1918-16-7

Usage

Uses

Used in Agriculture:
Propachlor is used as a selective pre-emergence herbicide for controlling most annual grasses and some broad-leaved weeds in various crops. It is effective in brassicas, corn, cotton, flax, leeks, maize, milo, onions, peas, roses, ornamental trees and shrubs, soybeans, and sugarcane.
Used in Herbicide Formulations:
Propachlor is used as a pre-emergence herbicide to combat annual grasses and broad-leaved weeds in corn, sorghum, soybeans, cotton, sugar cane, sugar beets, vegetable crops, forage crops, pasture land, and range land. It is also used to control weeds in groundnuts, leeks, onions, peas, maize, roses, and ornamental trees and shrubs.
Note: Propachlor is not approved for use in EU countries and is not registered for use in the U.S. except California.

Air & Water Reactions

Hydrolyzed by strong acid and base.

Reactivity Profile

A chloroacetanilide derivative.

Hazard

Toxic by ingestion and skin absorption.

Trade name

AATRAM?[C]; ACLID?; AI3-51503?; ALBRASS?; BEXTON?[C]; CIPA?; CP 31393?; KARTEX A?; NITICID?; RAMROD?; RAMROD? 65; SATECID?; WALLOP?[C]

Potential Exposure

Those engaged in the manufacture, formulation and application of this preemergence herbicide which is used to combat annual grasses and broad-leaved weeds in corn, soybeans, cotton, sugar cane and vegetable crops.

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 1.1 × 10–9 L/organisms-hour (Steen, 1991). Groundwater. According to the U.S. EPA (1986) propachlor has a high potential to leach to groundwater. Plant. In corn seedlings and excised leaves of corn, sorghum, sugarcane and barley, propachlor was metabolized to at least three water-soluble products. Two of these metabolites were identified as a γ-glutamylcysteine conjugate of propachlor and a glutathione conjugate of propachlor. It was postulated that both compounds were intermediate compounds in corn seedlings since they were not detected 3 days following treatment (Lamoureux et al., 1971). Photolytic. When propachlor in an aqueous ethanolic solution was irradiated with UV light (λ = 290 nm) for 5 hours, 80% decomposed to the following cyclic photo-products: N-isopropyloxindole, N-isopropyl-3-hydroxyoxindole and a spiro compound. Irradiation of propachlor in an aqueous solution containing riboflavin as a sensitizer resulted in completed degradation of the parent compound. m-Hydroxypropachlor was the only compound identified in trace amounts which formed via ring hydroxylation (Rejt? et al., 1984). Hydrolyzes under alkaline conditions forming N-isopropylaniline (Sittig, 1985) which is also a product of microbial metabolism (Novick et al., 1986). Chemical/Physical. Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax and Lewis, 1987). Hydrolyzes under alkaline conditions forming N-isopropylaniline (Sittig, 1985) which is also a product of microbial metabolism (Novicket al., 1986). Propachlor is rapidly hydrolyzed in Water (Yu et al., 1975a). The hydrolysis half-lives at 68.0°C and pH values of 3.10 and 10.20 were calculated to be 36.6 and 1.2 days, respectively (Ellington et al., 1986).

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous sub- stances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks carbon steel. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flam- mable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur).

Waste Disposal

Alkaline hydrolysis would yield N-isopropylaniline. However, incineration @ 850 ? C together with flue gas scrubbing is the preferred disposal method .

InChI:InChI=1/C11H14ClNO/c1-8(2)13(9(3)14)11-7-5-4-6-10(11)12/h4-8H,1-3H3

Upstream product

• 32622-72-3 α-Chlor-N-isopropyl-thioacetanilid 
• 62-53-3 aniline 
• 768-52-5 N-Isopropylaniline 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 3277-96-1 Dithiophosphoric acid O,O'-diethyl ester S-[(isopropyl-phenyl-carbamoyl)-methyl] ester 
• 64214-43-3 C₁₆H₂₇N₂OPS₂ 
• 64214-04-6 Methyl-thiophosphoramidic acid O-ethyl ester S-[(isopropyl-phenyl-carbamoyl)-methyl] ester 
• 72680-47-8 N-Isopropyl-2-(2-oxo-benzothiazol-3-yl)-N-phenyl-acetamide 
• 768-52-5 N-Isopropylaniline 
• 42404-06-8 hydroxy-N-isopropyl-N-phenyl-acetamide 
• 161455-97-6 2-bromo-N-isopropyl-N-phenyl-acetamide 
• 66858-64-8 2-isocyano-N-isopropylacetanilide 
• 75945-60-7 5-(N-isopropylanilino)oxazole 
• 68420-09-7 2-formamido-N-isopropylacetanilide 
• 75945-65-2 4-chloro-5-(N-isopropylanilino)oxazole 
• 75945-67-4 cis-4-(N-isopropylcarbaniloyl)-5-(p-nitrophenyl)-4,5-oxazoline 
• 75945-67-4 trans-4-(N-isopropylcarbaniloyl)-5-(p-nitrophenyl)-4,5-oxazoline 
• 1097811-66-9 C₁₅H₂₃N₃O 

Relevant academic research and scientific papers

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

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.

Thioimidazoline based compounds reverse glucocorticoid resistance in human acute lymphoblastic leukemia xenografts

Glucocorticoids form a critical component of chemotherapy regimens for pediatric acute lymphoblastic leukemia (ALL) and the initial response to glucocorticoid therapy is a major prognostic factor, where resistance is predictive of poor outcome. A high-throughput screen identified four thioimidazoline-containing compounds that reversed dexamethasone resistance in an ALL xenograft derived from a chemoresistant pediatric ALL. The lead compound (1) was synergistic when used in combination with the glucocorticoids, dexamethasone or prednisolone. Synergy was observed in a range of dexamethasone-resistant xenografts representative of B-cell precursor ALL (BCP-ALL) and T-cell ALL. We describe here the synthesis of twenty compounds and biological evaluation of thirty two molecules that explore the structure-activity relationships (SAR) of this novel class of glucocorticoid sensitizing compounds. SAR analysis has identified that the most effective dexamethasone sensitizers contain a thioimidazoline acetamide substructure with a large hydrophobic moiety on the acetamide. This journal is

Higher-Affinity Agonists of 5-HT1AR Discovered through Tuning the Binding-Site Flexibility

Discovery of high-affinity and high-selectivity agonists of 5-HT1AR has become very attractive due to their potential therapeutic effects on multiple 5-HT1AR-related psychological and neurological problems. On the basis of our previously designed lead compound FW01 (Ki = 51.9 nM, denoted as 9a in the present study), we performed large-scale molecular dynamics simulations and molecular docking operations on 5-HT1AR-9a binding. We found the flip-packing events for the headgroup of 9a, and we also found that its tail group could bind flexibly at the agonist-binding site of 5-HT1AR. By finely tuning the flip-packing phenomenon of the 9a headgroup and tuning the binding flexibility of 9a tail group, we virtually designed a series of new 9a derivatives through molecular docking operations and first-principles calculations and predicted that these newly designed 9a derivatives should be higher-affinity agonists of 5-HT1AR. The computational predictions on the new 9a derivatives have been confirmed by our wet-experimental studies as chemical synthesis, binding affinity assays, and agonistic-function assays. The consistency between our computational design and wet-experimental measurements has led to our discovery of higher-affinity agonists of 5-HT1AR, with ～50-fold increase in receptor-binding affinity and ～25-fold improvements in agonistic function. In addition, our newly designed 5-HT1AR agonists showed very high selectivity of 5-HT1AR over subtype 5-HT2AR and also over three subtypes of dopamine receptors (D1, D2, and D3). (Graph Presented).

Design, synthesis, and evaluation of indolebutylamines as a novel class of selective dopamine D3 receptor ligands

A series of indolebutylamine derivatives were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine 3 receptor. The most potent compound 11q binds to dopamine 3 receptor with a Ki value of 124 nm and displays excellent selectivity over the dopamine 1 receptor and dopamine 2 receptor. Investigation based on structural information indicates that site S182 located in extracellular loop 2 may account for high selectivity of compounds. Interaction models of the dopamine 3 receptor-11q complex and structure-activity relationships were discussed by integrating all available experimental and computational data with the eventual aim to discover potent and selective ligands to dopamine 3 receptor.

Kinetics and Mechanism of the Nucleophilic Displacement Reactions of Chloroacetanilide Herbicides: Investigation of α-Substituent Effects

The ease with which α-chloroacetanilide herbicides undergo displacement reactions with strong nucleophiles, and their recalcitrance toward weak ones, is intimately related to their herbicidal properties and environmental chemistry. In this study, we investigate the kinetics and mechanisms of nucleophilic substitution reactions of propachlor and alachlor in aqueous solution. The role played by the α-amide group was examined by including several structurally related analogs of propachlor possessing modified α substituents. The overall second-order nature of the reaction, the negative ΔS? values, the weak influence of ionic strength on reactivity, and structure-reactivity trends together support an intermolecular SN2 mechanism rather than an intramolecular reaction for α-chlomacetanilides as well as the a-chlorothioacetanilide analog of propachlor. In contrast, the α-methylene analog exhibits kinetics and a salt effect consistent with anchimeric assistance by the aniline nitrogen. Electronic interactions with the α-anilide substituent, rather than neighboring group participation, can be inferred to govern the reactivity of α-chloroacetanilides toward nucleophiles.

Halopyridyl triazolinone herbicides and herbicidal use thereof

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.

Benzhydryl compounds as herbicide antidotes

Acids, esters, amides and salts of benzhydryl compounds are antidotes for thiocarbamate and acetamide herbicides. These antidote compounds are especially effective to safen acetamide herbicides used to control grassy weeds and broadleaf weeds in rice, sorghum, corn and wheat.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

Certain ethers of certain di and trihalo-1-hydroxy-2-(fluoroalkyl)1H-imidazo(4,5-b)pyridine derivatives

Ethers of di and trihalo-1-hydroxy-2-(1,1-difluoroalkyl)-1H-imidazo(4,5-b)pyridine compounds, useful as herbicides and rodenticides.

Esters of 1-hydroxy-1H-imidazo-(4,5-b)-pyridines as herbicides

Ethers and esters of 1-hydroxy-2-(1,1-difluoroalkyl)-1H-imidazo(4,5-b)pyridine compounds, useful as herbicides.