Flumioxazin 丙炔氟草胺

中文通用名称： 丙炔氟草胺
英文通用名称： flumioxazin （BSI,ISO,ANSI）
商品名称： Sumisoya(速收)
试验代号： S-53482
化学名称： N-(7-氟-3,4-二氢-3-氧-(2-丙炔基)-2H-1,4-苯并恶嗪-6-基)环己-1-烯-1,2-二羧酰亚胺
N-(7-fluoro-3,4-dihydro-3-oxo-(2-propynyl)-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide
CA主题索引名及CAS登录号：
2-(7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl)-4,5,67-tetrahydro-1H-isoindole-1,(2H)-dione
[103361-09-7]

化学结构类型： 酰亚胺类
理化性质： 纯品为黄棕色粉状固体；熔点201~204℃；密度1.5136(20℃)；蒸气压为3.2×10-2Pa
(22℃)。水中溶解度为17.8 g/l (25℃)；在正常条件下贮存稳定。

毒性： 大鼠急性经口LD50：>5000mg/kg；兔急性经皮LD50：>2000mg/kg； 本品对兔皮肤无刺激，对兔眼睛有中度刺激。大鼠急性吸入LC50(4小时)：>3930mg/l空气。鱼毒LC50(96小时，mg/l)：鳟鱼2.3，大翻车鱼>21。无致突变性、无致畸性。

制剂： 50％可湿性粉剂。
作用机理： 原卟啉原氧化酶抑制剂。用S-53481处理土壤表皮后，药剂被土壤粒子吸收，在土壤表面形成处理层，等到杂草发芽时，幼苗接触药剂处理层就枯死。茎叶处理时，在敏感杂草叶面作用迅速，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小时出现叶面枯斑症状。
适宜作物： 大豆、花生等
安全性： 对大豆和花生极安全。对后茬作物小麦、燕麦、大麦、高粱、玉米、向日葵等无不良影响。
防除对象： 主要用于防除一年生阔叶杂草和部分禾本科杂草如鸭跖草、藜属杂草、蓼属杂草、黄花稔、马齿苋、鼬瓣、马唐、牛筋草、狗尾草等。S-53482对杂草的防效取决于土壤湿度，干旱时严重影响除草效果。
使用方法： S-53482对大豆和花生具有选择性播后苗前、苗后广谱除草剂，使用剂量为：50~100克有效成分/公顷。在我国大豆播种后出苗前，施用4~6克有效成分/亩，即可有效的防除大多数杂草。若与其它除草剂(碱性除草剂除外)如乙草胺等混用，不仅可扩大杀草谱，还具有显著的增效作用。

合成方法： 以间二氯苯为起始原料，经硝化、氟化、醚化、加氢还原合环、再与氯丙炔反应制得中间体取代苯胺；最后与酸酐反应即得目的物。反应式为：

主要原料与中间体： 间二氯苯、羟基乙酸乙酯、氯丙炔、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。
在我国登记情况： 在我国大豆田已临时登记，登记号为：LS95004

flumioxazin
Herbicide
HRAC E WSSA 14; N-phenylphthalimide

NOMENCLATURE
Common name flumioxazin (BSI, draft ISO, ANSI)
IUPAC name N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide
Chemical Abstracts name 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
CAS RN [103361-09-7] Development codes S-53482 (Sumitomo); V-53482 (Valent)

PHYSICAL CHEMISTRY
Mol. wt. 354.3 M.f. C19H15FN2O4 Form Yellow-brown powder. M.p. 202-204 ºC V.p. 0.32 mPa (22 ºC) KOW logP = 2.55 (20 °C) S.g./density 1.5136 (20 ºC) Solubility In water 1.79 g/l (25 ºC). Soluble in common organic solvents. Stability Hydrolysis DT50 4.2 d (pH 5), 1 d (pH 7), 0.01 d (pH 9). Stable under normal storage conditions.

COMMERCIALISATION
History Reported by R. Yoshida et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1991, 1, 69). Introduced by Sumitomo. First registered in USA in 2001. Patents US 4640707; EP 170191 Manufacturers Sumitomo

APPLICATIONS
Biochemistry Protoporphyrinogen oxidase inhibitor. Acts, in the presence of light and oxygen, by inducing massive accumulation of porphyrins, and enhancing peroxidation of membrane lipids, which leads to irreversible damage of the membrane function and structure of susceptible plants. Mode of action Herbicide, absorbed by foliage and germinating seedlings. Uses Control of many annual broad-leaved weeds and some annual grasses pre- and post-emergence in soya beans, peanuts, orchards and other crops. Applied at 1-3 oz/a. Phytotoxicity Soya beans and peanuts are tolerant. Maize, wheat, barley and rice are moderately tolerant. Formulation types WG; WP. Selected products: 'Sumisoya' (Sumitomo)

OTHER PRODUCTS
'Pledge' (Sumitomo); 'Sumimax' (Sumitomo); 'Valor' (Valent) mixtures: 'Donjon' (+ diuron) (Sumitomo, Philagro); 'Groundboy' (+ glufosinate-ammonium) (Sumitomo)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin; mild eye irritant (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >3930 mg/m3 air. NOEL Chronic dietary NOAEL 2 mg/kg daily. Other Non-mutagenic in the Ames test, in vivo chromosomal aberration, and in vivo/vitro UDS. EC classification R61| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250 mg/kg. Dietary LC50 (5 d) for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for rainbow trout 2.3, bluegill sunfish >21, sheepshead minnow >4.7 mg/l. Daphnia EC50 (48 h) for Daphnia pulex 5.5 ppm. Other aquatic spp. LC50/EC50 (96 h) for easter oyster 2.4, mysid shrimp 0.23 ppm. Bees LD50 for honey bees >105 mg/bee.

ENVIRONMENTAL FATE
Soil/Environment DT50 for photolysis on soil 5.8 d, for aerobic soil metabolism 14.7 d,