Synthesis and Fungicidal Activity of Aryl Carbamic Acid-5-aryl-2-furanmethyl Ester
Synthesis and Fungicidal Activity of Aryl Carbamic Acid-5-aryl-2-furanmethyl Ester
复制标题
DOI：
10.1021/jf9043277
复制
发表时间：
2010-03-10
影响因子：
6.1
通讯作者：
Yang, Xin-Ling
中科院分区：
文献类型：
--
作者：
Li, Ying;Li, Bao-Ju;Yang, Xin-Ling
甲壳素是昆虫表皮和真菌细胞壁的主要结构成分，但在植物和脊椎动物中不存在，被认为是安全的和选择性的害虫防治剂的靶标。甲壳素合成抑制剂（Chitin synthesis inhibitors，CSIs）作为昆虫生长调节剂（insect growth regulators，IGRs）已被广泛应用，但作为杀菌剂在农业上应用较少。以26个新的芳基氨基甲酸-5-芳基-2-通过将苯甲酰基苯基脲的脲键转化为氨基甲酸酯并将苯胺部分变为呋喃甲基来设计呋喃甲基酯。合成了标题化合物，其结构经IR，1H-1 NMR和元素分析确证.进行了初步的杀虫和杀真菌生物测定。结果表明，目标化合物对淡色库蚊（Culex pipiens pallens）和小菜蛾（Plutella xylostella Linnaeus）无明显杀虫活性，但对黄瓜褐斑病菌（Corynespora cucumeris）、黄瓜枯萎病菌（Thanatephorus cucumeris）、番茄灰霉病菌（Botrytis cinerea）和尖孢镰刀菌（Fusarium oxysporum）均有较好的杀菌活性。特别地，化合物V-4、V-6、V-7和V-8显示出比商业化的杀真菌剂更好的对四种菌株的活性。形态学结果表明，化合物V-21干扰了C.阿奎科拉结果表明，对苯甲酰苯基脲脲的脲键进行修饰是发现新的杀菌剂候选物的有效途径。
Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture, To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, H-1 NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.