申请人:Ciba-Geigy Corporation
公开号:US05138068A1
公开(公告)日:1992-08-11
Novel 1-phenyl-5-oxo-2-tetrazolines of formula I ##STR1## in which R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.1 -C.sub.4 alkyl- or halo-substituted C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or halo-substituted C.sub.5 -C.sub.6 cycloalkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.6 alkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.8 alkynyl, or C.sub.1 -C.sub.8 alkyl that is substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, cyano, hydroxy, halophenyl, C.sub.1 -C.sub.4 alkylphenyl or by a heteroaromatic radical, R.sup.2 is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, cyclopentenyl or cyclohexenyl, or is C.sub.1 -C.sub.6 alkyl that is substituted by halogen, by C.sub.1 -C.sub.4 alkoxy or by C.sub.1 -C.sub.4 alkylthio, each of R.sup.3 and R.sup.4, independently of the other, is hydrogen, halogen, 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 alkylthio, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.4 cyanoalkyl, phenyl-C.sub.2 -C.sub.4 alkenyl or phenyl-C.sub.2 -C.sub.4 alkynyl, or R.sup.3 and R.sup.4 together are a --CH.dbd.CH--CH.dbd.CH--, --CH.sub.2 --CH.dbd.CH--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 --, --O--CH.sub.2 --O--, --O--CH.sub.2 --CH.sub. 2 --O--, --CH.sub.2 --O--CH.sub.2 --, --(CH.sub.2).sub.2 --CH.dbd.CH-- or --CH.sub.2 --CH.dbd.CH--CH.sub.2 -- bridge, each of which may be substituted by one or two C.sub.1 -C.sub.4 alkyl groups, and R.sup.5 is hydrogen or a --Z--R.sup.6 group in which R.sup.6 is phenyl, naphthyl or pyridyl, or is phenyl, naphthyl or pyridyl each of which is substituted by one or two substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, di-C.sub.1 -C.sub.4 alkylamino, nitro, cyano, C.sub.1 -C.sub.4 alkoxycarbonyl and C.sub.1 -C.sub.4 alkylcarbonyl, and Z is oxygen, sulfur, a direct bond, --NH--, --N(C.sub.1 -C.sub.2 alkyl)--, --N(CHO)--, --CH.sub.2 --, --CH(CH.sub.3)-- or --C(CH.sub.3).sub.2 -- can be used as pesticides. Preferably, insects and arachnids can be controlled.
化合物I的一种新型1-苯基-5-氧代-2-四唑啉,其化学式为##STR1##其中R.sup.1为C.sub.1-C.sub.8烷基,C.sub.3-C.sub.6烯基,C.sub.3-C.sub.6炔基,C.sub.3-C.sub.6环烷基,C.sub.5-C.sub.6环烯基,C.sub.1-C.sub.4烷基或卤代C.sub.3-C.sub.6环烷基,C.sub.1-C.sub.4烷基或卤代C.sub.5-C.sub.6环烯基,卤代,C.sub.1-C.sub.4烷氧基或苯基取代的C.sub.3-C.sub.6烯基,卤代,C.sub.1-C.sub.4烷氧基或苯基取代的C.sub.3-C.sub.8炔基,或由卤素,C.sub.1-C.sub.4烷氧基,C.sub.1-C.sub.4硫基烷基,C.sub.1-C.sub.4烷氧羰基,C.sub.3-C.sub.6环烷基,苯基,氰基,卤苯基,C.sub.1-C.sub.4烷基苯基或杂环芳基取代的C.sub.1-C.sub.8烷基取代;R.sup.2为C.sub.1-C.sub.6烷基,C.sub.2-C.sub.6烯基,C.sub.2-C.sub.6炔基,C.sub.3-C.sub.6环烷基,环戊烯基或环己烯基,或为卤代的C.sub.1-C.sub.6烷基,C.sub.1-C.sub.4烷氧基或C.sub.1-C.sub.4硫基烷基取代的C.sub.1-C.sub.6烷基,R.sup.3和R.sup.4各自独立地为氢,卤素,C.sub.1-C.sub.4烷基,C.sub.1-C.sub.4卤代烷基,C.sub.1-C.sub.4烷氧基,C.sub.1-C.sub.4硫基烷基,C.sub.3-C.sub.6环烷基,C.sub.2-C.sub.4烯基,C.sub.2-C.sub.4炔基,C.sub.2-C.sub.6烷氧烷基,C.sub.2-C.sub.6硫基烷基,C.sub.1-C.sub.4氰基烷基,苯基-C.sub.2-C.sub.4烯基或苯基-C.sub.2-C.sub.4炔基,或R.sup.3和R.sup.4一起是一个--CH.dbd.CH--CH.dbd.CH--,--CH.sub.2--CH.dbd.CH--,--(CH.sub.2).sub.4--,--(CH.sub.2).sub.3--,--O--CH.sub.2--O--,--O--CH.sub.2--CH.sub.2--O--,--CH.sub.2--O--CH.sub.2--,--(CH.sub.2).sub.2--CH.dbd.CH--或--CH.sub.2--CH.dbd.CH--CH.sub.2--桥,每个桥都可以由一个或两个C.sub.1-C.sub.4烷基取代;R.sup.5为氢或--Z--R.sup.6基团,其中R.sup.6为苯基,萘基或吡啶基,或为取代一个或两个取代基的苯基,萘基或吡啶基,所述取代基为卤素,C.sub.1-C.sub.4烷基,C.sub.1-C.sub.4烷氧基,C.sub.1-C.sub.4卤代烷氧基,C.sub.1-C.sub.4卤代烷基,C.sub.1-C.sub.4硫基烷基,C.sub.1-C.sub.4卤代硫基烷基,二C.sub.1-C.sub.4烷基氨基,硝基,氰基,C.sub.1-C.sub.4烷氧羰基和C.sub.1-C.sub.4烷基羰基,Z为氧,硫,一条直接键,--NH--,--N(C.sub.1-C.sub.2烷基)--,--N(CHO)--,--CH.sub.2--,--CH(CH.sub.3)--或--C(CH.sub.3).sub.2--,可以用作杀虫剂。最好用于控制昆虫和蜘蛛。