clodinafop-propargyl 15% WP 240g/l EC 8% EW grass killer made in China

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 ; (tech., 48.2-57.1 )  V.p. 3.19 ?10-3 mPa (25 ) (OECD 104)  KOW logP = 3.9 (25 )  Henry 2.79 ?10-4 Pa m3 mol-1 (calc.)  S.g./density 1.37 (20 )  Solubility In water 4.0 mg/l (pH7, 25 ). In ethanol 97, acetone 880, toluene 690, n-hexane 0.0086, n-octanol 25 (all in g/l, 25 ).  Stability Relatively stable in acidic media at 50 , hydrolyses in alkaline media; DT50 (25 ) 64 h (pH 7), 2.2 h (pH 9).  

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)

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.