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			{{short description|Insecticide}}
			{{redirect|Capstar|the broadcasting company|iHeartMedia}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 444026892
			| Watchedfields = changed
	| Name = '''Nitenpyram'''
			| verifiedrevid = 450961985
	| ImageFile = Nitenpyram structure.png
			| Name = Nitenpyram
	| ImageSize = 200px
	| ImageName = Nitenpyram		| ImageFile = Nitenpyram Formula V1.svg
			| ImageSize =
	| IUPACName = (''E'')-''N''-(6-Chloro-3-pyridylmethyl)- ''N''-ethyl-''N'''-methyl-2-nitrovinylidenediamine
			| ImageName = Nitenpyram
	| OtherNames = Capstar
			| PIN = (''E'')-''N''<sup>1</sup>--''N''<sup>1</sup>-ethyl-''N''′<sup>1</sup>-methyl-2-nitroethene-1,1-diamine
			| OtherNames = Capstar
			| SystematicName =
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 150824-47-8
			| CASNo = 150824-47-8
	| KEGG_Ref = {{keggcite|correct| UNII_Ref = {{fdacite|correct|FDA}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| UNII = 3A837VZ81Y
			| ChemSpiderID = 2298774
	| KEGG}}
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| PubChem = 3034287
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 3A837VZ81Y		| UNII = 3A837VZ81Y
	| KEGG = C18511		| KEGG = C18511
	| ATCvet = yes		| EC_number = 601-735-5
			| ChEMBL = 259728
	| ATCCode_prefix = P53
			| ChEBI = 39170
	| ATCCode_suffix = BX02
			| Beilstein = 8489488
	}}
			| StdInChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+
			| StdInChIKey = CFRPSFYHXJZSBI-DHZHZOJOSA-N
			| SMILES = ClC1=CC=C(C=N1)CN(\C(=C\(=O))\NC)CC
			}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sub>11</sub>H<sub>15</sub>ClN<sub>4</sub>O<sub>2</sub>		| Formula = C<sub>11</sub>H<sub>15</sub>ClN<sub>4</sub>O<sub>2</sub>
			| Appearance = Pale yellow crystalline solid
	| MolarMass = 270.72 g/mol
			| MolarMass = 270.72 g/mol
	| MeltingPt = 72 °C<ref></ref>
			| MeltingPtC = 82
	}}
			| Density = 1.4 (g/mL)
			}}
			| Section3 =
			| Section4 =
			| Section5 = {{Chembox Hazards
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302}}
			| PPhrases = {{P-phrases|264|270|301+312|330|501}}
			}}
			| Section6 = {{Chembox Pharmacology
			| ATCvet = yes
			| ATCCode_prefix = P53
			| ATCCode_suffix = BX02
			}}
	}}		}}
			'''Nitenpyram''' is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect ] belonging to the class of ]s which works by blocking neural signaling of the ]. It does so by binding irreversibly to the ] (nACHr) causing a stop of the flow of ions in the ] of ]s leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.
	'''Nitenpyram''' is an ] used in ] and ] medicine to kill insect external parasites of ] and ]s.<ref></ref>
			Known under the codename TI 304 during field testing starting in 1989, the compound's first documented commercial use was in 1995 under the name "Bestguard" as an agricultural insecticide.<ref name=":0">{{Cite book|title=Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor {{!}} SpringerLink|language=en-gb|doi=10.1007/978-4-431-67933-2|year = 1999|isbn = 978-4-431-68011-6|last1 = Yamamoto|first1 = I.|last2=Casida|first2=J.E|editor-first1=Izuru |editor-first2=John E. |editor-last1=Yamamoto |editor-last2=Casida |s2cid=34374399 }}</ref> Later, nitenpyram was expanded for use as a flea treatment by the ] company under the trade name "Capstar", with a subsequent ] approval for non-food producing animals in October 2000. The current producer of nitenpyram itself is the ] chemical company. Nitenpyram continues to be used commercially, though data from market surveys indicate a significant decrease in the global usage compared to other insecticides or neonicotinoids.<ref name="Pisa">{{Cite journal|last1=Pisa|first1=Lennard|last2=Goulson|first2=Dave|last3=Yang|first3=En-Cheng|last4=Gibbons|first4=David|last5=Sánchez-Bayo|first5=Francisco|last6=Mitchell|first6=Edward|last7=Aebi|first7=Alexandre|last8=Sluijs|first8=Jeroen van der|last9=MacQuarrie|first9=Chris J. K.|title=An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 2: impacts on organisms and ecosystems|journal=Environmental Science and Pollution Research|language=en|doi=10.1007/s11356-017-0341-3 | pmc=7921077|pmid=29124633|year=2017|volume=28 |issue=10 |pages=11749–11797 |doi-access=free}}</ref>
	In veterinary medicine, it is used orally with ] and ] to control fleas (often under the trade name '''Capstar'''<ref></ref>). After ingestion, it begins killing fleas within 30 minutes and kills every adult ] on the pet within 4 hours. The effects of this pill are approximately 24-48 hours. Nitenpyram is safe to use on puppies and kittens as young as four weeks old so long as they weigh at least {{convert|2|lb|kg}}. However, panting and excitement have been noted in cats within 2 hours of Capstar administration.
			Due to its use as an insecticide and treatment of non-food producing animals, it was not deemed necessary to research the human toxicology during its main use, and, as such, not much is known about the details of nitenpyram's effects on humans. Looking at rat experiments however, the lethal amount of nitenpyram is quite high (on the order of grams) in ]s in general, whereas ]s will die with only micro or nanograms of the substance.<ref name=":1">{{Cite web|url=http://www.chemspider.com/DatasourceDetails.aspx?id=130#msds.chem.ox-nitenpyram|title=ChemSpider {{!}} Data Source Details {{!}} Oxford University Chemical Safety Data (No longer updated)|website=www.chemspider.com|access-date=2018-03-21}}</ref><ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/3034287#section=Top%20data%20...%20water%20soluble%20--%3E%20structure|title=Nitenpyram|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2018-03-21}}</ref>
	Nitenpyram is a ], which means that it is a ] that blocks the ability for neural messages to transmit through the ] of the flea causing (almost) instant death.
			Neonicotinoids, in general, have a low degradation rate when used for agricultural purposes, which allows for long-lasting protection of the crops against plant-sucking insects and indirectly the ] these insects might carry.<ref name=":0" />
	It has no long-term residual activity and therefore is not effective as a longer-term flea preventative. It is usually used to kill adult fleas quickly on an infested animal to give immediate relief for a day. It is then usually followed up with some other longer-term flea preventative to prevent reinfestation. In heavily infested animals, it can cause extreme itching as the fleas die; this almost always resolves on its own.
			== Structure ==
	It is often used as part of the protocol in treating environmental infestations.
			Nitenpyram ( (E)-N-(6-Chloro-3-pyridylmethyl)- N-ethyl-N'-methyl-2-nitrovinylidenediamine) is an open-chain ] neonicotinoid. Nitenpyram consists of a chloronicotinyl ] common to all first generation neonicotinoids and a ], the reactive group of the molecule. Nitenpyram possesses a ] pharmacophore which is known to be the main reaction site in the binding of the compound to the nACh receptor, though the specificity of the reaction is not yet fully understood for neonicotinoids in general.<ref name=":0" /> Due to its polar groups, nitenpyram is quite ], with an extremely high water solubility.
	== External links ==
	*
	*, ]
			== Mechanism of action ==
	==References==
	<references/>
			Though neonicotinoids are the largest group of insecticides used in today's agricultural world and prevalent in veterinary treatments, toxicity in general, e.g., ] and ], remains among the most controversial matters on the topic of neonicotinoids.<ref name=":11">{{Cite journal|last1=Simon-Delso|first1=N.|last2=Amaral-Rogers|first2=V.|last3=Belzunces|first3=L. P.|last4=Bonmatin|first4=J. M.|last5=Chagnon|first5=M.|last6=Downs|first6=C.|last7=Furlan|first7=L.|last8=Gibbons|first8=D. W.|last9=Giorio|first9=C.|date=2015-01-01|title=Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites|journal=Environmental Science and Pollution Research|language=en|volume=22|issue=1|pages=5–34|doi=10.1007/s11356-014-3470-y|pmid=25233913|pmc=4284386|bibcode=2015ESPR...22....5S |issn=0944-1344}}</ref> This is primarily due to the lack of concrete systematic work.<ref name=":11"/> However, studies have been done on binding phenomena between neonicotinoids and proteins, serving as an indicator to its likely behavior in human physiological conditions.<ref name=":3">{{Cite journal|last1=Ding|first1=Fei|last2=Peng|first2=Wei|title=Biological assessment of neonicotinoids imidacloprid and its major metabolites for potentially human health using globular proteins as a model|journal=Journal of Photochemistry and Photobiology B: Biology|volume=147|pages=24–36|doi=10.1016/j.jphotobiol.2015.03.010|pmid=25837412|year=2015|bibcode=2015JPPB..147...24D }}</ref>
	{{Insecticides}}
			Nitenpyram, a synthetic, ]-related chemical (neonicotinoid), has an effect on the nicotinic acetylcholine receptors and, for this reason, is considered similar to nicotine (]s). Nicotinic acetylcholine receptors are involved in the ] and ] nervous systems, present on the muscle cells where the cells from the nervous systems and the muscle cells form ]s. Variations in nicotinic-acetylcholine-receptor-binding affinity persists between species.
	]
	]
			Although nitenpyram is an agonist of nicotine for the nicotinic acetylcholine receptor, it has a much lower affinity for the nicotine acetylcholine receptor in mammals. For most insects nitenpyram is a very lethal compound. Nitenpyram will bind irreversibly to the nicotinic acetylcholine receptors, paralysing those exposed to the compound. Despite lower affinity levels, mammals can still get a nicotine poisoning response from too much neonicotinoids, hence it is of importance to provide the appropriate dose for a flea-infested pet and it's always best to consult a vet.
	]
			Nitenpyram itself and its metabolites, apart from ], have not been through in-depth toxicological investigations.<ref name=":5">{{Cite journal|last=Casida|first=John E.|date=2018-01-07|title=Neonicotinoids and Other Insect Nicotinic Receptor Competitive Modulators: Progress and Prospects|journal=Annual Review of Entomology|volume=63|issue=1|pages=125–144|doi=10.1146/annurev-ento-020117-043042|pmid=29324040|issn=0066-4170}}</ref> Similarly genotoxicity effects remain ambiguous. 6-chloronicotinic acid, according to a research group, is non-] and is not considered a developmental ].<ref name=":3" />
			== Metabolism ==
			The literature on the biotransformation of nitenpyram has been scarce. However, some studies have been conducted.<ref name=":3" /> Toxicokinetic studies have shown that human intestinal caco-2 cell line can absorb ] at a very high rate of efficiency.<ref name=":3" /><ref name=":5"/> The compound completely absorbs (>92%) from the ], rapidly distributes from the intravascular space to the peripheral tissues and organs, like the kidney, liver and lungs, proceeding biotransformation. Vets and pet owners have reported the effect of nitenpyram on flea-infested pets starting within 30 minutes after administering the neonicotinoid.<ref>{{Cite web|url=https://www.drsfostersmith.com/Rx_Info_Sheets/rx_nitenpyram.pdf|title=Rx_Info_Sheets/rx_nitenpyram|access-date=2018-03-21|archive-url=https://web.archive.org/web/20150226032656/http://www.drsfostersmith.com/Rx_Info_Sheets/rx_nitenpyram.pdf|archive-date=2015-02-26|url-status=dead}}</ref>
			Nitenpyram has been reported to metabolize into 6-chloronicotinic acid.<ref name=":3" />
			Nitenpyram in mice metabolizes into nitenpyram-COOH, nitenpyram-deschloropyridine, desmethyl-nitenpyram, nitenpyram-CN, and nitenpyram-deschloropyridine derivatives.<ref name=":5"/> The nitenpyram metabolites have not been through in-depth study. However, these metabolites can undergo oxidation reactions like the ] group into a ] group.<ref name=":5" /> 6-chloronicotinic acid can make hydrogen bonds with the hydrogen atom of amino groups.
			] enzymes in humans could generate some metabolites with greater toxicity than the parent compound, certified to cause tumors in combination with nitrates and induce genetic damage.<ref>{{Cite journal|last1=Schulz-Jander|first1=Daniel A|last2=Casida|first2=John E|title=Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction|journal=Toxicology Letters|volume=132|issue=1|pages=65–70|doi=10.1016/s0378-4274(02)00068-1|pmid=12084621|year=2002}}</ref> A precautionary approach to anything understudied would be advised, until the biotransformation is better and its effects are better studied and understood.
			== Synthesis ==
			Nitenpyram is synthesized in a multistage reaction.<ref>{{Cite patent |country=CN |number=102816112|status=patent|pubdate=2012-09-13|inventor=曾挺, 陈华, 陈共华, 潘光飞, 浙江禾本科技有限公司|title=Method for preparing pesticide nitenpyram|url=https://patents.google.com/patent/CN102816112B/en]}}</ref> The ] compound of this reaction is 2-chloro-5-chloromethylpyridine, which is also used in the preparation of other neonicotinoids such as imidacloprid. The reaction of this compound undergoes three reaction steps.
			First step, 2-chloro-5-chloromethylpyridine reacts with ] on its phase boundary acquiring the molecule ''N''-ethyl-2-chloro-5-pyridylmethyl amine.
			:]
			Synthesis can then proceed with a ] (step 2), adding the solvents ] and ] will yield the intermediate ''N''-ethyl-2-chloro-5-pyridylmethyl amine with an additional ].
			:]
			In the last step ] is added and reacts with the intermediate, replacing the pharmacophore chloride group, obtaining nitenpyram as the final end product.
			:]
			== Derivatives ==
			Being a first generation neonicotinoid, nitenpyram has been subject to a variety of modifications to its original structure, to either increase the effectiveness or specificity of the compound. One such variation is on the configuration of the reactive group/pharmacophore, from ].<ref>{{Cite journal|last1=Shao|first1=Xusheng|last2=Lu|first2=Haiyan|last3=Bao|first3=Haibo|last4=Xu|first4=Xiaoyong|last5=Liu|first5=Zewen|last6=Li|first6=Zhong|date=July 2011|title=The mode of action of a nitroconjugated neonicotinoid and the effects of target site mutation Y151S on its potency|journal=Insect Biochemistry and Molecular Biology|volume=41|issue=7|pages=440–445|doi=10.1016/j.ibmb.2011.04.005|issn=1879-0240|pmid=21549193|bibcode=2011IBMB...41..440S }}</ref> It has been shown that this type of modification can substantially increase the affinity of nitenpyram to bind to the insect nACh receptor, allowing for more directed and ecologically friendly pest control. Changes to these compounds could also help circumvent the growing resistance in nitenpyram.
			== Toxicology ==
			=== Invertebrates ===
			In a 2015 study, neonicotinoids toxicity was tested on the egg parasitoid '']''. Nitenpyram specifically was found to have the lowest toxicity, making it useful in IPM (]) treatment.<ref name="Pisa"/>
			In 2015, researchers conducted a study on the toxicity of nitenpyram on the earthworm '']. E.fetida'' is a common earthworm, which is partly responsible for the natural aeration of soil, including agricultural soil. In a 14-day exposure period, the Toxicity in ] of nitenpyram on e.fetida was found to be 4.34&nbsp;mg/kg soil, showing an inhibition of ] activity and damage to the epidermal cells and gut cells. This, however, was significantly less toxic than similar insecticides such as ], ] and ], making nitenpyram a viable substitute for many other neonicotinoids used.
			Ecologic effects of nitenpyram on bee populations is under controversy, as contradicting studies show the presence of nitenpyram in honey bees and their honey, while others do not detect nitenpyram at all.<ref>{{Cite journal|last1=Codling|first1=Garry|last2=Naggar|first2=Yahya Al|last3=Giesy|first3=John P.|last4=Robertson|first4=Albert J.|date=2018-03-01|title=Neonicotinoid insecticides in pollen, honey and adult bees in colonies of the European honey bee (Apis mellifera L.) in Egypt|journal=Ecotoxicology|language=en|volume=27|issue=2|pages=122–131|doi=10.1007/s10646-017-1876-2|pmid=29143171|bibcode=2018Ecotx..27..122C |s2cid=3917697 |issn=0963-9292}}</ref><ref>{{Cite journal|last1=Iwasa|first1=Takao|last2=Motoyama|first2=Naoki|last3=Ambrose|first3=John T.|last4=Roe|first4=R.Michael|title=Mechanism for the differential toxicity of neonicotinoid insecticides in the honey bee, Apis mellifera|journal=Crop Protection|volume=23|issue=5|pages=371–378|doi=10.1016/j.cropro.2003.08.018|year=2004|bibcode=2004CrPro..23..371I }}</ref> This, however, may be due to the decrease in usage of nitenpyram, as the global market share has been steadily decreasing.
			Nitenpyram is also commonly used in the elimination of and protection from mosquitoes. Specifically, the toxicity of nitenpyram on '']'' or the southern house mosquito was tested. The ] of the compound was found to be 0.493&nbsp;ug/ml.
			=== Vertebrates ===
			==== Aquatic animals ====
			In a study a 60-day chronic toxicity test was conducted on Chinese rare minnows ('']'') as a general fish model.<ref>{{Cite journal|last1=Hong|first1=Xiangsheng|last2=Zhao|first2=Xu|last3=Tian|first3=Xue|last4=Li|first4=Jiasu|last5=Zha|first5=Jinmiao|title=Changes of hematological and biochemical parameters revealed genotoxicity and immunotoxicity of neonicotinoids on Chinese rare minnows ( Gobiocypris rarus )|journal=Environmental Pollution|volume=233|pages=862–871|doi=10.1016/j.envpol.2017.12.036|pmid=29253827|year=2018|bibcode=2018EPoll.233..862H }}</ref> Of the neonicotinoids tested (imidacloprid, nitenpyram, and ]), nitenpyram was shown to not have much genotoxic effects or adversely affect the immune system, either through short or chronic exposure in comparison to the other compounds.
			In a similar study, nitenpyram was shown to have adverse effects on the DNA of ].<ref>{{Cite journal|last1=Yan|first1=Saihong|last2=Wang|first2=Jinhua|last3=Zhu|first3=Lusheng|last4=Chen|first4=Aimei|last5=Wang|first5=Jun|title=Toxic effects of nitenpyram on antioxidant enzyme system and DNA in zebrafish (Danio rerio) livers|journal=Ecotoxicology and Environmental Safety|volume=122|pages=54–60|doi=10.1016/j.ecoenv.2015.06.030|pmid=26202306|year=2015|bibcode=2015EcoES.122...54Y }}</ref> Enzymes inhibiting the formation of ] (ROS) were severely affected, causing oxidative DNA damage increasing with chronic exposure.
			==== Mammals ====
			The Oxford University chemical safety data documents an LD50 toxicology test on rats, both male and female, where doses are recorded as 1680&nbsp;mg and 1575&nbsp;mg per kg body weight respectively.<ref name=":1" /> As such, the overdose limits for humans and animals are quite high, reaching into grams, and the compound is seen as safe for daily use for animals. Human consumption is not recommended, though no side effects of indirect exposure (such as eating treated plants) are known to occur.
			== Degradation ==
			In the hope to understand neonicotinoid degradation in various types of water, an interesting find was made.<ref>{{Cite journal|last1=Noestheden|first1=Matthew|last2=Roberts|first2=Simon|last3=Hao|first3=Chunyan|date=2016-07-15|title=Nitenpyram degradation in finished drinking water|journal=Rapid Communications in Mass Spectrometry|volume=30|issue=13|pages=1653–1661|doi=10.1002/rcm.7581|issn=1097-0231|pmid=27321854|bibcode=2016RCMS...30.1653N }}</ref> In testing ground water, surface water and finished drinking water, researchers found degradation of nitenpyram was occurring primarily in the drinking water, which was attributed to ] of the compound. Some of these degradation products are thought to have toxic properties in non-target organisms, though the actual toxicities are not known. Nitenpyram is also degraded under the effect of ], suggesting that exposure to the sun will also degrade the compound into various degradation products.
			== Veterinary applications ==
			Nitenpyram tablets, brand name Capstar,<ref name="Rust 2003">{{cite journal |last1=Rust |first1=MK |last2=Waggoner |first2=MM |last3=Hinkle |first3=NC |last4=Stansfield |first4=D |last5=Barnett |first5=S |title=Efficacy and longevity of nitenpyram against adult cat fleas (Siphonaptera: Pulicidae) |journal=Journal of Medical Entomology |date=September 2003 |volume=40 |issue=5 |pages=678–81 |doi=10.1603/0022-2585-40.5.678 |pmid=14596282|doi-access=free }}</ref> are used to treat flea infestations in cats and dogs.<ref name="Wismer 2012">{{cite journal |last1=Wismer |first1=Tina |last2=Means |first2=Charlotte |title=Toxicology of newer insecticides in small animals |journal=Veterinary Clinics of North America: Small Animal Practice |date=March 2012 |volume=42 |issue=2 |pages=335–347 |doi=10.1016/j.cvsm.2011.12.004 |pmid=22381183}}</ref> After oral administration of the tablet the drug is readily and quickly absorbed into the blood. If a flea bites the animal it will ingest with the blood the nitenpyram. The effect of nitenpyram can be observed half an hour after the administration. At this time a high concentration in the ] can be detected and the first fleas dislodge from the pet host. A study showed that six hours after application the infestation of fleas on decreased by 96.7% for dogs and 95.2% for cats.<ref name="Rust 2003" /><ref name=":8">{{Cite journal|last1=Dobson|first1=P.|last2=Tinembart|first2=O.|last3=Fisch|first3=R. D.|last4=Junquera|first4=P.|date=2000-12-16|title=Efficacy of nitenpyram as a systemic flea adulticide in dogs and cats|journal=The Veterinary Record|volume=147|issue=25|pages=709–713|issn=0042-4900|pmid=11140929}}</ref> The adult fleas present on the hosts are severely interrupted, hence, egg production is reduced. Eggs are not directly affected by nitenpyram, only after they come out. Administering nitenpyram might have to be repeated or continued until the pest infestation has subsided. The half life of nitenpyram is around eight hours. Thus, 24 hours after treatment roughly 100% of the adult fleas were killed. Between 24 hours and 48 hours the ] is highly decreased and after 72 hours no effect could be shown anymore in studies.
			=== Side effects ===
			One observed side effect is itchiness, suspected to be from the fleas dislodging. In the five hours after the treatment it was observed that cats were grooming themselves more, i.e. scratching, biting, licking, and twitching. This will stop when the fleas have either flagged or have died.<ref name="Rust 2003" /> Other reported side effects are hyperactivity, panting, lethargy, vomiting, fever, decreased appetite, nervousness, diarrhea, difficulty breathing, salivation, incoordination, seizures, pupil dilation, increased heart rate, trembling and nervousness.<ref name=":6">{{Cite web|url=http://datasheets.scbt.com/sc-363355.pdf|title=CAPSTAR Novartis (nitenpyram)|date=2 April 2014|website=datasheets.scbt.com|access-date=12 June 2019}}</ref> In other studies no adverse effects were observed.<ref name=":8" />
			== Agricultural applications ==
			Being one of the first generation neonicotinoids, nitenpyram has seen extensible commercial use since its introduction, including pest control in agriculture. While the development of newer generation nicotinoids has caused a decrease in its use, a Worldwide Integrated Assessment (WIA) report still judged it as an ecologically viable treatment in pest control projects such as Integrated Pest management (IPM). This is due to its lower toxicity and high uptake in plants in relation to soil as opposed to other commercially used neonicotinoids.<ref name=":9">{{Cite journal|last1=Furlan|first1=Lorenzo|last2=Pozzebon|first2=Alberto|last3=Duso|first3=Carlo|last4=Simon-Delso|first4=Noa|last5=Sánchez-Bayo|first5=Francisco|last6=Marchand|first6=Patrice A.|last7=Codato|first7=Filippo|last8=Bijleveld van Lexmond|first8=Maarten|last9=Bonmatin|first9=Jean-Marc|date=2018-02-25|title=An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 3: alternatives to systemic insecticides|journal=Environmental Science and Pollution Research International|volume=28 |issue=10 |pages=11798–11820 |doi=10.1007/s11356-017-1052-5| pmc=7921064|issn=1614-7499|pmid=29478160|doi-access=free}}</ref>
			Nitenpyram has been used on many commercial crops, such as ] and ],<ref name=":9" /><ref name=":10">{{Cite journal|last1=Pisa|first1=Lennard|last2=Goulson|first2=Dave|last3=Yang|first3=En-Cheng|last4=Gibbons|first4=David|last5=Sánchez-Bayo|first5=Francisco|last6=Mitchell|first6=Edward|last7=Aebi|first7=Alexandre|last8=van der Sluijs|first8=Jeroen|last9=MacQuarrie|first9=Chris J. K.|date=2017-11-09|title=An update of the Worldwide Integrated Assessment (WIA) on systemic insecticides. Part 2: impacts on organisms and ecosystems|journal=Environmental Science and Pollution Research International|volume=28 |issue=10 |pages=11749–11797 |doi=10.1007/s11356-017-0341-3|pmc=7921077|issn=1614-7499|pmid=29124633|doi-access=free}}</ref> and can be applicated in various ways. Commonly used techniques are ] and ]. Seed treatment allows for a long lasting immunity to insects damaging the crops. The use of nitenpyram has been shown to be highly effective in protecting crops, as it is generally less toxic for non-target organisms, while killing off crop-destroying insects. While usage is still common, unlike other neonicotinoids, the global market share for nitenpyram seems to decrease based on product sale data from 2003, 2005, 2007 and 2009.<ref name=":10" /><ref name=":11"/> The reason for this is not yet fully understood, as other first generation neonicotinoids do not seem to follow the same trend, and nitenpyram is known to be less toxic to non-target organisms as compared to the compounds of the same generation.
			However, the decrease of use could possibly be explained through the formation of resistance in various insect species.<ref name=":10" /><ref>{{Cite journal|last1=Sabatino|first1=Leonardo|last2=Scordino|first2=Monica|last3=Pantò|first3=Valentina|last4=Chiappara|first4=Elena|last5=Traulo|first5=Pasqualino|last6=Gagliano|first6=Giacomo|date=2013|title=Survey of neonicotinoids and fipronil in corn seeds for agriculture|journal=Food Additives & Contaminants. Part B, Surveillance|volume=6|issue=1|pages=11–16|doi=10.1080/19393210.2012.717969|issn=1939-3229|pmid=24786619|s2cid=6769499 }}</ref> In a study conducted on nine commonly used nicotinoids, nitenpyram was found to have the greatest increase in resistance of the group within ]s, a common agricultural pest, between 2011 and 2012. A substantial increase of resistance was also found in '']'' or the cotton aphid, as compared to other compounds such as imidacloprid.
			=== Side effects ===
			Due to its use on pollen carrying plants, nitenpyram has been linked to a decrease in population of pollinators such as ]s, wild bees and ].<ref name=":11" /> Other non-target organisms, such as earthworms, are also reported to be negatively affected by nitenpyram. Plants themselves do not seem to have a negative response, as they do not possess nicotine nACh receptors.
			== References ==
			{{Reflist}}
			== External links ==
			* {{PPDB|1612}}
			]
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	]