Esfenvalerate 顺式氰戊菊酯

顺式氰戊菊酯

基本信息
英文通用名称 esfenvalerate
其他名称 来福灵(Sumi-alpha)
毒性 顺式氰戊菊酯属中等毒性杀虫剂。原药大鼠急性经口LD50为325mg/kg，急性经皮LD50＞5000mg/kg，急性吸入LC50＞480mg/kg，对皮肤、眼睛的作用和慢性毒性参考氰戊菊酯。
剂型 来福灵5%乳油。
适用范围 与氰戊菊酯相同。

特点
顺式氰戊菊酯是活性较高的杀虫剂，仅含顺式异构体，此药作用机理、药效特点、防治对象与氰戊菊酯相同，其活性要比氰戊菊酯高出4倍。

使用方法
1、棉花害虫的防治 棉铃虫于卵孵盛期施药，棉红铃虫于第二、三代卵孵盛期施药，每亩用5%乳油25-35ml。
2、果树害虫的防治 柑橘潜叶蛾于柑橘各季新梢抽2-3cm时或卵孵盛期施药，使用5%乳油5000-8000倍液。 桃小食心虫于卵孵盛期，使用浓度为5%乳油1700-3000倍液。
3、蔬菜害虫的防治 菜青虫、小菜蛾于幼虫3龄期前施药，每亩用5%乳油15-30ml。 豆野螟于豇豆、菜豆开花盛期、卵孵盛期施药，每亩5%乳油20-30ml。
4、大豆害虫的防治 防治豆蚜于发生期施药，每亩用5%乳油10-20ml，防治效果良好。
5、茶树害虫的防治 茶尺蠖、茶毛虫于幼虫2-3龄发生期施药，用5%乳油7000-10000倍液对水喷雾。
6、烟草害虫的防治 防治烟草青虫于卵孵盛期或幼虫低龄期施药，每亩用5%乳油20-40ml。

注意事项
1、不要与碱性物质混合使用。
2、注意不要污染河流、桑园、养蜂场。
3、在害虫、害螨并发的作物上要与杀螨剂配合使用。

esfenvalerate
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name esfenvalerate (BSI, E-ISO, (m) F-ISO)
IUPAC name (S)-a-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
Chemical Abstracts name [S-(R*,R*)]-cyano(3-phenoxyphenyl)methyl 4-chloro-2-(1-methylethyl)benzeneacetate
Other names fenvalerate-U CAS RN [66230-04-4] Development codes S-1844; S-5602 Aa (both to Sumitomo); DPX-YB656 (DuPont) Official codes OMS 3023

PHYSICAL CHEMISTRY
Composition Tech. is ³98% total isomers and ³75% resolved (S,S)- isomers. Mol. wt. 419.9 M.f. C25H22ClNO3 Form Colourless crystals; (tech., yellow-brown viscous liquid or solid at 23 ºC). M.p. 59.0-60.2 ºC; (tech., 43.3-54 °C) B.p. 151-167 ºC (tech.) V.p. 2 ´ 10-4 mPa (25 ºC) KOW logP = 6.22 (25 ºC) Henry 4.20 ´ 10-2 Pa m3 mol-1 (calc.) S.g./density 1.26 (4-26 ºC) Solubility In water 0.002 mg/l (25 ºC). In xylene, acetone, chloroform, ethyl acetate, dimethylformamide, dimethyl sulfoxide >600, hexane 10-50, methanol 70-100 (all in g/kg, 25 ºC). Stability Relatively stable to heat and light. Stable to hydrolysis at pH 5, 7 and 9 (25 °C). Specific rotation [a]D25 -15.0?(c 2.0 in methanol) F.p. 256 °C (Pensky-Martens)

COMMERCIALISATION
History The enhanced insecticidal activity of esfenvalerate over fenvalerate reported by I. Nakayama et al. (Advances in Pestic. Sci., 1979, Part 2, p. 174), and its properties reviewed by H. Oo'uchi (Jpn. Pestic. Inf., 1985, No. 46, p. 21). Introduced by Sumitomo Chemical Co., Ltd and developed under licence by Shell International Chemical Co., Ltd and E. I. du Pont de Nemours and Co. 'Asana' registered by US EPA in 1986 and first marketed in 1987. Manufacturers JIE; Sharda; Sumitomo

APPLICATIONS
Biochemistry Voltage dependent sodium channel agonist. Mode of action Insecticide with contact and stomach action. Uses A potent contact and ingested insecticide with a very broad range of activity, especially effective against Coleoptera, Diptera, Hemiptera, Lepidoptera and Orthoptera on cotton, fruit, vegetables and other crops, at 5-25 g/ha. It is effective against strains resistant to organochlorine, organophosphorus and carbamate insecticides. Phytotoxicity Some injury has been noted on crucifers, cucumbers, aubergines, tomatoes, pears and mandarin oranges. Formulation types EC; SC; UL. Selected products: 'Asana' (DuPont); 'Sumi-alfa' (Sumitomo); 'Sumi-alpha' (Sumitomo); 'Fast' (Vapco); 'Vifen alpha' (Vipesco)

OTHER PRODUCTS
'Evercide 2668' (MGK); 'Halmark' (BASF); 'Mandarin' (Philagro) mixtures: 'Broxer' (+ fenitrothion) (Sumitomo); 'Kabuto' (+ pirimicarb) (Philagro)

ANALYSIS
Product and residue analysis commonly by glc or by hplc. Details available from Sumitomo. Analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 75-88 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000, rabbits >2000 mg/kg. Slight skin irritant; mild eye irritant. Not a skin sensitiser. NOEL No effect on sub-chronic studies at ³2 mg/kg daily. ADI 0.02 mg/kg. Other Acute LD50 values vary with the vehicle, concentration, route and species, etc.; values reported sometimes differ markedly. No carcinogenic, developmental or reproductive toxicity in animal tests. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification T; R23/25| R43| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 381 mg/kg. LC50 (8 d) for bobwhite quail >5620, mallard ducks 5247 ppm. Fish Extremely toxic to aquatic animals. LC50 (96 h) for fathead minnows 0.690, bluegill sunfish 0.26, rainbow trout 0.26 mg/l. Daphnia LC50 (48 h) 0.24 mg/l. Bees LD50 (contact) 0.017 mg/bee.

ENVIRONMENTAL FATE
Animals Rapid metabolism and elimination occurs in rats and other animals. Primary metabolism involves hydroxylation of 2'- and 4'- hydroxyl moieties, ester cleavage, hydroxylation and oxidation of the alcohol derivatives, oxidation of the cyano moiety and conjugation of the acidic metabolites with sulfate, glycine and glucuronic acid. Plants The major metabolite was decarboxylated fenvalerate. Ester cleavage, hydration of the cyano group to carboxamide and carboxylic acid, hydroxylation of the 2'- and 4'- phenoxy positions, conversion of the alcohol moiety to 3-phenoxybenzyl alcohol and 3-phenoxybenzoic acid, and conjugation of the resulting carboxylic acids and alcohols with sugars, also occur. Soil/Environment In sand (0.38% o.m.), Kd (25 ºC) 4.4; in sandy loam (pH 7.3, 1.1% o.m.), Kd (25 ºC) 6.4, DT50 88 d; in silty loam (pH 5.3, 2.0% o.m.), Kd (25 ºC) 71, DT50 114 d; in clay loam (pH 5.7, 0.2% o.m.), DT50 287 d; in clay loam (pH 6.4, 1.5% o.m.), Kd (25 ºC) 105. Koc 5300.