- Preparation method of trobiglide
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The present invention discloses a method of preparation of trilobiril, specifically related to the field of agricultural technology, the preparation method provided by the present invention comprises the following steps: step 1, p-chlorobenzonitrile disso
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Paragraph 0024-0025
(2022/01/12)
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- Evaluation of the molluscicidal activities of arylpyrrole on Oncomelania hupensis, the intermediate host of Schistosoma japonicum
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The snail Oncomelania hupensis is the only intermediate host of the highly invasive parasite Schistosoma japonicum. Molluscicide is often used to curb transmission of S. japonicum. Niclosamide, the only World Health Organization (WHO) recognized molluscicide, presents major drawbacks, including high cost and toxicity towards aquatic animals. In the present study, a number of aryl pyrrole derivatives (ADs) were synthesized to serve as potential molluscicides and were tested on O. hupensis. To uncover the underlying mechanisms, adenosine triphosphate (ATP) and adenosine diphosphate (ADP) levels were assessed in the soft body of ADs-exposed O. hupensis, using high performance liquid chromatography (HPLC). The effect of C6 on key points of energy metabolism (the activities of complexes I, III, IV and the membrane potential) was determined. We demonstrated that the Compound 6 (C6, 4-bromo-1-(bromomethyl)-2-(4-chlorophenyl)-5- (trifluoromethyl)-1H-pyrrole-3-carbonitrile) exerted the strongest molluscicidal activity against adult O. hupensis at LC50 of 0.27, 0.19, and 0.13 mg/L for 24, 48, and 72 h respectively. Moreover, we found that the bromide on the pyrrole ring of C6 was essential for molluscicidal activity. Furthermore, the ATP content reduced from 194.46 to 139.75 mg/g after exposure to 1/2 LC50, and reduced to 93.06 mg/g after exposure to LC50. ADP, on the other hand, remained the same level before and after C6 exposure. We found that C6, at 1/2 LC50, reduced the membrane potential of O. hupensis, while no significant changes were observed in the activities of complexes I, III, and IV. C6 was identified with excellent activities on O. hupensis. The obtained structure-activity relationship and action mechanism study results should be useful for further compound design and development.
- Dai, Jianrong,Feng, Bainian,Qu, Guoli,Xing, Yuntian,Yao, Jiakai
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- Method for producing chlorfenapyr intermediate pyrrole by replacing acetonitrile with solvent DMF
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The invention provides a method for producing chlorfenapyr intermediate pyrrole by replacing acetonitrile with a solvent DMF. The solvent DMF is used for replacing acetonitrile. The method for producing the chlorfenapyr intermediate pyrrole by replacing a
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Paragraph 0005; 0025-0058
(2021/04/07)
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- Application of 2-aryl substituted pyrrole compound in medicine for killing oncomelania hupensis
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The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing oncomelania hupensis and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component,is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the oncomelania hupensis. Immersion killing use amount of the 2-aryl substituted pyrrole compound being the active component of the snail killing agent is 0.1-10.00 mg/l, and immersion killing time is 24-72 h. The use amount of spray application is 1-10 g/m and action timeis 3-7 days. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the oncomelania hupensis and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.
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Paragraph 0085; 0087; 0090; 0091; 0157
(2019/01/08)
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- Application of 2-aryl substituted pyrrole compound in medicine for killing biomphalarid snails
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The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing biomphalarid snails and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component, is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the biomphalarid snail. Immersion killing use amount of the 2-aryl substitutedpyrrole compound being the active component of the snail killing agent is 0.5-10.00 mg/l, and immersion killing time is 24-72 h. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the biomphalarid snails and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.
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Paragraph 0093; 0095; 0098; 0099; 0164
(2019/01/08)
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- PRODUCTION OF ARYLPYRROL COMPOUNDS IN THE PRESENCE OF DIPEA BASE
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The invention relates to a process for the production of compounds of formula (I), comprising Step A of reacting compounds of formula (II) with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. It also relates to a process for the production of compounds of formula (III), comprising Step B of reacting compounds of formula (I) with Br2 in the presence of DIPEA. It also relates to a process C for the production of compounds of formula (IV), comprising Step C of reacting compounds of formula (III) with di(C1-C4-alkoxy)methane and either POCl3, or a mixture comprising POCl3 and DMF, in the presence of DIPEA. It also relates to the use of DIPEA as a base in the production of compounds of formula (I), compounds of formula (III) or compounds of formula (IV).
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Page/Page column 14
(2018/10/19)
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- Synthesis, insecticidal and acaricidal activities of novel 2-arylpyrroles
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To search for novel 2-arylpyrroles with unique biological activities, a series of novel 2-arylpyrrole derivatives were designed and synthesized, and their structures were characterized by 1H and 13C NMR spectroscopy, MS spectrometry, and elemental analysis. Their insecticidal activities against Lepidopteran pests (e.g. Mythimna separata) and acaricidal activities against mites (e.g. Tetranychus urticae) were evaluated. The results of bioassays indicate that some of these title compounds exhibited excellent insecticidal and acaricidal activities. For example, 4-bromo-1-((chloromethoxy) methyl)-2-(4-chloro phenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (6a), 4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)-methyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (6d) showed insecticidal activity against Mythimna separata and 4-bromo-2-(4-chlorophenyl)-1-((isopropoxymethoxy)methyl)-5- (trifluoro methyl)pyrrole-3-carbonitrile (7d) showed acaricidal activity against Tetranychus urticae. They were more effective than Chlorfenapyr, which has been the only commercialized member of a new class of chemicals of 2-arylpyrroles.
- Liu, Aiping,Tang, Ming,Yu, Shuying,Liu, Xingping,Wang, Xiaoguang,Pei, Hui,Wu, Daoxin,Hu, Li,Ou, Xiaoming,Huang, Mingzhi
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p. 117 - 123
(2013/03/14)
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- Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds
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There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and
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- Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds
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There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds of formula I from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control
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- Process for the manufacture of 2-aryl-5-perfluoroalkylpyrrole derivatives and intermediates useful therefor
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There is provided a single step procedure to prepare 2-aryl-5-perfluoroalkylpyrrole derivatives directly from the perfluoroacetylated Strecker reaction product. Said pyrrole derivatives are insecticidal and also useful as precursors to other insecticidal arylpyrrole compounds. Further provided are amide nitrile intermediates, useful in the preparation of insecticidal arylpyrrole compounds.
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- Process for the manufacture of 2-aryl-5 perfluoroalkylpyrrole derivatives
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There is provided a single step procedure to prepare 2-aryl-5-perfluoroalkylpyrrole derivatives directly from the perfluoroacetylated Strecker reaction product. Said pyrrole derivatives are insecticidal and also useful as precursors to other insecticidal arylpyrrole compounds. Further provided are amide nitrile intermediates, useful in the preparation of insecticidal arylpyrrole compounds.
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- A simple synthesis of 3-substituted 5-trifluoromethylpyrroles via modified Hantzsch reaction
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5-Trifluoromethyl-substituted pyrroles have been prepared in high yields via the Hantzsch reaction.
- Kameswaran, Venkataraman,Jiang, Biao
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p. 530 - 532
(2007/10/03)
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- Oxazole amines as intermediates in the manufacture of insecticidal pyrroles
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The present invention provides 5-amino-4-aryl-2-perfluoroalkyl-1,3-oxazole derivatives, a method for the preparation of said derivatives and their use as a key intermediate in the manufacture of insecticidal, acaricidal and nematocidal arylpyrrole compoun
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- Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates
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The present invention provides a process for the manufacture of 2-aryl-5-(perfluoroalkyl)pyrrole-3-carbonitrile comprising the cycloaddition of 5-amino-4-aryl-2-perfluoroalkyl-1,3-oxazole and the appropriate 1,3-dipolarifile. The arylpyrrole-3-carbonitril
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- The Synthesis of Pyrroles with Insecticidal Activity
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The 2-aryl-4-bromo-5-trifluoromethylpyrrole-3-carbonitriles represent a new class of insect control agents. The high insecticidal activity observed in this series prompted us to investigate the preparation of regioisomeric arylhalotrifluoromethylpyrrole c
- Kuhn, David G.,Kamhi, Victor M.,Furch, Joseph A.,Diehl, Robert E.,Lowen, Gregory T.,Kameswaran, Venkataraman
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p. 279 - 286
(2007/10/03)
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- Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds
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There is provided a process for the preparation of 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds which are useful as insecticidal, acaricidal and nematicidal agents.
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- Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds from N-(substituted benzyl)-2,2,2-trifluoro-acetimidoyl chloride compounds
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There is provided a process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds via the condensation of an N-(substituted benzyl)-2,2,2-trifluoroacetimidoyl chloride compound with an α-
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- Synthesis of 2-aryl-5-(trifluoromethyl)pyrroles useful as pesticidal agents and as intermediates for the preparation of said agents
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There is provided a synthesis of 2-aryl-5-(trifluoromethyl)pyrrole compounds via the condensation of a suitable enamine with an α-haloketone.
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- Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
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This invention is directed to certain novel insecticidal, acaricidal and nematicidal arylpyrrole agents and a method for controlling insects, acarids and nematodes therewith. The invention also is directed to a method for protecting growing plants from insect, acarid and nematode attack by applying to said plants or the soil in which they are growing, an insecticidally, acaricidally or nematicidally effective amount of a novel arylpyrrole compound. The present invention further is directed to a method for the preparation of the arylpyrrole compounds.
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- Method of controlling phytopathogenic fungi
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This invention is directed to a method for the control of phytopathogenic fungi by contacting the same with a cyano- or nitroarylpyrrole compound, or by applying said pyrrole compound to the foliage of a plant susceptible to disease caused by said pathogens.
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- Method of and bait compositions for controlling mollusks
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This invention relates to methods of controlling mollusks with arylpyrrole compounds and to bait compositions containing a molluscicidally effective amount of an arylpyrrole compound.
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