A-Cyano-3-phenoxybenzyl

Synthetic pyrethroids now account for at least 30% of the world insecticide market and are rapidly replacing other agricultural chemicals for control of insect pests. Fenvalerate is one of the more widely used synthetic pyrethroid insecticides. It is derived from a combination of a-cyano-3-phenoxybenzyl alcohol and a-isopropyl phenylacetate ester. Technical fenvalerate is a mixture of four optical isomers, each occurring in equal amounts but with different efficacies against insect pests. Fenvalerate does not usually persist in the environment for >10 weeks, and it does not accumulate readily in the biosphere. Time for 50% loss (Tb 1/2) in fenvalerate-exposed amphibians, birds, and mammals was 6 to 14 h for reptiles, terrestrial insects, aquatic snails, and fish it was >14 h to <2 days and for various species of crop plants, it was 2 to 28 days. Fenvalerate degradation in water is due primarily to photoactivity, and in soils to microbial activity. Half-time persistence in nonbiological materials is variable, but may range up to 6 days in freshwater, 34 days in seawater, 6 weeks in estuarine sediments, and 9 weeks in soils. 

Chemical name (F S)-a-cyano-3-phenoxybenzyl(F S)-2-(4-chlorophenyl)-3-methylbutyrate cyano(3-phenoxyphenyl) methyl 4-chloro-a-(1-methylethyl) benzeneacetate a-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate 4-chloro-a-(1 -methylethyl) benzeneacetic acid cyano(3-phenoxyphenyl) methyl ester a-cyano-3-phenoxybenzyl a-(4-chlorophenyl) isovalerate... 

In general, these authorities agree that pyrethroids containing both a halogenated acid esterified with the a-cyano-3-phenoxybenzyl alcohol — such as fenvalerate, deltamethrin, and cyper-... 

Chemical Name (RS)-a-cyano-3-phenoxybenzyl(Z)-(l/ S, 3.RS)-(2-chloro-3,3,3-trifluoropropanyl)-2,2-dimethylcyclo-propanecarboxylate Uses insecticide CAS Registry No 68085-85-8 Molecular Formula C23H19C1F3N03 Molecular Weight 449.850 Melting Point (°C) ... 

Chemical Name cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclo-propanecarboxylate (RS)-a-cyano-3-phenoxybenzyl(lR5,3R5 lR5,35R)-3(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate Uses nonsystemic insecticide with contact and stomach action to control a wide range of insects in fruits, vegetables, vines, potatoes, cucurbits, capsicums, cereals, maize, soybeans, cotton, coffee, coca, rice, pecans, ornamentals and forestry, etc. also used to control flies in animal houses and mosquitoes, cockroaches, houseflies and other pests in public health. 

Chemical Name A-a-cyano-3-phenoxybenzyl (lR,3R)-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropan-1-carboxylate CAS Registry No 52918-63-5 Uses insecticide (pyrethroid)... 

Fenpropathrin [64257-84-7] Fensulfothion [115-90-2] Rody, Danitol, Meothrin, S-3206 Dassnit, Terracur (R,S)-a-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate 0,0-diethyl 0-4-methylsulphinylphenyl phosphorothioate c22h23no3 ChH1704PS2 349.423 308.354 47 0.608... 

Fenvalerate [51630-58-1] Sumicidin, Belmark, Pydrin (7 5 )-a-cyano-3-phenoxybenzyl ( 5 )-2-(4-chlorophenyl)-3-methylbutyrate c25h22cino2 419.901 liquid 1... 

Efficient biochemical processes were developed for the preparation of the two optically active pyrethroid insecticides by a combination of enzyme-catalyzed reactions and chemical transformations. These are based on the findings that a lipase from Arthrobacter species hydrolyzes the acetates of the two important secondary alcohols of synthetic pyrethroids with high enantioselectivity and reaction rate. The two alcohols are 4-hydroxy-3-methy1-2-(2 -propynyl)-2-cyclopentenone (HMPC) and a-cyano-3-phenoxybenzyl alcohol (CPBA). The enzyme gave optically pure (R)-HMPC or (S)-CPBA and the unhydrolyzed esters of their respective antipodes. 

CPBA is an alcohol moiety of highly potent synthetic pyrethroids such as fenvalerate ( a-cyano-3-phenoxybenzyl 2-(4-chloropheny1)-3-methyl-butyrate) or cyphenothrin (a-cyano-3-phenoxybenzyl chrysanthmate). 

S)-a-Cyano-3-phenoxybenzyl AM2-chloro-a,a-trifluoro-/ tolyl) D-valinate... 

The majority of pyrethroid insecticides have low volatilities. The heavily used synthetic pyrethroid permethrin is classified as nonvolatile on the basis of its vapor pressure (1.3 x 10 kPa at 20 °C) and is rarely found in indoor air. However, it has recently been reported to be the major pesticide residue found in house dust (USEPA, 2000d). Cyper-methrin [( )-a-cyano-3-phenoxybenzyl-( )-cA,frani -3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate] and cyfluthrin [cyano(4-fluoro-3-phenoxy-phenyl)methyl 3-(2,2-dichloro-ethenyl)-2,2-dimethylcyclopropanecarboxylate] are two other low-volatility pyrethroids commonly used for indoor flea and cockroach control. 

SYNS BELMARK a-CYANO-3-PHENOXYBENZYL-2-(4-CHLOROPHENYL)ISOVALERATE PYDRIN a-CYANO-3-PHENOXYBENZYL-2-(4-CHLOROPHENYL)-3-METHYLBUTYRATE CYANO(3-PHENOXYPHENYL)-METHYL4-CHLORO-a-(l-METHYLETHYL)BENZENE-ACETATE ECTRIN PHENVALERATE PYDRIN S 5602 SANMARTON SD 43775 SUMICIDIN SUMIFLY SUMIPOWR WX 43775... 

CYANON 5MSP see EHP700 a-CYANO-3-PHENOXYBENZYL-2-(4-CHLOROPHENYL)ISOVALERATE PYDRIN see FARIOO... 

Fenvalerate or (RS)-a-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbuty rate Pyrethroid Nonsystemic insecticide and acaricide with contact and stomach action Control of biting and boring insects in crops and flying and crawling insects in public areas 11-24... 

Racemic isomers of a-cyano-3-phenoxybenzyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate (64) were isomerized to 65 at the a-position by heating in /-propanol in the presence of DBU (81GEP3008986). 

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