- A juvenile hormone analogs of the preparation method
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The invention relates to the field of insecticides, and particularly relates to a preparation method of a juvenile hormone analogue (which comprises S-methoprene and S-hydroprene). The preparation method of the juvenile hormone analogues comprises the following steps of: A. adding (2E, 4E)-11-R-3,7,11-trimethyl-2,4-dodecadienoic acid (R is hydrogen or methoxyl) serving as raw material, an organic alkali catalyst and an organic solvent to a reaction vessel, and starting stirring; B. dropwise adding an organic solvent (the same as the organic solvent in the step A) solution of pyrocarbonate; C. after the addition is completed, reacting at 0-30 DEG C for 0-3 hours; D. adding water to stop reaction, and splitting phases of reaction liquid to obtain an organic phase; E. carrying out reduced pressure concentration and distillation to obtain a product, wherein the steps can also be carried out under the condition that the addition sequences of the pyrocarbonate and an organic strongly-alkaline catalyst are exchanged. The preparation method disclosed by the invention has the advantages of mild reaction condition, high product purity, high yield, environment-friendly and safe route and good industrial prospect.
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Paragraph 0047; 0064-0065
(2017/05/10)
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- Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki-Miyaura cross-coupling
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A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key Csp2-Csp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved.
- Zhang, Shunji,Dong, Huaide,Gui, Jinghan,Tian, Weisheng
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p. 1882 - 1884
(2012/05/05)
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- Method for exterminating termites
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A method for exterminating termites comprising using an entomopathogenic nematode together with an inset-growth regulator or a slow-acting insecticide, wherein insecticidal effects are reinforced compared with the cases using singly the entomopathogenic nematode and the insect-growth regulator or the slow-acting insecticide, respectively, and a bait station for exterminating termites that contains an entomopathogenic nematode with an insect-growth regulator or a slow-acting insecticide. According to the invention, emission of harmful chemicals to environment can be suppressed. The invention is nonpoisonous for human being and livestock, and is useful for indoor or outdoor extermination of termites.
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- PROCESS AND MEANS FOR THE ERADICATION OF TICKS IN THE HABITATS OF SMALL MAMMALS
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Disclosed is a process for using a compound according to formula (I) or formula (II) to prepare a mixture for the eradication of ticks in the living quarters of small mammals, especially cats and dogs. Said process consists in applying as needed to the animal or animals of the habitat concerned a topical formulation in sufficiently pesticidal quantities of a compound according to formula (I), or possibly formula (II), at monthly intervals.
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- Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs
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Process and composition, in particular for controlling fleas on small mammals, characterized in that the composition includes, on the one hand, at least one insecticide of 1-N-arylpyrazole type, in particular fipronil, and, on the other hand, at least one compound of IGR (insect growth regulator) type, in doses and proportions which are parasiticidally effective on fleas, in a fluid vehicle which is acceptable for the animal and convenient for local application to the skin, preferably localized over a small surface area.
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- Preparation of alkyl 3-methylalka-2,4-dienoates from γ,δ-unsaturated β-keto esters via the corresponding conjugated unsaturated 3-enol phosphates
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Methylation of α,β,γ,δ-unsaturated-β-substituted enol phosphates with lithium dimethyl cuprate gave a mixture of (2E,4E)- and (2Z,4E) alkyl 3- methylalka-2,4-dienoates and unsubstituted alkyl alka-2,4-dienoates. An improved synthesis is described for ethyl β-safranate and the insect growth regulator hydroprene.
- Moorhoff, Cornelis M.,Schneider, David F.
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p. 3279 - 3290
(2007/10/03)
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- Combined Biochemical and Electrochemical Approach to Chiral C10-Components for Juvenoid Synthesis, and Preparation of (2E,4E,7S)Stereoisomers of Metoprene and Hydroprene
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Enantioselective acylation of (RS)-3,7-dimethyl-7-methoxyoctan-1-ol and (RS)-3,7-dimethyl-octan-1-ol with vinyl acetate in the presence of lipase from yeast Candida cylindracea was performed to conversion of 40-50%, and subsequent hydrolysis of the products afforded (S)-(-)-enantiomers of these alcohols with ee of 98-100%. The oxydation of these products by bromine generated by electrolysis in a membraneless device in the system "aqueous NaBr (+NaHCO3)/CH2Cl2" in the presence of 4-substituted 2,2,6,6-tetramethyl-1-oxopiperidinium salts furnished the corresponding (S)-(-)-alkanals. The condensation of the latter with the esters of 3-alkoxycarbonyl-2-methylprop-2-enylphosphonic acids in a heterophase system solid KOH-benzene-tetraoctylammonium bromide yielded samples of metoprene and hydroprene of high configurational purity.
- Gamalevich,Zhdankina,Kryshtal',Nikishin,Ogibin,Serebryakov
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p. 467 - 474
(2007/10/03)
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- Synthesis of S-(+)-hydroprene
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A novel path to S-(+)-hydroprene (1) starting from the technical grade S-(+)-dihydromyrcene (2, e.e. > 50percent) is proposed.The latter was selectively transformed into S-3,7-dimethyloctanal (5) in three steps including hydroalumination.The reactions of 5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl2/CuCl or by ozonolysis, afford S,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in ca. 23percent overall yield.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Kharisov, R. Ya.,Serebryakov, E. P.,Tolstikov, G. A.
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p. 100 - 101
(2007/10/02)
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- Terpenes in organic synthesis 14. Synthesis of S-(+)-hydroprene from (+)-β-citronellene
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A seven-step synthesis of S-(+)-hydroprene (S-1) in ca. 20percent overall yield starting from S-(+)-3,7-dimethyl-1,6-octadiene (2) of 55 +/- 10percent optical purity is described.The introduction of an optical enhancement step in the synthetic sequence at the stage of S-(-)-3,7-dimethyl-1-octanol (9) raises the optical purity of S-1 from ca. 50percent to ca. 80percent.
- Gamalevich, G. D.,Serebryakov, E. P.
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p. 300 - 306
(2007/10/02)
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- On the stereochemistry of the Horner-Emmons reaction between 3-functionally substituted 2-methyl-2-propenylphosphonates and aliphatic aldehydes 7. Quaternary ammonium phase transfer catalysts in a stereoselective synthesis of esters of 3-methyl-2E,4E-alkadienoic acids
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The reaction of diethyl 3-ethoxycarbonyl-2-methyl-2-propenylphosphonate (1a) with 3-methylbutanal (2) in heterogeneous MOH (solid)-behzene systems in the presence of 5-10 mol.percent of benzyltriethylammonium chloride (BTEAC) gives the reaction product (3) with a higher, for M = K, or lower, for M = Li, ratio of 2E,4E- and 2Z,4E-stereoisomers than that observed in the absence of BTEAC.Tetrabutylammonium bromide (TBAB) as a catalyst of the reaction 1a + 2 -> 3 in the system KOH (solid) - wet benzene leads to a higher : ratio than BTEAC; this ratio grows from 44:56 without TBAB to 80:20 at 100 mol.percent of TBAB.In the latter case...
- Kryshtal', G. V.,Zhdankina, G. M.,Serebryakov, E. P.
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p. 1048 - 1052
(2007/10/02)
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- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XXXVI. SYNTHESIS OF ETHYL 3,7,10-TRIMETHYL-2E,4E-DODECADIENOATE
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Hydroprene was obtained with an overall yield of 16percent in the form of a 77:23 mixture of 2E,4E and 2Z,4E isomers by ozonolysis of 1,5-dimethyl-1-cyclooctene and selective transformations of the 4-methyl-1,1-dimethoxy-8-oxononane, including ethoxycarbonylmethylenation of the keto group, alkylation of the formyl group by isopropylmagnesium bromide followed by deoxygenation, and allylic bromination-dehydrobromination.The individual 2E,4E isomer was isolated by HPLC.
- Odinokov, V. N.,Kukovinets, O. S.,Zainullin, R. A.,Sultanmuratova, V. R.,Tolstikov, G. A.
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p. 1230 - 1237
(2007/10/02)
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- SYNTHESIS OF ALKENOIC ACID DERIVATIVES CONTAINING CYCLOPROPANE RING, NEW JUVENILE HORMONE ANALOGS
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A synthetic method is described for the preparation of new type juvenoids .
- Baan, Gabor,Vinczer, Peter,Novak, Lajos,Szantay, Csaba
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p. 4261 - 4264
(2007/10/02)
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- Stereocontrolled Synthesis of the Insect Growth Regulators - Alkyl (2E,4E)-Dodecadienoates
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The title compounds 1 and 16 were synthesized by condensation of the dianions of β-keto esters 5 and 11 with aldehydes 4, and lithium dialkylcuprate addition to the enol acetate or enol phosphate of unsaturated β-keto esters 8 and 15.The (2E,4E)-dodecadienoate derivatives 1 and 16 were formed in a stereoselective manner.
- Novak, Lajos,Rohaly, Janos,Kolonits, Pal,Fekete, Jenoe,Varjas, Laszlo,Szantay, Csaba
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p. 1173 - 1182
(2007/10/02)
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- Aliphatic hydrocarbon 2,4-dienoic acids, esters and derivatives thereof
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Novel aliphatic hydrocarbon di-olefinic acids, esters, thiolesters, and derivatives thereof, intermediates therefor, syntheses thereof and the control of insects.
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