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clodinafop-propargyl
Herbicide
HRAC A WSSA 1; aryloxyphenoxypropionate
NOMENCLATURE
clodinafop-propargyl
Common name clodinafop-propargyl
IUPAC name prop-2-ynyl (R)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate
Chemical Abstracts name propynyl (R)-2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoate
CAS RN [105512-06-9]; [105511-96-4] racemate Development codes CGA 184927 (Ciba-Geigy)
clodinafop
Common name clodinafop (BSI, pa E-ISO)
CAS RN [114420-56-3]
PHYSICAL CHEMISTRY
clodinafop-propargyl
Composition (R)- isomer. Mol. wt. 349.7 M.f. C17H13ClFNO4 Form Colourless crystals. M.p. 59.5 ºC; (tech., 48.2-57.1 ºC) V.p. 3.19 ´ 10-3 mPa (25 ºC) (OECD 104) KOW logP = 3.9 (25 ºC) Henry 2.79 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.37 (20 °C) Solubility In water 4.0 mg/l (pH7, 25 ºC). In ethanol 97, acetone 880, toluene 690, n-hexane 0.0086, n-octanol 25 (all in g/l, 25 ºC). Stability Relatively stable in acidic media at 50 ºC, hydrolyses in alkaline media; DT50 (25 ºC) 64 h (pH 7), 2.2 h (pH 9).
COMMERCIALISATION
History Reported by J. Amrein et al. (Proc. Br. Crop Prot. Conf. - Weeds,1989, 1, 71-76). Introduced by Ciba-Geigy AG (now Syngenta AG) and first marketed in 1990. Patents EP B 0083556, US 4713109 Manufacturers Syngenta
APPLICATIONS
clodinafop-propargyl
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Post-emergence, systemic grass herbicide. Phytotoxic symptoms appear within 1-3 weeks, affecting meristematic tissue. Uses Used for post-emergence control of annual grasses, including Avena, Lolium, Setaria, Phalaris and Alopecurus, in cereals, at 30-60 g/ha. Phytotoxicity Low toxicity to spring and winter wheat. Formulation types EC; WP. Compatibility Mainly used in combination with the safener cloquintocet-mexyl. Selected products: mixtures: 'Celio' (+ cloquintocet-mexyl) (France) (Syngenta); 'Topik' (+ cloquintocet-mexyl) (Syngenta)
OTHER PRODUCTS
clodinafop-propargyl
'Conduct' (Syngenta); 'Discover' (Syngenta); 'Magestan' (Syngenta); 'Boulevard' (GreenCrop); 'Marathon' (Me2) mixtures: 'Hawk' (+ trifluralin) (Syngenta); 'Horizon' (+ cloquintocet-mexyl) (Canada) (Syngenta); 'Amazon' (+ diflufenican) (Bayer CropScience, Syngenta); 'Lucifer' (+ diflufenican) (Bayer CropScience) Discontinued products mixtures: 'Amazon TP' * (+ diflufenican) (Novartis)
ANALYSIS
Details available from Syngenta.
MAMMALIAN TOXICOLOGY
clodinafop-propargyl
Oral Acute oral LD50 for male rats 1392, female rats 2271, mice >2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). May cause skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats 2.325 mg/l air. NOEL (2 y) for rats 0.35, (18 mo) for mice 1.2, (1 y) for dogs 3.3 mg/kg b.w. daily. ADI 0.004 mg/kg b.w. Toxicity class WHO (a.i.) III (company classification) EC classification (R22, R43)
ECOTOXICOLOGY
clodinafop-propargyl
Birds LD50 (8 d) for mallard ducks >2000, bobwhite quail >1455 mg/kg. Fish LC50 (96 h) for rainbow trout 0.39, carp 0.46, catfish 0.43 mg/l. Daphnia LC50 (48 h) >74 mg/l. Algae EC50 (96-120 h) for Scenedesmus subspicatus 25, Microcystis >65.5, Navicula 6.8 mg/l. Bees LD50 (48 h, oral and contact) >100 mg/bee. Worms LC50 for earthworms 210 mg/kg.
ENVIRONMENTAL FATE
Animals Hydrolysed to the corresponding acid which is excreted in urine and faeces. Plants In plants, rapidly degraded to the acid derivative as major metabolite. Soil/Environment In soil, undergoes rapid degradation to the free acid (DT50 <2 h) and then further to phenyl and pyridine moieties which are bound to the soil and mineralised. The free acid is mobile in soil, but is further degraded with DT50 5-20 d; in practice, there is a negligible leaching potential.
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