Terbuthylazine 特丁津

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CAS号: 5915-41-3
英文名称: Terbutylazine
化学名称:2-氯-4-特丁氨基-6-乙氨基-1,3,5-三嗪; 2-tert-Butylamino-4-chloro-6-ethylamino-1,3,5-triazine;


毒性:口服- 大鼠 LD50: 1845 毫克/ 公斤; 吸入-大鼠 LC50: > 3510 毫克/立方米/4小时,80%制剂对家兔急性经皮LD503000mg/kg。对鱼低毒。

作用特点及杀草谱:三嗪类除草剂。主要通过植株的根吸收,用于防除大多数杂草。芽前施用,用于玉米、小麦、大麦、马铃薯、豌豆、高粱及柑橘等作物田中防除多种杂草,用量为1~3kg/ha。高粱田中用量1.2~ 1.8kgAI/ha;也可选择性地防除柑桔、玉米和葡萄园杂草。

剂型:500g/l SC,80%WP,50%WP


生产情况:山东润丰化工有限公司, 浙江省长兴县中山化工有限公司 ; 沙隆达郑州农药有限公司 ; 常州市迅达化工有限公司(滨海县枫霖化工有限公司;常州市鑫旺化工厂) ; 山东大成农药股份有限公司 ;江苏省百灵农化有限责任公司;山东胜邦绿野化学有限公司


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


Common name terbuthylazine (BSI, E-ISO, (f) F-ISO, ANSI, WSSA)
IUPAC name N2-tert-butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl-1,3,5-triazine-2,4-diamine
CAS RN [5915-41-3] EEC no. 227-637-9 Development codes GS 13 529 (Geigy)

Composition Tech. is ³96 % pure. Mol. wt. 229.7 M.f. C9H16ClN5 Form Colourless powder. M.p. 177-179 ºC V.p. 0.15 mPa (25 ºC) KOW logP = 3.21 (unionised) Henry 4.05 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1.188 (20 ºC) Solubility In water 8.5 mg/l (pH 7, 20 ºC). In acetone 41, ethanol 14, n-octanol 12, n-hexane 0.36 (all in g/l, 25 ºC). Stability Stable in neutral, weakly acidic and weakly alkaline media; hydrolysed in acidic or alkaline media; DT50 (20 ºC) (calc.) 8 d (pH 1), 12 d (pH 13). In natural sunlight, DT50 >40 d. pKa 2.0, v. weak base F.p. >150 ºC

History Herbicide reported by A. Gast & E. Fankhauser (Proc. Br. Weed Control Conf., 8th, 1966, 2, 485). Introduced by J. R. Geigy S.A. (now Syngenta AG). Patents BE 540590; GB 814947 Manufacturers Dow AgroSciences; Makhteshim-Agan; Syngenta

Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Maize tolerance of triazines is attributed to conjugation with glutathione. Mode of action Herbicide, absorbed mainly by the roots. Uses Broad-spectrum pre- or post-emergence weed control in maize, sorghum, vines, fruit trees, citrus, coffee, oil palm, cocoa, olives, potatoes, peas, beans, sugar cane, rubber, and in forestry in tree nurseries and new plantings. It remains largely in the topsoil, controlling a wide range of weeds, at rates of 0.6-3 kg/ha; high rates are only recommended as band applications. In Europe, used mainly on maize and sorghum with a maximum application rate of 1.5 kg/ha, mainly in mixture with other herbicides. Phytotoxicity Phytotoxic to many annual plants and to aquatic plants. Formulation types SC; WG. Selected products: 'Folar' (Syngenta); 'Gardoprim' (Syngenta); 'Click' (Sipcam); 'Tyllanex' (Makhteshim-Agan)

'Fenican' (Syngenta) mixtures: 'Bolero' (+ diflufenican) (Syngenta); 'Gardo Gold' (+ S-metolachlor) (Syngenta); 'Gardobuc' (+ bromoxynil octanoate) (Syngenta, Bayer CropScience); 'Gardoprim Plus Gold' (+ S-metolachlor) (Syngenta); 'Lido' (+ pyridate) (Syngenta); 'Alanex TBA' (+ alachlor) (Makhteshim-Agan); 'Alpha Bromotril PT' (+ bromoxynil) (name used for all forms of bromoxynil) (Makhteshim-Agan); 'Arpix Ter' (+ bromoxynil) (Aragro); 'Artett' (+ bentazone-sodium) (BASF); 'Athado Invierno' (+ atrazine+ terbumeton) (Probelte); 'Athado Liquido' (+ terbumeton) (Probelte); 'Athado Super' (+ glyphosate) (Probelte); 'Athado Verano' (+ terbutryn+ terbumeton) (Probelte); 'Batallion' (+ terbutryn) (Makhteshim-Agan); 'Butazin' (+ glyphosate) (Makhteshim-Agan); 'Glifazin' (+ glyphosate) (Makhteshim-Agan); 'Olagan' (+ terbutryn) (Makhteshim-Agan); 'RPA 04481H' (+ bromoxynil) (Bayer CropScience); 'Titer' (+ rimsulfuron) (DuPont); 'Topanex Ter' (+ diuron+ glyphosate) (Aragro); 'Wonder' (+ rimsulfuron) (DuPont) Discontinued products: 'Primatol M' * (Ciba-Geigy); 'Stentan' * (Ciba-Geigy) mixtures: 'Angle' * (+ cyanazine) (Novartis); 'Caragard' * (+ terbumeton) (Novartis); 'Gardoprim Plus' * (+ metolachlor) (Syngenta); 'Opogard' * (+ terbutryn) (Syngenta); 'Primafit' * (+ pendimethalin) (Novartis); 'Skirmish' * (+ isoxaben) (Novartis); 'Topogard' * (+ terbutryn) (Syngenta); 'Zintan' * (+ metolachlor+ pyridate) (Syngenta); 'Primatol 3588' * (+ secbumeton) (Ciba-Geigy); 'Templar' * (+ bromoxynil) (Makhteshim-Agan)

Product analysis by glc with FID (CIPAC Handbook, 1983, 1B, 1899; AOAC Methods, 17th Ed., 981.04, 971.08; FAO Specification (CP/61); J. Assoc. Off. Anal. Chem., 1981, 64, 504) or by titration (CIPAC Handbook, 1983, 1B, 1897; see also method for simazine, ibid., 1344); particulars available from Syngenta. Residues determined by glc with MCD or FPD (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 1590->2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. No skin or eye irritation. Not a skin sensitiser. Inhalation LC50 (4 h) for rats >5.3 mg/l air. NOEL (1 y) for dogs 0.4 mg/kg b.w. daily; (lifetime) for rats 0.22 mg/kg b.w. daily; (2 y) for mice 15.4 mg/kg b.w. daily. ADI 0.0022 mg/kg. Water GV 7 mg/l (TDI 2.2 mg/kg b.w.). Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification (R22)

Birds Acute oral LD50 for ducks and quail >1000 mg/kg. Dietary LC50 (8 d) for ducks and quail >5620 ppm. Fish LC50 (96 h) for rainbow trout 3.8-4.6, bluegill sunfish 7.5, carp and catfish 7.0 mg/l. Daphnia LC50 (48 h) 21-50.9 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 0.016-0.024 mg/l. Bees LD50 (oral and contact) >100 mg/bee. Worms LC50 (7 d) for earthworms >200 mg/kg soil. Other beneficial spp. No effects on bacterial respiration and nitrification in range 10.9-109 mg/kg soil.

Animals In mammals, following oral administration, 72-84% is eliminated in the urine and faeces within 24 h, and almost all within 48 h. A de-ethyl metabolite forms rapidly, followed by conjugates of products formed by oxidation of one methyl group of the tert-butyl moiety. All are rapidly excreted. Plants Triazine-tolerant plants (e.g. maize) rapidly de-chlorinate terbuthylazine to hydroxy-terbuthylazine. Various amounts of de-ethylated and hydroxy de-ethylated metabolites are produced, depending on the plant species. Soil/Environment Adsorption on soils is strong: Koc 162-278, Kd 2.2-25 are typical values for light agricultural soils. Terbuthylazine is only slightly mobile. Microbial degradation proceeds mainly by de-ethylation and hydroxylation, with eventual ring cleavage. DT50 30-60 d in biologically active soil.