3,5-ジクロロ-N-(1,1-ジメチル-2-プロピニル)ベンズアミド

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Other

Herbicides

Environmental transformation -> Pesticides (parent, predecessor)

OFF-WHITE SOLID

WHITE CRYSTALS

NEEDLES

White powder

In water - 15 mg/l (25 °C). In methanol, isopropanol 150, cyclohexanone, methyl ethyl ketone 200, dimethyl sulfoxide 330 (all in g/l). Moderately soluble in benzene, xylene, carbon tetrachloride. Sightly soluble in petroleum ether.

SOL IN MANY ALIPHATIC & AROMATIC SOLVENTS.

155-156 °C

Decomposes above melting point; in solution for 28 days (pH 5-9, 20 °C) < 10% loss.

0.000085 [mmHg]

8.5X10-5 MM HG @ 25 °C

3,5-dichloro-n-(1,1-dimethyl-2-propynyl)benzamide is a white solid. Used as a selective herbicide.

Off-white or white odorless solid; [HSDB] Colorless or white crystalline solid; [MSDSonline]

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Carcinogenicity

Regulation (EC) No 1107/2009 (amended)

Pronamide (Propyzamide) is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

03/39/EC, Reg. (EU) 2016/2016, Reg. (EU) 2018/755, Reg. (EU) 2018/84, Reg. (EU) 2020/1093, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Propyzamide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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.

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).

Tolerances are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: alfalfa (fresh, storage, and hay); apples; artichokes; blackberries; blueberries; boysenberries; cattle (fat, mbyp, meat, kidney, and liver); cherries; clover; crown vetch; eggs; endive (escarole); goats (fat, mbyp, meat, kidney, and liver); grapes; hogs (fat, mbyp, meat, kidney, and liver); horses (fat, mbyp, meat, kidney, and liver); lettuce; milk; nectarines; peaches; pears; plums; poultry (fat, mbyp, meat, kidney, and liver), radicchio greens (tops); raspberies; sainfoin; sheep (fat, mbyp, meat, kidney, and liver); trefoil.

Tolerances with regional registration are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: peas (dried, winter); rhubarb.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Propyzamide is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0082; Pesticide type: herbicide; Registration Standard Date: 04/15/86; Case Status: RED Approved 03/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Propyzamide; Data Call-in (DCI) Date(s): 09/28/90, 06/10/94, 03/03/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

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).

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.

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.

Tolerances are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: alfalfa (fresh, storage, and hay), 10 ppm; apples, 0.1 ppm; artichokes, 0.1 ppm; blackberries, 0.5 ppm; blueberries, 0.5 ppm; boysenberries, 0.5 ppm; cattle (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; cattle (kidney and liver), 0.2 ppm; cherries, 0.1 ppm; clover, 5.0 ppm; crown vetch, 5.0 ppm; eggs, 0.02 ppm; endive (escarole), 2.0 ppm; goats (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; goats (kidney and liver), 0.2 ppm; grapes, 0.1 ppm; hogs (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; hogs (kidney and liver), 0.2 ppm; horses (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; horses (kidney and liver), 0.2 ppm; lettuce, 1.0 ppm; milk, 0.02 ppm; nectarines, 0.1 ppm; peaches, 0.1 ppm; pears, 0.1 ppm; plums, 0.1 ppm; poultry (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; poultry (kidney and liver), 0.2 ppm; radicchio greens (tops) 2.0 ppm; raspberies, 0.05 ppm; sainfoin, 5.0 ppm; sheep (fat, mbyp (except kidney and liver) and meat), 0.02 ppm; sheep (kidney and liver), 0.2 ppm; trefoil, 5.0 ppm.

Tolerances with regional registration are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: peas (dried, winter), 0.05 ppm; rhubarb, 0.1 ppm.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

...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.

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.

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).

Pronamide

7.5 x 10 ^-2 mg/kg-day

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).

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).

Tolerances are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: alfalfa (fresh, storage, and hay); apples; artichokes; blackberries; blueberries; boysenberries; cattle (fat, mbyp, meat, kidney, and liver); cherries; clover; crown vetch; eggs; endive (escarole); goats (fat, mbyp, meat, kidney, and liver); grapes; hogs (fat, mbyp, meat, kidney, and liver); horses (fat, mbyp, meat, kidney, and liver); lettuce; milk; nectarines; peaches; pears; plums; poultry (fat, mbyp, meat, kidney, and liver), radicchio greens (tops); raspberies; sainfoin; sheep (fat, mbyp, meat, kidney, and liver); trefoil.

Tolerances with regional registration are established for the combined residues of the herbicide 3,5-dichloro-N-(1,1-dimethyl-2-propynyl)benzamide and its metabolites in or on the following raw agricultural commodities: peas (dried, winter); rhubarb.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Propyzamide is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0082; Pesticide type: herbicide; Registration Standard Date: 04/15/86; Case Status: RED Approved 03/94; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Propyzamide; Data Call-in (DCI) Date(s): 09/28/90, 06/10/94, 03/03/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

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).

(AZ) ARIZONA 52 ug/l

(FL) FLORIDA 53 ug/L

(ME) MAINE 23 ug/l

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.

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.

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.

Used as selective pre-emergence herbicide; [Merck Index]

Farming (Pesticides) [Category: Industry]

SELECTIVE HERBICIDE THAT WILL CONTROL MANY BROADLEAF & GRASS WEEDS PREEMERGENCE IN LETTUCE /AND OTHER CROPS/

Selective systemic herbicide, ..... used for the selective control of many annual and perennial grasses, and some broad- leaved weeds .....

This is a man-made compound that is used as a pesticide.

(1978) 4.09X10+8 G (CONSUMPTION)

(1982) 5.90X10+8 G (CONSUMPTION)

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)

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

Pharmaceuticals

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides

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).