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Questions And Answer

• 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. ;

• 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. ;

• 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

  1. 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
  2. Wang S, Li H, Lin C[2013] Physiological, biochemical and growth responses of Italian ryegrass to butachlor exposure. Pestic Biochem Phys 106:21–27
  3. 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
  4. Go¨tz T, Bo¨ger P[2004] The very-long-chain fatty acid synthase is inhibited by chloroacetamides. Z Naturforsch C 59:549–553
  5. 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
  6. Wilson AGE, Takei AS[2000] Summary of toxicology studies with butachlor. J Pestici Sci 25[1]:75–83
  7. 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
  8. 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
  9. 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
  10. 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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