ferimzone
Fungicide
FRAC 29, C5
NOMENCLATURE
Common name ferimzone (BSI, draft E-ISO)
IUPAC name (Z)-2'-methylacetophenone 4,6-dimethylpyrimidin-2-ylhydrazone
Chemical Abstracts name (Z)-4,6-dimethyl-2(1H)-pyrimidinone [1-(2-methylphenyl)ethylidene]hydrazone
CAS RN [89269-64-7] Development codes TF-164 (Takeda)
PHYSICAL CHEMISTRY
Mol. wt. 254.3 M.f. C15H18N4 Form Colourless crystals. M.p. 175-176 ºC V.p. 4.11 ´ 10-3 mPa (20 ºC) KOW logP = 2.89 (25 ºC) Henry 6.45 ´ 10-6 Pa m3 mol-1 (calc.) S.g./density 1.185 Solubility In water 162 mg/l (30 ºC). Soluble in ethanol, ethyl acetate, chloroform, xylene, and acetonitrile. Stability Stable to sunlight. Stable in neutral and alkaline aqueous solutions.
COMMERCIALISATION
History Fungicide introduced by Takeda Chemical Industries Ltd (now Sumitomo Chemical Takeda Agro Company Ltd) and first marketed in Japan in 1992. Manufacturers Sumitomo Chemical Takeda
APPLICATIONS
Biochemistry Uncouples oxidative phosphorylation. Uses Control of Helminthosporium oryzae, Cercospora oryzae, and Pyricularia oryzae in rice. Applied at 600-800 g/ha (DL formulation) or 125 g/ha (SC). Formulation types DL; SC; WP. Selected products: mixtures: 'Blasin' (+ phthalide) (Sumitomo Chemical Takeda)
OTHER PRODUCTS
Mixtures: 'Hustler' (+ phthalide+ validamycin+ cartap hydrochloride+ clothianidin) (Sumitomo Chemical Takeda)
ANALYSIS
Product and residue analysis by hplc.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 725, female rats 642, male mice 590, female mice 542 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Inhalation LC50 (4 h) for rats >3.8 mg/l. Toxicity class WHO (a.i.) III
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250, mallard ducks >292 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5620 ppm. Fish LC50 (96 h) for carp 20 mg/l. Daphnia EC50 (48 h) 6.2 mg/l. Algae EbC50 (72 h) for Selenastrum 4.4 mg/l. Other aquatic spp. LC50 (24 h) for Moina macrocopa >40 mg/l. Bees LD50 (oral) >140 mg/bee.
ENVIRONMENTAL FATE
Soil/Environment DT50 3-14 d, depending on soil type.
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