Azafenidin 唑啶草酮

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中文通用名称: 唑啶草酮
英文通用名称:azafenidin (BSI,ISO建议名)
商品名称:Evolus、Milestone
试验代号:DPX-R6447、R6447、IN-R6447
分子量: 338.2
分子工: C15H13CI2N3O2

化学名称:
2-(2,4-二氯-5-丙炔2-氧基苯基)-5,6,7,8-四氢-1,2,4-四唑并[4,3-a]吡啶-3(2H)-酮
2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one
CA主题索引名及CAS登录号:
2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one
[68049-83-2]

化学结构类型:三唑啉酮类
理化性质:纯品为铁锈色、具强烈气味的固体;熔点168~168.5℃;密度1.4(20℃);蒸气压为1.0×10-9Pa (25℃)。分配系数 LogP=2.7;水中溶解度为12ppm (pH 7)。对水解稳定,水中光照半衰期大约为12天。

毒性:大鼠急性经口LD50:>5000mg/kg;兔急性经皮LD50:>2000mg/kg;大鼠急性吸入LC50:5.3mg/l;本品对兔眼睛和兔皮肤无刺激。鱼毒LC50(96小时,mg/l):大翻车鱼48,虹鳟33;对水蚤 LC50(48小时):38mg/l。Ames等试验呈阴性,无致突变性。

制剂:80%W G。
作用机理:原卟啉原氧化酶抑制剂。
适宜作物:橄榄、柑桔、森林及不需要作物及杂草生长的地点等
安全性:在土壤中进行微生物降解和光解作用,无生物积累现象,对环境和作物安全。
防除对象:可防除许多重要杂草,阔叶杂草如苋、马齿苋、藜、芥菜、千里光、龙葵等;禾本科杂草如狗尾草、马唐、早熟禾、稗草等。对三嗪类、芳氧羧酸类、环己二酮类和ALS抑制剂如磺酰脲类除草剂等产生抗性的杂草有特效。
使用方法:在杂草出土前施用。使用剂量为100~200克有效成分/公顷。
合成方法:以2,4-二氯苯酚为起始原料,经醚化、硝化、还原制得中间体苯胺;经重氮化还原制得中间体取代苯肼,再与由氰戊氨基甲酸酯与乙酸酐制得的中间体反应,最后加热环合即得目的物。反应式为:

主要原料与中间体:2,4-二氯苯酚、炔丙基氯、氰戊氨基甲酸酯

分析方法:HPLC
开发公司:美国杜邦公司。

 

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azafenidin.
Superseded record no. 885

Azafenidin

CAS RN [68049-83-2]. Evaluated by DuPont Agricultural Products. Reported by L. Amuti et al., Proc. 1997 Br. Crop Prot. Conf. - Weeds , 1, p. 59.
Common names azafenidin (BSI, pa ISO) IUPAC name 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one CA name 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a ]pyridin-3(2H )-one. Development codes R6447; DPX-R6447; IN-R6447 (all DuPont) M.f. C15H13Cl2N3O2 Composition Tech. is c . 97% pure. Mol. wt. 338.2 Form White powdered solid; (tech. is a rust-coloured solid with a pungent odour). M.p. 168-168.5 °C V.p. 1 ´ 10-6 mPa (20 °C) KOW logP = 2.7 S.g./density 1.4 (20 °C) Solubility In water 16 ppm (pH 7). Stability Stable to hydrolysis; aqueous photolysis DT50 c . 12 h.
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Absorbed through the roots and shoots. Weakly xylem or phloem mobile, hence has limited post-emergence activity. However, it improves the efficacy of other post-emergence herbicides, such as glyphosate, and increases the speed of action of contact herbicides. Uses Intended for use as a pre-emergence, and, in mixture, post-emergence, herbicide in citrus, grapes, olives, sugar cane and other perennial crops; active on both annual and perennial weeds, and applied at 240 g/ha. Formulation types WG. Products 'Evolus' * (Europe) (DuPont); 'Milestone' * (USA) (DuPont) . Details PM12, Entry 43.