# US 4,394,383 A · N-Alkoxysulfenylcarbamates useful as insecticides

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- Number: US 4,394,383 A
- Document ID: US4394383A
- Status: Granted
- Kind: A
- Application number: 06/306,437
- Filed: 1981-09-28
- Granted: 1983-07-19
- Earliest claimed: 1981-09-28
- Assignees: The Regents of the University of California
- Inventors: Mitsuyasu Kawata; Noriharu Umetsu; Tetsuo R. Fukuto
- Web page: https://patentgrep.com/patent/US4394383A

## CPC

- A01N 47/24: containing the groups [IMAGE cpc-sch-A01N-0944.gif], [IMAGE cpc-sch-A01N-0945.gif] or[IMAGE cpc-sch-A01N-0946.gif]; Thio analogues thereof
- C07D 307/86: with an oxygen atom directly attached in position 7
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A novel class of chemical compounds useful as pesticides consists of N-alkoxysulfenylcarbamate esters. The preparation of these compounds, their physical properties, formulations, and use to control both household insects and crop pests are exemplified.

## Claims

### Claim 1

A composition having pesticidal activity comprising about 60 to 95 percent by weight of a carbamate of the formula: ##STR12## wherein R is a hydrocarbyl group containing from 1 to 12 carbon atoms; R.sub.1 is a hydrocarbyl group containing from 1 to 20 carbon atoms or is a benzoheterocyclic ring containing 5 or 6 members in the heterocyclic portion, said heterocyclic portion containing one or two O or S atoms; and R.sub.2 is a hydrocarbyl group containing only atoms of carbon and hydrogen and from 1 to 24 carbon atoms, or is a substituted hydrocarbyl group of 1-24 carbon atoms containing, in addition to atoms of carbon and hydrogen, at least one other atom; and from about 5 to about 40 percent by weight of a polysulfide derivative of said carbamate of the formula: ##STR13## wherein n is an integer between 2 and about 4 and the other variables are as above.

### Claim 2 (depends on 1)

A composition as defined in claim 1 wherein R.sub.2 is selected from the group consisting of methyl, ethyl, isopropyl, hexyl, cyclohexyl, benzyl, dodecyl, n-butyl, 1-ethylpropyl, tert-butyl, octyl, decyl, P-methoxybenzyl and octadecyl.

### Claim 3 (depends on 1)

A composition as defined in claim 1 which is selected from the group consisting of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(methoxysulfenyl)(methyl)carbamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(ethoxysulfenyl)-(methyl)carbamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(isopropoxysulfenyl)(methyl)carbama te; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(hexyloxysulfenyl)(methyl)carbamate ; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(cyclohexyloxysulfenyl)(methyl)car bamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(benzyloxysulfenyl)(methyl)carbamat e; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(dodecyloxysulfenyl)(methyl)carbama te; 2-isopropoxyphenyl(butoxysulfenyl)(methyl)carbamate; 2-isopropoxyphenyl(benzyloxysulfenyl)(methyl)carbamate; 3-isopropylphenyl(butoxysulfenyl)(methyl)carbamate; 3-isopropylphenyl(benzyloxysulfenyl)(methyl)carbamae; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(1-ethylpropoxysulfenyl)(methyl)car bamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(tert-butoxysulfenyl)(methyl)carbam ate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(methyl)(octyloxysulfenyl)carbamate ; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (decyloxysulfenyl)(methyl)carbamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(P-methoxybenzyloxysulfenyl)(methyl )carbamate; 2,3-dihydro-2,2-dimethyl-7-benzofuranyl(P-tert-butyl-benzyloxysulfenyl)(me thyl)carbamate; 2,3-dihydro 2,2-dimethyl-7-benzofuranyl(methyl)(octadecyloxysulfenyl)carbamate.

### Claim 4 (depends on 1)

An insecticidal composition comprising an insecticidally effective amount of a composition as defined in claim 1 in combination with a suitable carrier.

### Claim 5 (depends on 2)

An insecticidal composition comprising an insecticidally effective amount of a composition as defined in claim 2 in combination with a suitable carrier.

### Claim 6 (depends on 3)

An insecticidal composition comprising an insecticidally effective amount of a composition as defined in claim 3 in combination with a suitable carrier.

### Claim 7 (depends on 1)

The method of controlling insects which comprises applying to the sites of infestation an insecticidally effective amount of a composition as defined in claim 1.

### Claim 8 (depends on 2)

The method of controlling insects which comprises applying to the sites of infestation an insecticidally effective amount of a composition as defined in claim 2.

### Claim 9 (depends on 3)

The method of controlling insects which comprises applying to the sites of infestation an insecticidally effective amount of a composition as defined in claim 3.