Specifications

chlorimuron-ethyl 95%TC/ 25%WP and 25%WDG
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NOMENCLATURE

Common name: chlorimuron-ethyl

 

Classification: herbicide

 

IUPAC name :ethyl 2-(4-chloro-6-methoxypyrimidin-2-ylcarbamoylsulfamoyl)benzoate 

 

Chemical  name :ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate 

CAS RN [90982-32-4]    Development codes DPX-F6025 (Du Pont) 

 

PHYSICAL CHEMISTRY
Composition Tech. is >95%.  Mol. wt. 414.8  M.f. C15H15ClN4O6S  Form Colourless crystals.  M.p. 181 ºC  V.p. 4.9 ´ 10-7 mPa  KOW logP = 0.11 (pH 7)  Henry 1.7 ´ 10-10 Pa m3 mol-1  S.g./density 1.51 (25 ºC)  Solubility In water 9 (pH 5), 1200 (pH 7) (both in mg/l, 25 ºC). Low solubility in organic solvents.  Stability In water DT50 17-25 d (pH 5, 25 ºC).  pKa 4.2 

 

APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Crop selectivity derives from plant metabolism both by homoglutathione conjugation and by de-esterification (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)).  Uses Used post-emergence for control of important broad-leaved weeds, such as cocklebur, pigweed, sunflower and annual morning glory, in soya beans and peanuts. Active at 9-13 g/ha.  Formulation types WG.   

 

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 4102 mg/kg.  Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Not a skin irritant or eye irritant (rabbits). Not a skin sensitiser (guinea pigs).  Inhalation LC50 (4 h) for rats >5 mg/l air.  NOEL (2 y) for rats 250 mg/kg diet (12.5 mg/kg daily); (1 y) for dogs 250 mg/kg diet (6.25 mg/kg daily). NOEL in: reproduction (2-generation) in rats 250 mg/kg diet; teratogenicity in rats 30, rabbits 15 mg/kg.  ADI 0.020 mg/kg b.w.  Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) III 

 

ECOTOXICOLOGY
Birds Acute oral LD50 (14 d) for mallard ducks >2510 mg/kg. Dietary LC50 for mallard ducks and bobwhite quail >5620 ppm.  Fish LC50 (96 h) for trout >1000, bluegill sunfish >100 mg/l.  Daphnia LC50 (48 h) 1000 mg/l.  Other aquatic spp. For Lemna gibba, EbC50 0.45 ppb, ErC50 45 mg/l, EC50 (frond counts) 0.27 ppb. LC50 for crayfish >1000 ppm.  Bees LD50 (48 h) >12.5 mg/bee.  Worms LC50 for earthworms (Eisenia foetida) >4050 mg/kg. 

 

ENVIRONMENTAL FATE
Animals Chlorimuron-ethyl is rapidly and extensively metabolised in the hen; 18 metabolites in the excreta were resolved by hplc.  Soil/Environment In soil, Kd >1.60 (pH 4.5, 5.6% o.m.), 0.28 (pH 5.8, 4.3 % o.m.), <0.03 (pH 6.5, 2.1% o.m.), <0.03 (pH 6.6, 1.1 % o.m.).