- Synthesis and insecticidal evaluation of chiral neonicotinoids analogs: The laurel wilt case
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Xyleborus sp beetles are types of ambrosia beetles invasive to the United States and recently also to Mexico. The beetle can carry a fungus responsible for the Laurel Wilt, a vascular lethal disease that can host over 300 tree species, including redbay and avocado. This problem has a great economic and environmental impact. Indeed, synthetic chemists have recently attempted to develop new neonicotinoids. This is also due to severe drug resistance to “classic” insecticides. In this research, a series of neonicotinoids analogs were synthesized, characterized, and evaluated against Xyleborus sp. Most of the target compounds showed good to excellent insecticidal activity. Generally, the cyclic compounds also showed better activity in comparison with open-chain compounds. Compounds R-13, 23, S-29, and 43 showed a mortality percent of up to 73% after 12 h of exposure. These results highlight the enantioenriched compounds with absolute R configuration. The docking results correlated with experimental data which showed both cation-π interactions in relation to the aromatic ring and hydrogen bonds between the search cavity 3C79 and the novel molecules. The results suggest that these sorts of interactions are responsible for high insecticidal activity.
- Barrera-Méndez, Felipe,Bonilla-Landa, Israel,Cuapio-Mu?oz, Ulises,Díaz de León-Gómez, Ramón E.,Enríquez-Medrano, Francisco J.,Ibarra-Juárez, Luis A.,Luna-Hernández, Saúl A.,Olivares-Romero, José L.,Pérez-Landa, Irving D.,Reyes-Luna, Alfonso,Rodríguez-Hernández, Alfredo,Suarez-Mendez, Gabriel
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Read Online
- Divergent Synthesis of Substituted Amino-1,2,4-triazole Derivatives
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A divergent efficient assembly of disubstituted 1,2,4-triazoles was established by cyclization of readily accessible N ′-nitro-2-hydrocarbylidene-hydrazinecarboximidamides with moderate to excellent yields under mild reaction conditions. This divergent synthetic strategy was achieved simply by varying the reaction conditions. Under acidic conditions, amino-1,2,4-triazoles were obtained by an intramolecular redox reaction involving the NO 2group. Control experiments and DFT studies revealed that this transformation proceeds via an intramolecular 1,3-hydride transfer pathway leading to HNO 2elimination. Under neutral conditions with water as the solvent, nitroimino-1,2,4-triazoles were obtained by oxidative intramolecular annulation under air.
- Jia, Changqing,Li, Jia-Qi,Qin, Zhaohai,Singh, Thishana,Su, Wangcang,Xiao, Yumei,Yang, Dongyan,Zhao, Fenghai
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supporting information
p. 1901 - 1910
(2021/05/18)
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- l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs
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In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good to excellent insecticidal activity. To the best of our knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the compound 9 as an excellent candidate used as the lead chiral insecticide for future development. Additionally, molecular docking with the receptor and compound 9 was carried out to gain insight into its high activity when compared to dinotefuran. Finally, the neurotoxic evaluation of compound 9 showed lower toxicity than the classic neonicotinoid dinotefuran.
- Bonilla-Landa, Israel,Cuapio-Mu?oz, Ulises,Luna-Hernández, Axel,Reyes-Luna, Alfonso,Rodríguez-Hernández, Alfredo,Ibarra-Juarez, Arturo,Suarez-Mendez, Gabriel,Barrera-Méndez, Felipe,Caram-Salas, Nadia,Enríquez-Medrano, J. Francisco,Díaz De León, Ramón E.,Olivares-Romero, José Luis
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p. 1455 - 1465
(2021/02/16)
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- Synthesis and insecticidal activity of the fluorinated galegine analogues
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The introduction of fluorine atom can increase the biological activities of the target compounds remarkably. To find more safe and efficient insecticides, natural product galegine as lead compound, a series of novel fluorinated galegine analogues were designed and synthesized. The bioassay results indicate that all the target compounds have moderate to high insecticidal activities against Hyalopterus pruni Geoffroy and Aphis gossypii Glover, in particular, compounds IIa-05, IId-02 and IIe-03 show the best insecticidal activities against Hyalopterus pruni with the mortality of 100%, 100% and 96.6%, respectively. And compounds IIa-02, IId-02, IId-04, IIc-01, IIc-02 and IId-01 show 0.6-7 times insecticidal activities against Aphis gossypii as Imidacloprid with their LC50 values are 0.28 mg/L, 0.38 mg/L, 0.33 mg/L, 0.09 mg/L, 0.03 mg/L and 0.12 mg/L, respectively The analysis of structure-activity relationship indicates that the compounds with difluoro-substituted benzene ring have more potent insecticidal activities than the single fluoro-substituted compounds.
- Wu, Qinglai,Cai, Jinlong,Zhao, Fenghai,Zhou, Ziyuan,Yang, Dongyan,Qin, Zhaohai
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p. 5773 - 5777
(2020/10/26)
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- Design, synthesis, and insecticidal activity of novel 1-Alkoxy-2-nitroguanidines
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In searching for new insecticidal lead compounds, a series of novel 1-Alkoxy-2-nitroguanidine, guadipyr analogues bearing alkoxy groups were designed, synthesized and confirmed by 1H NMR, 13C NMR, high-resolution mass spectrometry and X-ray diffraction. The primary bioassays showed that most of these compounds exhibited moderate to good insecticidal activity against Myzus persicae and Aphis gossypii. Especially, the precise insecticidal assay showed that compounds 4-02, 4-07 and 4-08 displayed excellent in vitro activity with IC50 values lower than 10 μg mL-1 to M. persicae which is comparable to guadipyr. On the other hand, the toxicity of compound 4-07 and guadipyr against honey bees was much lower than imidacloprid. The results indicated that the flexible chain on the nitrogen atom was the most crucial factor on honey bee toxicity, which existed in both neonicotinoids and guadipyr series.
- Yang, Dongyan,Wan, Chuan,Xiao, Yumei,Che, Chuanliang,Rui, Changhui,Qin, Zhaohai
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p. 1838 - 1845
(2018/02/06)
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- High activity N - oxyl new nicotine analogs and its preparation method and application (by machine translation)
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The invention belongs to the insecticide field, and in particular relates to high activity N - oxyl anabasine analogue and its preparation method and application. The invention by introducing the flexible side chain, has offered a kind of novel structure, pesticidal activity with the pyrrole insectforest quite, to the bee safely high activity N - oxyl new nicotine analogs insecticide. The insecticide solves the drug resistance of the Imidacloprid and toxic properties of the bees, can be advantageous protection of crops, horticultural plants, fruit and vegetables and the like, to prevent the emergence of the pest, increases its output, while at the same time for the activity and beneficial biological toxicity of the insecticide development explored a new path. (by machine translation)
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Paragraph 0046; 0047; 0052; 0053
(2017/07/06)
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- Targeting nitric oxide synthase with 99mTc/Re-tricarbonyl complexes containing pendant guanidino or isothiourea moieties
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The visualization of inducible nitric oxide synthase (iNOS) in vivo with specific radioactive probes could provide a valuable insight into the diseases associated with upregulation of this enzyme. Aiming at that goal, we have synthesized a novel family of conjugates bearing a pyrazolyl-diamine chelating unit for stabilization of the fac-[M(CO)3]+ core (M = 99mTc, Re) and pendant guanidino (L1 = guanidine, L 2 = N-hydroxyguanidine, L3 = N-methylguanidine, L 4 = N-nitroguanidine) or S-methylisothiourea (L5) moieties for iNOS recognition. L1-L5 reacted with fac-[M(CO) 3(H2O)]+, yielding complexes of the type fac-[M(CO)3(k3-L)]+ (M = Re/99mTc; 1/1a, L = L1; 2/2a, L = L2; 3/3a, L = L3; 4/4a, L = L4; 5/5a, L = L5), which were fully characterized by the usual analytical methods in chemistry and radiochemistry, including X-ray diffraction analysis in the case of 1. The rhenium complexes 1-5 were prepared as "cold" surrogates of the 99mTc(I) complexes. Enzymatic assays with murine purified iNOS demonstrated that L1, L2, 1 and 2 are poor NO-producing substrates. These assays have also shown that metallation of L4 and L5 (Ki > 1000 μM) gave complexes with increased inhibitory potency (4, Ki = 257 μM; 5, Ki = 183 μM). The organometallic rhenium complexes permeate through LPS-treated RAW 264.7 macrophage cell membranes, interacting specifically with the target enzyme, as confirmed by the partial suppression of NO biosynthesis (ca. 20% in the case of 4 and 5) in this cell model. The analog 99mTc(I)-complexes 1a-5a are stable in vitro, being also able to cross cell membranes, as demonstrated by internalization studies in the same cell model with compound 4a (4h, 37 °C; 33.8% internalization). Despite not being as effective as the α-amino-acid-containing metal-complexes previously described by our group, the results reported herein have shown that similar 99mTc(I)/Re(I) organometallic complexes with pendant amidinic moieties may hold potential for targeting iNOS expression in vivo.
- Oliveira, Bruno L.,Raposinho, Paula D.,Mendes, Filipa,Santos, Isabel C.,Santoes, Isabel,Ferreira, António,Cordeiro, Carlos,Freire, Ana P.,Correia, Jo?o D.G.
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supporting information; experimental part
p. 1057 - 1065
(2011/04/25)
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- Thermal behavior and nucleation kinetics of 1,5-dimethyl-2-nitroimino-1, 3, 5-triazinane crystal
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Nitroguanidine derivatives have increasingly gained attention because of their high insecticidal activities and wide spectrum. In this paper, nitroguanidine derivative 1,5-dimethyl-2-nitroimino-1, 3, 5-triazinane was synthesized, and its crystal structure was determined by X-ray technique. The thermal behaviors of 1, 5-dimethyl-2-nitroimino-1, 3, 5-triazinane in a nitrogen atmosphere were also studied under non-isothermal conditions by thermogravimetry (TG) and differential scanning calorimetry (DSC) techniques. The TG and DSC studies showed that the sample started to melt at 408.1 K with high melting enthalpy of 121.3 J/g and was stable up to at least 423.2 K, which indicated that the sample could be effectively utilized for various devices below 423.2 K. The melting entropy of 1,5-dimethyl-2-nitroimino-1, 3, 5-triazinane calculated from melting point and melting enthalpy using Eq. (1) was 51.476 J mol-1 K-1. In addition, the nucleation parameters of 1,5-dimethyl-2-nitroimino-1, 3, 5-triazinane in ethanol, such as the radius of critical nucleus and the Gibbs free energy barrier, had also been investigated based on classical nucleation theory. Crown Copyright
- Hu, Yonghong,Chen, Xiao,Yang, Wenge,Lei, Ziyu,Zhao, Cong
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experimental part
p. 170 - 174
(2010/06/18)
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- Nitrogen-rich nitroguanidyl-functionalized tetrazolate energetic salts
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A series of nitrogen-rich nitroguanidyl-functionalized tetrazolate salts paired with guanidinium-derivatized and heterocycle-based cations were synthesized and most exhibit better thermal stability, higher density and more positive heat of formation than
- Wang, Ruihu,Guo, Yong,Zeng, Zhuo,Shreeve, Jean'Ne M.
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scheme or table
p. 2697 - 2699
(2009/09/30)
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- Selective neuronal nitric oxide synthase inhibitors
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Peptidomimetic compositions for selective inhibition of neuronal nitric oxide synthase.
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Page/Page column 37
(2009/01/24)
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- CHEMOKINE RECEPTOR BINDING COMPOUNDS
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The present invention relates to chemokine receptor binding compounds, pharmaceutical compositions and their use. More specifically, the present invention relates to modulators of chemokine receptor activity, preferably modulators of CCR5. Thesd compounds demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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Page/Page column 228
(2008/06/13)
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- Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of α-D-neuraninic acid
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N-Acetylneuraminic and derivatives of formula (I) STR1 pharmaceutical formulations thereof, their use in medicine, in particular as antiviral agents and methods for their preparation are described.
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- Pyridine compounds which are useful as pesticides
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Compounds of formula STR1 wherein R1 is hydrogen, C1 -C4 alkyl or C3 -C6 cycloalkyl, R2 is hydrogen or C1 -C4 alkyl, R3 is hydrogen, C1 -C4 alkyl or C3 -C6 cycloalkyl and R4 is C1 -C4 alkyl, C3 -C6 cycloalkyl or --CH2 CH2 COOR7, or R3 and R4 together are --(CH2)4 -- or --(CH2)5 --, R5 is hydrogen, C1 -C4 alkyl, STR2 --CH2 OCH3, --CN, --COOR7 or STR3 R6 is hydrogen, chlorine, methyl or nitro, R7 and R8 are each methyl or ethyl, A is an unsubstituted or mono- to tetra-substituted, aromatic or non-aromatic, monocyclic or bicyclic, heterocyclic radical, one or two substituents being selected from the group consisting of C1 -C3 haloalkyl, cyclopropyl, halocyclopropy, C2 -C3 alkenyl, C2 -C3 alkynyl, C2 -C3 haloalkenyl, C2 -C3 haloalkynyl, C1 -C3 haloalkoxy, C1 -C3 alkylthio, C1 -C3 haloalkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro, and from one to four substituents being selected from the group consisting of C1 -C3 alkyl, C1 -C3 alkoxy and halogen, and =X is =N--NO2, =CH--NO2, =N--CN or =CH--CO--CF3, in free form or in the form of acid addition salts, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
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- Antiviral 4-substituted-2-deoxy-2,3-didehydro derivatives of alpha D-neuraminic acid
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N-Acetylneuraminic and derivatives of formula (I) (wherein R, R1, R2, R3 and R4 are defined in the specification) pharmaceutical formulations thereof, their use in medicine, in particular as antiviral agents and methods for their preparation are described.
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- SULPHOXIDES
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The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.
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