Buprofezin

Last updated
Buprofezin
Buprofezin structure.png
Names
IUPAC name
(2Z)-3-Isopropyl-2-[(2-methyl-2-propanyl)imino]-5-phenyl-1,3,5-thiadiazinan-4-one
Other names
Buprofezin
Identifiers
  • 69327-76-0 Yes check.svgY
3D model (JSmol)
8625926
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.125.182 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 614-948-3
KEGG
PubChem CID
UNII
  • InChI=1S/C16H23N3OS/c1-12(2)19-14(17-16(3,4)5)21-11-18(15(19)20)13-9-7-6-8-10-13/h6-10,12H,11H2,1-5H3/b17-14-
    Key: PRLVTUNWOQKEAI-VKAVYKQESA-N
  • CC(C)N1\C(=N\C(C)(C)C)\SCN(C1=O)c2ccccc2
Properties
C16H23N3OS
Molar mass 305.44 g·mol−1
Hazards
GHS labelling: [1]
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H373, H410
P260, P273, P314, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Buprofezin is an insecticide used for control of insect pests such as mealybugs, leafhoppers and whitefly on vegetable crops. It is a growth regulator, acting as an inhibitor of chitin synthesis. [2] It is banned in some countries due to its negative environmental impacts, being especially toxic to aquatic organisms as well as non-target insects, though is of low toxicity to humans and other mammals. [3]

Related Research Articles

Chitin Long-chain polymer of a N-acetylglucosamine

Chitin (C8H13O5N)n ( KY-tin) is a long-chain polymer of N-acetylglucosamine, an amide derivative of glucose. The second most abundant polysaccharide in nature (behind only cellulose), it is a primary component of cell walls in fungi, the exoskeletons of arthropods such as crustaceans and insects, and the radulae, cephalopod beaks and gladii of molluscs. It is also synthesised by at least some fish and lissamphibians. The structure of chitin is comparable to cellulose, forming crystalline nanofibrils or whiskers. It is functionally comparable to the protein keratin. Chitin has proved useful for several medicinal, industrial and biotechnological purposes.

Azadirachtin Chemical compound

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is a highly oxidized tetranortriterpenoid which boasts a plethora of oxygen-bearing functional groups, including an enol ether, acetal, hemiacetal, tetra-substituted epoxide and a variety of carboxylic esters.

Antifungal Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC).

Cytarabine Chemical compound (chemotherapy medication)

Cytarabine, also known as cytosine arabinoside (ara-C), is a chemotherapy medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and non-Hodgkin's lymphoma. It is given by injection into a vein, under the skin, or into the cerebrospinal fluid. There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.

Ouabain Chemical substance

Ouabain or also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium-potassium ion pump. However, adaptations to the alpha-subunit of the Na+/K+-ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore- insect species, that have resulted in toxin resistance.

Hydroxycarbamide Medical drug

Hydroxycarbamide, also known as hydroxyurea, is a medication used in sickle-cell disease, essential thrombocythemia, chronic myelogenous leukemia and cervical cancer. In sickle-cell disease it increases fetal hemoglobin and decreases the number of attacks. It is taken by mouth.

Lufenuron Chemical compound

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

Lupinine Chemical compound

Lupinine is a quinolizidine alkaloid present in the genus Lupinus of the flowering plant family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound as well as a vast number of studies on its biosynthesis from its natural precursor, lysine. Studies have shown that lupinine hydrochloride is a mildly toxic acetylcholinesterase inhibitor and that lupinine has an inhibitory effect on acetylcholine receptors. The characteristically bitter taste of lupin beans, which come from the seeds of Lupinus plants, is attributable to the quinolizidine alkaloids which they contain, rendering them unsuitable for human and animal consumption unless handled properly. However, because lupin beans have potential nutritional value due to their high protein content, efforts have been made to reduce their alkaloid content through the development of "sweet" varieties of Lupinus.

Glycosyltransferase Class of enzymes that catalyze the transfer of glycosyl groups to an acceptor

Glycosyltransferases are enzymes that establish natural glycosidic linkages. They catalyze the transfer of saccharide moieties from an activated nucleotide sugar to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen- carbon-, nitrogen-, or sulfur-based.

Phytotoxins are substances that are poisonous or toxic to the growth of plants. Phytotoxic substances may result from human activity, as with herbicides, or they may be produced by plants, by microorganisms, or by naturally occurring chemical reactions.

Benzoylurea chemical compound

Benzoylureas are chemical derivatives of N-benzoyl-N′-phenylurea (benzoylurea). They are best known for their use as insecticides. They act as insect growth regulators by inhibiting synthesis of chitin in the insect's body.

Temsirolimus

Temsirolimus, sold under the brand name Torisel, is an intravenous drug for the treatment of renal cell carcinoma (RCC), developed by Wyeth Pharmaceuticals and approved by the U.S. Food and Drug Administration (FDA) in May 2007, and was also approved by the European Medicines Agency (EMA) in November 2007. It is a derivative and prodrug of sirolimus.

Pumiliotoxin 251D Chemical compound

Pumiliotoxin 251D is a toxic organic compound. It is found in the skin of poison frogs from the genera Dendrobates, Epipedobates, Minyobates, and Phyllobates and toads from the genus Melanophryniscus. Its name comes from the pumiliotoxin family (PTXs) and its molecular mass of 251 Daltons. When the toxin enters the bloodstream through cuts in the skin or by ingestion, it can cause hyperactivity, convulsions, cardiac arrest and ultimately death. It is especially toxic to arthropods, even at low concentrations.

An insect growth regulator (IGR) is a substance (chemical) that inhibits the life cycle of an insect. IGRs are typically used as insecticides to control populations of harmful insect pests such as cockroaches and fleas.

Diflubenzuron Chemical compound

Diflubenzuron is an insecticide of the benzoylurea class. It is used in forest management and on field crops to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths. It is a widely used larvicide in India for control of mosquito larvae by public health authorities. Diflubenzuron is approved by the WHO Pesticide Evaluation Scheme.

Antifeedant

Antifeedants are organic compounds produced by plants to inhibit attack by insects and grazing animals. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but instead confer longevity. Antifeedants exhibit a wide range of activities and chemical structures as biopesticides. Examples include rosin, which inhibits attack on trees, and many alkaloids, which are highly toxic to specific insect species.

Novaluron 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 and South America, as well as 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 an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.

Etoxazole Chemical compound

Etoxazole is a narrow spectrum systemic acaricide used to combat spider mites. It targets a variety of mites in the egg, larvae and nymph stages however not the adult stage. It also exhibits insecticidal activity towards aphids, the green rice leafhopper and diamondback moth. The mode of action was originally suspected to inhibit the molting process but has since been shown to inhibit chitin synthesis. Resistance due to its high efficacy and cross resistance when used with other acaricides are both of concern similar to was seen in the fast development of cross resistance in the previous generation of acaricides. The LC50 for resistant mite strains has been observed over 100,000 times greater than that of susceptible strains. Thus resistance management strategies are important in order to limit the increase of etoxazole resistant mite strains.

A steroidogenesis inhibitor, also known as a steroid biosynthesis inhibitor, is a type of drug which inhibits one or more of the enzymes that are involved in the process of steroidogenesis, the biosynthesis of endogenous steroids and steroid hormones. They may inhibit the production of cholesterol and other sterols, sex steroids such as androgens, estrogens, and progestogens, corticosteroids such as glucocorticoids and mineralocorticoids, and neurosteroids. They are used in the treatment of a variety of medical conditions that depend on endogenous steroids.

Modeccin is a toxic lectin, a group of glycoproteins capable of binding specifically to sugar moieties. Different toxic lectins are present in seeds of different origin. Modeccin is found in the roots of the African plant Adenia digitata. These roots are often mistaken for edible roots, which has led to some cases of intoxication. Sometimes the fruit is eaten, or a root extract is drunk as a manner of suicide.

References

  1. "Buprofezin". pubchem.ncbi.nlm.nih.gov. Retrieved 26 December 2021.
  2. Liu TX, Chen TY. Effects of the chitin synthesis inhibitor buprofezin on survival and development of immatures of Chrysoperla rufilabris (Neuroptera: Chrysopidae). J Econ Entomol. 2000 Apr;93(2):234-9. PMID   10826167
  3. Qureshi IZ, Bibi A, Shahid S, Ghazanfar M. Exposure to sub-acute doses of fipronil and buprofezin in combination or alone induces biochemical, hematological, histopathological and genotoxic damage in common carp (Cyprinus carpio L.). Aquat Toxicol. 2016 Oct;179:103-14. doi: 10.1016/j.aquatox.2016.08.012. PMID   27595653