866639-19-2Relevant academic research and scientific papers
Method for preparing 3-iodine-N-(1, 1-dimethyl-2-methylthioethyl) phthalamic acid through microchannel reaction
-
Paragraph 0018; 0029-0034, (2019/04/17)
The invention relates to the field of organic synthesis, in particular to a method for preparing 3-iodine-N-(1, 1-dimethyl-2-methylthioethyl) phthalamic acid by utilizing microchannel reaction. The method includes following steps: respectively using a low-boiling-point organic solvent to dissolve 1.1-dimethyl-methylethylamine and 3-iodophthalic anhydride to obtain feed liquid A and B; using a mechanical pump to pump the feed liquid A and the feed liquid B into a micro mixer for mixing; allowing the feed liquid after being mixed well in the mixer to enter a microchannel reactor for reaction; after reaction is completed, receiving reaction liquid coming out of the microchannel reactor, and depressurize-compressing to obtain the product. The method has the advantages that the microchannel reactor is adopted for synthesis, so that reaction selectivity can be improved effectively, reaction time is reduced, and isomer generation can be reduced effectively; polar and nonpolar low-boiling-point solvents can be selected as a reaction solvent, so that recycling of the solvent is facilitated, and reaction cost is reduced.
Synthetic method of fipronil bisamide
-
Paragraph 0036; 0037, (2019/04/06)
The invention belongs to the technical field of synthesis of fipronil bisamide and discloses a synthetic method of fipronil bisamide. The synthetic method comprises the following steps: (a) amidation:reacting by virtue of 3-iodo-N-(1,1-dimethyl-2-methylthioethyl)-o-carbamoylbenzoic acid and 2-methyl-4-heptafluoroisopropylaniline in a non-protonic solvent under the effect of an amidation catalyst,so as to obtain a fipronil bisamide intermediate; and (b) thioether oxidation reaction: reacting by virtue of the fipronil bisamide intermediate in the non-protonic solvent under the effect of a thioether oxidizing agent, so as to obtain fipronil bisamide. Compared with the prior art, the synthetic method has the advantages that the one-step reaction step is reduced, so that the production time is substantially shortened, and the energy consumption is substantially reduced; and expensive trifluoroacetic anhydride is replaced with cheap thionyl chloride, so that the cost is substantially lowered.
Preparation method of intermediate containing halogenated benzene ring side-chain flubendiamide structure
-
Paragraph 0034; 0037-0039-0041; 0044-0047; 0050-0053; 0056, (2019/01/08)
The invention discloses a preparation method of an intermediate containing a halogenated benzene ring side-chain flubendiamide structure, comprising the following steps: adding 3-iodophthalic acid, toluene and p-methylbenzene sulfonic acid to obtain a 3-iodophthalic anhydride solution; adding triethylamine, cooling, dropwise adding a DMAC solution of 2-methyl-1-methylthiopropylamine to obtain 3-iodine-N-(1,1-dimethyl-2-methylthioethyl)carbamoylbenzoic acid and an isomer solution thereof; adding a dilute sulfuric acid solution, heating, and stirring to obtain 3-iodine-N-(1,1-dimethyl-2-methylthioethyl)carbamoylbenzoic acid and an isomer thereof; and adding a hydrochloric acid solution and heating to 60-80 DEG C and then carrying out thermal insulation for 1-3h, completing the hydrolysis ofthe isomer, cooling to 0-20 DEG C, and carrying out suction filtration to obtain the finished product 3-iodine-N-(1,1-dimethyl-2-methylthioethyl) carbamoylbenzoic acid. By the preparation method of the intermediate containing the halogenated benzene ring side-chain flubendiamide structure, generation of the isomer is reduced and the pollution caused by high consumption of organic solvents is alsoavoided.
Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel
Chen, Youwei,Li, Yuxin,Pan, Li,Liu, Jingbo,Wan, Yingying,Chen, Wei,Xiong, Lixia,Yang, Na,Song, Haibin,Li, Zhengming
, p. 6366 - 6379 (2015/01/09)
In order to find novel and environmental friendly insecticides targeting the ryanodine receptor, three series of novel phthalamides containing heptafluoroisopropyl group, low fluorine atoms group and non-fluorine group were designed and synthesized. 35 novel structures of three series were obtained. Insecticidal activities of title compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of title compounds showed moderate to high activities at the tested concentration. The structure-activity relationship (SAR) was discussed in detail. During synthesizing title compounds B8, C7, D1, D9 and D12, their corresponding positional isomers (B8′, C7′, D1′, D9′ and D12′) were afforded, and their structures were confirmed by 2D NMR. The calcium-imaging technique was also applied to investigate the effects of compounds B2, B10, C4 and C5 on the intracellular calcium ion concentration ([Ca2+]i), which indicated that they released stored calcium ions from endoplasmic reticulum, which denoted that some compounds are potential modulators of the insect ryanodine receptor (RyR).
Novel diamide insecticides: Sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives
Gnamm, Christian,Jeanguenat, Andre,Dutton, Ana C.,Grimm, Christoph,Kloer, Daniel P.,Crossthwaite, Andrew J.
scheme or table, p. 3800 - 3806 (2012/07/17)
Novel insecticidal anthranilamides with elaborated sulfur-containing groups are described. The synthesis of compounds with functional groups such as sulfoximines and scarcely reported groups such as sulfonimidoyl hydrazides and hydroxylamides, their in vitro and in vivo biological activity as well as their physical properties are reported.
Synthesis, insecticidal activity, and structure-activity relationship of trifluoromethyl-containing phthalic acid diamide structures
Feng, Mei-Li,Li, Yu-Feng,Zhu, Hong-Jun,Zhao, Liang,Xi, Bin-Bin,Ni, Jue-Ping
experimental part, p. 10999 - 11006 (2011/06/21)
Phthalic acid diamides have received considerable interest in agricultural chemistry due to a novel action mode, extremely high activity against a broad spectrum of lepidopterous insects, low acute toxicity to mammals, and environmentally benign characteristics. A series of phthalic acid diamides (4I-4IV) with the CF3 group at meta position on the aniline ring were synthesized. Their structures were characterized by 1H NMR and 13C NMR (or elemental analysis). The structure of N 2-[1,1-dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[3-fluoro- 5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide (4If) was determined by X-ray diffraction crystallography. Their insecticidal activities against Plutella xylostella were evaluated. The results show that some of the title compounds exhibit excellent larvicidal activities against P. xylostella, and improvement in larvicidal activity requires a reasonable combination of substituents in the parent structure, which provides some hints for further investigation on structure modification.
