- DIPHENYLPHOSPHINODITHIOIC ACID: A REAGENT FOR THE CONVERSION OF NITRILES TO THIOAMIDES
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Diphenylphosphinodithioic acid is a reagent useful for a sequence effecting the hydrolysis of nitriles under mild conditions.
- Benner, Steven A.
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- The Loss of ortho Halogeno Substituents From Substituted Thiobenzamide Ions
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The loss of ortho substituents (CH3, Cl, Br, I) from molecular ions of substituted thiobenzamides has been investigated by determination of the critical energy and kinetic energy released during this process to obtain some further insight into the corresponding reaction of N,N-dimethylthiobenzamide ions.In contrast to the latter compounds the ortho methyl substituent is not eliminated from the molecular ions of o-methylthiobenzamide, but the loss of ortho halogeno substituents occurs with identical reaction characteristics in both series of compounds.It is concluded that the loss of halogeno substituents from molecular ions in both series corresponds to a direct substitution reaction via a 4-membered transition state.
- Gruetzmacher, Hans-Fr.
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- A new method for converting nitriles into primary thioamides by sodium trimethylsilanethiolate
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A new method was developed for converting nitriles into primary thioamides. Treatment of various nitriles 1 with 1.5-2.5 equivalents of sodium trimethylsilyl sulfide (sodium trimethylsilanethiolate) in 1,3-dimethyl-2-imidazolidinone at 20-35°C for 4-30 hours gave the corresponding thioamides 2 in 27-80% yield.
- Lin,Ku,Shiao
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- TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
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The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.
- Noei, Jalil,Khosropour, Ahmad R.
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- Crystal landscape of primary aromatic thioamides
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The crystal landscape of a series of primary aromatic thioamides is described, displaying similar characteristic intermolecular hydrogen-bonding interactions in the solid state to those observed in their widely studied amide analogues, including R22(8) dimers and C(4) chains. In a number of cases, high Z′ values were observed in the structures. On the basis of the observed solid-state features, the thioamide functional group, which is a strong hydrogen-bond donor and moderate acceptor, offers considerable potential as a key moiety for crystal engineering.
- Eccles, Kevin S.,Morrison, Robin E.,Maguire, Anita R.,Lawrence, Simon E.
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- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
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- Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile
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The invention discloses a method for synthesizing a thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile. The method comprises the following steps: taking the substituted benzonitrile as a raw material, an inorganic sulfide as a sulfur source and CO2 as an auxiliary agent for reacting in the presence of a reaction solvent, and concentrating and purifying a reaction solution to obtain the thiobenzamide derivative. The reaction system disclosed by the invention is relatively simple, other catalysts are not added outside a reactant and the inorganic sulfide, themethod is suitable for synthesis of high-additional-value thiobenzamide containing a plurality of substituent groups, the reaction is carried out at low temperature and low pressure, and the risk coefficient is reduced.
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Paragraph 0037; 0038; 0040; 0041; 0042; 0049; 0050
(2019/01/24)
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- Mo (CO)6-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones
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In this paper, a novel catalyst is introduced based on the immobilization of palladium on modified magnetic graphene oxide nanoparticles. The catalyst is characterized by several methods, including transmission electron microscopy, scanning electron microscopy, X-ray fluorescence, vibrating-sample magnetometer, Fourier transform-infrared and dynamic light scattering (DLS) analysis. The activity of the catalyst was investigated in the synthesis of 4(3H)-quinazolinones via Pd-catalyzed carbonylation-cyclization of N-(2-bromoaryl) benzimidamides by Mo (CO)6. The Mo (CO)6 is used as a carbon monoxide source for performing the reaction under mild conditions. The catalyst showed good reusability, and no change in activity was observed after 10?cycles of recovery.
- Bahadorikhalili, Saeed,Ansari, Samira,Hamedifar, Haleh,Ma'mani, Leila,Babaei, Mohsen,Eqra, Rahim,Mahdavi, Mohammad
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- Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
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Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
- Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
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p. 170 - 181
(2018/03/08)
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- Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes
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The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.
- Li, Zheng,Qiu, Qianqian,Xu, Xue,Wang, Xuekun,Jiao, Lei,Su, Xin,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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supporting information
p. 246 - 257
(2016/03/08)
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- Synthesis, Activity, and Docking Study of Novel Phenylthiazole-Carboxamido Acid Derivatives as FFA2 Agonists
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Free fatty acid receptor 2 (FFA2), also known as GPR43, is activated by short-chain fatty acids (SCFAs) that are mainly produced by the gut microbiota through the fermentation of undigested carbohydrates and dietary fibers. FFA2 currently appears to be a
- Ma, Liang,Wang, Taijin,Shi, Min,Fu, Ping,Pei, Heying,Ye, Haoyu
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- Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs
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A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans), and mold (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity, except compounds 13 and 14 exhibited anti-human immunodeficiency virus-1 activity with EC50 values of 1.79 and 2.39 μM with Selectivity index = 18 and 4, respectively. On the other hand, compounds 7a and 7j showed a marked cytotoxicity against the human CD4+ lymphocytes (MT-4). Therefore, 7a and 7j were evaluated for their antiproliferative activity against two solid tumor-derived cell lines, which exhibited IC50 values of 8.1 ± 0.10 μM and 4.8 ± 0.08 μM against Hep-G2 cell lines, respectively.
- Khan, Mahmood-ul-Hassan,Hameed, Shahid,Akhtar, Tashfeen,Al-Masoudi, Najim A.,Al-Masoudi, Wasfi A.,Jones, Peter G.,Pannecouque, Christophe
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p. 2399 - 2409
(2016/10/25)
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- Design and optimization of hybrid of 2,4-diaminopyrimidine and arylthiazole scaffold as anticancer cell proliferation and migration agents
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Therapeutics of metastatic or triple-negative breast cancer are still challenging in clinical. Herein we demonstrated the design and optimization of a series of hybrid of 2,4-diaminopyrimidine and arylthiazole derivatives for their anti-proliferative properties against two breast cancer cell lines (MCF-7 as human breast cancer and MDA-MB-231 as triple-negative breast cancer). More importantly, some of those compounds with potent antiproliferative activities also indicated excellent inhibitory activities against MDA-MB-231 cell migration. These results suggested that the new series of hybridation of aryl-thiazoles and aminopyrimidines could be identified and developed as novel highly potential anticancer agents against the triple-negative breast cancer as well as metastatic one in the future.
- Zhou, Wenbo,Huang, Anling,Zhang, Yong,Lin, Qingxiang,Guo, Weikai,You, Zihua,Yi, Zhengfang,Liu, Mingyao,Chen, Yihua
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p. 269 - 280
(2015/04/27)
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- Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
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One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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p. 408 - 416
(2014/01/06)
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- Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines
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We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.
- Louvel, Julien,Guo, Dong,Agliardi, Marta,Mocking, Tamara A. M.,Kars, Roland,Pham, Tan Phát,Xia, Lizi,De Vries, Henk,Brussee, Johannes,Heitman, Laura H.,Ijzerman, Adriaan P.
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supporting information
p. 3213 - 3222
(2014/05/20)
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- 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
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Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guérin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 μg/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 μM, indicating its better safety profile.
- Yang, Jianzhong,Pi, Weiyi,Xiong, Li,Ang, Wei,Yang, Tao,He, Jun,Liu, Yuanyuan,Chang, Ying,Ye, Weiwei,Wang, Zhenling,Luo, Youfu,Wei, Yuquan
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p. 1424 - 1427
(2013/03/14)
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- Single-step microwave-mediated synthesis of oxazoles and thiazoles from 3-oxetanone: A synthetic and computational study
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The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further elaboration. Electronic structure calculations have shown that the order of events involves chalcogen atom attack at sp3 carbon and alkyl-oxygen cleavage. The critical role of acid catalysis was shown clearly, and the importance of acid strength was demonstrated. The calculated barriers were also fully consistent with the observed order of thioamide and amide reactivity. Spontaneous ring opening involves a modest degree of C-O cleavage, moderating the extent of strain relief. On the acid-catalysed pathway, C-O cleavage is less extensive still, but proton transfer to the nucleofuge is well advanced with the carboxylic acid catalysts, and essentially complete with methanesulfonic acid. Open sesame: The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of oxazoles and thiazoles. The reactions use a sustainable solvent, require only short reaction times and represent a highly competitive method for the construction of two classes of valuable heteroarenes. Electronic structure calculations have been used to probe a range of potential reaction mechanisms (see figure). Copyright
- Orr, David,Tolfrey, Alexandra,Percy, Jonathan M.,Frieman, Joanna,Harrison, Zo? A.,Campbell-Crawford, Matthew,Patel, Vipulkumar K.
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supporting information
p. 9655 - 9662
(2013/07/26)
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- A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
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A novel and efficient process for the synthesis of 3,5-diaryl-1,2,4- thiadiazoles from aryl nitriles in 1-butyl-3-methylimidazolium bromide promoted by (NH4)2S and TCT-DMSO is described.
- Noei, Jalil,Khosropour, Ahmad Reza
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supporting information
p. 9 - 11
(2013/02/21)
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- Ammonium phosphorodithioate: A mild, easily handled, efficient, and air-stable reagent for the conversion of amides into thioamides
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A simple, efficient, and new method has been developed for the synthesis of thioamides from amides. As described below, the reaction of a variety of aromatic and aliphatic amides in the presence of ammonium phosphorodithioate as an efficient reagent proceeded effectively to afford the corresponding thioamides in high yields. This method is easy, rapid, and high-yielding for the synthesis of thioamides from amides using an easily handled reagent. Georg Thieme Verlag Stuttgart · New York.
- Kaboudin, Babak,Malekzadeh, Leila
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experimental part
p. 2807 - 2810
(2012/01/02)
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- Solvent-free synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by grinding of thioamides under oxidative conditions
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An efficient and facile synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by oxidative dimerisation of thioamides by grinding with NBS under solvent-free conditions at room temperature has been developed. The efficiency of this reaction was demonstrated by the compatibility with trifluoromethyl, methyl, methoxy, chloro, pyridyl and thienyl groups. This method has notable advantages in terms of short reaction times, high yields and is a more practical alternative to the existing methods to access these compounds.
- Xu, Yali,Chen, Jiuxi,Gao, Wenxia,Jin, Huile,Ding, Jinchang,Wu, Huayue
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experimental part
p. 151 - 153
(2010/08/06)
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- Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid
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A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.
- Khosropour,Noei,Mirjafari
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experimental part
p. 752 - 758
(2010/11/04)
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- Synthesis and in-vitro cytotoxicity of poly-functionalized 4-(2-arylthiazol-4-yl)-4H-chromenes
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A new series of 4-aryl-4H-chromenes bearing a 2-arylthiazol-4-yl moiety at the 4-position were prepared as potential cytotoxic agents. The in-vitro cytotoxic activity of the synthesized 4-aryl-4H-chromenes was investigated in comparison with etoposide, a well-known anticancer drug, using MTT colorimetric assay. Among them, the 2-(2-chlorophenyl)thiazol-4-yl analog 4b showed the most potent activity against nasopharyngeal epidermoid carcinoma KB, medulloblastoma DAOY, and astrocytoma 1321N1, and compound 4d bearing a 2-(4-chlorophenyl) thiazol-4-yl moiety at the 4-position of the chromene ring exhibited the best inhibitory activity against breast cancer cells MCF-7, lung cancer cells A549, and colon adenocarcinoma cells SW480 with IC50 values less than 5 μM. The ability of compound 4b to induce apoptosis was confirmed in a nuclear morphological assay by DAPI staining in the KB and MCF-7 cells.
- Mahmoodi, Majid,Aliabadi, Alireza,Emami, Saeed,Safavi, Maliheh,Rajabalian, Saeed,Mohagheghi, Mohammad-Ali,Khoshzaban, Ahad,Samzadeh-Kermani, Alireza,Lamei, Navid,Shafiee, Abbas,Foroumadi, Alireza
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experimental part
p. 411 - 416
(2011/08/05)
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- Substituted 1,3-thiazole compounds, their production and use
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(1) A 1,3-thiazole compound of which the 5-position is substituted with a 4-pyridyl group having a substituent including no aromatic group or (2) a 1,3-thiazole compound of which the 5-position is substituted with a pyridyl group having at the position adjacent to a nitrogen atom of the pyridyl group a substituent including no aromatic group has an excellent p38 MAP kinase inhibitory activity.
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- Reactions of some ortho and para halogenated aromatic nitriles with ethylenediamine: Selective synthesis of imidazolines
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The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (SNAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA to thiobenzamide derivatives. The difference in reactivity between the nitrile and thioamide derivatives was estimated by a frontier orbital approach at the RHF/6-31G** level which predicted a greater reactivity of substituted thiobenzamides towards the nucleophilic addition of EDA.
- Crane, Louis J.,Anastassiadou, Maria,Stigliani, Jean-Luc,Baziard-Mouysset, Geneviève,Payard, Marc
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p. 5325 - 5330
(2007/10/03)
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- SUBSTITUTED THIAZOLE DERIVATIVES BEARING 3-PYRIDYL GROUPS, PROCESS FOR PREPARING THE SAME AND USE THEREOF
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The present invention provides a pharmaceutical composition having a steroid C17,20-lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism, tumor such as breast cancer and the like, more particularly, a steroid C17,20-lyase inhibitor containing a compound represented by the formula: wherein A1 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, one of A2 and A3 is a hydrogen atom, a halogen atom, a C1-4 aliphatic hydrocarbon group optionally having substituents or an optionally esterified carboxyl group, the other of A2 and A3 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, and at least one of A1, A2 and A3 is a 3-pyridyl group optionally having substituents, or a salt thereof or a prodrug thereof.
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Page/Page column 40
(2008/06/13)
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- Design and synthesis of sulfonyl-substituted 4,5-diarylthiazoles as selective cyclooxygenase-2 inhibitors
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A series of novel sulfone substituted 4,5-diarylthiazoles have been synthesized and evaluated for their inhibition of the two isoforms of human cyclooxygenase (COX-1 and COX-2). This series displays exceptionally selective COX-2 inhibition.
- Carter, Jeffery S.,Rogier,Graneto, Matthew J.,Seibert, Karen,Koboldt, Carol M.,Zhang, Yan,Talley, John J.
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p. 1167 - 1170
(2007/10/03)
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- THE REACTION OF NITRILES WITH O,O-DIALKYL-DITHIOPHOSPHORIC ACIDS
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Nitriles react with dialkyldithiophosphoric acids 2a-c to give a mixture of corresponding thioamides and O,O-dialkyl-N-thioacetyl-phosphoroamidothioates 3a-e.The structure of compounds 3 are elucidated chemically and from electronic spectra.The yield of thioamides are improved from the reaction of nitriles with compound 2b in presence of water.Mechanistic consideration on the formation of the products are discussed.
- Yousif, N. M.
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p. 4599 - 4604
(2007/10/02)
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- STUDIES ON ORGANOPHOSPHORUS COMPOUNDS PART 55 THE TRANSFORMATION OF NITRILES TO THIOAMIDES WITH O,O-DIALKYLDITHIOPHOSPHORIC ACID
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The reaction between nitriles and O,O-dialkyldithiophosphoric acid (2) under anhydrous conditions produces O,O-diethyl-N-thiobenzoylamidophosphate (5), contrary to literature.When water is present the same reaction gives the corresponding thioamides in reasonable to good yields.Mechanistic considerations and spectral data are presented for the products.
- Shabana, R.,Meyer, H.J.,Lawesson, S.-O.
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p. 297 - 306
(2007/10/02)
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- Effects of varying solvents and of the addition of sulfur on the rate of thiohydrolysis of aromatic nitriles
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Maximal rates of formation of thioamides from m- and p-substituted benzonitriles were obtained by bubbling H2S through solutions of the nitrile in pyridine containing a 0.11 mol fraction of triethylamine or in 95percent ethanol containing about 0.22 mol fraction triethylamine; at other mol fractions the rate fell off sharply.The Hammett p value of +2.3 in pyridine indicates that HS- is the reactive species.The addition of enough sulfur to saturate the solution leads to about a 3-fold enhancement of rate, probably because of the formation of polysulfide ions in trace amounts.
- Abbas, Khamis,Edward, John T.
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p. 3075 - 3078
(2007/10/02)
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- Pesticidal 1,2,4-triazole compounds
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The compounds of the formula: STR1 wherein R1 represents phenyl substituted in at least the 2-position by fluorine, chlorine, bromine or iodine, R2 represents a group R3, --OR3, --SR3 or --NR3 R4 where R3 represents hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 6 carbon atoms, cycloalkenyl of 3 to 7 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 10 carbon atoms or naphthyl, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy or alkylthio groups of 1 to 6 carbon atoms, nitro groups, cyano groups or mercapto groups, R4 represents a group as defined for R3 but not necessarily identical thereto, and A and B, together with the carbon atoms to which they are attached, form a 3,6-disubstituted pyridazine, a 3,6-disubstituted dihydropyridazine, a 2,5-disubstituted pyrimidine, a 1,2,4-oxadiazole, a 1,2,4-oxadiazoline or a 1,2,4-triazole ring, and the quaternary salts thereof, are novel compounds which are pesticidal, notably with respect to acarids, insects and aphids and their eggs and larvae. Compositions containing the compounds are also described as well as processes for their preparation and methods of using them.
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