Fungicide

FRAC  10; N-phenyl carbamate

NOMENCLATURE

Common name diethofencarb (BSI, draft E-ISO); diéthofencarb ((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 ºC  V.p. 8.4 mPa (20 ºC)  KOW logP = 3.02 (25 ºC)  Henry 8.44 ´ 10-2 Pa m3 mol-1 (calc.)  S.g./density 1.19 (23 ºC)  Solubility In water 26.6 mg/l (20 ºC). In hexane 1.3, methanol 101, xylene 30 (all in g/kg, 20 ºC).  F.p. 140 °C 

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