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Prometryn

Prometryn 95%TC
Prometryn 50%SC

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

Prometryn NOMENCLATURE
Common name prometryn (BSI from 1984, E-ISO, ANSI, WSSA); prometryne ((f) F-ISO, JMAF and, until 1984, BSI)
IUPAC name N2,N4-di-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N,N'-bis(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine
CAS RN [7287-19-6] EEC no. 230-711-3 Development codes G 34 161 (Geigy)

Prometryn PHYSICAL CHEMISTRY
Composition Tech. is 97% pure. Mol. wt. 241.4 M.f. C10H19N5S Form White powder. M.p. 118-120 ºC B.p. >300 °C/100 kPa V.p. 0.165 mPa (25 ºC) (OECD 104) KOW logP = 3.1 (25 ºC, unionised) Henry 1.2  10-3 Pa m3 mol-1 (calc.) S.g./density 1.15 (20 ºC) Solubility In water 33 mg/l (25 ºC). In acetone 300, ethanol 140, hexane 6.3, toluene 200, n-octanol 110 (all in g/l, 25 ºC). Stability Stable to hydrolysis at 20 ºC in neutral, slightly acidic or slightly alkaline media. Hydrolysed by warm acids and alkalis. Decomposed by u.v. irradiation. pKa 4.1, weak base

COMMERCIALISATION
History Herbicide reported by H. Gysin (Chem. Ind. (London), 1962, p. 1393). Introduced by J. R. Geigy S.A. (now Syngenta AG). Patents CH 337019; GB 814948 Manufacturers Griffin; Makhteshim-Agan; Syngenta

Prometryn APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Also inhibits oxidative phosphorylation. Mode of action Selective systemic herbicide, absorbed by the leaves and roots, with translocation acropetally through the xylem from the roots and foliage, and accumulation in the apical meristems. Uses Used pre-emergence, at 0.8-2.5 kg/ha, in cotton, sunflowers, peanuts, potatoes, carrots, peas and beans; post-emergence, at 0.8-1.5 kg/ha, in cotton, potatoes, carrots, celery and leeks. Phytotoxicity Used as a directed spray on cotton while young, to avoid foliar injury. Formulation types FW; SC; WP. Selected products: 'Caparol' (USA) (Syngenta); 'Gesagard' (Syngenta); 'Cotton-Pro' (Griffin); 'Efmetryn' (Efthymiadis); 'Prometrex' (Makhteshim-Agan); mixtures: 'Cotralin' (+ alachlor) (Efthymiadis); 'Cottonex Pro' (+ fluometuron) (Aragro)