Fungicide

NOMENCLATURE

propamocarb hydrochloride

IUPAC name propyl 3-(dimethylamino)propylcarbamate hydrochloride 

Chemical Abstracts name propyl [3-(dimethylamino)propyl]carbamate hydrochloride 

CAS RN [25606-41-1]  EEC no. 247-125-9  Development codes AE B066752 (AgrEvo); SN 66 752 (Schering); Zk 66752 

propamocarb

Common name propamocarb (BSI, E-ISO, ANSI); propamocarbe ((m) F-ISO)

IUPAC name propyl 3-(dimethylamino)propylcarbamate 

Chemical Abstracts name propyl [3-(dimethylamino)propyl]carbamate 

CAS RN [24579-73-5]  Development codes SN 39744 (Schering) 

PHYSICAL CHEMISTRY

propamocarb hydrochloride

Composition The aqueous concentrate contains 780 g/l propamocarb hydrochloride.  Mol. wt. 224.7  M.f. C9H21ClN2O2  Form Colourless, faintly aromatic, hygroscopic crystals.  M.p. 45-55 ºC  V.p. 3.85 ´ 10-2 mPa (20 °C)  KOW logP = -2.6  Henry 8.65 ´ 10-9 Pa m3 mol-1 (20 °C, calc.)  S.g./density 1.085 g/ml (20 °C, aqueous concentrate)  Solubility In water 1005 g/l (20 °C). In methanol 656, dichloromethane >626, acetone 560, ethyl acetate 4.34, toluene 0.14, hexane <0.01 (all in g/l, 20 °C).  Stability Stable to hydrolysis, to temperatures up to 400 ºC, and to photolysis. 

propamocarb

Mol. wt. 188.3  M.f. C9H20N2O2  V.p. 730 mPa (25 °C)  KOW logP = 0.84 (20 °C)  Henry 1.5 ´ 10-4 Pa m3 mol-1 (25 °C)  Solubility In water >900 g/l (pH 7.0, 20 °C). In hexane >883, methanol >933, dichloromethane >937, toluene >852, acetone >921, ethyl acetate >856 (all in g/l, 20 °C).  pKa 9.5, strong base (K. Chamberlain et al., Pestic. Sci., 47, 265 (1996)) 

COMMERCIALISATION

History Fungicide reported by E. A. Pieroh et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1978, 43, 933). The hydrochloride introduced by Schering AG (now Aventis CropScience).  Patents DE 1567169; DE 1643040  Manufacturers Agriphar; Aventis

APPLICATIONS

Biochemistry Multi-site inhibitor.  Mode of action Systemic fungicide with protective action. Absorbed by the roots and leaves, and transported acropetally. 

propamocarb hydrochloride

Uses Specific control of phycomycetous diseases (Pythium, Phytophthora, Aphanomyces, Bremia, Peronospora, and Pseudoperonospora spp.). In particular, control of Pythium and Phytophthora spp. in vegetables, ornamentals, glasshouse tomatoes, glasshouse cucumbers, tulips, tobacco, and in forestry seedbeds; Pythium blight on turf; downy mildew on lettuce, cucurbits and cabbages; Phytophthora infestans in potatoes and tomatoes; Phytophthora cactorum on strawberries; etc. Applied to the soil, or used as a dip treatment (for bulbs and tubers) or seed treatment, and as a foliar spray in late-season applications.  Formulation types SC.  Selected tradenames: 'Banol' (Aventis); 'Previcur N' (Aventis); 'Previcur' (Aventis); 'Proplant' (Agriphar); mixtures: 'Tattoo' (+ mancozeb) (Aventis)

propamocarb

Selected tradenames: 'Promo' (Agrimix)

OTHER TRADENAMES

propamocarb hydrochloride

'Previcarb' (Aventis); 'Salvador' (Rocca) mixtures: 'Merlin' (+ chlorothalonil) (Aventis); 'Tattoo C' (+ chlorothalonil) (Aventis)

ANALYSIS

Product analysis by lc with u.v. detection (CIPAC Handbook, 1992, E, 184-6). Residues determined by glc with FID (I. A. Gentile & E. Passera, J. Chromatog., 1982, 236, 254). Details available from Aventis. 

MAMMALIAN TOXICOLOGY

Reviews FAO/WHO 47, 49 (see part 2 of the Bibliography). 

propamocarb hydrochloride

Oral Acute oral LD50 for rats 2000-2900, mice 2650-2800, dogs c. 1450 mg/kg.  Skin and eye Acute percutaneous LD50 for rats and mice >3000 mg/kg. Not a skin or eye irritant (rabbits). Not a skin sensitiser.  Inhalation LC50 (4 h) for rats >0.0057 mg/l air.  NOEL (2 y) for rats 1000, dogs 3000 ppm diet (41 and 70 mg/kg b.w., respy.).  ADI (JMPR) 0.1 mg/kg b.w. (for base) [1986].  Other Acute i.p. LD50 for rats 437-460 mg/kg. Not mutagenic. 

propamocarb

Inhalation LC50 (4 h) for rats >3.96 mg/l air.  Toxicity class WHO (a.i.) III (Table 5); EPA (formulation) IV 

ECOTOXICOLOGY

propamocarb hydrochloride

Birds Acute oral LD50 for pheasants 3050, mallard ducks >6290 mg/kg. LC50 (5 d) for pheasants >52 000, Japanese quail >25 000, mallard ducks 12 915 ppm diet.  Fish LC50 (96 h) for sheepshead minnow >100, carp 155, bluegill sunfish 275, trout 275 mg/l.  Daphnia LC50 (48 h) 280 mg/l.  Algae ErC50 (96 h) for Scenedesmus quadricauda 560 mg/l; EbC50 360 mg/l.  Other aquatic spp. EC50 (96 h) for Eastern oyster (Crassostrea virginica) 43.9 mg/l; LC50 (96 h) for mysid shrimp (Mysidopsis bahia) >100 mg/l.  Bees LD50 >0.1 mg/bee ('Previcur N').  Worms LC50 (14 d) >1000 mg/kg soil.  Other beneficial spp. Not toxic to Argsope argentata (web-building spider), Aleochara sp. (staphylinid beetle); not harmful to Poecilus cupreus (carabid beetle); slightly harmful to Coccinella septempunctata (ladybird). 

ENVIRONMENTAL FATE