Etoxazole 乙螨唑

中文通用名称: 乙螨唑
英文通用名称: etoxazole
商品名称: Baroque、Biruku(混剂)、Flowable、Virk
化学名称: (RS)-5-tert-butyl-2-[2-(2,6-difluorophenyl)-4,5-dihydro-1,3-oxazol-4-yl]phene-tole
(RS)-5-叔-丁基-2-[2-(2,6-二氟苯基)-4,5-二氢-1,3-恶唑-4-基]苯乙醚

CA主题索引名及CAS登录号:
2-(2,6-difluorophenyl)-4-[4-(1,1-dimethylethyl)-2-ethoxyphenyl]- 4,5-dihydroox-azole
[153233-91-1]

化学结构类型: 恶唑啉类
理化性质: 纯品为白色粉末，熔点101-102℃，密度1.24(20℃)。蒸气压2.18×10-6Pa(25℃)，分配系数(25℃) LogP＝5.59。溶解度(20℃，g/l) 水7.54×10-5
、甲醇 90、乙醇90、丙酮300、环己酮 500、乙酸乙酯 250、二甲苯 250、正己烷 13、乙腈80、四氢呋喃 750。在50℃下贮存50天不分解，对碱稳定。
毒性: 大鼠(雄、雌)急性经口LD50：>5000mg/kg，小鼠(雄、雌)急性经口LD50：>5000mg/kg; 大鼠(雄、雌)急性经皮LD50：>2000mg/kg；大鼠(雄、雌)急性吸入LC50(4小时)：>1.09mg/l；本品对兔眼睛和皮肤无刺激。无致突变性。鹌鹑LD50：>5200mg/kg, 麻鸭LD50：>2000mg/kg；虹鳟LC50(48小时)：>40ppm；水蚤EC50
(48小时)：>40ppm；蜜蜂LC50：>200微克有效成分/蜂。

制剂: 10%SE
作用机理: 触杀型杀螨剂。抑制螨和蚜虫的蜕皮。
适宜作物及对作物的安全性: 水果、蔬菜、茶等如黄瓜、茄子、西瓜、甜瓜、草莓，柑桔、苹果，犁、桃、樱桃等；推荐剂量下对作物、环境安全、无药害。
防治对象: 对多种叶螨的卵、幼虫、若虫有卓效，对成螨无效。
使用方法: YI 5301无内吸活性，虽对成螨无效，但可抑制螨卵孵化，持效期长达30天以上。通常用于茎叶处理，使用剂量为50-100g a.i./ha。

合成方法:
乙螨唑可由如下反应制备：

主要原料与中间体: 取代的苯甲醛、2,6-二氟苯甲酰氯
分析方法: HPLC
开发公司: 日本八州化学公司
登记: 已在欧洲登记

etoxazole
Acaricide
IRAC 10B; mite growth inhibitor

NOMENCLATURE
Common name etoxazole (BSI, pa ISO)
IUPAC name (RS)-5-tert-butyl-2-[2-(2,6-difluorophenyl)-4,5-dihydro-1,3-oxazol-4-yl]phenetole
Chemical Abstracts name 2-(2,6-difluorophenyl)-4-[4-(1,1-dimethylethyl)-2-ethoxyphenyl]-4,5-dihydrooxazole
CAS RN [153233-91-1] Development codes YI-5301 (Yashima); S-1283 (Sumitomo)

PHYSICAL CHEMISTRY
Composition Tech. is 93-98%. Mol. wt. 359.4 M.f. C21H23F2NO2 Form White, crystalline powder. M.p. 101-102 ºC V.p. 2.18 ´ 10-3 mPa (25 ºC) KOW logP = 5.59 (25 ºC) S.g./density 1.24 (20 °C) Solubility In water 75.4 mg/l (20 ºC). In acetone 300, methanol 90, ethanol 90, cyclohexanone 500, tetrahydrofuran 750, acetonitrile 80, ethyl acetate 250, xylene 250, n-hexane 13, n-heptane 13 (all in g/l, 20 ºC). Stability No decomposition after 30 d (50 ºC). Stable in alkali. F.p. 457 °C (ASTM E 659)

COMMERCIALISATION
History Discovered by Yashima Chemical Industry Co., Ltd and reported by T. Ishida et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1994, 1, 37). Registered in Japan in 1998. Under joint development by Yashima and Sumitomo Chemical Co., Ltd. Patents EP 0639572 B1, US 5478855, JP 3189011 Manufacturers Yashima

APPLICATIONS
Mode of action Contact acaricide. Appears to inhibit moulting of mites and aphids. Uses Non-systemic acaricide with effect on eggs, larvae and nymphs, with no effect on adults. Controls many phytophagous mites (Tetranychus, Panonychus spp.) in citrus, pome fruit, vegetables and strawberries, at 50 g/ha, and in tea, at 100 g/ha. Formulation types SC; Smoking agent. Compatibility Cannot be mixed with Bordeaux mixture. Selected products: 'Baroque' (Yashima); mixtures: 'Biruku' (+ fenpropathrin) (Yashima, Sumitomo)

OTHER PRODUCTS
'Borneo' (Philagro); 'Secure' (Valent Biosciences); 'Zoom' (Valent) mixtures: 'Virk' (+ fenpropathrin) (Yashima, Sumitomo)

ANALYSIS
Product and residue analysis by hplc.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg; no skin or eye irritation (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 for male and female rats >1.09 mg/l. NOEL NOEL for rats 4.01 mg/kg b.w. daily. ADI 0.04 mg/kg b.w. Other Negative in Ames test.

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >2000 mg/kg. Sub-acute oral LD50 (5 d) for bobwhite quail >5200 ppm diet. Fish LC50 (96 h) for Japanese carp 0.89 mg/l; (48 h) for Japanese carp >20, rainbow trout >40 ppm. Daphnia LC50 (3 h) >40 ppm. Algae EC50 for Selenastrum capricornutum >1.0 mg/l. Other aquatic spp. Disruption of moulting was observed in aquatic arthropods. Bees LD50 (oral and contact) >200 mg/bee. Worms NOEL (14 d) for Eisenia foetida >1000 ppm.

ENVIRONMENTAL FATE
Soil/Environment In Japanese alluvial soil, DT50 19 d, DT90 90 d.