1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea
2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide
C7H10N4O3
Colourless, odourless crystals; (tech. is a peach colour)
160-161oC; (tech., 159-160oC)
0.15 mPa (20oC)
1.32 (25oC)
In water 890 mg/kg (pH 5, 20oC). In hexane 0.037, toluene 5.29, acetonitrile 57, ethyl acetate 28, n-octanol 1.43, methanol 22.9, acetone 62.4, dichloromethane 133.0 (all in g/l, 20oC).
Hydrolysis DT50 148 d (pH 5), 34 h (pH 7), 31 min (pH 9). Aqueous photolysis DT50 1.8 d (pH 5).
3.8×10-5 (pH 7), 3.3 ?10-5 (pH 5) (both Pa m3 mol-1, calc.)
0.59 (pH 5), 0.67
9.7 (decomp.)
Foliar fungicide with protective and curative action. Has contact and local systemic activity, and also inhibits sporulation.
Control of Peronosporales, especially Peronospora, Phytophthora, and Plasmopara spp. Normally used in combination with protectant fungicides (to improve residual activity) on a range of crops, including vines, hops, potatoes, and tomatoes.
Incompatible with alkaline materials.
Acute oral LD50 for male rats 760, female rats 1200 mg/kg.
Acute percutaneous LD50 for rabbits >2000 mg/kg. Not an eye irritant; slight skin irritant (rabbits). Not a skin sensitiser (guinea pigs).
LC50 (4 h) for male and female rats >5.06 mg/l.
(2 y) for male rats 4.1, female rats 5.4, male mice 4.2, female mice 5.8, male and female dogs 3.0 mg/kg b.w. daily.
0.013 mg/kg.
WHO (a.i.) III; EPA (formulation) III
Xn; R22| R43| N; R50, R53
Acute oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >5620 mg/kg diet.
LC50 (96 h) for rainbow trout 61, bluegill sunfish 29, common carp 91, sheepshead minnow >47.5 mg/l.
LC50 (48 h) 27 mg/l.
EC50 (5 d) for Selenastrum capricornutum 1.21 mg/l; EC50 for Anabaena flos-aquae 231 ppb.
LC50 (14 d) >2208 mg/kg soil.
Degraded to glycine with subsequent incorporation into natural products (proteins and starch).
In rats, cymoxanil was readily absorbed through the intestines; the majority of the dose was excreted in the urine. The proposed metabolic pathway involves hydrolysis of cymoxanil and then degradation to glycine.
In lab. soils, DT50 0.75-1.6 d (5 soils, pH range 5.7-7.8, o.m. 0.8-3.5%). In the field, DT50 (bare soil) 0.9-9 d. In aquatic studies, DT50 <1 d. Koc 38-237. Cymoxanil is mobile, adsorption Freundlich K 0.29 to 2.86 in four soil types.
Product analysis by hplc.