Flumiclorac-pentyl 氟胺草酯

中文通用名称： 氟胺草酯
英文通用名称： flumiclorac-pentyl （BSI,ISO）
商品名称： Resource
试验代号： S-23031、 V-23031
化学名称： [2-氯-5-(环己-1-烯-1,2-二羧酰亚胺基)-4-氟苯氧基]乙酸戊酯
pentyl [2-chloro-5-(cyclohex-1-ene-1,2-dicarboxamido)-4-fluorophenoxy]acetate
CA主题索引名及CAS登录号：
[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid pentyl ester
[87546-18-7]
化学结构类型： 酰亚胺类
理化性质： 纯品为白色粉状固体；熔点88.9~90.1℃；密度1.33(20℃)；蒸气压为<1.0×10-5Pa(25℃)。分配系数 LogP＝4.99(20℃)；水中溶解度为0.189mg/l(25℃)；其它溶剂中溶解度(g/l，25℃)：甲醇47.8，丙酮590，正辛醇16.0；正己烷3.28。水中半衰期为4.2天(pH5)、19小时(pH 7)、6分钟(pH 9)。

毒性： 大鼠急性经口LD50：>3.6g 0.86EC/kg；兔急性经皮LD50：>2.0g 0.86EC/kg； 本品对兔眼睛和兔皮肤有中度刺激刺激。大鼠急性吸入LC5050(4小时)：5.51 mg 0.86EC/l。鹌鹑急性经口LD50：>2250mg/kg；鹌鹑和野鸭LC50：>5620ppm； 鱼毒LC50(96小时，mg/l)：虹鳟1.1，大翻车鱼13~21。无致突变性、无致畸性。

制剂： 10％乳油。
作用机理： 原卟啉原氧化酶抑制剂。药剂被敏感杂草叶面吸收后，迅速作用于植株组织，引起原卟啉积累，使细胞膜脂质过氧化作用增强，从而导致敏感杂草的细胞膜结构和细胞功能不可逆损害。阳光和氧是除草活性必不可少的。常常在24~48小时出现叶面白化、枯斑等症状。
适宜作物： 大豆、玉米等
安全性： 对大豆和玉米安全。其选择性是基于药剂在植株中的代谢。
防除对象： 主要用于防除阔叶杂草如苍耳、藜、豚草、苋属杂草、苘麻、曼陀螺、斑地锦、黄花稔等。
使用方法： S-23031主要用于苗后除草，使用剂量为：40~100克有效成分/公顷。若与禾本科杂草除草剂混用，可扩大杀草谱。
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；再经醚化、还原制成取代的苯胺；最后与四氢苯酐缩合即得目的
物。反应式为：
主要原料与中间体： 对氟苯酚、氯气、氯甲酸乙酯、氯乙酸戊酯、4,5,6,7-四氢苯酐
分析方法： HPLC
开发公司： 日本住友化学公司开发。
专利申请： EP 83055
在我国登记情况： 在我国大豆田已临时登记，登记号为：LS94027

flumiclorac-pentyl
Herbicide
HRAC E WSSA 14; N-phenylphthalimide

NOMENCLATURE
flumiclorac-pentyl
Common name flumiclorac-pentyl (BSI, pa ISO, ANSI)
IUPAC name pentyl [2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)-4-fluorophenoxy]acetate
Chemical Abstracts name pentyl [2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetate
CAS RN [87546-18-7] Development codes S-23031 (Sumitomo); V-23031 (Valent)

flumiclorac
Common name flumiclorac (BSI, pa E-ISO, ANSI)
IUPAC name [2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)-4-fluorophenoxy]acetic acid
Chemical Abstracts name [2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid
CAS RN [87547-04-4]

PHYSICAL CHEMISTRY
flumiclorac-pentyl
Mol. wt. 423.9 M.f. C21H23ClFNO5 Form Beige solid, with a halide odour. M.p. 88.9-90.1 ºC V.p. <0.01 mPa (22.4 ºC) KOW logP = 4.99 (20 ºC) S.g./density 1.33 g/ml (20 ºC) Solubility In water 0.189 mg/l (25 ºC). In methanol 47.8, hexane 3.28, n-octanol 16.0, acetone 590 (all in g/l). Stability Hydrolytic DT50 4.2 d (pH 5), 19 h (pH 7), 6 min (pH 9). Aqueous photolysis DT50 are similar. F.p. 68 ºC

flumiclorac
Mol. wt. 353.7 M.f. C16H13ClFNO5

COMMERCIALISATION
Patents US 4770695; EP 83055 Manufacturers Sumitomo

APPLICATIONS
flumiclorac-pentyl
Biochemistry Protoporphyrinogen oxidase inhibitor. It is suggested that flumiclorac-pentyl induces accumulation of porphyrins in susceptible plants. The photosensitising action of accumulated porphyrins is likely to be one of the causes of membrane lipid peroxidation, which in turn leads to irreversible damage of membrane function and structure in susceptible plants, and results in symptoms outlined below. Differences in metabolism of flumiclorac-pentyl seem to be the basis of crop selectivity. Experiments with 14C-flumiclorac-pentyl suggest more rapid degradation in soya beans than in Abutilon. Mode of action Fast-acting, contact post-emergence herbicide. When applied to foliage of susceptible plants, it is readily absorbed into plant tissue and causes characteristic herbicidal symptoms such as desiccation, wilting, bleaching, browning and necrosis. Uses Pre- and post-emergence herbicide for control of problem broad-leaved weeds, including Xanthium strumarium, Chenopodium album, Ambrosia artemisiifolia, Datura stramonium, Amaranthus spp., Sida spinosa, Euphorbia maculata, and Abutilon theophrasti, in soya beans and maize, at 0.027-0.054 lb/a. Formulation types EC. Selected products: 'Resource' (Sumitomo, Valent); 'Sumiverde' (Sumitomo)

OTHER PRODUCTS
flumiclorac-pentyl
Mixtures: 'Stellar' (+ lactofen) (Sumitomo, Valent)

MAMMALIAN TOXICOLOGY
flumiclorac-pentyl
Oral Acute oral LD50 for rats 3.69 kg 0.86EC/kg. Skin and eye Acute percutaneous LD50 for rabbits >2.0 g 0.86EC/kg. Moderately irritating to skin and eyes; not a skin sensitiser. Inhalation LC50 for rats 5.51 mg 0.86EC/l.

ECOTOXICOLOGY
flumiclorac-pentyl
Birds Acute oral LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 for rainbow trout 1.1, bluegill sunfish 13-21 mg/l. Daphnia LC50 (48 h) >38.0 mg/l. Bees LD50 (contact) >196 mg/bee.

ENVIRONMENTAL FATE
Plants In soya beans and maize, the major metabolite is 2-chloro-4-fluoro-5-(4-hydroxy-1,2-cyclohexanedicarboximido)phenoxyacetic acid formed by reduction of the tetrahydrophthaloyl double bond and hydroxylation; other metabolic pathways include cleavage of the ester, and cleavage of the imide linkage. Soil/Environment Rapidly degraded in soil: DT50 0.48-4.4 d in loamy-sand soil (pH 7); degradates have DT50 c. 2-30 d. The a.i. is immobile in soil; degradates have low to medium mobility. No residues of parent or degradates were observed below the upper 3 inches of soil.