2 (depends on 1)

A method according to claim 1 wherein R is ##STR30##

### Claim 3 (depends on 2)

A method according to claim 2 wherein R.sub.1 is hydrogen.

### Claim 4 (depends on 1)

A method according to claim 1 wherein m is one.

### Claim 5 (depends on 4)

A method according to claim 4 wherein R is ##STR31##

### Claim 6 (depends on 5)

A method according to claim 5 wherein R.sub.1 is hydrogen.

### Claim 7 (depends on 1)

A method according to claim 1 wherein R is a heterocyclic selected from the group consisting of morpholino, cis- and trans-2,6-dimethylmorpholino, cis- and trans-2,5-dimethylpyrrolidino, 3-azabicyclo (3.2.2) nonyl, and ether N-piperazinocarboxylate.

### Claim 8 (depends on 7)

A method according to claim 7 wherein m is one.

### Claim 9

A plant growth regulating composition which comprises from about 5 to about 95 parts by weight of a 2-oxo 3-benzothiazolineacetamide having the formula ##STR32## wherein T is trifluoromethyl and halo, n is 0 or 1; m is an integer from one to four; and R is selected from the group consisting of ##STR33## wherein X and Y are independently selected from the group consisting of hydrogen, halogen, lower alkyl and trifluoromethyl; R.sub.1 is hydrogen or lower alkyl; and (II) heterocyclics selected from the group consisting of morpholino, cis- and trans-2,6-dimethylmorpholino, cis- and trans-2,5-dimethylpyrrolidino, 3-azabicyclo (3.2.2) nonyl, and ethyl N-piperazinocarboxylate; the remaining parts being composed of one or more suitable carriers, diluents and/or adjuvants.

### Claim 10 (depends on 9)

A composition according to claim 9 wherein R is ##STR34##

### Claim 11 (depends on 10)

A composition according to claim 10 wherein R.sub.1 is hydrogen.

### Claim 12 (depends on 9)

A composition according to claim 9 wherein m is one.

### Claim 13 (depends on 12)

A composition according to claim 12 wherein R is ##STR35##

### Claim 14 (depends on 13)

A composition according to claim 13 wherein R.sub.1 is hydrogen.

### Claim 15 (depends on 9)

A composition according to claim 9 wherein R is a heterocyclic selected from the group consisting of morpholino, cis- and trans-2,6-dimethylmorpholino, cis- and trans-2,5-dimethylpyrrolidino, 3-azabicyclo (3.2.2) nonyl, and ethyl N-piperazinocarboxylate.

### Claim 16 (depends on 15)

A composition according to claim 15 wherein m is one.

### Claim 17 (depends on 9)

A composition according to claim 9 wherein R is selected from the group consisting of 3-azabicyclo (3.2.2) nonyl and ethyl N-piperazinocarboxylate.