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Wikipedia

Imidacloprid

February 07, 2023

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. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action.[1] Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.[2]

Imidacloprid[1]
Names
IUPAC name
N-{1-[(6-Chloro-3-pyridyl)methyl]-4,5-dihydroimidazol-2-yl}nitramide
Identifiers
  • 138261-41-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:39169 Y
ChEMBL
  • ChEMBL406819 Y
ChemSpider
  • 77934 Y
DrugBank
  • DB07980 Y
ECHA InfoCard 100.102.643
KEGG
  • C11110 Y
  • 86418
UNII
  • 3BN7M937V8 Y
  • DTXSID5032442
  • InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13) Y
    Key: YWTYJOPNNQFBPC-UHFFFAOYSA-N Y
  • InChI=1/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)
    Key: YWTYJOPNNQFBPC-UHFFFAOYAZ
  • [O-][N+](=O)NC/1=N/CCN\1Cc2cnc(Cl)cc2
Properties
C9H10ClN5O2
Molar mass 255.661
Appearance Colorless crystals
Melting point 136.4 to 143.8 °C (277.5 to 290.8 °F; 409.5 to 416.9 K)
0.51 g/L (20 °C)
Pharmacology
QP53AX17 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

From 1999[3] through at least 2018,[4][5] imidacloprid was the most widely used insecticide in the world. Although it is now off patent, the primary manufacturer of this chemical is Bayer CropScience (part of Bayer AG). It is sold under many names for many uses; it can be applied by soil injection, tree injection, application to the skin of the plant, broadcast foliar, ground application as a granular or liquid formulation, or as a pesticide-coated seed treatment.[6][2][7] Imidacloprid is widely used for pest control in agriculture. Other uses include application to foundations to prevent termite damage, pest control for gardens and turf, treatment of domestic pets to control fleas,[2] protection of trees from boring insects,[8] and in preservative treatment of some types of lumber products.[9]

Authorized uses

Imidacloprid is the most widely used insecticide in the world.[3][4][5] Its major uses include:

When used on plants, imidacloprid, which is systemic, is slowly taken up by plant roots and slowly translocated up the plant via xylem tissue.

United States

See also: Neonicotinoid § United States
 
Imidacloprid use in the US to 2019[12]

The estimated annual use of the compound in US agriculture is mapped by the US Geological Service and shows an increasing trend from its introduction in 1994 to 2014 when it reached 2,000,000 pounds (910,000 kg).[12] However, use from 2015 to 2019 dropped following concerns about the effect of neonicotinoid chemicals on pollinating insects.[13] In May 2019, the Environmental Protection Agency revoked approval for a number of products containing imidacloprid as part of a legal settlement, although some formulations continue to be available.[14][15]

Application to trees

When used on trees, it can take 30–60 days to reach the top (depending on the size and height) and enter the leaves in high enough quantities to be effective. Imidacloprid can be found in the trunk, the branches, the twigs, the leaves, the leaflets, and the seeds. Many trees are wind pollinated. But others such as fruit trees, linden, catalpa, and black locust trees are bee and wind pollinated and imidacloprid would likely be found in the flowers in small quantities. Higher doses must be used to control boring insects than other types.[8]

Background

On January 21, 1986, a patent was filed and granted on May 3, 1988, for imidacloprid in the United States (U.S. Pat. No. 4,742,060) by Nihon Tokushu Noyaku Seizo K.K. of Tokyo, Japan.[16]

On March 25, 1992, Miles, Inc. (later Bayer CropScience) applied for registration of imidacloprid for turfgrass and ornamentals in the United States. On March 10, 1994, the U.S. Environmental Protection Agency approved the registration of imidacloprid.[17]

On January 26, 2005, the Federal Register notes the establishment of the '(Pesticide Tolerances for) Emergency Exemptions' for imidacloprid. It use was granted to Hawaii (for the) use (of) this pesticide on bananas(,) and the States of Minnesota, Nebraska, and North Dakota to use (of) this pesticide on sunflower(s).[18]

Biochemistry

Imidacloprid is a systemic insecticide, belonging to the class of chloronicotinyl neonicotinoid insecticides. It works by interfering with the transmission of nerve impulses in insects by binding irreversibly to specific insect nicotinic acetylcholine receptors.[19]

As a systemic pesticide, imidacloprid translocates or moves easily in the xylem of plants from the soil into the leaves, fruit, pollen, and nectar of a plant. Imidacloprid also exhibits excellent translaminar movement in plants and can penetrate the leaf cuticle and move readily into leaf tissue.[20]

Since imidacloprid is efficacious at very low levels (nanogram and picogram), it can be applied at lower concentrations (e.g., 0.05–0.125 lb/acre or 55–140 g/ha) than other insecticides. The availability of imidacloprid and its favorable toxicity package as compared to other insecticides on the market in the 1990s allowed the EPA to replace more toxic insecticides including the acetylcholinesterase inhibitors, the organophosphorus compounds, and methylcarbamates.[21][22]

Environmental fate

The main routes of dissipation of imidacloprid in the environment are aqueous photolysis (half-life = 1–4 hours) and plant uptake. The major photometabolites include imidacloprid desnitro, imidacloprid olefine, imidacloprid urea, and five minor metabolites. The end product of photodegradation is 6-chloronicotinic acid (6-CNA) and ultimately carbon dioxide. Since imidacloprid has a low vapor pressure, it normally does not volatilize readily.[19]

Although imidacloprid breaks down rapidly in water in the presence of light, it remains persistent in water in the absence of light. It has a water solubility of .61 g/L, which is relatively high.[23] In the dark, at pH between 5 and 7, it breaks down very slowly, and at pH 9, the half-life is about 1 year. In soil under aerobic conditions, imidacloprid is persistent with a half-life of the order of 1–3 years. On the soil surface the half-life is 39 days.[24] Major soil metabolites include imidacloprid nitrosimine, imidacloprid desnitro and imidacloprid urea, which ultimately degrade to 6-chloronicotinic acid, CO2, and bound residues.[10][19] 6-Chloronicotinic acid is recently shown to be mineralized via a nicotinic acid (vitamin B3) pathway in a soil bacterium.[25]

In soil, imidacloprid strongly binds to organic matter. When not exposed to light, imidacloprid breaks down slowly in water, and thus has the potential to persist in groundwater for extended periods. However, in a survey of groundwater in areas of the United States which had been treated with imidacloprid for the emerald ash borer, imidacloprid was usually not detected. When detected, it was present at very low levels, mostly at concentrations less than 1 part per billion (ppb) with a maximum of 7 ppb, which are below levels of concern for human health. The detections have generally occurred in areas with porous rocky or sandy soils with little organic matter, where the risk of leaching is high — and/or where the water table was close to the surface.[26]

Based on its high water solubility (0.5-0.6 g/L) and persistence, both the U.S. Environmental Protection Agency and the Pest Management Regulatory Agency in Canada consider imidacloprid to have a high potential to run off into surface water and to leach into ground water and thus warn not to apply it in areas where soils are permeable, particularly where the water table is shallow.[10][19]

According to standards set by the environmental ministry of Canada, if used correctly (at recommended rates, without irrigation, and when heavy rainfall is not predicted), imidacloprid does not characteristically leach into the deeper soil layers despite its high water solubility (Rouchaud et al. 1994; Tomlin 2000; Krohn and Hellpointner 2002).[19] In a series of field trials conducted by Rouchaud et al. (1994, 1996), in which imidacloprid was applied to sugar beet plots, it was consistently demonstrated that no detectable leaching of imidacloprid to the 10–20 cm soil layer occurred. Imidacloprid was applied to a corn field in Minnesota, and no imidacloprid residues were found in sample column segments below the 0–15.2 cm depth segment (Rice et al. 1991, as reviewed in Mulye 1995).[10][19]

However, a 2012 water monitoring study by the state of California, performed by collecting agricultural runoff during the growing seasons of 2010 and 2011, found imidacloprid in 89% of samples, with levels ranging from 0.1 to 3.2 µg/L. 19% of the samples exceeded the EPA threshold for chronic toxicity for aquatic invertebrates of 1.05 µg/L. The authors also point out that Canadian and European guidelines are much lower (0.23 µg/L and 0.067 µg/L, respectively) and were exceeded in 73% and 88% of the samples, respectively. The authors concluded that "imidacloprid commonly moves offsite and contaminates surface waters at concentrations that could harm aquatic invertebrates".[27]

Health effects

The effects of imidacloprid on human health depend on the dose, duration, and frequency of exposure. The effects may also depend on the health of a person and environmental factors. People who might orally ingest acute amounts would experience emesis, diaphoresis, drowsiness and disorientation. This would need to be intentional since a large amount would need to be ingested to experience a toxic reaction.[2]

Toxicology

Based on laboratory rat studies, imidacloprid is rated as "moderately toxic" on an acute oral basis to mammals and low toxicity on a dermal basis by the World Health Organization and the United States Environmental Protection Agency (class II or III, requiring a "Warning" or "Caution" label). It is rated as an "unlikely" carcinogen and as weakly mutagenic by the U.S. EPA (group E). It is not listed for reproductive or developmental toxicity, but is listed on EPA's Tier 1 Screening Order for chemicals to be tested under the Endocrine Disruptor Screening Program (EDSP).[17][28] Tolerances for imidacloprid residues in food range from 0.02 mg/kg in eggs to 3.0 mg/kg in hops.[1]

Mammals

Imidacloprid and its nitrosoimine metabolite (WAK 3839) have been well studied in rats, mice and dogs.

In dogs the LD50 is 450 mg/kg of body weight (i.e., in any sample of medium-sized dogs weighing 13 kilograms (29 lb), half of them would be killed after consuming 5,850 mg of imidacloprid, or about 1⁄5th of an ounce). The acute inhalation LD50 in rats was not reached at the greatest attainable concentrations, 69 milligrams per cubic meter of air as an aerosol, and 5,323 mg a.i./m3 of air as a dust.

In mammals, the primary effects following acute high-dose oral exposure to imidacloprid are mortality, transient cholinergic effects (dizziness, apathy, locomotor effects, labored breathing) and transient growth retardation. Exposure to high doses may be associated with degenerative changes in the testes, thymus, bone marrow and pancreas. Cardiovascular and hematological effects have also been observed at higher doses.

The primary effects of longer term, lower-dose exposure to imidacloprid are on the liver, thyroid, and body weight (reduction). Low- to mid-dose oral exposures have been associated with reproductive toxicity, developmental retardation and neurobehavioral deficits in rats and rabbits. Imidacloprid is neither carcinogenic in laboratory animals nor mutagenic in standard laboratory assays.[29]

It is not irritating to eyes or skin in rabbits and guinea pigs.[1]

Bees

See also: Pesticide toxicity to bees and Colony collapse disorder

Imidacloprid is acutely toxic to honeybees: its LD50 ranges from 5 to 70 nanograms per bee.[30] Honeybee colonies vary in their ability to metabolize toxins, which explains this wide range. Imidacloprid is more toxic to bees than the organophosphate dimethoate (oral LD50 152 ng/bee) or the pyrethroid cypermethrin (oral LD50 160 ng/bee).[30] The toxicity of imidacloprid to bees differs from most insecticides in that it is more toxic orally than by contact. The contact acute LD50 is 0.024 µg active ingredient per bee.[31]

In laboratory studies, sublethal levels of imidacloprid have been shown to impair navigation, foraging behavior, feeding behavior, and olfactory learning performance in honeybees (Apis mellifera).[30][32][33][34][35][36][37][38] In general, however, despite the fact that many laboratory studies have shown the potential for neonicotinoid toxicity, the majority of field studies have found only limited or no effects on honeybees.[39]

In bumblebees, exposure to 10 ppb imidacloprid reduces natural foraging behaviour, increases worker mortality and leads to reduced brood development.[40][41] The probable mechanism is that the mevalonate pathway is substantially downregulated by the chronic imidacloprid exposure, which can help to explain the imidacloprid impairment of the cognitive functions.[42]

Birds

Imidacloprid is considered acutely toxic to birds, and to cause avian reproductive toxicity.[19]

In bobwhite quail (Colinus virginianus), imidacloprid was determined to be moderately toxic with an 14-day LD50 of 152 mg a.i./kg. It was slightly toxic in a 5-day dietary study with an acute oral LC50 of 1,420 mg a.i./kg diet, a NOAEC of < 69 mg a.i./kg diet, and a LOAEC = 69 mg a.i./kg diet. Exposed birds exhibited ataxia, wing drop, opisthotonos, immobility, hyperactivity, fluid-filled crops and intestines, and discolored livers. In a reproductive toxicity study with bobwhite quail, the NOAEC = 120 mg a.i./kg diet and the LOAEC = 240 mg a.i./kg diet. Eggshell thinning and decreased adult weight were observed at 240 mg a.i./kg diet.[17][19]

Imidacloprid is highly toxic to four bird species: Japanese quail, house sparrow, canary, and pigeon. The acute oral LD50 for Japanese quail (Coturnix coturnix) is 31 mg a.i./kg bw with a NOAEL = 3.1 mg a.i./kg. The acute oral LD50 for house sparrow (Passer domesticus) is 41 mg a.i./kg bw with a NOAEL = 3 mg a.i./kg and a NOAEL = 6 mg a.i./kg. The LD50s for pigeon (Columba livia) and canary (Serinus canaria) are 25–50 mg a.i./kg. Mallard ducks are more resistant to the effects of imidacloprid with a 5-day dietary LC50 of > 4,797 ppm. The NOAEC for body weight and feed consumption is 69 mg a.i./kg diet. Reproductive studies with mallard ducks showed eggshell thinning at 240 mg a.i./kg diet.[17][19]

According to the European Food Safety Authority, imidacloprid poses a potential high acute risk for both herbivorous and insectivorous birds.[22] Chronic risk has not been well established.[19]

A 2014 observational study conducted in the Netherlands correlated declines in some bird populations with environmental imidacloprid residues, although it stopped short of concluding that the association was causal.[43]

Aquatic life

Imidacloprid is highly toxic on an acute basis to aquatic invertebrates, with EC50 values = 0.037 - 0.115 ppm. It is also highly toxic to aquatic invertebrates on a chronic basis (effects on growth and movement): NOAEC/LOAEC = 1.8/3.6 ppm in daphnids; NOAEC = 0.001 in Chironomus midge, and NOAEC/LOAEC = 0.00006/0.0013 ppm in mysid shrimp.

Its toxicity to fish is relatively low;[1] however, the EPA has requested review of secondary effects on fish with food chains that include sensitive aquatic invertebrates.[10] Research published in 2018 demonstrated accumulation of imidacloprid in the blood of rainbow trout, contradicting claims from Bayer that persistence (bioaccumulation) does not occur with imidacloprid.[44][45]

Plant life

Imidacloprid has been shown to turn off some genes that some rice varieties use to produce defensive chemicals. While imidacloprid is used for control of the brown planthopper and other rice pests, there is evidence that imidacloprid actually increases the susceptibility of the rice plant to planthopper infestation and attacks.[46] Imidacloprid has been shown to increase the rate of photosynthesis in upland cotton temperatures above 36 degrees Celsius.[47]

Regulation

European Union

See also: Neonicotinoid § European Union

In the mid to late 1990s, French beekeepers reported a significant loss of bees, which they attributed to the use of imidacloprid.[citation needed] In 1999, the French Minister of Agriculture suspended the use of imidacloprid on sunflower seeds and appointed a team of expert scientists to examine the impact of imidacloprid on bees. In 2003, this panel issued a report which concluded that imidacloprid posed a significant risk to bees.[48] In 2004, the French Minister of Agriculture suspended the use of imidacloprid as a seed treatment for sunflowers and maize (corn). Certain imidacloprid seed treatments were also temporarily banned in Italy, following preliminary monitoring studies that identified correlations between bee losses and the use of neonicotinoid pesticides.[49]

In January 2013, a European Food Safety Authority (EFSA) report concluded that neonicotinoids posed an unacceptably high risk to bees: "A high acute risk to honey bees was identified from exposure via dust drift for the seed treatment uses in maize, oilseed rape and cereals. A high acute risk was also identified from exposure via residues in nectar and/or pollen."[22] The EFSA also identified a number of gaps in the scientific evidence and were unable to finalize risk assessments for some uses authorized in the European Union (EU). Following the report, EU member states voted to restrict the use of the three main neonics, including imidacloprid, for seed treatment, soil application (granules) and foliar treatment in crops attractive to bees.[50]

In February 2018, the European Food Safety Authority published a further report concluding that neonicotinoids posed a serious danger to bees.[22] In April 2018, the member states of the EU decided to ban the neonicotinoids for all outdoor uses.[51]

United States

On July 1, 2022, the Commonwealth of Massachusetts in the United States will ban commercial sales of imidacloprid and other neonicotinoids – acetamiprid, clothianidin, dinotefuran, thiacloprid, and thiamethoxam – to the general public for all outdoor uses.[52] Licensed dealers will be able to sell only to pesticide-licensed and certified individuals. The states of Maryland, Connecticut and Vermont also restrict use of neonicotinoid pesticides. [53]

Registrations

Among others, imidacloprid is sold under the brand names: Confidor (Bayer CropScience India),[54] Marathon (OHP, US).[55][56]

See also

References

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External links

 
Wikimedia Commons has media related to Imidacloprid.
  • Gervais, J.A.; Luukinen, B.; Buhl, K.; Stone, D. (2010). "Imidacloprid Technical Fact Sheet". National Pesticide Information Center. Retrieved 23 July 2021.
  • . flora.org. June 21, 2012. Archived from the original on June 21, 2012. Retrieved July 24, 2021.
  • . Expert overview. October 9, 2006. Archived from the original on October 9, 2006. Retrieved July 24, 2021.{{cite web}}: CS1 maint: unfit URL (link)
  • Imidacloprid in the Pesticide Properties DataBase (PPDB)
  • . thetreegeek.com. June 9, 2019. Archived from the original on June 9, 2019. Retrieved July 24, 2021.

February 07, 2023
imidacloprid, systemic, insecticide, belonging, class, chemicals, called, neonicotinoids, which, central, nervous, system, insects, chemical, works, interfering, with, transmission, stimuli, insect, nervous, system, specifically, causes, blockage, nicotinergic. 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 Specifically it causes a blockage of the nicotinergic neuronal pathway By blocking nicotinic acetylcholine receptors imidacloprid prevents acetylcholine from transmitting impulses between nerves resulting in the insect s paralysis and eventual death It is effective on contact and via stomach action 1 Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors this insecticide is more toxic to insects than to mammals 2 Imidacloprid 1 NamesIUPAC name N 1 6 Chloro 3 pyridyl methyl 4 5 dihydroimidazol 2 yl nitramideIdentifiersCAS Number 138261 41 3 Y3D model JSmol Interactive imageChEBI CHEBI 39169 YChEMBL ChEMBL406819 YChemSpider 77934 YDrugBank DB07980 YECHA InfoCard 100 102 643KEGG C11110 YPubChem CID 86418UNII 3BN7M937V8 YCompTox Dashboard EPA DTXSID5032442InChI InChI 1S C9H10ClN5O2 c10 8 2 1 7 5 12 8 6 14 4 3 11 9 14 13 15 16 17 h1 2 5H 3 4 6H2 H 11 13 YKey YWTYJOPNNQFBPC UHFFFAOYSA N YInChI 1 C9H10ClN5O2 c10 8 2 1 7 5 12 8 6 14 4 3 11 9 14 13 15 16 17 h1 2 5H 3 4 6H2 H 11 13 Key YWTYJOPNNQFBPC UHFFFAOYAZSMILES O N O NC 1 N CCN 1Cc2cnc Cl cc2PropertiesChemical formula C9H10ClN5O2Molar mass 255 661Appearance Colorless crystalsMelting point 136 4 to 143 8 C 277 5 to 290 8 F 409 5 to 416 9 K Solubility in water 0 51 g L 20 C PharmacologyATCvet code QP53AX17 WHO Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references From 1999 3 through at least 2018 update 4 5 imidacloprid was the most widely used insecticide in the world Although it is now off patent the primary manufacturer of this chemical is Bayer CropScience part of Bayer AG It is sold under many names for many uses it can be applied by soil injection tree injection application to the skin of the plant broadcast foliar ground application as a granular or liquid formulation or as a pesticide coated seed treatment 6 2 7 Imidacloprid is widely used for pest control in agriculture Other uses include application to foundations to prevent termite damage pest control for gardens and turf treatment of domestic pets to control fleas 2 protection of trees from boring insects 8 and in preservative treatment of some types of lumber products 9 Contents 1 Authorized uses 1 1 United States 2 Application to trees 3 Background 4 Biochemistry 5 Environmental fate 6 Health effects 7 Toxicology 7 1 Mammals 7 2 Bees 7 3 Birds 7 4 Aquatic life 7 5 Plant life 8 Regulation 8 1 European Union 8 2 United States 8 3 Registrations 9 See also 10 References 11 External linksAuthorized uses EditImidacloprid is the most widely used insecticide in the world 3 4 5 Its major uses include Seed treatment Imidacloprid is the most popular seed treatment insecticide in the world 7 Agriculture Control of aphids cane beetles thrips 10 stink bugs locusts and a variety of other insects that damage crops Arboriculture Control of the emerald ash borer hemlock woolly adelgid 11 and other insects that attack trees including hemlock maple oak and birch 8 Home Protection Control of termites 2 10 carpenter ants cockroaches and moisture loving insects Domestic animals Control of fleas applied to the back of neck 2 Turf Control of Japanese beetle larvae exp Grubs Gardening Control of aphids and other pestsWhen used on plants imidacloprid which is systemic is slowly taken up by plant roots and slowly translocated up the plant via xylem tissue United States Edit See also Neonicotinoid United States Imidacloprid use in the US to 2019 12 The estimated annual use of the compound in US agriculture is mapped by the US Geological Service and shows an increasing trend from its introduction in 1994 to 2014 when it reached 2 000 000 pounds 910 000 kg 12 However use from 2015 to 2019 dropped following concerns about the effect of neonicotinoid chemicals on pollinating insects 13 In May 2019 the Environmental Protection Agency revoked approval for a number of products containing imidacloprid as part of a legal settlement although some formulations continue to be available 14 15 Application to trees EditWhen used on trees it can take 30 60 days to reach the top depending on the size and height and enter the leaves in high enough quantities to be effective Imidacloprid can be found in the trunk the branches the twigs the leaves the leaflets and the seeds Many trees are wind pollinated But others such as fruit trees linden catalpa and black locust trees are bee and wind pollinated and imidacloprid would likely be found in the flowers in small quantities Higher doses must be used to control boring insects than other types 8 Background EditOn January 21 1986 a patent was filed and granted on May 3 1988 for imidacloprid in the United States U S Pat No 4 742 060 by Nihon Tokushu Noyaku Seizo K K of Tokyo Japan 16 On March 25 1992 Miles Inc later Bayer CropScience applied for registration of imidacloprid for turfgrass and ornamentals in the United States On March 10 1994 the U S Environmental Protection Agency approved the registration of imidacloprid 17 On January 26 2005 the Federal Register notes the establishment of the Pesticide Tolerances for Emergency Exemptions for imidacloprid It use was granted to Hawaii for the use of this pesticide on bananas and the States of Minnesota Nebraska and North Dakota to use of this pesticide on sunflower s 18 Biochemistry EditImidacloprid is a systemic insecticide belonging to the class of chloronicotinyl neonicotinoid insecticides It works by interfering with the transmission of nerve impulses in insects by binding irreversibly to specific insect nicotinic acetylcholine receptors 19 As a systemic pesticide imidacloprid translocates or moves easily in the xylem of plants from the soil into the leaves fruit pollen and nectar of a plant Imidacloprid also exhibits excellent translaminar movement in plants and can penetrate the leaf cuticle and move readily into leaf tissue 20 Since imidacloprid is efficacious at very low levels nanogram and picogram it can be applied at lower concentrations e g 0 05 0 125 lb acre or 55 140 g ha than other insecticides The availability of imidacloprid and its favorable toxicity package as compared to other insecticides on the market in the 1990s allowed the EPA to replace more toxic insecticides including the acetylcholinesterase inhibitors the organophosphorus compounds and methylcarbamates 21 22 Environmental fate EditThe main routes of dissipation of imidacloprid in the environment are aqueous photolysis half life 1 4 hours and plant uptake The major photometabolites include imidacloprid desnitro imidacloprid olefine imidacloprid urea and five minor metabolites The end product of photodegradation is 6 chloronicotinic acid 6 CNA and ultimately carbon dioxide Since imidacloprid has a low vapor pressure it normally does not volatilize readily 19 Although imidacloprid breaks down rapidly in water in the presence of light it remains persistent in water in the absence of light It has a water solubility of 61 g L which is relatively high 23 In the dark at pH between 5 and 7 it breaks down very slowly and at pH 9 the half life is about 1 year In soil under aerobic conditions imidacloprid is persistent with a half life of the order of 1 3 years On the soil surface the half life is 39 days 24 Major soil metabolites include imidacloprid nitrosimine imidacloprid desnitro and imidacloprid urea which ultimately degrade to 6 chloronicotinic acid CO2 and bound residues 10 19 6 Chloronicotinic acid is recently shown to be mineralized via a nicotinic acid vitamin B3 pathway in a soil bacterium 25 In soil imidacloprid strongly binds to organic matter When not exposed to light imidacloprid breaks down slowly in water and thus has the potential to persist in groundwater for extended periods However in a survey of groundwater in areas of the United States which had been treated with imidacloprid for the emerald ash borer imidacloprid was usually not detected When detected it was present at very low levels mostly at concentrations less than 1 part per billion ppb with a maximum of 7 ppb which are below levels of concern for human health The detections have generally occurred in areas with porous rocky or sandy soils with little organic matter where the risk of leaching is high and or where the water table was close to the surface 26 Based on its high water solubility 0 5 0 6 g L and persistence both the U S Environmental Protection Agency and the Pest Management Regulatory Agency in Canada consider imidacloprid to have a high potential to run off into surface water and to leach into ground water and thus warn not to apply it in areas where soils are permeable particularly where the water table is shallow 10 19 According to standards set by the environmental ministry of Canada if used correctly at recommended rates without irrigation and when heavy rainfall is not predicted imidacloprid does not characteristically leach into the deeper soil layers despite its high water solubility Rouchaud et al 1994 Tomlin 2000 Krohn and Hellpointner 2002 19 In a series of field trials conducted by Rouchaud et al 1994 1996 in which imidacloprid was applied to sugar beet plots it was consistently demonstrated that no detectable leaching of imidacloprid to the 10 20 cm soil layer occurred Imidacloprid was applied to a corn field in Minnesota and no imidacloprid residues were found in sample column segments below the 0 15 2 cm depth segment Rice et al 1991 as reviewed in Mulye 1995 10 19 However a 2012 water monitoring study by the state of California performed by collecting agricultural runoff during the growing seasons of 2010 and 2011 found imidacloprid in 89 of samples with levels ranging from 0 1 to 3 2 µg L 19 of the samples exceeded the EPA threshold for chronic toxicity for aquatic invertebrates of 1 05 µg L The authors also point out that Canadian and European guidelines are much lower 0 23 µg L and 0 067 µg L respectively and were exceeded in 73 and 88 of the samples respectively The authors concluded that imidacloprid commonly moves offsite and contaminates surface waters at concentrations that could harm aquatic invertebrates 27 Health effects EditThe effects of imidacloprid on human health depend on the dose duration and frequency of exposure The effects may also depend on the health of a person and environmental factors People who might orally ingest acute amounts would experience emesis diaphoresis drowsiness and disorientation This would need to be intentional since a large amount would need to be ingested to experience a toxic reaction 2 Toxicology EditBased on laboratory rat studies imidacloprid is rated as moderately toxic on an acute oral basis to mammals and low toxicity on a dermal basis by the World Health Organization and the United States Environmental Protection Agency class II or III requiring a Warning or Caution label It is rated as an unlikely carcinogen and as weakly mutagenic by the U S EPA group E It is not listed for reproductive or developmental toxicity but is listed on EPA s Tier 1 Screening Order for chemicals to be tested under the Endocrine Disruptor Screening Program EDSP 17 28 Tolerances for imidacloprid residues in food range from 0 02 mg kg in eggs to 3 0 mg kg in hops 1 Mammals Edit Imidacloprid and its nitrosoimine metabolite WAK 3839 have been well studied in rats mice and dogs In dogs the LD50 is 450 mg kg of body weight i e in any sample of medium sized dogs weighing 13 kilograms 29 lb half of them would be killed after consuming 5 850 mg of imidacloprid or about 1 5 th of an ounce The acute inhalation LD50 in rats was not reached at the greatest attainable concentrations 69 milligrams per cubic meter of air as an aerosol and 5 323 mg a i m3 of air as a dust In mammals the primary effects following acute high dose oral exposure to imidacloprid are mortality transient cholinergic effects dizziness apathy locomotor effects labored breathing and transient growth retardation Exposure to high doses may be associated with degenerative changes in the testes thymus bone marrow and pancreas Cardiovascular and hematological effects have also been observed at higher doses The primary effects of longer term lower dose exposure to imidacloprid are on the liver thyroid and body weight reduction Low to mid dose oral exposures have been associated with reproductive toxicity developmental retardation and neurobehavioral deficits in rats and rabbits Imidacloprid is neither carcinogenic in laboratory animals nor mutagenic in standard laboratory assays 29 It is not irritating to eyes or skin in rabbits and guinea pigs 1 Bees Edit See also Pesticide toxicity to bees and Colony collapse disorder Imidacloprid is acutely toxic to honeybees its LD50 ranges from 5 to 70 nanograms per bee 30 Honeybee colonies vary in their ability to metabolize toxins which explains this wide range Imidacloprid is more toxic to bees than the organophosphate dimethoate oral LD50 152 ng bee or the pyrethroid cypermethrin oral LD50 160 ng bee 30 The toxicity of imidacloprid to bees differs from most insecticides in that it is more toxic orally than by contact The contact acute LD50 is 0 024 µg active ingredient per bee 31 In laboratory studies sublethal levels of imidacloprid have been shown to impair navigation foraging behavior feeding behavior and olfactory learning performance in honeybees Apis mellifera 30 32 33 34 35 36 37 38 In general however despite the fact that many laboratory studies have shown the potential for neonicotinoid toxicity the majority of field studies have found only limited or no effects on honeybees 39 In bumblebees exposure to 10 ppb imidacloprid reduces natural foraging behaviour increases worker mortality and leads to reduced brood development 40 41 The probable mechanism is that the mevalonate pathway is substantially downregulated by the chronic imidacloprid exposure which can help to explain the imidacloprid impairment of the cognitive functions 42 Birds Edit Imidacloprid is considered acutely toxic to birds and to cause avian reproductive toxicity 19 In bobwhite quail Colinus virginianus imidacloprid was determined to be moderately toxic with an 14 day LD50 of 152 mg a i kg It was slightly toxic in a 5 day dietary study with an acute oral LC50 of 1 420 mg a i kg diet a NOAEC of lt 69 mg a i kg diet and a LOAEC 69 mg a i kg diet Exposed birds exhibited ataxia wing drop opisthotonos immobility hyperactivity fluid filled crops and intestines and discolored livers In a reproductive toxicity study with bobwhite quail the NOAEC 120 mg a i kg diet and the LOAEC 240 mg a i kg diet Eggshell thinning and decreased adult weight were observed at 240 mg a i kg diet 17 19 Imidacloprid is highly toxic to four bird species Japanese quail house sparrow canary and pigeon The acute oral LD50 for Japanese quail Coturnix coturnix is 31 mg a i kg bw with a NOAEL 3 1 mg a i kg The acute oral LD50 for house sparrow Passer domesticus is 41 mg a i kg bw with a NOAEL 3 mg a i kg and a NOAEL 6 mg a i kg The LD50s for pigeon Columba livia and canary Serinus canaria are 25 50 mg a i kg Mallard ducks are more resistant to the effects of imidacloprid with a 5 day dietary LC50 of gt 4 797 ppm The NOAEC for body weight and feed consumption is 69 mg a i kg diet Reproductive studies with mallard ducks showed eggshell thinning at 240 mg a i kg diet 17 19 According to the European Food Safety Authority imidacloprid poses a potential high acute risk for both herbivorous and insectivorous birds 22 Chronic risk has not been well established 19 A 2014 observational study conducted in the Netherlands correlated declines in some bird populations with environmental imidacloprid residues although it stopped short of concluding that the association was causal 43 Aquatic life Edit Imidacloprid is highly toxic on an acute basis to aquatic invertebrates with EC50 values 0 037 0 115 ppm It is also highly toxic to aquatic invertebrates on a chronic basis effects on growth and movement NOAEC LOAEC 1 8 3 6 ppm in daphnids NOAEC 0 001 in Chironomus midge and NOAEC LOAEC 0 00006 0 0013 ppm in mysid shrimp Its toxicity to fish is relatively low 1 however the EPA has requested review of secondary effects on fish with food chains that include sensitive aquatic invertebrates 10 Research published in 2018 demonstrated accumulation of imidacloprid in the blood of rainbow trout contradicting claims from Bayer that persistence bioaccumulation does not occur with imidacloprid 44 45 Plant life Edit Imidacloprid has been shown to turn off some genes that some rice varieties use to produce defensive chemicals While imidacloprid is used for control of the brown planthopper and other rice pests there is evidence that imidacloprid actually increases the susceptibility of the rice plant to planthopper infestation and attacks 46 Imidacloprid has been shown to increase the rate of photosynthesis in upland cotton temperatures above 36 degrees Celsius 47 Regulation EditEuropean Union Edit See also Neonicotinoid European Union In the mid to late 1990s French beekeepers reported a significant loss of bees which they attributed to the use of imidacloprid citation needed In 1999 the French Minister of Agriculture suspended the use of imidacloprid on sunflower seeds and appointed a team of expert scientists to examine the impact of imidacloprid on bees In 2003 this panel issued a report which concluded that imidacloprid posed a significant risk to bees 48 In 2004 the French Minister of Agriculture suspended the use of imidacloprid as a seed treatment for sunflowers and maize corn Certain imidacloprid seed treatments were also temporarily banned in Italy following preliminary monitoring studies that identified correlations between bee losses and the use of neonicotinoid pesticides 49 In January 2013 a European Food Safety Authority EFSA report concluded that neonicotinoids posed an unacceptably high risk to bees A high acute risk to honey bees was identified from exposure via dust drift for the seed treatment uses in maize oilseed rape and cereals A high acute risk was also identified from exposure via residues in nectar and or pollen 22 The EFSA also identified a number of gaps in the scientific evidence and were unable to finalize risk assessments for some uses authorized in the European Union EU Following the report EU member states voted to restrict the use of the three main neonics including imidacloprid for seed treatment soil application granules and foliar treatment in crops attractive to bees 50 In February 2018 the European Food Safety Authority published a further report concluding that neonicotinoids posed a serious danger to bees 22 In April 2018 the member states of the EU decided to ban the neonicotinoids for all outdoor uses 51 United States Edit On July 1 2022 the Commonwealth of Massachusetts in the United States will ban commercial sales of imidacloprid and other neonicotinoids acetamiprid clothianidin dinotefuran thiacloprid and thiamethoxam to the general public for all outdoor uses 52 Licensed dealers will be able to sell only to pesticide licensed and certified individuals The states of Maryland Connecticut and Vermont also restrict use of neonicotinoid pesticides 53 Registrations Edit Among others imidacloprid is sold under the brand names Confidor Bayer CropScience India 54 Marathon OHP US 55 56 See also EditInsecticide Neonicotinoid Pesticide toxicity to beesReferences Edit a b c d e Pesticide Information Profiles Imidacloprid Breaz Extension Toxicology Network Retrieved April 7 2012 a b c d e f Gervais et al 2010 a b Yamamoto Izuru 1999 Nicotine to Nicotinoids 1962 to 1997 In Yamamoto Izuru Casida John eds Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor Tokyo Springer Verlag pp 3 27 a b Casida John E 2018 01 07 Neonicotinoids and Other Insect Nicotinic Receptor Competitive Modulators Progress and Prospects Annual Review of Entomology Annual Reviews 63 1 125 144 doi 10 1146 annurev ento 020117 043042 ISSN 0066 4170 PMID 29324040 a b Ihara Makoto Matsuda Kazuhiko 2018 Neonicotinoids molecular mechanisms of action insights into resistance and impact on pollinators Current Opinion in Insect Science Elsevier 30 86 92 doi 10 1016 j cois 2018 09 009 ISSN 2214 5745 PMID 30553491 S2CID 58767188 Imidacloprid Human Health and Ecological Risk Assessment Final Report PDF USDA Forest Service 2005 Retrieved July 23 2021 a b Bayer seedgrowth Bayer SeedGrowth Archived from the original on January 17 2021 Retrieved April 11 2021 a b c Herms DA McCullough DG Smitley DR Sadof C Williamson RC Nixon PL 2009 Insecticide options for protecting ash trees from emerald ash borer PDF North Central IPM Center Bulletin Archived from the original PDF on January 26 2016 Retrieved April 7 2012 International Code Council Evaluation Service Report ESR 1851 dated August 2011 Archived 2018 12 12 at the Wayback Machine a b c d e f Federoff N E Vaughan Allen Barrett M R 13 November 2008 Environmental Fate and Effects Division Problem Formulation for the Registration Review of Imidacloprid US EPA Retrieved 18 April 2012 Preston Richard 2007 A Death in the Forest The New Yorker a b US Geological Survey 2021 10 12 Estimated Annual Agricultural Pesticide Use for imidacloprid 2019 Retrieved 2022 01 24 EPA Actions to Protect Pollinators US EPA 3 September 2013 Retrieved 24 January 2022 Allington A 21 May 2019 EPA Curbs Use of 12 Bee Harming Pesticides Bloomberg Retrieved 24 January 2022 Bayer April 2021 Neonicotinoid insecticides PDF Retrieved 2022 01 24 U S Pat No 4 742 060 uspto gov a b c d Index for Imidacloprid Pc Code 129099 Pesticides US EPA July 27 2011 Retrieved July 24 2021 Imidacloprid Pesticide Tolerances for Emergency Exemptions Federal Register January 26 2005 Volume 70 Number 16 Page 3634 3642 epa gov a b c d e f g h i j Canadian Council of Ministers of the Environment 2007 Canadian water quality guidelines imidacloprid scientific supporting document PDF Winnipeg Man Canadian Council of Ministers of the Environment ISBN 978 1 896997 71 1 Archived from the original PDF on 2013 03 19 Retrieved February 13 2012 Environmental Fate of Imidacloprid Archived March 16 2012 at the Wayback Machine California Department of Pesticide Regulation 2006 Imidacloprid Risk Characterization Document Dietary and Drinking Water Exposure PDF California Environmental Protection Agency February 9 2006 Retrieved April 7 2012 a b c d Conclusion on the peer review of the pesticide risk assessment for bees for the active substance clothianidin EFSA Journal 11 3066 2013 doi 10 2903 j efsa 2013 3066 Flores Cespedes Francisco Figueredo Flores Cristina Isabel Daza Fernandez Isabel Vidal Pena Fernando Villafranca Sanchez Matilde Fernandez Perez Manuel January 18 2012 Preparation and Characterization of Imidacloprid Lignin Polyethylene Glycol Matrices Coated with Ethylcellulose Journal of Agricultural and Food Chemistry 60 4 1042 1051 doi 10 1021 jf2037483 PMID 22224401 Matthew Fossen 2006 Environmental Fate of Imidacloprid PDF Archived from the original PDF on March 16 2012 Retrieved April 16 2016 Shettigar M Pearce S Pandey R Khan F Dorrian SJ Balotra S Russell RJ Oakeshott JG Pandey G 2012 Cloning of a novel 6 chloronicotinic acid chlorohydrolase from the newly isolated 6 chloronicotinic acid mineralizing Bradyrhizobiaceae strain SG 6C PLOS ONE 7 11 e51162 Bibcode 2012PLoSO 751162S doi 10 1371 journal pone 0051162 PMC 3511419 PMID 23226482 Hahn Jeffrey Herms Daniel A McCullough Deborah G February 2011 Frequently Asked Questions Regarding Potential Side Effects of Systemic Insecticides Used To Control Emerald Ash Borer Archived 2012 08 01 at the Wayback Machine University of Michigan Extension Michigan State University The Ohio State University Extension Starner Keith Goh Kean S 2012 Detections of Imidacloprid in Surface Waters of Three Agricultural Regions of California USA 2010 2011 Bulletin of Environmental Contamination and Toxicology 88 3 316 321 doi 10 1007 s00128 011 0515 5 PMID 22228315 S2CID 18454777 Endocrine Disruptor Screening Program Tier 1 Screening Order Issuing Announcement Federal Register Notice Oct 21 2009 Vol 74 No 202 pp 54422 54428 USDA Forest Service Forest Health Protection December 28 2005 Imidacloprid Human Health and Ecological Risk Assessment Final Report HUMAN HEALTH RISK ASSESSMENT Overview 3 1 United States Forest Service Retrieved July 30 2013 dead link a b c Suchail Severine Guez David Belzunces Luc P November 2001 Discrepancy between acute and chronic toxicity induced by imidacloprid and its metabolites in Apis mellifera Environmental Toxicology and Chemistry 20 11 2482 2486 doi 10 1002 etc 5620201113 PMID 11699773 S2CID 22209995 Suchail Severine Guez David Belzunces Luc P July 2000 Characteristics of imidacloprid toxicity in two Apis mellifera subspecies PDF Environmental Toxicology and Chemistry 19 7 1901 1905 doi 10 1002 etc 5620190726 S2CID 84822758 Armengaud C Lambin M Gauthier M 2002 Effects of imidacloprid on the neural processes of memory in Devillers J Pham Delegue M H eds Honey bees estimating the environmental impact of chemicals New York Taylor amp Francis pp 85 100 ISBN 9780415275187 Decourtye A Lacassie E Pham Delegue M H 2003 Learning performances of honeybees Apis mellifera L are differentially affected by imidacloprid according to the season Pest Manag Sci 59 3 269 278 doi 10 1002 ps 631 PMID 12639043 Decourtye A Armengaud C Devillers R M Cluzeau S 2004 Imidacloprid impairs memory and brain metabolism in the honeybee Apis mellifera L Pesticide Biochem Phys 78 2 83 92 doi 10 1016 j pestbp 2003 10 001 Guez D Suchail S Gauthier M Maleszka R Belzunces L 2001 Contrasting effects of imidacloprid on habituation in 7 and 8 day old honeybees Apis mellifera Neurobiology of Learning and Memory 76 2 183 191 doi 10 1006 nlme 2000 3995 PMID 11502148 S2CID 17822619 Pham Delegue M H Cluzeau S 1999 Effets des produits phytosanitaires sur l abeille incidence du traitement des semences de tournesol par Gaucho sur les disparitions de butineuses Rapport final de synthese au Ministere de l Agriculture et de la Peche Lambin M Armengaud C Ramond S Gauthier M 2001 Imidacloprid induced facilitation of the proboscis extension reflex habituation in the honeybee Archives of Insect Biochemistry and Physiology 48 3 129 134 doi 10 1002 arch 1065 PMID 11673842 Williamson S M Wright G A 2013 Exposure to multiple cholinergic pesticides impairs olfactory learning and memory in honeybees PDF Journal of Experimental Biology 216 10 1799 1807 doi 10 1242 jeb 083931 ISSN 0022 0949 PMC 3641805 PMID 23393272 Neonicotinoids Pollinator Network Cornell Retrieved May 10 2019 Gill R J Ramos Rodriguez O Raine N E 2012 Combined pesticide exposure severely affects individual and colony level traits in bees Nature 491 7422 105 108 Bibcode 2012Natur 491 105G doi 10 1038 nature11585 PMC 3495159 PMID 23086150 Bryden John Gill Richard J Mitton Robert A A Raine Nigel E Jansen Vincent A A 2013 Chronic sublethal stress causes bee colony failure Ecology Letters 16 12 1463 1469 doi 10 1111 ele 12188 PMC 4299506 PMID 24112478 Erban T Sopko B Talacko P Harant K Kadlikova K Halesova T Riddellova K Pekas A 2019 Chronic exposure of bumblebees to neonicotinoid imidacloprid suppresses the entire mevalonate pathway and fatty acid synthesis J Proteomics 196 69 80 doi 10 1016 j jprot 2018 12 022 PMID 30583045 S2CID 58641344 Hallmann CA Foppen RP van Turnhout CA de Kroon H Jongejans E July 2014 Declines in insectivorous birds are associated with high neonicotinoid concentrations Nature 511 7509 341 3 Bibcode 2014Natur 511 341H doi 10 1038 nature13531 PMID 25030173 S2CID 4464169 Frew JA Brown JT Fitzsimmons PN Hoffman AD Sadilek M Grue CE Nichols JW February 2018 Toxicokinetics of the neonicotinoid insecticide imidacloprid in rainbow trout Oncorhynchus mykiss Comp Biochem Physiol C 205 34 42 doi 10 1016 j cbpc 2018 01 002 PMC 5847319 PMID 29378254 Risk benefit analysis of Bayer s imidacloprid greenstarsproject org March 21 2021 Retrieved December 14 2021 Cheng Y Shi ZP Jiang LB Ge LQ Wu JC Jahn GC March 2012 Possible connection between imidacloprid induced changes in rice gene transcription profiles and susceptibility to the brown plant hopper Nilaparvatalugens Stal Hemiptera Delphacidae Pestic Biochem Physiol 102 531 3 213 219 doi 10 1016 j pestbp 2012 01 003 PMC 3334832 PMID 22544984 Gonias Evangelos D Oosterhuis Derrick M Bibi Androniki C 2007 Physiologic Response of Cotton to the Insecticide Imidacloprid under High Temperature Stress Journal of Plant Growth Regulation 27 1 77 82 doi 10 1007 s00344 007 9033 4 ISSN 0721 7595 S2CID 20930112 Comite Scientifique et Technique 18 September 2003 Imidaclopride utilise en enrobage de semences Gaucho et troubles des abeilles Rapport final Imidacloprid used in coating seeds Gaucho and disorders of bees Final report PDF in French Archived from the original PDF on 16 March 2012 Retrieved 18 April 2012 Colony Collapse Disorder European Bans on Neonicotinoid Pesticides Pesticides US EPA epa gov June 23 2010 Archived from the original on September 4 2011 Retrieved July 24 2021 McDonald Gibson Charlotte 29 April 2013 Victory for bees as European Union bans neonicotinoid pesticides blamed for destroying bee population The Independent Archived from the original on 1 May 2013 Retrieved 1 May 2013 EU to fully ban neonicotinoid insecticides to protect bees Reuters 27 April 2018 Retrieved 29 April 2018 FREQUENTLY ASKED QUESTIONS Pesticides Containing Neonicotinoids Registration Change Massachusetts regulators to restrict consumer use of bee toxic neonicotinoid pesticides Insecticide Confidor Bayer CropScience India Retrieved 2021 04 11 US EPA United States Environmental Protection Agency 2015 04 21 Label Amendment minor label revisions Product Name Marathon 1 Granular Greenhouse and Nursery Insecticide EPA Registration Number 59807 15 Application Date March 17 2015 Decision Number 502678 PDF Archived from the original PDF on 2021 04 11 OHP MARATHON 1 Granular PDF Archived from the original PDF on 2018 05 16 External links Edit Wikimedia Commons has media related to Imidacloprid Gervais J A Luukinen B Buhl K Stone D 2010 Imidacloprid Technical Fact Sheet National Pesticide Information Center Retrieved 23 July 2021 CHO Fact Sheet on the grub killing pesticide Merit Insecticide containing Imidacloprid flora org June 21 2012 Archived from the original on June 21 2012 Retrieved July 24 2021 Imidacloprid Bayer Expert overview October 9 2006 Archived from the original on October 9 2006 Retrieved July 24 2021 a href Template Cite web html title Template Cite web cite web a CS1 maint unfit URL link Imidacloprid in the Pesticide Properties DataBase PPDB Optrol thetreegeek com June 9 2019 Archived from the original on June 9 2019 Retrieved July 24 2021 Portals Chemistry Insects Retrieved from https en wikipedia org w index php title Imidacloprid amp oldid 1134611391, wikipedia, wiki, book, books, library,

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