Substituted 1,3,4-thiadizaolinones, processes for their preparation, and
their use for combating endoparasites
    1.
    发明授权
    Substituted 1,3,4-thiadizaolinones, processes for their preparation, and their use for combating endoparasites 失效
    取代1,3,4-噻唑烷酮,其制备方法及其用于组合内生菌的用途

    公开(公告)号:US5095024A

    公开(公告)日:1992-03-10

    申请号:US581934

    申请日:1990-09-13

    摘要: Substituted 1,3,4-thiadiazolinones of the formula (I), ##STR1## in which X represents O or S,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 the series comprising 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 and arylthio, each of which can, in turn, be substituted as well, andR.sup.3 represents alkyl, alkenyl or alkynyl, each of which can optionally be substituted,with the exception of the compound 5-methylmercapto-3-phenyl-1,3,4-thiadiazol-2-(3H)-one, are disclosed as being useful to combat endoparasites. Compositions containing these compounds, process for preparing them, and novel intermediates are also disclosed.

    摘要翻译: 取代的式(I)的1,3,4-噻二唑啉酮,其中X代表O或S,R1代表氢,烷基,烷氧基,烷硫基,卤素,卤代烷基,卤代烷氧基或卤代烷硫基,R2代表一 或更多相同或不同的基团,其包含氢,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代烷硫基,亚烷基二氧基,卤代亚烷基二氧基,卤素,CN,NO 2,NH 2,烷基氨基,二烷基氨基,烷基羰基,烷氧基,烷基磺酰基,芳基磺酰基,氨磺酰基, 烷基氨磺酰基,二烷基氨磺酰基,芳基,芳氧基和芳硫基,其中每一个也可以被取代,并且R 3表示烷基,烯基或炔基,其中每一个可任选被取代,除了化合物5-甲基巯基 - 3-苯基-1,3,4-噻二唑-2-(3H) - 酮被公开用于对抗内寄生虫。 还公开了含有这些化合物的组合物,其制备方法和新型中间体。

    Substituted 1,3,4-oxa (thia) diazolinones process for their preparation
and their use of combating endoparasites

    公开(公告)号:US5093343A

    公开(公告)日:1992-03-03

    申请号:US577970

    申请日:1990-09-05

    摘要: 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.

    Preparation of novel 5-acyloxy-4-(5H)-oxazolonium salts suited for use
as intermediates for triazinone herbicides
    10.
    发明授权
    Preparation of novel 5-acyloxy-4-(5H)-oxazolonium salts suited for use as intermediates for triazinone herbicides 失效
    制备适合用作三嗪酮除草剂的中间体的新型5-酰氧基-4-(5H) - 恶唑鎓盐

    公开(公告)号:US4594427A

    公开(公告)日:1986-06-10

    申请号:US360495

    申请日:1982-03-22

    CPC分类号: C07D253/075 C07D263/44

    摘要: Novel 5-acyloxy-4(5H)-oxazolonium salts of the formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic group with up to 12 carbon atoms, an optionally substituted cycloalkyl group with 3 to 10 carbon atoms, an optionally substituted phenyl or naphthyl group or an optionally substituted heterocyclic group andR.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom or an optionally substituted aliphatic group with up to 8 carbon atoms or an optionally substituted phenyl group andX.sup..crclbar. represents the anion of an inorganic or organic acid having a pK.sub.a value of less than 2,are obtained in solution when an acyl cyanide of the general formulaR.sup.1 --CO--CN (II)is reacted with a carboxylic acid anhydride of the general formulaR.sup.2 --CO--O--CO--R.sup.3 (III)whereinR.sup.1, R.sup.2 and R.sup.3 each have the abovementioned meaning,in the presence of one or more inorganic or organic acids having a pK.sub.a value of less than 2, and if appropriate in the presence of a solvent, and if appropriate at a temperature between 0.degree. and 120.degree. C.The novel oxazolonium salts (I) can be used as intermediate products for the preparation of known, herbicidally active 3,4,6-trisubstituted 1,2,4-triazin-5(4H)-ones.

    摘要翻译: 式(Ⅰ)的新的5-酰氧基-4(5H) - 恶唑盐,其中R 1表示任选取代的具有至多12个碳原子的脂族基团,任选取代的具有3至10个碳原子的环烷基, 任选取代的苯基或萘基或任选取代的杂环基,R2和R3相同或不同,表示氢原子或任选取代的具有至多8个碳原子的脂族基团或任选取代的苯基,X( - )表示 当通式R 1 -CO-CN(II)的酰基氰与通式为R 2 -CO的羧酸酐反应时,溶液中得到pKa值小于2的无机或有机酸的阴离子 在一种或多种pKa值小于2的无机或有机酸的存在下,并且如果在溶剂存在下适当,其中R 1,R 2和R 3各自具有上述含义的-O-CO-R 3(III) ,如果合适的话 在0至120℃之间的温度下,新的恶唑鎓盐(I)可用作中间产物,用于制备已知的除草活性的3,4,6-三取代的1,2,4-三嗪-5(4H )-那些。