Imazapic Imazameth 甲基咪草烟

甲基咪草烟

CAS号：104098-48-8
英文名称：Imazameth
化学名称：(RS)-2-(4-异丙基-4-甲基-5-氧-2-咪唑啉-2-基)-5-甲基烟酸; ;(+/-)-2-(4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-methyl-3-pyridinecarboxylic acid
其他名称：甲咪唑烟酸，百垄通、高原
分子式：C14H17N3O3
分子量：275.

理化性质：熔 点：204℃-206℃ 蒸气压：<1×10-2mpa(25℃) 溶解度(g/L，25℃): 水 2.15; 丙酮18.9mg/mL 稳定性：在酸性及中性条件下稳定，遇碱分解。

毒性：大鼠急性经口LD50>5000mg/kg。兔急性经皮LD50>2000mg/kg。大鼠急性吸入LD50（4h）>4.83mg/L。对兔眼睛有中度刺激性,对兔皮肤无刺激性。无致畸、致突变。NOEL数据：大鼠(90a)喂养无作用剂量为1625mg/kg.d。ADI值：0.50mg/kg。山齿鹑和野鸭饲急性经口LD50>2150mg/kg。大翻车鱼、虹鳟LC50(96h)>100mg/L。蜜蜂LD50(接触)>100μg /只。

作用特点及杀草谱：乙酰乳酸合成酶(ALS)或乙酸羟酸合成酶（AHAs）的抑制剂，即通过抑制植物的乙酰乳酸合成酶，阻止支链氨基酸如缬氨酸、亮氨酸、异亮氨酸的生物合成，从而破坏蛋白质的合成，干扰DNA合成及细胞分裂与生长，最终造成植株死亡。杂草药害症状为：禾本科杂草在吸收药剂后8小时即停止生长，1～3天后生长点及节间分生组织变黄，变褐坏死心叶变黄紫色枯死。

应用：甲基咪草烟主要用于花生田早期苗后除草，对莎草科杂草、稷属杂草、草决明、播娘蒿等具有很好的活性。推荐使用剂量为：50～70g (a.i.)/hm2[亩用量为3.3～4.67g(a.i.)]。在我国推荐使用剂量为72～108g (a.i.)/hm2[亩用量为4.8～7.2g(a.i.)]

剂型：24%水剂 ；10％可溶性液剂

生产情况：山东先达化工有限公司，南通嘉禾化工有限公司，沈阳同祥农化有限公司., 金坛希望化工有限公司

imazapic
Herbicide
HRAC B WSSA 2; imidazolinone

NOMENCLATURE
Common name imazapic (BSI, pa ISO)
IUPAC name (RS)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid
Chemical Abstracts name (?-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid
Other names imazameth* (rejected BSI name proposal) CAS RN [104098-48-8] acid, unstated stereochemistry (formerly [81334-60-3]); [104098-49-9] ammonium salt, unstated stereochemistry Development codes AC 263 222; CL 263 222 (both Cyanamid)

PHYSICAL CHEMISTRY
Mol. wt. 275.3 M.f. C14H17N3O3 Form Off-white to tan powder. M.p. 204-206 ºC V.p. <1 ´ 10-2 mPa (60 ºC) KOW logP = 0.393 (pH 4, 5, 6 buffer, 25 ºC) Solubility In deionised water 2150 ppm (25 ºC). In acetone 18.9 mg/ml (25 °C). pKa pKa1 2.0, pKa2 3.6, pKa3 11.1

COMMERCIALISATION
History Reported by M. Wixson et al. (Proc. South. Weed Sci. Soc., 45, 341 (1992)). Introduced by American Cyanamid Co. (now BASF AG) in 1996. Manufacturers BASF

APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Selectivity in peanuts is attributed to rapid detoxification via hydroxylation and glycosylation (B. Tecle et al., Proc. 1997 Br. Crop Prot. Conf. - Weeds, 2, 605); lack of selectivity in soya beans explained (idem, ibid.). Mode of action Systemic, contact and residual herbicide. Weeds stop growing within 8 h of application, and begin to turn yellow 1-3 d later. Uses For post- and pre- emergence residual control of a wide range of annual and perennial weeds in pasture, rangeland and noncropland areas, at rates up to 0.188 lb/a. Formulation types WG; SL. Selected products: 'Cadre' (BASF); 'Plateau' (BASF)

OTHER PRODUCTS
'Flame' (BASF); 'Oraban' (BASF) mixtures: 'Midas' (+ imazapyr+ MCPA-2-ethylhexyl) (BASF); 'Oasis' (+ 2,4-D-2-ethylhexyl) (BASF); 'OnDuty' (+ imazapyr) (BASF)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Moderately irritating to eyes; slightly irritating to skin (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 for rats 4.83 mg/l air. NOEL (90 d) for rats 20 000 ppm (1625 mg/kg daily). Dermal NOEL (21 d) for rabbits 1000 mg/kg. Teratogenicity NOEL (maternal) for rats 1000, rabbits 350 mg/kg daily; (foetal) for rats 1000, rabbits 500 mg/kg daily. ADI 0.50 mg/kg. Other Non-mutagenic, non-genotoxic, non-carcinogenic, non-teratogenic. Toxicity class EPA (formulation) III (70 WG); IV (2 SL)

ECOTOXICOLOGY
Birds Oral LD50 for mallard ducks and bobwhite quail >2150 mg/kg. LC50 (8 d) for mallard ducks and bobwhite quail >5000 ppm. Fish LC50 (96 h) for channel catfish, rainbow trout and bluegill sunfish >100 mg/l. Daphnia LC50 (48 h) >100 mg/l. Algae EC50 (120 h) for Selenastrum >51.7 mg/l, for Anabaena >49.9 mg/l, for Skeletonema >44.1 mg/l, for Navicula >46.4 mg/l. Bees LD50 (contact) >100 mg/bee.

ENVIRONMENTAL FATE
Animals Does not bioaccumulate in animals; if ingested then rapidly excreted through urine and faeces. Soil/Environment The primary route of degradation in soil is via microbial activity; DT50 31-410 d, depending upon soil and climatic conditions. Aqueous DT50 <8 h; imazapic is degraded by aqueous photolysis in the presence of sunlight.