Atrazine 莠去津,阿特拉津

莠去津

莠去津英文通用名：atrazine； 化学名称：2-氯-4-二乙胺基-6-异丙胺基-1，3，5-三嗪； 其他名称：阿特拉津、Aatrex、Primatola、克esaprim，克-30027。 理化性质：外观为白色粉末，熔点为173－175℃,20℃时的蒸气压为40μPa，在水中的溶解度为33mg/L，易溶于有机溶剂，在微酸或微碱性介质中较稳定，但在较高温度下，碱或无机酸可使其水解。

用途
莠去津，也叫阿特拉津，主要是甜高粱、甘蔗、高粱、玉米封闭除草剂。
毒性
对人畜低毒，大鼠急性经口LD50为1780毫克/公斤，对兔急性经皮LD50为7000 莠去津
毫克/公斤，对大鼠慢性毒性经口无作用剂量为1000毫克/公斤。
莠去津的除草性质是1957年由瑞士的H.盖辛和E.克努斯利发现的，1958年由瑞士的嘉基公司开发生产，后来发展成世界产量最大的除草剂。中国在70年代开始生产。
生产方法是用三聚氯氰分两步依次和乙胺及异丙胺在碱性介质中反应，取代两个氯原子，生成莠去津原药。 莠去津是芽前土壤处理除草剂，也可芽后茎叶处理。主要通过植物根部吸收并向上传导，抑制植物的光合作用，使其枯死。它的杀草谱较广，可防除多种一年生禾本科和阔叶杂草。通常加工成可湿性粉剂和悬浮剂使用，适用于玉米、高粱、甘蔗等旱田作物除草，尤其对玉米有较好的选择性（因玉米体内有解毒机制
剂型 40%悬浮剂、50%可湿性粉剂。

化学结构
分子式：C8H14ClN5
分子量：215.72

特点
是内吸选择性苗前、苗后除草剂。根吸收为主，茎叶吸收很少。杀草作用和选择性同西玛津，易被雨水淋洗至土壤较深层，对某些深根草亦有效，但易产生药害。持效期也较长。 适用范围 适用于玉米、高粱、甘蔗、果树、苗圃、林地防除马唐、稗草、狗尾草、莎草、看麦娘、蓼、藜、十字花科、豆科杂草，对某些多年生杂草也有一定抑制作用。

使用方法
1.玉米田的使用 夏玉米在播种后出苗前用药，土壤有机质质量在1%-2%的华北、山东等地，每亩用50%可湿性粉剂150-200克，或40%悬浮剂175-200毫升；土壤有机质含量大于3%-6%的东北地区，每亩用50%可湿性粉剂200-250克，或40%的悬浮剂200-250克，沙质土壤用下限，粘质土壤用上限。播种后1-3天，对水30公斤均匀喷雾土表。玉米出苗后用药，适期为玉米4叶期，杂草2-3叶期；有机质含量低的沙质土壤，每亩用50%可湿性粉剂或40%悬浮剂200-250克。对水30-50公斤喷雾。春玉米每亩用40%悬浮剂200-250毫升，加水30-50公斤，播后苗前土表喷雾，春旱药后混土，或适量灌溉。或在玉米4叶期作茎叶处理。玉米和冬小麦连作区，为减轻或消除莠去津对小麦的药害，可用莠去津减量与草净津、拉索、都尔、2，4-D丁酯、伴地农、绿麦隆除草剂混用。
2.甘蔗田使用 甘蔗下种后5-7天，杂草部分出土，每亩用50%可湿性粉剂或40%悬浮剂200-250克，加水30公斤，对地表均匀喷雾。
3.茶园、果园、葡萄园使用 4-5月份田间杂草萌发高峰期，先将已出土大草和越冬杂划铲除，然后每亩用40%悬浮剂250-300克，对水40公斤均匀喷布土表。
使用中干旱对药效发挥影响较大，主要作用于双子叶植物，侧重封闭，对大草效果比较不理想。

注意事项
1.莠去津持效期长，对后茬敏感作物小麦、大豆、水稻等有害，持效期达2-3个月，可通过减少用药量，与其他除草剂如烟嘧磺隆或甲基磺草酮等混用解决。
2.桃树对莠去津敏感，不宜在桃园使用。玉米套种豆类不能使用。
3.土表处理时，要求施药前，地要整平整细。 4.施药后，各种工具要认真清洗。

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

NOMENCLATURE
Common name atrazine (BSI, E-ISO, (f) F-ISO, ANSI, WSSA, JMAF)
IUPAC name 6-chloro-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine
CAS RN [1912-24-9] EEC no. 217-617-8 Development codes G 30 027 (Geigy)

PHYSICAL CHEMISTRY
Composition Tech. is ³96% pure. Mol. wt. 215.7 M.f. C8H14ClN5 Form Colourless powder. M.p. 175.8 ºC B.p. 205.0 °C/101 kPa V.p. 3.85 ´ 10-2 mPa (25 ºC) (OECD 104) KOW logP = 2.5 (25 ºC) Henry 1.5 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.23 (22 °C) Solubility In water 33 mg/l (pH 7, 22 ºC). In ethyl acetate 24, acetone 31, dichloromethane 28, ethanol 15, toluene 4.0, n-hexane 0.11, n-octanol 8.7 (all in g/l, 25 ºC). Stability Relatively stable in neutral, weakly acidic and weakly alkaline media. Rapidly hydrolysed to the hydroxy derivative in strong acids and alkalis, and at 70 ºC in neutral media; DT50 (pH 1) 9.5, (pH 5) 86, (pH 13) 5.0 d. pKa 1.7, v. weak base

COMMERCIALISATION
History Herbicide reported by H. Gysin & E. Knüsli (Proc. Int. Congr. Crop Prot., 4th, Hamburg, 1957). Introduced by J. R. Geigy S.A. (now Syngenta AG). Patents BE 540590; GB 814947 Manufacturers Agrochem; Atanor; Crystal; Dow AgroSciences; Drexel; DuPont; Hegang Heyou; Hesenta; Makhteshim-Agan; Meghmani; Nagarjuna Agrichem; Oxon; Rallis; Sannong; Sharda; Syngenta

APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Maize tolerance is attributed to rapid detoxification by glutathione transferases. Mode of action Selective systemic herbicide, absorbed principally through the roots, but also through the foliage, with translocation acropetally in the xylem and accumulation in the apical meristems and leaves. Uses Pre- and post-emergence control of annual broad-leaved weeds and annual grasses in maize, sorghum, sugar cane, pineapples, chemical fallow, grassland, macadamia nuts, conifers, industrial weed control. In Europe, use is concentrated in maize and sorghum at £1.5 kg/ha. Used also in combinations with many other herbicides. Phytotoxicity Phytotoxic to many crops, including most vegetables, potatoes, soya beans, and peanuts. Formulation types FW; GR; SC; WG; WP. Selected products: 'AAtrex' (USA) (Syngenta); 'Agri-atrazina' (Cequisa); 'Aktikon' (Nitrokémia); 'Atranex' (Makhteshim-Agan); 'Atraplex' (Ingeniería Industrial); 'Atrataf' (Rallis); 'Atratylone' (Agriphar); 'Atrazol' (Sipcam); 'Attack' (Devidayal); 'Coyote' (Milenia); 'Dhanuzine' (Dhanuka); 'Sanazine' (Dow AgroSciences); 'Surya' (Nagarjuna Agrichem); 'Triaflow' (Inquiport); 'Zeazin S 40' (Istrochem); mixtures: 'Bicep II Magnum' (+ benoxacor+ S-metolachlor) (USA) (Syngenta); 'Bicep Magnum' (+ S-metolachlor) (USA) (Syngenta); 'Callisto' (+ mesotrione) (Syngenta); 'Gesaprim' (+ terbutryn) (Europe) (Syngenta); 'Marksman' (+ dicamba-potassium) (Syngenta, BASF); 'Erunit' (+ acetochlor+ AD 67) (Nitrokémia); 'Keystone' (+ dichlormid+ acetochlor) (Dow AgroSciences); 'Trinovin' (+ simazine+ amitrole) (Efthymiadis)

OTHER PRODUCTS
'Weedex Liquid' (Syngenta); 'Atradex' (Crop Care); 'Atrazina' (Cequisa); 'Atred' (Chemiplant); 'Azoprim' (Azot); 'Cornazine' (Papaeconomou); 'Crisazina' (Crystal); 'DG90' (Sipcam UK); 'Fogard' (Isagro); 'Gladezine' (Marman); 'Herpazine' (Agrochem); 'Mebazine' (Bayer CropScience); 'Trac' (Atanor); 'Vectal' (Bayer CropScience); 'Zeacas' (CAS) mixtures: 'A-11976E' (+ glyphosate-isopropylammonium) (Syngenta); 'Bicep Magnum TR' (+ flumetsulam+ S-metolachlor) (Syngenta); 'Alazine' (+ alachlor) (Makhteshim-Agan); 'Anibal' (+ diuron) (Aragro); 'Aracloro Super' (+ alachlor) (Aragro); 'Aspect' (+ flufenacet) (Bayer CropScience); 'Aterbutex' (+ terbutryn) (Makhteshim-Agan); 'Aterbutox' (+ terbutryn) (Makhteshim-Agan); 'Athado Invierno' (+ terbumeton+ terbuthylazine) (Probelte); 'Atoll' (+ isoxaflutole) (Bayer CropScience); 'Atramet Combi' (+ ametryn) (Makhteshim-Agan); 'Atrasim' (+ simazine) (Makhteshim-Agan); 'Axiom AT' (+ flufenacet+ metribuzin) (Bayer CropScience); 'Barko' (+ metosulam) (Dow AgroSciences); 'Basis Gold' (+ nicosulfuron+ rimsulfuron) (DuPont); 'Bellater' (+ cyanazine) (Feinchemie Schwebda); 'Brox-AT' (+ bromoxynil octanoate) (Albaugh); 'Bullet' (+ alachlor) (Monsanto); 'Century' (+ dimethenamid) (BASF); 'Cinch ATZ' (+ S-metolachlor) (USA) (DuPont); 'Clark' (+ bromoxynil octanoate) (Nufarm SA, Syngenta); 'Degree Xtra' (+ acetochlor) (with safener) (Monsanto); 'Field Master' (+ glyphosate-isopropylammonium+ acetochlor) (Monsanto); 'Fogart' (+ simazine) (Makhteshim-Agan); 'FulTime' (+ dichlormid+ acetochlor) (Dow AgroSciences); 'G-Max Lite' (+ dimethenamid-P) (BASF); 'Guardsman Max' (+ dimethenamid-P) (BASF); 'Guardsman' (+ dimethenamid) (BASF); 'Harness Xtra' (+ acetochlor) (Monsanto); 'Karal' (+ bromoxynil) (Nufarm SA); 'Laddok' (+ bentazone-sodium) (BASF, Sipcam); 'Lariat' (+ alachlor) (Monsanto); 'Leadoff' (+ dimethenamid) (DuPont); 'Liberty ATZ' (+ glufosinate-ammonium) (Bayer CropScience); 'Metto' (+ metosulam) (Dow AgroSciences, Bayer CropScience); 'Propachlor Doble' (+ alachlor) (Probelte); 'Ready Master ATZ' (+ glyphosate-isopropylammonium) (Monsanto); 'Sabrine' (+ bromoxynil) (Nufarm SA); 'Shotgun' (+ 2,4-D-2-ethylhexyl) (UAP, Platte); 'Simapron Doble' (+ simazine) (Probelte); 'Simazat' (+ simazine) (Drexel); 'Triamex' (+ simazine) (Bayer CropScience); 'Zeazin Mix DKV' (+ prometryn) (Istrochem); 'Zeazin Mix Extra' (+ metolachlor+ prometryn) (Istrochem) Discontinued products: 'Atratol' * (Ciba); 'Gésaprime' * (Syngenta); 'Primatop' * (Ciba-Geigy); 'Cekuzina T' * (Cequisa); 'Griffex' * (Griffin); 'Hungazin' * (Budapest Chemical); 'Maizina' * (Sipcam); 'Zeapos' * (Sagrochem) mixtures: 'Bicep II' * (+ benoxacor+ metolachlor) (Syngenta); 'Bicep' * (+ metolachlor) (USA) (Syngenta); 'Primagram' * (+ metolachlor) (Novartis); 'Primatol' * (+ prometon) (Ciba-Geigy); 'Primextra II Magnum' * (+ benoxacor+ S-metolachlor) (Syngenta); 'Primextra Safeneur' * (+ benoxacor+ metolachlor) (Syngenta); 'Primextra' * (+ benoxacor+ metolachlor) (Europe) (Novartis); 'Primextra' * (+ S-metolachlor) (Syngenta); 'Sutazine' * (+ butylate) (Syngenta); 'Contour' * (+ imazethapyr-ammonium) (BASF); 'Surpass 100' * (+ dichlormid+ acetochlor) (Dow AgroSciences); 'Vorox(i)Granulat 371' * (+ sebuthylazine+ amitrole) (Spiess)

ANALYSIS
Product analysis by glc with FID (CIPAC Handbook, 1998, H, 33; FAO Specification (CP/61); AOAC Methods, 17th Ed., 971.08). Residues determined by glc with ECD or FID (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 92; E. Knüsli, Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 600; B. G. Tweedy & R. A. Kahrs, ibid., 1978, 10, 493). In drinking water, by glc with NPD (AOAC Methods, 17th Ed., 991.07) or by magnetic particle immunoassay (ibid., 995.08); dealkylated atrazine can be determined by lc with u.v. detection (ibid., 992.14).

MAMMALIAN TOXICOLOGY
IARC ref. 53, 73 class 3 Oral Acute oral LD50 for rats 1869-3090 mg tech./kg, mice >1332-3992 mg/kg. Skin and eye Acute percutaneous LD50 for rats >3100 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). Skin sensitiser in guinea pigs, but not in humans. Inhalation LC50 (4 h) for rats >5.8 mg/l air. NOEL (2 y) for rats 10 mg/kg diet (0.5 mg/kg daily), for dogs 150 mg/kg diet (3.75 mg/kg daily), for mice 10 mg/kg diet (1.4 mg/kg daily). ADI 0.005 mg/kg b.w. Water GV 2 mg/l (TDI 0.5 mg/kg b.w.). Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification Xn; R48/22| R43| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 varies from 940 mg/kg for bobwhite quail to >2000 mg/kg for mallard ducks and 4237 mg/kg for adult Japanese quail. Dietary LC50 (8 d) for Japanese quail (chicks) >5000, (adults) >1000 mg/kg. Fish LC50 (96 h) for rainbow trout 4.5-11.0, bluegill sunfish 16, carp 76, catfish 7.6, guppies 4.3 mg/l. Daphnia LC50 (48 h) 6.9 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 0.043 mg/l, (96 h) for Selenastrum capricornutum 0.13 mg/l. Other aquatic spp. Long-term studies in aquatic ecosystems indicate no permanent damage up to 0.020 mg/l. Bees LD50 (oral) >97 mg/bee; (contact) >100 mg/bee. Worms LC50 (14 d) for Eisenia foetida 78 mg/kg soil.

ENVIRONMENTAL FATE
Animals In mammals, following oral administration, atrazine is rapidly and completely metabolised, primarily by oxidative dealkylation of the amino groups (R. Ikonen et al., Toxicol. Lett., 1988, 44, 109; Bull. Environ. Contam. Toxicol., 1989, 43, 199; Y. Deng et al., J. Agric. Food Chem., 1990, 38, 1411), and by reaction of the chlorine atom with endogenous thiols. Diaminochlorotriazine is the main primary metabolite, which readily conjugates with glutathione. More than 50% of the dose is eliminated in the urine and around 33% in the faeces within 24 h. Plants In tolerant plants, atrazine is readily metabolised to hydroxyatrazine and amino acid conjugates, with further decomposition of hydroxyatrazine by degradation of the side-chains and hydrolysis of the resulting amino acids on the ring, together with evolution of CO2. In sensitive plants, unaltered atrazine accumulates, leading to chlorosis and death. Soil/Environment Major metabolites under all conditions are desethylatrazine and hydroxyatrazine. Field DT50 16-77 d (median 41 d), the longer values being from cold or dry conditions. In natural waters, DT50 10-105 d (mean 55 d). DT50 under groundwater conditions 105->200 d, depending on test system (M. J. Wood et al. in: A Walker (Ed.), Pesticides in soils and water: current perspectives (BCPC Monograph 1991, 47, 175-182)). Kd 0.2-18 ml/g, Koc 39-173 ml/g; desalkylated metabolites had values similar to those of atrazine, while hydroxyatrazine was much more strongly adsorbed.