709-98-8 Usage
Description
Different sources of media describe the Description of 709-98-8 differently. You can refer to the following data:
1. Propanil (3,4-dichloropropionanilide) is an acetanilide post-emergency herbicide with no residual effect. It can be prepared by reaction of 3,4-dichloroaniline with propionic acid in the presence of thionyl chloride. Propanil is in toxicity class II - moderately toxic, due to its potential to irritate eyes and skin.
Propanil functionalizes by the inhibition of RNA/protein synthesis and the inhibition of anthocyanin. Propanil is used to against numerous grasses and broad-leaved weeds in rice (mainly), potatoes, and wheat. It is typically applied aerially.
2. propanil is used
as a rice herbicide. The resistance of rice plants toward
propanil has been found in an enzyme aryl-acylamidase
that rapidly hydrolyzes the herbicide. This enzyme can be
inhibited by carbamate insecticides, and this can lead to
an increased propanil phytotoxicity (38).
References
[1] S. M. Richards, G. Y. H. McClure, T. L. Lavy, J. D. Mattice, R. J. Keller, J. Gandy (2001) Propanil (3,4-Dichloropropionanilide) Particulate Concentrations Within and Near the Residences of Families Living Adjacent to Aerially Sprayed Rice Fields, Arch. Environ. Contam. Toxicol. 41, 112–116
[2] Michael A. Kamrin (1997) Pesticide Profiles: Toxicity, Environmental Impact, and Fate
Chemical Properties
Different sources of media describe the Chemical Properties of 709-98-8 differently. You can refer to the following data:
1. Propanil is a colorless solid. The technical
product is a brown crystalline solid.
2. (Pure) Light-brown solid.
Uses
Different sources of media describe the Uses of 709-98-8 differently. You can refer to the following data:
1. Propanil is a a widely used herbicide. Propanil is used mainly to control weed growth in rice fields.
2. Postemergence herbicide, especially for rice
culture; nematocide.
3. Selective preemergence and postemergence herbicide used to control many grasses
and broad-leaved weeds in potatoes, rice and wheat.
General Description
Colorless to brown crystals. Non corrosive. Used as an herbicide.
Air & Water Reactions
Hydrolyzed by acid and alkaline media.
Reactivity Profile
Propanil is incompatible with carbamates and organophosphates.
Hazard
Toxic by ingestion and inhalation.
Agricultural Uses
Herbicide: Propanil is a post-emergence herbicide with no residual effect. It is used against numerous grasses and broadleaved weeds in rice, potatoes, and wheat. Mixing with carbamates or organophosphorus compounds is not recommended. It is also used on wheat in a mixture with MCPA. With carbaryl, it is used in citrus crops grown in sod culture. Not approved for use in EU countries (re-submitted). Registered for use in the U.S.
Trade name
Cekupropanil; DCPA; N-(3,4-Dichlorophenyl) propanamide; 3',4'-Dichlorophenyl propionanilide; 3,4-Dichloropropionanilide; 3',4'-Dichloropropionanilide; Dichloropropionanilide; Dipram; DPA; NSC 31312; Propanamide, N-(3,4-Dichlorophenyl)-; Propanide; Propionanilide, 3',4'-Dichloro-; Propionic acid, 3,4-dichloroanilide
Safety Profile
Poison by ingestion.
Moderately toxic by an unspecified route.
Mildly toxic by skin contact. Mutation data
reported. When heated to decomposition it
emits very toxic fumes of Cl and NOx.
Potential Exposure
Propanil is used as a postemergent
herbicide for rice and spring wheat. A potential danger
to those involved in the manufacture, formulation, and
application of this contact herbicide.
Environmental Fate
Biological. In the presence of suspended natural populations from unpolluted aquatic
systems, the second-order microbial transformation rate constant determined in the laboratory was reported to be 5 × 10–10 L/organisms-hour (Steen, 1991).
Soil. Propanil degrades in soil forming 3,4-dichloroaniline (Bartha, 1968; Bartha and
Pramer, 1970; Chisaka and Kearney, 1970; Bartha, 1971; Duke et al., 1991; Pothuluri et
al., 1991) which is further degraded by microbial peroxidases to 3,3′,4,4′-tetrachloroazobenzene (Bartha and Pramer, 1967; Bartha et al., 1968; Chisaka and Kearney, 1970),
3,3′,4,4′-tetrachloroazooxybenzene (Bartha and Pramer, 1970), 4-(3,4-dichloroanilo)-
3,3′,4,4′-tetrachloroazobenzene (Linke and Bartha, 1970) and 1,3-bis(3,4-dichlorophenyl)triazine (Plimmer et al., 1970a), propanoic acid, carbon dioxide and unidentified
products (Chisaka and Kearney, 1970). Evidence suggests that 3,3′,4,4′-tetrachloroazobenzene reacted with 3,4-dichloroaniline forming a new reaction product, namely 4-(3,4-
dichloroanilo)-3,3′,4′-trichloroazobenzene (Chisaka and Kearney, 1970). Under aerobic
conditions, propanil in a biologically active, organic-rich pond sediment underwent dechlorination at the para- position forming N-(3-chlorophenyl)propanamide (Stepp et al., 1985).
Residual activity in soil is limited to approximately 3–4 months (Hartley and Kidd, 1987). Plant. In rice plants, propanil is rapidly hydrolyzed via an aryl acylamidase enzyme
isolated by Frear and Still (1968) forming the nonphototoxic compounds (Ashton and
Monaco, 1991) 3,4-dichloroaniline, propionic acid (Matsunaka, 1969; Menn and Still,
1977; Hatzios, 1991) and a 3′,4′-dichloroaniline-lignin complex. This complex was identified as a metabolite of N-(3,4-dichlorophenyl)glucosylamine, a 3,4-dichloroaniline saccharide conjugate and a 3,4-dichloroaniline sugar derivative (Yi et al., 1968). In a rice
field soil under anaerobic conditions, however, propanil underwent amide hydrolysis and
dechlorination at the para position forming 3,4-dichloroaniline and m-chloroaniline (Pettigrew et al., 1985). In addition, propanil may degrade indirectly via an initial oxidation
step resulting in the formation of 3,4-dichlorolacetanilide which is further hydrolyzed to
3,4-dichloroaniline and lactic acid (Hatzios, 1991). In an earlier study, four metabolites
were identified in rice plants, two of which were positively identified as 3,4-dichloroaniline
and N-(3,4-dichlorophenyl)glucosylamine (Still, 1968).
Photolytic. Photoproducts reported from the sunlight irradiation of propanil (200 mg/L)
in distilled water were 3′-hydroxy-4′-chloropropionanilide, 3′-chloro-4′-hydroxypropionanilide, 3′,4′-dihydroxypropionanilide, 3′-chloropropionanilide, 4′-chloropropionanilide,
propionanilide, 3,4-dichloroaniline, 3-chloroaniline, propionic acid, propionamide,
3,3′,4,4′-tetrachloroazobenzene and a dark polymeric humic substance. The photolysis
products resulted from the reductive dechlorination, replacement of chlorine substituents
by hydroxyl groups, formation of propionamide, hydrolysis of the amide group and
azobenzene formation (Moilanen and Crosby, 1972). Tanaka et al. (1985) studied the
photolysis of propanil (100 mg/L) in aqueous solution using UV light (λ = 300 nm) or
sunlight. After 26 days of exposure to sunlight, propanil degraded forming a trichlorinated
biphenyl product (<1% yield) and hydrogen chloride (Tanaka et al., 1985).
Chemical/Physical. Hydrolyzes in acidic and alkaline media to propionic acid (Worthing and Hance, 1991) and 3,4-dichloroaniline (Sittig, 1985; Worthing and Hance, 1991).
The half-life of propanil in a 0.50 N sodium hydroxide solution at 20°C was determined
to be 6.6 days (El-Dib and Aly, 1976).
Waste Disposal
Hydrolysis in acidic or basic
media yields the more toxic substance, 3,4-dichloraniline,
and is not recommended.
Check Digit Verification of cas no
The CAS Registry Mumber 709-98-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 9 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 709-98:
(5*7)+(4*0)+(3*9)+(2*9)+(1*8)=88
88 % 10 = 8
So 709-98-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H9Cl2NO/c1-2-9(13)12-6-3-4-7(10)8(11)5-6/h3-5H,2H2,1H3,(H,12,13)
709-98-8Relevant articles and documents
Method for efficiently preparing 3, 4-dichlorophenyl propanamide
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Paragraph 0024-0040, (2021/09/21)
The invention discloses a method for efficiently preparing 3, 4-dichlorophenyl propionamide, which is characterized in that 3, 4-dichloroaniline, propionic acid and propionic anhydride are used as raw materials and are subjected to condensation reaction in the presence of a catalyst to synthesize the 3, 4-dichlorophenyl propionamide. The propionic anhydride is added into the raw materials and can react with water formed by reaction to form propionic acid, the effect of a dehydrating agent is achieved, the reaction speed is increased, the condensation time is shortened to 3-3.5 h, the production efficiency is greatly improved, the dehydration step after the condensation reaction is omitted, the technological process is simplified, and the cost and energy consumption are reduced. The water content of the propionic acid recovered after the condensation reaction is below 0.3%, the propionic acid can be directly applied without treatment, the reaction is still normally carried out after the propionic acid is applied, and the product is qualified. The method does not use a phosphorus-containing catalyst, does not generate three wastes, and is more in line with the construction of green chemical industry.
Synthesis method of propanil
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Paragraph 0021; 0025; 0029; 0037, (2018/11/22)
The invention discloses a synthesis method of propanil. The synthesis method comprises the following steps: firstly performing an acylation reaction on chlorobenzene as a raw material and propionyl chloride to produce p-chloropropiophenone, then performing a condensation reaction on the p-chloropropiophenone and hydroxylamine hydrochloride to produce 1-(4-chlorophenyl)-1-acetoxime, then rearranging the 1-(4-chlorophenyl)-1-acetoxime under an acidic condition, and finally chlorinating to obtain the propanil. By the synthesis method, the reaction selectivity in each step is relatively high, no obvious side reaction occurs and the reaction conversion rate is high, so that the reaction yield is high and the product purity is high; a reaction condition is mild; the raw material cost is low; a requirement on reaction equipment is low; phosphorus-containing wastewater discharge is avoided; extension and tolerance are strong; the conversion success rate from trial production to large-scale production is high, and even if the reaction is interrupted, the trial production can be continued in the later stage; and therefore, the synthesis method is suitable for industrial mass production.
Palladium-catalyzed hydroaminocarbonylation of alkenes with amines promoted by weak acid
Zhang, Guoying,Ji, Xiaolei,Yu, Hui,Yang, Lei,Jiao, Peng,Huang, Hanmin
supporting information, p. 383 - 386 (2016/01/12)
The weak acid has been identified as an efficient basicity-mask to overcome the basicity barrier imparted by aliphatic amines in the Pd-catalyzed hydroaminocarbonylation, which enables both aromatic and aliphatic amines to be applicable in the palladium-catalyzed hydroaminocarbonylation reaction. Notably, by using this protocol, the marketed herbicide of Propanil and drug of Fentanyl could be easily obtained in a one-pot manner.
