# US 4,397,869 A · Combating fungi with N-sulphenylated ureas

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- Number: US 4,397,869 A
- Document ID: US4397869A
- Status: Granted
- Kind: A
- Application number: 06/290,899
- Filed: 1981-08-07
- Granted: 1983-08-09
- Earliest claimed: 1980-08-27
- Assignees: Bayer Aktiengesellschaft
- Inventors: Engelbert Kuhle; Wilhelm Brandes; Paul-Ernst Frohberger
- Web page: https://patentgrep.com/patent/US4397869A

## CPC

- A01N 47/34: containing the groups [IMAGE cpc-sch-A01N-0947.gif], e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- C07C 313/34: either X or Y, but not both, being nitrogen atoms, e.g. N-sulfenylureas
- 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

N-Sulphenylated ureas of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkylmercapto, trihalogenomethyl-, trihalogenomethoxy or trihalogenomethylmercapto, R.sup.7 is hydrogen or alkyl, and n is 0, 1, 2 or 3, which possess fungicidal properties.

## Claims

### Claim 1

An N-sulphenylated urea of the formula ##STR31## in which R.sup.1 to R.sup.6 each independently is hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkylmercapto, trihalogenomethyltrihalogenomethoxy or trihalogenomethylmercapto,
R.sup.7 is hydrogen or alkyl, and
n is 0, 1 or 2,
at least one of the phenyl rings being unsubstituted.

### Claim 2 (depends on 1)

A compound according to claim 1, in which
R.sup.1 to R.sup.6 each independently is hydrogen, halogen, nitro, cyano, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, trihalogenomethyl, trihalogenomethoxy or trihalogenomethylmercapto.

### Claim 3 (depends on 1)

A compound according to claim 1, in which
R.sup.1 to R.sup.6 each independently is hydrogen, chlorine, trifluoromethyl or methoxy,
R.sup.7 is hydrogen or C.sub.1-4 -alkyl, and
n is 2.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-3,5-dichlorophenyl-N.sup.1 -phenylurea of the formula ##STR32##

### Claim 5 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-4-chlorophenyl-N.sup.1 -phenylurea of the formula ##STR33##

### Claim 6 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-phenyl-N.sup.1 -phenylurea of the formula ##STR34##

### Claim 7 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-3-chlorophenyl-N.sup.1 -phenylurea of the formula ##STR35##

### Claim 8 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-3-trifluoromethylphenyl-N.sup.1 -phenylurea of the formula ##STR36##

### Claim 9 (depends on 1)

A compound according to claim 1, wherein such compound is N-(fluorodichloromethylsulphenyl)-N-phenyl-N.sup.1 -4-chlorophenylurea of the formula ##STR37##

### Claim 10 (depends on 1)

A fungicidal composition comprising a fungicidally effective amount of a compound according to claim 1 in admixture with a diluent.

### Claim 11 (depends on 1)

A method of combating fungi comprising applying to the fungi, or to a habitat thereof, a fungicidally effective amount of a compound according to claim 1.

### Claim 12 (depends on 11)

The method according to claim 11, where such compound is
N-(fluorodichloromethylsulphenyl)-N-3,5-dichlorophenyl-N.sup.1 -phenylurea,
N-(fluorodichloromethylsulphenyl)-N-4-chlorophenyl-N.sup.1 -phenylurea,
N-(fluorodichloromethylsulphenyl)-N-phenyl-N.sup.1 -phenylurea,
N-(fluorodichloromethylsulphenyl)-N-3-chlorophenyl-N.sup.1 -phenylurea,
N-(fluorodichloromethylsulphenyl)-N-3-trifluoromethyl-phenyl-N.sup.1 -phenylurea or
N-(fluorodichloromethylsulphenyl)-N-phenyl-N.sup.1 -4-chlorophenylurea.