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HRAC C1 WSSA 5 1,3,5-triazine

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] EC no. 217–617–8 Development codes G 30 027 (Geigy) Smiles code CCNc1nc(Cl)nc(NC(C)C)n1
Composition Tech. is ≥96% pure. Mol. wt. 215.7 M.f. C8H14ClN5 Form Colourless powder. M.p. 175.8 °C B.p. 205.0 °C/101 kPa V.p. 3.85 × 10-2 mPa (25 °C) (OECD 104) Kow logP = 2.5 (25 °C) 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 °C). 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 °C). 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 °C in neutral media; DT50 (pH 1) 9.5, (pH 5) 86, (pH 13) 5.0 d. pKa 1.6, v. weak base
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 Syngenta; Agrochem; Atanor; Binnong; Changxing First; Zhejiang Zhongshan; Crystal; Dalian Raiser; Dow AgroSciences; Drexel; DuPont; Hegang Heyou; AGROFINA; Jiangsu Lulilai; KSA; Makhteshim-Agan; Nagarjuna Agrichem; Nortox; Oxon; Rainbow; Rallis; Shandong Qiaochang; ShardaZhong-Xi
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, and 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 (Syngenta) ; Atranex (Makhteshim-Agan) ; Atraplex (Ingeniería Industrial) ; Atrataf (Rallis) ; Atratylone (Agriphar) ; Atrazila (Baocheng) ; Atrazol (Sipcam S.p.A.) ; 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) (Syngenta) ; Bicep Magnum (USA) (+S-metolachlor) (Syngenta) ; Gesaprim combi (Europe) (+terbutryn) (Syngenta) ; Keystone (+dichlormid +acetochlor) (Dow AgroSciences) ; Lexar (USA) (+benoxacor +S-metolachlor +mesotrione) (Syngenta) ; Lumax (USA, Mexico) (+mesotrione +S-metolachlor +benoxacor) (Syngenta) ; Marksman (+dicamba-potassium) (BASF, ;Syngenta) ; Primextra Gold (USA, Mexico) (+S-metolachlor) (Syngenta) ; Stalwart Xtra (+metolachlor) (Sipcam USA) ; Callisto Xtra (+mesotrione) (Syngenta) Other products Agri-atrazina (Cequisa) ; Atra-5 (Drexel) ; Atradex (Crop Care) ; Atraflo (Plaaskem S.A.) ; Atred (Chemiplant) ; Auguzine (Drexel) ; Azinotox (Pyosa) ; Azoprim (Azot) ; Conifer 90 (Loveland, ;UAP) ; Cornazine (Papaeconomou) ; Crisazina (Crystal) ; DG90 (Sipcam UK) ; Fezprim (Zagro) ; Fogard (Isagro) ; Gladezine (Marman) ; Herpazine (Agrochem) ; Maizine (Zagro) ; Manch (Crop Health) ; Mebazine (Bayer CropScience) ; Nu-trazine (Nufarm Ltd) ; Primoleo (Syngenta) ; Radazin T-50 (Herbos) ; Rasayanzine (Krishi Rasayan) ; Siptran (Sipcam Agro) ; Solaro (P I Industries) ; Tiracide (Efal) ; Trac (Atanor) ; Vectal (Bayer CropScience) ; Zeacas (CAS) ; Zuellig Pre (Zagro) mixtures Alazine (+alachlor) (Makhteshim-Agan) ; Anibal (+diuron) (Aragro) ; Aracloro Super (+alachlor) (Aragro) ; 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) ; Atrasimex (+simazine) (Makhteshim-Agan) ; Basis Gold (+rimsulfuron +nicosulfuron) (DuPont) ; Bellater (+cyanazine) (Feinchemie Schwebda) ; Bifone (+alachlor) (Sipcam Inagra) ; Brox-AT (+bromoxynil octanoate) (Albaugh) ; Brozine (+bromoxynil octanoate) (Loveland, ;UAP) ; Bullet (+alachlor) (Monsanto) ; Calibre (+acetochlor +terbuthylazine) (Plaaskem S.A.) ; Century (+dimethenamid) (BASF) ; Charger Max (+S-metolachlor) (Winfield Solutions) ; Cinch ATZ (USA) (+S-metolachlor) (DuPont) ; Confidence Extra (+acetochlor) (Monsanto, ;Winfield Solutions) ; Degree Xtra (+furilazole +acetochlor) (Monsanto) ; Dicambazine (+dicamba-potassium) (Albaugh) ; Double Team (+acetochlor) (Makhteshim-Agan) ; Extrazin (+simazine) (Sipcam Agro) ; Field Master (+acetochlor +glyphosate-isopropylammonium) (Monsanto) ; Fogart (+simazine) (Makhteshim-Agan) ; FulTime (+acetochlor +dichlormid) (Dow AgroSciences) ; Gardomil Gold (+terbuthylazine +S-metolachlor) (Syngenta) ; G-Max Lite (+dimethenamid-P) (BASF) ; Guardsman (+dimethenamid) (BASF) ; Guardsman Max (+dimethenamid-P) (BASF) ; Harness Xtra (+acetochlor) (Monsanto) ; Laddok (+bentazone-sodium) (BASF, ;Sipcam USA) ; Lariat (+alachlor) (Monsanto) ; Leadoff (+dimethenamid) (DuPont) ; Liberty ATZ (+glufosinate-ammonium) (Bayer CropScience) ; Merlin Extra (+isoxaflutole) (Bayer CropScience) ; Merlin Mix (+isoxaflutole) (Bayer CropScience) ; Parallel Plus (+benoxacor +metolachlor) (Makhteshim-Agan) ; Primatop (+simazine) (Syngenta) ; Propachlor Doble (+alachlor) (Probelte) ; Rifle Plus (+dicamba-potassium) (Loveland, ;UAP) ; Shotgun (+2,4-D-2-ethylhexyl) (Loveland, ;UAP) ; Simapron Doble (+simazine) (Probelte) ; Simazat (+simazine) (Drexel) ; Steadfast ATZ (+nicosulfuron +rimsulfuron) (DuPont) ; Sterling Plus (+dicamba-potassium) (BASF, ;Winfield Solutions) ; Suprazine (+terbuthylazine) (Makhteshim-Agan) ; Terbuzin (+terbuthylazine) (Plaaskem S.A.) ; Top Plus (+alachlor) (IQV) ; Tramex Combi (+ametryn) (Zagro) ; Triamex (+simazine) (Bayer CropScience) ; Trizmet (+metolachlor) (Drexel) ; Zuellig Combi (+ametryn) (Zagro) Discontinued products Aktikon * (Nitrokémia) ; Atratol * (Ciba) ; Atrazina * (Cequisa) ; Cekuzina T * (Cequisa) ; Gésaprime * (Syngenta) ; Griffex * (Griffin) ; Hungazin * (Budapest Chemical) ; Maizina * (Sipcam S.p.A.) ; Weedex Liquid * (Syngenta) ; Zeapos * (Sagrochem) mixtures A-11976E * (+glyphosate-isopropylammonium) (Syngenta) ; Amexine * (+butralin) (CFPI) ; Aspect * (+flufenacet) (Bayer CropScience) ; Axiom AT * (+metribuzin +flufenacet) (Bayer CropScience) ; Barko * (+metosulam) (Dow AgroSciences) ; Bicep * (USA) (+metolachlor) (Syngenta) ; Bicep II * (+benoxacor +metolachlor) (Syngenta) ; Bicep Magnum TR * (+S-metolachlor +flumetsulam) (Syngenta) ; Clark * (+bromoxynil octanoate) (Nufarm SAS) ; Contour * (+imazethapyr-ammonium) (BASF) ; Erunit * (+AD 67 +acetochlor) (Nitrokémia) ; Gesaprim * (Europe) (+terbutryn) (Syngenta) ; Karal * (+bromoxynil) (Nufarm SAS) ; Metto * (+metosulam) (Bayer CropScience, ;Dow AgroSciences) ; Primagram * (+metolachlor) (Novartis) ; Primatol * (+prometon) (Ciba-Geigy) ; Primextra * (Europe) (+benoxacor +metolachlor) (Novartis) ; Primextra * (+S-metolachlor) (Syngenta) ; Primextra II Magnum * (+benoxacor +S-metolachlor) (Syngenta) ; Primextra Safeneur * (+benoxacor +metolachlor) (Syngenta) ; Ready Master ATZ * (+glyphosate-isopropylammonium) (Monsanto) ; Sabrine * (+bromoxynil) (Nufarm SAS) ; Surpass 100 * (+dichlormid +acetochlor) (Dow AgroSciences) ; Sutazine * (+butylate) (Syngenta) ; Trinovin * (+simazine +amitrole) (Efthymiadis) ; Vorox(i)Granulat 371 * (+amitrole +sebuthylazine) (Spiess) ; Zeazin Mix Extra * (+prometryn +metolachlor) (Istrochem)
Product analysis by glc with FID (CIPAC Handbook, 1998, H, 33; FAO Specification (CP/61); AOAC Methods, 18th 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) or by super-critical CO2 extraction and gc/ms determination (AOAC Methods, 18th Ed., 2002.03). See also Pestic. Anal. Man., I, 302; ibid., II, 180.220. In drinking water by glc with NPD (AOAC Methods, 18th Ed., 991.07), by magnetic particle immunoassay (ibid., 995.08), by gc/ms (Environ. Chem. Methods), or by lc/ms/ms (ibid.); dealkylated atrazine can be determined by lc with uv detection (AOAC Methods, 18th Ed., 992.14).
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 hours. 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. Soli/Environment Major metabolites under all conditions are desethylatrazine and hydroxyatrazine. Field DT50 16–117 d (median 58 d), the longer values being from cold or dry conditions. In natural waters, DT50 14–105 d (mean 55 d). DT50 under groundwater conditions 105–>200 d, depending on test system (M. J. Wood et al. (1991) In: A Walker (ed.), Pesticides in soils and water: current perspectives, BCPC Monograph no. 47, pp. 175–182). Kd 0.2–18 ml/g, Koc 39–173 ml/g; desalkylated metabolites had values similar to those of atrazine (Kd 0.2–8.6 ml/g) whereas hydroxyatrazine (Kd 1.6–390) was much more strongly adsorbed.
JMPR Mtg. 109 (2007). JMPR Evaln. II 112 (2007). HSG 47 (1990). PDS 82 (1996). ICSC 0099 (1994); EU Rev. Rep. SANCO/10496/2003 (2003). IARC 91/414/EC Annex 1 status Not included, 2004/248/EC.
IARC 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. Non-irritating to skin; minimally irritating to eyes (rabbits). Not a skin sensitiser in guinea pigs, nor in humans. Inhalation LC50 (4 h) for rats >5.8 mg/l air. NOEL (2 y) for rats 70 ppm (3.5 mg/kg daily), for dogs 150 mg/kg diet (5.0 mg/kg daily), for mice 10 mg/kg diet (1.4 mg/kg daily). ADI (EPA) aRfD 0.1, cRfD 0.018 mg/kg b.w. [2003]; (EPA) cRfD for hydroxytriazine metabolite 0.01 mg/kg b.w. [2003]. Toxicity class WHO (a.i.) U EPA (formulation) III EC classification Xn; R48/22| R43| N; R50, R53
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) for D. magna 29, for Ceriodaphna dubia 4.9 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 0.043 mg/l, (96 h) for Selenastrum capricornutum 0.01 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 μg/bee; (contact) >100 μg/bee. Worms LC50 (14 d) for Eisenia foetida 78 mg/kg soil. Other beneficial spp. No effect on ground beetles at 1.5 kg/ha.

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