Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2-furanmethyl ester.
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.
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.
Ying
Y
Li
Bao-Ju
BJ
Li
Yun
Y
Ling
Hong-Jian
HJ
Miao
Yan-Xia
YX
Shi
Xin-Ling
XL
Yang
D002219:Carbamates / Q000737:chemistry*; D004952:Esters; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared
D002219:Carbamates; D004952:Esters; D005659:Fungicides, Industrial; C070766:carbamic acid