Flupyrsulfuron-methyl-Na 氟啶嘧磺隆

用于禾谷类作物防除禾本科杂草及大多阔叶杂草。2011年3月6日到期。杜邦公司开发。2009年市场0.60亿美元。1997年上市。

氟啶嘧磺隆
中文通用名称： 氟啶嘧磺隆
英文通用名称： flupyrsulfuron-methyl-sodium （BSI,ISO）
化学名称：
2-(4,6-二甲氧嘧啶-2-基氨基羰基氨基磺酰基)-6-三氟甲基烟酸甲酯 单钠盐
methyl 2-(4,6-dimethoxypyrimidin-2-ylcarbamylsulfamoyl)-6-trifluoromethylnicoti-nate monosodium sault
CA主题索引名及CAS登录号：
methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylate monosodium sault
[144740-54-5]

化学结构类型： 磺酰脲类
理化性质：
纯品为具刺激性气味的白色粉状固体；熔点165-170℃；密度1.48；蒸气压为4.0×10-9Pa (20℃)；分配系数 LogP(20℃)＝0.96(pH 5)，0.10(pH 6)；溶解度(20℃，mg/l)：乙腈4332，丙酮3049，正己烷>1.0，乙酸乙酯490， 二氯甲烷600；水中溶解度(25℃，pH 5) 为63。在水中的稳定性：44天(pH 5)、12天(pH 7)、0.4天(pH 9)。pKa 4.9。
毒性：
大(小)鼠急性经口LD50：>5000mg/kg；兔急性经皮L D50：>2000mg/kg；大鼠急性吸入LC50(4小时)：>2.0mg/l。对兔眼睛和兔皮无刺激。野鸭和鹌鹑急性经口L D50：>2250mg/kg；鱼毒LC50(96小时，mg/l)：鲤鱼820，虹鳟 470。无致突变性
制剂： 水分散颗粒剂。氟啶嘧磺隆还可与噻磺隆、甲磺隆、三唑啉酮类除草剂F8426混用，以扩大除草谱。

作用机理： 氟啶嘧磺隆与其它磺酰脲类除草剂一样是乙酰乳酸合成酶(ALS)的抑制剂。通过杂草根和叶吸收，在植株体内传导，杂草即停止生长，而后枯死。
适宜作物： 禾谷类作物如小麦、大麦等。
安全性： 对禾谷类作物安全。对环境无不良影响。因其降解速度快，无论何时施用，对下茬作物都很安全。
防除对象： 部分重要的禾本科杂草和大多数的阔叶杂草如看麦娘等。
使用方法： 氟啶嘧磺隆具有广谱活性的苗后除草剂。使用剂量为10克有效成分/公顷。

氟啶嘧磺隆有杜邦公司发现，并于1995年英国布莱顿植保会议上报道的除草剂，其作用新颖，可用于秋、春季播种的谷物，选择性防除鼠尾看麦娘等，芽后用药，具有一定的持效作用。 　　
杜邦公司开发了许多氟啶嘧磺隆的复配产品，其配伍主要包括吡氟酰草胺、噻吩磺隆、甲磺隆。氟啶嘧磺隆的使用主要局限于欧盟和一些东欧市场。

flupyrsulfuron-methyl-sodium
Herbicide
HRAC B WSSA 2; sulfonylurea

NOMENCLATURE
Common name flupyrsulfuron-methyl-sodium (BSI, pa ISO, ANSI)
IUPAC name methyl 2-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-6-trifluoromethylnicotinate monosodium salt
Chemical Abstracts name methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylate monosodium salt
CAS RN [144740-54-5]; acid [150315-10-9] Development codes DPX-KE459 (DuPont); DPX-JE138 (DuPont); IN-KE459

PHYSICAL CHEMISTRY
Composition Tech. is >90.3 g/kg. Mol. wt. 487.3 M.f. C15H13F3N5NaO7S; (acid, C14H12F3N5O7S) Form White powder, with a pungent, astringent odour. M.p. 165-170 °C V.p. 1 ´ 10-6 mPa (20 °C) KOW logP = 0.96 (pH 5), 0.10 (pH 6) (both 20 °C) Henry 1 ´ 10-8 Pa m3 mol-1 (pH5, 20 °C) (calc.) S.g./density 1.55 (19.3 °C) Solubility In water 62.7 (pH 5), 603 (pH 6) (both mg/l, 20 °C). In dichloromethane 0.60, acetone 3.1, ethyl acetate 0.49, acetonitrile 4.3, hexane <0.001, methanol 5.0 (all in g/l, 20 °C). Stability DT50 44 d (pH 5), 12 d (pH 7), 0.42 d (pH 9) (20 °C). Stable in most organic solvents. pKa 4.9

COMMERCIALISATION
History Reported by S. R. Teaney et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1995, 1, 49). Manufacturers DuPont

APPLICATIONS
Biochemistry Affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS). Inhibition of ALS leads to the rapid cessation of cell division and subsequent growth processes in plants. Mode of action Post-emergence, selective herbicide acting primarily through foliar uptake with little or no soil activity Uses Selective herbicide, which controls grass (primarily) blackgrass (Alopecurus myosuroides) and broad-leaf weeds in cereals. Applied post-emergence at 10 g/ha. Formulation types WG. Selected products: 'Lexus' (DuPont)

OTHER PRODUCTS
'Balance' (DuPont); 'Ductis' (DuPont); 'Lexus Solo' (DuPont); 'Oklar' (DuPont) mixtures: 'Lexus Class' (+ carfentrazone-ethyl) (DuPont); 'Lexus Millenium' (+ thifensulfuron-methyl) (DuPont); 'Lexus XPE' (+ metsulfuron-methyl) (DuPont); 'Millenium' (+ thifensulfuron-methyl) (DuPont); 'Spéléo' (+ metsulfuron-methyl) (DuPont)

ANALYSIS
Product and residue analysis by hplc/ms/ms (Handbook of Residue Analytical Methods, pp 400-410).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not a skin or eye irritant (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5.8 mg/l. NOEL (90 d) for male rats 124 mg/kg daily; (2 y) for male rats 14.2 mg/kg daily; (1 y) for male dogs 146.3 mg/kg daily. ADI 0.035 mg/kg. Other Non-mutagenic (Ames test), not genotoxic. Toxicity class WHO (a.i.) U EC classification N; R50, R53

ECOTOXICOLOGY
Birds Oral LD50 for mallard ducks >2250 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for carp 820, rainbow trout 470 mg/l. Daphnia LC50 (48 h) 721 mg/l. Algae EC50 (120 h) for green algae 0.004 mg/l. Other aquatic spp. EC50 (14 d) for Lemna gibba 0.003 mg/l. Bees LD50 (contact) >25 mg/bee; (dietary) >30 mg/bee. Worms LC50 >1000 mg/kg.

ENVIRONMENTAL FATE
Low Kow suggests that bioaccumulation should not occur. Animals In rats, rapid adsorption, metabolism and elimination of the administered dose occurred, with 90% excreted in the faeces and urine within 96 hours. Plants Flupyrsulfuron-methyl is rapidly metabolised in plants, by nucleophilic substitution of the sulfonyl group by gluthathione or by the intramolecular ipso nitrogen on the sulfonylurea bridge. Soil/Environment Lab. DT50 (ave.) in aerobic soils is 14 d. Under field conditions, ave. DT50 and DT90 are 14 and 47 d. Degradation is faster in alkaline soils; in acid soils, hydrolysis of the sulfonylurea bridge occurs.