Global InformationAclonifen information
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| Names | |
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| IUPAC name
2-chloro-6-nitro-3-phenoxyaniline
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| Other names
RPA099795
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| Identifiers | |
CAS Number
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3D model (JSmol)
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| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.070.619 |
| EC Number |
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PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties[1] | |
Chemical formula
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C12H9ClN2O3 |
| Molar mass | 264.67 g·mol−1 |
| Density | 1.46 g/cm3 |
| Melting point | 81.2 °C (178.2 °F; 354.3 K) |
Solubility in water
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1.4 mg/L (20 °C) |
| log P | 4.37 |
| Acidity (pKa) | -3.15 |
| Pharmacology | |
| Legal status |
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| Hazards | |
| GHS labelling:[2] | |
Pictograms
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Signal word
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Warning |
Hazard statements
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H317, H351, H410 |
Precautionary statements
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P201, P202, P261, P272, P273, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P391, P405, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching (removal of leaf colour) and the compound includes chemical features (a nitro group attached to a diphenyl ether) that are known to result in PPO effects, as seen with acifluorfen, for example.[1][3][4] In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.[5][6]
- ^ a b Pesticide Properties Database. "Aclonifen". University of Hertfordshire.
- ^ PubChem Database. "Aclonifen".
- ^ Kılınç, Özgür; Reynaud, Stéphane; Perez, Laurent; Tissut, Michel; Ravanel, Patrick (February 2009). "Physiological and biochemical modes of action of the diphenylether aclonifen". Pesticide Biochemistry and Physiology. 93 (2): 65–71. doi:10.1016/j.pestbp.2008.11.008.
- ^ Dayan, Franck E; Owens, Daniel K; Duke, Stephen O (2012-01-09). "Rationale for a natural products approach to herbicide discovery". Pest Management Science. 68 (4). Society of Chemical Industry (Wiley): 519–528. doi:10.1002/ps.2332. ISSN 1526-498X. PMID 22232033. S2CID 10841777.
- ^ Kahlau, Sabine; Schröder, Florian; Freigang, Jörg; Laber, Bernd; Lange, Gudrun; Passon, Daniel; Kleeßen, Sabrina; Lohse, Marc; Schulz, Arno; von Koskull-Döring, Pascal; Klie, Sebastian; Gille, Sascha (October 2020). "Aclonifen targets solanesyl diphosphate synthase, representing a novel mode of action for herbicides". Pest Management Science. 76 (10): 3377–3388. doi:10.1002/ps.5781. PMID 32034864. S2CID 211063448.
- ^ Pinho, Bárbara (2021-04-06). "The growing problem of pesticide resistance". Chemistry World.