咪草烟,化学名为2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-5-乙基-3-吡啶羧酸。在酸性及中性条件下稳定,遇强碱分解。
基本信息
化学名:2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧代-1H-咪唑-2-基]-5-乙基-3-吡啶羧酸;
咪唑乙烟酸水剂;(RS)-5-乙基-2-(4-异丙基-4-甲基-5-氧代-2-咪唑啉-2-基)烟酸;3-吡啶羧酸-2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧-1H-咪唑-2-基]-5-乙基酯;普施特;灭草烟(普施特);豆草特水剂;咪草烟水剂;咪唑乙烟酸;(RS)-5-乙基-2-(4-异丙基-4-甲基-5-氧代-1H-咪唑啉-2-基)烟酸
英文别名:2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid; 5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid; (+-)-midazol-2-yl)-5-ethyl; 5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-2-((+-)-3-pyridinecarboxylicaci; 5-dihydro-4-methyl-4(1-methylethyl)-5-oxo-1h-imidazol-2yl)-5-ethyl-3-(+-)-2-(; ac263,499; (RS)-5-ETHYL-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)-NICOTINIC ACID; PURSUIT; PURSUIT DG; PURSUIT(R); Pursuit,2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid; (+/-)-2-[4,5-dihydro-4-methyl-4-(1-methyltheyl)-5-oxo-1Himidazol-2-yl]-5-ethyl-3-pyridinecarboxy acid; 5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-1H-imidazolin-2-yl)nicotinic acid
CAS号:81335-77-5
分子式:C15H19N3O3
分子量:289.33
理化性质
熔 点:169℃-173℃
蒸气压:0.013mpa(60℃)
溶解度(g/L,25℃): 水1.4;丙酮48.2;
三氯甲烷185;甲苯5;异丙醇17;甲醇105
Kow logP = 1.04 (pH 5), 1.49 (pH 7), 1.20 (pH 9) (all 25 ºC)
稳定性:在酸性及中性条件下稳定,遇强碱分解。
产品特点:
原药质量指标
项目标准值
外观:淡黄色至白色结晶固体,无可见外来杂质
含量 ≥98.0%
PH:3.0-5.0
加热减量 ≤1.0%
固体不溶物 ≤1.0%
毒性: 低毒,大鼠急性经口LD50>5 000mg/kg。
[COMMERCIALISATION]
History: Herbicide reported by T. Malefyt et al. (Abstr. 1984, Weed Sci. Soc. Mtg., Miami, p. 18, Abstract 49). Introduced by American Cyanamid Co (now BASF AG).
[APPLICATIONS ]
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Hence reduces levels of valine, leucine and isoleucine, leading to disruption of protein and DNA synthesis. Selectivity in soya benas and peanuts is attributed to rapid detoxification via hydroxylation and glycosylation (B. Tecle et al., Proc. 1997 Br. Crop Prot. Conf. - Weeds, 2, 605). Mode of Action Systemic herbicide, absorbed by the roots and foliage, with translocation in the xylem and phloem, and accumulation in the meristematic regions. Uses Control of many major annual and perennial grass and broad-leaved weeds in soya beans and other leguminous crops. Applied pre-plant incorporated, pre-emergence, or post-emergence. Phytoxicity Non-phytotoxic to soya beans and other leguminous crops, when used as directed. Formulation types SL. Selected tradenames: 'Hammer' (BASF); 'Overtop' (BASF, du Pont); 'Pivot' (BASF); 'Pursuit DG' (BASF); 'Pursuit' (BASF)
[OTHER TRADENAMES ]
'Wayup' (BASF); 'Vezir' (Herbitécnica); 'Vrilec' (Ipesa)
[MAMMALIAN TOXICOLOGY ]
Oral: Acute oral LD50 for male and female rats, and female mice >5000 mg/kg. Skin and eye: Acute percutaneous LD50 for rabbits >2000 mg/kg; mild skin and reversible eye irritant.
Inhalation: LC50 for rats 3.27 mg/l air (analytical), 4.21 mg/l (gravimetric).
NOEL (2 y): for rats >10 000 mg/kg diet; (1 y) for dogs >10 000 mg/kg diet (highest dose tested).
WHO hazard class: III (Table 5)
Other: Non-mutagenic in the Ames test.
Toxicity class: III
[ECOTOXICOLOGY ]
Birds: Acute oral LD50 for bobwhite quail and mallard ducks >2150 mg/kg.
Fish: LC50 (96 h) for bluegill sunfish 420, rainbow trout 340, channel catfish 240 mg/l.
Daphnia: LC50 (48 h) <1000 mg/l.
Algae: NOEL for Selenastrum capricornutum 50 mg/l. Other aquatic spp. I50 for Lemna gibba 4.38 mg/l.
Bees: Topical LD50 for honeybees >0.1 mg/bee.
Worms: I50 >10 000 mg/kg.
[ENVIRONMENTAL FATE ]
Animals: In rats, following oral administration, 92% was excreted in the urine and 5% in the faeces within 24 hours. Residue levels in blood, liver, kidney, muscle, and fat tissues were <0.01 ppm after 48 hours.
Plants: Rapidly metabolised in non-susceptible plants; half-life in soya beans 1.6 days. The primary metabolic route in maize is oxidative hydroxylation at the a-carbon atom of the ethyl substituent on the pyridine ring.
Soil/Environment: Half-life in soil 1-3 months.
用途
咪唑啉酮类除草剂,是侧链
氨基酸合成抑制剂,芽前或芽后施用。对大豆田和其他豆科植物田的
禾本科杂草和某些
阔叶杂草有优异的防效,如苋菜、蓼、藜、龙葵、苍耳、稗草、狗尾草、马唐、黍等。可制成水剂。 施药方法:苗期(大豆真叶期至2片复叶期、杂草1~4叶期),每公顷1000~2000ml5%水剂,对水450~600kg均匀喷雾。插后苗期(土壤墒情好时),每公顷1500~2250ml5%水剂,对水450~600kg均匀喷雾。 注意事项:施药均匀、周到,避免重复施药,一年内仅可施药一次;避免飞机高空施药;施药时切不可漂移至敏感作物上;敏感作物有甜菜、白菜、油菜、西瓜、黄瓜、马铃薯、茄子、辣椒、番茄、高粱等,上述作物在第二年内不能种植,甜菜三年内不能种植;本制剂适于东北大豆产区,未应用过的地区应在农技部门指导下试验后推广。
制备或来源
双乙烯酮在
二氯甲烷中用氯气处理,得氯代乙酰乙酸乙酯,该化合物与二氯砜在三氯甲烷中,于室温下反应10小时,得2,4-二氯代乙酰乙酸乙酯,再与2-乙基丙烯醛和氨基磺酸铵在无水乙醇中回流1.5小时,制得2-氯甲基-5-乙基烟酸乙酯,后者与2-氨基-2,3-二甲基丁酰胺和碳酸氢钠在二甲基亚砜中,于80℃下反应16小时,得到的缩合物再水解,然后在乙酸中环合即得咪草烟。
备注:勿在未衬里的不锈钢或铝容器中贮存或混合,有腐蚀性;不能与强氧化剂混合。避免药物接触皮肤、眼睛或玷污衣物;避免吸入液雾。药剂一旦接触皮肤、眼睛应用大量清水冲洗;不慎误服时,勿催吐应立即送医院诊治。
生态毒理学
鸟类:急性经口LD50,鹌鹑和绿头鸭2150毫克/千克。
鱼类:半致死浓度( 96小时)为420毫克/升,虹鳟鱼340毫克/升,鲶鱼240毫克/升
蚤:半致死浓度( 48小时) 1000毫克/升
海藻:月牙藻50毫克/升,其他水生草浮萍为4.38毫克/升
蜜蜂:局部蜜蜂的LD50为0.1毫克/升。
虫类: 150~10 000毫克/升。
环境转移
动物:在大鼠口服后92 %从尿液排出,5 %从粪便排出,24小时内,血液,肝脏,肾脏,肌肉,脂肪组织的残留水平较多。
植物:快速新陈代谢的非敏感植物;半衰期大豆一点六天,主要代谢途径是在玉米氧化羟化在一个碳原子的乙基取代的吡啶环。
土壤/环境:半衰期在土壤中1-3个月。
包装及贮运
本品在贮存、运输和施药过程中切勿污染食物和饲料。