Chemical Properties
This product is a brownish yellow slightly viscous liquid with slightly aromatic odor. b.p.>150℃/13.3 Pa, flash point 145℃, relative density Fang1.28 (20℃), vapor pressure 1.9×10-3 Pa (25℃). 20℃ solubility: acetone, ethyl acetate, chloroform, ether, dimethylformamide, isopropanol, toluene are>200g/L, hexane< ;1g/L, water 115mg/L (pH=7). Stable at room temperature and under UV light. Hydrolyzed at 50°C at pH 3, 7 and 9.
Uses
Agricultural fungicide.
Definition
ChEBI: An oxime O-ether that is the O-methyloxime of 2',4'-dichloro-2-(3-pyridyl)acetophenone. A fungicide used for control of powdery mildew, scab and other fungal pathogens on a range of crops.
Mechanism of action
Systemic with protective and curative action. Disrupts membrane function.
Synthesis
1) Preparation of 2' , 4 ` -dichloro-2 -( 3 - pyridinyl) acetophenone oxime ( 2): 10g of 2', 4'-dichloro-2-(3-pyridinyl) acetophenone (l), 10g of leucoammonium hydrochloride, 12g of anhydrous sodium carbonate and 100ml of Methanol was heated to 60C and the reaction was stirred for 2 h. The resulting mixture was treated with water and extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated; the residue was recrystallized with acetone/n-hexane to obtain the intermediate (2)
2) Synthesis of 2`,4'-dichloro-2-(3-pyridyl)acetophenone-O-methyl oxime: the intermediate (2) obtained from the reaction of the previous step was dissolved in 25 ml of ethylene glycol bis(methyl ether), with 51 g of sodium hydride (dispersed in oil, content of 5%), and this mixture was stirred at room temperature for 30 min, and then added 2.0 g of Iodomethane, heating to reflux, keep refluxing 4h, the mixture is poured into ice water, acetate ethyl cool extraction, the organic layer is dried with anhydrous sodium sulfate, filtration, filtrate concentration under reduced pressure, the crude product by column chromatography refinement that is the amidinium zebra oxime.
