Synthesis and fungicidal activities of novel indene-substituted oxime ether strobilurins.
Nineteen novel indene-substituted oxime ether strobilurins, which used an indene group to stabilize the ( E)-styryl group in SYP-Z071 (an unsaturated oxime strobilurin fungicide under development by the Shenyang Research Institute of Chemical Industry), were designed and synthesized. The biological assay results showed that all compounds possessed good or excellent fungicidal activities. It was found that most of the compounds showed higher fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Erysiphe graminis, and Colletotrichum lagenarium than SYP-Z071 at the tested concentration. The biological assay results also indicated that most of the compounds exhibited higher in vivo fungicidal activities against cucumber Pseudoperonospora cubensis and C. lagenarium than the commercial fungicides trifloxystrobin and kresoxim-methyl at a concentration of 6.25 mg/L. Furthermore, it was found that alpha-(methoxyimino)- N-methylphenylacetamide oxime ethers 6m- s exhibited a broad spectrum and remarkably higher activities against all tested fungi. Especially, the 6-methylindene-substituted compound 6p was identified as the most promising candidate for further study.
Tu
Song
S
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China. tusong_2001@hotmail.com
Xu
Long-He
LH
Ye
Li-Yi
LY
Wang
Xi
X
Sha
Yong
Y
Xiao
Zong-Yuan
ZY
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004987:Ethers; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000179:Acrylates; D004987:Ethers; D005659:Fungicides, Industrial; D007192:Indenes; D010091:Oximes; C093581:indene