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New insecticides by replacement of carbon by other Group IV elements

机译:用其他第四类元素代替碳的新型杀虫剂

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AbstractAll of the Group IV elements, C, Si, Ge, Sn and Pb, form four tetrahedrally disposed bonds and could be considered as replacements for each other. Because the atomic radius increases linearly with increasing row number, this replacement can also be considered as a probe of steric effects. The use of silicon, with its high natural abundance and non‐toxic nature, has received the most attention. Examples of silicon‐for‐carbon exchange can be found for all major classes of insecticides, including carbamates, phosphates, pyrethroids, as well as DDT and juvenile hormone analogs. Generally, the silicon analogs retain insecticidal activity. A silicon analog of MTI‐800 (dimethyl‐4‐ethoxyphenyl‐I‐(3‐(4‐fluoro‐3‐phenoxyphenyl)propyl)silane) is a broad spectrum insecticide. This silane was used as a starting point for building new silane analogs as potential insecticides. Two analogs were particularly noteworthy. A silane with a cyclopropyl group was found to be non‐toxic to Trichoplusia ni (cabbage looper) while the corresponding carbon compound was a potent insecticide. An analog containing a silicon‐hydrogen bond, a structural feature reported to be unstable in vivo, was found to be significantly insecticidal both topically and in foliar tests. The latter compound suggests that biologically active silanes can encompass broader structural types
机译:摘要 C、Si、Ge、Sn和Pb四族元素均形成4个四面体键,可相互替代。由于原子半径随着行数的增加而线性增加,因此这种替换也可以被视为空间效应的探针。硅的使用因其高天然丰度和无毒性质而受到最多的关注。所有主要类别的杀虫剂都可以找到硅碳交换的例子,包括氨基甲酸酯、磷酸盐、拟除虫菊酯以及滴滴涕和幼年激素类似物。通常,硅类似物保留杀虫活性。MTI-800(二甲基-4-乙氧基苯基-I-(3-(4-氟-3-苯氧基苯基)丙基)硅烷的硅类似物是一种广谱杀虫剂。这种硅烷被用作构建新的硅烷类似物作为潜在杀虫剂的起点。两个类似物特别值得注意。发现具有环丙基的硅烷对卷心菜蠖无毒,而相应的碳化合物是一种强效杀虫剂。一种含有硅氢键的类似物,据报道在体内不稳定的结构特征,在局部和叶面试验中都具有显着的杀虫作用。后一种化合物表明,具有生物活性的硅烷可以包含更广泛的结构类型

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