# US 4,394,388 A · Method for the control of cattle grubs employing m-phenoxybenzyl and .alpha .

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

- Number: US 4,394,388 A
- Document ID: US4394388A
- Status: Granted
- Kind: A
- Application number: 06/295,055
- Filed: 1981-08-21
- Granted: 1983-07-19
- Earliest claimed: 1981-08-21
- Assignees: American Cyanamid Company
- Inventors: Robert H. Schenkel
- Web page: https://patentgrep.com/patent/US4394388A

## CPC

- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- A01N 37/10: Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
- A01N 37/38: having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N 37/48: Nitro-carboxylic acids; Derivatives thereof
- A01N 41/10: Sulfones; Sulfoxides
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- C07C 51/487: by treatment giving rise to chemical modification (by chemisorption C07C51/47)
- C07C 59/64: containing six-membered aromatic rings
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

A method for the control of larvae of heel flies which parasitize ruminants and other domestic and farm animals involving topical application of a larvicidally effective amount of a m-phenoxybenzyl or .alpha.-cyano-m-phenoxybenzyl ester of a 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenyl alkanoic acid.

## Claims

### Claim 1

A method for protecting ruminant, domestic, and farm animals from infestation by the larvae of flies of the family Hypodermatidae comprising, applying topically to larvae-infested animals a larvicidally effective amount of a compound having the structural formula: ##STR3## wherein RCF.sub.2 X--, Y and Z are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO.sub.2 ; Y and Z is each H, Cl, F, Br, NO.sub.2, CH.sub.3 or OCH.sub.3 ; R is H, F, CHF.sub.2 or CF.sub.3 ; R.sub.2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R.sub.3 is H, CN or --C.tbd.CH; and R.sub.4 is H, F, Cl, CH.sub.3 or OCH.sub.3 or the optical isomers thereof.

### Claim 2 (depends on 1)

A method according to claim 1 wherein the compound has the formula: ##STR4## wherein RCF.sub.2 X-- is meta or para to the carbon to which the alkanoic acid ester group is attached; R is H or F; X is O or S; R.sub.2 is ethyl, n-propyl or isopropyl; R.sub.3 is H or CN; and R.sub.4 is H, F, Cl, CH.sub.3 or OCH.sub.3 and the optical isomers thereof, and the compound is applied to said animals' skin in an amount of from 0.05 to 150 mg/kg of animal body weight.

### Claim 3 (depends on 2)

A method according to claim 2 wherein the compound is .alpha.-cyano-m-phenoxybenzyl .alpha.-isopropyl-4-difluoromethoxyphenylacetate.

### Claim 4 (depends on 2)

A method according to claim 2 wherein the compound is (.+-.) .alpha.-cyano-m-phenoxybenzyl (+) .alpha.-isopropyl-4-difluoromethoxyphenylacetate.

### Claim 5

A method for protecting ruminant animals from infestation by the larvae of flies of the family Hypodermatidae comprising applying topically to the larvae-infested animals' skin a liquid solution containing from 0.005 to 1.0% by weight of a compound having the structural formula: ##STR5## wherein RCF.sub.2 X--, Y and Z are all metal or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO.sub.2 ; Y and Z is each H, Cl, F, Br, NO.sub.2, CH.sub.3 or OCH.sub.3 ; R is H, F, CHF.sub.2 or CF.sub.3 ; R.sub.2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R.sub.3 is H, CN or --C.tbd.CH; and R.sub.4 is H, F, Cl, CH.sub.3 or OCH.sub.3 or the optical isomers thereof.

### Claim 6 (depends on 5)

A method according to claim 5 wherein the compound has the structural formula: ##STR6## wherein RCF.sub.2 X-- is meta or para to the carbon to which the alkanoic acid ester group is attached; R is H or F; X is O or S; R.sub.2 is ethyl, n-propyl or isopropyl; R.sub.3 is H or CN; and R.sub.4 is H, F, Cl, CH.sub.3 or OCH.sub.3 or the optical isomers thereof.

### Claim 7 (depends on 6)

A method according to claim 6 wherein said animals are cattle and said compound is .alpha.-cyano-m-phenoxybenzyl .alpha.-isopropyl-4-difluoromethoxyphenylacetate.

### Claim 8 (depends on 6)

A method according to claim 6 wherein said animals are cattle and said compound is (+)-.alpha.-cyano-m-phenoxybenzyl (+)-.alpha.-isopropyl-4-difluoromethoxyphenylacetate.