Flumetsulam 唑嘧磺草胺

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中文通用名称: 唑嘧磺草胺
英文通用名称: flumetsulam (BSI,ISO,ANSI)
商品名称: Broadstrike(阔草清)
试验代号: DE-498、XRD-498

化学名称: 2’ ,6 ’ -二氟- 5 -甲基[1,2,4]三唑并[1,5-a]嘧啶- 2 -磺酰苯胺
2',6'-difluoro-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonanilide

CA主题索引名及CAS登录号:
N-(2,6-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
[98967-40-9]

化学结构类型: 三唑并嘧啶磺酰胺类
理化性质: 纯品为灰白色、无味固体;熔点251~253℃;密度1.77(21℃);蒸气压为1.6×10-10Pa(25℃)。分配系数 LogP=-0.68;水中溶解度为49mg/l (pH 2.5)。
毒性: 大鼠急性经口LD50:>5000mg/kg;兔急性经皮LD50:>2000mg/kg; 本品对兔眼睛有轻微刺激,对兔皮肤无刺激。大鼠急性吸入LC50(4小时):>1.2mg/l。鹌鹑急性经口LD50:>2250mg/kg;野鸭LC50:>5620mg/kg; 对大翻车鱼、水蚤等无毒。Ames试验呈阴性。

制剂: 80%水分散颗粒剂。
作用机理: 唑嘧磺草胺是一种典型的乙酰乳酸合成酶(ALS)的抑制剂。由于其严重的抑制作用,是植物体内支链氨基酸──亮氨酸、缬氨酸与异亮氨酸生物合成停止,蛋白质合成受阻,生长停滞,最终死亡。
适宜作物: 大豆、玉米、小麦、大麦、豌豆、苜蓿等
安全性: 对大豆、玉米、小麦、大麦、豌豆、苜蓿、三叶草等安全;对大豆、玉米和小麦高度安全。尽管其残效期较长,但对后茬作物如大豆、玉米、小麦、大麦、豌豆、高粱、水稻、烟草、马铃薯、向日葵、苜蓿、三叶草等无不良影响,对油菜、甜菜、棉花及蔬菜等则非常敏感。
防除对象:
唑嘧磺草胺是一种广谱性除草剂,能防除大多数一年生与多年生阔叶杂草,对幼龄禾本科杂草也有抑制作用,如对苘麻、藜、繁缕、刺花花稔、猪殃殃、曼陀螺、反枝
苋、香甘菊、野萝卜等活性优异,对蓼、地肤、龙葵、野芝麻、婆婆纳、野西瓜苗、苍耳以及风华菜、遏蓝菜等多种十字花科杂草有显著的防效,对狗尾草、铁荸荠也有良好的活性。

使用方法:
大豆 播种前、播种后出苗前以及出苗后,土壤处理或茎叶处理即喷雾均可。播种前使用剂量为48~60克有效成分/公顷;播种后出苗前使用剂量为30~48克有效成分/公顷;出苗后使用剂量为20~25克有效成分/公顷。
玉米 播种后出苗前使用剂量为30~48克有效成分/公顷;茎叶处理剂量为20~30克有效成分/公顷。
小麦与大麦 三叶期至分蘖末期茎叶喷雾,剂量为18~24克有效成分/公顷。
豌豆 2~6节期茎叶喷雾,剂量为25克有效成分/公顷。
苜蓿与三叶草 2~3片复叶喷雾,剂量为25克有效成分/公顷。

合成方法
唑嘧磺草胺的合成方法主要有两种:
方法1:以巯基三唑为起始原料,酰胺化、氯磺化,再与2,6-二氟苯胺反应,在氢氧化钠水溶液中去保护,最后与3,3-二甲氧基丁酮-2合环即得目的物。反应式如下:

方法2:以巯基三唑为起始原料,首先与3,3-二甲氧基丁酮-2反应,再经氯磺化,最后与2,6-二氟苯胺反应,处理得目的物。反应式如下:


主要原料与中间体: 5-氨基-3-巯基-1,2,4-三唑(合成方法见参考文献4)、2,6-二氟苯胺(由2,6-二氟苯甲酰胺制备)
分析方法: HPLC
开发公司: 美国陶氏农业科学(Dow Agroscience)公司。
在我国登记情况: 已在我国进行了登记,用于麦田防除阔叶杂草。已得到中国中国石油和化学工业局授予行政保护,授权号:N B-US96010305。

 

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flumetsulam
Herbicide
HRAC B WSSA 2; triazolopyrimidine

  Flumetsulam

NOMENCLATURE
Common name flumetsulam (BSI, pa E-ISO, ANSI)
IUPAC name 2',6'-difluoro-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonanilide
Chemical Abstracts name N-(2,6-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
CAS RN [98967-40-9] Development codes DE-498; XRD-498 (both Dow)

PHYSICAL CHEMISTRY
Mol. wt. 325.3 M.f. C12H9F2N5O2S Form Off-white, odourless solid. M.p. 251-253 ºC V.p. 3.7 ´ 10-7 mPa (25 ºC) KOW logP = -0.68 (25 ºC, unstated pH) S.g./density 1.77 (21 ºC) Solubility In water 49 mg/l (pH 2.5); solubility increases with pH. Very slightly soluble in acetone and methanol. Insoluble in hexane and xylene. Stability Aqueous photolysis DT50 6-12 mo. Soil photolysis DT50 3 mo. pKa 4.6 F.p. >93 °C

COMMERCIALISATION
Manufacturers Dow AgroSciences

APPLICATIONS
Biochemistry Branched chain amino acid (leucine, isoleucine and valine) synthesis (ALS or AHAS) inhibitor. Selectivity in soya beans is due to rapid metabolic deactivation. Mode of action Systemic herbicide, absorbed by roots and leaves of plants and translocated to growth points. Uses Used alone, at 25-78 g/ha, and in combination with trifluralin or metolachlor for control of broad-leaved weeds and grasses in soya beans, field peas and maize. Phytotoxicity Crops damaged by soil application of flumetsulam include sugar beet, cotton, oilseed rape, grain sorghum, tomatoes, and sunflowers. Formulation types OF; SC; WG. Selected products: 'Broadstrike' (Dow AgroSciences)

OTHER PRODUCTS
'Preside' (Dow AgroSciences); 'Python' (Dow AgroSciences); 'Scorpion' (Dow AgroSciences) mixtures: 'Broadstrike Plus' (+ clopyralid) (Dow AgroSciences); 'Frontrow' (+ cloransulam-methyl) (Dow AgroSciences); 'Hornet' (+ clopyralid) (clopyralid as potassium salt) (Dow AgroSciences); 'Striker' (+ clopyralid) (clopyralid as potassium salt) (Dow AgroSciences); 'Accent Gold' (+ nicosulfuron+ rimsulfuron+ clopyralid) (DuPont); 'Bicep Magnum TR' (+ S-metolachlor+ atrazine) (Syngenta) Discontinued products mixtures: 'Broadstrike Post' * (+ 2,4-D+ clopyralid) (Dow AgroSciences); 'Scorpion III' * (+ 2,4-D+ clopyralid) (Dow AgroSciences); 'Broadstrike Dual' * (+ metolachlor) (Syngenta)

ANALYSIS
By glc with mass selection detection.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Slightly irritating to eyes (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats 1.2 mg/l. NOEL for mice >1000, female rats 500, male rats 1000, dogs 1000 mg/kg b.w. Other Non-teratogenic (dietary) in rats. Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250 mg/l. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >5620 mg/l. Fish LC50 (96 h) for silverside minnow >379 mg/l. Non-toxic to fathead minnow and bluegill sunfish. Daphnia Non-toxic. Algae EC50 (5 d) for green algae (Selenastrum capricornutum) 4.9 mg/l, bluegreen algae (Anabaena flos-aquae) 167 mg/l. Other aquatic spp. LC50 for shrimp >349 mg/l. Bees LC50 >100 mg/bee. NOEL 36 mg/bee. Worms LC50 (14 d) >950 mg/kg soil.

ENVIRONMENTAL FATE
Animals Rapidly cleared via urine and faeces with no metabolites in most mammals. 5-Hydroxy metabolite found in kidney tissue in the hen. Plants DT50 in maize 2 h, soya beans 18 h, Chenopodium 131 h. Metabolites depend on the species; 5-hydroxy or 5-methoxy derivatives are common. Soil/Environment Availability of flumetsulam in soil is principally dependent upon soil pH and organic matter. Herbicidal activity increases as pH increases and organic matter decreases. DT50 in soil (25 ºC, pH ³7, o.m. content <4%; or pH 6-7, o.m. content c. 1%) £1 mo. DT50 in soil (pH 6-7, o.m. content 2-4%) 1-2 mo. Koc 5 - 182; Kd 0.05 - 2.4.