# US 4,394,386 A · Fluorinated carbamate insecticides

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- Number: US 4,394,386 A
- Document ID: US4394386A
- Status: Granted
- Kind: A
- Application number: 06/338,474
- Filed: 1982-01-11
- Granted: 1983-07-19
- Earliest claimed: 1979-09-10
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: William J. Middleton
- Web page: https://patentgrep.com/patent/US4394386A

## CPC

- C07D 273/00: Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- 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
- C07C 259/02: with replacement of the other oxygen atom of the carboxyl group by halogen atoms
- C07C 327/58: Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
- C07D 307/86: with an oxygen atom directly attached in position 7
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Fluorinated carbamoyl sulfides, such as N,N'[thiobis[(methylimino)carbonyloxy]]bis[2,2,2-trifluoroethanimidothioic acid], dimethyl ester, useful for control of insects.

## Claims

### Claim 1

A compound of the formula: ##STR125## R.sup.3 is CFXY, CON(CH.sub.3).sub.2, CH.sub.2 OCH.sub.3, or C.sub.1 -C.sub.3 alkyl; wherein X and Y are independently H or F;
R.sup.4 is H or CH.sub.3 ;
P.sub.5 is 0, 1 or 2;
R.sup.5 or R.sup.6 are independently H, C.sub.1 -C.sub.4 alkyl, phenyl or phenyl substituted with one atom of F, Cl, Br or CH.sub.3 ;
provided that when:
R.sup.4 is CH.sub.3, R' must be ##STR126## and R.sup.3 must be CFXY.

### Claim 2 (depends on 1)

A compound of claim 1 wherein
R is ##STR127## R.sup.2 is C.sub.1 -C.sub.3 alkyl; R.sup.3 is CFXH, CON(CH.sub.3).sub.2, CH.sub.2 OCH.sub.3 or C.sub.1 -C.sub.3 alkyl.

### Claim 3 (depends on 1)

An insecticide composition consisting essentially of a surfactant, diluent, and an effective amount of a compound of claim 1.

### Claim 4 (depends on 2)

An insecticide composition consisting essentially of a surfactant, diluent, and an effective amount of a compound of claim 2.

### Claim 5 (depends on 1)

A method for controlling insects which comprises applying to a locus to be protected an insecticidally effective amount of a compound of claim 1.

### Claim 6 (depends on 2)

A method for controlling insects which comprises applying to a locus to be protected an insecticidally effective amount of a compound of claim 2.