Verbutin 增效炔醚

中文通用名称： 增效炔醚
英文通用名称： verbutin
商品名称： Censor
试验代号： MB-599
化学名称： ±-(3,4-dimethoxyphenyl)-2-ethylbut-2-ynyl ether ±-(3,4-二甲氧苯基)-2-乙基丁-2-炔基醚

CA主题索引名及CAS登录号
4-[1-(2-butynyloxy)ethyl]-3,4-dimethoxybenzene
[185676-84-0]

理化性质：
纯品为无色或浅黄色粘滞液体，沸点120℃/0.1mmHg。密度1.079。水中溶解度(25℃): 约1mg/l。在己烷中溶解度为20g/100ml，易溶于丙酮、二氯甲烷、苯等溶剂。在中性、碱性(40%氢氧化钠煮沸3小时)稳定，在盐酸中(pH=1，25℃) DT50：127.3小时。光照稳定，75瓦灯泡于254和356nm下照射16小时无变化。

毒性： 大鼠急性经口LD50：雄1290mg/kg，雌697mg/kg。大鼠急性经皮LD50：>2000mg/kg。大鼠吸入LC50(4小时)：雄 1.38mg/l，雌0.36mg/l。对兔皮肤无刺激，对兔眼睛有轻微的刺激。

作用机理： 细胞色素P-450抑制剂。
应用： 增效炔醚比增效醚、增效胺等增效剂具有更高的增效作用，当其与其它杀虫剂按如下比例混用时可显著的提高杀虫活性：0.5:1 、1:1、 2:1。几乎可与所有的杀虫剂混用如：有机磷、氨基甲酸酯、拟除虫菊酯；唑蚜威、吡虫啉、锐劲特、喹螨醚等。

合成方法：
经如下反应制得目的物：

分析方法： GC/HPLC
开发公司： 匈牙利Chinoin Agchem Business Unit

MB-599
Insecticide synergist

NOMENCLATURE
IUPAC name (RS)-but-2-ynyl 1-(3,4-dimethoxyphenyl)ethyl ether
Chemical Abstracts name 4-[1-(2-butynyloxy)ethyl]-1,2-dimethoxybenzene
Other names verbutin* (withdrawn BSI name proposal) CAS RN [185676-84-0] Development codes MB-599; Mi 18

PHYSICAL CHEMISTRY
Composition Tech. is ³95%. Mol. wt. 234.3 M.f. C14H18O3 Form Colourless or slightly yellow, viscous liquid. B.p. 120 °C/0.1 mmHg KOW logP = c. 2.4 S.g./density 1.079 Solubility In water c. 1 mg/l. In hexane 20 g/100 ml; miscible with acetone, dichloromethane and benzene. Stability Stable in neutral and basic (boiling 40% NaOH, 3 h) conditions; in HCl at pH 1, DT50 127.3 h (25 °C). Photochemically stable; practically no change after 16 h at 254 and 356 nm using 75W lamp. Stable up to 100 °C.

COMMERCIALISATION
History Reported by I. Székely et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1996, 2, 473). Under development by Chinoin Agchem Business Unit (now Agro-Chemie Pesticide Manufacturing Trading and Distributing Ltd). Manufacturers Agro-Chemie

APPLICATIONS
Biochemistry Blocks metabolism of insecticides by cytochrome P-450 inhibition. Uses Synergises a range of insecticides, aphicides and miticides. Selected products: 'Censor' (Agro-Chemie)

ANALYSIS
Product and residue analysis by glc. Details available from Agro-Chemie.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 1290, female rats 668 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Slight eye irritant; not a skin irritant (rabbits). Inhalation LC50 for male and female rats >5000 mg/m3. NOEL (90 d) for male rats 45 mg/kg daily, for female rats 52 mg/kg daily. Other Negative in CHO and Ames tests. Toxicity class WHO (a.i.) III (company classification)

ECOTOXICOLOGY
Birds Acute oral LD50 for Japanese quail >5400, mallard duck >5118 mg/kg. Fish LC50 (24 h) for rainbow trout 31.9 mg/l; (48 h) for rainbow trout 27.9 mg/l; (72 h) for rainbow trout 23.1 mg/l. Daphnia LC50 (24 h) 57.2 mg/l; (48 h) 39.9 mg/l. Algae EC50 59.7 mg/l. Bees LD50 (oral) >100mg/bee; (contact, 24 h) 87.3 mg/bee; (contact, 48 h) 73.8 mg/bee Worms LC50 (7 d) for earthworms 227.6 mg/kg soil.

ENVIRONMENTAL FATE
Soil/Environment 11-46% Of the substance was adsorbed, and 45-79% was desorbed, depending on the type of soil. Stable to hydrolysis at pH³7, unstable at pH£4.