Acifluorfen

Names

[ Name ]:
Acifluorfen

[Synonym ]:
EINECS 256-634-5
5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
Acifluorfen ∆
WNR BVQ DOR BG DXFFF
Acifluorofen
5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid
5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid
5-{[2-Chloro-4-(trifluoromethyl)phenyl]oxy}-2-nitrobenzoic acid
Benzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-
5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid
Acifluorfen
MFCD00143541

Biological Activity

[Description]:

Acifluorfen, a protoporphyrinogen oxidase (PROTOX) inhibitor herbicide, promotes the accumulation of protoporphyrin IX (PPIX), and induces tumors in the rodent liver. Acifluorfen causes strong photooxidative destruction of pigments and lipids in sensitive plant species[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

The effect of Acifluorfen on glutathione and ascorbate levels in cucumber (Cucumis sativus L.) cotyledon discs is investigated to assess the relationship between herbicide activity and endogenous antioxidants. Acifluorfen decreases the levels of glutathione and ascorbate over 50% in discs exposed to less than 1.5 hours of white light (450 microeinsteins per square meter per second). Acifluorfen also causes the rapid depletion of ascorbate in far-red light grown plants which are photosynthetically incompetent[2].

[In Vivo]

Dietary treatment with 2500 ppm Acifluorfen for up to 13 weeks increases Cyp2b10 expression in the livers of wild-type mice, but not in CAR-knockout (CARKO) mice. Microscopically, Acifluorfen treatment-induces cytotoxic changes, including hepatocellular necrosis and inflammation, and causes regenerative changes accompanied by prolonged increases in the numbers of proliferating cell nuclear antigen-positive hepatocytes in WT mice[1].

[References]

[1]. Kuwata K, et al. Involvement of Mouse Constitutive Androstane Receptor in Acifluorfen-Induced Liver Injury and Subsequent Tumor Development. Toxicol Sci. 2016;151(2):271-285.

[2]. Kenyon WH, et al. Effects of Acifluorfen on Endogenous Antioxidants and Protective Enzymes in Cucumber (Cucumis sativus L.) Cotyledons. Plant Physiol. 1985;79(3):862-866.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
422.4±45.0 °C at 760 mmHg

[ Melting Point ]:
161ºC

[ Molecular Formula ]:
C₁₄H₇ClF₃NO₅

[ Molecular Weight ]:
361.657

[ Flash Point ]:
209.2±28.7 °C

[ Exact Mass ]:
360.996490

[ PSA ]:
92.35000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.576

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DG5643070

CHEMICAL NAME :: Benzoic acid, 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitro-

CAS REGISTRY NUMBER :: 50594-66-6

LAST UPDATED :: 199701

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C14-H7-Cl-F3-N-O5

MOLECULAR WEIGHT :: 361.67

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 :: 1370 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >6900 mg/m3/4H

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1370 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3680 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 325 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - duck

DOSE/DURATION :: 2821 mg/kg

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

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,6,1991

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H318-H410

[ Precautionary Statements ]:
P273-P280-P305 + P351 + P338-P501

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R22;R38;R41;R50/53

[ Safety Phrases ]:
S24-S39-S60-S61

[ RIDADR ]:
UN 3077

[ RTECS ]:
DG5643070

[ Packaging Group ]:
III

[ HS Code ]:
2918990027

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990027

[ Summary ]:
2918990027 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:30.0%

Articles

[Determination of biphenyl ether herbicides in water using HPLC with cloud-point extraction].

Sichuan Da Xue Xue Bao. Yi Xue Ban 41(1) , 148-52, (2010)

To determine residues of multiple biphenyl ether herbicides simultaneously in water using high performance liquid chromatography (HPLC) with cloud-point extraction.The residues of eight biphenyl ether...

Increased expression of Fe-chelatase leads to increased metabolic flux into heme and confers protection against photodynamically induced oxidative stress.

Plant Mol. Biol. 86(3) , 271-87, (2014)

Fe-chelatase (FeCh, EC 4.99.1.1) inserts Fe(2+) into protoporphyrin IX (Proto IX) to form heme, which influences the flux through the tetrapyrrole biosynthetic pathway as well as fundamental cellular ...

Photochemistry and photoinduced toxicity of acifluorfen, a diphenyl-ether herbicide.

J. Environ. Qual. 31(1) , 268-74, (2002)

Photochemistry studies can be helpful in assessing the environmental fate of chemicals. Photochemical reactions lead to the formation of by-products that can exhibit different toxicological properties...