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Chemistry

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Also known as: 23184-66-9, Machette, N-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide, Bilchlor, Machete, Butaclor
Molecular Formula
C17H26ClNO2
Molecular Weight
311.8  g/mol
InChI Key
HKPHPIREJKHECO-UHFFFAOYSA-N
FDA UNII
94NU90OO5K

Butachlor
1 2D Structure

Butachlor

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide
2.1.2 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
2.1.3 InChI Key
HKPHPIREJKHECO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCOCN(C1=C(C=CC=C1CC)CC)C(=O)CCl
2.2 Other Identifiers
2.2.1 UNII
94NU90OO5K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-chloro-2',6'-diethyl-n-(butoxymethyl)acetanilide

2. Machete

2.3.2 Depositor-Supplied Synonyms

1. 23184-66-9

2. Machette

3. N-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide

4. Bilchlor

5. Machete

6. Butaclor

7. Hiltachlor

8. Delchlor 5g

9. Rasayanchlor

10. Delchlor

11. Butanex

12. Machete (herbicide)

13. N-(butoxymethyl)-2-chloro-2',6'-diethylacetanilide

14. Acetamide, N-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)-

15. 2-chloro-2',6'-diethyl-n-(butoxymethyl)acetanilide

16. Cp 53619

17. Nsc 221683

18. 2',6'-diethyl-n-butoxymethyl-2-chloroacetanilide

19. Sha 112301

20. Brn 2873811

21. 2',6'-diethyl-n-butoxymethyl-alpha-chloroacetanilide

22. N-butoxymethyl-alpha-chloro-2',6'-diethylacetanilide

23. Acetanilide, N-(butoxymethyl)-2-chloro-2',6'-diethyl-

24. 94nu90oo5k

25. Chebi:3230

26. Nsc-221683

27. Acetanilide, 2-chloro-2',6'-diethyl-n-(butoxymethyl)-

28. Amichlor

29. Pillarsete

30. Weedout

31. Mach-mach

32. Caswell No. 119b

33. Butachlor [ansi:bsi:iso]

34. Ccris 9107

35. Hsdb 6865

36. Einecs 245-477-8

37. Epa Pesticide Chemical Code 112301

38. Unii-94nu90oo5k

39. Aimchlor

40. Butachlor [iso]

41. Butachlor [mi]

42. Butachlor [hsdb]

43. Acetanilide,6'-diethyl-

44. Dsstox_cid_14402

45. Dsstox_rid_79154

46. Dsstox_gsid_34402

47. Schembl65784

48. Butachlor, Analytical Standard

49. Chembl1399036

50. Dtxsid3034402

51. Hkphpirejkheco-uhfffaoysa-

52. Hy-b2042

53. Zinc1532059

54. Butachlor 100 Microg/ml In Hexane

55. Tox21_300940

56. Nsc221683

57. Butachlor 100 Microg/ml In Methanol

58. Akos015960716

59. Butachlor 10 Microg/ml In Cyclohexane

60. Butachlor 1000 Microg/ml In Methanol

61. Ncgc00163749-01

62. Ncgc00163749-02

63. Ncgc00163749-03

64. Ncgc00163749-04

65. Ncgc00254842-01

66. As-76784

67. Cas-23184-66-9

68. Db-046099

69. Cs-0014137

70. Ft-0630494

71. Butachlor, Pestanal(r), Analytical Standard

72. 184b669

73. A816615

74. N-butoxymethyl-2-chloro-2',6'-diethylacetanilide

75. Q411950

76. W-110560

77. N-n-butoxymethyl-n-(2,6-diethylphenyl)chloroacetamide

78. N-butoxymethyl-2-chloro-2',6'- Diethyltacetanilide

79. Acetamide, N-(butoxymethyl)-2-chloro-n-(2,6- Diethylphenyl)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 311.8 g/mol
Molecular Formula C17H26ClNO2
XLogP34.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count9
Exact Mass311.1652068 g/mol
Monoisotopic Mass311.1652068 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count21
Formal Charge0
Complexity287
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Carcinogens

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)


Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)


4.2 Absorption, Distribution and Excretion

In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/

U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 55


The results of dermal penetration studies with rhesus monkeys indicate that butachlor is poorly absorbed through the skin. ... Employing a 6-hr topical exposure period, only 0.02 % of the dose was systemically absorbed during exposure to a granular formulation, and 5 % of the dose was absorbed when an EC (emulsifiable concentrate) formulation was applied.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1550


Approximately 85 % of an orally administered dose is eliminated in 48 hr; 60 % of the excretedmaterial is found in the feces and 40 % in urine.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1550


... Following a 24-hr exposure, an average butachlor quantity of approximately 5.00% of the applied dose (1.01 micrograms) was absorbed by the skin. The mean peak penetration rate was 0.7% of the applied dose per hour. The skin retained 1.40 to 8.10% of the applied butachlor.

PMID:8337702 Ademola JI et al; Toxicol Appl Pharmacol 121 (1): 78-86 (1993)


4.3 Metabolism/Metabolites

... Butachlor ... yielded 20-60 mol% formaldehyde on incubation with the mouse liver microsomal mixed function oxidase system under standard conditions.

Jacobsen NE et al; J Agric Food Chem 39 (7): 1342-50 (1991)


The metabolism of butachlor was studied in rat liver and kidney homogenates. In vitro incubation of butachlor with liver fractions (S9, microsome and cytosolic fractions) formed a considerable amount of butachlor glutathione conjugate, while the conjugating activity was not efficient for the kidney S9 fraction. There is a sex difference in the distribution of glutathione S-transferase in the liver. ... More enzyme activity was detected in the female liver microsome, while this is not the case in its cytosolic fraction. Further biotransformation of butachlor glutathione conjugate to mercapturate was not observed in the liver S9 fraction. This metabolite was further transformed to butachlor acetyl cysteine conjugate in the presence of acetyl CoA, but to butachlor cysteine conjugate in the absence of acetyl CoA.

PMID:1728663 Ou YH, Lin JK; J Toxicol Environ Health 35 (1): 19-28 (1992)


Butachlor metabolism in rats is complex due to extensive biliary excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Metabolism in rats follows three major pathways: initial conjugation with glutathione followed by mercapturic acid pathway metabolism; cytochrome P-450-mediated hydroxylation of the aromatic ring, its ethyl groups and the N- butoxymethylene group; and cleavage of the amide bonds via aryl amidase to form 2,6-diethyl aniline, which is further oxidized to 4-amino-3,5-diethylphenol.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1550


... Butachlor is metabolized to CDEPA to a much greater extent by rat liver microsomes (0.045 nmol/min/mg) than by human liver microsomes (< 0.001 nmol/min/mg).

PMID:11133395 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1240196 Coleman S et al; Environ Health Perspect 108 (12): 1151-1157 (2000)


Butachlor has known human metabolites that include 2-Chloro-N-(2,6-diethylphenyl)acetamide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


4.4 Biological Half-Life

Biological half-lives after exposure to high and low concentrations were 11.6 and 23.1 days, respectively; [HSDB]


... The biological half-lives of the three herbicides on exposure at high and low concentrations were 11.6 and 23.1 days for butachlor,

Lin K-H et al; Pestic Sci 49 (2); 178-184 (1997)


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