# US 4,399,285 A · Tetrazolyloxyacetic acid amides, piperidides and perhydro azepinides

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- Number: US 4,399,285 A
- Document ID: US4399285A
- Status: Granted
- Kind: A
- Application number: 06/200,171
- Filed: 1980-10-24
- Granted: 1983-08-16
- Earliest claimed: 1979-11-17
- Assignees: Bayer Aktiengesellschaft
- Inventors: Heinz Forster; Wolfgang Hofer; Fritz Maurer; Volker Mues; Ludwig Eue; Robert R. Schmidt
- Web page: https://patentgrep.com/patent/US4399285A

## CPC

- C07D 257/04: Five-membered rings
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- C07D 209/04: Indoles; Hydrogenated indoles
- C07D 215/08: with acylated ring nitrogen atom
- C07D 295/185: from aliphatic carboxylic acids
- C07D 453/06: containing isoquinuclidine ring 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

Tetrazolyloxycarboxylic acid amide compound of the formula ##STR1## wherein R is an optionally substituted radical selected from the group consisting of alkyl or aryl, R.sup.1 is hydrogen or alkyl, n is 0 or 1, and R.sup.2 and R.sup.3 are individually selected from hydrogen or optionally substituted radicals selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl and aryl, with the proviso that when n is 0, R.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, form an optionally substituted, optionally partially unsaturated and optionally benzo-fused monocyclic or bicyclic radical which optionally contains one or more further hetero-atoms are effective herbicides.

## Claims

### Claim 1

A tetrazolyloxycarboxylic acid amide of the formula ##STR148## wherein R is phenyl, mono chlorophenyl or dichlorophenyl,
R.sup.1 is hydrogen,
R.sup.2 is C.sub.1 -C.sub.6 -alkyl, allyl, propargyl, 1-methyl-propargyl, 1,1-dimethyl-propargyl, cyclohexyl, benzyl or phenyl, and
R.sup.3 is C.sub.1 -C.sub.6 -alkyl or allyl or
R.sup.2 and R.sup.3 together with the nitrogen atom to which they are bonded, represent piperidyl, monoalkyl or dialkyl substituted piperidyl with 1 to 3 carbon atoms per alkyl group or perhydroazepinyl.

### Claim 2 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 wherein R is phenyl.

### Claim 3 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 wherein R.sup.2 is methyl.

### Claim 4 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 wherein R.sup.3 is methyl and R.sup.2 is C.sub.1 -C.sub.6 alkyl, allyl, propargyl, 1-methyl-propargyl cyclohexyl, benzyl or phenyl.

### Claim 5 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 designated 1-phenyl-5-tetrazolyloxyacetic acid diallylamide.

### Claim 6 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 designated 1-phenyl-5-tetrazolyloxyacetic acid hexamethylene-amide.

### Claim 7 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 designated 1-phenyl-5-tetrazolyloxyacetic acid 3-methyl-piperidide.

### Claim 8 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 designated 1-phenyl-5-tetrazolyloxyacetic acid 2-ethyl-piperidide.

### Claim 9 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 designated 1-phenyl-5-tetrazolyloxyacetic acid N-methyl-anilide.

### Claim 10 (depends on 1)

Tetrazolyloxycarboxylic acid amide compound as claimed in claim 1 wherein R.sup.3 is methyl.