Clodinafop-propargyl 炔草酸

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炔草酸

【中文名称】 炔草酸
【其他中文名称】
【英文名称】 clodinafop-propargyl
【其他英文名称】
【农药类别】 除草剂
【作用方式】
【CA登记号】 105512-06-9
【化学类别】 苯醚类
【化学名称】 R-2-[4-(5-氯-3-氟-2-氧基吡啶)-苯氧基]-丙炔酸
【分析方法】 气相色谱法
【分子式】 C17H13ClFNO4
【结构式】

【理化性状】
外观为浅褐色粉末。比重(20℃,纯品)1.37g/cm3;熔点48.2-57.1℃;蒸气压(25℃)3.19×10-6Pa;溶解度水中(25℃,纯品)4.0mg/l;有机溶剂中(25℃)丙酮>500g/l、甲醇180g/l、甲苯>500g/l、正己烷7.5g/l、辛醇21g/l。

【毒性】
中毒症状:
急救治疗:
注意事项:
每日允许摄入量:0.004mg/kgB.W./day
急性经口LD50:>2000mg/kg
急性经皮LD50:>2000mg/kg

应用: 主要用于防除野燕麦、看麦娘、燕麦、黑麦草、普通早熟禾、狗尾草等

制剂:先正达-麦极(15%炔草酸可湿性粉剂)
1、炔草酸的作用方式及作用机理  
炔草酸(英文名 Clodinafop-propargyl )是瑞士先正达作物保护有限公司开发的苯氧羧酸类手性含氟高效低毒除草剂,对恶性禾本科杂草特别有效,与安全剂以一定比例混合,用于禾谷类作物,对禾本科杂草如鼠尾草、看麦娘、野燕麦、黑麦草、早熟禾、狗尾草等有优异的防效。作用方式:内吸性苗后广谱禾本科杂草茎叶除草剂。作用机理:炔草酯的作用机理为抑制植物体内乙酰辅酶A羧化酶的活性,为内吸传导性除草剂,由植物体的叶片和叶鞘吸收,韧皮部传导,积累于植物体的分生组织内,抑制乙酰辅酶A羧化酶,使脂肪酸合成停止,细胞的生长分裂不能正常进行,膜系统等含脂结构破坏,最后导致植物死亡。

2、炔草酸的药剂安全性
炔草酸在土壤中能迅速降解,在土壤中基本无活性,对后茬作物无影响。使用60克有效成分/公顷茎叶喷雾可造成小麦叶片黄化,但20天后可以恢复。在推荐的使用剂量范围内对小麦安全。对不同品种小麦的敏感性试验表明,小麦各品种间的敏感性未见明显差异。
制剂类型:15%炔草酸可湿性粉剂。
防治对象:炔草酸为小麦田禾本科杂草高效、稳定的苗后茎叶处理剂。被一些国家认为是防治看麦娘、野燕麦的首选产品,对其他恶性禾本科杂草(稗草、黑麦草等)也具有很好的防效,但对雀麦的防效不理想。

3、炔草酸的科学使用方法
(1)冬前防治麦田禾本科杂草。冬前在禾本科杂草2~4叶期,每667平方米(1亩)用15%炔草酸可湿性粉剂16克,对水30千克喷雾。(2)春后防治麦田禾本科杂草。春后禾本科杂草5~8叶期,每667平方米(1亩)用15%炔草酸可湿性粉剂24克,对水30千克喷雾,其田间综合防效要优于6.9%的彪马常规剂量。另外,炔草酸可同阔叶草除草剂混配,并且防效较高。但混配时一定要掌握炔草酸的用量,15%炔草酸240 克/公顷与10%苯磺隆150克/公顷或异丙隆1500克/公顷混配,可有效防除麦田禾本科及阔叶草害。

 

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clodinafop-propargyl
Herbicide
HRAC A WSSA 1; aryloxyphenoxypropionate

 

NOMENCLATURE
clodinafop-propargyl
Common name clodinafop-propargyl
IUPAC name prop-2-ynyl (R)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate
Chemical Abstracts name propynyl (R)-2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoate
CAS RN [105512-06-9]; [105511-96-4] racemate Development codes CGA 184927 (Ciba-Geigy)

clodinafop
Common name clodinafop (BSI, pa E-ISO)
CAS RN [114420-56-3]

PHYSICAL CHEMISTRY
clodinafop-propargyl
Composition (R)- isomer. Mol. wt. 349.7 M.f. C17H13ClFNO4 Form Colourless crystals. M.p. 59.5 ºC; (tech., 48.2-57.1 ºC) V.p. 3.19 ´ 10-3 mPa (25 ºC) (OECD 104) KOW logP = 3.9 (25 ºC) Henry 2.79 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.37 (20 °C) Solubility In water 4.0 mg/l (pH7, 25 ºC). In ethanol 97, acetone 880, toluene 690, n-hexane 0.0086, n-octanol 25 (all in g/l, 25 ºC). Stability Relatively stable in acidic media at 50 ºC, hydrolyses in alkaline media; DT50 (25 ºC) 64 h (pH 7), 2.2 h (pH 9).

COMMERCIALISATION
History Reported by J. Amrein et al. (Proc. Br. Crop Prot. Conf. - Weeds,1989, 1, 71-76). Introduced by Ciba-Geigy AG (now Syngenta AG) and first marketed in 1990. Patents EP B 0083556, US 4713109 Manufacturers Syngenta

APPLICATIONS
clodinafop-propargyl
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Post-emergence, systemic grass herbicide. Phytotoxic symptoms appear within 1-3 weeks, affecting meristematic tissue. Uses Used for post-emergence control of annual grasses, including Avena, Lolium, Setaria, Phalaris and Alopecurus, in cereals, at 30-60 g/ha. Phytotoxicity Low toxicity to spring and winter wheat. Formulation types EC; WP. Compatibility Mainly used in combination with the safener cloquintocet-mexyl. Selected products: mixtures: 'Celio' (+ cloquintocet-mexyl) (France) (Syngenta); 'Topik' (+ cloquintocet-mexyl) (Syngenta)

OTHER PRODUCTS
clodinafop-propargyl
'Conduct' (Syngenta); 'Discover' (Syngenta); 'Magestan' (Syngenta); 'Boulevard' (GreenCrop); 'Marathon' (Me2) mixtures: 'Hawk' (+ trifluralin) (Syngenta); 'Horizon' (+ cloquintocet-mexyl) (Canada) (Syngenta); 'Amazon' (+ diflufenican) (Bayer CropScience, Syngenta); 'Lucifer' (+ diflufenican) (Bayer CropScience) Discontinued products mixtures: 'Amazon TP' * (+ diflufenican) (Novartis)

ANALYSIS
Details available from Syngenta.

MAMMALIAN TOXICOLOGY
clodinafop-propargyl
Oral Acute oral LD50 for male rats 1392, female rats 2271, mice >2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). May cause skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats 2.325 mg/l air. NOEL (2 y) for rats 0.35, (18 mo) for mice 1.2, (1 y) for dogs 3.3 mg/kg b.w. daily. ADI 0.004 mg/kg b.w. Toxicity class WHO (a.i.) III (company classification) EC classification (R22, R43)

ECOTOXICOLOGY
clodinafop-propargyl
Birds LD50 (8 d) for mallard ducks >2000, bobwhite quail >1455 mg/kg. Fish LC50 (96 h) for rainbow trout 0.39, carp 0.46, catfish 0.43 mg/l. Daphnia LC50 (48 h) >74 mg/l. Algae EC50 (96-120 h) for Scenedesmus subspicatus 25, Microcystis >65.5, Navicula 6.8 mg/l. Bees LD50 (48 h, oral and contact) >100 mg/bee. Worms LC50 for earthworms 210 mg/kg.

ENVIRONMENTAL FATE
Animals Hydrolysed to the corresponding acid which is excreted in urine and faeces. Plants In plants, rapidly degraded to the acid derivative as major metabolite. Soil/Environment In soil, undergoes rapid degradation to the free acid (DT50 <2 h) and then further to phenyl and pyridine moieties which are bound to the soil and mineralised. The free acid is mobile in soil, but is further degraded with DT50 5-20 d; in practice, there is a negligible leaching potential.