Allidochlor
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Allidochlor
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CAS No:
93-71-0
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Formula:
C8H12ClNO
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Chemical Name:
Allidochlor
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Synonyms:
Acetamide,2-chloro-N,N-di-2-propen-1-yl-;Acetamide,N,N-diallyl-2-chloro-;Acetamide,2-chloro-N,N-di-2-propenyl-;2-Chloro-N,N-di-2-propen-1-ylacetamide;CP 6,343;CDAA;α-Chloro-N,N-diallylacetamide;2-Chloro-N,N-diallylacetamide;N,N-Diallyl-α-chloroacetamide;N,N-Diallyl-2-chloroacetamide;Randox;Allidochlor;N,N-Diallylchloroacetamide;Alidochlor;Alidochlore;Lucaoxian;2-Chloro-N,N-bis(prop-2-en-1-yl)acetamide
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CAS No:
Description
Amber liquid or granules.Slightly soluble in water; soluble in alcohol, hexane, and xylene. An oily, amber liquid. Slightly irritating odor
Randox is an amber liquid. (NTP, 1992)
Randox is an amber liquid. (NTP, 1992)|Allidochlor is a tertiary carboxamide.
Allidochlor Basic Attributes
173.63998
173.64
202-270-7
2E0WF154QR
2996
DTXSID2041591
OILY AMBER LIQUID OR GRANULES|Liquid
2924199016
Characteristics
20.3
1.34
Randox is an amber liquid. (NTP, 1992)
1.088 g/cm3 @ Temp: 25 °C
145 °C
92 °C @ Press: 2 Torr
186 DEG C OC; 15 DEG C CC
1.478
In water, 1.97X10+4 mg/l @ 25 deg C
0-6ºC
9.40X10-3 mm Hg @ 20 deg C
LD50 orally in rats: 700 mg/kg (Bailey, White)
CHLORINE ATOM IS LABILE
Slightly water soluble.
Amides and Imides
Corrosive to steel. (NTP, 1992).
CORROSIVE TO ORDINARY STEEL
Safety Information
III
6.1(b)
UN 2902
R21/22
S26;S28;S61;S36/S37/S39
AB5250000
Xn: Harmful;N: Dangerous for the environment;
Decomposed by acids and bases.
P273-P280-P305 + P351 + P338
H302-H312-H315-H319-H411
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
...ON CONTACT WITH ACIDS OR ACID FUMES, THEY EVOLVE HIGHLY TOXIC CHLORIDE FUMES. /CHLORIDES/|Incompatible with alkaline and acidic formulating substances.
Flash point data for this compound are not available. It is probably not flammable. (NTP, 1992)
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 42 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or a Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: 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)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|WEAR RUBBER GLOVES & GOGGLES.
HANDLE ONLY WITH ADEQUATE VENTILATION. IN CASE OF CONTACT IN EYES, FLUSH WITH WATER FOR 15 MINUTES & GET MEDICAL ATTENTION. IF SPILLED ON SKIN, WASH IMMEDIATELY WITH SOAP & WATER.
Moderately irritating to skin and eyes
SOIL: In 1989, Randox was not detected in soil on 12 farms in the Fraser Valley, British Columbia(1).
Toxicity
WHEN COMBINED WITH TRICHLOROBENZYL CHLORIDE (TCBC), IT IS OFFERED AS A BROADER-SPECTRUM MIXT FOR WEED CONTROL IN CORN... COMBINATION, HOWEVER, DOES HAVE DISADVANTAGES OF CONSIDERABLY INCR IRRITATING PROPERTIES, /RESULTING FROM BOTH/...& PROLONGED PERSISTENCE IN SOIL...|N,N-DIALLYL-2,2-DICHLOROACETAMIDE AN EFFECTIVE PROTECTANT FOR CORN AGAINST INJURY BY THIOCARBAMATE HERBICIDES.
Randox's former production and use(3) as a selective pre-planting or pre-emergence herbicide(1) resulted in its direct release to the environment through various waste streams(SRC). The material is believed to be no longer manufactured, or marketed for crop protection use(2).
...STUDIES USING CO2 TRAIN SHOWED (14)CO2 LIBERATION FROM SOIL TREATED WITH EITHER (14)C-CARBONYL- OR (14)C-ALLYL-LABELED CDAA /N,N-DIALLYLCHLOROACETAMIDE/. AMT GENERATED REPRESENTED APPROX 20% OF TOTAL (14)CO2 TRAPPED. THUS SOME DECOMP...OCCURS IN SOIL.|DISSIPATION STUDIES IN SOIL USING CHEM ANAL FOR DETERMINATION...INDICATED RAPID LOSS OF PARENT COMPD. T/2 WAS ESTIMATED TO BE APPROX 16-18 DAYS & WAS FAIRLY REPRESENTATIVE OVER BROAD RANGE OF SOIL TYPES & CLIMATIC CONDITIONS. SOME...LOSS WOULD BE ATTRIBUTABLE TO VOLATILITY...|TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from a structure estimation method(2), indicates that Randox is expected to have moderate mobility in soil(SRC). Volatilization of Randox from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.07X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 9.40X10-3 mm Hg(4), and water solubility, 1.97X10+4 mg/l(3). Randox is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.40X10-3 mm Hg(4). Biodegradation may be important as one study found 100% degradation in 3 months in soil(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 230(SRC), determined from an estimation method(2), indicates that Randox is expected to adsorb moderately to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.07X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 9.40X10-3 mm Hg(8), and water solubility, 1.97X10+4 mg/l(4). According to a classification scheme(5), an estimated BCF of 5(SRC), from an estimated log Kow of 1.79(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation may be important as one study found 100% degradation in 3 months in soil(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Randox, which has a vapor pressure of 9.40X10-3 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase Randox 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 5 hrs(SRC), calculated from its rate constant of 7.55X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).
HYDROLYSIS IS SECONDARY...TO MICROBIAL BREAKDOWN...RESPONSIBLE FOR DECOMP.|The rate constant for the vapor-phase reaction of Randox with photochemically-produced hydroxyl radicals has been estimated as 7.55X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
An estimated BCF of 5 was calculated for Randox(SRC), using an estimated log Kow of 1.79(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
19.95 L/kg|ADSORPTION /IN BASIC SOIL IS/ DIRECTLY PROP TO COLLOID CONTENT OF SOIL.|Duration of /chemical/ activity 3-6 weeks, depending on soil.|Using a structure estimation method based on molecular connectivity indices(1), the Koc for Randox can be estimated to be 230(SRC). According to a classification scheme(2), this estimated Koc value suggests that Randox is expected to have moderate mobility in soil.
...IN ABSENCE OF ADSORPTIVE FORCES, 4 LB/ACRE VOLATILIZES IN LESS THAN 8 HR AT 7 °C OR ABOVE.|The Henry's Law constant for Randox is estimated as 1.07X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 9.40X10-3 mm Hg(1), and water solubility, 1.97X10+4 mg/l(2). This Henry's Law constant indicates that Randox is expected to be essentially nonvolatile from water surfaces(3). Randox's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces will not occur(SRC). Randox is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.40X10-3 mm Hg(1).
Occupational exposure to Randox may have occurred through dermal contact with this compound at workplaces where randox was produced or used. (SRC)
Drug Information
3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).
...CARBONYL-LABELED (14)C-DIALLYLCHLOROACETAMIDE TREATED PLANTS /WERE GROWN/ IN CLOSED SYSTEM... /IT WAS SHOWN/...THAT MORE THAN 50% OF RADIOACTIVITY ABSORBED THROUGH ROOT SYSTEM OF CORN SEEDLINGS WAS EVOLVED AS (14)CO2, INDICATING THAT PLANT READILY DEGRADED DIALLYLCHLOROACETAMIDE MOLECULE.|CORN & SOYBEANS WERE CAPABLE OF RAPID UPTAKE OF RADIOACTIVITY FROM SOIL TREATED WITH (14)C-CARBONYL DIALLYLCHLOROACETAMIDE. UPTAKE REACHED AT 4-5 DAYS FOLLOWING EMERGENCE, WITH...MAX SPECIFIC ACTIVITY OF 85,000 CPM/G DRY WT FOR SOYBEANS AT 5 DAYS & 30,000 CPM/G DAY WT FOR CORN AT 4 DAYS.|.../CORN/ PLANTS...TREATED WITH ALLYL-(14)C-DIALLYLCHLOROACETAMIDE & GROWN TO MATURITY.../THEN/ HARVESTED & FRACTIONATED... LOW LEVEL OF RADIOACTIVITY...DISTRIBUTED AMONG /HULLS, GERMS & ENDOSPERM/. ...RANDOM DISTRIBUTION OF RADIOACTIVITY...SUGGESTS...NO UNUSUAL METAB...FORMED...AS RESULT OF DEGRADATION OF ALLYLIC MOIETY...|/IT IS/ ABSORBED MAINLY BY COTYLEDONS OF GRASS SEEDLING. /IT IS/ PROBABLE THAT DIALLYLCHLOROACETAMIDE ACCUMULATES IN THE CROWN & FIRST INTERNODE OF SEEDLING.|For more Absorption, Distribution and Excretion (Complete) data for RANDOX (6 total), please visit the HSDB record page.
...CDAA /N,N-DIALLYLCHLOROACETAMIDE/...MAY BE DEGRADED IN CORN.../BY A NONENZYMATIC REACTION/ WITH SUBSEQUENT HYDROLYSIS TO GLYCOLIC ACID & DIALLYLAMINE.|/METABOLISM OF N,N-DIALLYLCHLOROACETAMIDE (CDAA) WAS STUDIED IN CORN & SOYBEANS GROWN ON SOIL TREATED WITH CARBONYL-LABELED (14)C-CDAA/. GLYCOLIC ACID AND POSSIBLY LACTIC ACID OR GLYCERIC ACIDS WERE...THE MOST LIKELY METABOLITE CANDIDATES /AS SHOWN BY CHROMATOGRAPHIC ANALYSIS OF CORN AND SOYBEAN EXTRACTS/...EXAMINATION...OF SOYBEAN EXTRACTS 2 DAYS AFTER EMERGENCE INDICATED PRESENCE OF A COMPD BEHAVING LIKE GLYOXYLIC RATHER THAN GLYCOLIC ACID.|PLANT METABOLISM STUDIES OF /N,N-DIALLYLCHLOROACETAMIDE/ CDAA-(14)C INDICATED THAT THIS COMPOUND WAS DEGRADED INTO CO2 & GLYCOLLIC ACID WITH SUBSEQUENT INCORPORATION OF LABEL IN ALL FRACTIONS. CDAA ALSO REACTED WITH SENSITITIVE SULFHYDRYL GROUPS.|WHEN (14)C-CDAA /N,N-DIALLYLCHLOROACETAMIDE/ ADMIN AS SINGLE DOSE TO RATS, 86% WAS EXCRETED IN URINE DURING FIRST 48 HR; 16%, IN FECES. ABOUT 89% OF URINARY (14)C WAS THE MERCAPTURIC ACID OF CDAA. STUDIES ALSO SHOWED THAT CDAA REACTED NON-ENZYMATICALLY WITH GLUTATHIONE.|For more Metabolism/Metabolites (Complete) data for RANDOX (7 total), please visit the HSDB record page.
Inhibition of cell respiration|...AMIDE HERBICIDES INHIBIT PHOTOLYSIS OF WATER (HILL REACTION). /AMIDE HERBICIDES/
SYMPTOMS: Symptoms of exposure to this compound may include severe irritation of skin and eyes, and temperature sensitivity to cold. ACUTE/CHRONIC HAZARDS: When heated to decomposition it emits very toxic fumes. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
...HERBICIDE APPLIED IN FULL STRENGTH TO SKIN CAUSES SEVERE IRRITATION AND TEMPORARY SENSITIVITY TO COLD (FOR 4-6 HR)... UNDILUTED MATERIAL IN THE EYE HAS PRODUCED SERIOUS OCULAR DAMAGE.|NATURE OF TOXIC SYNDROME AFTER ORAL ADMIN HAS NOT BEEN DESCRIBED.
2-chloro-N,N-diallylacetamide
Allidochlor Use and Manufacturing
Prepared from chloroacetyl chloride and diallylamine: Speziale, Hamm, J Am Chem Soc 78, 2556 (1956)...Bruce Hanslick, US patent 2,844,629 (1958 to Am Home Prods).|Prepared from chloroacetyl chloride and diallylamine
Pre-emergent herbicide. Selective preemergence herbicide used to control annual grass weeds and some broad-leaved weeds in maize, millet, soybeans, sorghum, sugarcane, vegetables and ornamentals.
USEPA/OPP PC Code 019301; Trade Names: Randox, CP 6343, NCI-C04035.|4 LB/GALLON EMULSIFIABLE CONCENTRATE.|FOR CELERY, TOMATOES, POTATOES, RANDOX + VEGADEX HERBICIDES.|Granules, 20%.
Acetamide, 2-chloro-N,N-di-2-propen-1-yl-: ACTIVE|/RANDOX/ CONTROLS MANY ANNUAL GRASSES AND BROADLEAF IN CORN, SOYBEANS, SORGHUM, LIMA BEANS, SNAP BEANS, TOMATO TRANSPLANTS, DRY BEANS, CABBAGE, SWEET POTATOES, ONIONS, CELERY, SUGARCANE.|ALLIDOCHLOR IS A SELECTIVE PRE-EMERGENCE HERBICIDE...EG 0.025 PPM GIVES AN 80% INHIBITION OF GROWTH OF RYE GRASS.|THIS...HERBICIDE WAS...INTRODUCED...FOR USE IN CORN AND SOYBEANS TO CONTROL FOXTAIL, BROMEGRASS, CHEATGRASS, CRABGRASS, AND CERTAIN BROADLEAF WEEDS.|PREEMERGENCE (SPRAY OR GRANULAR, BAND OR BROADCAST), GROUND APPLICATION. POSTEMERGENCE, MULTIPLE TREATMENT ON ONIONS, & POSTEMERGENCE IN SUGARCANE. RATES: 4-5 LB/ACRE FOR MOST CROPS. ... USUAL CARRIER: SPRAY: WATER, 20 GPA OR MORE. MIN AGITATION...DURING APPLICATION. GRANULAR: ATTAPULGITE CLAY.|For more General Manufacturing Information (Complete) data for RANDOX (6 total), please visit the HSDB record page.
PRODUCT ANALYSIS IS BY REDUCTION TO INORG CHLORIDE BY SODIUM & 2-PROPANOL; MICROANALYSIS IS BY HYDROLYSIS TO AMINE WHICH IS DISTILLED INTO DIL HYDROCHLORIC ACID REACTED WITH CUPRIC ION IN PRESENCE OF CARBON DISULFIDE: HALL, SA ET AL, ANALYT CHEM, 23, 1866 (1951).|GENERAL SAMPLE, COLORIMETRIC REACTION, SPECTROPHOTOMETRY AT 435 NM; ZWEIG, G, ANALYTICAL METHODS FOR PESTICIDES, PLANT GROWTH REGULATORS AND FOOD ADDITIVES, ACADEMIC PRESS, NEW YORK, VOL 4, 191 (1964). GLC: THOMPSON, JF, COMMUNICABLE DISEASE CENTER, PESTICIDE RESEARCH LAB, PERRINE, FLA...
Computed Properties
Molecular Weight:173.64
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:173.0607417
Monoisotopic Mass:173.0607417
Topological Polar Surface Area:20.3
Heavy Atom Count:11
Complexity:146
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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