23184-66-9

Basic information

• Product Name: Machette
• Synonyms: MACHETE;MACHETE(R);machette;CP 53619;DHANUCHLOR;Hiltachlor;FARMACHLOR;BUTATAF
• CAS NO: 23184-66-9
• Molecular Formula: C₁₇H₂₆ClNO₂
• Molecular Weight: 311.85
• EINECS: 245-477-8
• Product Categories: Agro-Chemicals;HERBICIDE;A-BAlphabetic;Alpha sort;B;BI - BZ;Pesticides&Metabolites
• Mol File: 23184-66-9.mol

Chemical Properties

• Melting Point: <-5℃
• Boiling Point: 156°C (0.5 torr)
• Flash Point: 100 °C
• Appearance: Light yellow-purple/Liquid
• Density: d430 1.0695
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5388 (estimate)
• Storage Temp.: 0-6°C
• PKA: 1.20±0.50(Predicted)
• Water Solubility: 20mg/L(20 oC)
• BRN: 2873811
• CAS DataBase Reference: Machette(CAS DataBase Reference)
• NIST Chemistry Reference: Machette(23184-66-9)
• EPA Substance Registry System: Machette(23184-66-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN3082 9/PG 3
• WGK Germany: 3
• RTECS: AE1200000
• Hazardous Substances Data: 23184-66-9(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Machette is used as a pre-emergence selective anilide herbicide for controlling grass and broad-leaved weeds in seeded and transplanted rice paddies. It is also used for weed control in other crops such as cotton, maize, wheat, and soybean.
Machette is used as a herbicide for pre-emergence control of annual grasses, sedges, and broadleaf weeds in rice crops. It is primarily used in Asia, South America, Europe, and Africa. However, it is not registered for use in the U.S. and not approved for use in EU countries.
In addition to its use in agriculture, Butachlor is also used for controlling a wide range of annual grass and broad leaf weeds, as well as submerged macrophytes in freshwater fishponds.

Mode of action

The mode of action of butachlor is by inhibiting the elongase responsible for the elongation of very long-chain fatty acids and the geranylgeranyl pyrophosphate cyclization enzymes[4]. It also affects the various other metabolic processes and redox homeostasis adversely, in addition to lipid biosynthesis[5].

Warning and risk

Butachlor can cause severe toxicity. Acute toxicity Butachlor causes slight erythema and edema in rabbits when exposed to 24 h continuously[6]. It can also cause primary ocular irritation in 2 of 6 white rabbits tested. It can also cause dermal sensation, moderate-to-severe erythema with edema in guinea pig, where the dermal hypersensitivity was checked in a modified Buehler assay. Human and Animal toxicity Butachlor can cause DNA strand breaks and chromosomal aberrations in mammalian cells exhibited[7]. Butachlor can also trigger necrosis in human PBMN cells due to their oxidative role in intracellular reactive oxygen species[ROS] production, and the consequent mitochondrial dysfunction, oxidative DNA damage and chromosomal breakage[8]. Butachlor has mutagenic effects in primary rat tracheal epithelial cells and in Chinese hamster ovarian cells[9]. It is also known cause stomach tumors in rats[10].

References

Dwivedi S, Saquib Q, Al-Khedhairy AA, Musarrat J[2012] Butachlor induced dissipation of mitochondrial membrane potential, oxidative DNA damage and necrosis in human peripheral blood mononuclear cells. Toxicology 302:77–87 Wang S, Li H, Lin C[2013] Physiological, biochemical and growth responses of Italian ryegrass to butachlor exposure. Pestic Biochem Phys 106:21–27 Liu W-Y, Wang C-Y, Wang T-S, Fellers GM, Lai B-C, Kam Y-C[2011] Impacts of the herbicide butachlor on the larvae of a paddy field breeding frog[Fejervarya limnocharis] in subtropical Taiwan. Ecotoxicology 20:377–384 Go¨tz T, Bo¨ger P[2004] The very-long-chain fatty acid synthase is inhibited by chloroacetamides. Z Naturforsch C 59:549–553 Agrawal C, Sen S, Singh S, Rai S, Singh PK, Singh VK, Rai LC[2014] Comparative proteomics reveals association of early accumulated proteins in conferring butachlor tolerance in three N2-fixing Anabaena spp. J Proteomics 96:271–290 Wilson AGE, Takei AS[2000] Summary of toxicology studies with butachlor. J Pestici Sci 25[1]:75–83 Panneerselvam N, Sinha S, Shanmugam G[1999] Butachlor is cytotoxic and clastogenic and induces apoptosis in mammalian cells. Indian J Exp Biol 37:888–892 Dwivedi S, Saquib Q, Al-Khedhairy AA, Musarrat J[2012] Butachlor induced dissipation of mitochondrial membrane potential, oxidative DNA damage and necrosis in human peripheral blood mononuclear cells. Toxicology 302:77–87 Hill AB, Jefferies PR, Quistad GB, Casida JE[1997] Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes. Mutat Res 395:159–171 Xu X, Yang H, Wang L, Han B, Wang X, Lee FS-C[2007a] Analysis of chloroacetanilide herbicides in water samples by solid-phase microextraction coupled with gas chromatography–mass spectrometry. Anal Chim Acta 591:87–96

Hazard

Moderately toxic.

Trade name

BUTANEX?; BUTANOX?; CP 53619?; HILTACHLOR?; LAMBAST?; MACHETE?; MACHETTE?; PILLARSET?; RASAYANCHLOR?; WEEDOUT?; VENDAVAL?

Metabolic pathway

In vitro incubation of butachlor with rat liver fractions forms a considerable amount of glutathione conjugate, while the conjugating activity is not efficient for the kidney S9 fraction. Further biotransformation of the glutathione conjugate to mercapturate is not observed in the liver S9 fraction. Butachlor is initially conjugated with glutathione in the liver and is apparently transported to the kidneys where it is transformed to mercapturic acid.

InChI:InChI=1/C17H25Cl2NO2/c1-4-7-11-22-12-20(17(21)16(18)19)15-13(5-2)9-8-10-14(15)6-3/h8-10,16H,4-7,11-12H2,1-3H3

Upstream product

• 6967-29-9 2-chloro-2',6'-diethylacetanilide 
• 2351-69-1 1-(chloromethoxy)butane 
• 2568-90-3 di-n-butyloxymethane 
• 15972-60-8 Alachlor 
• 71-36-3 butan-1-ol 

Downstream Products

• 579-66-8 2,6-diethylaniline 

Relevant articles and documents

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.

N-Alkoxymethylation of Carboxamides Catalyzed by Br?nsted Acids

The reaction of carboxamides and dialkoxymethanes can be affected by sulfonic acids (methanesulfonic acid, p-toluene-sulfonic acid, and Nafion-H SAC-13 silica nanocomposite) to yield N-alkoxymethylcarboxamides. Various types of N-alkyl- and N-aryl-substituted acetamides can be reacted in a one-step procedure to give the products in moderate to good yields.

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.

Herbicidal compositions comprising diamino-1,3,5-triazine and chloroacetanilide herbicides and a surfactant system

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.

Sulphonylaminophenyluracil herbicides for paddy field

A herbicide for paddy field comprising sulphonylaminophenyluracil derivative as an active ingredient which is represented by the formula (I): STR1 wherein R1 represents hydrogen or methyl, R2 represents C1-5 alkyl, fluro-substituted C1-2 alkyl or C3-6 cycloalkyl, optionally applied in combination with another herbicide.

Sulfamoylphenylureas

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

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.

N-phenylpyrrolidines

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

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.