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Rimsulfuron

Rimsulfuron 95%TC
Rimsulfuron 25%WG

Herbicide

HRAC B WSSA 2; sulfonylurea

 

 

NOMENCLATURE

Common namerimsulfuron (BSI, pa E-ISO, ANSI)

IUPAC name1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pyridylsulfonyl)urea

Chemical Abstracts nameN-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide

CAS RN[122931-48-0]Development codesDPX-E9636 (Du Pont)

Rimsulfuron PHYSICAL CHEMISTRY

CompositionTech. is 99%.Mol. wt.431.4M.f.C14H17N5O7S2FormColourless crystals.M.p.176-178 ºCV.p.1.5 ´ 10-3mPa (25 ºC)KOWlogP = 0.288 (pH 5), -1.47 (pH 7) (25 ºC)S.g./density0.784 (25 ºC)SolubilityIn water (25 ºC) <10 mg/l (unbuffered); 7.3 g/l (buffered, pH 7).StabilityOn hydrolysis (25 ºC), DT504.6 d (pH 5), 7.2 d (pH 7), 0.3 d (pH 9).pKa4.0

Rimsulfuron COMMERCIALISATION

HistoryHerbicide reported by H. L. Palm et al. (Proc. 1989 Br. Crop Prot. Conf. - Weeds,1, 23). Introduced by E. I. du Pont de Nemours and Co. and first marketed in Europe in 1991.ManufacturersDu Pont

Rimsulfuron APPLICATIONS

BiochemistryBranched 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 rapid, selective metabolism by contraction of the sulfonylurea group and ring migration (L. Martinetti et al., Proc. Br. Crop Prot. Conf. - Pests Dis., 1995, 1, 405) and by hydroxylation on the pyrimidine ring, followed by glucose conjugation (M. K. Koeppe, IUPAC 5E-003 (1998); see Environmental Fate.Mode of actionSelective systemic herbicide, absorbed by the foliage and roots, with rapid translocation to the meristematic tissues.UsesRimsulfuron is a post-emergence sulfonylurea herbicide that effectively controls most annual and perennial grasses and several broad-leaved weeds in maize. Also used in tomatoes and potatoes. The target rate for most situations is 15 g a.i./ha. Rimsulfuron has a wide crop-safety margin under most conditions.Formulation typesWG.Selected tradenames:'Titus' (Europe, Africa, Mediterranean) (Du Pont)

Rimsulfuron OTHER TRADENAMES

'Matrix' (Du Pont); 'Shadeout' (Du Pont) mixtures:'Accent Gold' (+ clopyralid+ flumetsulam+ nicosulfuron) (Du Pont); 'Basis Gold' (+ atrazine+ nicosulfuron) (Du Pont); 'Basis' (+ thifensulfuron-methyl) (Du Pont); 'Grid' (+ thifensulfuron-methyl) (Du Pont); 'Pilar' (+ metribuzin) (Du Pont); 'Steadfast' (+ nicosulfuron) (Du Pont); 'Titer' (+ terbuthylazine) (Du Pont); 'Ultim' (+ nicosulfuron) (Du Pont); 'Wonder' (+ terbuthylazine) (Du Pont)

Rimsulfuron ANALYSIS

Product by glc. Residues by hplc. Details from Du Pont. Methods for sulfonylurea residues in crops, soil and water reviewed (A. C. Barefoot et al., Proc. Br. Crop Prot. Conf. - Weeds, 1995, 2, 707).

Rimsulfuron MAMMALIAN TOXICOLOGY

OralAcute oral LD50for rats >5000 mg/kg.Skin and eyeAcute percutaneous LD50for rabbits >2000 mg/kg. Non-irritating to skin; moderately irritating to eyes (rabbits). Non-sensitising to skin (guinea pigs).InhalationLC50(4 h) for rats >5.4 mg/l air.NOEL(2 y) for male rats 300, female rats 3000 ppm; (18 mo) for mice 2500 ppm; (1 y) for dogs 50 ppm. NOEL in 2-generation rat reproduction study 3000 ppm. Not teratogenic or oncogenic.OtherNon-mutagenic in the Ames test.Toxicity classWHO (a.i.) III (Table 5

Rimsulfuron ECOTOXICOLOGY

BirdsAcute oral LD50for bobwhite quail >2250, mallard ducks >2000 mg/kg. Dietary LC50for bobwhite quail and mallard ducks >5620 ppm.FishLC50(96 h) for bluegill sunfish and rainbow trout >390, carp >900, sheepshead minnow 110 mg/l.DaphniaLC50(48 h) >360 mg/l.BeesLD50(contact) >100 mg/bee; (dietary) >1000 ppm.WormsLC50(14 d) for earthworms (Eisenia foetida) >1000 mg/kg.