Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect
neurotoxin
Neurotoxins are toxins that are destructive to nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insultsSpencer 2000 that can adversely affect function in both developing and mature ner ...
belonging to the class of
neonicotinoid
Neonicotinoids (sometimes shortened to neonics ) are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.
The neonicotinoid family includes acetamiprid, clothianidin, dinote ...
s which works by blocking neural signaling of the
central nervous system
The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...
. It does so by binding irreversibly to the
nicotinic acetylcholine receptor
Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ne ...
(nACHr) causing a stop of the flow of ions in the
postsynaptic membrane
Chemical synapses are biological junctions through which neurons' signals can be sent to each other and to non-neuronal cells such as those in muscles or glands. Chemical synapses allow neurons to form circuits within the central nervous syste ...
of
neuron
A neuron, neurone, or nerve cell is an electrically excitable cell that communicates with other cells via specialized connections called synapses. The neuron is the main component of nervous tissue in all animals except sponges and placozoa. N ...
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.
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.
Later, nitenpyram was expanded for use as a flea treatment by the
Novartis
Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and
Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-loc ...
company under the trade name "Capstar", with a subsequent
FDA
The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
approval for non-food producing animals in October 2000. The current producer of nitenpyram itself is the
Sumitomo
The is one of the largest Japanese ''keiretsu'', or business groups, founded by Masatomo Sumitomo (1585-1652) around 1615 during the early Edo period.
History
The Sumitomo Group traces its roots to a bookshop in Kyoto founded circa 1615 by Masa ...
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.
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
mammal
Mammals () are a group of vertebrate animals constituting the class Mammalia (), characterized by the presence of mammary glands which in females produce milk for feeding (nursing) their young, a neocortex (a region of the brain), fur or ...
s in general, whereas
invertebrate
Invertebrates are a paraphyletic group of animals that neither possess nor develop a vertebral column (commonly known as a ''backbone'' or ''spine''), derived from the notochord. This is a grouping including all animals apart from the chordate ...
s will die with only micro or nanograms of the substance.
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
plant diseases
Plant pathology (also phytopathology) is the scientific study of diseases in plants caused by pathogens (infectious organisms) and environmental conditions (physiological factors). Organisms that cause infectious disease include fungus, fung ...
these insects might carry.
Structure
Nitenpyram ( (E)-N-(6-Chloro-3-pyridylmethyl)- N-ethyl-N'-methyl-2-nitrovinylidenediamine) is an open-chain
chloropyridyl neonicotinoid. Nitenpyram consists of a chloronicotinyl
heterocyclic group common to all first generation neonicotinoids and a
pharmacophore
300px, An example of a pharmacophore model.
A pharmacophore is an abstract description of molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule. IUPAC defines a pharmacophore to be "an ensemble o ...
, the reactive group of the molecule. Nitenpyram possesses a
nitroamine
Nitroamines are organic compounds containing a nitro group bonded to an amine. The parent inorganic compound, where R1 = R2 = H, is nitramide
Nitramide is a chemical compound with the molecular formula H2NNO2. Organyl derivatives of nitramide, ...
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.
Due to its polar groups, nitenpyram is quite
hydrophilic
A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press.
In contrast, hydrophobes are no ...
, with an extremely high water solubility.
Mechanism of action
Though neonicotinoids are the largest group of insecticides used in today's agricultural world and prevalent in veterinary treatments, toxicity in general, e.g.,
genotoxicity Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, but some genotoxic sub ...
and
biotransformation Biotransformation is the biochemical modification of one chemical compound or a mixture of chemical compounds. Biotransformations can be conducted with whole cells, their lysates, or purified enzymes. Increasingly, biotransformations are effected w ...
, remains among the most controversial matters on the topic of neonicotinoids.
This is primarily due to the lack of concrete systematic work.
However, studies have been done on binding phenomena between neonicotinoids and proteins, serving as an indicator to its likely behavior in human physiological conditions.
Nitenpyram, a synthetic,
nicotine
Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
-related chemical (neonicotinoid), has an effect on the nicotinic acetylcholine receptors and, for this reason, is considered similar to nicotine (
agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
s). Nicotinic acetylcholine receptors are involved in the
sympathetic and
parasympathetic
The parasympathetic nervous system (PSNS) is one of the three divisions of the autonomic nervous system, the others being the sympathetic nervous system and the enteric nervous system. The enteric nervous system is sometimes considered part of t ...
nervous systems, present on the muscle cells where the cells from the nervous systems and the muscle cells form
synapse
In the nervous system, a synapse is a structure that permits a neuron (or nerve cell) to pass an electrical or chemical signal to another neuron or to the target effector cell.
Synapses are essential to the transmission of nervous impulses from ...
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
6-chloronicotinic acid
Neonicotinoids (sometimes shortened to neonics ) are a class of neuro-active insecticides chemically similar to nicotine, developed by scientists at Shell and Bayer in the 1980s.
The neonicotinoid family includes acetamiprid, clothianidin, dinote ...
, have not been through in-depth toxicological investigations.
Similarly genotoxicity effects remain ambiguous. 6-chloronicotinic acid, according to a research group, is non-
carcinogenic
A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
and is not considered a developmental
toxicant
A toxicant is any toxic substance, whether man-made or naturally occurring. By contrast, a toxin is a poison produced naturally by an organism (e.g. plant, animal, insect). The different types of toxicants can be found in the air, soil, water, or ...
.
Metabolism
The literature on the biotransformation of nitenpyram has been scarce. However, some studies have been conducted.
Toxicokinetic studies have shown that human intestinal caco-2 cell line can absorb
imidacloprid
Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. ...
at a very high rate of efficiency.
The compound completely absorbs (>92%) from the
gastrointestinal tract
The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organ (biology), organs of the digestive syste ...
, 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.
Nitenpyram has been reported to metabolize into 6-chloronicotinic acid.
Nitenpyram in mice metabolizes into nitenpyram-COOH, nitenpyram-deschloropyridine, desmethyl-nitenpyram, nitenpyram-CN, and nitenpyram-deschloropyridine derivatives.
The nitenpyram metabolites have not been through in-depth study. However, these metabolites can under oxidation reactions like the
cyano
Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms.
In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of a ...
group into a
carboxylic
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
group.
6-chloronicotinic acid can make hydrogen bonds with the hydrogen atom of amino groups.
Cytochrome P450
Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...
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. 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. The
precursor
Precursor or Precursors may refer to:
*Precursor (religion), a forerunner, predecessor
** The Precursor, John the Baptist
Science and technology
* Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of unr ...
compound of this reaction is 2-Chloro-5-chloromethylpyridine, which is also used in the preparation of other neonicotinoids like Imidacloprid. The reaction of this compound undergoes three reaction steps.
First step, 2-Chloro-5-chloromethylpyridine reacts with
ethylamine
Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleo ...
on its phase boundary acquiring the molecule N-ethyl-2-chloro-5-pyridylmethyl amine.
![Firstreaction_nitenpyram_synthesis](https://upload.wikimedia.org/wikipedia/commons/3/3c/Firstreaction_nitenpyram_synthesis.png)
Synthesis can then proceed with a
condensation reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
(step 2), adding the solvents
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
and
trichloronitromethane will yield the intermediate N-ethyl-2-chloro-5-pyridylmethyl amine with an additional
nitroethylene group.
![Secondreaction_nitenpyram_synthesis](https://upload.wikimedia.org/wikipedia/commons/c/c5/Secondreaction_nitenpyram_synthesis.png)
In the last step
methylamine
Methylamine is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.
Methylamine is sold as a solution in methanol, ...
is added and reacts with the intermediate, replacing the pharmacophore chloride group, acquiring 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
cis (E) to trans (Z) configuration. 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 ''
trichogramma
''Trichogramma'' is a genus of minute polyphagous wasps that are endoparasitoids of insect eggs. ''Trichogramma'' is one of around 80 genera from the family Trichogrammatidae, with over 200 species worldwide.Consoli FL, Parra JRP, Zucchi RA (2010 ...
''. Nitenpyram specifically was found to have the lowest toxicity, making it useful in IPM (
integrated pest management
Integrated pest management (IPM), also known as integrated pest control (IPC) is a broad-based approach that integrates both chemical and non-chemical practices for economic control of pests. IPM aims to suppress pest populations below the econ ...
) treatment.
In 2015, researchers conducted a study on the toxicity of nitenpyram on the earthworm ''
E.fetida. 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
LC50
In toxicology, the median lethal dose, LD50 (abbreviation for " lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is ...
of nitenpyram on e.fetida was found to be 4.34 mg/kg soil, showing an inhibition of
cellulase
Cellulase (EC 3.2.1.4; systematic name 4-β-D-glucan 4-glucanohydrolase) is any of several enzymes produced chiefly by fungi, bacteria, and protozoans that catalyze cellulolysis, the decomposition of cellulose and of some related polysaccharide ...
activity and damage to the epidermal cells and gut cells. This, however, was significantly less toxic than similar insecticides such as
imidacloprid
Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. ...
,
thiacloprid
Thiacloprid is an insecticide of the neonicotinoid class. Its mechanism of action is similar to other neonicotinoids and involves disruption of the insect's nervous system by stimulating nicotinic acetylcholine receptors. Thiacloprid was develop ...
and
clothianidin
Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has be ...
, 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. 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 ''
Culex quinquefasciatus
''Culex'' is a genus of mosquitoes, several species of which serve as vectors of one or more important diseases of birds, humans, and other animals. The diseases they vector include arbovirus infections such as West Nile virus, Japanese encep ...
'' or the southern house mosquito was tested. The
LC50
In toxicology, the median lethal dose, LD50 (abbreviation for " lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is ...
of the compound was found to be 0.493 ug/ml.
Vertebrates
Aquatic animals
In a study a 60 day chronic toxicity test was conducted on Chinese rare minnows (''
Gobiocypris rarus
''Gobiocypris rarus'' is a freshwater species of cyprinid fish Endemism, endemic to China where it is only found near Jiuxiang in Sichuan province. It is the only species in its genus.
Reproduction
The minimum age of reproduction is 4 months. ...
'') as a general fish model. Of the neonicotinoids tested (imidacloprid, nitenpyram, and
dinotefuran
Dinotefuran is an insecticide of the neonicotinoid class developed by Mitsui Chemicals for control of insect pests such as aphids, whiteflies, thrips, leafhoppers, leafminers, sawflies, mole cricket, white grubs, lacebugs, billbugs, beetles, m ...
), 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
Zebrafish
The zebrafish (''Danio rerio'') is a freshwater fish belonging to the minnow family ( Cyprinidae) of the order Cypriniformes. Native to South Asia, it is a popular aquarium fish, frequently sold under the trade name zebra danio (and thus often ...
. Enzymes inhibiting the formation of
reactive oxygen species
In chemistry, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (). Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen.
The reduction of molecular oxygen () p ...
(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 mg and 1575 mg per kg body weight respectively.
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. 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
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
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
UV light
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
, suggesting that exposure to the sun will also degrade the compound into various degradation products.
Veterinary applications
Nitenpyram tablets, brand name Capstar,
are used to treat flea infestations in cats and dogs.
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
plasma
Plasma or plasm may refer to:
Science
* Plasma (physics), one of the four fundamental states of matter
* Plasma (mineral), a green translucent silica mineral
* Quark–gluon plasma, a state of matter in quantum chromodynamics
Biology
* Blood pla ...
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.
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
efficacy
Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as ''effectiveness'', and it has often been used synonymously, although in pharmacology a pragmatic clinical trial#Efficacy versu ...
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.
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.
In other studies no adverse effects were observed.
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.
Nitenpyram has been used on many commercial crops, such as
cotton
Cotton is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus ''Gossypium'' in the mallow family Malvaceae. The fiber is almost pure cellulose, and can contain minor perce ...
and
corn
Maize ( ; ''Zea mays'' subsp. ''mays'', from es, maíz after tnq, mahiz), also known as corn (North American and Australian English), is a cereal grain first domesticated by indigenous peoples in southern Mexico about 10,000 years ago. Th ...
,
and can be applicated in various ways. Commonly used techniques are
dusting and
seed treatment
In agriculture and horticulture, a seed treatment is any additional material added to the seed. By the amount of material added, it can be divided into:
* A seed dressing, typically containing a "protectant" ( pesticide) applied to the seed and p ...
. 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.
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.
In a study conducted on nine commonly used nicotinoids, nitenpyram was found to have the greatest increase in resistance of the group within
brown planthopper
The brown planthopper (BPH), ''Nilaparvata lugens'' (Stål) (Hemiptera: Delphacidae) is a planthopper species that feeds on rice plants (''Oryza sativa'' L.). These insects are among the most important pests of rice, which is the major staple cro ...
s, a common agricultural pest, between 2011-2012. A substantial increase of resistance was also found in ''
Aphis gossypii
''Aphis gossypii'' is a tiny insect, an aphid ("greenfly") in the superfamily Aphidoidea in the order Hemiptera. It is a true bug and sucks sap from plants. It is a widely distributed pest of a variety of agricultural crops in the families Cucu ...
'' 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
honey bee
A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current co ...
s, wild bees and
butterflies
Butterflies are insects in the macrolepidopteran clade Rhopalocera from the Order (biology), order Lepidoptera, which also includes moths. Adult butterflies have large, often brightly coloured wings, and conspicuous, fluttering flight. The ...
.
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
External links
* {{PPDB, 1612
Dog medications
Cat medications
Pyridines
Nitroethenes
Neonicotinoids