Mesotrione 甲基磺草酮 硝磺草酮

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甲基磺草酮

甲基磺草酮又名米斯通,硝磺草酮,甲基磺草酮会使植物分生组织在3-5天后,出现黄化症状随之引起枯斑,继而整株植物死亡。适用于玉米地杂草的清除,本品的特点是对环境无影响,降雨不影响其药效,对玉米无不良影响。

甲基磺草酮
中文通用名:甲基磺草酮
CAS号:104206-82-8
其他中文名:米斯通
其他中文通用名:硝磺草酮(瑞士先正达作物保护有限公司 国内登记名称)
中文商品名:千层红(瑞士先正达作物保护有限公司)
分子式: C14H13NO7S
分子量:339.3205
结构式:

物理性质:原药为浅黄色晶状粉,熔点165℃,密度1.46g/ml(20℃),蒸气压4.27 ×10-8mmHg (20℃)。溶于二氯甲烷、乙腈与丙酮,它是一种弱酸,pKa3.12(20 ℃),由于其弱酸性,故离子化程度因pH 而异,水溶度系pH 依赖型,从20 ℃时2.2g/L(pH4.8)、15g/L(pH6.9)至22g/L(pH9.0),pH4~9时抗水解。
行政保护期:授权号 :NB—US200502 有效期 :七年零六个月 2012.8过期
1、适用作物:玉米
2、防治对象:一年生阔叶杂草+部分禾本科杂草 (对阔叶防效优于禾本科)

作用机理
抑制对-羟基丙酮酸双加氧酶(HPPD)的活性,HPPD可将氨基酸络氨酸转化为质体醌。质体醌是八氢番茄红素去饱和酶的辅助因子。是类胡萝卜素生物合成的关键酶。使用甲基磺草酮3-5天内植物分生组织出现黄化症状随之引起枯斑,两星期后遍及整株植物。具有弱酸性,在大多数酸性土壤中,能紧紧吸附在有机物质上;在中性或碱性土壤中,以不易被吸收的阴离子形式存在。温度高,有利于甲基磺草酮药效发挥;施药后1 h降雨,对甲基磺草酮药效无影响.

药品特点
对环境友好
本品能快速广泛地降解,并且最终代谢产物为二氧化碳,土壤中的半衰期平均值为9天,具有在土壤中快速降解,以及用量低等特点。
温度对甲基磺草酮的除草活性影响很大(禾本科稗草)
在 0℃条件下,150g/hm甲基磺草酮对稗草基本无效;25℃条件下,对稗草防效为40%,表现为叶片白化,但继续生长;35℃条件下,对稗草有良好的防效,稗叶片白化、萎蔫、逐步坏死。

降雨影响不大
在施药后不同时间模拟降雨,结果发现在处理后 0.5h内降雨,对甲基磺草酮的除草效果有明显影响,施药后 1h降雨,对甲基磺草酮的除草效果仍无影响。说明甲基磺草酮耐雨水冲刷的能力较强或杂草对甲基磺草酮的吸收作用较快。

对玉米安全性
甲基磺草酮土壤处理或茎叶处理对玉米的选择数大于4(由生物活性和安全性实验结果可知 甲基磺草酮对各玉米品种ED10≥600或800g/h,对杂草的ED90为100~150g/hm),说明其对玉米的安全性好。高剂量下处理,对玉米的药害症状表现为叶部白化现象,因不同类型玉米的敏感性不同,叶片白化的程度也有所不同,以甜玉米和爆裂玉米较敏感。
甲基磺草酮在正常使用剂量下,对玉米安全。国外研究结果表明,玉米对甲基磺草酮的抗性是因为玉米对药剂的吸收速度缓慢;单子叶植物如小麦体内HPPD酶对甲基磺草酮的敏感性比阔叶杂草低数百倍;玉米能快速的将甲基磺草酮降解为无活性的化合物,特别是通过P450催化的4-羟基化作用 。

使用方法
(1)甲基磺草酮土壤处理
在150g/hm时,对大部分供试阔叶杂草防效达90%,对禾本科杂草防效80%以上。甲基磺草酮的生物活性约为同类药剂磺草酮的2倍。
(2)甲基磺草酮茎叶处理
在100g/hm时,对阔叶杂草的防效可达90%,对禾本科杂草的防效达70%。甲基磺草酮茎叶处理的生物活性约为同类药剂磺草酮的3倍。
(3甲基磺草酮混配莠去津
弥补增效甲基磺草酮对禾本科杂草的药效,加入莠去津后能明显提高对禾本科杂草的防效,降低甲基磺草酮用量。

 

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mesotrione
Herbicide
HRAC F2 WSSA 28; triketone

  mesotrione

NOMENCLATURE
Common name mesotrione (BSI, pa ISO)
IUPAC name 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione
Chemical Abstracts name 2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione
CAS RN [104206-82-8] Development codes ZA 1296 (Zeneca)

PHYSICAL CHEMISTRY
Mol. wt. 339.3 M.f. C14H13NO7S M.p. 165 °C V.p. 5.69 ´ 10-3 mPa (20 °C). Henry <5.1 ´ 10-7 Pa m3 mol-1 (calc.) Solubility In water 2.2 (pH 4.8), 15 (pH 6.9), 22 (pH 9) (all in g/l, 20 °C). Stability Stable to hydrolysis (pH 4 - 9). pKa 3.12

COMMERCIALISATION
History Reported by R. A. Wichert et al., Proc. Br. Crop Prot. Conf. - Weeds, 1999, 1, 105. See also J. Dyson et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 2, 6A-021. Developed by Syngenta AG and first registered in 2001. Manufacturers Syngenta

APPLICATIONS
Biochemistry p-Hydroxyphenyl pyruvate dioxygenase inhibitor, which ultimately affects carotenoid biosynthesis. Selectivity in maize derives from differential metabolism (to the 4-hydroxy derivative) and also possibly from slower foliar uptake. Mode of action Uptake is foliar and via the root, with both acropetal and basipetal translocation. Symptoms are whitening of leaves, followed by necrosis of the meristematic tissue. Uses Under development for pre- (at 100-225 g/ha) and post- (at 70-150 g/ha) emergence control of broad-leaved weeds, such as Xanthium strumarium, Ambrosia trifida, Abutilon theophrasti, and Chenopodium, Amaranthus and Polygonum spp., and some grass weeds, in maize. Formulation types SC. Selected products: mixtures: 'Callisto' (+ atrazine) (Syngenta); 'Camix' (+ S-metolachlor+ benoxacor) (Syngenta); 'Lumax' (+ S-metolachlor+ benoxacor) (Syngenta)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Practically non-irritant to skin, mild irritant to eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male and female rats >5 mg/l. ADI 0.01 mg/kg b.w. (proposed)

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000, mallard ducks >5200 mg/kg. Fish LC50 (96 h) for bluegill sunfish and rainbow trout >120 mg/l. Daphnia L(E)C50 (48 h, static) 900 mg/l. Algae L(E)C50 (72 h, static) for Selenastrum capricornutum 4.5 mg/l. Worms NOEL ³1000 mg/kg.

ENVIRONMENTAL FATE
Key metabolites in animals, plants and soil include MNBA [4-(methylsulfonyl)-2-nitrobenzoic acid] and AMBA [2-amino-4-(methylsulfonyl)benzoic acid] Soil/Environment Stable to hydrolysis under sterile conditions at pH 5-9, with <10% degradation after 30 d (25 °C). Aqueous photolysis DT50 (sterile) 84 d. Soil adsorption is significantly influenced by pH and % o.c; Koc 387 (soil pH 4.6) to 19 (pH 7.7); Kd is linear with % o.c and ranges from 1-5. Degradation is influenced by soil pH; DT50 31.5 d (pH 5.0, % o.c. 2.0) to 4.0 d (pH 7.7, % o.c. 0.9). Environmental fate may be determined by soil pH and half-life as the only important parameters. See R. A. Wichert et al., Proc. Br. Crop Prot. Conf. - Weeds, 1999, 1, 105; and J. Dyson et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 2, 6A-021.