# US 4,394,151 A · Azolyl-hydroxy alkanoic acid compounds

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- Number: US 4,394,151 A
- Document ID: US4394151A
- Status: Granted
- Kind: A
- Application number: 06/288,203
- Filed: 1981-07-29
- Granted: 1983-07-19
- Earliest claimed: 1980-08-22
- Assignees: Imperial Chemical Industries PLC
- Inventors: Paul de Fraine; John M. Clough; Paul A. Worthington
- Web page: https://patentgrep.com/patent/US4394151A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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

Compounds of formula ##STR1## useful as fungicides and plant growth regulators.

## Claims

### Claim 1

A racemic compound having the general formula (I): ##STR5## and stereoisomers thereof, wherein R.sup.1 is a straight or branched chain alkyl group having from 1 to 6 carbons, phenyl or phenyl substituted with halogen, alkyl, alkoxy, nitro, phenyl or phenoxy; R.sup.2 and R.sup.3 are together a --CH.sub.2 --CH.sub.2 -- bridging group, or each represents hydrogen, straight or branched chain alkyl groups having from 1 to 6 carbon atoms, phenyl or benzyl or phenyl or benzyl substituted with halogen, alkyl or alkoxy of 1 to 6 carbons, nitro, phenyl or phenoxy, the alkyl moiety of the benzyl being unsubstituted or substituted with alkyl of from 1 to 6 carbons; and Y is .dbd.N-- or .dbd.CH--, and acid addition salts, alkyl, aralkyl or aryl ethers, alkanoate esters and metal complexes thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 of general formula (I), and stereoisomers thereof, wherein R.sup.1 is an alkyl group containing from 1 to 4 carbon atoms or is halophenyl, R.sup.2 is hydrogen or methyl; R.sup.3 is an alkyl group containing from 1 to 4 carbon atoms; and Y is .dbd.N--.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R.sup.1 is phenyl, benzyl, .alpha.-methylbenzyl, 2-, 3- or 4-chloro-phenyl, 2,4- or 2,6-dichlorophenyl, 2-, 3- or 4-fluoro-phenyl, 2-, 3- or 4-bromophenyl, 2-, 3- or 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2-, 3- or 4-ethoxy-phenyl, 2-, 3- or 4-nitrophenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-trifluoromethylphenyl, and 4-phenyl-phenyl, or is a correspondingly ring-substituted benzyl or .alpha.-methylbenzyl group; and Y is .dbd.N-- or .dbd.CH--.

### Claim 4

The racemic compound having the structure: ##STR6## and its stereoisomers.

### Claim 5 (depends on 1)

A fungicidal composition comprising as an active ingredient a fungicidally effective amount of a compound as defined in claim 1; or the indicated salt, ether, ester or metal complex thereof; and a carrier or diluent for the active ingredient.

### Claim 6 (depends on 1)

A method of combating fungal diseases in a plant, which comprises applying to the plant, to seed of the plant, or to the locus of the plant or seed, a fungicidally effective amount of a compound as defined in claim 1.

### Claim 7 (depends on 1)

A method of regulating plant growth which comprises applying to the plant, to seed of the plant, or to the locus of the plant or seed, a plant growth regulating amount of a compound as defined in claim 1.