# US 5,344,839 A · Sulfonamides as antifungal agents

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- Number: US 5,344,839 A
- Document ID: US5344839A
- Status: Granted
- Kind: A
- Application number: 08/002,898
- Filed: 1993-01-11
- Granted: 1994-09-06
- Earliest claimed: 1990-10-08
- Assignees: J. Uriach & Cia. S.A.
- Inventors: Javier Bartroli; Manuel Anguita; Jordi Belloc; Elena Carceller; Carmen Almansa
- Web page: https://patentgrep.com/patent/US5344839A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- 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

The present invention relates to new sulfonamides having the formula I: ##STR1## wherein: R.sup.1 represents an alkyl, aryl or heteroaryl group; R.sup.2 is hydrogen or an alkyl, aryl or heteroaryl group; or R.sup.1 and R.sup.2 may form a ring; R.sup.3 is hydrogen or may form an oxazolidine ring together with R.sup.2, and this ring may be optionally susbtituted by one or two alkyl, aryl or heteroaryl groups at the position 2; R.sup.7 is hydrogen or alkyl; X is CH or N; Ar is a phenyl ring or a substituted phenyl ring. The invention also relates to a procedure for their preparation and to pharmaceutical and agrochemical compositions containing them. These compounds are antifungal agents.

## Claims

### Claim 1

A compound of formula Ia: ##STR14## in which: X is N or CH;
R.sup.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl-C.sub.1 -C.sub.4 -alkyl, a phenyl-C.sub.1 -C.sub.4 -alkyl group where the phenyl ring carries a substituent selected from the group consisting of (a) as specified below, phenyl, naphthyl, a phenyl ring substituted with one or more members of group (a), quinolyl, or isoquinolyl,;
R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or (1H-1,2,4-triazol-1-yl)methyl;
R.sup.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or a phenyl group substituted with a member of group (a)
R.sup.7 is hydrogen or C.sub.1 -C.sub.6 alkyl;
Ar is phenyl or a phenyl ring substituted with one or more halogen or trifluoromethyl groups;
wherein group (a) consists of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, halogen, CF.sub.3, NO.sub.2, CN, OH, OCH.sub.2 Ph, CH.sub.2 OH, NHAc, a group of formula --CH.sub.2 --OCO--R.sup.6, a group of formula --CO--R.sup.6, a group of formula --COO-- R.sup.6, a group of formula --SO.sub.z R.sup.6, NH.sub.2, NHR.sup.6, or NR.sup.6.sub.2 ;
R.sup.6 is C.sub.1 -C.sub.4 alkyl;
Z is 0, 1 or 2;
or an acid-addition salt thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 of formula Ia, in which:
X is N;
Ar is a phenyl ring substituted with one or two chlorine, fluorine or trifluoromethyl groups, or a combination thereof;
R.sup.4 and R.sup.5 are both hydrogen, or R.sup.4 is hydrogen and R.sup.5 is C.sub.1 -C.sub.6 alkyl or phenyl.

### Claim 3 (depends on 1, 2)

A compound according to claim 1 or 2 wherein R.sup.1 is methyl, ethyl, or propyl.

### Claim 4

5-(2,4-D ichlorophenyl)-3-methanesulfonyl-5-([1H-1,2,4-triazol-1-yl]methyl)oxazolidi ne.

### Claim 5

(4R*,5R*)-5-(2,4-Dichlorophenyl)-3-methanesulfonyl-4-methyl-5-([1H-1,2,4-tr iazol-1-yl]methyl)oxazolidine.

### Claim 6

(4R*,5R*)-5-(2,4-Difluoroph enyl)-3-methanesulfonyl-4-methyl-5-([1H-1,2,4-triazol-1-yl]methyl)oxazolidi ne.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent in admixture with an antifungal effective amount of a compound of claim 1.

### Claim 8 (depends on 1)

An agrochemical composition comprising an agronomically acceptable carrier or diluent in admixture with an antigungal effective amount of a compound of claim 1.

### Claim 9 (depends on 1)

A method for treating fungal infections in an animal, which comprises administering to an animal in need thereof an antifungal-effective amount of a compound of claim 1.

### Claim 10 (depends on 9)

A method according to claim 9 wherein the administration step comprises oral or parental administration and the antifungal-effective amount is from 0.010 to 20 mg/kg of body weight.

### Claim 11 (depends on 1)

A method of con, batting fungal diseases in a plant, which comprises applying to the plant, to the seed of the plant or to the locus of the plant or an antifungal effective amount of seed a compound of claim 1.