Terbumeton 特丁通

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CAS号: 33693-04-8
英文名称: Terbumeton
分子量: 225.29

理化性质:无色结晶,熔点: 123-124 ℃,蒸汽压0.27 mPa (20 ℃),密度1.08 (20 ℃),溶解度(g/l, 20 ℃):水0.13,丙酮130,甲苯110,甲醇220,,二氯甲烷360,,正辛醇190。在中性、弱酸和弱碱性溶液中稳定,在强酸或强碱性介质中水解为无除草活性的2-特丁氨基-4-乙氨基-6-羟基-1,3,5-三嗪。

毒性:口服- 大鼠 LD50: 433 毫克/ 公斤; 急性经皮LD503170mg/kg, 吸入-大鼠 LC50: >10000 毫克/立方米/4小时。对大鼠皮肤无刺激,对兔眼睛有轻微刺激。鱼毒LC50(96小时):虹鳟14mg/L,斑点叉尾鮰l0mg/L,蓝鳃30mg/L,欧洲鲫鱼30mg/L。对蜜蜂无毒。水蚤LC50(48小时)40mg/L。海藻LC50为0.009mg/L。


剂型: 50%可湿性粉剂;25%特丁通与25%特丁津的混合制剂;17%特丁通与33%特丁津的混合制剂。

生产方法:由2-氯-4-乙氨基-6-叔丁基氨基-1,3,5-三嗪与甲醇钠反应生成。 或 由特丁津(terbuthylazine)与甲醇和氢氧化钠反应制得。



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HRAC C1 WSSA 5; 1,3,5-triazine


Common name terbumeton (BSI, E-ISO, (m) F-ISO)
IUPAC name N2-tert-butyl-N4-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-(1,1-dimethylethyl)-N'-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
CAS RN [33693-04-8] Development codes GS 14 259 (Geigy)

Mol. wt. 225.3 M.f. C10H19N5O Form Colourless crystals. M.p. 123-124 ºC V.p. 0.27 mPa (20 ºC) KOW logP = 3.04 Henry 4.68 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.08 (20 ºC) Solubility In water 130 mg/l (20 ºC). In acetone 130, toluene 110, methanol 220, dichloromethane 360, n-octanol 90 (all in g/l, 20 ºC). Stability Stable in neutral, weakly acidic and weakly alkaline media. Hydrolysed by strong acids and alkalis, especially at higher temperatures, with the formation of hydroxytriazine; DT50 (20 ºC) (calc.) 29 d (pH 1), 1.6 y (pH 13).

History Herbicide reported by A. Gast & E. Fankhauser (Proc. Br. Weed Control Conf., 8th, 1966, 2, 485). Introduced by J. R. Geigy S.A. (became Novartis Crop Protection AG, who ceased to manufacture or market it). Patents CH 337019; GB 814948

Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Mode of action Selective herbicide, absorbed by the leaves and roots. Uses Selective control of annual and perennial grasses and broad-leaved weeds in citrus orchards. Used in combination with terbuthylazine for herbicidal control in vineyards, apple and citrus orchards, and in forestry, at 3-6 kg total a.i./ha. Phytotoxicity Should not be applied to the vine variety Airen. May be phytotoxic to most annual plants, by drift, etc. Formulation types SC; WP.

Mixtures: 'Athado Invierno' (+ terbuthylazine+ atrazine) (Probelte); 'Athado Liquido' (+ terbuthylazine) (Probelte); 'Athado Verano' (+ terbuthylazine+ terbutryn) (Probelte) Discontinued products mixtures: 'Caragard' * (+ terbuthylazine) (Novartis)

Product analysis by glc or by acidimetric titration; details available from Syngenta. Residues determined by glc with MCD (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192; E. Knüsli, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 4, 13).

Oral Acute oral LD50 for rats 651, mice 2343 mg/kg. Skin and eye Acute percutaneous LD50 for rats >3170 mg/kg. Non-irritating to skin (rats); slightly irritating to eyes (rabbits). Inhalation LC50 (4 h) for rats >10 mg/l. NOEL (2 y) for rats 7.5 mg/kg b.w. daily; (18 mo) for mice 25 mg/kg b.w. daily; (13 w) for dogs 25 mg/kg b.w. daily. ADI 0.075 mg/kg b.w. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification Xn; R22| N; R50, R53

Fish LC50 (96 h) for rainbow trout 14, channel catfish 10, bluegill sunfish 30, crucian carp 30 mg/l. Daphnia LC50 (48 h) 40 mg/l. Algae LC50 0.009 mg/l. Bees Non-toxic to bees.

Animals In mammals, following oral administration, terbumeton is rapidly absorbed. More than 95% is eliminated within 96 hours, predominantly in the urine, with c. 25% in the faeces. Plants Demethoxylation, dealkylation (primarily de-ethylation) and conjugation are the main metabolic steps in crop plants. Soil/Environment In soil, terbumeton undergoes microbial demethylation to the hydroxytriazine. There is uncertainty about subsequent degradation. DT50 in soil c. 300 d. Moderately mobile under lab. conditions, but only slightly mobile under typical conditions of use; Koc 37.5-158, Kd 0.6-8.9.