cas 18063-03-1, 2,6-Difluorobenzamide | Articles data

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SYNTHESIS OF VARIOUS AROMATIC AMIDE DERIVATIVES USING NITRILE HYDRATASE OF RHODOCOCCUS RHODOCHOROUS J1
Nitrile hydratase, that is produced abundantly in cells of Rhodococcus rhodochorous J1, catalyses the conversion of various aromatic nitrile derivatives to the corresponding amides.Using Rh. rhodochorous J1 resting cells, the conditions for the production of benzamide, 2,6-difluorobenzamide, indolacetamide, thiophenecarboxamide and furanecarboxamide were optimized.Under the determined conditions, 489 g of benzamide, 306 g of 2,6-difluorobenzamide, 1045 g of 3-indoleacetamide, 210 g of 2-thiophenecarboxamide and 522 g of 2-furanecarboxamide were produced, with 100percent molar conversion, from the corresponding nitriles, per litre of reaction mixture.
Mauger, Jacques,Nagasawa, Toru,Yamada, Hideaki
p. 1347 - 1354
(1989)
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Preparation method of 2,6-difluorobenzamide
The invention provides a preparation method of 2,6-difluorobenzamide with hydrogen fluoride as a reaction raw material, wherein the method improves the atom utilization rate of the reaction, can produce a byproduct acid, effectively reduces the production cost of the product, and improves the market competitiveness of the product; besides, the whole process does not generate mixed waste salt, and the process flow is simple.
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Paragraph 0074; 0080-0081; 0082-0085; 0086-0090; 0091-0094

(2021/05/29)

Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron
The invention discloses a synthesis method of an insecticide teflubenzuron and an intermediate 2,6-difluorobenzamide of the insecticide teflubenzuron, belonging to the field of pesticides. The synthesis method comprises the following steps: step 1, preparation of 2,6-dichlorobenzylidene chloride: preparing turbid liquid of dichlorotoluene and phosphorus pentachloride, introducing chlorine gas, layering materials by utilizing a gas-liquid separator, collecting a crude product, and rectifying the crude product to obtain the 2,6-dichlorobenzylidene chloride; and 2, preparation of 2,6-dichlorobenzonitrile: mixing 2,6-dichlorobenzylidene chloride, acetic acid, zinc chloride, hydroxylamine hydrochloride and sodium acetate, carrying out heating for a reflux reaction, conducting cooling, stirring,filtering and drying successively after the reaction is completed so as to obtain 2, 6-dichlorobenzonitrile. By adopting a one-pot method, a reaction route is shortened, total yield is increased to 67.3% from conventional 55.4%, and cost is greatly reduced.
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(2020/12/10)

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons
A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.
Dang, Mingming,Liu, Minhua,Huang, Lu,Ou, Xiaoming,Long, Chuyun,Liu, Xingping,Ren, Yeguo,Zhang, Ping,Huang, Mingzhi,Liu, Aiping
p. 4088 - 4098
(2020/10/02)

Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides
A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.
Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath
p. 724 - 728
(2020/01/23)

Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane-Water
The catalytic nitrile hydration (amide formation) in a copper iodide/cesium carbonate/1,8-diazabicyclo[5.4.0]undec-7-ene/nitromethane-water system is described. The protocol is robust and reliable; it can be applied to a broad range of substrates with high chemoselectivity.
Kuwabara, Jun,Sawada, Yoshiharu,Yoshimatsu, Mitsuhiro
supporting information
p. 2061 - 2065
(2018/09/14)

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
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
p. 170 - 181
(2018/03/08)

Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives
A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.
Song, Gaopeng,Li, Jianzuo,Tian, Hao,Li, Yasheng,Hu, Dekun,Li, Ying,Cui, Zining
p. 329 - 334
(2016/04/04)

Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun
p. 2544 - 2546
(2016/07/07)

Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety
A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.
He, Haifeng,Wang, Xiaoyan,Shi, Liqiao,Yin, Wenyan,Yang, Ziwen,He, Hongwu,Liang, Ying
p. 3263 - 3270
(2016/07/12)

Design, synthesis and biological evaluation of novel 5-fluoro-1H-benzimidazole-4-carboxamide derivatives as potent PARP-1 inhibitors
A series of novel 5-fluorine-benzimidazole-4-carboxamide analogs were designed and synthesized. All target compounds were evaluated for their PARP-1 inhibitory activity. Compounds possessed high intrinsic PARP-1 inhibitory potency have been evaluated in v
Wang, Junwei,Wang, Xuyan,Li, Hui,Ji, Dezhong,Li, Yuyan,Xu, Yungen,Zhu, Qihua
p. 4127 - 4132
(2016/08/01)

Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2- furanmethyl ester
Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.
Ying,Bao-Ju,Ling,Miao, Hong-Jian,Yan-Xia,Yang, Xin-Ling
p. 3037 - 3042
(2011/07/31)

Biotransformation of nitriles using the solvent-tolerant nitrile hydratase from Rhodopseudomonas palustris CGA009
A study has been carried out into the biocatalytic hydration of nitriles using the nitrile hydratase enzyme from Rhodopseudomonas palustris CGA009. It has been shown that this nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. The major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates.
Black, Gary W.,Gregson, Thomas,McPake, Christopher B.,Perry, Justin J.,Zhang, Meng
experimental part
p. 1639 - 1641
(2010/05/19)

Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives
In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.
Cui, Zining,Ling, Yun,Li, Baoju,Li, Yongqiang,Rui, Changhui,Cui, Jingrong,Shi, Yanxia,Yang, Xinling
scheme or table
p. 4267 - 4282
(2010/10/03)

Discovering potent small molecule inhibitors of cyclophilin A using de novo drug design approach
This work describes an integrated approach of de novo drug design, chemical synthesis, and bioassay for quick identification of a series of novel small molecule cyclophilin A (CypA) inhibitors (1-3). The activities of the two most potent CypA inhibitors (3h and 3i) are 2.59 and 1.52 nM, respectively, which are about 16 and 27 times more potent than that of cyclosporin A. This study clearly demonstrates the power of our de novo drug design strategy and the related program LigBuilder 2.0 in drug discovery.
Ni, Shuaishuai,Yuan, Yaxia,Huang, Jin,Mao, Xiaona,Lv, Maosheng,Zhu, Jin,Shen, Xu,Pei, Jianfeng,Lai, Luhua,Jiang, Hualiang,Li, Jian
supporting information; experimental part
p. 5295 - 5298
(2010/02/28)

A novel class of potent influenza virus inhibitors: Polysubstituted acylthiourea and its fused heterocycle derivatives
A series of polysubstituted and fused heterocycle derivatives of acylthiourea was prepared and the biological activity against influenza virus was evaluated. Of the analogues that demonstrated IC50s 0.1 μM, acylthiourea derivatives 16 and 50 were further investigated as candidates with the most potential for future development. The SAR of these compounds are discussed and they represent a novel class of highly potent and selective inhibitors of influenza virus.
Sun, Chuanwen,Huang, Hai,Feng, Meiqing,Shi, Xunlong,Zhang, Xiaodong,Zhou, Pei
p. 162 - 166
(2007/10/03)

Selective and efficient heterogeneous hydration of nitriles to amides using silica supported manganese dioxide
A highly efficient and selective method for hydration of nitriles to amides without formation of any detectable amount of acid, under heterogeneous reaction condition using silica supported manganese dioxide is reported. The mechanism of the reaction has been discussed. The reagent preparation is easy and carried out under microwave exposure within 5 min. The silica supported MnO2 reagent has been characterized by DRIFT and XRD techniques. Quantitative yields are obtained for commercially important heterocyclic amides such as pyridinecarboxamide, nicotinamide and pyrazinamide.
Khadilkar, Bhushan M.,Madyar, Virendra R.
p. 2814 - 2819
(2007/10/03)

Ozonolysis of Alkenes and Studies of the Reactions of Polyfunctional Compounds. LVIII. Ozonolysis of 2,6-Difluoro-β,β-Dimethylstyrene as an Effective Way to 2,6-Difluorobenzamide and Synthesis of New Analogs of Difluorobenzurone
Ozonolysis of 2,6-difluoro-β,β-dimethylstyrene, formed by isomerization of the product of alkylation of sodium derivative of m-difluorobenzene with methallyl chloride, yields 2,6-difluorobenzamide, transformation of which to 2,6-difluorobenzoyl isocyanate and the reaction of the latter with corresponding arylamines leads to new effective analogs of difluorobenzurone.
Odinokov,Ishmuratov,Kukovinets,Harisov,Lozhkina,Mustafin,Abdrahmanov,Tolstikov
p. 202 - 204
(2007/10/03)

An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ270
A variety of aliphatic, aromatic and heterocyclic nitriles have been readily hydrolysed into the corresponding amides and/or acids under very mild conditions using Rhodococcus sp. AJ270. The nitrile hydratase involved in this novel nitrile-hydrolysing microorganism efficiently hydrates most nitriles tested, irrespective of the electronic and steric effects of the substituents, to form the amides. Conversion of amides into acids catalysed by the associated amidase is rapid and efficient in most cases. Substrates bearing an adjacent substituent (which may be an ortho substituent on an aromatic nitrile, an adjacent heteroatom in a heterocyclic ring or a geminal substituent in an α,β-unsaturated nitrile) undergo slow hydrolysis of the amides allowing efficient amide isolation. The scope, limitations and reaction mechanism of this enzymatic process have been systematically studied. A molecular size of >7 A diameter and the presence of functions capable of metal complexation near to the nitrile inhibit hydrolysis.
Meth-Cohn, Otto,Wang, Mei-Xiang
p. 1099 - 1104
(2007/10/03)

A Powerful New Nitrile Hydratase For Organic Synthesis-Aromatic And Heteroaromatic Nitrile Hydrolyses- A Rationalisation
A powerful new nitrile hydratase organism, Rhodococcus rhodocrous AJ270 has been isolated that efficiently hydrolyses all kinds of nitriles to amides and/or acids.This paper shows that aromatic and heterocyclic nitriles are readily hydrolysed to acids but, that those bearing an adjacent-substituent (which may be an ortho substituent or an adjacent heteroatom in the ring) give amides in good yield but only slowly proceed to acids.
Meth-Cohn, Otto,Wang, Mei-Xiang
p. 9561 - 9564
(2007/10/02)

A new homogeneous platinum containing catalyst for the hydrolysis of nitriles
[(Me2PO···H···OPMe2)PtH(PMe2OH) is an extremely active homogeneous catalyst for the hydration of nitriles to amides: a mechanism involving intramolecular attack by a phosphine oxide on a nitrile within the co-ordination sphere of the platinum atom is suggested.
Ghaffar, Talk,Parkinsa, Adrian W.
p. 8657 - 8660
(2007/10/02)

INSECT CHITIN FORMATION INHIBITORS. PART IV. SYNTHESIS OF NOVEL 3-SUBSTITUTED 1-(2,6-DIHALOGENOBENZOYL)-UREA DERIVATIVES
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Balicki, Roman,Sobotka, Wieslaw,Ejmocki, Zdzislaw
p. 1049 - 1053
(2007/10/02)

Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds
Novel substituted N-pyrrolylphenyl-N'-benzoylurea compounds of the formula STR1 in which X and Y independently of one another are each hydrogen or halogen, R is hydrogen or halogen, and Z is hydrogen, halogen or methyl. The compounds have valuable propert
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(2008/06/13)

Method of making N-[4-chlorophenyl)amino]carbonyl)-2,6-difluorobenzamide
In accordance with the sought-after features of an improved process for the preparation of Dimilin, there is provided herein a process which comprises first extracting 2,6-difluorobenzamide from an aqueous acid solution with a selective solvent which is acid-stable and water-insoluble. The extract then is condensed in situ with p-chlorophenyl isocyanate at an elevated temperature to form the desired product. The selective solvent preferably has a boiling point at the reaction temperature, preferably about 120°-170° C. Finally, the product is crystallized from the selective solvent.
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(2008/06/13)