- Design, synthesis and evaluation of novel trichloromethyl dichlorophenyl triazole derivatives as potential safener
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The dominance of safener can unite with herbicides acquiring the efficient protection of crop and qualifying control of weeds in agricultural fields. In order to solve the crop toxicity problem and exploit the novel potential safener for fenoxaprop-P-ethyl herbicide, a series of trichloromethyl dichlorobenzene triazole derivatives were designed and synthesized by the principle of active subunit combination. A total of 21 novel substituted trichloromethyl dichlorobenzene triazole compounds were synthesized by substituted aminophenol and amino alcohol derivatives as the starting materials, using cyclization and acylation. All the compounds were unambiguously characterized by IR,1H-NMR,13C-NMR, and HRMS. A greenhouse bioassay indicated that most of the title compounds could protect wheat from injury caused by fenoxaprop-P-ethyl at varying degrees, in which compound 5o exhibited excellent safener activity at a concentration of 10 μmol/L and was superior to the commercialized compound fenchlorazole. A structure–activity relationship for the novel compounds was determined, which demonstrated that those compounds containing benzoxazine groups showed better activity than that of oxazole-substituted compounds. Introducing a benzoxazine fragment and electron-donating group to specific positions could improve or maintain the safener activity for wheat against attack by the herbicide fenoxaprop-P-ethyl. A molecular docking model suggested that a potential mechanism between 5o and fenoxaprop-P-ethyl is associated with the detoxication of the herbicide. Results from the present work revealed that compound 5o exhibited good crop safener activities toward wheat and could be a promising candidate structure for further research on wheat protection.
- Guo, Ke-Liang,Zhao, Li-Xia,Wang, Zi-Wei,Rong, Shu-Zhe,Zhou, Xiao-Lin,Gao, Shuang,Fu, Ying,Ye, Fei
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- Design, synthesis and biological activity of novel sulfonylurea oxazolidines
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A series of N-[(p-methylphenyl)sulfonyl]-1,3-oxazolidine-3-carboxamide 4 was synthesized by cycloaddition and acylation reaction with alkamine, ketones, and p-methylbenzenesulfonyl isocyanate as the starting materials. The structures of all the compounds
- Fu, Ying,Kang, Jing-Xin,Wang, Yun-Kai,Liu, Jing,Zhao, Li-Xia,Gao, Shuang,Ye, Fei
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p. 740 - 750
(2016/05/09)
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- Synthesis, crystal structure and bioactivity of nphenoxyacetyl- 2-substituted-1,3-oxazolidines
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A series of novel N-phenoxyacetyl-1,3-oxazolidine derivatives were synthesized by the cyclization and acylation with ethanolamine, ketone and phenoxyacetyl chloride as the starting materials. The structures of all the compounds were characterized by IR,
- Ye, Fei,Li, Na,Zhao, Li-Xia,Gao, Shuang,Fu, Ying
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p. 127 - 131
(2019/01/18)
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- METHOD FOR PRODUCING ACETAL COMPOUND BY USING 4-METHYLTETRAHYDROPYRAN AS SOLVENT
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PROBLEM TO BE SOLVED: To provide a method for producing an acetal compound which is higher in safety and can be applied to a highly polar reaction raw material or the like. SOLUTION: There is provided a method for producing an acetal compound by reacting an alcohol compound, a thiol compound or an amine compound with a carbonyl compound in 4-methyltetrahydropyran. According to the production method of an acetal compound of the present invention, an acetal compound higher in safety can be produced under a mild reaction condition by using 4-methyltetrahydropyran having low toxicity and the method can be widely applied to a highly polar raw material. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0042
(2017/01/02)
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- Synthesis and biological evaluafion of some new alicyclicspiro-2′- (1′, 3′ -oxazolidine) derivatives
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Condensation of cyclic ketones 1 with ethanolamines gave the corresponding spiro-oxazolidines 2. The thioamides 3 were obtained in good yields through reaction of 2 with the appropriate isothiocyanate. Reaction of 2 with formaldehyde or acetaldehyde in the presence of the appropriate amine afforded the corresponding aminomethyl spiro-compounds 4 and 5 respectively, in excellent yields. The structures of the isolated compounds were fully determined by spectral methods. Antimicrobial activities of some oxazolidines were also discussed.
- Faidallah, Hassan M.,Sharshira,Al-Saadi, Mohammed S.M.
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experimental part
p. 43 - 50
(2010/03/01)
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- 3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 14. Pyrolysis of oxazolidinylmethylene derivatives of Meldrum's acid - Synthesis of N-alkenyl-3-hydroxypyrroles and related reactions
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Flash vacuum pyrolysis (FVP) of the title compounds 14 and 17 at 600-625°C (0.005 Torr) gives the N-alkenyl-pyrrolones 22 and 23 respectively. The mechanism is shown to involve hydrogen transfer and cyclisation of the methyleneketene intermediate (e.g. 25) to a fused pyrrolone (e.g. 28). This species fragments to create an azomethine ylide which provides the alkenyl substituent by a further hydrogen transfer. Similar reactions are shown by the thiazolidine derivatives 20 and 21, though in the latter case the initial bicycles 35 and 37 can be observed by NMR spectroscopy. When the normal sites for hydrogen transfer are blocked by substituents (as in compound 16) an alternative hydrogen transfer-cycloaddition sequence leads to the fused pyridin-4-one 43.
- Gaber, Abd El-Aal M.,Hunter, Gordon A.,McNab, Hamish
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p. 548 - 554
(2007/10/03)
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- Substituted N-(2-Hydroxyethyl)-1,3-thiazolidin-4-ones: Synthesis and anticorrosive properties
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A one-pot procedure was developed for synthesis of N-(2-hydroxyethyl)-1,3- thiazolidin-4-ones in 64-68% yield by reactions of monoethanolamine with carbonyl compounds and mercaptoacetic acid. The synthesized compounds were characterized by IR and 1H NMR spectra, and their anticorrosive properties were studied.
- Kukharev,Stankevich,Klimenko,Kovalyuk,Bayandin
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p. 665 - 666
(2007/10/03)
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- Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
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This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.
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Page column 86
(2010/02/05)
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- The concept of docking/protecting groups in biohydroxylation
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A general principle for biohydroxylation, in which time-consuming screening and enrichment techniques are avoided, is demonstrated by the introduction of a docking/protecting group into the substrate. This facilitates acceptance by the microorganism and allows the use of a narrow range of microorganisms, for example Beauveria bassiana ATTC7159 (B.b.), for the hydroxylation of compounds with diverse structures. After the biohydroxylation, the docking/protecting group is removed (see scheme).
- Braunegg, Gerhart,De Raadt, Anna,Feichtenhofer, Sabine,Griengl, Herfried,Kopper, Irene,Lehmann, Antje,Weber, Hans-Jorg
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p. 2763 - 2766
(2007/10/03)
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- Indirect monoalkylation of primary and secondary amines by reductive decyanation of α-aminonitriles with sodium cyanoborohydride-mercury bis(trifluoroacetate)
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Secondary and tertiary amines are prepared from α-aminonitriles by selective reductive cleavage of the cyanide moiety. The α-aminonitriles in this case, function as 'masked' imine or iminium ions and are 'unmasked' by mercury(II) in the presence of sodium cyanoborohydride to obtain the reduced product. Secondary amines may be prepared indirectly from primary amines in good yield without danger of over alkylation.
- Sassaman, Mark B.
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p. 10835 - 10840
(2007/10/03)
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- Antidoted herbicide compositions and antidote compositions
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Herbicidal compositions comprising a substituted thiolcarbamate derivative corresponding to the formula (I) wherein R1, R2 and R3 are selected independently from alkyl groups having 1 to 4 carbon atoms and/or a chloroacetanilide derivative corresponding to the formula (II) wherein R4 and R5 are hydrogen or alkyl group having 1 to 4 carbon atoms, identical or different, R6 is an alkoxyalkyl group corresponding to the formula --R7 --O--R8 in which R7 and R8 are selected from alkyl groups having 1 to 4 carbon atoms and, as an antidote, a thiocarbamic acid derivative corresponding to the formula (III) wherein R9 and R10 independently from each other are alkyl or alkenyl group having 1 to 4 carbon atoms, or R9 and R10 taken together with one or two nitrogen atoms form a heterocyclic group, which may contain one oxygen atom or they form a soiro-heterocyclic or condensated ring, which can be substituted with alkyl groups having 1 to 4 carbon atoms or an aryl group, R11 is an alkyl or alkenyl group having 1 to 3 carbon atoms or a benzyl group containing one or 2 substituents, carboxy methylene, 1-methylene naphtyl, acetophenon-(2)-yl-, carb-(α)naphthoxy-methylene, N-methylene o-benzoic acid sulphimide, N-isopropyl-N-phenylacetamidyl, N,N-disubstituted-2-acetamidyl group containing alkyl, alkylene groups having 1 to 3 carbon atoms, alkoxyalkyl, phenyl or dialkyl phenyl group.
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- Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride
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A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.
- Saavedra, Joseph E.
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p. 2271 - 2273
(2007/10/02)
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- Oxazolidine derivatives
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New products and methods for their preparation; principally, 3-(glycidyl)-1,3-oxazolidines and derivatives thereof obtained via the reaction of a 3-(glycidyl)-1,3-oxazolidine with an amine, alcohol, sulfonate, mercaptan, azide or cyanide. Also covered are oxazolidines containing a carboxy function which are obtained by treating a 3-(glycidyl)-1,3-oxazolidine with a mono-or poly-carboxylic acid. The products are useful in improving the adhesiveness of polymers and in promoting the room temperature cure of isocyanate and anhydride polymers to afford new plastic, adhesive and coating materials.
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