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Dimethenamid

Dimethenamid 95%TC
Dimethenamid 90%EC

Herbicide
HRAC K3 WSSA 15; chloroacetamide

NOMENCLATURE
dimethenamid
Common name dimethenamid (BSI, pa E-ISO)
IUPAC name (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
Chemical Abstracts name (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
CAS RN [87674-68-8] Development codes SAN 582 H (Sandoz)

dimethenamid-P
Common name dimethenamid-P (BSI, pa E-ISO)
IUPAC name (S)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
Chemical Abstracts name 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-((1S)-2-methoxy-1-methylethyl)acetamide
Other names s-dimethenamid CAS RN [163515-14-8] Development codes BAS 656H (BASF); SAN 1289H (Sandoz)

PHYSICAL CHEMISTRY
dimethenamid
Mol. wt. 275.8 M.f. C12H18ClNO2S Form Yellowish-brown, viscous liquid. B.p. 127 ºC/26.7 Pa V.p. 36.7 mPa (25 ºC) KOW logP = 2.15?.02 (25 ºC) Henry 8.32  10-3 Pa m3 mol-1 S.g./density 1.187 (25 ºC) Solubility In water 1.2 g/l (pH 7, 25 ºC). In heptane 282, iso-octane 220 (both in g/kg, 25 ºC). In ether, kerosene, ethanol all >50% (25 ºC). Stability Stable in storage at 54 ºC for 4 weeks, and at 70 ºC for 2 weeks. Estimated decomposition at 20 ºC within 2 years is <5%. Stable at pH 5-9 (buffered, 25 ºC) for 30 d. F.p. 91 °C (Pensky-Martens closed cup)

dimethenamid-P
Mol. wt. 275.8 M.f. C12H18ClNO2S Form Yellow-brown clear liquid. B.p. 122.6 °C/0.07 mmHg V.p. 2.51 mPa (25 °C) KOW logP = 1.89 (25 °C) Henry 4.80  10-4 Pa m3 mol-1 S.g./density 1.195 (25 °C) Solubility In water 1449 mg/l (25 °C). In hexane 20.8 g/100ml; miscible with acetone, acetonitrile, toluene, and n-octanol (25 °C). Stability Stable to hydrolysis at pH 5, 7, and 9 for 31 d (25 °C). F.p. 79 °C

COMMERCIALISATION
dimethenamid
History Reported by J. Harr et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1991, 1, 87). Introduced by Sandoz AG (became Novartis Crop Protection AG); sold to BASF in 1996. Manufacturers BASF

dimethenamid-P
History BASF introduced the resolved (S)- isomer in 2000. Manufacturers BASF

Dimethenamid APPLICATIONS
Biochemistry Inhibits cell division and tissue differentiation. Chloroacetamides may inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr. Meeting WSSA, Toronto, 40, 117-118, 2000; P. Böger, Abstr. III Int. Weed Control Congr., Brazil 2000). Maize tolerance of chloroacetamides is due mainly to conjugation with glutathione; P450 metabolism may also be a factor. Mode of action Primarily a soil-applied herbicide but also can be applied post-emergence. The herbicide enters the plant via root and epicotyl uptake; there is little or no foliar activity, and little translocation in the plant. Uses Control of annual grass and broad-leaved weeds pre- or early post- emergence, in maize, soya beans, sugar beet, potatoes, dry beans, and other crops. Applied at 0.85 - 1.44 kg/ha (dimethenamid), 0.65-1.0 kg/ha (dimethanimid-P). Formulation types EC.

dimethenamid
Selected products: 'Frontier' (BASF) Formulation types EC.

dimethenamid-P
Selected products: 'Frontier X2' (BASF); 'Isard' (BASF); 'Outlook' (BASF); 'Spectrum' (BASF)