Acifluorfen

Modify Date: 2024-01-05 12:12:09

Acifluorfen Structure
Acifluorfen structure
Common Name Acifluorfen
CAS Number 50594-66-6 Molecular Weight 361.657
Density 1.6±0.1 g/cm3 Boiling Point 422.4±45.0 °C at 760 mmHg
Molecular Formula C14H7ClF3NO5 Melting Point 161ºC
MSDS Chinese USA Flash Point 209.2±28.7 °C
Symbol GHS05 GHS07 GHS09
GHS05, GHS07, GHS09
Signal Word Danger

 Use of Acifluorfen


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].

 Names

Name acifluorfen
Synonym More Synonyms

 Acifluorfen 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
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

 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
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

~%

Acifluorfen Structure

Acifluorfen

CAS#:50594-66-6

Literature: Rohm and Haas Company Patent: US4031131 A1, 1977 ;

~%

Acifluorfen Structure

Acifluorfen

CAS#:50594-66-6

Literature: Rohm and Haas Company Patent: US4395570 A1, 1983 ;

~%

Acifluorfen Structure

Acifluorfen

CAS#:50594-66-6

Literature: Rohm and Haas Company Patent: US4031131 A1, 1977 ;

~%

Acifluorfen Structure

Acifluorfen

CAS#:50594-66-6

Literature: Zeneca Limited Patent: US6342630 B1, 2002 ; Location in patent: Example 2 ;

 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%

 Articles26

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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...

 Synonyms

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
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