# US 4,400,516 A · Heterocyclic substituted triazole-3-ol compounds

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

- Number: US 4,400,516 A
- Document ID: US4400516A
- Status: Granted
- Kind: A
- Application number: 06/260,527
- Filed: 1981-05-04
- Granted: 1983-08-23
- Earliest claimed: 1978-10-13
- Assignees: The Dow Chemical Company
- Inventors: Chester E. Pawloski
- Web page: https://patentgrep.com/patent/US4400516A

## CPC

- C07D 213/77: Hydrazine radicals
- A01N 57/08: containing heterocyclic radicals
- C07F 9/6518: Five-membered rings
- C07F 9/65583: {each of the hetero rings containing nitrogen as ring hetero atom}
- 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
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Compounds are prepared which correspond to the formula ##STR1## wherein R represents a nitrogen containing heterocyclic radical corresponding to one of the formulae ##STR2## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR3## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.1 represents hydrogen, chloro, fluoro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3-6 carbon atoms, phenyl, phenylthio, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, thiocyanato, trifluoromethyl, trichloromethyl, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms; R.sup.2 represents methyl, ethyl, propyl or isobutyl and R.sup.3 represents methoxy, ethoxy, propoxy, ethyl, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms or phenyl.

## Claims

### Claim 1

A compound corresponding to the formula ##STR311## wherein R represents a nitrogen containing heterocyclic radical corresponding to the formulae ##STR312## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR313## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.1 represents hydrogen, chloro, fluoro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, phenylthio, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, thiocyanato, trifluoromethyl, trichloromethyl, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms.

### Claim 2 (depends on 1)

A compound as defined in claim 1 wherein the heterocyclic radical is ##STR314##

### Claim 3 (depends on 2)

The compound as defined in claim 2 which is 1-(6-chloro-2-pyridinyl)-1H-1,2,4-triazol-3-ol.

### Claim 4 (depends on 2)

The compound as defined in claim 2 which is 1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-ol.

### Claim 5 (depends on 2)

The compound as defined in claim 2 which is 1-(2-pyridinyl)-1H-1,2,4-triazol-3-ol.

### Claim 6 (depends on 2)

The compound as defined in claim 2 which is 1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-ol.

### Claim 7 (depends on 2)

The compound as defined in claim 2 which is 1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-ol.

### Claim 8 (depends on 2)

The compound as defined in claim 2 which is 1-(2-pyridinyl)-5-ethyl-1H-1,2,4-triazol-3-ol.

### Claim 9 (depends on 2)

The compound as defined in claim 2 which is 1-(6-phenoxy-2-pyridinyl)-1H-1,2,4-triazol-3-ol.

### Claim 10 (depends on 2)

The compound as defined in claim 2 which is 1-(6-phenoxy-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-ol.

### Claim 11 (depends on 2)

The compound as defined in claim 2 which is 1-(2-pyridinyl)-5-(1-methylethyl)-1H-1,2,4-triazol-3-ol.