Trinexapac-ethyl 抗倒酯

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抗倒酯

CAS:95266-40-3
英文名称: Trinexapac-ethyl
化学名称:4-环丙基(羟基)亚甲基-3,5-二酮环己烷羧酸乙酯;4-(Cyclopropyl-alpha-hydroxymethylene)-3,5-dioxo-cyclohexanecarboxylic acid ethyl ester
分子式:C13H16O5
分子量:252.27( FW:252.27)

理化性质:无色结晶,熔点36.0℃(mp:36.0℃),沸点:>270℃(bp:>270℃),pKa: 4.7,蒸汽压:1.6mPa(20℃) 、2.16mpa(25℃),溶解度(20℃,g/L):水2.8(pH 4.9)、10.2(pH 5.5)、21.1(pH 8.2);乙醇、丙酮、甲苯、正辛醇易溶;己烷中溶解度为5%。
毒性:大鼠急性经口LD504450㎎/㎏、经皮 LD50>4000㎎/㎏、吸入LC50(48h)>5.3㎎/l;对皮肤和眼睛无刺激。
作用特点及用途:本品属环己烷羧酸类植物生长调节剂。赤霉素生物合成抑制剂。通过降低赤霉素的含量,控制作物旺长。以0.4-1.0kg/公顷在禾谷类作物、蓖麻、水稻、向日葵和草皮上施用,显示生长抑制作用。芽后施用可防止倒伏和改善收获效率,施于叶部,可转移到生长的枝条上,可减少节间的伸长。

剂型:12.5%,25%乳油。
生产方法:1、由3,5-二氧代环己烷基羧酸乙酯与环丙基甲酰氯反应生成。

2、马来酸二乙酯和丙酮在有机胺存在下,高压缩合得2-丙酮基-1,4-丁二酸二乙酯,然后在醇钠存在下进行成环,得到3,5-二氧环己基甲酸乙酯,再与环丙甲酸酐在碱性条件下反应得抗倒酯。

生产情况:江苏山达化工有限公司,金坛市合恩泰化工有限公司(原金坛市鸿泰化工有限公司), 浙江泰达作物科技有限公司;天津百灵消毒剂有限责任公司;迈克斯(如东)化工有限公司(50t/a);江苏辉丰农化股份有限公司(100t/a)阜宁宁翔化工有限公司;安徽绩溪县徽煌化工有限公司

其他:瑞士先正达作物保护有限公司2008年在我国获得登记,登记的250克/升抗倒酯乳油产品,登记作物和用途为防止小麦倒伏;121克/升抗倒酯可溶液剂产品,登记作物和用途为调节高羊茅草坪生长。

 

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trinexapac-ethyl
Plant growth regulator

 

  trinexapac-ethyl

NOMENCLATURE
trinexapac-ethyl
Common name trinexapac-ethyl (BSI, pa E-ISO)
IUPAC name ethyl 4-cyclopropyl(hydroxy)methylene-3,5-dioxocyclohexanecarboxylate
Chemical Abstracts name ethyl 4-(cyclopropylhydroxymethylene)-3,5-dioxocyclohexanecarboxylate
Other names cimectacarb-ethyl* (rejected name) CAS RN [95266-40-3] Development codes CGA 163 935 (Ciba-Geigy)

trinexapac
Common name trinexapac (BSI, pa E-ISO)
CAS RN [104273-73-6] Development codes CGA 179500 (Ciba-Geigy)

PHYSICAL CHEMISTRY
trinexapac-ethyl
Composition Tech. is ³92% pure. Mol. wt. 252.3 M.f. C13H16O5 Form White, odourless solid; (tech. is a yellow to red-brown liquid (30 °C) and a solid-liquid melt (20 °C), with a slight sweet odour). M.p. 36 ºC B.p. >270 ºC V.p. 1.6 mPa (20 ºC); 2.16 mPa (25 ºC) (OECD 104) KOW logP = 1.60 (pH 5.3, 25 ºC) Henry 5.4 ´ 10-4 Pa m3 mol-1 S.g./density 1.215 g/cm3 (20 ºC) Solubility In water 2.8 (pH 4.9), 10.2 (pH 5.5), 21.1 (pH 8.2) (all in g/l, 25 ºC). In ethanol, acetone, toluene, n-octanol 100%, n-hexane 5% (25 ºC). Stability Heat-stable up to boiling point. Photolytically and hydrolytically stable under normal environmental conditions (pH 6-7, 25 ºC). Less stable in alkali. pKa 4.57 F.p. 133 ºC (1013 mbar) (EEC A9)

trinexapac
Mol. wt. 224.2 M.f. C11H12O5 M.p. 144.4 °C B.p. c. 220 °C V.p. 2.3 ´ 10-3 mPa (25 °C) (OECD 104, EEC A4) KOW logP = 1.8 (pH 2) S.g./density 1.41 (20 °C) Solubility In water 13 (pH 5.0), 200 (pH 6.8), 260 (pH 8.4) (all in g/l). In acetone 95, ethyl acetate 37, methanol 84, octanol 17 (all in g/l). pKa pKa1 5.32, pKa2 3.93

COMMERCIALISATION
History First reported by E. Kerber et al., Proc. Br. Crop Protection Conf., 1989, I, 83. Introduced by Ciba-Geigy AG (now Syngenta AG) and first marketed in Switzerland in 1992. Patents EP 126713; US 4693745 Manufacturers Syngenta

APPLICATIONS
trinexapac-ethyl
Biochemistry Inhibits 3b-hydroxylation of GA20 to GA3 in gibberellin biosynthesis. The reduced level of gibberellins leads to growth retardation of plants. Mode of action Plant growth regulator and retardant, which reduces stem growth by inhibition of internode elongation. Absorbed by the foliage, with translocation to the growing shoot. Uses Used for the prevention of lodging in cereals and in winter oilseed rape, at 0.1-0.3 kg/ha. Also used in turf, at 0.15-0.5 kg/ha, to reduce mowing; and as a maturation promoter in sugar cane at 0.1-0.25 kg/ha. Phytotoxicity Could cause inhibition or growth stoppage of some plants, e.g. grasses, aquatic plants and algae. Formulation types EC; ME; WP. Compatibility Compatibility of little importance because of late timing of application; compatible with certain late-season fungicides. Selected products: 'Bonus' (Syngenta); 'Moddus' (Syngenta); 'Primo' (Syngenta)

OTHER PRODUCTS
trinexapac-ethyl
'Sonis' (Syngenta); 'Shortcut' (Scotts UK) Discontinued products: 'Metro' * (Novartis); 'Vision' * (Novartis)

ANALYSIS
All methods use hplc, for both ester and acid metabolite.

MAMMALIAN TOXICOLOGY
trinexapac-ethyl
Oral Acute oral LD50 for rats 4460 mg/kg. Skin and eye Acute percutaneous LD50 for rats >4000 mg/kg. Not irritant to skin or eyes of rabbits. Non-sensitising to skin (guinea pigs). Inhalation LC50 (48 h) for rats >5.3 mg/l. NOEL (2 y) for rats 115 mg/kg b.w. daily; (18 mo) for mice 451 mg/kg b.w. daily; (1 y) for dogs 31.6 mg/kg b.w. daily. ADI 0.316 mg/kg b.w. Toxicity class WHO (a.i.) U (company classification)

ECOTOXICOLOGY
trinexapac-ethyl
Birds LD50 for ducks and quail >2000 mg/kg. LC50 (8 d) for ducks and quail >5000 ppm. Fish LC50 (96 h) for trout, carp, bluegill sunfish, catfish, fathead minnow 35-180 mg/l. Daphnia LC50 (96 h) 142 mg/l. Bees Non-toxic; LD50 (oral) >293 mg/bee; (contact) >115 mg/bee. Worms Low toxicity to earthworms; LC50 >93 mg/kg.

ENVIRONMENTAL FATE
Animals In rats, goats and hens, 90% excretion occurs within 24 h, all as the acid metabolite. Plants Rapid metabolism to the acid, which remains by far the predominant metabolite. Soil/Environment In soil, the ester undergoes rapid degradation, DT50 <1 d. The acid has Kd values 1.5-16, Koc 140-600. Further metabolism is rapid, DT50 typically 2-5 w. Within 4-8 w, 50% is mineralised to CO2.