Bensulfuron Methyl 苄嘧磺隆

苄嘧磺隆

英文通用名：bensulfuron methyl
商品名称:农得时(Londax)

化学性质：
纯品为白色无臭固体，m.p.185～188℃，蒸气压1.733×10-3Pa (20℃)。溶解度为：二氯甲烷11720mg/L，乙腈5380mg/L，二甲苯280mg/L，乙酸乙酯1660mg/L，丙酮1380mg/L,甲醇990mg/L, 己烷3.1mg/L，水1200mg/L。分配系数为4.1。在微碱性（pH=8）水溶液中稳定，在酸性溶液中缓慢分解。pH值5时半衰期11d，pH值7时为143d。原药略带浅黄色。 苄嘧磺隆结构式

毒性：
大鼠急性经口LD50为5000mg/kg，小鼠>10985mg/kg。家兔急性经皮LD50>2000mg/kg。对眼无刺激。大鼠慢性经口无作用剂量为750mg/kg。动物试验未见致畸、致癌、致突变作用。鲤鱼LC50>1000mg/L (48h)，野鸭急性经口LD50>2150mg/kg。

中毒症状：
对眼睛、皮肤和粘膜有刺激作用，不大量摄入没有全身中毒症状。

急救治疗：
根据中毒症状进行治疗，没有专门的解毒药。用水冲洗皮肤和粘膜。如果摄入，要催吐。

剂型：
10%可湿性粉剂。

特点：
是选择性内吸传导型除草剂。药剂在水中迅速扩散，经杂草根部和叶片吸收后转移到其它部位，阻碍支链氨基酸生物合成。敏感杂草生长机能受阻、幼嫩组织过早发黄，抑制叶部、根部生长。能有效防治稻田1年生及多年生阔叶杂草和莎草，能被杂草根、叶吸收并传到其他部位。对水稻安全，使用方法灵活。

适用范围:
适用于稻田防除1年生及多年生阔叶杂草和莎草，在作物芽后，杂草芽前及芽后施药，对鸭舌草、眼子菜、节节菜等及莎科杂草（牛毛草、异型莎草、水莎草等）效果良好。

使用方法：
1.水稻秧田和直播田 播种后至杂草2叶期以内均可施药。防除1年生阔叶杂草和沙草，每亩用10%可湿性粉剂20-30克，对水30公斤喷雾或混细潮土20公斤撒施。施药时保持水层3-5cm，持续3-4天。
2、水稻移栽田 移栽前后3周均可使用，但以插秧后5-7天施药为佳。每亩用10%可湿性粉剂20-30克，防除多年生杂草并兼除稗草，药量可提高到30-50克。保水层5cm施药，可对水喷雾，亦可混细土撒施，保持水层3-4天，自然落干。

注意事项：
1.苄嘧磺隆对2叶期以内杂草效果好，超过3叶效果差。
2、对稗草效果差，以稗草为主的秧田不宜使用。
3.喷雾器具使用结束后要冲洗干净。
4.施药时稻田内必须有水层3－5cm，使药剂均匀分布。施药后7天不排水、串水，以免降低药效。 5.该药用量少，必须称量准确。
6.视田间草情，适用于阔叶杂草和禾草优势地块和稗草少的地块。
最新进展：苄嘧磺隆（农得时、稻无草、便农）最先用于稻田防除莎草和阔叶杂草，目前已用于麦田防除阔叶杂草。苄嘧磺隆是选择性内吸传导型除草剂，被杂草根和叶片吸收转移到各部位而起作用，对小麦、水稻等作物安全性好。在麦田使用，能有效防除猪殃殃、繁缕、碎米荠、播娘蒿、荠菜、大巢菜、藜、稻槎菜等阔叶杂草，通常在杂草2-3叶期、土壤潮湿时每亩用10%苄嘧磺隆30-40克加水喷雾。该药有效成分在水中扩散迅速，温度、土质对除草效果影响小，在土壤中移动性小。它在水田使用效果良好，在麦田使用时土壤一定要潮湿，如果土壤干旱，防效较低。

生产工艺：
2-氨基-4，6-二甲氧基嘧啶的制备 用硝酸胍与丙二酸二乙酯在乙醇及乙醇钠中回流反应4h，得2-氨基-4，6-二羟基嘧啶，收率97%；然后将2-氨基-4，6-二羟基嘧啶经POCl3氯化、回流反应1.5h，达到终点后蒸出剩余的POCl3，加氨水调节pH值至7～8，以中和反应生成的偏磷酸和氯化氢，生成铵盐水洗除去，经过滤、干燥得2-氨基-4，6-二氯嘧啶，收率80%；上述产物与甲醇钠反应，回流反应6h，冷却过滤，蒸出甲醇，加适量水，析出固体，过滤干燥后得2-氨基-4，6-二甲氧基嘧啶，收率91%。
2-氨基-4，6-二甲氧基嘧啶也可采用下述合成路线制备：用尿素和丙二酸二乙酯在乙醇钠存在下，反应生成2，4，6-三羟基嘧啶，再用三氯化磷氯化，在氨基钠存在下胺化，最后再与甲醇钠反应制得。或用丙二腈与甲醇、氯化氢反应生成1，3-二甲氧基丙二亚胺双盐酸盐，再与定量甲醇钠控制反应并趋向重排生成单盐酸盐，再与氨基氰反应，经环化重排制得。邻甲酸甲酯苄基磺酰异氰酸酯的制备 先制取邻甲酸甲酯氯苄。用邻甲基苯甲酸经三氯化磷（或光气）酰氯化，生成邻甲基苯甲酰氯，再在引发剂BPO存在下用氯气氯化制得邻氯甲基苯甲酰氯，再经甲醇酯化制得。再制取邻甲酸甲酯苄基磺酸胺。用邻甲酸甲酯氯苄与硫脲在乙醇中回流反应1h，生成邻甲酸甲酯苄基硫甲脒盐酸盐；再于0～5℃通氯1h得邻甲酸甲酯苄基磺酰氯；在有机溶剂存在下，反应温度小于20℃通氨胺化，得邻甲酸甲酯苄基磺酰胺。最后制备邻甲酸甲酯苄基磺酰异氰酸酯。用邻甲酸甲酯苄基磺酰胺，在异氰酸正丁酯、有机碱（1，4-二氮杂二环-2，2，2-辛烷，或称DABCO)存在下，以二甲苯为溶剂，于120℃通入光气3h，蒸出二甲苯和异氰酸正丁酯，得邻甲酸甲酯苄基磺酰异氰酸酯。苄嘧磺隆的合成 用邻甲酸甲酯苄基磺酰异氰酸酯的二甲苯溶液与2-氨基-4，6-二甲氧基嘧啶在室温到搅拌反应8～10h，蒸出二甲苯，用氯丁烷洗涤并干燥，制得苄嘧磺隆。

bensulfuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea

NOMENCLATURE
bensulfuron-methyl
Common name bensulfuron-methyl
IUPAC name methyl a-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluate
Chemical Abstracts name methyl 2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]carbonyl]amino]sulfonyl]methyl]benzoate
CAS RN [83055-99-6] EEC no. 401-340-6 (ELINCS) Development codes DPX-F5384 (DuPont)

bensulfuron
Common name bensulfuron (BSI, ANSI, WSSA, draft E-ISO, (m) draft F-ISO)
IUPAC name a-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluic acid
Chemical Abstracts name 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid
CAS RN [99283-01-9]

PHYSICAL CHEMISTRY
bensulfuron-methyl
Composition Tech. is 97.5%. Mol. wt. 410.4 M.f. C16H18N4O7S Form White odourless solid. M.p. 185-188 ºC; tech. 179.4 °C V.p. 2.8 ´ 10-9 mPa (25 ºC) KOW logP = -0.99 (pH 5), 0.79 (pH 7), 2.18 (pH 9) (all 25 ºC) Henry 2 ´ 10-11 Pa m3 mol-1 (calc.) S.g./density 1.49 (20 °C) Solubility In water 2.1 (pH 5), 67 (pH 7), 3100 (pH 9) (all in mg/l, 25 ºC). In acetone 5.10, acetonitrile 3.75, dichloromethane 18.4, ethyl acetate 1.75, n-heptane 3.62 ´ 10-4, xylene: 0.229 (all in g/l, 20 ºC). Stability Aqueous solutions are most stable under slightly alkaline conditions (pH 8), and slowly degrade under acidic conditions; DT50 6 d (pH 4), stable (pH 7), 141 d (pH 9) (all 25 ºC). pKa 5.2

bensulfuron
Mol. wt. 396.4 M.f. C15H16N4O7S

COMMERCIALISATION
History Herbicidal activity of bensulfuron-methyl reported by T. Yayama et al. (Proc. 9th Asian Pacific Weed Sci. Soc. Congr., 1983, p. 554). Introduced by E. I. du Pont de Nemours and Co.; first approval in 1985. Patents US 4420325 Manufacturers DuPont; Sannong; Sharda; Shenyang; Sundat

APPLICATIONS
bensulfuron-methyl
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Selectivity is due to rapid metabolism in the crop. Metabolic basis of selectivity reviewed (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)). Mode of action Selective systemic herbicide, absorbed by the foliage and roots, with rapid translocation to the meristematic tissues. Uses Selective pre- and post-emergence control of annual and perennial weeds and sedges (e.g. Butomus umbellatus, Scirpus maritimus, Scirpus mucronatus, Alisma plantago-aquatica, Sparganium erectum, Cyperus spp., Typha spp., etc.) in flooded or wetland rice, at 46-60 g/ha. Formulation types WG; WP. Selected products: 'Londax' (DuPont); mixtures: 'Fujigrass' (+ esprocarb) (DuPont, Syngenta); 'Zark' (+ mefenacet) (DuPont, Kumiai, Nihon Bayer, Sankyo Agro); 'Innova GR 75' (+ fentrazamide) (Nihon Bayer); 'Kusamets' (+ thenylchlor) (Tokuyama, Hokko, Nihon Nohyaku); 'Kusastop' (+ indanofan) (Nihon Nohyaku); 'Patful' (+ oxaziclomefone+ pyriminobac-methyl) (Kumiai); 'Prosper' (+ mefenacet+ pyriminobac-methyl) (Kumiai); 'Topgun' (+ bromobutide+ pentoxazone+ pyriminobac-methyl) (Kumiai); 'Wolf-Ace' (+ mefenacet+ thiobencarb) (Kumiai)

OTHER PRODUCTS
bensulfuron-methyl
'Rozal' (DuPont); 'Escuri' (Crystal) mixtures: 'Kingdom' (+ pyributicarb+ thenylchlor) (DuPont); 'Kusanain' (+ dimethametryn+ pretilachlor+ pyributicarb) (DuPont); 'Sindax' (+ metsulfuron-methyl) (DuPont); 'Bazooka 36' (+ cyhalofop-butyl+ thenylchlor+ azimsulfuron) (Nihon Nohyaku); 'Bazooka A' (+ cyhalofop-butyl+ azimsulfuron) (Nihon Nohyaku, Hokko, Tokuyama, DuPont); 'Bazooka' (+ cyhalofop-butyl+ thenylchlor) (Nihon Nohyaku, Hokko, Tokuyama, DuPont); 'Cao Neng' (+ quinclorac) (Anhui); 'Dancing A' (+ indanofan+ azimsulfuron) (Nihon Nohyaku); 'Dancing L' (+ indanofan) (Nihon Nohyaku); 'Dancing-Power A' (+ clomeprop+ indanofan+ azimsulfuron) (Nihon Nohyaku); 'Dancing-Power L' (+ clomeprop+ indanofan) (Nihon Nohyaku); 'Dinaman' (+ clomeprop+ indanofan) (Nihon Nohyaku); 'Duet EDF' (+ propanil) (Riceco); 'Homerun' (+ oxaziclomefone) (Hokko); 'Inebrite' (+ fentrazamide+ azimsulfuron) (Bayer CropScience); 'Inegreen D' (+ cyhalofop-butyl+ daimuron+ mefenacet) (Nihon Bayer, Hokko); 'Inegreen' (+ cyhalofop-butyl+ mefenacet) (Nihon Bayer); 'Innova GR 51' (+ daimuron+ fentrazamide) (Nihon Bayer); 'Innova L SC' (+ daimuron+ fentrazamide) (Nihon Bayer); 'Innova SC' (+ fentrazamide) (Nihon Bayer); 'Joystar' (+ cafenstrole+ cyhalofop-butyl+ daimuron) (Kumiai); 'Joyster' (+ cafenstrole+ cyhalofop-butyl+ daimuron) (Kumiai); 'Karshot' (+ pyributicarb) (Sankyo Agro); 'Kusamets FL' (+ thenylchlor) (Nihon Nohyaku, Tokuyama, Hokko); 'Kusastop A' (+ indanofan+ azimsulfuron) (Nihon Nohyaku); 'Kusatory Ace Jumbo' (+ cafenstrole+ daimuron) (Sankyo Agro); 'Kusatory E Jumbo' (+ pyributicarb) (Sankyo Agro); 'Londanil' (+ propanil) (Crystal); 'Masakari A Jumbo' (+ clomeprop+ indanofan+ azimsulfuron) (Nihon Nohyaku); 'Masakari L Jumbo' (+ clomeprop+ indanofan) (Nihon Nohyaku); 'Non-Poong' (+ benfuresate) (Bayer CropScience); 'Papika A I Kilo' (+ cyhalofop-butyl+ thenylchlor+ azimsulfuron) (Nihon Nohyaku, Hokko, Tokuyama, Dow AgroSciences, DuPont); 'Papika A' (+ cyhalofop-butyl+ thenylchlor+ azimsulfuron) (Tokuyama, Nihon Nohyaku, Hokko, DuPont, Dow AgroSciences); 'Papika' (+ cyhalofop-butyl+ thenylchlor) (Tokuyama, Nihon Nohyaku, Hokko, DuPont, Dow AgroSciences); 'Pro-Pack 80EDF' (+ propanil) (Agriliance); 'Push' (+ dimepiperate) (Hokko, Bayer CropScience, DuPont); 'Rakudar' (+ cafenstrole+ daimuron) (Sankyo Agro); 'Ranger' (+ dimepiperate+ benfuresate) (Bayer CropScience, Hokko, DuPont); 'Step' (+ benzofenap+ thenylchlor) (Nihon Nohyaku); 'Weedless A36' (+ cafenstrole+ daimuron+ azimsulfuron) (Sankyo Agro, DuPont, Eiko Kasei, SDS Biotech KK); 'Weedless' (+ cafenstrole+ daimuron) (Sankyo Agro); 'Wydori A' (+ dimethametryn+ pretilachlor+ azimsulfuron) (Nihon Nohyaku); 'Zark D' (+ daimuron+ mefenacet) (Sankyo Agro) Discontinued products: 'Mariner' * (DuPont) mixtures: 'Kusatory Jumbo' * (+ daimuron+ pyributicarb) (Sankyo); 'Tabijin A' * (+ cyhalofop-butyl+ pretilachlor+ pyriminobac-methyl+ azimsulfuron) (Kumiai)

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

MAMMALIAN TOXICOLOGY
bensulfuron-methyl
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritant to skin and eyes. Not a skin sensitiser (Buehler method). Inhalation LC50 (4 h) for rats 5 mg/l air. NOEL (1 y) for male dogs 21.4 mg/kg b.w. daily; reproduction (2 generation) NOEL for male rats 20 mg/kg b.w. daily; teratogenicity NOEL for rabbits 300 mg/kg b.w. daily. No developmental toxicity or teratogenicity. ADI 0.20 mg/kg. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification R43| N; R51, R53

ECOTOXICOLOGY
bensulfuron-methyl
Birds Acute oral LD50 for mallard ducks >2510 mg/kg. Dietary LC50 (8 d) for bobwhite quail, mallard ducks >5620 mg/l. Fish LC50 (96 h) for rainbow trout >66, bluegill sunfish >120 mg/l. Daphnia LC50 (48 h) >130 mg/l. Algae EC50 (72 h) for Selenastrum capricornutum 0.020 mg/l. Other aquatic spp. EC50 (14 d) for Lemna gibba 0.0008 mg/l. Bees LD50 (oral) >25.7 mg/bee; (contact) >100 mg/bee. Worms LC50 >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals Almost completely biotransformed and rapidly excreted in urine and faeces of rats and goats. Plants After uptake by rice, converted to a non-herbicidal metabolite. Soil/Environment DT50 (ave.) 88.5 d on Flanagan and Keyport silt loam soils. DT50 in water 16-21 d for Italian soils.
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