Machette

Iupac Name：N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide

Molecular Weight：311.85

Modify Date.: 2023-04-08 21:13

Introduction: Butachlor is a pre-emergent chloroacetanalide herbicide. Butachlor is commonly used for weed control in rice as well as cotton, maize, wheat and other crops. View more+

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1. Names and Identifiers

1.1 Name: Machette
1.2 Synonyms: 2',6'-diethyl-N-(n-butoxymethyl)-2-chloroacetanilide 2-Chloro-2,6-diethyl-N-(butoxymethyl)acetanilide 2-chloro-N-(2,6-diethylphenyl)-N-(butoxymethyl)acetamide Acetamide, N- (butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)- Acetamide, N-(butoxymethyl)-2,2-dichloro-N-(2,6-diethylphenyl)- Acetamide, N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)- Acetanilide, N- (butoxymethyl)-2-chloro-2',6'-diethyl- Aimchlor Bilchlor Butachlor butachlor [ANSI, JMAF, WSSA] Butaclor Delchlor 5G EINECS 245-477-8 GYGVN1O4&R B2 F2 Hiltachlor LAMBAST Machete Machete (herbicide) MFCD00072426 N-(Butoxymethyl)-2,2-dichloro-N-(2,6-diethylphenyl)acetamide N-(BUTOXYMETHYL)-2-CHLORO-2',6'-DIETHYLACETANILIDE n-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)-acetamid n-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide N-(Butoxymethyl)-α-chloro-N(2，6-diethylphenyl)acetamide N-(n-butoxymethyl)-2',6'-diethyl-2-chloroacetanilide N-(n-butoxymethyl)-N-chloroacetyl-2,6-diethylaniline N-butoxymethyl-2-chloro-2&rsquo,6&rsquo-diethylacetanilide PARAGRAS pillarset Pillarsete RASAYANCHLOR TRAPP

1.3 CAS No.: 23184-66-9

1.4 CID: 31677

1.5 EINECS(EC#): 245-477-8

1.6 Molecular Formula: C17H26ClNO2 (isomer)

1.7 Inchi: InChI=1S/C17H26ClNO2/c1-4-7-11-21-13-19(16(20)12-18)17-14(5-2)9-8-10-15(17)6-3/h8-10H,4-7,11-13H2,1-3H3

1.8 InChkey: HKPHPIREJKHECO-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCCOCN(C1=C(C=CC=C1CC)CC)C(=O)CCl

1.10 Isomers Smiles: CCCCOCN(C1=C(C=CC=C1CC)CC)C(=O)CCl

2. Properties

2.1 Density: 1.073

2.1 Melting point: <-5℃

2.1 Boiling point: -5°C

2.1 Refractive index: 1.536

2.1 Flash Point: 100°C

2.1 Precise Quality: 311.16500

2.1 PSA: 29.54000

2.1 logP: 4.15740

2.1 Solubility: 20mg/L(20 ºC)

2.2 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.3 AnalyticLaboratory Methods: A method is described for the analysis of water;, soil and crops for residues of the herbicide butachlor;. Residues are extracted with acetone; and light petroleum distillate. The extracts are concentrated and purified on a chromatographic column containing aluminum oxide;, silver aluminum oxide and florisil. Finally, they were quantitated by gas chromatography using an electron capture detector. The detection limits of various samples were between 0.001 and 0.015 mg/kg. The avg recoveries ranged from 79.4 to 104.6%.

2.4 Appearance: Amber liquid.

2.5 Storage: 0-6℃

2.6 Chemical Properties: Yellow Oil

2.7 Color/Form: Amber liquid
Light yellow oil

2.8 Corrosivity: No corrosion to No. 316 and No. 304 stainless steel, aluminum;, and heresite, but corrodes steel and black iron;

2.9 Decomposition: Decomposes at 165 deg C.

2.10 Odor: Faint, sweet odor

2.11 pKa: 1.20±0.50(Predicted)

2.12 Water Solubility: 23 ppm (24 C)

2.13 Stability: Indefinitely Not sensitive to light or heat.

2.14 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Agricultural Uses: Herbicide: Used for pre-emergence control of annual grasses,sedges and broadleaf weeds in rice crops. Used primarilyin Asia, South America, Europe and Africa. Not registeredfor use in the U.S. Not approved for use in EU countries.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 56 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 56 companies. For more detailed information, please visit ECHA C&L website

Of the 3 notification(s) provided by 55 of 56 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H317 (54.55%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H331 (54.55%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H400 (96.36%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (41.82%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P311, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501

3.3 Methods of Manufacturing: Butachlor; is produced by reaction of chloroacetyl chloride; with the azomethine of 2,6-diethylaniline; and formaldehyde;, followed by treatment with n-butanol;.

3.4 Usage: Butachlor is a pre-emergent chloroacetanalide herbicide. Butachlor is commonly used for weed control in rice as well as cotton, maize, wheat and other crops.

4. Safety and Handling

4.1 Symbol: GHS07, GHS09

4.1 Hazard Codes: Xn; N

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R50/53

4.1 Safety Statements: S60;S61

4.1 Octanol/Water Partition Coefficient: log Kow = 4.5

4.2 Other Preventative Measures: Avoid contact with mouth, skin or eyes, washing all parts with plenty of soap and water after handling. Keep away from children. Store in cool, dry place away from feed and foodstuffs.
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/
Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/
If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/

4.3 Hazard Declaration: H302-H400

4.3 Cleanup Methods: Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/

4.4 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.5 RIDADR: UN3082 9/PG 3

4.5 Fire Fighting Procedures: If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/

4.6 Caution Statement: P273

4.6 Formulations/Preparations: Emulsifiable concentrate, granules.
Trade names: Machete, Butanex, Butataf, Dhanuchlor, Farmachlor, Hiltaklor, Rasayanchlor, Trapp, Wiper, Ban Weed, Butamach, Butanox, Pilarsete, Vibuta. Mixtures: Bandito (+propanil), Sable (+ propanil), Vitanil (+propanil). Discontinued names mixtures: Delcut (+oxadiazon), Kusakarin (+ pyrazolynate)
Lambast
Amichlor
Mach-Mach
Weedout

4.7 WGK Germany: 3

4.7 RTECS: AE1200000

4.7 Protective Equipment and Clothing: Rubber gloves, respirator, boots, long sleeved shirt or jacket, long pants.
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

4.8 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AE1200000

CHEMICAL NAME :: Acetanilide, 2-chloro-2',6'-diethyl-N-(butoxymethyl)-

CAS REGISTRY NUMBER :: 23184-66-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C17-H26-Cl-N-O2

MOLECULAR WEIGHT :: 311.89

WISWESSER LINE NOTATION :: G1VN1O4&R B2 F2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1740 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3470 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - duck

DOSE/DURATION :: >4640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 10 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 188,311,1987

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 3

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H331 Toxic if inhaled H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026 P391 Collect spillage.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

23184-66-9Total: 3 Synthesis Route

15972-60-8 103 Suppliers

71-36-3 62 Suppliers

23184-66-9 251 Suppliers

Literatures:
Monsanto Company Patent: US4296254 A1, 1981 ;
Yield: ~80%

2568-90-3 15 Suppliers

6967-29-9 30 Suppliers

23184-66-9 251 Suppliers

Literatures:
Ledneczki, Istvan; Agocs, Pal M.; Molnar, Arpad Synlett, 2003 , # 14 p. 2255 - 2257
Yield: ~67%

6967-29-9 30 Suppliers

2351-69-1 9 Suppliers

23184-66-9 251 Suppliers

Literatures:
Synthesis, , # 11 p. 942 - 944
Yield: null

8. Precursor and Product

precursor:

6967-29-9

2351-69-1

2568-90-3

71-36-3

15972-60-8

9. Other Information

9.0 BRN: 2873811

9.1 Overview: Machette [also known as butachlor] belongs to the chloroacetanilide group herbicides. Butachlor, together with other chloroacetanilide-class herbicides including acetochlor, alachlor, metachlor, and propachlor, are the most consumed chemicals all over the world in agriculture. Butachlor [N-[butoxymethyl]-2-chloro-2’,6’-diethyl acetanilide] is a widely recommended herbicide for application in rice cultivation. It is a systemic selective pre-emergent herbicide applied on rice, tea, wheat, beans and other crops viz. corn, soybean^[1]. Butachlor is most commonly used to control a wide range of annual grass and broad leaf weeds^[2] as well as submerged macrophytes in freshwater fishponds. Butachlor was developed by Monsanto Co. [USA] in 1968 and commonly used as a post-emergence herbicide in Asia and Africa^[3]. It can be manufactured by the reaction of chloroacetyl chloride with the azomethine of 2,6-diethylaniline and formaldehyde, followed by treatment with n-butanol. Butachlor was introduced to Japan in 1973 for weed control in transplanted rice paddies.

9.2 Applications: Butachlor is a chloroacetanilide herbicide, which is used extensively all over the world as pre-emergence control of unwanted weeds. It is used for controlling a wide range of annual grass and broad leaf weeds^[2] as well as submerged macrophytes in freshwater fishponds.

9.3 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].

9.4 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].

9.5 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

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9.6 Chemical Properties: Yellow Oil

9.7 Uses: Butachlor is a pre-emergent chloroacetanalide herbicide. Butachlor is commonly used for weed control in rice as well as cotton, maize, wheat and other crops.

9.8 Uses: Pre-emergence selective anilide herbicide used to control grass and broad-leaved weeds in seeded and transplanted rice paddies.

9.9 Hazard: Moderately toxic.

9.10 Agricultural Uses: Herbicide: Used for pre-emergence control of annual grasses, sedges and broadleaf weeds in rice crops. Used primarily in Asia, South America, Europe and Africa. Not registered for use in the U.S. Not approved for use in EU countries.

9.11 Trade name: BUTANEX?; BUTANOX?; CP 53619?; HILTACHLOR?; LAMBAST?; MACHETE?; MACHETTE?; PILLARSET?; RASAYANCHLOR?; WEEDOUT?; VENDAVAL?

9.12 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.

10. Computational chemical data

Molecular Weight: 311.85g/mol
Molecular Formula: C₁₇H₂₆ClNO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 311.1652068
Monoisotopic Mass: 311.1652068
Complexity: 287
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 29.5
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB6MAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgIAAAAADAuhmEYywIMABACIAiVSUACCAAAhAAAIiAAIRIhIICLAkZHMIAhkhgDIyAcQgMAOAAACAAACAAAAAAQAAAQAAAAAAAAAAA==

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Herbicide Butachlor 60% Ec, CAS No.: 23184-66-9