# US 5,347,010 A · Tetrzolinone herbicides

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- Number: US 5,347,010 A
- Document ID: US5347010A
- Status: Granted
- Kind: A
- Application number: 08/086,606
- Filed: 1993-07-01
- Granted: 1994-09-13
- Earliest claimed: 1992-07-09
- Assignees: Nihon Bayer Agrochem K.K.
- Inventors: Toshio Goto; Hidenori Hayakawa; Yukiyoshi Watanabe; Shin-ichi Narabu; Akihiko Yanagi
- Web page: https://patentgrep.com/patent/US5347010A

## CPC

- C07D 257/04: Five-membered rings
- A01N 47/38: containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- 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

Novel tetrazolinones of the formula (I) ##STR1## wherein X is chlorine or bromine, Y is hydrogen, chlorine, bromine, methyl or ethyl, and R.sup.1 and R.sup.2 are the same or different C.sub.2-4 alkyl, a process for their preparation, and the use of the new compounds as herbicides, especially against paddy-weeds.

## Claims

### Claim 1

A tetrazolinone of the formula ##STR10## wherein X is chlorine or bromine,
Y is hydrogen, chlorine, bromine, methyl or ethyl, and
R.sup.1 and R.sup.2 each independently is C.sub.2-4 alkyl.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein
X is chlorine,
Y is hydrogen, chlorine or methyl, and
R.sup.1 and R.sup.2 each independently is ethyl, n-propyl, isopropyl, n-butyl, isobutyl or sec-butyl.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein such compound is 1-(2-chlorophenyl)-4-(N,N-diethylcarbamoyl)-5(4H)-tetrazolinone of the formula ##STR11##

### Claim 4 (depends on 1)

A compound according to claim 1, wherein such compound is 1-(2,6-dichlorophenyl)-4-(N,N-di-n-propylcarbamoyl)-5(4H)-tetrazolinone of the formula ##STR12##

### Claim 5 (depends on 1)

A compound according to claim 1, wherein such compound is 1-(2-chloro-6-methylphenyl)-4-(N,N-di-n-propylcarbamoyl)-5(4H)-tetrazolino ne of the formula ##STR13##

### Claim 6 (depends on 1)

A compound according to claim 1, wherein such compound is 1-(2-chloro-6-methylphenyl)-4-(N-sec-butyl-N-n-propylcarbamoyl)-5(4H)-tetr azolinone of the formula ##STR14##

### Claim 7 (depends on 1)

A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent.

### Claim 8 (depends on 1)

A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim 1.

### Claim 9 (depends on 8)

The method according to claim 8, wherein such compound is
1-(2-chlorophenyl)-4-(N,N-diethylcarbamoyl)-5(4H)-tetrazolinone;
1-(2,6-dichlorophenyl)-4-(N,N-di-n-propylcarbamoyl)-5(4H)-tetrazolinone;
1-(2-chloro-6-methylphenyl)-4-(N,N-di-n-propylcarbamoyl)-5(4H)-tetrazolinon e; (or)
1-(2-chloro-6-methylphenyl)-4-(N-sec-butyl-N-n-propylcarbamoyl)-5(4H)-tetra zolinone.