15972-60-8 Usage
Uses
Used in Agricultural Industry:
Alachlor is used as a pre-emergence herbicide for corn, soybeans, and peanuts, as well as other field crops. It is a selective systemic herbicide, absorbed by germinating shoots and roots, and works by inhibiting the activity of protease and hindering protein synthesis, resulting in the death of weeds. It is mainly used for the germination of weeds in the soil before the seedlings and is less effective for unearthed weeds.
Used in Dryland Crop Fields:
Alachlor is used as a selective herbicide for dryland bud, controlling annual grasses in the fields of dryland crops such as soybean, cotton, sugar beet, corn, peanut, and rape. It is effective against weeds like barnyard grass, Goosegrass, autumn grass, crabgrass, Setaria, and Brachiaria.
Used in Maize, Cotton, Brassicas, and Oilseed Rape Fields:
Alachlor is used preor early post-emergence to control annual grasses and many broadleaved weeds, mainly in maize, but also in cotton, brassicas, oilseed rape, peanuts, radish, soybeans, and sugar-cane.
Used in Various Crops in the United States:
Alachlor is one of the most widely used herbicides in the United States, used as an herbicide for grasses, broadleaf seeds, corn, sorghum, soybeans, peanuts, cotton, vegetables, and forage crops.
Used in Preemergence, Early Postemergence, or Soil-Incorporated Herbicide Applications:
Alachlor is used to control most annual grasses and many annual broad-leaved weeds in beans, corn, cotton, milo, peanuts, peas, soybeans, sunflower, and certain woody ornamentals.
Toxicity
Alachlor is slightly to practically nontoxic to birds, mammals, and honey bees; highly to moderately toxic to freshwater fish; and highly toxic to aquatic plants.
The acute oral LD50 for rats is 1200mg/kg. The acute percutaneous LD50 for rabbits is 5000mg/kg (13300mg/kg). Acute inhalation is LC50>1.04mg/L in rats. The non action dose of 90d in rats is 17mg/kg, and the chronic non action dose is 2.5mg/kg. It is of no teratogenicity and mutagenesis. Bronchioloalveolar tumors and liver and lung tumors can be found at 15mg/kg and 240 ~ 260mg/kg doses in mice. For carp it is LC503.72mg/L.
Preparation
Alachlor can be synthesized in the following manner:
Precaution
If there is no rain in the half month after the use of Methamide, watering or shallow mixed soil should be carried out to ensure the efficacy. But the accumulation of soil water is easy to take place.
Methamide has a certain stimulating effect on the eyes and skin. Care should be paid to the administration and dispensation. If splashed into the eyes and skin, it should be cleaned immediately.
Sorghum, millet, cucumber, melon, carrots, spinach, leeks are sensitive to alachlor and it should not be used for these plants.
Methamide should be kept at the temperature above 0℃, and the crystallization will appear at less than 0℃. The crystallized Methamide emulsion can be recovered at 15 - 20 ℃, which does not affect the efficacy of the drug. 5. Alachlor emulsion can dissolve poly vinyl chloride, acrylonitrile, butadiene, styrene plastic and other plastic products. Therefore, this kind of material can not be used as a packing container, without corrosion to metal such as aluminum, iron, stainless steel etc.
Air & Water Reactions
Hydrolyzes under strongly acidic and strongly basic conditions.
Reactivity Profile
A halogenated acetamide. 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).
Health Hazard
Alachlor is a slightly toxic herbicide. It causes slight to moderate degrees of skin irritation.
While a 90-day study on laboratory rats and dogs given diets containing low to moderate
amounts of alachlor (1–100 mg/kg/day) showed no adverse effects, a 1-year study indicated
that at a dose above 1 mg/kg/day, alachlor causes damage in the liver, spleen, and
kidney.
Trade name
AGIMIX? Araclor; ALAGAM?;
ALAGAN?; ALANEX?; ALAPAZ?, suspended;
ALAZINE?; ALATOX 480?; ALCLOR 48 LE?;
CHIMICHLOR?; LARIAT?; LASAGRIN?;
LASSAGRIN?; LASSO?; LASSO MICRO-TECH?;
METACHLOR?; PARTNER? Arachlor; PILLARZO?;
SANACHLOR?
Contact allergens
Alachlor is a herbicide. Occupational contact dermatitis was rarely observed in agricultural workers.
Safety Profile
Moderately toxic by
ingestion, skin contact, and possibly other
routes. Questionable carcinogen with
experimental carcinogenic data. Human
mutation data reported. When heated to
decomposition it emits very toxic fumes of
Cland NOx.
Potential Exposure
A chloracetanilide herbicide. In manufacture, formulation and application of this preemergence herbicide, personnel may be exposed. Its major use (99%) is as a preemergence herbicide for field crops (corn, soybeans, and peanuts, etc.).
Environmental Fate
Alachlor dissipates from soil mainly through volatilization, photodegradation, and biodegradation. Many metabolites have been identified; diethylaniline, detected in some soil studies, interacts rapidly with humic substances in the soil. A half-life in soil of 7-38 days has been reported. Under certain conditions, alachlor can leach beyond the root zone and migrate to groundwater.
Metabolic pathway
The metabolism of alachlor using in vitro incubations
with microsomal fractions prepared from liver and
nasal turbinate tissues of rat and mouse (m1) results
in conversion to 3,5-diethylbenzoquinone-4-imine via
the key intermediate of 2,6-diethylaniline, the formation of which requires catalysis by microsomal
arylamidases. 2,6-Diethylaniline is oxidized to 4-amino-
3,5-diethylphenol resulting in quinone imine by further
oxidation. Rat nasal tissue possesses high enzymatic
activity which can promote the formation of the
reactive quinone imine. A methylsulfide metabolite of
alachlor is shown to be a precursor to 2,6-
diethylaniline. The deposition of radioactivity in the rat
nasal tissue is more pronounced following oral
administration of the methylsulfide metabolite of
alachlor.
The extent of DNA adduct formation by alachlor
and its metabolites is used as a guide to deduce the
causal agent(s) in the carcinogenicity of this herbicide.
Metabolic studies (m2) indicate that 2-chloro-N-
hydroxymethoxymethyl-N-(2,6-diethylphenyl)-
acetamide is an intermediate in forming 2-chloro-N-
(2,6-diethylphenyl)acetamide and presumably
formaldehyde in the mouse liver microsomal mixed-
function oxidase system and in yielding O-glucuronide of 2-chloro-N-hydroxymethyl-N-(2,6-
diethylphenyl)acetamide in the urine of alachlor-treated
mice.
Incubation of alachlor in the presence of
glutathione (GSH) with the cytosolic fraction from rat,
mouse, and monkey (m3) produces the GSH
conjugate of alachlor as the initial metabolite. The
conjugation occurs through thiol displacement of the
chlorine atom of alachlor and is catalyzed by
glutathione S-transferase (GST). Kidney cell-free
preparations of rats and monkeys readily degrade the
alachlor GSH conjugate through the mercapturic acid
pathway to the corresponding cysteinylglycine,
cysteine, and N-acetylcysteine conjugates of alachlor.
Upon UV irradiation, 14/13C-alachlor is
dechlorinated and forms a number of intermediates
that retain the aromatic ring and carbonyl carbons.
These compounds include hydroxyalachlor,
norchloralachlor, 2' ,6'-diethylacetanilide, 2-hydroxy-
2' ,6' -diethyl-N-methylacetanilide, and a lactam. The
fungus transforms 98.6% of 14C-alachlor added to the
fermentation broth, and metabolism occurs
predominantly by benzylic hydroxylation of one of the
arylethyl side chains. Two major metabolites are
isomers of 2-chloro-N-(methoxymethyl)-N-[2-ethyl-6-(1-
hydroxyethyl)-phenyl]acetamide and 2-chloro-N-(2,6-
diethylphenyl)acetamide. The minor metabolite is
2-chloro-N-(methoxymethyl)-N-(2-vinyl-6-
ethlyphenyl)acetamide. N-Dealkylation by fungal
biotransformation is also observed.
Toxicity evaluation
Alachlor has a low persistence in soil, with a half-life ofz8 days.
The main means of degradation is by soil microbes. It has
moderate mobility in sandy and silty soils, and thus can migrate
to groundwater. The largest groundwater-testing program for
a pesticide, the National Alachlor Well Water Survey, was conducted
throughout the last half of the 1980s. More than sixmillion
private and domestic wells were tested for the presence of
alachlor. Less than 1% of all of the wells had detectable levels of
alachlor. In the wells in which the compound was detected,
concentrations ranged from 0.1 to 1.0 mg l-1, with themajority
having concentrations≈0.2mg l-1. Alachlor is relatively stable
to hydrolysis and photolysis in water, and degradation in water is
not considered as an important environmental fate process. Alachlor
appears to be persistent under aquifer biological and
geochemical conditions. This means that alachlor can appear in
groundwater years after use and can migrate with groundwater away from use areas. Alachlor contamination has resulted in loss
of untreated groundwater as a source of drinking water in Florida
and other states. The bioaccumulation factor in the channel
catfish is 5.8 times the ambient water concentration, indicating
that alachlor is not expected to accumulate appreciably in aquatic
organisms.
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Corrosive to iron and steel.
Waste Disposal
This compound is hydrolyzed under strongly acid or alkaline conditions, to chloroacetic acid, methanol, formaldehyde and 2,6-diethylanilne. Incineration is recommended as a disposal procedure. Techniques for alachlor removal from potable water have been reviewed by EPA but the data revealed no superior method. Improper disposal of pesticides is a violation of federal law. Dispose In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.
Check Digit Verification of cas no
The CAS Registry Mumber 15972-60-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,9,7 and 2 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 15972-60:
(7*1)+(6*5)+(5*9)+(4*7)+(3*2)+(2*6)+(1*0)=128
128 % 10 = 8
So 15972-60-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H20ClNO2/c1-4-11-7-6-8-12(5-2)14(11)16(10-18-3)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3
15972-60-8Relevant articles and documents
Synthesizing method for chloroacetamide compound
-
Paragraph 0046-0048, (2019/10/01)
The invention discloses a synthesizing method for a chloroacetamide compound. In a reaction kettle, a secondary amine compound is dissolved in an organic solvent, the mixture is heated for reflux, chloroacetyl chloride is added into the mixture, a reflux reaction is conducted for 0.5-20 hours, and the chloroacetamide compound is obtained. According to the synthesizing method for the chloroacetamide compound, an acid binding agent is not used, discharging of wastewater in the after-treatment process is reduced, by keeping the reflux state of the system, hydrogen chloride gas generated from thereaction is exhausted out of the system and absorbed by water outside the system, high-purity hydrochloric acid is obtained, the waste is turned into wealth, the method comes up to the production standard of safety and environment protection, and discharging of waste gas, waste water and waste residues is reduced; according to the synthesizing method for the chloroacetamide compound, few operationsteps are utilized, the reaction speed is high, the product yield is high, the purity is high, the production cost is low, and the method is safe, friendly to the environment and suitable for industrial large-scale production.
NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND
-
, (2017/08/26)
An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.
Herbicidal mixtures having a synergistic effect
-
, (2008/06/13)
PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.
Herbicidal compositions comprising diamino-1,3,5-triazine and chloroacetanilide herbicides and a surfactant system
-
, (2008/06/13)
Flowable herbicidal compositions which contain an active component combination of at least one triazine and at least one chloroacetanilide with a surfactant component. This surfactant component, which consists of an anionic compound based on a monosulfuric acid ester of alkyl or alkyphenol polyglycol ethers as well as at least one nonionic alkyl or alkylphenol polyglycol ether, gives stable dispersions of the concentrated composition and forms stable dispersions of dilutions of the compositions suitable for direct use.
Halopyridyl triazolinone herbicides and herbicidal use thereof
-
, (2008/06/13)
Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.
Sulfamoylphenylureas
-
, (2008/06/13)
The N-acylsulfamoylphenylureas of formula I below are suitable as counter-agents (antidotes or safeners) for protecting cultivated plants from the phytotoxic action of herbicides. Suitable crops are preferably cereals, soybeans, sorghum, maize and rice, and suitable herbicides are sulfonylureas, chloroacetanilides and aryloxyphenoxypropionic acid derivatives. The N-acylsulfamoylphenylureas have the formula I STR1 wherein A is a radical selected from the group STR2 R1 is C1 -C4 -alkoxy or each of R1 and R2, independently of the other, is hydrogen, C1 -C8 alkyl, C3 -C8 cycloalkyl, C3 -C6 alkenyl, C3 -C6 alkynyl, STR3 or C1 -C4 alkyl substituted by C1 -C4 alkoxy or by STR4 or R1 and R2 together form a C4 -C6 alkylene bridge, or a C4 -C6 alkylene bridge interrupted by oxygen, sulfur, SO, SO2, NH or by --N(C1 -C4 alkyl)-, R3 is hydrogen or C1 -C4 alkyl, Ra to Rh, Rx and Ry are as defined in the disclosure.
Safening mixtures of sulfonylurea and acetanilide herbicides
-
, (2008/06/13)
The disclosure herein relates to safening crops from injury by herbicidal mixtures of sulfonylurea and acetanilide herbicides by means of 5-heterocyclyl-substituted dichloroacetamide antidotes.
Substituted pyridinesulfonamide compounds or their salts, process for preparing the same, and herbicides containing the same
-
, (2008/06/13)
A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): wherein R1 is an unsubstituted or substituted alkyl group; R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.
N-phenylpyrrolidines
-
, (2008/06/13)
The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I STR1 wherein A is --COOR1, --COSR1, --COO? M≈, --CONR2 R3 or --COCl; R1 is hydrogen, C1 -C4 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl; R2 and R3 independently of one another are hydrogen, C1 -C4 alkyl or C3 -C7 cycloalkyl; or R2 and R3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C1 14 C4 alkyl; and M≈ is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN≈ (R2)3, and their isomers in optically pure or enriched form.
Safening herbicidal benzoic acid derivatives
-
, (2008/06/13)
The disclosure herein relates to the use of certain amdies of dichloroacetic acid and other compounds as safener/antidotal compounds to reduce the phytotoxicity to crop plants, especially corn, of benzoic acid-type herbicides alone or in admixture with other co-herbicidal compounds, e.g., α-haloacetamides.
