- OXIDATION OF HEXADEC-11Z-EN-1-OL BY Cr(VI) REAGENTS ON POLYMERIC SUPPORTS
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A method is proposed for the oxidation of hexadec-11Z-en-1-ol to hexadec-11Z-enal by Cr(VI) reagents on polymeric supports.
- Verba, G. G.,Asanova, M.,Plugar', N. Ya.,Abduvakhabov, A. A.,Khakimdzhanov, B. Sh.,Musaev, U. N.
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- Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
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Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
- Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
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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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Paragraph 0025
(2019/05/15)
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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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- Process for oxidation of fatty alkenols to alkenal pheromone products
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The present invention relates, in part, to an improved process for oxidation of alcohols containing oxidatively sensitive functional groups, using inexpensive reagents under mild reaction conditions to provide high yields of carbonyl products such as aldehydes or ketones. In certain embodiments, an aldehyde product is obtained by contacting an oxidatively sensitive alcohol, such as an alkenol, with an oxidant and a TEMPO catalyst under conditions sufficient to convert the alkenol to the aldehyde.
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Page/Page column 13; 14; 15
(2018/06/08)
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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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Paragraph 0223
(2018/09/12)
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- SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
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In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
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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 0181; 0182
(2013/09/12)
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- Concise syntheses of insect pheromones using Z-Selective cross metathesis
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Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
- Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.
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p. 310 - 314
(2013/02/23)
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- Method for Producing Aldehyde and Ketone
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Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.
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Page/Page column 5-6
(2011/11/30)
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- Oxidation of unsaturated primary alcohols and ω-haloalkanols with 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
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Unsaturated primary alcohols and ω-haloalkanols, all applied in pheromone synthesis, are oxidized to the corresponding aldehydes using 4-acetylamino-2,2,6,6-tetramethylpiperidine- 1-oxoammonium tetrafluoroborate (1a). Three methods are compared with one another; oxidations with la and silica gel, oxidations with la in the presence of pyridine, and pyridinium chlorochromate (PCC). Georg Thieme Verlag Stuttgart.
- Zakrzewski, Jerzy,Grodner, Jacek,Bobbitt, James M.,Karpinska, Monika
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p. 2491 - 2494
(2008/02/13)
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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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- Pheromone synthesis, CLXXV: Synthesis of koiganal I and II, the sex pheromone components of the webbing clothes moth
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Koiganal I [(E)-2-octadecenal (1)] and II [(2E,13Z)-2,13-octadecadienal (2)], the female-produced pheromone components of the webbing clothes moth (Tineola bisselliella), were synthesized. VCH Verlagsgesellschaft mbH, 1997.
- Takikawa, Hirosato,Takenaka, Motonobu,Mori, Kenji
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p. 139 - 140
(2007/10/03)
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- Stereoselective hydrogenation in synthesis of components or component precursors of pest insect pheromones
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A study is made of stereoselective hydrogenation of high-molecular-weight acetylenic carbinols on supported copper catalysts in ethanol to form cis-olefinic alcohols, components or intermediates of components of pheromones of pest insects: cotton and gray grain cutworm moths.
- Kartonozhkina,Pak,Slepov,Izdebskaya
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p. 1013 - 1015
(2007/10/03)
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- Palatable solid pesticidal compositions of ethylene and vinyl acetate copolymer
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The invention comprises compositions in solid form of ethylene/vinyl acetate copolymer with an effective amount of bioactive agent, a protein/carbohydrate-lipid source, 0 to 20% of an edible oil and optionally an attractant, dye, preservative, adversive agent and biomarker and the use, thereof, to control pests.
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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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p. 116 - 118
(2007/10/02)
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- SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)
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The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).
- Sorochinskaya, A.M.,Kovalev, B.G.
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p. 621 - 624
(2007/10/02)
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- MASS-SPECTROMETRIC STUDY OF THE PHEROMONE OF THE COTTON BOLLWORM AND ITS PRECURSORS
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The structures of the products of intermediate stages of the synthesis of the sex pheromone hexadec-11Z-enal that are labile to electron impact have been studied with the aid of low-resolution mass spectrometry and metastable ions.
- Igrasheva, G. A.,Razakov, R. R.
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p. 208 - 212
(2007/10/02)
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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 facile synthesis of cotton bollworm (Heliothis armigera) pheromone components: (Z)-11-Hexadecenal and (Z)-9-hexadecenal
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(Z)-Hexadecenal (1) and (Z)-9-hexadecenal (2) have been synthesised starting from easily accessible propargyl alcohol.Alkylation of propargyl alcohol yields 3 and 4, which on acetylene-zipper reaction give terminal acetylenes (5 and 6, R'=H).Alkylation of 5 and 6 followed by depyranylation afford 7 and 8.Partial cis-hydrogenation of these with P2Ni followed by PCC oxidation give compounds 1 and 2.
- Mithran, S.,Mamdapur, V. R.
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p. 755 - 756
(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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- Azeotropic purification of Z-11-hexadecenal
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Production of essentially pure Z-11-hexadecenal by azeotropic distillation is described. Contacting a mixture of Z-11-hexadecenal, hexadecene and hexadecadiene with dimethylsulfoxide and subjecting the blend to azeotropic distillation allows for the removal of hydrocarbon impurities from the aldehyde. Contacting a mixture of Z-11-hexadecenal and hexadecenol with a C2 -C4 glycol and subjecting the blend to azeotropic distillation conditions allows for the recovery of a glycol-aldehyde azeotrope from which essentially pure aldehyde is readily recovered. A mixture comprising Z-11-hexadecenal, hexadecene, hexadecadiene and hexadecenol can be sequentially treated according to the above-described azeotropic distillation steps in order to provide essentially pure Z-11-hexadecenal.
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