diethofencarb (239)
Fungicide
FRAC 10; N-phenyl carbamate
NOMENCLATURE
Common name diethofencarb (BSI, draft E-ISO); di閠hofencarb ((m) draft F-ISO)
IUPAC name isopropyl 3,4-diethoxycarbanilate
Chemical Abstracts name 1-methylethyl (3,4-diethoxyphenyl)carbamate
CAS RN [87130-20-9] Development codes S-1605 (Sumitomo)
PHYSICAL CHEMISTRY
Mol. wt. 267.3 M.f. C14H21NO4 Form White, crystalline solid; (tech. is a colourless to light brown solid). M.p. 100.3 篊 V.p. 8.4 mPa (20 篊) KOW logP = 3.02 (25 篊) Henry 8.44 ?10-2 Pa m3 mol-1 (calc.) S.g./density 1.19 (23 篊) Solubility In water 26.6 mg/l (20 篊). In hexane 1.3, methanol 101, xylene 30 (all in g/kg, 20 篊). F.p. 140 癈
COMMERCIALISATION
History Fungicide introduced by Sumitomo Chemical Co., Ltd. Patents EP 78663 Manufacturers Sumitomo
APPLICATIONS
Mode of action Systemic fungicide with protective and curative action. Readily absorbed though the leaves and roots, and translocated throughout the plant. Inhibits mitosis in grey mould germ tubes. Uses Control of benzimidazole-resistant strains of Botrytis spp. on vines, cucumbers, aubergines, tomatoes, strawberries, citrus fruit, lettuce, onions, and beans. Has secondary activity against powdery mildews (Cercospora, Venturia). Formulation types WP. Selected tradenames: 'Sumico' (Sumitomo)
OTHER TRADENAMES
Mixtures: 'Getter' (+ thiophanate-methyl) (Sumitomo); 'Sumiblend' (+ procymidone) (Agros, Sumitomo); 'Jonk' (+ carbendazim) (Philagro); 'Sumico' (+ carbendazim) (Syngenta)
ANALYSIS
Product analysis details available from Sumitomo Chemical Co., Ltd. Residues determined by glc with FTD.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Inhalation LC50 (4 h) for rats >1050 mg/m3. Other Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) III (Table 5)
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2250 mg/kg. Fish LC50 (96 h) for rainbow trout >18 mg/l. Daphnia LC50 (3 h) for D. pulex >10 mg/l. Bees Contact LC50 20 mg/bee.
ENVIRONMENTAL FATE
Animals After oral administration of 14C-diethofencarb to rats, 98.5-100 % of 14C was excreted within 7 days. The major metabolic routes in the rat were de-ethylation of the 4-ethoxy group, cleavage of the carbamate linkage, acetylation and finally formation of the glucuronide and sulfate conjugates (J. Pestic. Sci., 1990, 15, 395). Plants Readily degraded in plants. Soil/Environment Readily degraded in soil; DT50 <1-6 d under aerobic conditions; only very slightly degraded under anaerobic sterilised conditions.