- Sex pheromone of Lonomia obliqua: Daily rhythm of production, identification, and synthesis
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The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5- to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0- to 1-day-old) females. The sex pheromone gland of 1- to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic- electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)- and (Z)-11-hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.
- Zarbin, Paulo H. G.,Lorini, Lisete M.,Ambrogi, Bianca G.,Vidal, Diogo M.,Lima, Eraldo R.
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- INSECT PHEROMONES AND THEIR ANALOGUES XXVI. SYNTHESIS OF HEXADEC-11Z-EN-1-OL AND ITS ACETATE AND HEXADEC-11Z-EN-AL -COMPONENTS OF THE PHEROMONES OF INSECTS OF THE ORDER LEPIDOPTERA
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Pheromone components of insects of the genera Heliothis and Mamestra have been synthesized with the use of functionally differentiated ozonolysis of cyclododecene.
- Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Tolstikov, G. A.
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- Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes
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This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.
- Le, Van-Dung,Le, T. Cam-Huong,Chau, Van-Trung,Le, T. Ngoc-Duyen,Dang, Chi-Hien,Vo, T. To-Nguyen,Nguyen, Trinh Duy,Nguyen, Thanh-Danh
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p. 4746 - 4755
(2021/03/22)
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- Method for synthesizing grassland spodoptera litura sex pheromone active ingredients
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The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.
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- A moth pheromone pickles preparation method (by machine translation)
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The invention discloses a method for preparing a moth pheromone pickles, characterized in that comprises the following steps: S1, taking eleven vinyl alcohol synthesis undecene - 11 - ol benzoates; S2, will take Hendecane glycol synthesis Hendecane mono benzoates; S3, synthetic undecanal - 11 - ol benzoates; S4, synthetic cis - 11 - hexadecenoic - 1 - ol benzoates; S5, synthetic cis - 11 - hexadecenoic - 1 - ol; S6, synthetic cis - 11 - sixteen [...]; S7, synthetic cis - 11 - hexadecenoic - 1 - ethoxylate ester; S8, the composition is mixed, moth pheromone shall pickles. The present invention, adopts a double-sodamide as alkali, phosphine ye li? deodorant pentane as raw material with undecanal - 11 - alcohol benzoate reaction occurs, the reaction yield is as high as 89%, and syn-form isomer content of 98% or more, and the synthetic method is simple. (by machine translation)
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- A moth pheromone synthesis method of pickles (by machine translation)
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The invention belongs to the technical field of chemical synthesis, in particular relates to a moth pheromone of the pickles synthetic method, comprises the following steps: 1) in the organic solvent, 11 - bromo - 1 - [...] with triphenylphosphine reaction to produce bromo Hendecane [...]; 2) under the protection of nitrogen, step 1) obtained in the bromo Hendecane [...] with valeraldehyde, sodium ethoxide in tetrahydrofuran solvent to react to generate cis - 11 - sixteen-carbon vinyl alcohol; 3) in the dichloromethane solution in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with the occurrence chloro-chromic acid pyridine salt to the oxidizing reaction to produce cis - 11 - sixteen [...]; 4) in dichloromethane in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with acetic anhydride, pyridine reaction to produce cis - 11 - sixteen-carbon vinyl alcohol acetate. The invention uses inexpensive and easily obtained 11 - bromo - 1 - [...] as the starting material, the synthesis step is reduced, simplifies the synthesis process, the product yield is high, the reaction conditions are mild and controllable, low requirements on equipment, can be used for industrial production. (by machine translation)
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- SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
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Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
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- SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
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The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.
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Paragraph 0187; 0188
(2013/09/12)
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- Use of enyne compounds in the synthesis of insect pheromones
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A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.
- Ishmuratov,Ishmuratova,Odinokov,Tolstikov
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- Pheromones via organoboranes-1: Stereospecific syntheses of (Z)-11-hexadecenal, (Z)-11-hexadecen-1-ol and (Z)-11-hexadecen-1-yl acetate
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Highly stereospecific and efficient syntheses of (Z)-11-hexadedcenal (2), (Z)-11-hexadecen-1-ol (3) and (Z)-11-hexadecen-1-yl acetate (4) through hydroboration-hydridation (LAH)-hydroboration with dibromoborane-dimethylsulphide complex, followed by iodine induced rearrangement are described.
- Dhillon, Ranjit S.,Singh, Jasvinder
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p. 757 - 759
(2007/10/02)
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- A HIGHLY STEREOSELECTIVE SYNTHESIS OF E-11-HEXADECEN-1-OL ACETATE: PURE TRANS PHEROMONES FROM ACYLSILANE/YLIDE CHEMISTRY
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The preparation of E-11-hexadecen-1-ol acetate, a sex attractant of the sweet potato leaf folder moth, Brachmia macroscopa (and other related species, eg.Mamestra brassicae and Sceliodes cordalis) in >99percent purity is described.
- Soderquist, John A.,Anderson, Charles L.
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p. 2777 - 2778
(2007/10/02)
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- Synthesis of (Z)-11-Hexadecen-1-yl Acetate and Its (E)-Isomer
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Synthesis of (Z)-11-hexadecen-1-yl acetate (I) and the corresponding E-isomer (II) is described.The stereochemistry of the products could be fixed by selective reduction of the common intermediate hept-2-yn-1-ol (III); hydrogenation over Lindlar's catalyst for the sequence of reactions towards I and LAH reduction for the sequence of reactions towards II.
- Vig, O. P.,Sharma, M. L.,Vohra, Neelam,Sabharwal, Arun,Huq, M. A.
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p. 1069 - 1070
(2007/10/02)
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- Exo- and Endohormones. XI. Synthesis of Monounsaturated Sex Pheromones of Lepitoptera via α-Dicetones
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α-Dicetones (5), prepared starting either with cyanohydrines (1) or with N,N-diethyl oxamate (6), were converted via the dihydrazones 11 ito acetylenes (12).Replacement of the protecting group by the acatate group and partial stereoselective reduction of the triple bond led finally to the title conpounds.
- Oprean, I.,Ciupe, Hilke,Gansca, Lucia,Hodosan, F.
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p. 283 - 289
(2007/10/02)
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- INSECT PHEROMONES AND THEIR ANALOGS. XVII. SYNTHESIS OF (Z)-HEXADEC-11-ENAL AND (Z)-HEXADEC-11-EN-1-YL ACETATE
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(Z)-Hexadec-11-enal and (Z)-hexadec-11-en-1-yl acetate - components of the sex pheromone of insects of the genera Heliothis and Manestra, respectively - have been synthesized by the condensation of undec-10-enal with hex-1-yne, deoxygenation of the heptadec-1-en-12-yn-11-ol formed via the corresponding tosylate to heptadec-1-en-12-yne, and the selective oxonolysis of the latter.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Tolstikov, G. A.
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p. 365 - 368
(2007/10/02)
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- Vinylic Organoboranes. 3. Pheromones via Organoboranes. 1. Stereospecific Synthesis of Straight-Chain Z-Monoolefinic Insect Pheromones via Lithium (1-Alkynyl)trialkylborates
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Various insect pheromones with straight-chain Z-monoolefinic structures have been prepared from lithium (1-alkynyl)trialkylborates.Treatment of lithium (1-alkynyl)trialkylborates, readily prepared from lithium acetylides and trialkylboranes, with iodine under mild conditions produces the corresponding alkynes in essentially quantitative yield.Monohydroboration of the resultant alkyne with 9-borabicyclononane yields the corresponding (Z)-olefin after protonolysis.The combination of these two reaction sequences provides a general route for the synthesis of (Z)-olefins.The position of the double bond and the carbon-chain length are easily controlled by properly choosing the initial reactants.The incorporation of functional groups is also easily achieved because of the mild reaction conditions and the tolerance of hydroboration to many functional groups.High yield and purity of the products are obtained.
- Brown, Herbert C.,Wang, Kung K.
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p. 4514 - 4517
(2007/10/02)
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- A General Approach to the Synthesis of Mono-olefinic Insect Sex Pheromones of Z- or E-Configuration
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A series of insect sex pheromones and structually related olefins have been synthesized with high stereoisomeric purity by two sequential cross-coupling reactions.Starting with (Z)- or (E)-1-bromo-2-phenylthioethene, (1) and (2), and Grignard reagents in the presence of nickel or palladium catalysts, two types of compounds have been prepared: (i) 1,2-dialkylethenes and (ii) alkenyl acetates.In the synthesis of Z-isomers, the first step involves a cross-coupling reaction of compound (1) with the appropriate Grignard reagent in the presence of a catalytic amount of .The second cross-coupling reaction is performed on the intermediate (Z)-phenylthioalkenes using a different Grignard reagent in the presence of (dppe=Ph2PCH2CH2PPh2) as a catalyst.In the synthesis of E-isomers both steps are cross-coupling reactions of Grignard reagents in the presence of as a catalyst, the first step involving compound (2) and the second step involving the intermediate (E)-phenylthioalkenes obtained.The Grignard reagents used in the synthesis of the alkenyl acetates derive from protected ω-halohydrins.
- Fiandanese, Vito,Marchese, Giuseppe,Naso, Francesco,Ronzini, Ludovico
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p. 1115 - 1120
(2007/10/02)
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- PHEROMONES OF INSECTS AND THEIR ANALOGS. V. A NEW APPROACH TO THE SYNTHESIS OF THE SEX PHEROMONES OF INSECTS OF THE ORDER Lepidoptera WHICH IS BASED ON THE SELECTIVE OZONOLYSIS OF 1-METHYLCYCLOOCTA-1Z,5Z-DIENE
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A new synthesis of 1-acetoxyalk-Z-enes (sex pheromones of insects of the order Lepidoptera) has been developed which is based on the selective ozonolysis of 1-methylcycloocta-1Z-5Z-diene - a cooligomer of isoprene and butadiene.
- Tolstikov, G. A.,Odinokov, V. N.,Galeeva, R. I.,Bakeeva, R. S.,Akhunova, V. R.
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p. 219 - 224
(2007/10/02)
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- Composite insect attractant for male cabbage moths and a process for preparing its active agents
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The invention relates to a composite insect attractant for male cabbage moths (Mamestra brassicae) containing (Z)-11-hexadecenyl acetate and (Z)-11-heptadecenyl acetate as active agents in a weight ratio of 70 to 90:80 to 1, optionally along with a liquid or solid adjuvant. An insect trap can contain the composition which is used for attracting and trapping cabbage moth. Their mating is disrupted by air permeation techniques. (Z)-11-heptadecenyl acetate is a synergistically active new compound. The composition according to the invention produces a significantly stronger stimulating reaction on male cabbage moths than the known sex lure compositions.
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- Kolbe Synthesis of Unsaturated Pheromones by Coelectrolysis with 5-Alkynoic Acids
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The alkynoic acids 5a - g are synthesized by coelectrolysis of 5-alkynoic acids 2a - c with dicarboxylic monoesters 3a - d.By reduction, Lindlar-hydrogenation, and acetylation these are converted into pheromones such as (Z)-11-hexadecenyl acetate (7b), the pheromone of Mamestra brassicae. 2a - c can be prepared by alkynylation of 1-bromo-3-chloropropane to 1a - c, substitution by cyanide and hydrolysis.
- Seidel, Wolfgang,Schaefer, Hans J.
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p. 3898 - 3903
(2007/10/02)
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- INSECT PHEROMONES AND THEIR ANALOGS III. SYNTHESIS OF THE SEX ATTRACTANTS OF SOME LEPIDOPTERA
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A new route to the synthesis of a number of attractants of Lepidoptera (Argyrotaenia velutinana, Mamestra configurata, and Lycorea ceres ceres) have been developed.These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively.The constants of the substances obtained agree completely with those given in the literature.The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction.To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained.The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.
- Dzhemilev, U. M.,Balezina, G. G.,Volkova, L. A.,Krivonogov, V. P.,Tolstikov, G. A.
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