Fenapanil

Fenapanil is an imidazole fungicide.

Preparation method 1: Preparation of α-n-butylbenzeneacetonitrile. After mixing 119.2g of 98% 2-phenylacetonitrile, 185.2g of chlorobutane, and 1.61g of phase transfer catalyst tetrabutylammonium bromide, the mixture was stirred for 10 minutes Drop 160g of 50% sodium hydroxide into the inside. Due to the exothermic reaction, the temperature rose to 88°C within 1 hour, then refluxed, and then cooled to 65°C. After the reaction was kept at 4.5g, 300mL of water was added, and the layer was stirred for post-treatment. The product was 163.2g, the yield was 85%, and the content was 90.5%. According to reports, if the PTCA phase transfer catalyst is used and the operating conditions are changed, the temperature is lowered to 85°C for 6-7 hours after refluxing, the product content is 98%, and the yield is 88%, which is significantly higher than the literature value. Preparation of 1-chloro-2-cyano-2-phenylhexane. After mixing 91g of 98% α-n-butylbenzeneacetonitrile, 85g of dichloromethane, and 6.5g of tetrabutylammonium bromide, within 20 minutes 160g of 50% sodium hydroxide solution was dropped into the reaction, the reaction exothermed, and the temperature was raised to 65°C and the reaction was refluxed for 4.5 hours. After post-treatment, 109.5g of the product was obtained, the content was 96%, and the yield was 92%. Synthesis of pyraclonil: Mix 87.6 g of 50% sodium hydroxide, 132 g of imidazole, and 200 g of dimethyl sulfoxide, and then raise the temperature to 85°C. Remove the front fraction under reduced pressure. When the reaction temperature reaches 120°C, part of the low-boiling substance is evaporated. (About 2h), then heat to 135℃, add 109g of 1-chloro-2-cyano-2-phenylhexane dropwise in 1h to complete, keep the reaction at 135℃ for 8h, after post-treatment, the content is 60% 198g of pyraclonil viscous liquid, yield 99%. Preparation method Di-2-phenylcapronitrile is hydroxymethylated with polyformaldehyde, and the obtained alcohol is then converted into methyl sulfonate, and finally, it reacts with imidazole to obtain fidaronil.

Broad-spectrum, systemic imidazole fungicides are inhibitors of ergosterol biosynthesis. It has good activity on various fungi such as ascomycetes, basidiomycetes, semi-intelligent fungi. It is used to control wheat rust, rust stem disease, broad bean gray mold, apple ring rot and black spot, cotton wilt, stand blight, rape sclerotium, rice flax spot, rice blast, sheath blight and certain Powdery mildew of some crops. Generally, the active ingredient is sprayed with 0.03% to 0.12%, which can effectively prevent powdery mildew.

Molecular Weight:253.34
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:253.157897619
Monoisotopic Mass:253.157897619
Topological Polar Surface Area:41.6
Heavy Atom Count:19
Complexity:313
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes