Products

 

PYRIMETHANIL

 

Fungicide
FRAC  9; anilinopyrimidine

 

NOMENCLATURE
Common name pyrimethanil (BSI, draft ISO)
IUPAC name N-(4,6-dimethylpyrimidin-2-yl)aniline 
Chemical Abstracts name 4,6-dimethyl-N-phenyl-2-pyrimidinamine 
CAS RN [53112-28-0]  Development codes SN 100309 (Schering); ZK 100309 

PHYSICAL CHEMISTRY
Mol. wt. 199.3  M.f. C12H13N3  Form Colourless crystals.  M.p. 96.3 ºC  V.p. 2.2 mPa (25 ºC) (OECD 104)  KOW logP = 2.84 (pH 6.1, 25 ºC)  Henry 3.6 ´ 10-3 Pa m3 mol-1 (calc.)  S.g./density 1.15 (20 ºC)  Solubility In water 0.121 g/l (pH 6.1, 25 ºC). In acetone 389, ethyl acetate 617, methanol 176, methylene chloride 1000, n-hexane 23.7, toluene 412 (all in g/l, 20 °C).  Stability Stable in water within the relevant pH range. Stable for 14 d at 54 ºC.  pKa 3.52, weak base (20 °C) (OECD 112) 

COMMERCIALISATION
History Reported by G. L. Neumann et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 395). Introduced by Schering (now Aventis CropScience).  Manufacturers Aventis

APPLICATIONS
Biochemistry Inhibitor of methionine biosynthesis leading to inhibition of the secretion of enzymes necessary for infection.  Mode of action Protectant (in Botrytis) and both protective and curative action (in Venturia).  Uses Control of grey mould (Botrytis cinerea) on vines, fruit, vegetables and ornamentals. Control of leaf scab (Venturia inaequalis or V. pirina) on pome fruit.  Phytotoxicity May be phytotoxic in closed systems at ³80% r.h. on certain species.  Formulation types SC.