Pyriminobac-methyl 嘧草醚

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嘧草醚

CAS:136191-64-5
英文名称:Pyriminobac-methyl
化学名称:2-[(4,6-二甲氧基嘧啶-2-基)氧]-6-[1-(N-甲氧基亚氨基)乙基]苯甲酸甲酯;methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate
其他名称:必利必能,KIH-6127
分子式:C17H19N3O6
分子量:361.4

理 化 性 质:原药含(E)-异构体 75-78%, (Z)-异构体 20-11%。外观为淡黄色晶粒,比重1.3428g/mL(20℃),熔点96-106℃,蒸气压2.138×10-4Pa(25℃),水中溶解度为0.00925g/l,甲醇中为14.6 g/l。在水中稳定。

毒性:大鼠经口 LD50 >5000 mg/kg,经皮LD50: >2000 mg/kg. 对兔皮肤和眼睛有轻微刺激。北美鹌鹑经口LD50 >2000 mg/kg.,野鸭LC50 (5 d) >5200 mg/kg ,鲤鱼LC50 (96 h) 30.9, 鲑鱼LC50 (96 h) 21.2 mg/l ,蜜蜂LD50 (24 h,) >200 μg/只。

作用特点及杀草谱:嘧草醚是日本组合化学新近研发的一种内吸传导型专业除稗剂,属嘧啶水杨酸类除草剂,它可以通过杂草的茎叶和根吸收,并迅速传导至全株,抑制乙酰乳酸合成酶(ALS)和氨基酸的生物合成,从而抑制和阻碍杂草体内的细胞分裂,使杂草停止生长,最终使杂草白化而枯死。

特点:
对水稻极为安全,即使在播种后0-3天也可使用;
能防除3叶期以前的稗草;
持效期长,在有水层的条件下,持效期可长达40-60天以上;
使用方便,毒土、毒肥或茎叶喷施均可;
能与绝大多数农药混用;
对人、畜以及鱼类的毒性很低,对水生物的毒性也很低。
施药后后杂草死亡速度比较慢,一般为7-10天,嘧草醚对未发芽的杂草种子和芽期杂草无效。
使用方法 :水稻移栽后,稗草3叶期前,嘧草醚20-30克/亩+苄嘧磺隆20克/亩(混用),毒土、毒肥或茎叶喷施。

生产方法:以3-羟基苯乙酮为起始原料,与苄基溴反应间苯氧基苯乙酮,再与原甲酸甲酯反应得到二甲基缩醛体,在环己烷中用丁基锂进行甲氧羰基化反应,再脱缩醛,得到6-乙酰基体,然后与甲氧胺硫酸盐反应,再用常法脱去苄基,最后与2-甲磺酰基-4,6-二甲氧基嘧啶反应得到嘧草醚。

生产情况:日本组合化学研究开发。国内未见生产报道。

其他:组合化学在我国申请了嘧草醚专利,专利号:CN1035325C(1990.12.28),即将到期

 

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pyriminobac-methyl
Herbicide
HRAC B WSSA 2; pyrimidinyloxybenzoic

  pyriminobac-methyl

NOMENCLATURE
Common name pyriminobac-methyl (BSI, pa ISO)
IUPAC name methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy)-6-(1-methoxyiminoethyl)benzoate
Chemical Abstracts name methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate
CAS RN [136191-64-5] methyl ester; [136191-56-5] acid Development codes KIH-6127; KUH-920 (both Kumiai)

PHYSICAL CHEMISTRY
Composition Tech. is >93%: (E)- isomer 75-78%, (Z)- isomer 20-11%. Mol. wt. 361.4 M.f. C17H19N3O6 Form White powder; (tech., pale yellow grains). M.p. Tech. 105 ºC; pure (E)- isomer 107-109 °C; pure (Z)- isomer 70 °C V.p. (E)- isomer 3.5 ´ 10-2 mPa (25 °C); (Z)- isomer 2.681 ´ 10-2 mPa (25 °C) KOW (E)- isomer, logP = 2.98 (21.5 °C); (Z)- isomer, logP = 2.70 (20.6 °C) S.g./density (E)- isomer 1.3868; (Z)- isomer 1.2734 (both 20 °C) Solubility (E)- isomer: in water 0.00925, methanol 14.6 (both in g/l, 20 ºC). (Z)- isomer: in water 0.175, methanol 14.0 (both in g/l, 20 ºC). Stability Stable in water (>1 y, pH 4-9), to light, and to heat (not decomposed after 14 d at 55 °C)

COMMERCIALISATION
History Reported by Kumiai Chemical Industry Co., Ltd (R. Hanai et al., Proc. Br. Crop Prot. Conf. - Weeds, 1993, 1, 47). Introduced by Kumiai in Japan in 1996. Patents US 5118339 Manufacturers Ihara/Kumiai

APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Mode of action Selective, systemic herbicide, absorbed by foliage. Uses Selective control of barnyardgrass (Echinochloa spp.) in paddy rice; applied early post-emergence, at 30-60 g/ha. Formulation types GR; WP. Selected products: mixtures: 'Patful' (+ bensulfuron-methyl+ oxaziclomefone) (Kumiai); 'Prosper' (+ bensulfuron-methyl+ mefenacet) (Kumiai); 'Topgun' (+ bensulfuron-methyl+ bromobutide+ pentoxazone) (Kumiai)

OTHER PRODUCTS
Discontinued products mixtures: 'Tabijin A' * (+ azimsulfuron+ bensulfuron-methyl+ cyhalofop-butyl+ pretilachlor) (Kumiai)

ANALYSIS
Product and residue analysis by glc. Details fromKumiai.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Slightly irritant to skin and eyes (rabbits). Inhalation LC50 (4 h, 14 d observation) for rats >5.5 mg/l air. NOEL (2 y) for male rats 0.9, female rats 1.2, male mice 8.1, female mice 9.3 mg/kg b.w. daily. ADI 0.009 mg/kg. Other Non-mutagenic in the Ames Test. Non-teratogenic (rats, rabbits). Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 (5 d) for bobwhite quail and mallard ducks >5200 mg/kg diet. Fish LC50 (96 h) for carp 30.9, rainbow trout 21.2 mg/l. Daphnia LC50 (24 h) for D. carinata >20 mg/l. Bees LD50 (24 h, oral and contact) >200 mg/bee. Worms NOEL (14 d) for Eisenia foetida >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals Almost all of dosed 14C was excreted in urine and faeces. Many metabolites were detected. Plants c. 10% of soil-applied 14C-pyriminobac-methyl (4-leaf stage, rice) was distributed throughout the plant; at harvest, residues were mostly in the straw. Soil/Environment Koc ((E)- isomer) 972, ((Z)- isomer) 499.