- Relationships between structure and molting hormonal activity of tebufenozide, methoxyfenozide, and their analogs in cultured integument system of Chilo suppressalis Walker
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The molting hormonal activity of methoxyfenozide (RH-2485), tebufenozide (RH-5992), five analogs with various alkyl groups, and 18 acyl analogs was measured by using cultured integument of rice stem borers, Chilo suppressalis Walker. The hormonal activity of methoxyfenozide was remarkably high (EC50 = 1.1 x 10-9 M), being equivalent to that of tebufenozide (RH-5992). The hormonal activity of several tebufenozide analogs with varying alkyl groups such as CH3, n-C3H7, i-C3H7, n-C4H9 and n-C5H11 at the para-position of the benzene ring furthest from the tert-butyl group was lower than that of tebufenozide (alkyl group is C2H5). The activity decreased to varying degrees as a result of replacement of the 3,5-dimethylphenyl moiety of tebufenozide with either a phenyl, naphthyl, or cyclohexyl group. Both 1- and 2-naphthyl derivatives were very active (EC50 = 4.3 x 10-8 M and 3.2 x 10-8 M, respectively) without any significant difference between them. The activity of the 1-cyclohexenyl analog (EC50 = 1.0 x 10-7 M) was about 40x that of the corresponding 3-cyclohexenyl analog (EC50 = 4.4 x 10-6 M), but 1/100 that of tebufenozide. The activity varied parabolically with respect to the molecular hydrophobicity, and decreased with longer acyl moieties. Copyright (C) 2000 Elsevier Science Inc.
- Nakagawa, Yoshiaki,Hattori, Kazunari,Minakuchi, Chieka,Kugimiya, Soichi,Ueno, Tamio
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- Preparation method of 6-chloro-2-methoxytoluene and synthesis process of methoxyfenozide
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The invention relates to the field of insecticides, in particular to a preparation method of 6-chloro-2-methoxytoluene and a synthesis process of methoxyfenozide. The preparation method of the 6-chloro-2-methoxytoluene comprises the following steps: in a solvent, mixing 2, 6-dichlorotoluene with sodium methoxide, and carrying out a substitution reaction to prepare a first reaction solution containing 3-chloro-2-sodium methylphenolate and the 6-chloro-2-methoxytoluene; and dropwise adding dimethyl sulfate into the first reaction solution, carrying out etherification reaction, removing 3-chloro-2-sodium methylphenolate to obtain a second reaction solution, and carrying out post-treatment to obtain the 6-chloro-2-methoxytoluene. The synthesis process of the methoxyfenozide comprises the following steps: preparing 3-methoxy-2-methyl benzoic acid by taking 6-chloro-2-methoxytoluene as an intermediate; using 3-methoxy-2-methyl benzoic acid and 3, 5-dimethyl benzoic acid as intermediates, and preparing to obtain the methoxyfenozide. According to the synthesis process disclosed by the invention, the yield and the purity of methoxyfenozide can be remarkably improved.
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- Green preparation process of 2-methyl-3-methoxybenzoyl chloride
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The invention discloses a green preparation process of 2-methyl-3-methoxybenzoyl chloride. The green preparation process comprises the following steps: heating and hydrolyzing methyl 2-methyl-3-methoxybenzoate in an alkaline aqueous solution, and distilling off generated methanol while a hydrolysis reaction is carried out; adding an organic solvent into hydrolyzed reaction liquid under the condition of heat preservation for dissolving, and adding an acidic aqueous solution for neutralizing; conducting neutralizing, then preserving heat and conducting layering to obtain a water layer and an organic layer, and washing the organic layer with water; heating the washed organic layer for azeotropic water removal; and adding a catalyst into the organic layer after azeotropic dehydration, carrying out heating, dropwise adding an acylating chlorination reagent, and carrying out a heat-preserved reaction to obtain the 2-methyl-3-methoxybenzoyl chloride. In a neutralization process after hydrolysis is completed, the organic solvent is added, and the product 2-methyl-3-methoxybenzoic acid is transferred into the organic solvent and is transferred to a subsequent reaction in a solution state, so water consumption for post-treatment is reduced, and meanwhile, harm to a working environment and the health of workers in the solid dust drying and feeding process is avoided.
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- Methoxyfenozide synthesis process
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The invention relates to a methoxyfenozide synthesis process, which comprises: 1) adding 3,5-dimethylbenzoic acid (toluene) into a reaction container, adding thionyl chloride in a dropwise manner, carrying out a heat insulation reaction for 2.5-3.5 h, and removing a solvent under reduced pressure to obtain an intermediate 3,5-dimethylbenzoyl chloride; 2) adding tert-butylhydrazine, an alkaline solution and toluene into a reaction container, cooling, adding di-tert-butyl dicarbonate, separating the water to remove the layer, adding the 3,5-dimethylbenzoyl chloride and an alkaline aqueous solution into the organic layer, adding hydrochloric acid into the reaction mixture, and carrying out a reaction for 18-25 h at a temperature of 30-40 DEG C to obtain N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine; and 3) adding the N-(3,5-dimethylbenzoyl)-N-tert-butylhydrazine and dichloroethane into the reaction container, adding a dichloroethane solution of 3-methoxy-2-methylbenzoyl chloride in a dropwise manner, slowly heating to a temperature of 18-25 DEG C, and filtering to obtain a filter cake so as to obtain the methoxyfenozide bulk drug. According to the invention, through the optimizing, the high-yield high-quality methoxyfenozide raw material is synthesized, and the synthesis ratio and the mild process conditions are obtained, so that the content and the synthesis yield of the methoxyfenozide bulk drug product are greatly improved; and the obtained methoxyfenozide has characteristics of high efficiency, low toxicity and environmental protection, can meet the insecticidal requirements of various types of pests, and has excellent market application prospect.
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Paragraph 0011-0013; 0016
(2020/01/12)
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- Preparation method of methoxyfenozide
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The invention discloses a preparation method of methoxyfenozide and relates to the field of insecticide, and particularly relates to the preparation method of methoxyfenozide. The preparation method includes steps of preparation of 3, 5-dimethylbenzoyl chloride: adding 3, 5-mesitylenic acid and methylbenzene in a reaction bottle; raising temperature to 60 DEG C, and dropwise adding thionyl chloride within 2 hours; preserving temperature for 3 hours, depressurizing and removing solvent to obtain 3, 5-dimethylbenzoyl chloride; synthesis of midbody: adding tert-butylhydrazine, sodium hydroxide and methylbenzene in the reaction bottle, and cooling to 0 DEG C; adding di-tert-butyl dicarbonate ester and reacting for 10 hours at 0-5 DEG C; removing a water layer, adding 3, 5-dimethylbenzoyl chloride and sodium hydroxide solution in an organic layer; reacting for 4 hours at 0-5 DEG C, filtering a product and adding the filter cake in methanol; adding hydrochloric acid in the reaction mixture;reacting for 20 hours at 35 DEG C; filtering the product, washing and drying to obtain the midbody. The preparation method is simple in operation, safe and reliable in reaction; the production efficiency is greatly improved, and the production cost is reduced; moreover, the product is high-efficient, low-toxic and environment-friendly.
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Paragraph 0010
(2018/07/30)
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- NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND
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An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.
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- Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
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The present invention relates to non-steroidal ligands for use in nuclear receptor-based inducible gene expression system, and a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene.
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Page/Page column 8
(2008/06/13)
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- Insecticidal N'-substituted-N,N'-diacylhydrazines
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Insecticidal compounds having the formula N-(2-Ra -3-Rb -4-Rh -benzoyl)-N'-(2-Rc -3-Rd -4-Re -5-Rf -benzoyl)-N'-Rg -hydrazine wherein Ra is a halo or lower alkyl; R b is lower alkoxy, optionally substituted with halo (preferably fluoro); Rc is selected from hydrogen, halo, lower alkyl, lower alkoxy, lower alkoxy lower alkyl, and nitro; Rd, Re and Rf are each independently selected from hydrogen, bromo, chloro, fluoro, lower alkyl, lower alkoxy, and lower alkoxy lower alkyl; Rg is a (C4 -C6)alkyl; Rh is hydrogen, lower alkoxy, lower alkyl, or when taken together with Rb is methylenedioxy (--OCH2 O--), 1,2-ethylenedioxy (--OCH2 CH2 O--), 1,2-ethyleneoxy (--CH2 CH2 O--) or 1,3-propyleneoxy (--CH2 CH2 CH2 O--) wherein an oxo atom is located at the Rb position; and the substituents Rc and Rd, or Rd and Re, or Re and Rf when taken together can be methylenedioxy or 1,2-ethylenedioxy as well as compositions comprising an agronomically acceptable carrier and an insecticidally effective amount of such compounds; and methods of using such compounds and compositions. Also, methods for the production of the compounds and their intermediates, which methods comprise either admixing a 3-amino-2-(substituted)-benzoic acid, sodium nitrite and methanol under acidic conditions or admixing a 3,4-fused heterocyclic benzoic acid and an alkyl lithium reagent followed by subsequent reaction with an electrophilic reagent.
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- Preparation of 1,2-diacyl-2-(t-alkyl)hydrazines
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The present invention provides a process for preparing 1,2-diacyl-2-(t-alkyl)hydrazines. More particularly, the present invention a process for preparing the aforesaid diacylhydrazines utilizing a solvent comprising an ester or a mixture of an ester and water in a process wherein an aromatic acid chloride is reacted in a first step with a t-alkylhydrazine or a corresponding acid addition salt of a t-alkylhydrazine such as the hydrochloride salt in the presence of a base to afford a 1-acyl-2-t-alkylhydrazine followed by a second step wherein an aromatic acid chloride is reacted with the aforesaid monoacylhydrazine in the presence of a base to afford the desired 1,2-diacyl-2-(t-alkyl)hydrazine. Such compounds are known to have excellent insecticidal activity against insects of the orders Lepidoptera and Coleoptera.
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