Synthesis And Antifungal Bioactivity Of Methyl 2-Methoxyimino-2-Phenyl N-Methyl Acetamide Derivatives Containing Double Oxime Structures & 1H-1,2,4-Triazol-1-YL

In the process of the creation of new pesticides, it is an effective way to modify the structures of nature products as lead compounds. As a part of the ecosystem, nature products have a good adaptability and compatibility with the environment. Compared with the traditional synthetic compounds, the structures of nature products can be flexibly changed. Strobilurin Fungicides derived from natural products have become a series of highly potential and active agricultural fungicides after the development of 1H-1,2,4-triazol-1-yl fungicides. They don’t produce cross resistance with the other fungicides in the domestic market. And they only use a little in the fields and have a broad-spectrum of biological activities. In plants, soil and water, they can be degraded soon. At present, the Strobilurin Fungicides have become one of active research fields because of their prevention, care, eradication and infiltration action with no carcinogen and mutagen.In this dissertation, we chose and changed the structures of the side chain of Kresoxim-methyl and Metominostrobin been as the lead compounds. By adopting the connection method of active group, Oxime & 1H-1,2,4-triazolyl, a series of methyl 2-metho- xyimino-2-phenylacetate and 2-methoxyimino-2-phenyl-N-methylacetamide derivatives have been synthesized. At the same time, the synthesis methods were discussed, the target compounds’structures were conformed and the preliminary bioassays of fungicidal activity of all the compounds were evaluated. The main results of the research are as follows:1. The optimization conditions of 2-methyl phenyl glyoxylate as an important intermediate were presented. This intermediate was prepared by reaction of 3 steps synthetic method. Afterwards, the structures of the intermediate were identified by IR,1H NMR and GC-MS. The advantage of the synthetic method is that the product is easily separated and has a high yield and good purity.2.6 series in 3 classes (total 64) of target compounds (methyl 2-methoxyimino-2-phenylacetate and 2-methoxyimino-2-phenyl-N-methylacetamide derivatives) have been designed and synthesized. All the structures were presented and confirmed by IR,1H NMR, GC-MS. The classes are followed:(1) Methyl 2-methoxyimino-2-[2-(subsititued phenyl methyliminoxyl methyl) phenyl] acetate:(Ga1-Ga10),10 new compounds;(2) 2-methoxyimino-2-[2-(subsititued phenyl methyliminoxyl methyl)phenyl]-N-methylacetamide:(Gb1-Gb10),10 new compounds;(3) Methyl 2-methoxyimino-2-[2-(subsititued phenyl ethyliminoxyl methyl) phenyl] acetate:(Gc1-Gc11),11 new compounds;(4) 2-methoxyimino-2-[2-(subsititued phenyl ethyliminoxyl methyl)phenyl]-N-methylacetamide:(Gd1-Gd11),11 new compounds;(5) Methyl 2-methoxyimino-2-{2-[1-subsititued phenyl-2-(1H-1,2,4-triazol-1-yl) acetone]}phenyl acetate:(Ja1-Ja11),11 new compounds;(6)2-methoxyimino-2-{2-[1-subsititued phenyl-2-(1H-1,2,4-triazol-1-yl) acetone]}-N-methyl acetamide:(Jb1-Jb11),11 new compounds.The general formulas of the target compounds are as follows: 3. The preliminary bioassay of fungicidal activity of all the target compounds has been evaluated. The results of the test to all the compounds have been shown below:(1) Gd4, Ja7, Ja5, Ja4 compounds exhibit fungicidal activity against Sclerotonia. But Their fungicidal activities are lower than Kresoxim-methyl and Carbendazim.(2) Gc10,Gd4,Gb7,Gb6,Jb4,Gb5,Gd11,Gb8 compounds exhibit fungicidal activity against Botrytis cinerea. Gc10、Gd4、Gb7、Gb6 of them is nearly equal to Kresoxim-methyl.(3) Gc10,Jb4，Gd11,Gb7 compounds exhibit fungicidal activity against Gibberella zeae. Their activity is nearly equal to Kresoxim-methyl.(4) Gd4,Jb4,Gc10,Gb7,Gd11 compounds exhibit fungicidal activity against Rhizoctorua solani. Their activity is better than Kresoxim-methyl, and less than Carbendazim.(5) Gc10,Ga1 compounds exhibit fungicidal activity against Pyricularia oryzae. Their activity is nearly equal to Kresoxim-methyl, and less than Carbendazim.Gc10,Gd4,Gd11,Jb4,Gb7 of target compounds above present prevalent fungicidal activity for Sclerotonia,Botrytis cinerea, Gibberella zeae, Rhizoctorua solani, Pyricularia oryzae. Ja7,Ja5,Ja4,Ga1,Gb6,Gb5,Gb8 present partial fungicidal activity for the tested strain. Their structures could be designed and optimized according to the request.