Synthesis And Activity Study Of Oxadiazine Derivatives Containing Heterocyclic Groups

With novel structure, unique mechanism of action, almost all of the lepido pteran pests effective, etc., oxadiazine compounds become a new star in hetero cyclic insecticides. However, 1,3,4-oxadiazine ring reported relatively small of o xadiazine compounds. 1,3,4-oxadiazine ring have insecticidal, fungicidal, weedin g, cancer and other broad biological activity. In the field of pesticides, there w as successfully developed drug(Indoxacarb), which had a unique mechanism of action, safety to non-target organisms.simple structure and so on.In order to develop high-efficien, safe and economical, friendly drugs, in t his paper, we regarded Indoxacarb as the leading compound, maintained the 1,3,4-oxadiazine structure, and then, replaced the carbamateit by different substitut ed 1,3,4-thiadiazole ring or 1,3,4-oxadiazole ring compound. All the compounds were confirmed by IR, 1H NMR, 13 C NMR, MS.Bioassay, we tested Fusarium graminearum, Botrytis cinerea, and eggplant wilt fungus, Xanthomonas oryzae, Xanthomonas citri by means of growth in v itro.Fungal bioassay results indicated that compound 7-chloro-2(5-(4-isopropyl-p henyl-1,3,4-oxadiazol-2,5-dihydro-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carb oxylicacidmethylester, 2-(5-(t-butyl)-1,3,4-thiadiazol-2-yl)-7-chloro-2,5-dihydro-inde no[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacidmethylester, at 50 μg/mL c oncentration, showed inhibition rate above 60% against Botrytis cinerea.Preliminary bacterial bioassay results indicated that, some of the target co mpounds prosessed obvious bacterial activity against Xanthomonas oryzae. At a concentration of 200 μg/mL, compound 2-(5-(bromomethyl)-1,3,4-oxadiazol-2-yl)-7- chloro-2,5-dihydro-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacidmethyle ster displayed over 90% inhibition against rice leaf blight, better than Bismerth iazol(72.12±0.65%). At the concentration of 100 μg/mL, the compound 2-(5-(b romomethyl)-1,3,4-oxadiazol-2-yl)-7-chloro-2,5-dihydro-indeno [1,2-e] [1,3,4] oxa diazine-4a(3H)-carboxylicacidmethylester displayed 89.8% inhibition rate againstXanthomonas oryzae, better than Bismerthiazol(53.7%). Compound 7-chloro-2-(5-(2-chloro-3-yl)-1,3,4-oxadiazol-2-yl)-2,5-dihydro-indeno[1,2-e][1,3,4]oxadiazine-y l-4a(3H)-carboxylicacidmethylester,7-chloro-2-(5-methyl-1,3,4-thiadiazol-2-yl)-2,5-d ihydro-indeno[1,2-e][1,3,4]oxadiazine-yl-4a(3H)-carboxylicacidmethylester,7-chloro-2-(5-(pyridin-2-yl)-1,3,4-thiadiazol-2-yl)-2,5-dihydro-indeno[1,2-e] [1,3,4]oxadiazin e-yl-4a(3H)-carboxylicacidmethylester displayed over 46% inhibition rate against Xanthomonas oryzae, close to Bismerthiazol(53.7%).At the concentration of 200 μg/mL, compound 7-chloro-2-(5-(4-isopropylph enyl)-1,3,4-oxadiazol-2-yl)-2,5-hydrogen-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carb oxylicacidmethylester,7-chloro-2-(5-(chloromethyl)-1,3,4-oxadiazol-2-yl)-2,5-dihydr o-indeno[1,2-e][1,3,4]oxadiazine-yl-4a(3H)carboxylicacidmethylester,2-(5-(bromome thyl)-1,3,4-oxadiazol-2-yl)-7-chloro-2,5-dihydro-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacidmethylester displayed over 50% inhibition against Xanthomonas citri.