Pirimicarb
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Basic Info
| Common Name | Pirimicarb(F04019) |
| 2D Structure | |
| Description | Pirimicarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795) |
| FRCD ID | F04019 |
| CAS Number | 23103-98-2 |
| PubChem CID | 31645 |
| Formula | C11H18N4O2 |
| IUPAC Name | [2-(dimethylamino)-5,6-dimethylpyrimidin-4-yl] N,N-dimethylcarbamate |
| InChI Key | YFGYUFNIOHWBOB-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3 |
| Canonical SMILES | CC1=C(N=C(N=C1OC(=O)N(C)C)N(C)C)C |
| Isomeric SMILES | CC1=C(N=C(N=C1OC(=O)N(C)C)N(C)C)C |
| Synonyms |
Primicarbe
Pirimor G
PIRIMICARB
23103-98-2
Pirimor
Pyrimor
Aficida
Fernos
Aphox
Rapid
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Amines |
| Intermediate Tree Nodes | Tertiary amines - Tertiary alkylarylamines |
| Direct Parent | Dialkylarylamines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Dialkylarylamine - Aminopyrimidine - Pyrimidine - Heteroaromatic compound - Carbamic acid ester - Carbonic acid derivative - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 238.291 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Complexity | 270 |
| Monoisotopic Mass | 238.143 |
| Exact Mass | 238.143 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| 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+ | 0.9643 |
| Human Intestinal Absorption | HIA+ | 0.9849 |
| Caco-2 Permeability | Caco2+ | 0.6558 |
| P-glycoprotein Substrate | Non-substrate | 0.8108 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7697 |
| Non-inhibitor | 0.9667 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8879 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6997 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7533 |
| CYP450 2D6 Substrate | Non-substrate | 0.7451 |
| CYP450 3A4 Substrate | Substrate | 0.6093 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5623 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9352 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9440 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9014 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9837 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9153 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9636 |
| Non-inhibitor | 0.8335 | |
| AMES Toxicity | Non AMES toxic | 0.6230 |
| Carcinogens | Non-carcinogens | 0.9108 |
| Fish Toxicity | Low FHMT | 0.5053 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8133 |
| Honey Bee Toxicity | Low HBT | 0.6420 |
| Biodegradation | Not ready biodegradable | 0.8825 |
| Acute Oral Toxicity | II | 0.7128 |
| Carcinogenicity (Three-class) | Non-required | 0.6065 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.0124 | LogS |
| Caco-2 Permeability | 1.5774 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.3459 | LD50, mol/kg |
| Fish Toxicity | 1.4740 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2267 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Lentils | 0300020 | European Union | 0.2 | 16/08/2016 | |
| Edible offals (other than liver and kidney) | 1013050 | European Union | 0.05 | 16/08/2016 | |
| Laurel/bay leaves (Curry leaves, Kaffir lime leaves, Siamese cassia, Wild betel leaves, Pandan leaves,) | 0256090 | European Union | 0.8 | 16/08/2016 | |
| Tarragon (Aztec sweet herb, Epazote/Mexican tea/wormseed, Hyssop, Lemongrass, Mexican oregano, Nettle, Other species of the genus Urtica, not elsewhere mentioned, Russian tarragon, Stevia,) | 0256100 | European Union | 0.8 | 16/08/2016 | |
| Others (2) | 0256990 | European Union | 0.02* | 16/08/2016 | |
| Beans (with pods) (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, ... | 0260010 | European Union | 1.5 | 16/08/2016 | |
| Beans (without pods) (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 bean... | 0260020 | European Union | 0.7 | 16/08/2016 | |
| Peas (with pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260030 | European Union | 1.5 | 16/08/2016 | |
| Peas (without pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260040 | European Union | 0.7 | 16/08/2016 | |
| Lentils (Lupins/lupini beans, Lupins/lupini beans, Lupins/lupini beans, Lupins/lupini beans,) | 0260050 | European Union | 0.7 | 16/08/2016 | |
| Others (2) | 0260990 | European Union | 0.01* | 16/08/2016 | |
| Asparagus (Hop sprouts,) | 0270010 | European Union | 0.01* | 16/08/2016 | |
| Cardoons (Borage stems,) | 0270020 | European Union | 0.2 | 16/08/2016 | |
| Celeries | 0270030 | European Union | 0.15 | 16/08/2016 | |
| Florence fennels | 0270040 | European Union | 2 | 16/08/2016 | |
| Globe artichokes (Banana flowers,) | 0270050 | European Union | 5 | 16/08/2016 | |
| Leeks (Kurrat/Egyptian leek,) | 0270060 | European Union | 0.01* | 16/08/2016 | |
| Rhubarbs | 0270070 | European Union | 2 | 16/08/2016 | |
| Bamboo shoots (European bamboo /Japanese knotweed,) | 0270080 | European Union | 0.01* | 16/08/2016 | |
| Palm hearts | 0270090 | European Union | 0.01* | 16/08/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis and application of selective adsorbent for pirimicarb pesticides inaqueous media using allyl-β-cyclodextrin based binary functional monomers. | J Sci Food Agric | 2018 Apr | 28941229 |
| Combined exposure to low doses of pesticides causes decreased birth weights inrats. | Reprod Toxicol | 2017 Sep | 28526456 |
| Behavior of fluopyram and tebuconazole and some selected pesticides in ripeapples and consumer exposure assessment in the applied crop protection framework. | Environ Monit Assess | 2017 Jul | 28646436 |
| Simultaneous determination of pesticide residues and antioxidants in blended oil using a liquid-liquid extraction combined with dispersive solid phase extraction method. | Food Chem | 2017 Aug 15 | 28372183 |
| Multiresidue method for the quantitation of 20 pesticides in aquatic products. | Anal Bioanal Chem | 2015 Dec | 26466578 |
| Development and verification for analysis of pesticides in eggs and egg products using QuEChERS and LC-MS/MS. | Food Chem | 2015 Apr 15 | 25466149 |
| Effect of new and old pesticides on Orius armatus (Gross) - an Australian predator of western flower thrips, Frankliniella occidentalis (Pergande). | Pest Manag Sci | 2014 Mar | 23616278 |
| Combined subchronic toxicity of dichlorvos with malathion or pirimicarb in mice liver and serum: a metabonomic study. | Food Chem Toxicol | 2014 Aug | 24907623 |
| Biosensor based on multi-walled carbon nanotubes paste electrode modified withlaccase for pirimicarb pesticide quantification. | Talanta | 2013 Mar 15 | 23598106 |
| Determination of N-methylcarbamate pesticides in vegetables by poly(methacrylicacid-co-ethylene glycol dimethacrylate) monolith microextraction coupled withhigh performance liquid chromatography. | J Chromatogr B Analyt Technol Biomed Life Sci | 2013 Jun 15 | 23644497 |
| [Applicability of thresholds of toxicological concern in the chronic dietary riskassessment of transformation products of pesticide active substance]. | Zhonghua Yu Fang Yi Xue Za Zhi | 2013 Jun | 24113111 |
| Determination of organophosphorus and carbamate insecticides in fresh fruits and vegetables by high-performance thin-layer chromatography-multienzyme inhibitionassay. | J AOAC Int | 2012 Sep-Oct | 23175968 |
| Planar solid phase extraction clean-up for pesticide residue analysis in tea byliquid chromatography-mass spectrometry. | J Chromatogr A | 2012 Oct 19 | 22981507 |
| Effect of cooking process on the residues of three carbamate pesticides in rice. | Iran J Pharm Res | 2011 Winter | 24363690 |
| Multipesticide residue analysis in maize combining acetonitrile-based extraction with dispersive liquid-liquid microextraction followed by gas chromatography-massspectrometry. | J Chromatogr A | 2011 Oct 28 | 21945620 |
| Spectroscopic studies of the interaction between pirimicarb and calf thymus DNA. | Spectrochim Acta A Mol Biomol Spectrosc | 2011 Feb | 21176886 |
| Biological monitoring for exposure to pirimicarb: method development and a human oral dosing study. | Toxicol Lett | 2010 Jan 15 | 20117325 |
| Relationship of insecticide tolerance to esterase enzyme activity in Aphis pomiand Aphis spiraecola (Hemiptera: Aphididae). | J Econ Entomol | 2010 Apr | 20429451 |
| Analytical method for simultaneous determination of pesticide and veterinary drugresidues in milk by CE-MS. | Electrophoresis | 2009 May | 19384986 |
| Study on the photodegradation and microbiological degradation of pirimicarbinsecticide by using liquid chromatography coupled with ion-trap massspectrometry. | J Chromatogr A | 2009 Apr 10 | 19268958 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
- Mechanism of Action:
- Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- 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:
- 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 ]
- General Function:
- Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 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:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 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 ]