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Your Location：Home>Product Center >> Pesticide API and intermediates >> Propyzamide
  • Propyzamide
Name:Propyzamide
CAS No:23950-58-5

PRODUCT DESCRIPTION

【Name】
Propyzamide
【CAS Registry number】
23950-58-5
【Synonyms】
3,5-Dichloro-N-(1,1-dimethyl-2-propynyl)benzamide
Pronamide
3,5-Dichloro-N-(1,1-dimethylprop-2-ynyl)benzamide
3,5-dichloro-N-(1,1-dimethylpropynyl) benzamide
kerb
【EINECS(EC#)】
245-951-4
【Molecular Formula】
C12H11Cl2NO (Products with the same molecular formula)
【Molecular Weight】
256.13
【Inchi】
InChI=1/C12H11Cl2NO/c1-4-12(2,3)15-11(16)8-5-9(13)7-10(14)6-8/h1,5-7H,2-3H3,(H,15,16)
【InChIKey】
PHNUZKMIPFFYSO-UHFFFAOYSA-N
【Canonical SMILES】
CC(C)(C#C)NC(=O)C1=CC(=CC(=C1)Cl)Cl
【MOL File】
23950-58-5.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline powder or granular
【Density】
1.258 g/cm3
【Melting Point】
155 - 156 C
【Boiling Point】
340.9 °C at 760 mmHg
【Vapour】
8.35E-05mmHg at 25°C
【Refractive Index】
1.561
【Flash Point】
160 °C
【Water】
15 mg/l
【Solubilities】
15 mg/l
【Color/Form】
OFF-WHITE SOLID
WHITE CRYSTALS
NEEDLES
White powder
【Stability】
No decomp in 2-yr storage trial under normal conditions.
【Storage temp】
0-6°C
【Spectral properties】
Intense mass spectral peaks: 173 m/z (100%), 175 m/z (85%), 255 m/z (37%), 145 m/z (31%)
UV spectra of pronamide in ethanol solution... two bands located at 280 and 207 nm.
【Computed Properties】
Molecular Weight:256.12784 [g/mol]
Molecular Formula:C12H11Cl2NO
XLogP3-AA:3.2
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:255.021769
MonoIsotopic Mass:255.021769
Topological Polar Surface Area:29.1
Heavy Atom Count:16
Formal Charge:0
Complexity:308
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:9

Safety and Handling

【Hazard Codes】
Xn:Harmful;N:Dangerousfortheenvironment;
【Risk Statements】
R40;R50/53
【Safety Statements 】
S36/37;S60;S61
【Skin, Eye, and Respiratory Irritations】
THE WETTABLE POWDER FORMULATION IS ONLY MILDLY IRRITATING TO EYES & SKIN.
【Transport】
UN 3077
【Formulations/Preparations】
Wettable powder; granular formulations; suspendible concentrate.
SUPPLIED AS A 50% WETTABLE POWDER, & INERT & FERTILIZER GRANULAR FORMULATIONS.
TECHNICAL PRODUCT IS 94-95% PURE.
Mixtures: (pronamide +) clopyralid; diuron; simazine; oxyfluorfen; chlorpropham; terbuthylazine; oxyfluorfen
【Other Preventative Measures】
SAFETY PRECAUTIONS FOR HANDLING & APPLICATION: AVOID SKIN CONTACT. DO NOT BREATHE DUST OR SPRAY MIST. IN CASE OF EYE CONTACT, WASH WITH COPIOUS QUANTITIES OF WATER. DO NOT CONTAMINATE FOOD OR FEEDSTUFFS. DO NOT PERMIT DRIFT TO NONTARGET AREAS.
【Protective Equipment and Clothing】
THE WETTABLE POWDER FORMULATION IS ONLY MILDLY IRRITATING TO EYES & SKIN.
【Octanol/Water Partition Coefficient】
Log Kow = 3.43
【Disposal Methods】
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U192, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Pronamide has been prepared by the Schotten-Bauman reaction of 3,5-dichlorobenzylchloride with 3-amino-3-methylbutyne.
Methylbutynol + ammonia + 3,5-dichlorobenzoyl chloride (ammoniation/amide formation)
U.S. Production

(1978) 4.09X10+8 G (CONSUMPTION)
(1982) 5.90X10+8 G (CONSUMPTION)
Consumption Patterns

HERBICIDE FOR VEGETABLES, 46%; FOR OTHER FIELD CROPS, 46%; FOR PASTURE & RANGELAND, 8% (1982)
【Usage】
Selective herbicide that will control many broadleaf & grass weeds preemergence in lettuce and other crops.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
TRACES OF THE PARENT HERBICIDE WERE FOUND IN MILK OF COWS TREATED WITH 5 PPM OF KERB (N-(1,1-DIMETHYLPROPYNYL)-3,5-DICHLOROBENZAMIDE) IN THE FEED, BUT NONE OF THE KNOWN METABOLITES WERE FOUND.
To obtain activity, pronamide must move into the root zone of the weeds. Little activity is obtained from foliar contact alone. Pronamide is readily absorbed by plants through the root system, translocated upward, and distributed into the entire plant. The degree of translocation from leaf absorption is not appreciable.
Poorly absorbed from the gastrointestinal tract of rats and cows; metabolized by side-chain oxidation and excreted in urine and feces.
A simple high pressure liquid chromatography procedure was used to determine pronamide exposure in sprayers and their dermal absorption and excretion in guinea pigs. Results of dermal application to guinea pigs demonstrated a strong correlation between the applied dermal dose and the urinary residue excretion over the dosage range tested. As the dosage was increased the urinary excretion of residues was also increased. Residue levels were also determined to estimate skin contamination after sampling by filter pads attached to the clothing and arms of agricultural sprayers. Residues in the workers urine before and after exposure were also determined. Average exposure values of 0.83 mg/hr/person for pronamide were extrapolated from residue values obtained from analyzing the pads. Little correlation was found between the measured residues from exposed subjects and residues quantified in their urine samples.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: MOVEMENT OF PRONAMIDE IS GREATEST IN COARSE TEXTURED SOILS. LEACHING OF MOST SOIL RESIDUALS OCCURS IN LOAMY SANDS AND IN SILT LOAMS.
TERRESTRIAL FATE: Spring spraying of 3 kg kerb/ha controlled weeds and left 0.15 mg propyzamide/kg in harvested flower heads of Anthemis nobilis and the top 5 cm of soil. At 5-10 cm, the residue was 0.056 mg/kg. The rate of herbicide decay depended more on the temp than on the soil moisture.
TERRESTRIAL FATE: Based on a recommended classification scheme(1), experimental Koc values from 200-800(2-4), indicate that pronamide will have low to moderate mobility in soil(SRC). Very little leaching of pronamide occurs in most soil types as it is readily adsorbed on organic matter and other colloidal exchange sites(5,6). Pronamide is degraded via both biotic and abiotic pathways to a number of transformation products in soils(7,SRC). Initial transformation reactions in soil include cyclization to form 2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methyleneoxazoline followed by hydrolysis to N-(1,1-dimethylacetonyl)-3,5-dichlorobenzamide(7). These two transformation products and small amounts of unchanged pronamide represented over 96% of the herbicide recovered 90 days after soil treatment(7). Other degradation products were present in trace amounts and were the result of alterations in the terminal carbons of the propynyl side chain(7). Transformation to the cyclized and subsequent hydrolysis products occurred about three times more rapidly in a non-sterilized soil as compared to the sterilized soil over a 33 day period(8); formation of carbon dioxide in the non-sterilized, but not in the sterilized soil indicated biological mediation(8).
TERRESTRIAL FATE: Loss of pronamide from soil surfaces due to photodecomposition may occur(1,2). The average persistence of pronamide when applied at recommended herbicidal rates is variable (2-9 months) and depends on soil types and climatic conditions with residual activity greater in sandy soils with low organic carbon content(2). The degradation half-life of pronamide in 18 different soil types at 25 deg C ranged from 9.5 to 32.4 days(3). The degradation half-life in 5 different soils varied from 23-42 days at 25 deg C and from 63-112 days at 15 deg C(4). Observed half-life under field conditions in a sandy loam soil varied from 40-80 days(5). Observed half-lives under field conditions averaged about 40 days in 14 different soil types(6). Pronamide had increasingly rapid initial biodegradation rates with increasing numbers of previous treatments(7). Half-lives for pronamide were approximately 45, 35, 22, and 18 days, respectively, in plots treated for the first, second, third, and fourth time(7). Volatilization of pronamide should not be an important fate process from moist or dry soil surfaces(SRC) given an estimated Henry's Law constant of 1.9X10-6 atm-cu m/mole(8,9,SRC) and an experimental vapor pressure of 8.5X10-5 mm Hg, respectively(8). However, under very hot and dry conditions, volatilization has been noted(2).
AQUATIC FATE: When released to water, pronamide may be subject to direct photolysis as it adsorbs sunlight radiation(1) and has been observed to photodecompose on soil surfaces(2). Chemical cyclization of pronamide may occur and can be catalyzed by metal ions such as silver(3,4). As biodegradation in soil has been demonstrated(5,6), biodegradation in natural waters is possible(SRC). Based on a recommended classification scheme(7), experimental Koc values from 200-800(8-10), indicate that pronamide may adsorb to suspended solids and sediment(SRC) in the water column. Pronamide may volatilize slowly from water surfaces based on an estimated Henry's Law constant of 1.9X10-6 atm-cu m/mole(SRC), calculated using experimental values for water solubility(11) and vapor pressure(12). Estimated half-lives for a model river and model lake are 31 and 230 days, respectively(13,SRC). Measured BCF values from 6-20(14) indicate that pronamide will not bioconcentrate in aquatic organisms(SRC) according to a classification scheme(15).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 8.5X10-5 mm Hg at 25 deg C(2,SRC) indicates that pronamide will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pronamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 12 hours(3,SRC). Particulate-phase pronamide may be physically removed from the air by wet and dry deposition(SRC).

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