Fungicide

FRAC  3; DMI: triazole

NOMENCLATURE

diniconazole

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

IUPAC name (E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 

Chemical Abstracts name (E)-(?-b-[(2,4-dichlorophenyl)methylene]-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol 

CAS RN [83657-24-3]; [76714-88-0] (E)- isomers  Development codes S-3308 L (Sumitomo); XE-779 (Chevron) 

diniconazole-M

IUPAC name (E)-(R)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 

CAS RN [83657-18-5]; [83657-19-6] (E)-(S)- isomer 

PHYSICAL CHEMISTRY

diniconazole

Mol. wt. 326.2  M.f. C15H17Cl2N3O  Form Colourless crystals.  M.p. c. 134-156 ºC  V.p. 2.93 mPa (20 ºC); 4.9 mPa (25 ºC)  KOW logP = 4.3 (25 ºC)  S.g./density 1.32 (20 ºC)  Solubility In water 4 mg/l (25 ºC). In acetone, methanol 95, xylene 14, hexane 0.7 (all in g/kg, 25 ºC).  Stability Stable to heat, light, and moisture. 

COMMERCIALISATION

History Fungicide reported by H. Takano et al. (Noyaku Kagaku, 1983, 8, 575); diniconazole-M is more potent than diniconazole. Introduced by Sumitomo Chemical Co., Ltd and Valent. 

diniconazole

Patents US 4203995; GB 2004276  Manufacturers Sumitomo

diniconazole-M

Patents US 4435203; EP 54431  Manufacturers Sumitomo

APPLICATIONS

Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor.  Mode of action Systemic fungicide with protective and curative action.  Uses Control of leaf and ear diseases (e.g. powdery mildew, Septoria, Fusarium, smuts, bunt, rusts, scab, etc.) in cereals; powdery mildew in vines; powdery mildew, rust, and black spot in roses; leaf spot in peanuts; Sigatoka disease in bananas; and Uredinales in coffee. Also used on fruit, vegetables, and other ornamentals.  Formulation types EC; SC; WG; WP.  Selected tradenames: 'Spotless' (Sumitomo); 'Sumi-8' (Sumitomo)

OTHER TRADENAMES

diniconazole

'Dinizol' (AgroSan); 'Embassador' (Sanonda)

ANALYSIS

Product analysis details available from Sumitomo Chemical Co., Ltd. Residues determined by glc with FTD. 

MAMMALIAN TOXICOLOGY

diniconazole

Oral Acute oral LD50 for male rats 639, female rats 474 mg/kg.  Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Mild eye irritant; non-irritating to skin (rabbits). Not a skin sensitiser (guinea pigs).  Inhalation LC50 (4 h) for rats >2770 mg/m3.  Toxicity class WHO (a.i.) III; EPA (formulation) III  EC hazard Xn; R22| N; R50, R53 ((E)- isomers) 

ECOTOXICOLOGY

diniconazole

Birds Acute oral LD50 for bobwhite quail 1490, mallard ducks >2000 mg/kg. Dietary LC50 (8 d) for mallard ducks 5075 mg/kg diet.  Fish LC50 (96 h) for rainbow trout 1.58, Japanese killifish 6.84, carp 4.0 mg/l.  Bees Acute contact LD50 for bees >20 mg/bee. 

ENVIRONMENTAL FATE