NP-MRD: Showing NP-Card for Acifluorfen (NP0336533)

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Record Information

Version

2.0

Created at

2024-09-11 06:44:35 UTC

Updated at

2024-09-11 06:44:35 UTC

NP-MRD ID

NP0336533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acifluorfen

Description

Acifluorfen, also known as blazer or tackle, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. Acifluorfen is an extremely weak basic (essentially neutral) compound (based on its pKa). Acifluorfen is an herbicide. Acifluorfen is a potentially toxic compound. Acifluorfen is currently classified as a B2 chemical carcinogen (probable human carcinogen). It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice. Also registered as a spot treatment for residential use along driveways, sidewalks, and patios. Acifluorfen was first documented in 1989 (PMID: 2813868). Acifluorfen has low acute toxicity via the oral, dermal, and inhalation routes of exposure, but causes severe eye irritation and moderate skin irritation (PMID: 11455817) (PMID: 11600024) (PMID: 11837431) (PMID: 2211482) (PMID: 7697001) (PMID: 8089433).

Structure

MOL SDF PDB SMILES InChI

ACJ
  Mrv0541 02241213222D          

 24 25  0  0  0  0            999 V2000
   -3.1834    0.5024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690    0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690    1.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0400    0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545   -0.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -0.7351    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.0400   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1834   -0.3226    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3256   -0.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889    0.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -1.5601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7545    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034   -0.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323   -0.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -0.7351    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2468   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -1.1476    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343   -1.4495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593   -0.0206    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 15  1  0  0  0  0
  4  6  1  0  0  0  0
  4 15  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5 15  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  2  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  CHG  2   7   1   9  -1
M  END
> <DATABASE_ID>
NP0336533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(OC2=CC=C(C=C2Cl)C(F)(F)F)=CC=C1[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)

> <INCHI_KEY>
NUFNQYOELLVIPL-UHFFFAOYSA-N

> <FORMULA>
C14H7ClF3NO5

> <MOLECULAR_WEIGHT>
361.657

> <EXACT_MASS>
360.996484661

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.436723023977628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.552993254333333

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0306774571810915

> <JCHEM_PKA_STRONGEST_BASIC>
-9.073820852743893

> <JCHEM_POLAR_SURFACE_AREA>
92.35

> <JCHEM_REFRACTIVITY>
77.65820000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acifluorfen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ACJ                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.942   0.938   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.609   1.708   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.609   3.248   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.941   1.708   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.275  -0.602   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.608   0.938   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -4.609  -1.372   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      -1.941  -1.372   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.942  -0.602   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0      -0.608  -0.602   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.726   1.708   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.060   0.938   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.609  -2.912   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.393   1.708   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.275   0.938   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.060  -0.602   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.727   0.938   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.727  -0.602   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.726  -1.372   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       3.393  -1.372   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.061  -1.372   0.000  0.00  0.00           C+0
HETATM   22  F   UNK     0       7.394  -2.142   0.000  0.00  0.00           F+0
HETATM   23  F   UNK     0       5.291  -2.706   0.000  0.00  0.00           F+0
HETATM   24  F   UNK     0       6.831  -0.038   0.000  0.00  0.00           F+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2                                                            
CONECT    4    6   15                                                       
CONECT    5    7    8   15                                                  
CONECT    6    4   10   11                                                  
CONECT    7    5    9   13                                                  
CONECT    8    5   10                                                       
CONECT    9    7                                                            
CONECT   10    6    8                                                       
CONECT   11    6   12                                                       
CONECT   12   11   14   16                                                  
CONECT   13    7                                                            
CONECT   14   12   17                                                       
CONECT   15    2    4    5                                                  
CONECT   16   12   19   20                                                  
CONECT   17   14   18                                                       
CONECT   18   17   20   21                                                  
CONECT   19   16                                                            
CONECT   20   16   18                                                       
CONECT   21   18   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid	ChEBI
5-(2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-2-nitrobenzoic acid	ChEBI
Acifluorfene	ChEBI
Blazer	ChEBI
2-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoate	Generator
5-(2-Chloro-a,a,a-trifluoro-p-tolyloxy)-2-nitrobenzoate	Generator
5-(2-Chloro-a,a,a-trifluoro-p-tolyloxy)-2-nitrobenzoic acid	Generator
5-(2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-2-nitrobenzoate	Generator
5-(2-Chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoate	Generator
5-(2-Chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid	Generator
(Sodium salt) scifluorfen	HMDB
5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate	HMDB
5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid	HMDB
5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid	HMDB
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid	HMDB
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, 9ci	HMDB
ACJ	HMDB
C14H7CLF3NO5	HMDB
Carbofluorfen	HMDB
Scifluorfen	HMDB
Tackle	HMDB
Tackle 25	HMDB
Acifluorfen, calcium salt	HMDB
Acifluorfen, potassium salt	HMDB
Acifluorfen, sodium salt	HMDB

Chemical Formula

C₁₄H₇ClF₃NO₅

Average Mass

361.6570 Da

Monoisotopic Mass

360.99648 Da

IUPAC Name

5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid

Traditional Name

acifluorfen

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(OC2=CC=C(C=C2Cl)C(F)(F)F)=CC=C1[N+]([O-])=O

InChI Identifier

InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)

InChI Key

NUFNQYOELLVIPL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Nitrobenzoate
Diaryl ether
Trifluoromethylbenzene
Nitrobenzene
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Phenol ether
Nitroaromatic compound
Benzoyl
Halobenzene
Chlorobenzene
Aryl chloride
Aryl halide
C-nitro compound
Organic nitro compound
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Allyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic oxoazanium
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
Alkyl fluoride
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:73172 )
organofluorine compound (CHEBI:73172 )
aromatic ether (CHEBI:73172 )
monocarboxylic acid (CHEBI:73172 )
organochlorine compound (CHEBI:73172 )
benzoic acids (CHEBI:73172 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.87	ALOGPS
logP	4.55	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.66 m³·mol⁻¹	ChemAxon
Polarizability	28.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037112

DrugBank ID

DB07338

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016105

KNApSAcK ID

Not Available

Chemspider ID

40113

KEGG Compound ID

Not Available

BioCyc ID

ACIFLUORFEN

BiGG ID

Not Available

Wikipedia Link

Acifluorfen

METLIN ID

Not Available

PubChem Compound

44073

PDB ID

ACJ

ChEBI ID

73172

Good Scents ID

Not Available

References

General References

Vialation D, Baglio D, Paya-Perez A, Richard C: Photochemical transformation of acifluorfen under laboratory and natural conditions. Pest Manag Sci. 2001 Apr;57(4):372-9. doi: 10.1002/ps.299. [PubMed:11455817 ]
Vulliet E, Emmelin C, Scrano L, Bufo SA, Chovelon JM, Meallier P, Grenier-Loustalot MF: Photochemical degradation of acifluorfen in aqueous solution. J Agric Food Chem. 2001 Oct;49(10):4795-800. doi: 10.1021/jf0100144. [PubMed:11600024 ]
Scrano L, Bufo SA, D'Auria M, Meallier P, Behechti A, Shramm KW: Photochemistry and photoinduced toxicity of acifluorfen, a diphenyl-ether herbicide. J Environ Qual. 2002 Jan-Feb;31(1):268-74. doi: 10.2134/jeq2002.2680. [PubMed:11837431 ]
Gennari M, Negre M, Cignetti A: Liquid chromatographic determination of acifluorfen in soil and water. J Assoc Off Anal Chem. 1990 Jul-Aug;73(4):599-601. [PubMed:2211482 ]
Quest JA, Phang W, Hamernik KL, van Gemert M, Fisher B, Levy R, Farber TM, Burnam WL, Engler R: Evaluation of the carcinogenic potential of pesticides. 1. Acifluorfen. Regul Toxicol Pharmacol. 1989 Oct;10(2):149-59. doi: 10.1016/0273-2300(89)90022-6. [PubMed:2813868 ]
Corrigall AV, Hift RJ, Adams PA, Kirsch RE: Inhibition of mammalian protoporphyrinogen oxidase by acifluorfen. Biochem Mol Biol Int. 1994 Dec;34(6):1283-9. [PubMed:7697001 ]
Andreoni V, Colombo M, Gennari M, Negre M, Ambrosoli R: Cometabolic degradation of acifluorfen by a mixed microbial culture. J Environ Sci Health B. 1994 Sep;29(5):963-87. doi: 10.1080/03601239409372912. [PubMed:8089433 ]
Fortina MG, Acquati A, Ambrosoli R: Identification of spore-forming strains involved in biodegradation of acifluorfen. Res Microbiol. 1996 Mar-Apr;147(3):193-9. doi: 10.1016/0923-2508(96)80219-1. [PubMed:8761738 ]

Showing NP-Card for Acifluorfen (NP0336533)

MOL for NP0336533 (Acifluorfen)

3D MOL for NP0336533 (Acifluorfen)

3D SDF for NP0336533 (Acifluorfen)

3D-SDF for NP0336533 (Acifluorfen)

PDB for NP0336533 (Acifluorfen)

3D PDB for NP0336533 (Acifluorfen)

SMILES for NP0336533 (Acifluorfen)

INCHI for NP0336533 (Acifluorfen)

Structure for NP0336533 (Acifluorfen)

3D Structure for NP0336533 (Acifluorfen)