Cyanazine 氰草津

氰草津

CAS号：21725-46-2
英文名： cyanazine
化学名称：2-（4-氯-6-乙氨基-1，3，5-三嗪-2-基氨基）-2-甲基丙腈
其他名称： 百得斯、草净津、丙腈津、Bladex、Foxtrol。
分子式：C9H13ClN6
分子量：240.70

理化性质：白色结晶。熔点167.5-169℃，20℃蒸气压为（0.21×10-6Pa）。25℃水中溶解度为171mg/L，在下列溶剂中溶解度（25℃，g/L）：苯15，氯仿210，乙醇45，己烷15。对光、热稳定，在中性、微酸性或微碱性介质中可水解。

毒性： 对人畜毒性中等，对大鼠经口急性LD50为182-288毫克/公斤，经皮急性LD50＞1200毫克/公斤，对鸟类、鱼类毒性较低。

作用特点及杀草谱： 是内吸选择性除草剂，主要通过根吸收，叶也能吸收。对玉米安全，持效期2-3个月，对后茬小麦无影响。除草活性与土壤有机质含量和质地有密切关系。有机质多或为粘土则除草剂用量也需适当增加。在沙性重，有机质含量少时易出现药害。杀草广谱，能防除大多数1年生禾本科杂草及阔叶杂草。如早熟禾、马唐、狗尾草、稗草、蟋蟀草、雀稗草、蓼、田旋花、莎草、马齿苋等。可与莠去津混用扩大杀草谱；施药后遇雨或进行灌溉可提高防效，干旱时用药如无灌溉条件可以浅耙，使药物与土壤充分混合；干旱地区也可苗后施药。茎叶处理时以15～30℃为宜，低温、湿度大时对玉米不安全。砂土禾有机质含量低于1%的砂性壤土不宜使用。

适用于玉米、豌豆、蚕豆、马铃薯、甘蔗、棉花等作物田防除多种禾本科杂草和阔叶杂草。

使用方法：
1.玉米播种后出苗前使用 每亩用80%可湿性粉剂150-200克，或43%胶悬剂200-300毫升，对水20-30公斤，对土表均匀喷雾处理。
2.玉米出苗后使用 玉米3-4叶期，杂草2-5叶期，每亩用80%可湿性粉剂100-167克，或43%胶悬剂186-360毫升，兑水20-3 0公斤喷雾。

剂型： 50%、80%可湿性粉剂，43%、50%胶悬剂，15%颗粒剂。30%、40%氰津·莠悬浮剂；40%、42%氰津·乙悬浮剂； 40%氰·乙·莠悬浮剂
生产方法：将三聚氯氰的丙酮悬浮液和氨基异丁腈冷却到0℃后，搅拌下加入50%的氢氧化钠溶液，反应混合物呈中性后加入乙胺和氢氧化钠，即得氰草津。
生产情况：该品1971年由Shell化学公司投产，德国巴斯夫股份有限公司于1987年在我国正式登记百得斯43%悬浮剂，用于玉米防除一年生杂草。山东大成农药股份有限公司（原山东农药工业股份有限公司，3000t/a），河北张家口市宣化农药厂；沙隆达郑州农药有限公司；淄博农邦农药有限公司；江苏省百灵农化有限责任公司；浙江省长兴第一化工有限公司

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

NOMENCLATURE
Common name cyanazine (BSI, E-ISO, (f) F-ISO, WSSA)
IUPAC name 2-(4-chloro-6-ethylamino-1,3,5-triazin-2-ylamino)-2-methylpropiononitrile
Chemical Abstracts name 2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile
CAS RN [21725-46-2] EEC no. 244-544-9 Development codes WL 19 805; SD 15 418 (both Shell); DW 3418

PHYSICAL CHEMISTRY
Composition Tech. grade ³95% pure. Mol. wt. 240.7 M.f. C9H13ClN6 Form Tech. cyanazine is a white crystalline solid. M.p. 167.5-169 ºC; (tech., 166.5-167 ºC) V.p. 2 ´ 10-4 mPa (20 ºC) KOW logP = 2.1 S.g./density 1.29 kg/l (20 ºC) Solubility In water 171 mg/l (25 ºC). In methylcyclohexanone, chloroform 210, acetone 195, ethanol 45, benzene, hexane 15, carbon tetrachloride <10 (all in g/l, 25 ºC). Stability Stable to heat (1.8% decomposition after 100 h at 75 ºC), and to light. Stable in solution between pH 5 and 9, hydrolysed by strong acids and alkalis. pKa 0.63, v. weak base

COMMERCIALISATION
History Herbicide reported by W. J. Hughes et al. (Proc. North Cent. Weed Control Conf., 21st, 1967, p. 27). Introduced by Shell Research Ltd (now BASF AG, who sold commercial rights in EU to Feinchemie Schwebda in 2001). Patents GB 1132306 Manufacturers BASF; Griffin

APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Maize tolerance of triazines is attributed to conjugation with glutathione. Mode of action Selective systemic herbicide, absorbed by the roots (with translocation acropetally to the leaves), and also by the foliage. Uses Used for general weed control (a) pre-emergence to the crop, at 1-3 kg/ha, in broad beans, maize and peas; (b) post-emergence in barley and wheat during the early tillering stage, at 0.26-0.33 kg/ha in combination with a variety of other herbicides for the control of broad-leaved weeds. Other crops for which it is used include: cotton, oilseed rape, forestry, potatoes, soya beans, sugar cane. Phytotoxicity Selective if applied according to label recommendations. Formulation types GR; SC; WG; WP. Selected products: 'Bladex' (Feinchemie Schwebda); 'Cy-Pro' (Griffin)

OTHER PRODUCTS
'Gramex' (Japan) (BASF); 'Canter' (Barclay); 'Fortrol' (Feinchemie Schwebda) mixtures: 'Bellater' (+ atrazine) (Feinchemie Schwebda); 'Bullet' (+ pendimethalin) (Feinchemie Schwebda); 'Halbard' (+ diflufenican) (Feinchemie Schwebda) Discontinued products: 'Match' * (BASF); 'Reply' * (Cyanamid); 'Urlac' * (BASF) mixtures: 'Activus' * (+ pendimethalin) (Cyanamid); 'Topshot' * (+ 2,4-DB+ bentazone) (Cyanamid); 'Angle' * (+ terbuthylazine) (Novartis)

ANALYSIS
Product analysis by hplc (CIPAC Handbook, 1985, 1C, 2039) or by glc or hplc (AOAC Methods, 17th Ed., 991.32; Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 275). Residues in plants determined by glc with ECD or FID (ibid.), and in soils by glc or hplc (ibid.). In water, by lc with u.v. detection (AOAC Methods, 17th Ed., 992.14).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 182-334, mice 380, rabbits 141 mg/kg. Skin and eye Acute percutaneous LD50 for rats >1200, rabbits >2000 mg/kg. Non-irritating to skin and eyes. Inhalation LC50 >2460 mg/m3 air, as cyanazine dust. NOEL (2 y) for rats 12, dogs 25 mg/kg diet. Water GV 0.6 mg/l (TDI 0.198 mg/kg b.w.). Toxicity class WHO (a.i.) II; EPA (formulation) II (DF, SC and WP), III (GR) EC classification Xn; R22| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >2000, quail 400 mg/kg. Fish LC50 (48 h) for harlequin fish 10 mg/l; LC50 (96 h) for fathead minnow 16 mg/l. Daphnia LC50 (48 h) 42-106 mg/l. Algae EC50 (96 h) <0.1 mg/l. Bees Not toxic to bees. LD50 (topical) >100 mg/bee (tech. in acetone); (oral) >190 mg/bee (tech. as dust).

ENVIRONMENTAL FATE
Animals In rats and dogs, following oral administration, cyanazine is rapidly metabolised and eliminated within c. 4 days. Plants In plants, the nitrile group is hydrolysed to a carboxylic acid group, and the chlorine atom is replaced by a hydroxy group (K. I. Beynon et al., Pestic. Sci., 1972, 3, 293-305). Soil/Environment Microbial degradation in soil occurs within one growth period. Metabolism is similar to that in plants. DT50 in soil c. 2 w. (K. I. Beynon et al., Pestic. Sci., 1972, 3, 293-305, 379-401).