Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi 110 012, India.
J Agric Food Chem. 2010 Jan 27;58(2):1032-9. doi: 10.1021/jf903044j.
A number of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-alkyl ethers were prepared, separated into their E and Z isomers, and characterized on the basis of (1)H NMR and mass spectroscopy. These compounds were tested in vitro for antifungal activity against four important phytopathogenic fungi, namely, Sclerotium rolfsii , Rhizoctonia bataticola , Macrophomina phaseolina , and Sclerotinia sclerotiorum . E isomers of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-propyl ether (ED(50) = 32.36 microg mL(-1)) and 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-(1''-methyl) ethyl ether (ED(50) = 35.50 microg mL(-1)) showed maximum antifungal activity against R. bataticola and S. rolfsii, respectively, whereas 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether was found to be active against M. phaseolina (ED(50) = 31.08 microg mL(-1)) and S. sclerotiorum (ED(50) 21.39 microg mL(-1)), respectively. The Z isomer of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'-ketoxime N-O-pentyl ether, which was found to be most effective, was tested against S. sclerotiorum in a greenhouse at 1 and 5% concentrations. The 5% aqueous emulsion of 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-butene-2'(Z)-ketoxime N-O-pentyl ether suppressed disease development in pea by 90-95% as compared with the untreated infested soil in the greenhouse after 21 days of treatment.
合成了一系列 4'-(2,6,6-三甲基-2-环己烯-1-基)-3'-丁烯-2'-酮肟 N-O-烷基醚，对其 E 和 Z 异构体进行了分离，并基于 (1)H NMR 和质谱进行了表征。这些化合物在体外对四种重要的植物病原真菌进行了抗真菌活性测试，即 Sclerotium rolfsii、Rhizoctonia bataticola、Macrophomina phaseolina 和 Sclerotinia sclerotiorum。E 异构体 4'-(2,6,6-三甲基-2-环己烯-1-基)-3'-丁烯-2'-酮肟 N-O-丙基醚 (ED(50) = 32.36 μg mL(-1)) 和 4'-(2,6,6-三甲基-2-环己烯-1-基)-3'-丁烯-2'-酮肟 N-O-(1''-甲基)乙基醚 (ED(50) = 35.50 μg mL(-1)) 对 R. bataticola 和 S. rolfsii 表现出最大的抗真菌活性，而 4'-(2,6,6-三甲基-2-环己烯-1-基)-3'-丁烯-2'(Z)-酮肟 N-O-戊基醚则对 M. phaseolina (ED(50) = 31.08 μg mL(-1)) 和 S. sclerotiorum (ED(50) = 21.39 μg mL(-1)) 表现出活性。在温室中，以 1%和 5%的浓度测试对 S. sclerotiorum 最有效的 4'-(2,6,6-三甲基-2-环己烯-1-基)-3'-丁烯-2'-酮肟 N-O-戊基醚 Z 异构体，发现 5%的水溶液可抑制豌豆病害的发展，与温室中未处理的受感染土壤相比，处理 21 天后可抑制 90-95%的病害发展。
