metam
Fungicide, nematicide, herbicide, insecticide
HRAC Z
NOMENCLATURE
metam
Common name metam (since 1990 BSI, E-ISO, F-ISO); metham (WSSA, before 1990 BSI)
IUPAC name methyldithiocarbamic acid
Chemical Abstracts name methylcarbamodithioic acid
CAS RN [144-54-7] EEC no. 205-632-2 Development codes N-869 (Stauffer)
metam-potassium
CAS RN [137-41-7]
metam-sodium
Common name metam-sodium (before 1990 E-ISO, F-ISO); karbation (USSR); carbam (JMAF - name also used for ammonium salt)
IUPAC name sodium methyldithiocarbamate
Chemical Abstracts name sodium methylcarbamodithioate
Other names SMDC CAS RN [137-42-8]; [6734-80-1] dihydrate EEC no. 205-293-0
PHYSICAL CHEMISTRY
metam
Mol. wt. 107.2 M.f. C2H5NS2
metam-potassium
Mol. wt. 145.3 M.f. C2H4KNS2 Stability Unstable when diluted.
metam-sodium
Mol. wt. 129.2 M.f. C2H4NNaS2 Form Colourless crystals (dihydrate). M.p. Decomposes without melting V.p. Non-volatile KOW logP <1 (25 ºC) Solubility In water 722 g/l (20 ºC). In acetone, ethanol, kerosene, xylene <5 g/l. Practically insoluble in most other organic solvents. Stability Stable in concentrated aqueous solution, but unstable when diluted. Decomposition is promoted by acids and heavy-metal salts. Solutions exposed to sunlight, DT50 1.6 h (pH 7, 25 ºC); on hydrolysis (25 ºC), DT50 23.8 h (pH 5), 180 h (pH 7), 45.6 h (pH 9).
COMMERCIALISATION
metam-potassium
Manufacturers Amvac
metam-sodium
History Fungicidal properties of metam-sodium reported by H. L. Klopping (Thesis, University of Utrecht, 1951) and by A. J. Overman & D. S. Burgis (Proc. Fla. St. Hortic. Soc., 1956, 69, 250). Metam-sodium introduced by Stauffer Chemical Co. (now Syngenta AG) and later by E. I. du Pont de Nemours and Co. (who no longer manufacture or market it). Patents US 2766554; US 2791605; GB 789690 all to Stauffer Manufacturers Amvac; Aragro; Buckman; Cerexagri; Lainco; Lucava; Nufarm Ltd; UCB
APPLICATIONS
metam-potassium
Uses Similar activity to metam-sodium, but has the advantage of providing potassium instead of sodium. Useful for crops that benefit from potassium, e.g. potatoes, or are sensitive to sodium, e.g. lettuce, onions, broccoli. Selected products: 'K-Pam' (Amvac)
metam-sodium
Mode of action Soil fumigant, acting by decomposition to methyl isothiocyanate (q.v.). Uses Metam-sodium is a soil sterilant, applied prior to planting out edible crops, which controls soil fungi, nematodes, weed seeds, and soil insects. Phytotoxicity Highly phytotoxic. Formulation types SL. Selected products: 'Arapam' (Aragro); 'BUSAN 1020' (Buckman); 'Lucafum' (Lucava); 'Nemasol' (UCB, UAP); 'Trimaton' (Cerexagri); 'Unifume' (Unicrop); 'Vapam' (Amvac)
OTHER PRODUCTS
metam
Discontinued products: 'VPM' * (DuPont); 'Monam' * (BASF)
metam-potassium
'Amv540' (Amvac); 'Curtin' (Amvac)
metam-sodium
'Mercenario' (UCB); 'Metacide 42' (Amvac); 'Sectagon' (Sundance, Tessenderlo Kerley); 'Sistan' (Unicrop); 'Sodam' (Papaeconomou) Discontinued products: 'Fume V Soil' * (Micro Flo)
ANALYSIS
Product analysis by Fourier transform i.r. or by hydrolysis to form carbon disulfide which is reacted and titrated with iodine (CIPAC Handbook, 1992, E, 131-133, 116-119; ibid., 1983, 1B, 1862; 1970, 1, 537). Residues in crops and soils determined by analysing them for methyl isothiocyanate by glc. Details available from Syngenta. See also R. A. Gray (Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 177; Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 717).
MAMMALIAN TOXICOLOGY
metam-sodium
Oral Acute oral LD50 for male rats 1800, female rats 1700, mice 285 mg/kg. Acute oral LD50 for rats of the methyl isothiocyanate formed in soil is 97 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 1300 mg/kg; mild irritant to eyes, corrosive to skin. Any contact with skin or organs should be treated as a burn. Inhalation LC50 (4 h) for rats >4.7 mg/l air; in 65 exposure-days trial on rats (6 h/d, 5 d/w), NOEL 0.045 mg/l air. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification Xn; R22| R31| C; R34| R43| N; R50, R53
ECOTOXICOLOGY
metam-sodium
Birds Acute oral LD50 for bobwhite quail 500 mg/kg. Dietary LC50 (5 d) for mallard ducks and Japanese quail >5000 mg/kg diet. Fish LC50 (96 h) for guppy 4.2, bluegill sunfish 0.39, rainbow trout 35.2 mg/l. Daphnia EC50 (48 h) 2.3 mg/l. Bees Non-toxic to bees when used as directed.
ENVIRONMENTAL FATE
Soil/Environment In soil, rapidly decomposes to methyl isothiocyanate, q.v.; DT50 23 min to 4 d.
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