84087-01-4

Basic information

• Product Name: Quinclorac
• Synonyms: dichloroquinolinicacid;quincloractech;BAS 514;3,7-DICHLORO-8-QUINOLINECARBOXYLIC ACID;3,7-DICHLOROQUINOLINE-8-CARBOXYLIC ACID;3，7-Dichloroquinoline acid-8;FACET;facet 75 df
• CAS NO: 84087-01-4
• Molecular Formula: C₁₀H₅Cl₂NO₂
• Molecular Weight: 242.06
• EINECS: 402-780-1
• Product Categories: HERBICIDE
• Mol File: 84087-01-4.mol

Chemical Properties

• Melting Point: 274°C
• Boiling Point: 405.4 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: Colorless crystal
• Density: 1.7500
• Vapor Pressure: 2.27E-07mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -3.26±0.10(Predicted)
• BRN: 7761858
• CAS DataBase Reference: Quinclorac(CAS DataBase Reference)
• NIST Chemistry Reference: Quinclorac(84087-01-4)
• EPA Substance Registry System: Quinclorac(84087-01-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 2-24-37
• WGK Germany: 2
• RTECS: VB1984000
• Hazardous Substances Data: 84087-01-4(Hazardous Substances Data)

Usage

Pharmacology

The mechanism of action of quinclorac is controversial. Koo et al. (27) reported that quinclorac inhibited the incorporation of glucose into the cell wall of maize root cells. The synthesis of cellulose as well as some hemicellulose was inhibited at concentrations that inhibited whole plant growth, leading to the conclusion that quinclorac inhibits cell expansion by inhibiting glucose incorporation into the cell wall (27). These authors found that quinclorac inhibited root elongation in sensitive grasses at concentrations that inhibited cell wall biosynthesis. Cell wall biosynthesis in tolerant grasses was much less affected by quinclorac compared with sensitive grasses (28). Grossmann, on the other hand, believes that quinclorac acts as an auxinic herbicide in grasses as well as broadleaf plants, and that its herbicidal effects are due to production of cyanide (which is a byproduct of ethylene biosynthesis) and induction of the plant hormone abscisic acid (29). In this scenario, inhibition of cell wall biosynthesis would be considered a side effect, and not the primary cause of herbicidal injury. Differences in tolerance to quinclorac in this case are solely due to differences in ethylene induction, in that tolerant plants do not respond to quinclorac by synthesizing ethylene (29,30).

Metabolism

Quinclorac has been under development by BASF since 1982, and it has been marketed since 1984, as the herbicide Facet. Synthesis data are not currently available. Absorption and uptake of quinclorac is rapid, with 85% uptake in crabgrass within the first 30 minutes. Although uptake of quinclorac is rapid, translocation is generally poor, especially in sensitive plants. Tolerant species, such as Kentucky bluegrass, tend to transport more of the chemical away from the area of uptake. This may, in part, explain how tolerant plants are less affected by quinclorac. Quinclorac is metabolized very slowly in both sensitive and tolerant grass species. In leafy spurge, themajor metabolite found 7 days after foliar application of quinclorac was a pentosylglucose ester. In susceptible grasses, early symptoms of quinclorac activity include rapid chlorosis starting at the elongation zone of newly expanding leaves. This is followed by more widespread chlorosis and, eventually, necrosis. On the other hand, quinclorac seems to affect susceptible broadleaf plants as an auxinic herbicide. Symptoms in broadleaf plants begin with induction of ethylene biosynthesis and epinastic bending of shoots and leaves. This is followed by growth inhibition, chlorosis, wilting, and, finally, necrosis.

Toxicity evaluation

Quinclorac is nonflammable and noncorrosive, and it is stable in storage for at least 2 years. Quinclorac is classified as general use, with an oral LD50 > 2.61 g/kg in rats (31).

InChI:InChI=1/C10H5Cl2NO2/c11-6-3-5-1-2-7(12)8(10(14)15)9(5)13-4-6/h1-4H,(H,14,15)

Upstream product

• 87293-44-5 7-chloro-8-quinolinecarboxylic acid 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 84086-96-4 3,7-dichloro-8-chloromethyl quinoline 
• 64-19-7 acetic acid 
• 88347-01-7 3,7-dichloro-8-cyanoquinoline 
• 158353-15-2 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile 

Downstream Products

• 1463965-41-4 3,7-dichloro-N-(2-(m-tolyloxy)ethyl)quinoline-8-carboxamide 
• 84087-33-2 quinclorac methyl ester 

Relevant articles and documents

Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid

The invention discloses a method for preparing 8-quinoline carboxylic acid and derivatives thereof, which comprises the following steps: by using a compound I as a raw material, reacting with an oxidant at the temperature of 50-150 DEG C under normal pressure in a solvent under the action of a Cu-Co-X ternary composite catalyst to obtain a compound II; according to the method, the efficient Cu-Co-X ternary composite catalyst is adopted, the reaction is carried out at the temperature of 50-150 DEG C under normal pressure, the reaction condition is mild, the oxidation yield is remarkably increased, near-zero emission of three wastes is realized, the pollution problem is effectively solved, and the production cost is greatly reduced.

Preparation method of quinclorac

The invention relates to the field of herbicides, and discloses a preparation method of quinclorac, which comprises: 1) adopting an N-hydroxyphthalimide compound and azodiisobutyronitrile as catalysts, adopting oxygen as an oxidizing agent, and oxidizing 7-chloro-8-methylquinoline to obtain 7-chloro-8-quinoline carboxylic acid; and 2) by taking azodiisobutyronitrile as a catalyst, carrying out chlorination reaction on 7-chloro-8-quinoline carboxylic acid and chlorine to obtain 3,7-dichloro-8-quinoline carboxylic acid. By means of the method disclosed by the invention, the generation of a largeamount of waste acid and wastewater in a synthesis process can be reduced, and the product yield of quinclorac can be increased.

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.

Liquid phase catalytic oxidation method for preparing azethapyr

The invention discloses a liquid-phase catalytic oxidation novel method in a quinclorac synthesis process. The method comprises the steps that: in presence of a cobalt-manganese-bromine ternary complex catalyst, gas comprising oxygen molecules is delivered into a 7-chloro-8-methylquinoline chloride reaction system with aliphatic carboxylic acid as a solvent; the temperature is increased to 100-255 DEG C, and pressure of the system is maintained at 0.5-3MPa; when a reaction is finished, solid product is separated; ethanol is used for re-crystallization, such that high-content (no lower than 97%) quinclorac is obtained. Mother liquor after separation is subjected to distillation and dehydration, and can be used again. With the preparation method provided by the invention, problems of long oxidation process time, processing difficulty of product waste acid, low product purity, and the like of current oxidation processes can be effectively ameliorated.

Solid mixtures based on sulfonylureas and adjuvants

Solid mixtures comprising a) an active compound from the group consisting of the sulfonylureas, and b) an alkylpolyglucoside.

Solid mixtures based on sulfonylureas and adjuvants

A solid ixture comprising a) an active ingredient from the group of the sulfonylureas and b) an alkyl ether of a copolymer of C2-C4-alkylene oxides.

Synergistic herbicidal mixtures

PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.

Herbicidal mixtures having a synergistic effect

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.

Dichloroquinoline derivatives for use as herbicides

Dichloroquinoline derivatives of the formula STR1 are prepared as described, and are used as herbicides.