Imidacloprid[1]
IUPAC name	N-[1-[(6-Chloro-3-pyridyl)methyl]-4,5-dihydroimidazol-2-yl]nitramide
Identifiers
CAS number	[13826-41-3]
PubChem	86418
SMILES	C1CN(C(=N1)N[N+](=O)[O-])CC2=CN=C(C=C2)Cl
Properties
Molecular formula	C9H10ClN5O2
Molar mass	255. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 661
Appearance	Colorless crystals
Melting point	136. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 4-143. 8 °C
Solubility in water	0. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 51 g/L (20 °C)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Imidacloprid is an insecticide manufactured by Bayer Cropscience (part of Bayer AG). In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An insecticide is a Pesticide used against Insects in all developmental forms For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German It is sold under a variety of trade names including Kohinor, Admire, Advantage, Gaucho, Merit, Confidor, Hachikusan, Premise, Prothor, and Winner. A trade name, also known as a trading name or a business name, is the name which a Business trades under for commercial purposes although its registered

Imidacloprid was first patented in the United States in U. S. Pat. No. 4,742,060, on May 3, 1988, by Nihon Tokushu Noyaku Seizo K. Events 1491 - Kongo monarch Nkuwu Nzinga is baptised by Portuguese missionaries adopting the baptismal name of João Year 1988 ( MCMLXXXVIII) was a Leap year starting on Friday (link displays 1988 Gregorian calendar) K. of Tokyo, Japan.

In France, its use (as Gaucho) has become controversial in terms of a possible link to derangement of behavior in domesticated honeybees. This article is about the country For a topic outline on this subject see List of basic France topics. This article refers collectively to all true honey bees for the "common" domesticated honey bee see European honey bee Honey bees See Imidacloprid effects on bee population. Imidacloprid is a systemic Insecticide produced by the chemical firm Bayer AG.

Contents 1 Biochemistry 2 Uses 3 Proper use of Advantage 4 A systemic insecticide 5 See also 6 References 7 Sources 8 External links

Biochemistry

A chlorinated analog of nicotine, the compound therefore belongs to the class of chloronicotinyl insecticides, and acts on the nicotinic acetylcholine receptor; the chlorination inhibits degradation by acetylcholine-esterase. Nicotine is an Alkaloid found in the Nightshade family of plants ( Solanaceae) which constitutes approximately 0 Structure Nicotinic receptors with a molecular mass of 290 kDa, are made up of five subunits arranged symmetrically around the central pore. In Biochemistry, cholinesterase is an enzyme that catalyzes the Hydrolysis of the Neurotransmitter Acetylcholine into Imidacloprid is notable for its relatively low toxicity to most animals other than insects due to its specificity for this type of receptor, which is found more often in insect nervous systems and zooplankton than that of other animals (exceptions exist; earthworms and a few species of fish, for example). Toxicity is the degree to which a substance is able to damage an exposed organism Insects ( Class Insecta) are a major group of Arthropods and the most diverse group of Animals on the Earth with over a million described In Biochemistry, a receptor is a Protein molecule embedded in either the Plasma membrane or Cytoplasm of a cell to which a mobile signaling The nervous system is a Network of specialized cells that communicate information about an animal's surroundings and itself Zooplankton are the Heterotrophic (sometimes detritivorous) type of Plankton. Earthworm is the usual name for the largest members of Oligochaeta (which is either a class or subclass depending on the author in the phylum Annelida In classical Fish are aquatic Vertebrate animals that are typically ectothermic (previously Cold-blooded) covered with scales, and equipped with two This potentially allows for lower concentrations (e. g. 0. 05–0. 125 lb/acre or 55–140 g/ha) to be used for insect control than other neurotoxins (particularly organophosphates) and enabling its use in applications as diverse as flea treatments for pets, control of beetle larvae in lawns, eradication or prevention of termite infestation in buildings, and other uses where animals and people may be exposed. An organophosphate (sometimes abbreviated OP) is the general name for Esters of Phosphoric acid. Flea is the Common name for any of the small wingless Insects of the order Siphonaptera (some authorities use the name Aphaniptera Beetles are the group of Insects with the largest number of known Species. The termites are a group of Social Insects usually classified at the taxonomic rank of order Isoptera (but see also taxonomy Imidacloprid is, for example, present as a main (or the sole) active ingredient in concentrations between five and ten percent in three out of the four most widely used flea treatment and preventative topical treatments for dogs in the United States; these manufacturers claim an effective killing persistence of at least four weeks. The dog ( Canis lupus familiaris) is a domesticated Subspecies of the gray wolf, a Mammal of the Canidae family of the order The compound is also used for flea treatment on cats, whose livers have only limited detoxification ability compared with dogs and humans. WikipediaManual of Style (spelling, articles should conform to one overall spelling style of English typically the one most linked to the article topic (if it is geographic The liver is a vital organ in the human body and is present in Vertebrates and some other animals

Imidacloprid is rated as "moderately toxic" acutely by the WHO and the EPA (class II or III, requiring a "Warning" or "Caution" label), and a "potential" ground water contaminant. Groundwater is Water located beneath the Ground surface in Soil pore spaces and in the Fractures of lithologic formations It is rated as an "unlikely" carcinogen by the EPA (group E), and is not listed for endocrine, reproductive, or developmental toxicity, or as a chemical of special concern by any agencies. The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation The endocrine system is an integrated system of small organs that involve the release of extracellular signaling molecules known as Hormones The endocrine system is instrumental Reproduction is the Biological process by which new individual Organisms are produced Human development is the process of Growing to maturity In biological terms this entails growth from a one-celled Zygote to an adult Human being It is not banned, restricted, cancelled, or illegal to import in any country. Tolerances for imidacloprid residue in food range from 0. 02 mg/kg in eggs to 3. 0 mg/kg in hops. Hops are the female Flower cones of the hop plant ( Humulus lupulus)

Animal toxicity is similar to that of the parent compound, nicotine; fatigue, twitching, cramps, and weakness leading to asphyxia. A muscles contraction (also known as a muscle twitch or simply twitch) occurs when a Muscle fibre generates tension through the action of Actin Cramps, sometimes called Charley horses are unpleasant often painful sensations caused by contraction or over shortening of Muscles Cramps can be caused by cold The oral LD50 (the dose which resulted in mortality of half of the test animals) of imidacloprid is 450 mg/kg body weight in rats and 131 mg/kg in mice; the 24-hour dermal LD50 in rats is greater than >5000 mg/kg. In Toxicology, the median lethal dose, LD50 (abbreviation for “Lethal Dose 50%” or LCt50 (Lethal Concentration & Time of a Rats are various medium sized long-tailed Rodents of the superfamily Muroidea A mouse (plural mice) is a small Animal that belongs to one The dermis is a layer of Skin beneath the epidermis that consists of Connective tissue, and cushions the body from stress and strain It is not irritating to eyes or skin in rabbits and guinea pigs (although some commercial preparations contain clay as an inert ingredient, which may be an irritant). Rabbits are small Mammals in the family Leporidae of the order Lagomorpha, found in several parts of the world The Guinea pig (also commonly called the cavy after its scientific name Cavia porcellus) is a species of Rodent belonging to the family Caviidae Clay is a naturally occurring material composed primarily of fine-grained Minerals which show plasticity through a variable range of Water content, and Irritation or exacerbation, in Biology and Physiology, is a state of Inflammation or painful reaction to Allergy or cell-lining damage 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/m³ of air as a dust. Inhalation (also known as respiration) is the movement of air from the external environment through the air ways and into the Alveoli. In rats subjected to a two year feeding study, no observable effect was seen at 100 ppm. At 300 ppm females showed decreased body weight gain and males showed increased thyroid lesions, while females showed increased thyroid lesions at 900 ppm. The thyroid is one of the largest Endocrine glands in the body A lesion is any abnormal tissue found on or in an organism usually damaged by disease or trauma In a one year feeding study in dogs, no observable effect was seen at 1,250 ppm, while levels up to 2,500 ppm led to hypercholesterolemia and elevated liver cytochrome p-450 measurements. Hypercholesterolemia (literally high blood cholesterol is the presence of high levels of Cholesterol in the blood. The liver is a vital organ in the human body and is present in Vertebrates and some other animals Cytochrome P450 (abbreviated CYP, P450, infrequently CYP450) is a very large and diverse superfamily of Hemoproteins found in all Domains Reproductive studies in rats resulted in no observable effect at 100 ppm and decreased pup weight at 250 ppm; developmental toxicity studies in rats showed no observable effect at 30 (mg/kg)/day and skeletal anomalies at 100 (mg/kg)/day, while in rabbits no observable effect was detected at 24 (mg/kg)/day and skeletal abnormalities at 72 (mg/kg)/day. Imidacloprid was negative for mutagenicity in 21 out of 23 different laboratory tests, but was positive for chromosomal changes in human lymphocytes and for genotoxicity in CHO cells. In Biology, a mutagen ( Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) A chromosome is an organized structure of DNA and Protein that is found in cells. A lymphocyte is a type of White blood cell in the Vertebrate Immune system. Genotoxicity describes a deleterious action on a cell genetic material affecting its integrity Chinese Hamster Ovary cells ( CHO cells are a Cell line derived from Chinese Hamster Ovary cells No carcinogenicity was seen in rats fed up to 1,800 mg/kg of imidacloprid for two years. The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation ^[2]

Imidacloprid has low vapor pressure. Vapor pressure (also known as equilibrium vapor pressure or saturation vapor pressure) is the Pressure of a Vapor in equilibrium The chemical breaks down to inorganic molecules by both photolysis and microbial action, in the air and with a half-life of 30 days in water and 27 days in soil anaerobically. Traditionally inorganic compounds are considered to be of mineral not biological origin Photodissociation, photolysis, or photodecomposition is a Chemical reaction in which a Chemical compound is broken down by Photons A microorganism (also spelled micro organism or micro-organism and also called a microbe) is an Organism that is Microscopic (usually Half-Life (computer-game page here It's already listed in the disambiguation page Soil, often typeset as SOiL, is a four piece rock band from Chicago Illinois United States founded by Shaun Glass Tom Schofield Tim King and Adam Zadel For other uses of the term "hypoxia" see Hypoxia. Hypoxia or oxygen depletion is a phenomenon that occurs in aquatic environments Although it is not "persistent" in the technical sense since it does degrade, it can have a half-life in soil under aerobic conditions of as long as 997 days, which is the cause of the concern over possible water contamination as it gradually leaches out of a hypothetical soil reservoir. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The manufacturer maintains that, when applied according to instructions, such long-term contamination is only found as the result of "repetitive application over several years" and spread to beneficial insect populations is minimal. In the body, 96% of the chemical is eliminated within 48 hours; the most important degradation product in the body is 6-chloronicotinic acid, another nicotinic neurotoxin with similar properties. Imidacloprid has, however, been reported to degrade into toxic, persistent, 2-chloropyridine. Pyridine is a Chemical compound with the formula C5[[Hydrogen H5]] N. ^[3]

Uses

The most widely used applications for imidacloprid in California are pest control in structures, turf pest control, grape growing, and head and leaf lettuce growing. California ( is a US state on the West Coast of the United States, along the Pacific Ocean. A lawn is an area of recreational or amenity land planted with grass, and sometimes Clover and other plants which are maintained at a low even height For the Tokyo University supercomputer see Gravity Pipe. GRAPE, or GRA phics P rogramming E nvironment is Lettuce ( Lactuca sativa) is a Temperate annual or Biennial plant of the daisy family Asteraceae. Other widespread crop uses are rice, grains/cereals including corn (maize), potatoes, vegetables, sugar beets, fruit, cotton, and hops. Rice is a Cereal foodstuff which forms an important part of the diet of many people worldwide and as such it is a staple food for many Maize (ˈmeɪz ( Zea mays L. ssp mays) known as corn in some countries is a cereal grain domesticated in Mesoamerica The potato is a Starchy Tuberous crop Vegetable from the perennial Solanum tuberosum of the Solanaceae The term " vegetable " generally means the edible parts of Plants The definition of the word is traditional rather than Scientific, however Sugar beet ( Beta vulgaris L a member of the Chenopodiaceae family is a plant whose root contains a high concentration of Sucrose. The term fruit has different meanings dependent on context and the term is not synonymous in Food preparation and Biology. Cotton is a soft staple Fibre that grows around the seeds of the cotton plant ( Gossypium sp Target insects include sucking insects (e. g. aphids, whiteflies, leafhoppers and planthoppers, thrips, scales, mealybugs, bugs, psyllids, and phylloxera), beetles (e. The whiteflies, comprising only the family Aleyrodidae, are small Homopterans More than 1550 species have been described Leafhopper is a common name applied to any species from the family Cicadellidae. A planthopper is any Insect in the infraorder Fulgoromorpha within the Hemiptera. The scale insects are small Insects of the order Hemiptera, generally classified as the Superfamily Coccoidea. Mealybug is the common name of insects in Pseudococcidae, a family of unarmored Scale insects found in moist warm climates Hemiptera is an order of Insects comprising around 80000 Species of Cicadas Aphids Planthoppers Leafhoppers Psyllids or jumping plant lice are small plant-feeding insects that tend to be very "host specific" i This article is about the grape phylloxera For the Genus, see Phylloxera (genus. Beetles are the group of Insects with the largest number of known Species. g. longhorn beetles, leaf beetles, Colorado potato beetles, rice water-weevils, wireworms, grubs, and flea beetles), and others (e. The longhorn beetles ( Cerambycidae; also known as long-horned beetles or more archaically longicorns) are a cosmopolitan family of Beetles Beetles in the family Chrysomelidae are commonly known as leaf beetles. The Colorado potato beetle ( Leptinotarsa decemlineata, also known as the Colorado beetle, ten-striped spearman, the ten-lined potato beetle A weevil is any Beetle from the Curculionoidea Superfamily. They are usually small less than 6  mm (¼  Inch) and herbivorous The family Elateridae is commony called click beetles (or "typical click beetles" to distinguish them form the related Cerophytidae and A larva ( Latin; plural larvae) is a juvenile form of Animal with indirect development, undergoing Metamorphosis (for example Flea beetles is a general name applied to the small jumping Beetles of the Leaf beetle family (Chrysomelidae g. lepidopterous leaf­miners, some diptera, termites, locusts, and fleas). Lepidoptera is an order of Insect that includes Moths and butterflies. Leaf miner is a term used to describe the Larvae of many different species of Insect which live in and eat the Leaf tissue of plants True flies are Insects of the Order Diptera ( Greek: di = two and pteron = wing possessing a single pair of The termites are a group of Social Insects usually classified at the taxonomic rank of order Isoptera (but see also taxonomy Locust is the Swarming phase of short-horned Grasshoppers of the family Acrididae. Flea is the Common name for any of the small wingless Insects of the order Siphonaptera (some authorities use the name Aphaniptera

When used for seed treatments, it is sold under the trade names Akteur, Amigo, Baytan Secur, Chinook, El Hombre, Escocet, Gaucho, Gaucho Blé, Gaucho CS, Gaucho Maícero, Gaucho MZ, Gaucho Orge, Gaucho Primo, Gaucho T, Gaucho MT, Gaucho XT, Genesis, Faibel, Ferial Blé, Férial Orge, Imprimo, Manta Plus, Monceren Extra, Monceren G, Monceren GT, Montur, Prestige, Prestige M, Raxil Secur, Seed-one, Sibutol Secur, Yunta and Zorro FS 236.

When used on citrus, coffee, cotton, fruits, grapes, potatoes, rice, soybeans, sugarcane, tobacco and vegetables as an insecticide spray, it is sold under the trade names Admire, Confidor, Connect, Evidence, Leverage, Muralla, Provado and Trimax.

It is marketed as Premise for termite control and Advantage in the US and Europe for flea control on pets. It is also sold under the trade names Merit, Admire, Confidor and Winner, as well as Hachikusan (in Japan).

Proper use of Advantage

When using Advantage flea control on animals, make sure to use a soap-free shampoo. The company's question hotline states that it is necessary to use a pet soap-free shampoo, otherwise the poison will be removed. However, Bayer's website claims the product remains effective even after shampooing. ^[4]

A systemic insecticide

Imidacloprid is taken up by plant roots and diffuses in the plant vascular system, where insects ingest it by sucking the plant fluids. ROOT is an object-oriented program and library developed by CERN. This is an article about the rock music band "Circulatory System" The products Confidor and Admire are meant for application via irrigation, application to the soil, or on foliage, while Gaucho is intended for use as a seed dressing, applied to the seed before sowing. Irrigation is an artificial application of water to the soil usually for assisting in growing crops In Botany, a leaf is an above-ground Plant organ specialized for Photosynthesis. A seed (in some plants referred to as a kernel) is a small embryonic Plant enclosed in a covering called the seed coat usually with some stored

Seed applied insecticides are often used to deal with numerous insects as they are easy to use and comparable in cost to most traditional insecticides used at sowing time. Some also indicate that it might be better for the environment because less chemical is required than for broadcast or banded applications, or at least because less chemical is sprayed in the air. However, some note that the use of seed-applied insecticides at each season implies the chemical is used whether there is need to fight insects or not.

Imidacloprid is receiving increased attention as a possible factor in Colony Collapse Disorder, a mysterious condition that causes sudden death of honey bee populations. Colony Collapse Disorder (or CCD) is a phenomenon in which worker bees from a beehive or Western honey bee colony abruptly disappear This article refers collectively to all true honey bees for the "common" domesticated honey bee see European honey bee Honey bees Mass die-offs of bees threaten pollination of food crops in the USA and Europe. Pollination Management is the label for horticultural practices that accomplish or enhance Pollination of a crop to improve yield or quality by understanding of the particular

See also

• Colony collapse disorder
• Pesticide toxicity to bees
• Imidacloprid effects on bee population

References

Sources

• PAN Pesticides Database

External links

• Breakdown Chart of Imidacloprid forming toxic 2-chloro pyridine
• Imidacloprid Fact Sheet, with 18 References, from the Sierra Club of Canada
• Bayer's "Expert Overview"

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