101-21-3 Usage
Uses
Used in Agriculture:
Chlorpropham is used as a pre-emergent and post-emergent herbicide for controlling weeds in various crops such as carrot, onion, garlic, alfalfa, beans, blueberries, cane berries, cranberries, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli, and woody nursery stock. It is particularly useful in inhibiting post-harvest potato sprouting and controlling suckers in tobacco.
Used in Pesticide Products:
Chlorpropham is used in pesticide products for the treatment of plants and soil, helping to regulate plant growth and control weeds effectively in agricultural settings.
Physicochemical properties
A solid with low melting point of 41.4 ℃. The density is d30 1.180 and the refractive index is nD20 (after cooling) 1.5395.At 25 C, the solubility in the water is 89mg/L, and the degree of melting in the oil is medium (10% in the kerosene). It can be mixed with the lower alcohols, aromatics and most organic solvents. The purity of the industrial product is 98.5%, and the melting point is 38.5 ~ 40℃. Stable at lower than 100 C, but slowly hydrolyzed in acid and alkaline medium.
Toxicity
The acute oral administration of LD50 is 5 ~ 7.5g/kg in rats, and the acute oral administration is 5g/kg in rabbits. The drug had no toxic effect on rabbit skin for 20 hours or 2g/ kg feed for rats and dogs for 2 years. The acute oral administration is LD50>2g/kg for wild ducks. The TLm (48 hours) of goldfish and carp (48 hours) is 10 ~ 40mg/L.
Mechanism of action
Mitotic inhibitor, in many perennial crops and some annual crops, it can be used alone or with other herbicides as pre-emergent selective weed removal. It is a plant growth regulator as well as a herbicide. It inhibits the activity of beta amylase, inhibits the synthesis of RNA and protein, interferes with oxidative phosphorylation and photosynthesis, and destroys cell division. Chloraniline is volatile. The steam can be absorbed by the bud in order to suppress weed bud growth. The residual effect in soil was longer than that of aniline, and the selectivity for some crops was smaller than that of aniline. In addition, it also regulates the growth of plants. It is used to inhibit the germination of potatoes during storage, flower and fruit thinning etc..
Applicable crops
Alfalfa, wheat, corn, soybean, sunflower, potato, sugar beet, rice, carrots, spinach, onions, etc..
Prevention and control object
Annual grasses and certain broadleaf weeds including ryegrass, barnyard grass, bluegrass, purslane, chickweed and Tusizi etc. annual grasses and certain broadleaf weeds.
Usage method
The amount of effective components is 2.24 ~ 4.5kg per hectare per hectare below 16 C in pre seedling soil treatment. Double the amount above 24 centigrade and mix soil after application. The post seedling treatment is 1.2 ~ 3.5kg. For the post seedling treatment, the activity of herbicide is poor. But it can control amaranth and Polygonum, chickweed and purslane in the seedling. As a growth regulator, it is used to inhibit the germination of potatoes.
Preparation method
It can be made by reaction of inter - Chloroaniline and isopropyl chloroformate or isopropanol and ISO - chlorophenyl isocyanate
Analysis method
Determine the CO2 produced by acidolysis.
Residue determination:
(1) The H2SO4 is hydrolyzed of 1:1 by the extraction of two hydrogen methane, and the alkali is obtained. The 3- hydrogen aniline is vaporized and the colorimetric determination is carried out by the hypochlorite - phenol method.
(2) Infrared spectroscopy.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Chlorpropham is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Hazard
Toxic by ingestion.
Fire Hazard
Flash point data for Chlorpropham are not available, however Chlorpropham is probably combustible.
Trade name
ATLAS? CIPC 40; BEET-KLEEN? (with Fenuron? and isopropyl carbanilate); BUDNIP?; CAMPBELL’S? CIPC 40%; CHLORO IPC?; ELBANIL?; FASCO? WY-HOE; FURLOE?; FURLOE? 4EC; JACK WILSON? CHLORO 51 (OIL); LIRO METOXON?; MIRVALE?; MORCRAN? (with n-1-naphthylphthalamic acid); MSS? CICP; NEXOVAL?; PREVENOL? 56; PREVENTOL?; PREVENTOL? 56; PREWEED?; RESIDUREN?; RESIDUREN? EXTRA; SPROUT NIP?; SPROUT-NIP? EC; SPUDNIC?; SPUD-NIE?; STOPGERME?-S; TATERPEX?; TRIPEC? (with carbamic acid, phenyl-, 1-methylethyl ester); TRIHERBICIDE? CIPC; UNICROP? CIPC; WAREFOG?; Y3?
Environmental Fate
Soil. Hydrolyzes in soil forming 3-chloroaniline (Bartha, 1971; Hartley and Kidd,
1987; Smith, 1988; Rajagopal et al., 1989). In soil, Pseudomonas striata Chester, a
Flavobacterium sp., an Agrobacterium sp. and an Achromobacter sp. readily degraded
chlorpropham to 3-chloroaniline and 2-propanol. Subsequent degradation by enzymatic
hydrolysis yielded carbon dioxide, chloride ions and unidentified compounds (Kaufman,
1967; Rajagopal et al., 1989). Hydrolysis products that may form in soil and in microbial
cultures include N-phenyl-3-chlorocarbamic acid, 3-chloroaniline, 2-amino-4-chlorophenol, monoisopropyl carbonate, 2-propanol, carbon dioxide and condensation products
(Rajagopal et al., 1989). The reported half-lives in soil at 15 and 29°C are 65 and 30 days,
respectively (Hartley and Kidd, 1987)Plant. Chlorpropham is rapidly metabolized in plants (Ashton and Monaco, 1991).
Metabolites identified in soybean plants include isopropyl-N-4-hydroxy-3-chlorophenylcarbamate, 1-hydroxy-2-propyl-3′-chlorocarbanilate and isopropyl-N-5-chloro-2-hyPhotolytic. The photodegradation rate of chlorpropham in aqueous solution was
enhanced in the presence of a surfactant (TMN-10) (Tanaka et al., 1981). In a later study,
Tanaka et al. (1985) studied the photolysis of chlorpropham (50 mg/L) in aqueChemical/Physical. Emits toxic phosgene fumes when heated to decomposition (Sax
and Lewis, 1987). In a 0.50 N sodium hydroxide solution at 20°C, chlorpropham was
hydrolyzed to aniline derivatives. The half-life of this reaction was 3.5 days (El-Dib and
Aly, 1976). Simple hydrolysis leads to the formation of 3-chlorophenylcarbamic acid and
2-propanol. The acid is very unstable and is spontaneously converted to 3-chloroaniline
and carbon dioxide (Still and Herrett, 1976)
Check Digit Verification of cas no
The CAS Registry Mumber 101-21-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 101-21:
(5*1)+(4*0)+(3*1)+(2*2)+(1*1)=13
13 % 10 = 3
So 101-21-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H12N2O/c1-11(2)9(12)10-8-6-4-3-5-7-8/h3-7H,1-2H3,(H,10,12)
101-21-3Relevant articles and documents
Synthesis of N-(Hetero)aryl Carbamates via CuI/MNAO Catalyzed Cross-Coupling of (Hetero)aryl Halides with Potassium Cyanate in Alcohols
Kumar, S. Vijay,Ma, Dawei
, p. 2706 - 2713 (2018/03/09)
An efficient route to N-(hetero)aryl carbamates was developed through CuI/MNAO [2-((2-methylnaphthalen-1-yl)amino)-2-oxoacetic acid] catalyzed cross-coupling of (hetero)aryl chlorides with potassium cyanate in alcohols at 120-130 °C. This method utilizes
Efficient preparation of carbamates by Rh-catalysed oxidative carbonylation: unveiling the role of the oxidant
Iturmendi, Amaia,Iglesias, Manuel,Munárriz, Julen,Polo, Victor,Pérez-Torrente, Jesús J.,Oro, Luis A.
supporting information, p. 404 - 407 (2017/01/03)
The synthesis of a wide variety of carbamates from amines, alcohols and carbon monoxide has been achieved by means of a Rh-catalysed oxidative carbonylation reaction that uses Oxone as a stoichiometric oxidant. In-depth studies on the reaction mechanism shed light on the intimate role of Oxone in the catalytic cycle.
Copper-catalyzed carbonylation of anilines by diisopropyl azodicarboxylate for the synthesis of carbamates
Usman, Muhammad,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 107542 - 107546 (2016/11/29)
A Cu-catalyzed efficient methodology for the direct carbonylation of anilines has been developed. The N-H bond cleavage and N-C bond formation were notably achieved under solvent-free conditions and a variety of carbamates were synthesized from readily available anilines using diisopropyl azodicarboxylate (DIAD) as the carbonylating source.
PdCl2 catalyzed efficient assembly of organic azides, CO, and alcohols under mild conditions: A direct approach to synthesize carbamates
Ren, Long,Jiao, Ning
, p. 3706 - 3709 (2014/04/03)
A simple and readily available PdCl2 catalyzed carbamate synthesis method via isocyanate generation and application in situ has been developed. This chemistry provides an efficient and practical approach to synthesize carbamates from simple organic azides, CO atmosphere and alcohols. The broad scope, mild and neutral conditions, and only N2 as the byproduct make this transformation very useful. Moreover, simple examples of modification of bioactive molecules and construction of macrocycles were achieved through this protocol. This journal is the Partner Organisations 2014.
Synthesis of aryl carbamates via copper-catalyzed coupling of aryl halides with potassium cyanate
Yang, Xinye,Zhang, Yihua,Ma, Dawei
supporting information, p. 2443 - 2446,4 (2020/08/31)
Coupling of aryl halides with potassium cyanate takes place at 100-110 °C in alcohols under the catalysis of CuI (cuprous iodide) and 2-(2,6-dimethylphenylamino)-2-oxoacetic acid, affording the corresponding aryl carbamates with great diversity. Copyright
Soluble polymer based matrix for chemically active water insoluble components
-
, (2008/06/13)
This invention relates to a water soluble matrix composition comprising an anionic surfactant, a C6 to C18 alkyl pyrrolidone, urea and a water insoluble copolymer of vinyl pyrrolidone with not more than 50 wt. % of a comonomer selected from the group of an α-olefin, vinyl acetate, an acrylic or methacrylic acid ester and methacrylamide as a free flowing particulate solid which matrix is suitably mixed with a water insoluble, chemically active component, such as an agrochemical, to provide a clear sprayable film forming emulsion, such as a non-leachable film on a plant or other substrate surface. The invention also relates to the method of preparing the matrix and to the incorporation of an agrochemical concentrate and plant spray composition.
Stabilized AGchemical concentrate and use thereof
-
, (2008/06/13)
The present invention relates to the stabilization of an agricultural chemical concentrate in aqueous solution and the stabilized concentrate which comprises: (a) between about 0.1 and about 20 wt. % of a stabilizer composition comprising: (1) a C1 to C12 alkyl vinyl ether/organic acid ester copolymer, and (2) a polymer solubilizing amount of an aromatic petroleum distillate or an oxygen-containing solvent of an N-alkyl pyrrolidone, a C3 to C8 alkanol, a dibasic acid lower alkyl ester, an ether having a boiling point above 150° C. or mixtures thereof and (b) between about 80 and about 99.9 wt. % concentrate containing a water-insoluble active agricultural chemical, a solvent for said agricultural chemical and a surfactant for said concentrate. The invention also relates to the use of said stabilized concentrate.
Stabilized agchemical concentrate and use thereof
-
, (2008/06/13)
The present invention relates to the stabilization of an agricultural chemical concentrate in aqueous solution and the stabilized concentrate which comprises: (a) between about 0.1 and about 20 wt. % of a stabilizer composition comprising: (1) between about 10 and about 90 wt. % of a water-insoluble, non-crosslinked, film forming polymer, and (2) a polymer solubilizing amount of an aromatic petroleum distillate or an oxygen-containing solvent of an N-alkyl pyrrolidone, a C3 to C8 alkanol, a dibasic acid lower alkyl ester, an ether having a boiling point above 150° C. or mixtures thereof and (b) between about 80 and about 99.9 wt. % concentrate containing a water-insoluble active agricultural chemical, a solvent for said agricultural chemical and a surfactant for said concentrate. The invention also relates to the use of said stabilized concentrate.
Inert matrix composition microemulsifiable concentrate and aqueous microemulsion
-
, (2008/06/13)
What is provided herein is an inert matrix composition (IMC), and a microemulsifiable concentrate (MEC) in the form of a free-flowing, high-melting solid, suitable for making an aqueous microemulsion (AME) of an agriculturally active chemical (AAC) with dilution water. The inert matrix composition comprises about 10-50% of a C6 -C18 alkylpyrrolidone, about 10-50% of an anionic surfactant and about 10-70% of a complexing agent characterized by being an organic compound having a melting point >100° C., a molecular weight ≤500, a water solubility of at least 10% by weight, and being capable of hydrogen-bonding with the alkylpyrrolidone component of the composition. The MEC comprises the IMC and about 1-20% of the agriculturally active ingredient (AAI). Upon dilution with water an AMC is provided having a few ppm to 1% AAI.
Triazolecarboxamide herbicides
-
, (2008/06/13)
Compounds of the formula: STR1 wherein X is O or S; R and R1 are substituted or unsubstituted alkyl, alkenyl, alkynyl or cycloalkyl or R and R1 may be joined to form a heterocyclic ring; R2 is substituted or unsubstituted cycloalkyl; and n is 0, 1 or 2 are disclosed as well as their postemergence and preemergence selective herbicide use against both monocot and dicot weeds in crops such as sugarbeets, cotton, soybeans and rice.
