Products >>Herbicides >> Atrazine
Atrazine
Atrazine 95%TC, Atrazine 50%SC
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)
Atrazine 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. 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 tradenames:
'AAtrex' (USA) (Syngenta); 'Aktikon' (Nitrokémia); 'Atranex'
(Makhteshim-Agan); 'Atrataf' (Rallis); 'Atratylone' (Agriphar);
'Atrazina' (Cequisa); 'Atrazol' (Sipcam); 'Coyote' (Defensa); 'Dhanuzine'
(Dhanuka); 'Fogard' (Caffaro); 'Mebazine' (Aventis); 'Sanazine'
(Sanachem); 'Surya' (Nagarjuna Agrichem); 'Triaflow' (Inquiport);
'Vectal' (Aventis); 'Zeazin S 40' (Istrochem); mixtures: 'Bicep
II Magnum' (+ benoxacor+ S-metolachlor) (Syngenta); 'Bicep II' (+
benoxacor+ metolachlor) (Syngenta); 'Bicep Magnum' (+ S-metolachlor)
(Syngenta); 'Gesaprim' (+ terbutryn) (Europe) (Syngenta); 'Marksman'
(+ dicamba) (dicamba as potassium salt) (Syngenta, BASF); 'Trinovin'
(+ amitrole+ simazine) (Efthymiadis)
Atrazine OTHER TRADENAMES
'Atradex' (Crop Care); 'Atred' (Chemiplant); 'Azoprim' (Azot); 'Cornazine'
(Papaeconomou); 'Crisazina' (Crystal); 'DG90' (Sipcam UK); 'Herpazine'
(Agrochem); 'Trac' (Atanor); 'Zeacas' (CAS) mixtures: 'Bicep' (+
metolachlor) (USA) (Syngenta); 'Clark' (+ bromoxynil) (CFPI Nufarm,
Syngenta); 'Primextra Safeneur' (+ benoxacor+ metolachlor) (Syngenta);
'Sutazine' (+ butylate) (Syngenta); 'Alazine' (+ alachlor) (Makhteshim-Agan);
'Aspect' (+ flufenacet) (Bayer); 'Aterbutex' (+ terbutryn) (Makhteshim-Agan);
'Athado Invierno' (+ terbumeton+ terbuthylazine) (Probelte); 'Atoll'
(+ isoxaflutole) (Aventis); 'Atramet Combi' (+ ametryn) (Makhteshim-Agan);
'Axiom AT' (+ flufenacet+ metribuzin) (Bayer); 'Basis Gold' (+ nicosulfuron+
rimsulfuron) (Du Pont); 'Bellater' (+ cyanazine) (BASF); 'Bullet'
(+ alachlor) (Monsanto); 'Century' (+ dimethenamid) (BASF); 'Degree
Xtra' (+ acetochlor) (with safener) (Monsanto); 'Erunit' (+ acetochlor)
(Nitrokémia); 'Extrazine II' (+ cyanazine) (Du Pont); 'Field
Master' (+ acetochlor+ glyphosate) (glyphosate as isopropylammonium
salt) (Monsanto); 'Fultime' (+ acetochlor+ dichlormid) (Dow AgroSciences);
'Guardsman' (+ dimethenamid) (BASF); 'Harness Extra' (+ acetochlor)
(Monsanto); 'Karal' (+ bromoxynil) (CFPI Nufarm); 'Laddok' (+ bentazone-sodium)
(BASF); 'Lariat' (+ alachlor) (Monsanto); 'Leadoff' (+ dimethenamid)
(Du Pont); 'Propachlor Doble' (+ alachlor) (Probelte); 'Ready Master
ATZ' (+ glyphosate) (glyphosate as isopropylammonium salt) (Monsanto);
'Shotgun' (+ 2,4-D-2-ethylhexyl) (UAP); 'Simapron Doble' (+ simazine)
(Probelte); 'Simazat' (+ simazine) (Drexel); 'Triamex' (+ simazine)
(Aventis); 'Zeazin Mix DKV' (+ prometryn) (Istrochem); 'Zeazin Mix
Extra' (+ metolachlor+ prometryn) (Istrochem) Discontinued names:
'Atratol' * (Ciba); 'Primatop' * (Ciba-Geigy); 'Cekuzina T' * (Cequisa);
'Griffex' * (Griffin); 'Hungazin' * (Budapest Chemical); 'Maizina'
* (Sipcam); 'Zeapos' * (Sagrochem) mixtures: 'Primagram' * (+ metolachlor)
(Novartis); 'Primatol' * (+ prometon) (Ciba-Geigy); 'Primextra'
* (+ benoxacor+ metolachlor) (Europe) (Novartis); 'Contour' * (+
imazethapyr-ammonium) (Cyanamid); 'Vorox(i)Granulat 371' * (+ amitrole+
sebuthylazine) (Spiess)
Atrazine ANALYSIS
Product analysis by glc with FID (CIPAC Handbook, 1980, 1A, 1106;
FAO Specification (CP/61); AOAC Methods, 1995, 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 gc with FID (AOAC Methods,
1995, 991.07); dealkylated atrazine can be determined by lc with
u.v. detection (AOAC Methods, 1995, 992.14, 10.7.01).
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.) III (Table 5); EPA (formulation) III EC hazard (Xn; R48/22|
R43| N; R50 R53)
Atrazine 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 (24 h) 87 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus
0.043 mg/l, (96 h) for Selenastrum capricornutum 0.13 mg/l. Bees
LD50 (oral) >97 mg/bee; (contact) >100 mg/bee. Worms LC50
(14 d) for Eisenia foetida 78 mg/kg soil.
Atrazine 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.