Lufenuron

Last updated
Lufenuron
Lufenuron 200.svg
Lufenuron-3D-balls.png
Names
IUPAC name
1-[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea
Other names
N-[[[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino]carbonyl]-2,6-difluorobenzamide
Fluphenacur
U.S. EPA PC Code: 118205
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.101.025 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C17H8Cl2F8N2O3/c18-6-5-11(32-17(26,27)14(22)16(23,24)25)7(19)4-10(6)28-15(31)29-13(30)12-8(20)2-1-3-9(12)21/h1-5,14H,(H2,28,29,30,31) Yes check.svgY
    Key: PWPJGUXAGUPAHP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H8Cl2F8N2O3/c18-6-5-11(32-17(26,27)14(22)16(23,24)25)7(19)4-10(6)28-15(31)29-13(30)12-8(20)2-1-3-9(12)21/h1-5,14H,(H2,28,29,30,31)
    Key: PWPJGUXAGUPAHP-UHFFFAOYAQ
  • Clc1cc(c(Cl)cc1OC(F)(F)C(F)C(F)(F)F)NC(=O)NC(=O)c2c(F)cccc2F
Properties
C17H8Cl2F8N2O3
Molar mass 511.15 g·mol−1
Melting point 174 °C (345 °F; 447 K)
Pharmacology
QP53BC01 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Lufenuron is the active ingredient in the veterinary flea control medication Program, and one of the two active ingredients in the flea, heartworm, and anthelmintic medicine milbemycin oxime/lufenuron (Sentinel).

Lufenuron is stored in the animal's body fat and transferred to adult fleas through the host's blood when they feed. Adult fleas transfer it to their growing eggs through their blood, and to hatched larvae feeding on their excrement. It does not kill adult fleas.[ citation needed ]

Lufenuron, a benzoylurea pesticide, inhibits the production of chitin in insects. Without chitin, a larval flea will never develop a hard outer shell (exoskeleton). With its inner organs exposed to air, the insect dies from dehydration soon after hatching or molting (shedding its old, smaller shell).[ citation needed ]

Lufenuron is also used to fight fungal infections, since fungus cell walls are about one third chitin. [1]

Lufenuron is also sold as an agricultural pesticide for use against lepidopterans, eriophyid mites, and western flower thrips. It is an effective antifungal in plants. [2]

Related Research Articles

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. The major use of Insecticides is agriculture, but they are also used in home and garden, industrial buildings, vector control and control of insect parasites of animals and humans. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

<span class="mw-page-title-main">Biological pest control</span> Controlling pests using other organisms

Biological control or biocontrol is a method of controlling pests, whether pest animals such as insects and mites, weeds, or pathogens affecting animals or plants by using other organisms. It relies on predation, parasitism, herbivory, or other natural mechanisms, but typically also involves an active human management role. It can be an important component of integrated pest management (IPM) programs.

<span class="mw-page-title-main">Pest (organism)</span> Organism harmful to humans/our concerns

A pest is any organism harmful to humans or human concerns. The term is particularly used for creatures that damage crops, livestock, and forestry or cause a nuisance to people, especially in their homes. Humans have modified the environment for their own purposes and are intolerant of other creatures occupying the same space when their activities impact adversely on human objectives. Thus, an elephant is unobjectionable in its natural habitat but a pest when it tramples crops.

<span class="mw-page-title-main">Thrips</span> Order of insects

Thrips are minute, slender insects with fringed wings and unique asymmetrical mouthparts. Entomologists have described approximately 7,700 species. They fly only weakly and their feathery wings are unsuitable for conventional flight; instead, thrips exploit an unusual mechanism, clap and fling, to create lift using an unsteady circulation pattern with transient vortices near the wings.

<span class="mw-page-title-main">Selamectin</span> Topical parasiticide for dogs and cats

Selamectin, sold under the brand name Revolution, among others, is a topical parasiticide and anthelminthic used on dogs and cats. It treats and prevents infections of heartworms, fleas, ear mites, sarcoptic mange (scabies), and certain types of ticks in dogs, and prevents heartworms, fleas, ear mites, hookworms, and roundworms in cats. It is structurally related to ivermectin and milbemycin. Selamectin is not approved for human use.

A biopesticide is a biological substance or organism that damages, kills, or repels organisms seen as pests. Biological pest management intervention involves predatory, parasitic, or chemical relationships.

<span class="mw-page-title-main">Dichlorvos</span> Insect killing chemical, organophosphate

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.

<span class="mw-page-title-main">Phytoseiidae</span> Family of mites

The Phytoseiidae are a family of mites which feed on thrips and other mite species. They are often used as a biological control agent for managing mite pests. Because of their usefulness as biological control agents, interest in Phytoseiidae has steadily increased over the past century. Public awareness of the biological control potential of invertebrates has been growing, though mainly in the US and Europe. In 1950, there were 34 known species. Today, there are 2,731 documented species organized in 90 genera and three subfamilies.

<span class="mw-page-title-main">Benzoylurea</span> Chemical compound

Benzoylureas (BPUs) are chemical derivatives of N-benzoyl-N-phenylurea, which are used as insecticides. They do not directly kill the insect, but disrupt moulting and egg hatch, and thus act as insect growth regulators. They act by inhibiting chitin synthase, preventing the formation of chitin in the insect's body.

<span class="mw-page-title-main">Western flower thrips</span> Vegetable pest, SW US native, invasive

The western flower thrips [Frankliniella occidentalis (Pergande)] is an invasive pest insect in agriculture. This species of thrips is native to the Southwestern United States but has spread to other continents, including Europe, Australia, and South America via transport of infested plant material.

<span class="mw-page-title-main">Disease vector</span> Agent that carries and transmits an infectious pathogen into another living organism

In epidemiology, a disease vector is any living agent that carries and transmits an infectious pathogen such as a parasite or microbe, to another living organism. Agents regarded as vectors are mostly blood-sucking insects such as mosquitoes. The first major discovery of a disease vector came from Ronald Ross in 1897, who discovered the malaria pathogen when he dissected the stomach tissue of a mosquito.

<i>Scirtothrips dorsalis</i> Species of thrip

Scirtothrips dorsalis, the chilli thrips or yellow tea thrips, is an extremely successful invasive species of pest-thrips which has expanded rapidly from Asia over the last twenty years, and is gradually achieving a global distribution. It has most recently been reported in St. Vincent (2004) Florida (2005), Texas (2006), and Puerto Rico (2007). It is a pest of economic significance with a broad host range, with prominent pest reports on crops including pepper, eggplant, mango, citrus, strawberry, grapes, cotton, tea, peanuts, blueberry, and roses. Chilli thrips appear to feed preferentially on new growth, and infested plants usually develop characteristic wrinkled leaves, with distinctive brown scarring along the veins of leaves, the buds of flowers, and the calyx of fruit. Feeding damage can reduce the sale value of crops produced, and in sufficient numbers, kill plants already aggravated by environmental stress. This thrips has also been implicated in the transmission of three tospoviruses, but there is some controversy over its efficiency as a vector.

<span class="mw-page-title-main">Methiocarb</span> Chemical compound

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

<span class="mw-page-title-main">Dinotefuran</span> Chemical compound

Dinotefuran is an insecticide of the neonicotinoid class developed by Mitsui Chemicals for control of insect pests such as aphids, whiteflies, thrips, leafhoppers, leafminers, sawflies, mole cricket, white grubs, lacebugs, billbugs, beetles, mealybugs, and cockroaches on leafy vegetables, in residential and commercial buildings, and for professional turf management. Its mechanism of action involves disruption of the insect's nervous system by inhibiting nicotinic acetylcholine receptors. In order to avoid harming beneficial insects such as bees, it should not be applied during bloom.

<span class="mw-page-title-main">Mites of livestock</span> Small crawling animals related to ticks and spiders

Mites are small crawling animals related to ticks and spiders. Most mites are free-living and harmless. Other mites are parasitic, and those that infest livestock animals cause many diseases that are widespread, reduce production and profit for farmers, and are expensive to control.

<span class="mw-page-title-main">Novaluron</span> Chemical compound

Novaluron, or (±)-1-[3-chloro-4-(1,1,2-trifluoro-2-trifluoro- methoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea, is a chemical with pesticide properties, belonging to the class of insecticides called insect growth regulators. It is a benzoylphenyl urea developed by Makhteshim-Agan Industries Ltd.. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals, and cotton. Patents and registrations have been approved or are ongoing in several other countries throughout Europe, Asia, Africa, South America, and Australia. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms and value it as an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.

Dicyphus hesperus is a species of true bug in the family Miridae. It is a generalist predator of other insects and also feeds on plant tissues. It is native to North America and has been used there in biological control of agricultural pests, especially whitefly on tomatoes.

Flea treatments are procedures used to treat flea infestations in human or animal populations. They may treat both the itching caused by bites and may remove or kill the fleas themselves.

Frankliniella schultzei, the common blossom thrips or cotton thrips, is a species of thrips in the family Thripidae. It is found in many parts of the world and is an important pest insect in agriculture.

References

  1. Ben-Ziony, Yair; Arzi, Boaz (2000). "Use of lufenuron for treating fungal infections of dogs and cats: 297 cases (1997-1999)". Journal of the American Veterinary Medical Association. 217 (10): 1510–3. doi:10.2460/javma.2000.217.1510. PMID   11128542.
  2. Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V N (2014). The Pesticide Encyclopedia. Wallingford, Oxfordshire UK Boston, MA: CABI. p. 283. ISBN   978-1-78064-014-3 . Retrieved Nov 22, 2018. Lufenuron, a chitin synthesis inhibitor, is an effective agent against lepidopteran members in crops, eriophid mites and western flower thrips. In non-crop situations too, lufenuron is effective against fleas on animals and on cockroaches in households. This chemical also acts as an anti-fungal agent in plants. ... According to the WHO, lufenuron is a Class III toxin (slightly hazardous). It is safe on mammals, since it is not broken down by the liver or kidneys.