New Proxetil Fungicides Synthesis And Antimicrobial Properties

In this paper, A new Oxime esters compound which was named Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate was prepared with benzene and Ethyl chloride glyoxylate,α-pinene as raw materials by Hydroboration-Oxidation reaction, Friedel-Crafts Acylation reaction, Oximation reaction and Ester-exchange reaction. The results of the bacteriostasis activities of this new type compound for the fungal were obtained by using the disk diffusion, and the results indicated that the Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate have good bacteriostasis activities and the performance similar to the counterpoint—azoxystrobin.(1)The reaction conditions of Isopinocampheol were obtained as follows:V(tetrahydrofuran)=50mL, n(sodium borohydride)=0.09mol, the molar ratio of sodium borohydride toα-pinene to boron trifluride ether solution to sodium hydroxide to 30% hydrogen peroxide 9:20:12:36:21, Hydroboration reaction was carried out as follows: reaction temperature 40℃, reaction time 6h, followed by the Oxidation reaction, Oxidation reaction was carried out as follows: reaction temperauter 50℃, reaction time 1h. The yield was 91.15%.(2)The reaction conditions of Ethyl phenyl glyoxylate were obtained as follows: n(ethyl chloride glyoxylate) =0.36mol, the molar ratio of benzene to aluminum trichloride to ethyl chloride glyoxylate 6:1.3:1, reaction temperature 20℃, reaction time 3h. The yield was 96.17%.(3)The reaction conditions of ethyl 2-(N-methoxy)imino-2-phenylacetate were obtained as follows:n(Ethyl phenyl glyoxylate)=0.02mol, n(Methoxy amine hydrochloride)=0.04mol, the molar ratio of methoxyamine Methoxy amine hydrochloride to sodium carbonate to sodium acetate 1:1:0.3, V(absolute ethyl alcohol)=30mL. The reaction temperature was the reflux temperature of abosolute ethyl acohol, The reaction time was 12h. The yield was 92.25%.(4)The reaction conditions of Isopinocampheyl 2-(N-methoxy)imino-2-phenylac- tate were obtained as follows:The reaction temperature was 120~130℃,n(Isopinocampheol)=n(Sodium ethylate)=0.03mol, n(ethyl 2-(N-methoxy)imino-2-phenylacetate)=0.02mol, The reaction that used Sodium ethylate as catalyst was monitored by TLC, which would be ended if the material point disappeared. Yellow liquid product was abtained by column chromatography separation [V(petroleum ether):V (ethyl acetate) = 10:1 as the developing solvent]. The yield of Isopinocampheyl 2-(N-methoxy)imino-2-phenyl acetate was 47.62%.The synthetic structure that confirmed by means of IR(Infrared Spectrometry), 1HNMR(1H Nuclear Magnetic Resonance), 13CNMR(13C Nuclear Magnetic Resonance)was consistent with the molecular structure of designed target product.