Pendimethalin
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Pendimethalin(F03929) |
| 2D Structure | |
| Description | Pendimethalin is a preemergent herbicide used to prevent crabgrass from germinating. Pendimethalin was included in a biocide ban proposed by the Swedish Chemicals Agency and approved by the European Parliament in January 13, 2009 (L800). |
| FRCD ID | F03929 |
| CAS Number | 40487-42-1 |
| PubChem CID | 38479 |
| Formula | C13H19N3O4 |
| IUPAC Name | 3,4-dimethyl-2,6-dinitro-N-pentan-3-ylaniline |
| InChI Key | CHIFOSRWCNZCFN-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H19N3O4/c1-5-10(6-2)14-12-11(15(17)18)7-8(3)9(4)13(12)16(19)20/h7,10,14H,5-6H2,1-4H3 |
| Canonical SMILES | CCC(CC)NC1=C(C=C(C(=C1[N+](=O)[O-])C)C)[N+](=O)[O-] |
| Isomeric SMILES | CCC(CC)NC1=C(C=C(C(=C1[N+](=O)[O-])C)C)[N+](=O)[O-] |
| Synonyms |
Stomp
PENDIMETHALIN
Pendimethaline
40487-42-1
Penoxaline
Prowl
Herbadox
Penoxalin
Phenoxalin
Accotab
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Aniline and substituted anilines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dinitroanilines |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Dinitroaniline - Nitrobenzene - Nitrotoluene - Phenylalkylamine - Nitroaromatic compound - Xylene - O-xylene - Secondary aliphatic/aromatic amine - C-nitro compound - Organic nitro compound - Organic oxoazanium - Secondary amine - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organopnictogen compound - Organic zwitterion - Amine - Organonitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 281.312 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 349 |
| Monoisotopic Mass | 281.138 |
| Exact Mass | 281.138 |
| XLogP | 5.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Nectarine | Japan | 0.05ppm | |||
| Peach | Japan | 0.05ppm | |||
| Loquat | Japan | 0.05ppm | |||
| Quince | Japan | 0.05ppm | |||
| Pear | Japan | 0.1ppm | |||
| Swedes | Britain | 0.05mg/kg | |||
| Other Small Fruit & Berries (Other Than Wild) | Britain | 0.05mg/kg | |||
| Other Herbs | Japan | 0.2ppm | |||
| Other Composite Vegetables | Japan | 0.05ppm | |||
| Other Legumes/Pulses | Japan | 0.1ppm | |||
| Milk & Dairy Produce | Britain | 0.05mg/kg | |||
| Meat, Fat & Preparations Of Meat | Britain | 0.05mg/kg | |||
| Other Cereals Do Not Include Rice | Britain | 0.05mg/kg | |||
| Rice | Britain | 0.05mg/kg | |||
| Millet | Britain | 0.05mg/kg | |||
| Buckwheat | Britain | 0.05mg/kg | |||
| Maize | Britain | 0.05mg/kg | |||
| Triticale | Britain | 0.05mg/kg | |||
| Oats | Britain | 0.05mg/kg | |||
| Sorghum | Britain | 0.05mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Morphotoxicity and cytogenotoxicity of pendimethalin in the test plant Allium cepa L. - A biomarker based study. | Chemosphere | 2018 Sep | 29753287 |
| Transchem project - Part II: Transgenerational effects of long-term exposure to pendimethalin at environmental concentrations on the early development and viral pathogen susceptibility of rainbow trout (Oncorhynchus mykiss). | Aquat Toxicol | 2018 Sep | 30025381 |
| Effect of adjuvant on pendimethalin and dimethenamid-P behaviour in soil. | J Hazard Mater | 2018 Jul 15 | 29775953 |
| Concentration/time-dependent dissipation, partitioning and plant accumulation of hazardous current-used pesticides and 2-hydroxyatrazine in sand and soil. | Chemosphere | 2018 Jul | 29621678 |
| Weed interference with peppermint (Mentha x piperita L.) and spearmint (Menthaspicata L.) crops under different herbicide treatments: effects on biomass andessential oil yield. | J Sci Food Agric | 2018 Jan | 28503740 |
| Occurrence and distribution of trifluralin, ethalfluralin, and pendimethalin insoils used for long-term intensive cotton cultivation in central Greece. | J Environ Sci Health B | 2017 Oct 3 | 28937929 |
| Effect of a non-woven fabric covering on the residual activity of pendimethalinin lettuce and soil. | Pest Manag Sci | 2017 May | 27558779 |
| Adaptive response under multiple stress exposure in fish: From the molecular toindividual level. | Chemosphere | 2017 Dec | 28869847 |
| Effects of dietary exposure to herbicide and of the nutritive quality of contaminated food on the reproductive output of Daphnia magna. | Aquat Toxicol | 2016 Oct | 27541481 |
| Effect of Soil Fumigation on Degradation of Pendimethalin and Oxyfluorfen inLaboratory and Ginger Field Studies. | J Agric Food Chem | 2016 Nov 23 | 27787973 |
| Lethal and sublethal effects of pesticides on Chrysoperla carnea larvae (Neuroptera: Chrysopidae) and the influence of rainfastness in their degradation pattern over time. | Ecotoxicology | 2016 Jul | 26975320 |
| Pesticide residue concentration in soil following conventional and Low-Input CropManagement in a Mediterranean agro-ecosystem, in Central Greece. | Sci Total Environ | 2016 Jan 15 | 26406107 |
| Analysis of banned veterinary drugs and herbicide residues in shellfish by liquid chromatography-tandem mass spectrometry (LC/MS/MS) and gas chromatography-tandem mass spectrometry (GC/MS/MS). | Mar Pollut Bull | 2016 Dec 15 | 27612928 |
| Influence of Environmental Factors, Cultural Practices, and Herbicide Applicationon Seed Germination and Emergence Ecology of Ischaemum rugosum Salisb. | PLoS One | 2015 Sep 14 | 26368808 |
| Aquatic risk assessment of priority and other river basin specific pesticides in surface waters of Mediterranean river basins. | Chemosphere | 2015 Sep | 26002046 |
| Harvest time residues of pendimethalin and oxyfluorfen in vegetables and soil in sugarcane-based intercropping systems. | Environ Monit Assess | 2015 May | 25832010 |
| Development and employment of slow-release pendimethalin formulations for thereduction of root penetration into subsurface drippers. | J Agric Food Chem | 2015 Feb 18 | 25622493 |
| Catalytic strategy for efficient degradation of nitroaromatic pesticides by usinggold nanoflower. | J Agric Food Chem | 2014 Nov 5 | 25329810 |
| Monitoring and risk assessment of pesticides in fresh omija (Schizandra chinensisBaillon) fruit and juice. | Food Chem Toxicol | 2012 Feb | 22079148 |
| Before the curtain falls: endocrine-active pesticides--a German contaminationlegacy. | Rev Environ Contam Toxicol | 2011 | 21541850 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [21115097 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d 24-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]