Propyzamide

256.13

256.13

245-951-4

2EZ95375S0

3077

DTXSID2020420

OFF-WHITE SOLID|WHITE CRYSTALS|NEEDLES|White powder

2924299036

29.1

3.43

Solid

1.2±0.1 g/cm3

155-156 °C

362.6±52.0 °C at 760 mmHg

2 °C

1.532

SOL IN MANY ALIPHATIC & AROMATIC SOLVENTS.

0-6°C

8.5X10-5 MM HG @ 25 DEG C

LD50 in male, female rats (mg/kg): 8350, 5620 orally (Viste)

ODORLESS

157.7 Ų [M+H]+

No rapid reaction with air. No rapid reaction with water.

Amides and Imides

3,5-DICHLORO-N-(1,1-DIMETHYL-2-PROPYNYL)BENZAMIDE is a chlorinated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

NONCORROSIVE UNDER NORMAL USE CONDITIONS.

9

UN 3077

3

40-50/53-36-20/21/22-11

36/37-60-61-36-26

CV3460000

Xn;N,N,Xn,F

NO DECOMP IN 2-YR STORAGE TRIAL UNDER NORMAL CONDITIONS.

P273-P281-P501

H351-H410

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 °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 °C and residence times of seconds for liquids and gases, and hours for solids.

USEPA; Pronamide Position Document 2/3 (1979) EPA/SPRD-80/68. Report contains information on the uses, environmental residues and health hazards of pronamide.|GOLD LS, ET AL; ENVIRON HEALTH PERSPECT 79 (0): 259-72 (1989). SUMMARY OF CARCINOGENIC POTENCY AND POSITIVITY FOR 492 RODENT CARCINOGENS IN THE CARCINOGENIC POTENCY DATABASE.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|Aggregated GHS information provided by 230 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P314, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|...GENERAL PERCAUTIONS: Take special care to avoid contact with the eyes, skin, or clothing. Wash clothing and gloves after use. PROTECTIVE CLOTHING: The following items of clothing are required when mixing or applying pronamide: a) Long-sleeved shirts and long pants, preferably one piece (overalls). b) Hat with brim. c) Heavy duty fabric or rubber work gloves.

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.

THE WETTABLE POWDER FORMULATION IS ONLY MILDLY IRRITATING TO EYES & SKIN.

U192; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U192; As stipulated in 40 CFR 261.33, when pronamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

URBAN/SUBURBAN: Pronamide was detected in ambient air in Kitakyushu in 1991-1992 at concentrations from 0.17-0.28 ng/cu m(1).

ACTIVATED CARBON PROTECTED NEW PLANTINGS OF RYEGRASS, TALL FESCUE, ORCHARD GRASS, KENTUCKY BLUEGRASS AND COLONIAL BENTGRASS AGAINST PRONAMIDE.

LD50 Rat (male) acute oral 8350 mg/kg (technical grade).|LD50 Rabbit percutaneous is greater than 3160 mg/kg (technical grade).|LD50 Rat (female) oral 5.6 g/kg.

Pronamide is not known to occur naturally. (SRC)

Pronamide's production and use as a herbicide to control broadleaf and grass weeds(1) results in its direct release to the environment(SRC). This compound is used on alfalfa, apple, artichoke, grape, lettuce, raspberry, and seed crops(2).

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 °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 °C and from 63-112 days at 15 °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).|For more Environmental Fate (Complete) data for PRONAMIDE (6 total), please visit the HSDB record page.

Based on laboratory experiments, some loss of pronamide due to photodecomposition may occur.|DEGRADATION OF KERB IS QUICKER IN ALKALINE THAN IN ACID SURROUNDINGS BUT THIS IS APPRECIABLE ONLY IN ACIDIC AND STRONGLY ALKALINE MEDIA. IRON AND COPPER SALTS HAD LITTLE INFLUENCE BUT SILVER SALTS HAD STRONG EFFECT.|The ultraviolet absorption spectra of pronamide in ethanol solution exhibits an absorption maxima at about 280 nm with a band extending into the environmentally significant region above 290 nm(1) indicating a potential for direct photolysis in sunlight(SRC). Based on laboratory experiments, some loss of pronamide due to photodecomposition on soil surfaces may occur(2). A photodegradation half-life of approximately 180 hours was reported for pronamide on a bentonite support(3). Pronamide has an acid hydrolysis rate constant of 4.3X10-3/M hr, a neutral hydrolysis rate constant of <1.5X10-5/M hr, and a base hydrolysis rate constant of 7.4X10-2/M hr(4). Chemical cyclization of pronamide to 2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methyleneoxazoline has been observed in soil and in aqueous solution(5,6). The rate constant for the vapor-phase reaction of pronamide with photochemically produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(7,SRC). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(7,SRC).

Pronamide has measured BCF values from 6-20(1). An estimated BCF value of 135 was calculated for pronamide(SRC), using an experimental log Kow of 3.43(2) and a recommended regression-derived equation(3). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is low(SRC).

204.17 L/kg|Very little leaching of pronamide occurs in most soil types as it is readily adsorbed on organic matter and other colloidal exchange sites(1). Adsorption distribution experiments with 18 different soil types has shown that, in general, pronamide adsorption increases proportionately with an increase in organic matter content(2). Soil partition coefficients were measured for pronamide in seven soils (organic carbon ranged from 0.01-16.9%; pH from 5.2-7.2); Kd values ranged from 0.04-72.2 with higher values corresponding to soils with higher organic carbon content(Koc values of 400-427(SRC))(3). Koc values of 204(4) and 800(5) were measured in soil for this compound. Pronamide had a pesticide leaching potential index value of 36 out of 100 indicating that this pesticide is not likely to leach significantly(6). According to a recommended classification scheme(7), these estimated Koc values suggest that pronamide has low to moderate mobility in soil(SRC).

The Henry's Law constant for pronamide is estimated as 1.9X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 8.5X10-5 mm Hg(1), and water solubility, 15 mg/L(2). This value indicates that pronamide will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 31 days(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 230 days(3,SRC). Pronamide's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil should not occur(SRC). However, volatilization of pronamide from soil surfaces under very hot and dry conditions has been observed during laboratory experiments(4).

SURFACE WATER: Pronamide was detected in drainage from 3 golf links with a maximum concentration reported as >8 ug/l(1). Water from final overflow, ponds, and wells from golf courses in Kanagawa Prefecture, Japan, contained pronamide in many samples at unreported amounts(1).|GROUNDWATER: Groundwater from the Granta catchment in eastern England did not contain measurable quantities of pronamide although it had been applied to crop surfaces(1).

Pronamide was detected during monitoring of imported and domestic pears at unreported concentrations (1992-1993)(1). Pronamide was detected during the FDA's program for monitoring pesticide residues in raw agricultural commodities from 1978-82(2) and 1983-86(3), 1989(4), and 1990(5) (unreported concentration).

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.

STUDIES ON METAB OF PRONAMIDE IN RAT & COW HAVE BEEN REPORTED. ...NO DIRECT EVIDENCE WAS PRESENTED TO INDICATE CLEAVAGE OF AMIDE LINKAGE OR AN ALTERATION OF 3,5-DICHLOROPHENYL RING. THUS, PRONAMIDE APPEARS TO BE DEGRADED IN ANIMALS TO NUMBER OF PRODUCTS SIMILAR TO THOSE REPORTED IN PLANTS & SOIL.|AFTER ADMIN ... /PRONAMIDE/ TO RATS & COWS PER ORAL /ROUTE/ UNCHANGED /PRONAMIDE ACCOUNTED FOR ONE-HALF OF THAT PROPORTION OF THE DOSE EXCRETED IN THE FECES, BUT FOR VERY LITTLE IN THE URINE. THE PRINCIPAL METABOLITES IN FECES OF TREATED RATS WERE 2-(3,5-DICHLOROPHENYL)-4,4-DIMETHYL-5-METHYLENEOXAZOLINE (535), N-(1,1-DIMETHYLACETONYL)-3,5-DICHLOROBENZAMIDE (536), 2-(3,5-DICHLOROPHENYL)-4,4-DIMETHYL-5-HYDROXYMETHYLOXAZOLINE (537), N-(1,1-DIMETHYL-3-HYDROXYACETONYL)-3,5-DICHLOROBENZAMIDE (538), N-(1,1-DIMETHYL-3-HYDROXYPROPYL)-3,5-DICHLOROBENZAMIDE (539), N-(1,1-DIMETHYL-2,3-DIHYDROXYPROPYL)-3,5-DICHLOROBENZAMIDE (540), BETA-(3,5-DICHLOROBENZAMIDO)-BETA-METHYLBUTYRIC ACID (541), & ALPHA-(3,5-DICHLOROBENZAMIDO)ISOBUTYRIC ACID (542), & IN RAT URINE THEY WERE (537), (538), (540), (541), (542), & BETA-(3,5-DICHLOROBENZAMIDO)-ALPHA-HYDROXY-BETA-METHYLBUTYRIC ACID (543). IN THE URINE OF TREATED COWS (541), (542), & (543) WERE PRESENT. A TENTATIVE INTER-RELATIONSHIP AMONG THE VARIOUS METABOLITES IS ILLUSTRATED.

Although there are numerous herbicides that disrupt mitosis as a mechanism of action, to date not one has compared the effects of these disrupters on a single specials and over a range of concentrations. Oat seedlings, treated with a range of concentrations of nine different mitotic disrupter herbicides" (including pronamide), were examined by immunofluorescence microscopy of tubulin in methacrylate sections. All herbicides caused the same kinds of microtubule disruption, although the concentrations required to cause the effects differed markedly between the herbicides. Effects on spindle and phragmnoplast mitotic microtubule arrays were seen at the lowest concentrations and manifested as multipolar spindles and bifurcated phragmoplasts (which subsequently resulted in abnormal cell plate formation). At increasing concentrations, effects on mitotic microtubule arrays manifested as microtubule tufts at kinetochores and reduction of cortical microtubules resulting in arrested prometaphase figures and isodiametric cells. These data indicate that all mitotic disrupter herbicides have a common primary mechanism of action, inhibition of microtubu1e polymerization, and that margina1 effects observed in the past were the result of incomplete inhibition and/or differential sensitivity of the microtubu1e arrays.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

THE WETTABLE POWDER FORMULATION IS ONLY MILDLY IRRITATING TO EYES & SKIN.

3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide

HERBICIDE FOR VEGETABLES, 46%; FOR OTHER FIELD CROPS, 46%; FOR PASTURE & RANGELAND, 8% (1982)

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

IT SHOULD NOT BE MIXED WITH OTHER TYPES OF PESTICIDES BUT MAY BE COMBINED WITH CERTAIN OTHER HERBICIDES.|ACTIVATED CARBON PROTECTED NEW PLANTINGS OF RYEGRASS, TALL FESCUE, ORCHARD GRASS, KENTUCKY BLUEGRASS AND COLONIAL BENTGRASS AGAINST PRONAMIDE.|RATES: 0.75-2.0 LB/ACRE. USUAL CARRIER: WATER @ 30-50 GAL/ACRE.|Horrom BW et al, South Africa Patent 6,800,000 corresponding to US Patents 3,534,098 and 3,640,699 (1969, 1970, 1972 all to Rohm & Haas).

Samples were extracted, purified and determined by gas chromatography or thin layer chromatography. The TLC detection threshold was 0.5-1 ug kerb/sample. Gas chromatography had sensitivity thresholds of 0.02 mg kerb/l water and 0.03-0.05 mg kerb/kg soil or plants. Recovery from water, soil or plants was 87, 70 and 67% respectively. Sensitivity of determination by TLC by spot surface measuring was 0.02 mg kerb/l water and 0.1 mg kerb/kg soil or plants.|Product analysis by GLC. Residues determined by GLC of a derivative or by GLC with ECD.|Pronamide was measured in air following collection by a high-volume air sampler with a XAD-2 resin trap, dichloromethane extraction, and GC/MS-SIM. Overall recovery = 102%; detection limit = 0.1 ng/cu m.

Agrochemicals -> Herbicides|Pharmaceuticals|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Propyzamide has known environmental transformation products that include 2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methylene-oxazoline and N-(1,1-dimethylacetonyl)-3,5-dichlorobenzamide.|Propyzamide has known environmental transformation products that include RH-20839, RH-24580, and RH-24644.