Pentoxazone 环戊恶草酮

中文通用名称： 环戊恶草酮
英文通用名称： pentoxazone （BSI,ISO）
商品名称： Wechser
试验代号： KPP314
化学名称：
3-(4-氯-5-环戊氧基-2-氟苯基)-5-异丙基烯-1,3-恶唑啉-2,4-二酮
3-(4-chloro-5-cyclopentyloxyl-2-fluorophenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione
CA主题索引名及CAS登录号：
3-[4-dichloro-5-(cyclopentyloxyl)-2-fluorophenyl]-5-(1-methylethylidene)-1,3-ox-azolidine-2,4-dione
[110956-75-7]

化学结构类型： 恶唑啉酮类
理化性质： 纯品为无色、无味粉状固体；熔点104℃；密度1.418(25℃)；蒸气压为<1.11×10-5Pa (25℃)。分配系数 LogP＝0.67；水中溶解度为0.216 mg/l(25℃)；对光、热、酸稳定性，对碱不稳定。

毒性： 大鼠急性经口LD50：雄、雌>5000mg/kg；小鼠急性经口LD50：雄、雌>5000mg/kg；雄、雌大鼠急性经皮LD50：>2000mg/kg； 大鼠急性吸入LC50(4小时)>5100mg/l。鹌鹑急性经口LD50：雄、雌>2250mg/kg； 鲤鱼LC50(96小时)：21.4mg/l；水蚤 LC50(48小时)：>38.3mg/l。

制剂： SC、 G R。还可与唑吡嘧磺隆、吡嘧磺隆、环胺磺隆、杀草隆等混用。
作用机理： 原卟啉原氧化酶抑制剂。
适宜作物： 水稻
安全性： 对水稻极安全。
防除对象： 主要用于防除防除稗草和一年生杂草等。
使用方法： 主要用于水稻防除稗草和一年生杂草。苗前施用，用量为200~450克有效成分/公顷。

合成方法： 以对氟苯酚为起始原料，经氯化、酯化、硝化制得中间体取代的硝基苯；经水解制得中间体取代的苯酚钾盐；再经醚化、还原制成取代的苯胺；最后与氯甲酸乙酯反应
后，与异戊烯酸酯缩合即得目的物。反应式为：

主要原料与中间体： 对氟苯酚、氯甲酸乙酯、环戊基溴、异戊烯酸酯
分析方法： HPLC
开发公司： 日本科研制药公司开发。
专利申请： JP 02 85269

pentoxazone
Herbicide
HRAC E WSSA 14; oxazolidinedione

NOMENCLATURE
Common name pentoxazone (BSI, pa ISO)
IUPAC name 3-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione
Chemical Abstracts name 3-[4-chloro-5-(cyclopentyloxy)-2-fluorophenyl]-5-(1-methylethylidene)-2,4-oxazolidinedione
CAS RN [110956-75-7] Development codes KPP-314 (Kaken)

PHYSICAL CHEMISTRY
Mol. wt. 353.8 M.f. C17H17ClFNO4 Form Colourless, odourless, crystalline powder. M.p. 104 °C V.p. <1.11 ´ 10-2 mPa (25 °C) KOW logP = 4.66 (25 °C) Henry <1.82 ´ 10-2 Pa m3 mol-1 (calc.) S.g./density 1.418 (25 °C) Solubility In water 0.216 mg/l (25 °C). In methanol 24.8, hexane 5.10 (both in g/l). Stability Stable to heat, light and acid; unstable in alkali.

COMMERCIALISATION
History Discovered in 1986 by Sagami Chemical Research Center, and developed by Kaken Pharmaceutical Co., Ltd. First registered in Japan in 1997. Manufacturers Kaken

APPLICATIONS
Biochemistry Protoporphyrinogen oxidase inhibitor. This enzyme catalyses the conversion of protoporphyrinogen IX to protoporphyrin IX in plant chlorophyll biosynthesis. Uses Pre- and post-emergence control of Echinochloa spp. and Monochoria vaginalis in rice, at 150-450 g/ha. Formulation types EW; GR; SC; WG. Selected products: 'Wechser' (Kaken); mixtures: 'Kusabue' (+ cumyluron) (Marubeni, Yashima, Nissan, Kaken); 'Shokinie' (+ bromobutide) (Kumiai); 'Topgun' (+ pyriminobac-methyl+ bensulfuron-methyl+ bromobutide) (Kumiai)

OTHER PRODUCTS
Mixtures: 'Kusa Punch' (+ daimuron) (Kaken); 'Sakidori' (+ butachlor) (Kaken, Kumiai); 'Staabo' (+ pyrazosulfuron-ethyl) (Kaken, Nissan); 'Tema Cut' (+ daimuron) (Kaken); 'The-One' (+ daimuron+ imazosulfuron) (Kaken, Sumitomo Chemical Takeda); 'Focus Shot' (+ benzobicyclon) (SDS Biotech KK, Kaken); 'Utopia' (+ cyclosulfamuron) (BASF, Kaken)

ANALYSIS
By hplc.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats, and male and female mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Not a skin or eye irritant (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male and female rats >5100 mg/m3. NOEL for male rats 6.92, female rats 43.8 mg/kg b.w. daily; for male mice 250.9, female mice 190.6 mg/kg b.w. daily; for male dogs 23.1, female dogs 25.2 mg/kg b.w. daily. Other Not carcinogenic or teratogenic; negative in Ames, DNA repair and micronucleus tests.

ECOTOXICOLOGY
Birds Acute oral LD50 for male and female bobwhite quail >2250 mg/kg. Fish LC50 (96 h) for carp 21.4 ppm. Daphnia LC50 (24 h) >38.8 ppm. Algae EC50 (72 h) for Selenastrum capricornutum 1.31 ppb. Bees LC50 (oral) >458.5 ppm; (contact) 98.7 mg/bee. Worms LC50 (14 d) >851 ppm. Other beneficial spp. LC50 (96 h) for silkworms >458.5 ppm.

ENVIRONMENTAL FATE
Animals Male and female rats excrete >95% of administered dose, mainly via the faeces, within 48 h. Soil/Environment In soil, DT50 <29 d (two types of flooded soil, 28 °C). In water, DT50 1.4 d (pH 8.0, 20 °C). Soil Koc 3160.