Fungicide

FRAC  X

NOMENCLATURE

Common name cymoxanil (BSI, ANSI, draft E-ISO, (m) draft F-ISO)

IUPAC name 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea 

Chemical Abstracts name 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide  

CAS RN [57966-95-7]  EEC no. 261-043-0  Development codes DPX-T3217 (Du Pont) 

PHYSICAL CHEMISTRY

Composition Tech. is >95%.  Mol. wt. 198.2  M.f. C7H10N4O3  Form Colourless, odourless crystals; (tech. is a peach colour).  M.p. 160-161 ºC; (tech., 159-160 °C)  V.p. 0.15 mPa (20 °C)  KOW logP = 0.59 (pH 5), 0.67 (pH 7)  Henry 3.8 ´ 10-5 (pH 7), 3.3 ´ 10-5 (pH 5) (both Pa m3 mol-1, calc.)  S.g./density 1.31 (25 ºC)  Solubility In water 890 mg/kg (pH 5, 20 ºC). In hexane 1.85, toluene 5.29, acetonitrile 57, ethyl acetate 28, n-octanol 1.43, methanol 22.9, acetone 62.4, methylene chloride 133.0 (all in g/l, 20 ºC).  Stability Hydrolysis DT50 148 d (pH 5), 34 h (pH 7), 31 min (pH 9). Aqueous photolysis DT50 1.8 d (pH 5).  pKa 9.7 (decomp.) 

COMMERCIALISATION

History Fungicide reported by J. M. Serres & G. A. Carraro (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1976. 41, 645). Introduced by E. I. du Pont de Nemours Co.; first marketed in mid 1970s.  Patents US 3957847  Manufacturers Du Pont; Griffin; Oxon

APPLICATIONS

Mode of action Foliar fungicide with protective and curative action. Has contact and local systemic activity, and also inhibits sporulation.  Uses 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.  Formulation types WP.  Compatibility Incompatible with alkaline materials.  Selected tradenames: 'Curzate' (Du Pont); 'Asco' (Agrimix); mixtures: 'Aktuan' (+ dithianon) (BASF); 'Fobeci' (+ benalaxyl+ folpet) (Sipcam Inagra); 'Manex C-8' (+ mancozeb) (Griffin); 'Micexanil' (+ mancozeb) (Sipcam); 'Pulsan' (+ mancozeb+ oxadixyl) (Syngenta); 'Quadris' (+ azoxystrobin) (Syngenta); 'Sygan PM' (+ folpet+ mancozeb) (Griffin); 'Syphal PM' (+ copper oxychloride+ folpet+ mancozeb) (Griffin)

OTHER TRADENAMES

'Cimoxpron' (Probelte); 'Sarman' (Sipcam Phyteurop); 'Texas' (Rocca); 'Vitene' (Sipcam); 'Zetanil' (Sipcam) mixtures: 'Copral' (+ copper sulfate) (Du Pont); 'Equation Pro' (+ famoxadone) (Du Pont); 'Sirdate S' (+ folpet+ oxadixyl) (Du Pont); 'Sygan LS' (+ folpet+ mancozeb) (Du Pont); 'Sygan S' (+ folpet) (Du Pont); 'Syphal LS' (+ copper oxychloride+ folpet+ mancozeb) (Du Pont); 'Apron Elite' (+ carbendazim+ oxadixyl+ thiram) (Syngenta); 'Ashlade Solace' (+ mancozeb) (Ashlade); 'Aviso Cup' (+ copper oxychloride+ metiram) (BASF); 'Curtine-V' (+ mancozeb) (Vapco); 'Cymotine' (+ mancozeb) (Agro Chemicals); 'Eclair' (+ trifloxystrobin) (Bayer); 'Horizon' (+ famoxadone) (Du Pont, Nissan); 'Kupfer Fusilan' (+ copper oxychloride) (Kwizda); 'Manoxil' (+ mancozeb) (AgroSan); 'Ripost Pepite' (+ mancozeb+ oxadixyl) (Syngenta); 'Sirdate P' (+ maneb+ oxadixyl) (Griffin); 'Valiant' (+ folpet+ fosetyl-aluminium) (Aventis); 'WAKIL XL' (+ fludioxonil+ metalaxyl-M) (Syngenta) Discontinued names mixtures: 'Besiege WSB' * (+ mancozeb) (Du Pont); 'Systol M' * (+ mancozeb) (Du Pont); 'Trustan' * (+ mancozeb+ oxadixyl) (Du Pont)

ANALYSIS

Product analysis by hplc. Residues determined by glc. Details available from Du Pont. 

MAMMALIAN TOXICOLOGY

Oral Acute oral LD50 for male and female rats 960 mg/kg.  Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not an eye irritant; slight skin irritant (rabbits). Not a skin sensitiser (guinea pigs).  Inhalation LC50 (4 h) for male and female rats >5.06 mg/l.  NOEL (2 y) for male rats 4.1, female rats 5.4, male mice 4.2, female mice 5.8, male dogs 3.0, female dogs 1.6 mg/kg b.w. daily.  ADI 0.016 mg/kg.  Toxicity class WHO (a.i.) III; EPA (formulation) III  EC hazard Xn; R22| R43| N; R50, R53 

ECOTOXICOLOGY

Birds 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.  Fish LC50 (96 h) for rainbow trout 61, bluegill sunfish 29, common carp 91, sheepshead minnow >47.5 mg/l.  Daphnia LC50 (48 h) 27 mg/l.  Algae 23% Inhibition of Selenastrum capricornutum at 1.05 mg/l after 5 d; EC50 for Anabaena flos-aquae 231 ppb.  Other aquatic spp. LC50 (96 h) for Eastern oyster >46.9, mysid shrimp >44.4 ppm.  Bees Not toxic to bees; LD50 (48 h, contact) >25 mg/bee; LC50 (48 h, oral) >1000 ppm.  Worms LC50 (14 d) >2208 mg/kg soil. 

ENVIRONMENTAL FATE