Diflubenzuron
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Basic Info
| Common Name | Diflubenzuron(F05616) |
| 2D Structure | |
| Description | Insecticide, interfering with chitin deposition by oral absorption. Diflubenzuron is used on soya beans, citrus, tea, vegetables and mushrooms. Also used as an insecticide in feed for poultry and pigs and as a controlled release bolus in cattle Diflubenzuron belongs to the family of N-Phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of an urea group. |
| FRCD ID | F05616 |
| CAS Number | 35367-38-5 |
| PubChem CID | 37123 |
| Formula | C14H9ClF2N2O2 |
| IUPAC Name | N-[(4-chlorophenyl)carbamoyl]-2,6-difluorobenzamide |
| InChI Key | QQQYTWIFVNKMRW-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H9ClF2N2O2/c15-8-4-6-9(7-5-8)18-14(21)19-13(20)12-10(16)2-1-3-11(12)17/h1-7H,(H2,18,19,20,21) |
| Canonical SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC=C(C=C2)Cl)F |
| Isomeric SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC=C(C=C2)Cl)F |
| Synonyms |
Difluron
DIFLUBENZURON
35367-38-5
Dimilin
Duphacid
Larvakil
Micromite
Astonex
Dimilin G1
Dimilin G4
|
| Classifies |
Pollutant
Veterinary Drug
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | N-phenylureas |
| Intermediate Tree Nodes | N-acyl-phenylureas |
| Direct Parent | N-benzoyl-N'-phenylureas |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | N-benzoyl-n'-phenylurea - Halobenzoic acid or derivatives - 2-halobenzoic acid or derivatives - Benzoic acid or derivatives - Benzoyl - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Vinylogous halide - Urea - Carbonic acid derivative - Carboxylic acid derivative - Organic nitrogen compound - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as n-benzoyl-n'-phenylureas. These are n-acyl-phenylureas that have the acyl group substituted by a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 310.685 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 379 |
| Monoisotopic Mass | 310.032 |
| Exact Mass | 310.032 |
| XLogP | 3.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9924 |
| Human Intestinal Absorption | HIA+ | 0.9774 |
| Caco-2 Permeability | Caco2+ | 0.5292 |
| P-glycoprotein Substrate | Non-substrate | 0.8228 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7111 |
| Non-inhibitor | 0.9765 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8900 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8487 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6839 |
| CYP450 2D6 Substrate | Non-substrate | 0.8562 |
| CYP450 3A4 Substrate | Non-substrate | 0.7057 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6090 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6343 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9242 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9350 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5077 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9358 |
| Non-inhibitor | 0.8744 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.5907 |
| Fish Toxicity | High FHMT | 0.9508 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9985 |
| Honey Bee Toxicity | Low HBT | 0.9279 |
| Biodegradation | Not ready biodegradable | 0.9615 |
| Acute Oral Toxicity | III | 0.7780 |
| Carcinogenicity (Three-class) | Non-required | 0.7001 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -6.0825 | LogS |
| Caco-2 Permeability | 1.5784 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8571 | LD50, mol/kg |
| Fish Toxicity | 0.9786 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3166 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cherry | Japan | 0.07ppm | |||
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 01/09/2008 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 1 | 01/09/2008 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 2 | 01/09/2008 | |
| (a) edible peel | 0161000 | European Union | 0.05* | 01/09/2008 | |
| Kumquats (Marumi kumquats/round kumquats, Nagami kumquats/oval kumquats, Other species and hybrids of genus Fortunella, not elsewhere mentioned,) | 0161040 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0213990 | European Union | 0.05* | 01/09/2008 | |
| Onions ('Cipollotto Nocerino PDO', Pearl onions, Rakkyo/Chinese onions, Silverskin onions/pickled onions,) | 0220020 | European Union | 0.05* | 01/09/2008 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.2 | 01/09/2008 | |
| Purslanes (Agretti, Glassworts/samphires, Rock samphires, Sea asters, Sea lavenders, Winter purslanes/miner's lettuces, Karkallas/Hottentot figs/Iceplant leaves,) | 0252020 | European Union | 0.05* | 01/09/2008 | |
| Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves... | 0256030 | European Union | 0.2 | 01/09/2008 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 0.2 | 01/09/2008 | |
| Wild fungi (Ceps/porcino mushrooms, Chanterelles, Hedgehog mushrooms, Horns of plenty/black trumpets, Morels, Périgord black truffles, Piemont white truffles, Saint George's mushrooms, Scotch bonne... | 0280020 | European Union | 2 | 01/09/2008 | |
| Beans (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, Ervils/lenti... | 0300010 | European Union | 0.05* | 01/09/2008 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.05* | 01/09/2008 | |
| Sugar beet roots | 0900010 | European Union | 0.05* | 01/09/2008 | |
| Sugar canes (Agave leaves, Sweet sorghum canes,) | 0900020 | European Union | 0.05* | 01/09/2008 | |
| (b) bovine (American buffalo, Banteng, Buffalo, European buffalo/wisent, Gayal, Yak (domestic), Zebu, Hybrids of genera Bison, Bos, Bubalus and Poëphagus,) | 1012000 | European Union | 0.1 | 01/09/2008 | |
| Terrestrial invertebrate animals (Earthworms, Insects, Snails, Other terrestrial invertebrate animals, Other edible snails not belonging to the genus Helix,) | 1060000 | European Union | 0.05* | 01/09/2008 | |
| Burdock | Japan | 0.5ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Metabolism of diflubenzuron in lizard (Eremias argus) and comparative toxicity of diflubenzuron and its metabolite. | J Agric Food Chem | 2018 Oct 22 | 30346759 |
| Rapid multiresidue determination of pesticides in livestock muscle and livertissue via modified QuEChERS sample preparation and LC-MS/MS. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Jul | 28406073 |
| Ultrasound-assisted, hybrid ionic liquid, dispersive liquid-liquidmicroextraction for the determination of insecticides in fruit juices based onpartition coefficients. | J Sep Sci | 2017 Sep | 28675591 |
| Exploration of the phycoremediation potential of Laminaria digitata towards diflubenzuron, lindane, copper and cadmium in a multitrophic pilot-scale experiment. | Food Chem Toxicol | 2017 Jun | 28161465 |
| Richness and density of aquatic benthic macroinvertebrates after exposure tofungicides and insecticides in rice paddy fields. | An Acad Bras Cienc | 2017 Jan-Mar | 28273247 |
| Exposing Northern shrimp (Pandalus borealis) to fish feed containing theantiparasitic drug diflubenzuron caused high mortality during molting. | J Toxicol Environ Health A | 2017 | 28876214 |
| Study on the simultaneous determination of seven benzoylurea pesticides in Oolongtea and their leaching characteristics during infusing process by HPLC-MS/MS. | Food Chem | 2014 Jan 15 | 24054259 |
| Residue behaviour of six pesticides in button crimini during home canning. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24761834 |
| Simultaneous determination of 36 pesticide residues in spinach and cauliflower byLC-MS/MS using multi-walled carbon nanotubes-based dispersive solid-phaseclean-up. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2014 | 24350649 |
| Feed-through insecticides for the control of the sand fly Phlebotomus argentipes. | Med Vet Entomol | 2013 Mar | 23278322 |
| Efficacy of insect growth regulators as grain protectants against twostored-product pests in wheat and maize. | J Food Prot | 2012 May | 22564945 |
| Determination of the insecticide diflubenzuron in mushrooms by kinetic method andhigh-performance liquid chromatographic method. | J Environ Sci Health B | 2010 Nov | 20954045 |
| Synthesis and insecticidal activity of heptafluoroisopropyl-containingbenzoylphenylurea structures. | J Agric Food Chem | 2010 Mar 10 | 20014763 |
| Laboratory evaluation of diflubenzuron as a feed-through for control of immature sand flies (Diptera: Psychodidae). | J Med Entomol | 2007 Mar | 17427683 |
| Ovicidal and larvicidal effectiveness of insecticides applied by dipping appleson the small fruit tortrix Grapholita lobarzewskii. | Pest Manag Sci | 2007 Jul | 17503401 |
| Synthesis and insecticidal evaluation of propesticides of benzoylphenylureas. | J Agric Food Chem | 2005 Jan 12 | 15631506 |
| CYP superfamily perturbation by diflubenzuron or acephate in different tissues ofCD1 mice. | Food Chem Toxicol | 2005 Jan | 15582210 |
| Determination of poultry feed-through insecticide activity in an in vivoanticoccidial assay. | J Parasitol | 2004 Apr | 15165074 |
| Horizontal and trophic transfer of diflubenzuron and fipronil among grasshoppers (Melanoplus sanguinipes) and between grasshoppers and darkling beetles(Tenebrionidae). | Arch Environ Contam Toxicol | 2003 Apr | 12712298 |
| Acute toxicity of locust insecticides to two indigenous invertebrates from Sahelian temporary ponds. | Ecotoxicol Environ Saf | 2001 Jan | 11161680 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 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:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 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 ]