Department of Applied Chemistry, College of Science, Key Laboratory of Pesticide Chemistry and Application, MOA, China Agricultural University, Beijing 100193, People's Republic of China.
J Agric Food Chem. 2010 Mar 10;58(5):3037-42. doi: 10.1021/jf9043277.
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, (1)H 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.
几丁质是昆虫外骨骼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，因此被认为是防治害虫的安全且有选择性的靶标。几丁质合成抑制剂（CSIs）作为昆虫生长调节剂（IGRs）已广为人知，但在农业中很少作为杀菌剂使用。为了寻找具有良好活性的新型 CSI，选择苯甲酰基苯脲作为先导化合物，通过将苯甲酰基苯脲的脲键转化为氨基甲酸酯键，并将苯胺部分改为呋喃甲基，设计了 26 种新型芳基氨基甲酸 5-芳基-2-呋喃甲酯。通过红外光谱（IR）、（1）H NMR 和元素分析对标题化合物进行了合成和结构确证。初步的杀虫和杀菌生物测定表明，这些标题化合物对淡色库蚊和小菜蛾没有杀虫作用，但大多数化合物对姜疫病菌、瓜类炭疽病菌、灰葡萄孢和尖孢镰刀菌表现出良好的杀菌活性。特别是化合物 V-4、V-6、V-7 和 V-8 对四种菌株的活性优于商品化杀菌剂。形态学结果表明，化合物 V-21 扰乱了姜疫病菌的细胞壁形成。结果表明，对苯甲酰基苯脲脲键的修饰是发现新杀菌剂候选物的有效途径。
