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| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 200px
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| ImageName = Partially condensed, Kekulé, skeletal formula of a minor clothiandin (E) tautomer
| Imagename=Partially condensed, Kekulé, skeletal formula of a minor clothiandin (E) tautomer
| IUPACName = 1-(2-Chlor-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine<ref>{{PubChem|213027}}</ref>
| IUPACname=1-%282-Chlor-1%2C3-thiazol-5-ylmethyl%29-3-methyl-2-nitroguanidine%26lt%3Bref>{{PubChem|213027}}</ref>
| Section1 = {{Chembox Identifiers
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| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|changed|??}}
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| KEGG = C18508
| KEGG = C18508
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Clothianidin
| MeSHname=Clothianidin
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 39178
| ChEBI = 39178
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'''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 been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the [[central nervous system]] of insects as an agonist of [[acetylcholine]], the neurotransmitter that stimulates [[nAChR]], targeting the same receptor site ([[AChR]]) and activating post-synaptic acetylcholine receptors but not inhibiting [[AChE]]. The advantage of clothianidin and other neonicotinoids over nicotine is that they are less likely to break down in the environment.
'''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 been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the [[central nervous system]] of insects as an agonist of [[acetylcholine]], the neurotransmitter that stimulates [[nAChR]], targeting the same receptor site ([[AChR]]) and activating post-synaptic acetylcholine receptors but not inhibiting [[AChE]]. The advantage of clothianidin and other neonicotinoids over nicotine is that they are less likely to break down in the environment.


Some authorities have linked the neonicotinoids, including clothianidin, to an unexplained phenomenon termed [[colony collapse disorder]] which has caused a dramatic decline in [[honeybee]]s in recent years.<ref name="beetox" /><ref name="BAKR12DBPO" /> Clothianidin’s major risk concern is to honeybees because it is highly toxic on both a contact and an oral basis. An incident in Germany illustrated the toxicity of clothianidin to honeybees when it was allowed to drift off-site from treated seed during planting.<ref>DeCant, J. and Barrett, M. (November 2, 2010) [http://www.panna.org/sites/default/files/Memo_Nov2010_Clothianidin.pdf "Memorandum re: Clothianidin Registration of Prosper T400 Seed Treatment on Mustard Seed (Oilseed and Condiment) and Poncho/Votivo Seed Treatment on Cotton"] ''[[United States Environmental Protection Agency]]''<ref> Interaction between neonicotinoids and the parasite ''[[Nosema ceranae]]'' significantly weaken and threaten bees.<ref>Alaux, C. ''et al.'' (2010) [http://panna.org/sites/default/files/Alaux_Neonics+Nosema.pdf "Interactions between ''Nosema'' microspores and a neonicotinoid weaken honeybees (Apis mellifera)"] ''Environmental Microbiology'' '''12'''(3):774–82</ref>
Some authorities have linked the neonicotinoids, including clothianidin, to an unexplained phenomenon termed [[colony collapse disorder]] which has caused a dramatic decline in honey bees in recent years.
<ref name=BAKR12DBPO /><ref name=beetox />


== Authorized uses ==
== Authorized uses ==

Revision as of 17:23, 18 February 2012

Clothianidin
Identifiers
3D model (JSmol)
9196326, 8620724 (E)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.103.171 Edit this at Wikidata
KEGG
  • InChI=1S/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11) checkY
    Key: PGOOBECODWQEAB-UHFFFAOYSA-N checkY
  • InChI=1/C6H8ClN5O2S/c1-8-6(11-12(13)14)10-3-4-2-9-5(7)15-4/h2H,3H2,1H3,(H2,8,10,11)
    Key: PGOOBECODWQEAB-UHFFFAOYAT
  • CNC(Nn(:o):o)=NCc1cnc(Cl)s1
  • CNC(N[N+]([O-])=O)=NCC1=CN=C(Cl)S1
Properties
C6H8ClN5O2S
Molar mass 249.67 g·mol−1
Appearance Colorless crystals
Density 1.61 g cm-3
Melting point 179 °C (354 °F; 452 K)
327 mg dm-3 (at 20 °C)
log P 0.732
Acidity (pKa) 7.472
Basicity (pKb) 6.525
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of acetylcholine, the neurotransmitter that stimulates nAChR, targeting the same receptor site (AChR) and activating post-synaptic acetylcholine receptors but not inhibiting AChE. The advantage of clothianidin and other neonicotinoids over nicotine is that they are less likely to break down in the environment.

Some authorities have linked the neonicotinoids, including clothianidin, to an unexplained phenomenon termed colony collapse disorder which has caused a dramatic decline in honeybees in recent years.[1][2] Clothianidin’s major risk concern is to honeybees because it is highly toxic on both a contact and an oral basis. An incident in Germany illustrated the toxicity of clothianidin to honeybees when it was allowed to drift off-site from treated seed during planting.Cite error: A <ref> tag is missing the closing </ref> (see the help page).

Authorized uses

Clothianidin is authorized for spray, dust, soil drench (for uptake via plant roots), injectable liquid (into tree limbs and trunks, sugar cane stalks etc.), and seed treatment uses, in which clothianidin coats seeds that take up the pesticide via the roots as the plant grows. The chemical may be used to protect plants against a wide variety of agricultural pests in many countries, of which the following are mentioned in citable English-language sources: Australia, Austria, Belgium, Bulgaria, Canada, Czech Republic, Denmark, Estonia, France, Finland, Germany, Greece, Hungary, Italy, Ireland, Japan, Korea, Lithuania, Netherlands, New Zealand, Poland, Portugal, Serbia, Slovakia, Slovenia, Spain, UK, and the United States. Seed treatment uses of clothianidin, corn in particular, have been revoked or suspended in Germany, Italy and Slovenia. The suspensions are reflective of E.U. pesticide law and are generally associated with acute poisoning of bees from pesticide dust being blown off of treated seeds, especially corn, and onto nearby farms where bees were performing pollinator services.[3][4][5][6][7][8][9]

Background

Although nicotine has been used as a pesticide for over 200 years it degraded too rapidly in the environment and lacked the selectivity to be very useful in large-scale agricultural situations. However, in order to address this problem, the neonicotinoids (chloronicotinyl insecticides) were developed as a substitute of nicotine. Clothianidin is an alternative to organophosphate, carbamate, and pyrethroid pesticides. It poses lower risks to mammals, including humans, when compared to organophosphates and carbamates. It also plays a key role helping to prevent the build up in insect pests of resistance to organophosphate and pyrethroid pesticides, which is a growing problem in parts of Europe.[10][3][11]

Toxicity

Regulatory authorities describe the toxicological database for clothianidin as “extensive,” and many studies have been reviewed to support registrations around the globe for this chemical. Laboratory and field testing revealed that clothianidin shows relatively low toxicity to many test species but is highly or very highly toxic to others. Because it is systemic, persistent and highly toxic to honey bees, the Pest Management Regulatory Agency of Canada has requested additional data to fully assess the potential effects of chronic exposure of clothianidin, resulting from its potential movement into plant pollen and nectar. Toxicity varies depending on whether the exposure occurs on a short-term (acute) or long-term (chronic) basis.[3][12][13][14][15]

Mammals

Clothianidin is moderately toxic in the short-term to mammals that eat it, and long-term ingestion may result in reproductive and/or developmental effects.[10][3][6] Using laboratory test animals as surrogates for humans and dosages much higher than are expected from exposure related to actual use, rats showed low short-term oral, dermal, and inhalation toxicity to clothianidin. For mice, acute oral toxicity was moderate to high. Rabbits showed little to no skin or eye irritation when exposed to clothianidin, and the skin of guinea pigs was not sensitized by it. When extrapolated to humans, these results suggest that clothianidin is moderately toxic through oral exposure, but toxicity is low through skin contact or inhalation. While clothianidin may cause slight eye irritation, it is not expected to be a skin sensitizer or irritant. Clothianidin does not damage genetic material nor is there evidence that it causes cancer in rats or mice; it is unlikely to be a human carcinogen.[10][3][12]

Permissible amounts of clothianidin residue on food and animal feed vary from crop to crop and nation to nation. However, regulatory authorities around the globe emphasize that when used according to the label instructions, clothianidin residues on food are not expected to exceed safe levels (as defined by each nation’s laws and regulations).[16][17][12][18][19][20]

Aquatic life

The United States EPA states that clothianidin should not present a direct acute or chronic risk to freshwater and estuarine/marine fish, or a risk to terrestrial or aquatic vascular and nonvascular plants. It is considered to be toxic to aquatic invertebrates if disposal of wastes according to disposal instructions are not followed. The Pest Management Regulatory Agency of Canada lists it as "very highly toxic" to aquatic invertebrates, but only slightly toxic to fish.

Birds

According to the EPA, clothianidin is practically non-toxic to test bird species that were fed relatively large doses of the chemical on an acute basis. However, EPA assessments show that exposure to treated seeds through ingestion may result in chronic toxic risk to non-endangered and endangered small birds (e.g., songbirds). Bobwhite quail eggshell thickness was affected when the test birds were given a diet consisting of relatively large amounts of clothianidin-treated seeds. [10][3][6] The Pest Management Regulatory Agency of Canada lists clothianidin as "moderately toxic" to birds.

Bees and other insect pollinators

Honeybees pollinate crops responsible for about a third of the human diet; about $15 billion worth of U.S. crops. Beginning in 2006, beekeepers began to report unexplained losses of hives — 30 percent and upward — leading to a phenomenon called colony collapse disorder (CCD). The cause of CCD remains under debate, but most scientists believe that the decline is linked to mites, parasites and viruses, loss of habitat and food, and an onslaught of pesticides.[2] Neonicotinoid insecticides have been implicated by beekeepers due to a progressive disease in hive populations resulting in a complete loss of the colonies.[1]

Honeybees and other pollinators are particularly sensitive to clothianidin, as evidenced by the results of laboratory and field toxicity testing and demonstrated in acute poisoning incidents in France and Germany in 2008, and in Canada in 2010 associated with the planting of corn seeds treated with clothianidin.[21][22][23][24] To reduce the risk to pollinators from acute exposure to clothianidin sprays and dust, including dust that results from planting treated seeds, label instructions prohibit the use of these products when crops or weeds are in bloom and pollinators are nearby. The use of sticking agents to reduce dust from treated seeds are also required or are standard practice in many countries, and Germany has stipulated that certain older, air-driven seeding equipment may not be used in corn seed planting operations.[25][26]

The Australian Pesticides and Veterinary Medicines Authority notes that clothianidin ranks “among the most highly acutely toxic insecticides to bees” through contact and oral exposure.[27] A large number of published studies have shown that low levels of imidacloprid, a neonicotinoid pesticide chemically similar to clothianidin, produces sublethal and behavioral effects in bees, including disorientation and effects on foraging, learning performance, motor coordination, and food consumption.[28][29][30][31][32][33][34][35] Since clothianidin is a systemic pesticide that is taken up by the plant, there is also potential for long-term effects to bees and other pollinators from clothianidin residue in pollen and nectar. In addition to potential effects on worker bees, there are also concerns about lethal and/or sub-lethal effects in the larvae and reproductive effects in the queen from long-term exposure. However, the available data does not show conclusively that these potential long-term effects actually happen when clothianidin products are used at authorized rates.[36][37]

In a July 2008 German beekill incident, German beekeepers reported that 50 to 100 percent of their hives had been lost after pneumatic equipment used to plant corn seed blew clouds of pesticide dust into the air, which was then pushed by the wind onto neighboring canola fields in which managed bees were performing pollinator services. The accident was found to be the result of improper planting procedures and the weather, however, in 2009, Germany suspended authorization for the use of clothianidin on corn, citing unanswered questions that remained about potential exposure of bees and other pollinators to neonicotinoid pesticides.[26]

A two-year pier reviewed study done by Purdue University scientists found that an analyses of bees found dead in and around hives from several apiaries in Indiana showed the presence of the neonicotinoid insecticides clothianidin and thiamethoxam. The research showed that the insecticides were present at high concentrations in waste talc that is exhausted from farm machinery during planting. Talc is used in vacuum system planters to keep pesticide treated seeds flowing freely and excess talc is released during routine planting and planter cleaning prcedures. The insecticides were also consistently found at low levels in soil up to two years after treated seed was planted, and on nearby dandelion flowers and corn pollen gathered by the bees.[38][39]

Data gaps

North American and European pesticide regulatory authorities have identified specific data gaps and uncertainties for which clothianidin manufacturers must provide data.[10][40][41] Studies required of the manufacturers will further investigate clothianidin’s:

  • environmental persistence in soil and subsequent uptake in rotational crops
  • availability in pollen and nectar
  • long-term effects on honey bees and other pollinators
  • developmental immunotoxicity
  • effects on aerobic aquatic metabolism
  • ability to leach from treated seeds and
  • acute toxicity to freshwater invertebrates

The challenges associated with studying potential long-term effects of pesticides on honey bee colonies is well documented and includes the inability to adequately monitor individual bee health or extrapolate effects on individuals to whole hives. Behavior changes between bees and/or colonies in laboratory or field test conditions versus natural environments also add to the challenges.[42] Studies submitted by Bayer AG to USEPA have provided some useful information about clothianidin's potential long-term effects on honey bees but outstanding questions remain. USEPA's analysis of nine pollinator field studies submitted concluded that three were invalid, so EPA did not use the data they provided in making its regulatory decision for clothianidin. EPA classified the remainder as supplemental, generally because Bayer AG conducted the studies without EPA first approving the protocols.[43][44][45][46][47][48][49][50] Supplemental studies are ones that don't definitively answer uncertainties but still provide some data that might be useful in characterizing risk.[51] Indicative of the rapid advance of regulators' understanding of pollinator science, USEPA first accepted one of the studies as sound science in 2007, then reclassified it as invalid in November 2010 only to reclassify it as supplemental one month later.[52] The changes in EPA's classification of this study have no effect on the regulatory status for clothianidin in the U.S. because the study does not provide data with which EPA can legally justify altering its 2003 registration decision.[53] An international group of pesticide regulators, researchers, industry representatives, and beekeepers is working to develop a study protocol that will definitively answer remaining questions about the potential long-term effects on bee colonies and other pollinators.[54]

Environmental persistence

Laboratory and field testing shows that clothianidin is persistent and mobile in the environment, stable to hydrolysis, and has potential to leach to ground water and be transported via runoff to surface water bodies. Worst-case scenario estimates indicate that if applied at the maximum rate repeatedly over years, clothianidin has the potential to accumulate in the top 15 cm of soil. However, the Australian pesticide authority’s review of rotational crop studies determined that clothianidin generally is not taken up by crops sown in fields where treated corn seeds were planted, even when the test corn seeds were coated with an intentionally large amount of the chemical (2 mg/seed vs the authorized maximum application rate of 1.25 mg).[10][3]

Risk mitigation

Once laboratory and field data identify hazards associated with a chemical, regulatory authorities take different approaches to mitigate those hazards and bring the risks down to acceptable levels, as defined by each nation’s laws and regulations. For clothianidin, hazard mitigation includes establishing the maximum amount of the chemical that can be used (e.g. kg/acre or mg/seed), requiring buffer zones around treated fields to protect water supplies, and prohibiting the use of low-technology seed treatment methods or equipment that can send clouds of clothianidin dust or spray up into the air during seeding operations.[10][3][12][55]

Clothianidin users are also required to monitor the weather and not use the chemical or seeds treated with it on windy days or when rain is forecast. Workers are protected from clothianidin exposure through requirements for personal protective gear, such as long-sleeve shirts, gloves, long pants, boots, and face mask or respirators as appropriate. To reduce the possibility that birds and small mammals might eat treated seeds, users are required to ensure that soil covers planted seeds and that any spilled seed is picked up.

See also

References

  1. ^ a b Decourtye and Devillers (2010) "Ecotoxicity of Neonicotinoid Insecticides to Bees" in Insect Nicotinic Acetylcholine Receptors ed. by Steeve Hervé Thany (New York: Springer/Landes) Chapter 8, pp. 85-95, on p. 86
  2. ^ a b Kay, J. (August 19, 2008) "Lawsuit seeks EPA pesticide data" San Francisco Chronicle
  3. ^ a b c d e f g h "Australian evaluation of the new active CLOTHIANIDIN" (PDF). Australian Pesticides and Veterinary Medicines Authority. Retrieved 15 August 2011.
  4. ^ "Pesticides 2011" (PDF). Ireland's Pesticide Registration & Control Division Department of Agriculture, Fisheries and Food. Retrieved 12 August 2011.
  5. ^ "Clothianidin Status web page". USEPA. Retrieved 12 August 2011.
  6. ^ a b c "Clothianidin registration announcement" (PDF). Australian Pesticides and Veterinary Medicines Authority. Retrieved 12 August 2011.
  7. ^ "Regulatory Note: Clothianidin, Poncho 600 and Seed Treatment Insecticide". Health Canada, Pest Management Regulatory Agency. Retrieved 12 August 2011.
  8. ^ "MODE OF ACTION CLASSIFICATION TABLE FOR UK APPROVED INSECTICIDE ACTIVE SUBSTANCES" (PDF). Insecticide Resistance Action Group, U.K. Retrieved 16 August 2011.
  9. ^ "Background Information On Use Of Neonicotinoid Pesticides And Their Effects On Bees, see Action in other Member States". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
  10. ^ a b c d e f g "USEPA Clothianidin fact sheet" (PDF). U.S. Environmental Protection Agency. Retrieved 12 August 2011.
  11. ^ "Background Information On Use Of Neonicotinoid Pesticides And Their Effects On Bees". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
  12. ^ a b c d "Evaluation Report ERC2011-01, Clutch 50 WDG, Arena 50 WDG and Clothianidin Insecticides". Health Canada, Pest Management Regulatory Agency. Retrieved 15 August 2011.
  13. ^ "ADVICE SUMMARY, APPLICATION FOR REGISTRATION OF A CHEMICAL PRODUCT" (PDF). Australian Pesticides and Veterinary Medicines Authority. Retrieved 15 August 2011.
  14. ^ "USEPA Freedom of Information Act e-Reading Room for Clothianidin". USEPA. Retrieved 15 August 2011.
  15. ^ "ADVICE SUMMARY, APPLICATION FOR VARIATION OF A REGISTERED CHEMICAL PRODUCT". Australian Pesticides and Veterinary Medicines Authority. Retrieved 15 August 2011.
  16. ^ "Proposed Maximum Residue Limit PMRL2011-30, Clothianidin". Health Canada, Pest Management Regulatory Agency. Retrieved 12 August 2011.
  17. ^ "ADVICE SUMMARY, APPLICATION FOR VARIATION OF A REGISTERED CHEMICAL PRODUCT" (PDF). Australian Pesticides and Veterinary Medicines Authority. Retrieved 15 August 2011.
  18. ^ "U.S. Federal Register Notice: Clothianidin; Pesticide Tolerances". USEPA. Retrieved 15 August 2011.
  19. ^ "Keeping our Food Safe: Measuring, Monitoring and Assessing Residues". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
  20. ^ "Official Journal of the European Union, amending Annexes II and III to Regulation (EC) No 396/2005 of the European Parliament and of the Council as regards maximum residue levels for chlorothalonil clothianidin, difenoconazole, fenhexamid, flubendiamide, nicotine, spirotetramat, thiacloprid and thiamethoxam in or on certain products" (PDF). U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
  21. ^ "Weakening, collapse and mortality of bee colonies, p.88" (PDF). French Food Safety Agency. Retrieved 15 August 2011.
  22. ^ "Evaluation of Pesticide Incident Report 2010-3100". Health Canada, Pest Management Regulatory Agency. Retrieved 15 August 2011.
  23. ^ "Evaluation of Pesticide Incident Report 2010-3391". Health Canada, Pest Management Regulatory Agency. Retrieved 15 August 2011.
  24. ^ "Evaluation of Pesticide Incident Report 2010-4374". Health Canada, Pest Management Regulatory Agency. Retrieved 15 August 2011.
  25. ^ "Pesticide News Story: EPA Acts to Protect Bees". USEPA. Retrieved 15 August 2011.
  26. ^ a b "BVL 2.9.2009 Press Release". Federal Office of Consumer Protection and Food Safety. Retrieved 15 July 2011.
  27. ^ "Australian evaluation of the new active CLOTHIANIDIN, p35" (PDF). Australian Pesticides and Veterinary Medicines Authority. Retrieved 15 August 2011.
  28. ^ Yang, E.C., Chuang, Y.C., Chen, Y.L., and Chang, L.H. 2008. Abnormal foraging behavior induced by sublethal dosage of imidacloprid in the honeybee (Hymenoptera: Apidae). J. Econ Entomology 101(6):1743-1748
  29. ^ Medrzycki P., Montanari, R., Bortolotti, L., Sabatini, A. G., Maini, S., and Porrini, C. 2003. Effects of imidacloprid administered in sub-lethal doses on honey bee behaviour. Laboratory tests. Bulletin of Insectology 56 (1): 59-62
  30. ^ Desneux, N., Decourtye, A., and Delpuech, J-M. 2007. The sublethal effects of pesticides on beneficial arthropods. Annual Review of Entomology 52: 81–106
  31. ^ Armengaud, C., Lambin, M., and Gauthier, M. 2002. Effects of imidacloprid on the neural processes of memory. In J. Devillers and M.H. Pham-Delegue(eds). Honey bees: estimating the environmental impact of chemicals (pp. 85-100). New York: Taylor & Francis
  32. ^ Bonmatin, J.M., Moineau, I., Charvet, R., Collin, M.E., Fleche, C., and Bengsch, E.R. 2005. Behavior of Imidacloprid in Fields. In E.Lcihtfourse, J. Schwarzbauer, and D. Robert (eds). Toxicity for Honey Bees in Environmental Chemistry: Green Chemistry and Pollutants in Ecosytems. New York: Springer
  33. ^ Aliouane, Y., Kacimi El Hassani, A., Gary, V., Armengaud, C., Lambin, M., Gauthier, M. (2009) Subchronic exposure of honeybees to sublethal doses of pesticides: effect on behavior. Environ Toxicol Chem 28:113–122
  34. ^ Bortolotti, L., Montanari, R., Marcelino, J., Medrzycki, P., Maini, S., and Porrini, C. 2003. Effects of sub-lethal imidacloprid doses on the homing rate and foraging activity of honey bees. Bulletin of Insectology 56(1): 63-67
  35. ^ Decourtye, A., Lacassie, E., Pham-Delegue, MH. (2003) Learning performances of honeybees (Apis mellifera L) are differentially affected by imidacloprid according to the season. Pest Manage Sci 59:269–278
  36. ^ "Clothianidin Status web page, Risk Assessment and Risk Mitigation section". USEPA. Retrieved 15 August 2011.
  37. ^ "Weakening, collapse and mortality of bee colonies, last bullet on p.49" (PDF). French Food Safety Agency. Retrieved 15 August 2011.
  38. ^ http://www.purdue.edu/newsroom/research/2012/120111KrupkeBees.html
  39. ^ http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0029268
  40. ^ "Evaluation Report ERC2011-01, under What Additional Scientific Information Is Being Requested?". Health Canada, Pest Management Regulatory Agency. Retrieved 15 August 2011.
  41. ^ "Re-registration Requirements Following Further Annex I Inclusion Decisions, see Other updates section". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
  42. ^ "Weakening, collapse and mortality of bee colonies, pp.143-144" (PDF). French Food Safety Agency. Retrieved 15 August 2011.
  43. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422440" (PDF). USEPA. Retrieved 15 August 2011.
  44. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422439" (PDF). USEPA. Retrieved 15 August 2011.
  45. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422431" (PDF). USEPA. Retrieved 15 August 2011.
  46. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422436" (PDF). USEPA. Retrieved 15 August 2011.
  47. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422437" (PDF). USEPA. Retrieved 15 August 2011.
  48. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422435" (PDF). USEPA. Retrieved 15 August 2011.
  49. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422438" (PDF). USEPA. Retrieved 15 August 2011.
  50. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 45422434" (PDF). USEPA. Retrieved 15 August 2011.
  51. ^ "Reclassification of MRID 46907801 Data Package for Clothianidin" (PDF). USEPA. Retrieved 15 August 2011.
  52. ^ "DATA EVALUATION RECORD, HONEY BEE - FIELD TESTING FOR POLLINATORS MRID 46907801/46907802" (PDF). USEPA. Retrieved 15 August 2011.
  53. ^ "Clothinidin Status: 2010 Reclassification of Clothianidin Field Study for Pollinators". USEPA. Retrieved 15 August 2011.
  54. ^ "January 24, 2011 International SETAC Pellston Workshop". The Society of Environmental Toxicology and Chemistry (SETAC). Retrieved 15 August 2011.
  55. ^ "Notice of Approval Number: 0065 of 2011, APPROVAL AND CONSENT FOR A PLANT PROTECTION PRODUCT". U.K. Chemicals Regulation Directorate of the Health and Safety Executive. Retrieved 16 August 2011.
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