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Metamitron

Metamitron 98%TC
Metamitron 70%WG
Metamitron 70%WP
Metamitron 70%SC

Herbicide
HRAC C1 WSSA 5; 1,2,4-triazinone

Metamitron NOMENCLATURE
Common name metamitron (BSI, E-ISO); métamitrone ((f) F-ISO); methiamitron (Belgium)
IUPAC name 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one
Chemical Abstracts name 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one
CAS RN [41394-05-2] EEC no. 255-349-3 Development codes BAY DRW 1139; BAY 134028 (Bayer)

Metamitron PHYSICAL CHEMISTRY
Mol. wt. 202.2 M.f. C10H10N4O Form Colourless, odourless crystals. M.p. 166.6 ºC V.p. 8.6 10-4 mPa (20 ºC); 2 10-3 mPa (25 ºC) KOW logP = 0.83 Henry 1  10-7 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.35 g/cm3 (22.5 ºC) Solubility In water 1.7 g/l (20 ºC). In dichloromethane 30-50, cyclohexanone 10-50, isopropanol 5.7, toluene 2.8, hexane <0.1, methanol 23, ethanol 1.1, chloroform 29 (all in g/l, 20 ºC). Stability Very stable in acidic media; decomposed by strong alkalis (pH >10); DT50 (22 ºC) 410 d (pH 4), 740 h (pH 7), 230 h (pH 9). Photodecomposition on soil surfaces is very rapid, and extremely rapid in water.

COMMERCIALISATION
History Herbicide reported by R. R. Schmidt et al. (3rd Int. Meeting Selective Weed Control in Beet, 1975, 1, 713) and H. Hack (ibid., p. 729) and reviewed by H. Lembrich (Pflanzenschutz-Nachr. (Engl. Ed.), 1978, 31, 197). Introduced in France (1975) by Bayer AG. Divested to Quena Plant Protection N.V. (a member of the Makhteshim-Agan Group) in 2002. Patents BE 799854; GB 1368416 Manufacturers Aimco; Feinchemie Schwebda; Makhteshim-Agan; Sharda

Metamitron APPLICATIONS
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor site. Mode of action Selective systemic herbicide, absorbed predominantly by the roots, but also by the leaves, with translocation acropetally. Uses Used against grass and broad-leaved weeds in sugar and fodder beets. Applied pre-drilling incorporated, pre- and post-emergence (post-emergence as sequential treatment tank-mixed with oil or other herbicides). Also used in mangold, red beet and certain strawberry varieties. Rates 0.35-4.2 kg/ha for all crops. Phytotoxicity High selectivity in sugar and fodder beet. Formulation types SC; WG; WP. Compatibility Compatible with other beet herbicides. Selected products: 'Goltix' (Makhteshim-Agan); 'Bietomix' (Agrimix); 'Homer' (Griffin); 'Martell' (Griffin); 'Mito' (Cequisa); 'MM70' (Gharda); 'Seismic' (Barclay); 'Singapore' (Rocca); 'Tornado' (Feinchemie Schwebda)