Lufenuron
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| Category | Animal Health |
| Catalog number | BBF-05878 |
| CAS | 103055-07-8 |
| Molecular Weight | 511.15 |
| Molecular Formula | C17H8Cl2F8N2O3 |
| Purity | >95% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-05878 | 1 g | $199 | In stock |
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Add to cartDescription
Lufenuron is a benzoylurea pesticide which inhibits the production of chitin in larval fleas.
Specification
| Synonyms | N-[[[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino]carbonyl]-2,6-difluorobenzamide; (RS)-1-[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea; CGA 184699; Cigna; Fluphenacur; Fuoro; Match; Match (pesticide); Match 5EC; Program |
| Shelf Life | Limited shelf life, expiry date on the label |
| Storage | Store at -20°C |
| IUPAC Name | N-[[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]carbamoyl]-2,6-difluorobenzamide |
| Canonical SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C=C2Cl)OC(C(C(F)(F)F)F)(F)F)Cl)F |
| InChI | 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) |
| InChI Key | PWPJGUXAGUPAHP-UHFFFAOYSA-N |
Properties
| Appearance | Off-White to Pale Beige Solid |
| Melting Point | 171-174°C |
| Density | 1.631±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1. Sub-lethal effects of lufenuron exposure on spotted bollworm Earias vittella (Fab): key biological traits and detoxification enzymes activity
Muhammad Shahid,Saad Jan,Muhammad Hafeez,Muhammad Nawaz,Bahar Ali,Ehsan Ali,G Mandela Fernández-Grandon,Mo Wang,Muhammad Qasim Environ Sci Pollut Res Int . 2019 May;26(14):14300-14312. doi: 10.1007/s11356-019-04655-8.
Spotted bollworm, Earias vittella, is one of the most serious and devastating insect pests of vegetables and cotton. Currently, insecticides are necessary for its control in nearly all crop systems. In this paper, we evaluate the sub-lethal effects of lufenuron on biological traits and activity of detoxification enzymes: cytochrome P450 monooxygenases, esterase, and glutathione S-transeferase (GST) in second instar larvae of E. vittella. Results showed that sub-lethal concentrations (LC15and LC40of lufenuron), prolonged larval period (at LC40= 13.86 ± 1.22 day, LC15= 13.14 ± 1.15 day, control = 12.28 ± 0.7), pupal duration (LC40= 11.1 ± day, LC15= 11.8 ± 0.28 day, control = 9.40 ± 0.52), and extended mean generation time (LC40= 27.3 ± 0.43 LC15= 29.0 ± 1.19 day, control = 26.0 ± 0.65). Sub-lethal exposure significantly prolonged the pre-adult stage, decreased pupal weight, and reduced adult longevity in the parent (F0) and F1generation. Moreover, the fecundity and egg viability were significantly lowered in parental and F1generations at both sub-lethal concentrations compared to the control. While no significant effects were noted on reproductive parameters such as the intrinsic rate of increase (r), finite rate of increase (λ), and net reproduction rate (R0) of F1generation when compared to the control. Only mean generation time (T) in F1at LC15was significantly longer compared to the LC40and control (LC40= 3.79 ± 0.37, LC15= 32.28 ± 1.55 day, control = 29.79 ± 0.55). Comparatively, the activities of cytochrome P450 monooxygenases and esterase were higher than GST in treated populations. The increase in resistance development against insecticides may possibly because of elevated activity of detoxification enzymes. These results provide useful information for monitoring resistance in integrated pest management (IPM) programs for E. vittella.
2. Cyp12a4 confers lufenuron resistance in a natural population of Drosophila melanogaster
Phillip J Daborn,Michael R Bogwitz,Melanie O'Keefe,Henry Chung,John A McKenzie,Wayn Wong,Sheena Rigby,Philip Batterham,Lorin Magoc Proc Natl Acad Sci U S A . 2005 Sep 6;102(36):12807-12. doi: 10.1073/pnas.0503709102.
Lufenuron is an insect growth regulator insecticide mainly used for the control of the cat flea. To understand mechanisms of resistance to lufenuron, we have characterized lufenuron resistance in a natural population of Drosophila melanogaster. In this study we have used precise genetic mapping to identify a mechanism of lufenuron resistance: the overexpression of the cytochrome P450 gene Cyp12a4. Cyp12a4 is predicted to encode a mitochondrial cytochrome P450 enzyme. Expression of Cyp12a4 in D. melanogaster third-instar larvae was detected in the midgut and Malpighian tubules of both lufenuron-resistant and wild-type strains. The level of Cyp12a4 expression in the midgut is higher in the lufenuron-resistant strain than in wild-type strains. Driving the expression of Cyp12a4 in the midgut and Malpighian tubules by using the GAL4/UAS gene expression system results in lufenuron resistance, but it does not result in resistance to three other insecticide classes. Transgenic expression of Cyp12a4 in a ubiquitous expression pattern results in late embryonic lethality, suggesting that high-level ectopic expression of Cyp12a4 is detrimental to development.
3. Determinants of Skin and Respiratory Exposure to Lufenuron During Spraying and Re-entry in Italian Ornamental Plants Greenhouses
Pietro Sartorelli,Maria Meniconi,Bruno Banchi,Liana Lunghini,Maria Cristina Aprea,Letizia Centi Ann Work Expo Health . 2021 Jun 12;65(5):554-565. doi: 10.1093/annweh/wxaa108.
The aim of this study was to evaluate dermal and respiratory exposure of workers to Lufenuron during spraying and re-entry on ornamental plants (stapling) in greenhouses. Potential and real skin exposure were evaluated using filter paper pads, hand contamination by washing, and respiratory exposure by personal air sampling. Dislodgeable foliar residues (DFRs) during re-entry were determined in order to calculate the dermal transfer factor (DTF). Lufenuron was analysed by liquid chromatography-mass detection. Respiratory dose (ReD) was calculated on the basis of a lung ventilation of 15-20 l min-1 and absorbed doses assuming a skin penetration of 13% and a respiratory retention of 100%. During stapling, from the dependence of exposure of hands from DFRs, the mean DTF was 0.575 cm2 h-1 (geometric mean). The ReD was 68.7-74.6 and 0.022-0.636% of the total real dose during spraying and stapling, respectively. The absorbed doses, 0.144-0.171 and 0.005-0.124 µg kg bw-1 during spraying and stapling, respectively, were less than the acceptable operator exposure level of 10 µg kg bw-1. Proper use of equipment and personal protective equipment and personal hygiene are aspects of fundamental importance on which workers must be trained. Adequate occupational hygiene studies are needed to support and verify working practices.
4. Toxicity of sediment-bound lufenuron to benthic arthropods in laboratory bioassays
I Roessink,M H S Kraak,M-C Boerwinkel,L Jollie,M J Papo,J D M Belgers,T C M Brock,J A Vonk Aquat Toxicol . 2018 May;198:118-128. doi: 10.1016/j.aquatox.2018.03.005.
This paper deals with species sensitivity distributions (SSDs) for the lipophilic insecticide lufenuron and benthic arthropods based on sediment-spiked laboratory toxicity tests. This compound that inhibits chitin synthesis and moulting of arthropods persists in sediment. Using field-collected sediment, toxicity tests were conducted with three macro-crustaceans and six insects. The Hazardous Concentration to 5% of the tested species, the HC5 (and 95% confidence limit), derived from an SSD constructed with 10d-LC50's was 2.2 (1.2-5.7) μg/g organic carbon (OC) in dry sediment. In addition, HC5 values derived from SSDs constructed with 28d-LC10 and 28-d LC50 values were 0.13 (0.02-1.50) μg/g OC and 2.0 (1.3-5.5) μg/g OC, respectively. In 28d toxicity tests with Chironomus riparius and Hyalella azteca, a higher sensitivity was observed when using lufenuron-spiked field-collected sediment than in lufenuron-spiked artificial sediment. Overall, the non-biting midge C. riparius appeared to be a representative and sensitive standard test species to assess effects of lufenuron exposure in sediment. The Tier-1 (based on standard test species), Tier-2 (based on standard and additional test species) and Tier-3 (model ecosystem approach) regulatory acceptable concentrations (RACs) for sediment-spiked lufenuron did not differ substantially. The Tier-2 RAC was the lowest. Since to our knowledge this study is the first in the open literature that evaluates the tiered approach in the sediment effect assessment procedure for pesticides, we advocate that similar evaluations should be conducted for pesticides that differ in toxic mode-of-action.
5. Acute and chronic toxicity of the benzoylurea pesticide, lufenuron, in the fish, Colossoma macropomum
Fabrício Bezerra de Sá,Pabyton Gonçalves Cadena,Elton Hugo Lima da Silva Souza,Luiz Bezerra de Carvalho Júnior,Valéria Wanderley Teixeira,Priscila Rafaela Leão Soares,Thamiris Pinheiro Santos,Marilia Ribeiro Sales Cadena,Franklin Magliano da Cunha,André Lucas Corrêa de Andrade,Amanda Rodrigues Dos Santos,Jadson Freitas da Silva,Stephannie Caroline Barros Lucas da Silva Chemosphere . 2016 Oct;161:412-421. doi: 10.1016/j.chemosphere.2016.07.033.
Lufenuron is a benzoylurea insecticide that interfere in chitin synthesis in insects. Although lufenuron is widely used in agriculture and aquaculture, rare are studies described that relates to possible toxic effects in fish. This work aimed to evaluate acute and chronic toxic effects of benzoylurea pesticide (lufenuron) on biological parameters of Colossoma macropomum (Tambaqui). In the acute test, juveniles of Tambaqui were divided into control group and five experimental groups with exposure from 0.1 to 0.9 mg/L of lufenuron for 96 h. Animals were also submitted to chronic toxicity test for four months in concentrations of 0.1 and 0.3 mg/L of lufenuron, the concentration used in the treatment of ectoparasites in fish and 50% of LC50 96 h, respectively. The presence of hemorrhages was observed in eyes, fins and operculum of fish exposed to 0.7 and 0.9 mg/L of lufenuron. Histological analysis showed changes in the morphology of fish gills submitted to acute toxicity test, as lamellar aneurysm and blood congestion inside lamellae. Lufenuron promoted damage in fish retina as in ability to respond to stimuli in photoreceptors and in ON-bipolar cells in acute test. In chronic test, blood glucose analysis and morphometric parameters showed no significant differences (p > 0.05). In general, Tambaqui exhibited behaviors associated with stress when exposed to lufenuron. Thus, lufenuron showed several toxic effects in relation to biological parameters in Tambaqui. This concerns about the use and discard of lufenuron, and indicates the requirement of environmental actions to prevent potential contamination of aquatic biota.
6. Setting of import tolerances for lufenuron in various commodities of plant and animal origin
Alois Stanek,EFSA (European Food Safety Authority),Luna Greco,Renata Leuschner,Ileana Miron,Alejandro Rojas,Benedicte Vagenende,Jose Oriol Magrans,Ragnor Pedersen,Alba Brancato,Angela Sacchi,Stefanie Nave,Aija Kazocina,Miguel Santos,Alessia Verani,Luis Carrasco Cabrera,Lucien Ferreira,Samira Jarrah,Anne Theobald,Giovanni Bernasconi,Hermine Reich,Maria Anastassiadou EFSA J . 2020 Aug 18;18(8):e06228. doi: 10.2903/j.efsa.2020.6228.
In accordance with Article 6 of Regulation (EC) No 396/2005, the applicant Syngenta Crop Protection AG submitted a request to the competent national authority in Portugal to set import tolerances for the active substance lufenuron in grapefruits, oranges, limes, pome fruits, peppers, coffee, sugar canes, muscle, fat, liver and kidney on the basis of the authorised uses of lufenuron in Brazil, Chile and Morocco. The data submitted in support of the request were found to be sufficient to derive maximum residue level (MRL) proposals for all commodities under assessment. For oranges, limes, pome fruits, peppers and coffee beans and commodities of animal origin, the submitted data indicated no need to modify the existing EU MRLs. For grapefruits and sugar cane, the residue data indicated that higher MRLs would be needed. Adequate analytical methods for enforcement are available to control the residues of lufenuron in plant and animal matrices. Based on the risk assessment results, EFSA concluded that the existing EU uses and the authorised uses of lufenuron in Brazil, Chile and Morocco will not result in chronic consumer exposure exceeding the toxicological reference value. Considering, however, that the estimated exposure is close to the acceptable daily intake (ADI) and in the light of the expiry of the approval of the active substance, EFSA recommends the review of the existing MRLs taking into account that the MRLs based on the EU uses will become obsolete.
7. Lufenuron suppresses the resistance of Formosan subterranean termites (Isoptera: Rhinotermitidae) to entomopathogenic bacteria
Cai Wang,Bal K Gautam,Gregg Henderson J Econ Entomol . 2013 Aug;106(4):1812-8. doi: 10.1603/ec13068.
Pesticides can negatively affect insect immunity. Although studies show that Formosan subterranean termites, Coptotermes formosanus Shiraki, are resistant to microbial infections, the effects of pesticides on disease resistance is not well studied. In this study, C. formosanus previously fed lufenuron was exposed to each of the three entomopathogenic bacteria, Pseudomonas aeruginosa (Schroeter) Migula, Serratia marcescens Bizio, and Bacillus thuringiensis Berliner subsp. israelensis. We found that termite mortality was significantly higher and synergistic in the combination of lufenuron and P. aeruginosa compared with treatment of lufenuron or P. aeruginosa alone. Other bacteria and lufenuron combinations were not quite as effective. Interestingly, only in treatments without lufenuron did termites show carcass-burying behavior. The results indicate that lufenuron, a chitin synthesis inhibitor, can suppress Formosan subterranean termite resistance to P. aeruginosa. Possible suppression mechanisms are discussed.
8. Lufenuron can be transferred by gravid Aedes aegypti females to breeding sites and can affect their fertility, fecundity and blood intake capacity
Laura Harburguer,Paula V Gonzalez Parasit Vectors . 2020 May 15;13(1):257. doi: 10.1186/s13071-020-04130-1.
Background:Aedes aegypti (L.) is the main vector of dengue, yellow fever, Zika and chikungunya viruses. A new method for controlling this mosquito has been developed based on the possibility that wild adult mosquitoes exposed to artificial resting sites contaminated with a larvicide, can disseminate it to larval breeding sites, is named "auto-dissemination". The present study was undertaken to evaluate if a chitin synthesis inhibitor like lufenuron can be disseminated to larval breeding sites and prevent adult emergence and also if forced contact of Ae. aegypti females with treated surfaces can affect its fertility, fecundity, and blood intake capacity.Methods:Larval susceptibility to lufenuron was measured through EI50and EI90. On the other hand, gravid females were exposed by tarsal contact to lufenuron-treated papers, we used the WHO susceptibility test kit tube to line the papers, and 1, 3 or 5 females for the transference. We also evaluated if the exposure of female mosquitoes to lufenuron-treated papers (0.4 and 1 mg a.i./cm2) has an effect on their fertility, fecundity or in the ability to feed on blood. In each assay 12-15 female mosquitoes were exposed to lufenuron for 1 h, 24 h before blood meal (BBM) or 24 h after a blood meal (ABM).Results:Lufenuron proved to be very active against Ae. aegypti larvae with an EI50of 0.164 ppb and EI90of 0.81 ppb. We also found that lufenuron can be transferred by females from treated surfaces to clean containers causing the inhibition of emergence of the larvae (between 30 and 50%). This effect was dependent on the concentration applied on the paper and the number of females added to each cage.Conclusions:This study introduces an innovation by first exploring the possibility that an insect growth regulator (IGR) belonging to the group of benzoylphenyl ureas, such as lufenuron, can be transferred by gravid females to breeding sites and that at the same time can have an effect on fertility, fecundity and blood intake capacity of adult mosquitoes.
9. Lufenuron induces reproductive toxicity and genotoxic effects in pregnant albino rats and their fetuses
Abdel Rahman T Ahmed,Aya A Mahmoud,Amel R Omar,Wesam T Basal Sci Rep . 2020 Nov 11;10(1):19544. doi: 10.1038/s41598-020-76638-6.
Insecticides and other agrochemicals have become indispensable components of the agricultural system to ensure a notable increase in crop yield and food production. As a natural consequence, chemical residues result in significantly increased contamination of both terrestrial and aquatic ecosystems. The present study evaluated the teratogenic, genotoxic, and oxidative stress effects of residual-level lufenuron exposure on pregnant rats during the organogenesis gestational period of both mother and fetus. The tested dams were divided into three groups; control (untreated), low-dose group (orally administered with 0.4 mg/kg lufenuron) and high-dose group (orally administered with 0.8 mg/kg lufenuron). The dams of the two treatment groups showed teratogenic abnormalities represented by the asymmetrical distribution of fetuses in both uterine horns, accompanied by observed resorption sites and intensive bleeding in the uterine horns, whereas their fetuses suffered from growth retardation, morphologic malformations, and skeletal deformations. Histologic examination of the liver and kidney tissues obtained from mothers and fetuses after lufenuron exposure revealed multiple histopathologic changes. DNA fragmentation and cell cycle perturbation were also detected in the liver cells of lufenuron-treated pregnant dams and their fetuses through comet assay and flow cytometry, respectively. Moreover, lufenuron-induced oxidative stress in the liver of mothers and fetuses was confirmed by the increased malondialdehyde levels and decreased levels of enzymatic antioxidants (glutathione peroxidase and superoxide dismutase). Taken together, it can be concluded that lufenuron has a great potential in exerting teratogenic, genotoxic, and oxidative stresses on pregnant rats and their fetuses upon chronic exposure to residual levels during the organogenesis gestational period. The obtained results in the present study imply that women and their fetuses may have the same risk.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
