- A simple method for the preparation of 3,5-dinitrimino-1,2,4-triazole and its salts
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The reaction of 2-methyl-1-nitrоisothiourea with hydrazine in the presence of alkali metal bicarbonates (carbonates) resulted in the formation of 3,5-dinitrimino-1,2,4-triazole salts. The same salts were also formed by a reaction of 2-methyl-1-nitrоisothiourea with alkali metal salts of 4-nitrоsemicarbazide. This represents the first synthesis and characterization of the high-energy 3,5-dinitrimino-1,2,4- triazole, which can be readily isolated by treatment of its disodium salt with HCl.
- Astakhov, Alexander M.,Antishin, Denis V.,Revenko, Vitalii A.,Vasiliev, Alexander D.,Buka, Eduard S.
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- Structure and properties of 1-amino-2-nitroguanidinium nitrate
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A nitrogen-rich energetic material 1-amino-2-nitroguanidinium nitrate (ANGN) was synthesized and fully characterized by nuclear magnetic resonance, infrared spectroscopy, mass spectroscopy and elemental analysis. Its thermal behavior and detonation properties were also investigated to give a better understanding of its physical and chemical properties. The results show that the calculated critical temperature of thermal explosion, entropy of activation, enthalpy of activation, free energy of activation, detonation pressure and detonation velocity are 319.8 K, 130.24 J mol-1 K-1, 155.45 kJ mol-1, 106.45 kJ mol-1 43.0 GPa and 9775 m s-1, respectively. It is predicted that ANGN possesses excellent energetic properties compared to those of RDX and HMX, and can be considered as a potential energetic material.
- Jin, Xinghui,Hu, Bingcheng,Liu, Zuliang,Lv, Chunxu
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- Synthesis and insecticidal activities of 1,5-disubstituted-1,3,5- hexahydrotriazine-2-N-nitroimines
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By extracting active moieties from typical insecticides and recombining to a same molecule, a series of novel title compounds were designed and synthesized as shown in Scheme 1. The structures of all compounds were confirmed by IR, 1H NMR, MS, and elemental analysis. The preliminary bioassay showed that the partial target compounds gave 90% mortality against Tetranychus cinnabarnus at 500 mg/L.
- Xue, Si-Jia,Liu, Li,Bu, Hong-Fei,Xu, Yong-Hua
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- Transition metal complexes of 3-Amino-1-nitroguanidine as laser ignitible primary explosives: Structures and properties
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3-Amino-1-nitroguanidine (ANQ, 2) was synthesized via hydrazinolysis of nitroguanidine. By dissolving 2 in solutions containing transition metal salts, several complexes M2+(ANQ)2X2(H 2O)y with M2+ = Co, Ni, Cu, Zn as well as M(ANQ)2X(H2O)y with M = Ag could be isolated. In these cases, nitrate as well as perchlorate and chloride served as the respective anions X. Additionally, the ANQ complexes of Co, Ni, and Ag with dinitramide as the anion were synthesized from ANQ and silver dinitramide and by reacting the cobalt and nickel ANQ perchlorate complexes with ammonium dinitramide. The crystal structures of all described complexes were determined by low temperature single-crystal X-ray diffraction. Additionally, they were characterized using IR spectroscopy and elemental analysis. The decomposition temperatures were determined by differential scanning calorimetry and the sensitivities toward impact and friction were assessed using a BAM drophammer and a BAM friction tester (BAM = Bundesanstalt fuer Materialforschung und -pruefung). Additionally, the sensitivity toward electrostatic discharge was determined on a small-scale ESD device. The potential use of the nitrate, dinitramide and perchlorate containing species as primary explosives was investigated in a laser ignition test.
- Fischer, Niko,Joas, Manuel,Klapoetke, Thomas M.,Stierstorfer, Joerg
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- 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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- A containing 1, 2, 3 - thiadiazole [...] amino guanidine compound synthesis and use
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The invention provides nitro arylideneamino guanidine compounds containing 1, 2, 3-thiadiazole as well as a preparation method and application thereof. The invention relates to isothiazole oxime ether compounds, which have a chemical structural general formula shown as IV. The formula is shown in the specification. The invention discloses a structural general formula and a synthetic method of the compounds, application of the compounds serving as insecticides, bactericides, anti-virus substances for plants and plant activators, application of a combination of the compounds and agriculturally acceptable aids or synergists or a combination of the compounds and commercial insecticides, acaricides, bactericides, anti-virus substances for plants and plant activators in prevention and control of diseases, pests, acarids and viruses of agriculture, forestry and horticulture and a preparation method.
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Sheet 0034-0036
(2017/12/28)
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- Synthesis, insecticidal and fungicidal activities of methyl 2-(methoxyimino)-2-(2-((1-(N′-nitrocarbamimidoyl)-2-hydrocarbylidene-hydrazinyl)methyl)phenyl)acetates
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N′-Nitro-2-hydrocarbylidenehydrazinecarboximidamides and methoxyacrylates are two types of important agrochemicals. By combining their key fragments into one framework, a series of the title compounds was designed and synthesized. Some of these compounds have shown excellent insecticidal activities for aphides, for example, the LC50 values of compounds 6-06, 6-11 and 6-19 against M. perslcae and H. amygdale were found to be 1.9/14.4, 13.4/1.5 and 0.3/38.4 mg L-1 respectively. They were also effective against the mycelium growth of B. cinerea in vitro. Compound 6-04 could control (~100%) cucumber anthrax and rice blast at 100 mg L-1 in vivo, and inhibit the spore germination (~100%) of vegetable gray mold at 6.25 mg L-1. These compounds could be considered as potential insecticidal or fungicidal candidates for crop protection. The results of structure-activity relationship (SAR) studies are discussed.
- Yuan, Xiaoyong,Jia, Changqing,Ma, Yongqiang,Yang, Dongyan,Rui, Changhui,Qin, Zhaohai
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p. 19916 - 19922
(2016/03/04)
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- Method for synthesizing 1-amino-3-nitroguanidine
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The invention discloses a method for synthesizing 1-amino-3-nitroguanidine. The method comprises the following steps of adding 2-methyl-3-nitryl isothiourea to water, dropwise adding hydrazine hydrate with the concentration being 80%, after adding of the hydrazine hydrate is ended, raising the temperature to 40-70 DEG C, preserving the temperature for 3-6 hours, conducting cooling and filtration, and conducting elution and drying with water and ethyl alcohol, so that amino nitroguanidine is obtained, wherein the mole ratio of the hydrazine hydrate to the 2-methyl-3-nitryl isothiourea is 1: (1-2). The method is mainly applied to 1-amino-3-nitroguanidine synthesis.
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023; 0024
(2016/11/28)
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- Synthesis and properties of two energetic salts based on 1-amino-2-nitroguanidine
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Two nitrogen-rich energetic materials based on 1-amino-2-nitroguanidine were synthesized. The thermal behavior, thermodynamic properties, electron structures and detonation properties were investigated. The dynamic (DSC) curves show that 1-amino-2-nitroguanidinium 2,4,5-trinitroimidazole (salt 1) can be used as cast explosives. These curves allow determination of their melting points and thermodynamic parameters such as activation energy (Ek, salt 1, 282.1 kJ mol-1; salt 2, 116.2 kJ mol-1; Eo, salt 1, 275.0 kJ mol-1; salt 2, 116.9 kJ mol-1), entropy of activation (ΔS #, salt 1, 395.7 J mol-1 K-1 salt 2, 5.8 J mol-1 K-1), enthalpy of activation (ΔH #, salt 1, 278.7 kJ mol-1 ; salt 2, 113.1 kJ mol-1 ), free energy of activation (Δ G#, salt 1, 117.6 kJ mol-1 salt 2, 110.9 kJ mol-1), heat of formation (ΔHf-0 0, salt 1, 264.7 kJ mol-1 salt 2, 487.6 kJ mol-1) and critical temperature of thermal explosion (Tb, salt 1, 412.3 K; salt 2, 388.9 K), suggesting that the synthesized salts are safe enough during storage or usage. In view of the detonation pressure (P, salt 1, 30.2 GPa; salt 2, 29.1 GPa) and detonation velocity (D, salt 1, 8398 m s-1; salt 2, 8334 m s-1), it is predicted that both 1-amino-2-nitroguanidine-based salts have the potential to be the useful energetic materials.
- Jin, Xinghui,Hu, Bingcheng,Liu, Zuliang
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p. 124 - 130
(2015/02/19)
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- N ′-nitro-2-hydrocarbylidenehydrazinecarboximidamides: Design, synthesis, crystal structure, insecticidal activity, and structure-activity relationships
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A novel series of acyclic imine-substituted nitenpyram analogues were designed and synthesized from nitroaminoguanidine, and their structures were confirmed using X-ray diffraction crystallography. Preliminary bioassays showed that the target molecules exhibited good activities against aphids in laboratory (Myzus persicae Sulzer) and field trials (M. persicae Sulzer and Brevicoryne brassicae Linnaeus). Comparative molecular field analysis and comparative molecular similarity indices analysis were employed to develop a three-dimensional quantitative structure-activity relationship model that describes the insecticidal activity of 21 neonicotinoid derivatives. Simple synthesis, low cost, and good insecticidal activity have made this series of compounds become very promising candidates for future commercial pesticides.
- Su, Wangcang,Zhou, Yihui,Ma, Yongqiang,Wang, Lei,Zhang, Zheng,Rui, Changhui,Duan, Hongxia,Qin, Zhaohai
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scheme or table
p. 5028 - 5034
(2012/08/07)
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- HYDROCARBYLIDENE NITROHYDROZINECARBOXIMIDAMIDES AND A METHOD FOR MAKING THE SAME, AS WELL AS THEIR USES AS AN INSECTICIDE
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The present invention discloses hydrocarbylidene nitrohydrozinecarboximidamides and the use thereof as well as a method for making the same. The structural general formula of the compounds are shown in formula I, wherein, R1 is C1-C10 saturated and/or unsaturated aliphatic hydrocarbonyl, benzyl, substituted benzyl, halogenated picolyl, halogenated thiazolyl methyl, tetrahydrofuryl methyl or oxazolyl methyl; R2 is hydrogen, C1-C5 saturated and/or unsaturated aliphatic hydrocarbonyl, phenyl, substituted phenyl, pyridyl or substituted pyridyl; R3 is hydrogen, C1-C10 saturated and/or unsaturated aliphatic hydrocarbonyl, furyl, phenyl, substituted phenyl, benzyl or substituted benzyl. The tests of insecticidal activity show that the hydrocarbylidene nitrohydrozinecarboximidamides shown by formula (I) have high preventive efficiency against insect pests of plants, such as aphid, plant hopper, cotton bollworm, asparagus caterpillar, and the like, and can be used as plant insecticides.
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Page/Page column 3-4
(2012/01/03)
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- CONDENSED AMINO NITROGUANIDINE COMPOUNDS, SYNTHESIS AND USE AS BOTANICAL INSECTICIDES THEREOF
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The present invention discloses hydrocarbylidene nitrohydrozinecarboximidamides and the use thereof as well as a method for making the same. The structural general formula of the compounds are shown in formula I, wherein, R1 is C1 - C10 saturated and/or unsaturated aliphatic hydrocarbonyl, benzyl, substituted benzyl, halogenated picolyl, halogenated thiazolyl methyl, tetrahydrofuryl methyl or oxazolyl methyl; R2 is hydrogen, C1 - C5 saturated and/or unsaturated aliphatic hydrocarbonyl, phenyl, substituted phenyl, pyridyl or substituted pyridyl; R3 is hydrogen, C1 - C10 saturated and/or unsaturated aliphatic hydrocarbonyl, furyl, phenyl, substituted phenyl, benzyl or substituted benzyl. The tests of insecticidal activity show that the hydrocarbylidene nitrohydrozinecarboximidamides shown by formula (I) have high preventive efficiency against insect pests of plants, such as aphid, plant hopper, cotton bollworm, asparagus caterpillar, and the like, and can be used as plant insecticides.
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Page/Page column 5-6
(2010/08/18)
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- NOVEL IMIDAZOLE DERIVATIVES, PREPARATION AND USER THEREOF AS MEDICINE
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The invention concerns novel imidazole derivatives of general formula (I), wherein Z′ and Z represent different variable groups. Said products have an antitumoral activity. The invention also concerns pharmaceutical compositions containing said products and their use for preparing antitumoral medicine.
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Page/Page column 8
(2009/07/25)
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- Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine
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The synthesis of the useful reagent for the preparation of guanidines, 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine (DMNPC), has been optimised. A detailed protocol for using this reagent for the preparation in pure form of a range of guanidines via nitroguanidines is described. A comparison has been made regarding efficiency between DMNPC and the guanidinylating reagents N,N′-bis-Boc-1-pyrazole-1-carboxamidine (2) and N,N′-bis-Boc- N′-triflylguanidine (3).
- Castillo-Melendez, Joel A.,Golding, Bernard T.
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p. 1655 - 1663
(2007/10/03)
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- Synthesis and Some Properties of 1,2-Dinitroguanidine
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1,2-Dinitroguanidine is a product of nitroguanidine nitration with nitric acid and its mixtures with sulfuric acid and oleum. It is a diacid (pK a 1.11, ~11.5) and at the same time a weak base undergoing protonation at the nitrogen of the amino group (pKBH+ -5.81). The decomposition kinetics of 1,2-dinitroguanidine was studied by spectrophotometric method both in acid and alkaline media, and the mechanism of the process was assumed. In the media of high acidity (Ho > -8) the 1,2-dinitroguanidine suffers reversible denitration into nitroguanidine. At lower acidity its conjugate acid or molecular form undergoes hydrolysis yielding nitrourea. Monoanion of 1,2-dinitroguanidine in a weak acid or in an alkali is hydrolyzed into N,N′-dinitrourea. The reaction of 1,2-dinitroguanidine with alkali in alcohol provides its salts, with nitrogen-containing bases form both salts and derivatives of 2-nitroguanidine. The treatment of 1,2-dinitroguanidine with haloalkanes results in its N-alkylated products.
- Astrat'yev,Dashko,Kuznetsov
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p. 501 - 512
(2007/10/03)
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- Protecting-group strategies for the synthesis of N4-substituted, and N1,N8-disubstituted spermidines, exemplified by hirudonine
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Methods are described for the preparation of derivatives of the polyamines 1,4-diaminobutane (putrescine), and N′-(3-amihopropyl)-l,4-diaminobutane (spermidine) in which a particular amino group is modified with, e.g., a guanidino function. Specific amino groups in these polyamines were protected as ;V-trifluoroacetyl, and yV-4-azidobenzyloxycarbonyl derivatives, which were unmasked chemoselectively using methanolic ammonia, and dithiothreitol-triethylamine, respectively. Guanidino functions were introduced by an improved procedure in which an amino group was treated with 3,5-dimethyl-Ar-nitro-!//-pyrazole-l-carboximidamide in methanol to give a nitroguanidine derivative, from which the nitro group was removed by catalytic transfer hydrogenation. The methodology is exemplified by the development of efficient preparative routes to agmatine, and hirudonine. The integrity of the sequence of protection/deprotection leading to hirudonine was confirmed by a crystal-structure analysis of its sulfate. The effect of selected compounds on the uptake of putrescine into rat lung cells was determined, and showed that N4-(4-azidobenzyloxycarbonyl)spermidine was the best inhibitor (Ki = 3.4 μM).
- Golding, Bernard T.,Mitchinson, Andrew,Clegg, William,Eisegood, Mark R. J.,Griffin, Roger J.
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p. 349 - 356
(2007/10/03)
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- SUBSTITUTED 2-NITROGUANIDINES IN REACTION WITH HYDRAZINE HYDRATE
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The reaction of substituted 2-nitroguanidines with hydrazine hydrate was investigated.It was shown that 1-alkyl-2-nitroguanidines and 1-methyl-1-nitroso-2-nitroguanidine form 1-amino-2-nitroguanidine, while 1-aryl(aroyl)-2-nitroguanidines form 1-aryl(aroyl)-3-amino-2-nitroguanidines.
- Metelkina, E. L.,Novikova, T. A.
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p. 1989 - 1991
(2007/10/02)
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