Substituted 1,3,4-oxa- and thiadiazolinones of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be sutstituted,R.sup.3 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents O or S, andY represents O or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one, and 5-phenoxy-3-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one are disclosed as useful to combat endoparasites. Compositions containing these compounds and process for preparing them are also disclosed.The present invention relates to new substituted 1,3,4-oxa(thia)diazolinones, process for their preparation, and their use for combating endoparasites.Substituted 2-alkoxy-1,3,4-oxathiazolinones and their use against endoparasites are already known, but their actions are not always satisfactory (DE-OS (German Published Specification) 2,604,110). Previously described compounds are furthermore 2-aryloxy-1,3,4-oxadiazolinones (Pilgram, J. Heterocyclic Chem. 39, 823 (1982)); however, nothing is known about their use for combating endoparasites.The present invention relates to substituted 1,3,4-oxa-and thiadiazolinones of the formula (I) ##STR2## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogeno-alkylthio,R.sup.2 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkyl-sulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,R.sup.3 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkyl-sulphonyl, arylsulphonyl, sulphamoyl, alkyl-sulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents 0 or S, andY represents 0 or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one and 5-phenoxy-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one.The invention also relates to a process for the preparation of the new substituted 1,3,4-oxa- and thiadiazolinones of the formula ##STR3## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogeno-alkylthio,R.sup.2 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, aryl-sulphonyl, sulphamoyl, alkylsulphamoyl, dialkyl-sulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,R.sup.3 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkyl-sulphonyl, arylsulphonyl, sulphamoyl, alkyl-sulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents O or S, andY represents O or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one and 5-phenoxy-3-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one, characterized in that compounds of the formula (II) ##STR4## in which X, Y, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, are reacted with carbonylation reagents such as phosgene, phosgene or triphosgene, and the compounds obtained in this process, of the formula III ##STR5## in which X, Y, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, are cyclized in the presence of bases.
Description
Claims
1. A substituted 1,3,4-thiadiazolinone of the formula ##STR8## in which R.sup.1 represents halogen; or represents alkyl having 1 to 4 carbon atoms; alkoxy having 1 to 4 carbon atoms; alkylthio having 1 to 4 carbon atoms; halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different;
R.sup.2 represent hydrogen; or represents alkyl having 1 to 4 carbon atoms; alkoxy having 1 to 4 carbon atoms; alkylthio having 1 to 4 carbon atoms; halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; alkylenedioxy having 1 to 2 carbon toms; halogen-substituted alkylenedioxy having 1 to 2 carbon atoms and 1 to 4 halogen atoms, the halogen atoms being identical or different; halogen; cyano; nitro; dialkylamino having 1 to 4 carbon atoms per alkyl group; alkylcarbonyl having 2-4 carbon atoms; carbalkoxy having 2 to 4 carbon atoms; alkylsulphonyl having 1 to 4 carbon atoms; or represents phenyl, naphtha, phenoxy, naphthoxy, phenylthio or naphthylthio;
R.sup.3 represents alkyl having 1 to 4 carbon atoms; alkoxy having 1 to 4 carbon atoms; alkylthio having 1 to 4 carbon atoms; halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; halogenoalkythio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, the halogen atoms being identical or different; alkylenedioxy having 1 to 2 carbon atoms; halogen-substituted alkylenedioxy having 1 to 2 carbon atoms and 1 to 4 halogen atoms, the halogen atoms being identical or different; cyano; nitro; alkylcarbonyl having 2-4 carbon atoms; carbalkoxy having 2 to 4 carbon atoms; alkylsulphonyl having 1 to 4 carbon atoms; arylsulphonyl having 6 to 10 aryl carbon atoms; or represents phenyl, napthyl, phenoxy, naphthoxy, phenylthio or naphthylthio;
X represents S; and
Y represents O or S.
2. The substituted thiadiazolinone according to claim 1 in which
R.sup.1 represents halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -halogenoalkoxy, C.sub.1-4 -halogenoalkylthio, or nitro or cyano; carbalkoxy; or alkylsulphonyl,
R.sup.3 represents halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -halogenoalkoxy, C.sub.1-4 -halogenoalkylthio, or nitro or cyano; carbalkoxy; or alkylsulphonyl,
X represents S, and
Y represents O or S.
3. The substituted 1,3,4-thiadiazolinone of the formula ##STR9## in which
______________________________________R.sup.1 is R.sup.2 is R.sup.3 is X is Y is______________________________________--Cl --H --H S S--H 3,4-Cl.sub.24-Cl S S--CH.sub.33-CH.sub.3 --H S S--CH.sub.33-CH.sub.34-CH.sub.3 S S--Cl3-Cl --H S S--Cl 6-Cl --H S S--F --H --H S S--H 4-Br4-Cl S S--Cl3-Cl3-Cl S S--Cl3-CH.sub.3 --H S O--Cl --H --H S O--CH.sub.33-CH.sub.3 --H S O--Cl --H4-Cl S O--CH.sub.3 --3CH.sub.33-Cl S O--F 5-F 4-Cl S O--CH.sub.3 --CH.sub.3 4-CH.sub.3 S O--Cl --H4-CH.sub.3 S O--Cl4-CH.sub.34-CH.sub.3 S O______________________________________
4. A composition useful to combat endoparasites, which comprises a carrier and a substituted 1,3,4-thiadiazolinone according to claim 1 in an amount effective to combat endoparasites.
5. A method of combating endoparasites, which comprises administering to a patient a substituted according to claim 1 in an amount effective to combat endoparasites.
6. A method of combating endoparasites, which comprises administering to a patient a substituted 1,3,4-thiadiazolinone according to claim 3 in an amount effective to combat endoparasites.
Patent Grant
5093343
