Benzoyl Phenyl Research Articles

Mini-review highlighting toxic effects of triflumuron in insects and mammalian systems.

Pesticides have been used to kill pests such as insects, fungi, rodents, and unwanted plants. As these compounds are potentially toxic to the target organisms, they could also be harmful to human health and the environment. Several chronic adverse effects have been identified even after months or years of exposure. The adverse effects of pesticides on the agricultural ecosystem have been a matter of concern in recent decades. In this review, we present an overview of the studies, including our previous studies, monitoring currently used pesticides in the Tunisian agricultural soils that belong to the class of insect growth regulators (IGRs). Triflumuron (TFM) is a benzoyl phenyl urea insecticide belonging to the class of IGRs. TFM is widely used around the world to increase crop yield by protecting them from damage caused by insects. TFM works by inhibiting the synthesis of chitin, an essential part of the insect cuticle, making it susceptible to pathogens and deformities. Consequently, insects become more susceptible to pathogens and malformations. However, studies revealing its toxicity and its mode of action in mammalian systems remain very limited. The aim of this review is to better inform the community about the impact of TFM on crops, the environment, and human beings by summarizing its toxic effects.

Corrosion protection properties of poly((benzoyl phenyl) methacrylate-co-methoxy ethylmethacrylate) coating on mild steel

The copolymer, poly(BPM-CO-MOEMA) has been synthesized from different monomer feed ratios of benzoylphenyl methacrylate (BPM) and methoxyethyl methacrylate (MOEMA) was achieved using the free radical solution polymerization technique. The thermal stability of the synthesized copolymers was studied by using TGA and DSC. The molecular weight of the copolymer was determined by GPC. The corrosion protection efficiency of the mild steel specimens coated with different mole ratios of the copolymer has been investigated using electrochemical techniques like EIS and potentiodynamic polarization studies in 1 M H2SO4. The observation of electrochemical results confirmed that the copolymer coating shows good protection efficiency for mild steel in the corrosive media. The surface and morphological investigations also confirm the barrier effect of the copolymer film on the metal surface against the invasion of corrosive ions.

Synthesis and Acylation for Enaminoketohydrazides Derived from 2,2-Dialkyl-2,3-dihydrobenzo[f]isoquinolines

The reaction of 6,6-dialkyl-5,6-dihydrobenzo[f]pyrrolo[2,1-a]isoquinoline-8,9-diones with hydrazine is used to prepare enaminoketohydrazides of the 2,2-dialkyl-2,3-dihydrobenzo[f]isoquinoline series, which are polyfunctional reagents. The acylation of the synthesized hydrazides with two equivalents of acylating reagents, such as benzoyl chloride, phenyl isocyanate, phenyl isothiocyanate, and allyl isothiocyanate, involves exclusively the terminal NH2 group of the hydrazide fragment. The acylation with two equivalents of acetyl chloride leads to the substitution of both hydrogen atoms at the terminal NH2 group; the structure of the resulting N,N-diacyl derivative is proved by X-ray diffraction analysis.

Intramolecular hydrogen bond directed stable conformations of benzoyl phenyl oxalamides: unambiguous evidence from extensive NMR studies and DFT-based computations.

A number of benzoyl phenyl oxalamide derivatives have been synthesized and characterized by the extensive utility of one- and two-dimensional NMR experimental techniques. The manifestation of intramolecular hydrogen bonds in all of the synthesized molecules, convincingly established using NMR studies, governs the stable conformations of the molecules. In the fluorine substituted molecules, the coupling between two NMR active nuclei mediated through hydrogen bonds has been detected. The measured chemical shift difference of an NH proton has been employed to calculate the energy of the HBs. NMR analysis revealed the electrostatic nature of the hydrogen bonds in all of the molecules. The NMR experimental findings have been validated using Density Functional Theory (DFT)-based Non Covalent Interactions (NCIs) and Quantum Theory of Atoms In Molecules (QTAIM) computations.

Characterization of Side Chain Liquid Crystal Polymers Type on Blending Polymer of Cholesteryl Acrylate with Methyl Phenyl Benzoyl Acrylate

Characterization of Side Chain Liquid Crystal Polymers Type on Blending Polymer of Cholesteryl Acrylate with Methyl Phenyl Benzoyl Acrylate

Opening of pyridine ring with benzoyl(phenyl)acetylene in the presence of water with formation of 5-aminopenta-2,4-dienal

Opening of pyridine ring with benzoyl(phenyl)acetylene in the presence of water with formation of 5-aminopenta-2,4-dienal

Polymerization of Blending Cholesteryl Acrylate and Methyl Phenyl Benzoyl Acrylate

Liquid crystal is a material which is between solid and liquid phase and commonly called mesophase. Blends of liquid crystal are of great interest because of their unique optical properties. Blending in this study using two monomers of liquid crystal were cholesteryl acrylate and methyl phenyl benzoyl acrylate. The polymerization process using uv curing techniques by irradiation UV ray and without irradiation UV ray. Polymerization of blending liquid crystal acrylate using initiator 2-hydroxy-2-methyl-1-phenylpropane. Based on peak at GPC curve of polymerization by irradiation UV ray, type of that polymer is copolymer. Therefore the polymerization without UV ray, type of that polymer is homopolymer. SEM images of liquid crystal acrylate polymer showed lamella chain models that are characteristic of a polymer chains. Type of polymer liquid crystal acrylate was the type of Side Chain Liquid Crystalline Polymers (SCLCPs). Therefore acrylate polymer liquid crystal in this research has semi-crystalline phase, which contained crystalline phase and amorphous phase on the XRD pattern. The results of FT-IR spectroscopic characterization of the two monomers showed a peak at the wave number of 1600.43 cm -1 and 1622.86 cm-1 which indicates a double bond (C=C) were obtained from acrylation. While the spectroscopy on the product blending the wave number of the peak regions is reduced that shows that carbon double bonds (C=C) in the acrylate group has polymerized. It also strengthened with a very sharp peak for CC functional groups on the wave number of 2855.15 cm-1. The results of this study indicate that the liquid crystal polymer acrylic polymerization results with radiation UV ray and without UV ray, respectively absorb light in the UV wavelength region 363 nm and 351 nm.

Reactions of an Al–P-Based Frustrated Lewis Pair with Carbonyl Compounds: Dynamic Coordination of Benzaldehyde, Activation of Benzoyl Chloride, and Al–C Bond Cleavage with Benzamide

Treatment of the Al/P-based frustrated Lewis pair (FLP) Mes2PC(═CHPh)Al(CMe3)2 (1) with benzaldehyde afforded the adduct 2 with a five-membered AlCPCO heterocycle. The carbonyl oxygen atom is bound to aluminum and the carbonyl carbon atom to phosphorus. 2 is dynamic in solution at room temperature, which results in a fast equilibration of the enantiomeric molecules by cleavage of the P–C and fast rotation about the Al–O bond. Benzoyl chloride and 1 yielded three products (3–5). Quinoid structures were formed by C–Cl bond activation, chlorine abstraction, and loss of aromaticity in the benzoyl phenyl group. Alkylation of the p-C atom by an AlCMe3 group completed the transformation and resulted concomitantly in the formation of derivatives with Al–Cl bonds. The complexes may be described as a ketene molecule coordinated to FLP 1. Benzamide reacted as a proton donor and gave cleavage of the Al–C bond to the vinylic carbon atom of 1. An alkenylphosphine, Mes2PC(H)═C(H)CMe3, and a dinuclear amidate complex with two dialkylaluminum groups bridged by two chelating ligands were isolated.

Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine

Benzoyl phenyl urea, a class of insect growth regulator’s acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a–f) and benzoylcarvacryl urea (BCU, 5a–f) derivatives were prepared and characterized by elemental analysis, IR, 1H and 13C NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine.

Design and development of novel insect growth regulators: Synthesis, characterization and effect of benzoyl thymyl thioureas and ureas on total haemocyte count of Dysdercus koenigii

Insect-growth regulators (IGRs) have been receiving foremost attention as potential means of selective insect control. Benzoyl phenyl urea (BPU) is a well-known IGR having chitin synthesis inhibitor activity. Mimics of BPU have been synthesized by suitable derivatization of a naturally occurring monoterpenoid, thymol (2-isopropyl-5-methyl phenol) to form a = series of substituted benzoyl thymyl thioureas (BTTUs) [IVa-f] and benzoyl thymyl ureas (BTUs) [Va-f]. The synthesized compounds have been characterized by 1H and 13C NMR, LC-MS and elemental analysis. These derivatives have been screened for their effect on total haemocyte count of Dysdercus koenigii. It has been observed that the introduction of substituted benzoyl thiourea and urea linkage into a thymol ring via an amino group results in higher activity than the parent compound thymol and a comparable pattern of results with the standard insect-growth regulators, Penfluron. Urea [Va-f] compounds exhibited greater effect on Total Haemocyte Count (THC) than thiourea [IVa-f]. Fluoro substitution enhanced the effect on THC more than chloro substituted compounds, while ortho-substitution resulted in a better effect than para-substitution. The results described in this paper are promising and provide new array of synthetic chemicals that may be utilized as insect growth regulators.

A versatile route for surface modification of carbon, metals and semi-conductors by diazonium salt-initiated photopolymerization

This paper describes a general procedure to graft vinylic polymers by surface-initiating photopolymerization (SIPP) on diazonium-modified substrates. We have selected three surface-grafted aryl initiating systems (aryl = benzoyl phenyl (BP), dodecylphenyl (DDP), aminophenyl (AP)). The substrates were gold, stainless steel, glassy carbon and ITO. As previously found, surface-BP in the presence of dimethyl aniline (DMA, co-initiator) is very efficient on all substrates as judged by XPS. The surface-DDP/benzophenone system is extremely interesting as it provides a new method for coating vinylic polymers onto aryl-modified substrates. In this system the grafted DDP groups act as hydrogen donors. The simple gold-AP initiating system is interesting and needs further developments. All surfaces were characterized by XPS and surface compositions were correlated with wettability measurements for the Au–BP-polymethacrylate series. PM-IRRAS permitted to monitor the growth of poly(methacrylic acid) with SIPP time. Finally, adhesion aspects are covered in a preliminary study. We show here that polymer grafts resist complete delamination by the powerful swelling solvent methyl ethyl ketone, particularly when they are crosslinked. This adhesion test has never been applied to polymers bonded to surfaces through aryl diazonium coupling agents.This work constitutes a new step in designing well defined polymer grafts using aryl diazonium-derived photoinitiators. The method could be adapted on demand to a variety of substrates.

(11-Methylpyrido[2,3-b][1,4]benzodiazepin-6-yl)(phenyl)methanone

In the title compound, C20H15N3O, the diazepine ring adopts a boat conformation. The dihedral angle between pyridine and benzene rings is 55.2 (1)°. The benzoyl phenyl ring forms dihedral angles of 49.4 (1) and 75.9 (1)°, respectively, with the pyridine and benzene rings. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of C—H⋯N hydrogen bonds.

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

In the title compound, C15H11NO2S, the dihedral angle between the aromatic rings is 80.35 (7)°. The heterocyclic six-membered ring is not planar: the puckering parameters of this ring are Q = 0.5308 (15) Å, θ = 63.11 (18) and ϕ = 23.5 (2)°. The mol­ecules are linked into inversion dimers with R 2 2(8) ring motifs by pairs of N—H⋯O hydrogen bonds. The dimers are inter­linked into polymeric sheets extending parallel to the bc plane by C—H⋯O hydrogen bonds, generating R 2 1(7) ring motifs. π–π inter­actions occur between the benzoyl phenyl rings with centroid–centroid separations of 3.9187 (15) Å.

Benzil bis(ketazine)

The title compound (systematic name: 1,1′,2,2′-tetra­phenyl-2,2′-azinodiethanone), C28H20N2O2, was obtained by the reaction of benzil monohydrazone with chromium(III) nitrate. The dibenzyl­idene hydrazine unit is nearly planar (r.m.s. deviation = 0.073 Å) and the two benzoyl units are oriented almost perpendicular to it [dihedral angle = 87.81 (2), 87.81 (2)°]. The mol­ecules are linked into chains along the c axis by C—H⋯O hydrogen bonds and the chains are cross-linked via C—H⋯π inter­actions involving the benzoyl phenyl rings.

2-Methyl-N-phenylbenzamide

In the structure of the title compound (NP2MBA), C14H13NO, the conformation of the C—O bond is syn to the ortho-methyl substituent in the benzoyl phenyl ring, while the N—H bond is anti to the ortho-methyl substituent. The structure of NP2MBA closely resembles that of 2-chloro-N-phenyl­benzamide, with similar bond parameters. The dihedral angle between the phenyl and benzoyl rings is 88.05 (5)°. Mol­ecules are linked into a chain through N—H⋯O hydrogen bonding.

2,5-Dibenzoylbenzene-1,4-diaminium dichloride

The asymmetric unit of the title compound, C20H18N2O2 2+·2Cl−, is composed of one-half of the 2,5-dibenzoyl­benzene-1,4-diaminium dication, located on a centre of inversion, and one Cl− ion. The dihedral angle between the central benzene ring and the benzoyl phenyl ring is 53.3 (2)°. In the crystal structure, ions are linked to form a two-dimensional network parallel to the (10) plane by N—H⋯Cl hydrogen bonds.

The Effect of Tri(n-butyl) Tin(IV) –2– [3–Benzoyl phenyl] Propionate on the Degradation and Stabilisation of PVC in Inert and Oxidative Atmospheres

Tri(n-butyl) tin(IV)–2–[3–benzoyl phenyl] propionate has been used to enhance the shelf life of rigid poly (vinyl chloride) (PVC). Studies of the thermal degradation of PVC have been a prime focus for a long time. Different substances have been tried to control and stabilise the process of thermal degradation. In the present work the aforementioned stabiliser has been used for this purpose. The samples of PVC containing different amounts of the stabiliser were prepared and treated at 190 ± 3 °C. The effect of the stabiliser on the degradation in nitrogen and air environments was studied through conductometric and spectroscopic measurements. The stabiliser was effective in slowing down the process of degradation. It also increased the initial induction period, i.e. the time during which no sign of degradation were observed. About 3% of stabiliser reduced the rate of the degradation of PVC by half, and almost doubled the induction period. It was more efficient in nitrogen than in air. These findings indicate that tri(n-butyl) tin(IV)–2–[3–benzoyl phenyl] propionate is a good inhibitor as well as an effective retarder.

Synthesis of Benzoyl Phenyl Benzoates as Effective Inhibitors for Phospholipase A2 and Hyaluronidase Enzymes.

Benzoylation of (hydroxy phenyl) phenyl methanone 2a-g to benzoyl phenyl benzoates 4a-g, a benzophenone analogue, was achieved in good yield. All the newly synthesized compounds were evaluated for their phospholipase A2 [E.C. 3.1.1.4] and hyaluronidase [E.C. 3.2.1.35] enzyme inhibitory activity in snake venom as source and their structure-activity relationship with respect to different groups is reported for the first time. The in vitro PLA2 enzyme inhibitory activity and in vivo anti-inflammatory activity studies of benzoyl phenyl benzoates are illustrated.

Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A 2 and hyaluronidase enzymes

Benzoylation of (hydroxy phenyl) phenyl methanone 2a– g to benzoyl phenyl benzoates 4a– g, a benzophenone analogue, was achieved in good yield. All the newly synthesized compounds were evaluated for their phospholipase A 2 [E.C. 3.1.1.4] and hyaluronidase [E.C. 3.2.1.35] enzyme inhibitory activity in snake venom as source and their structure–activity relationship with respect to different groups is reported for the first time. The in vitro PLA 2 enzyme inhibitory activity and in vivo anti-inflammatory activity studies of benzoyl phenyl benzoates are illustrated.

Synthesis of some newer analogues of substituted dibenzoyl phenol as potent anti-inflammatory agents

Benzoylation of hydroxybenzophenones 1a– f affords substituted benzoyl phenyl benzoates 3a– f, which on Fries rearrangement using microwave irradiation led to a facile synthesis of solely dibenzoyl phenols 4a– f in excellent yield. The newly synthesized compounds were screened for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compound 4e showed more potent activity than the standard drugs at all doses tested.