- Pheromone components of the wheat stem sawfly: Identification, electrophysiology, and field bioassay
-
Volatiles collections and cuticular extracts of the wheat stem sawfly, Cephus cinctus Norton (Hymenoptera: Cephidae), were analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) in order to detect possible pheromone components of
- Cosse, Allard A.,Bartelt, Robert J.,Weaver, David K.,Zilkowski, Bruce W.
-
-
Read Online
- ISOLATION AND IDENTIFICATION OF A SUPPLEMENTARY COMPONENT OF THE SEX PHEROMONE OF Mamestra brassicae FEMALES
-
Using gas-liquid chromatography and mass spectrometry, from an extract of the sex pheromone of females of the cabbage moth Mamestra brassicae L. an additional component of the pheromone has been isolated and identified - heptadec-cis-11-en-1-ol acetate.
- Nedopekina, S. F.,Kovalev, B. G.,Khlebnikov, V. A.
-
-
Read Online
- Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate
-
The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate. According to the method, malonic acid and 9-bromo-1-nonyl alcohol are used as two starting raw materials. The method comprises the following steps: carrying out a Knoevenagel condensation reaction on malonic acid and propionaldehyde inthe presence of piperidine acetate to generate (E)-3-pentenoic acid, then carrying out lithium aluminum hydride reduction to obtain (E)-3-penten-1-ol, carrying out bromination reaction, and refluxingwith triphenylphosphine in acetonitrile to obtain (E)-3-pentenyltriphenylphosphine bromide; carrying out a PCC oxidation reaction on 9-bromo-1-nonanol to obtain 9-bromononanal, and then reacting the 9-bromononanal with potassium acetate to obtain 9-acetoxynonanal; and finally, carrying out a Wittig reaction on (E)-3-pentenyltriphenylphosphine bromide and 9-acetoxynonanal so as to obtain (9Z, 12E)-9,12-tetradecadien-1-ol acetate. An E-type double bond is constructed by utilizing the Knoevenagel condensation reaction of malonic acid and propionaldehyde, and the method has the advantages of mildreaction conditions, environmental friendliness, simple synthetic route and the like.
- -
-
-
- Nucleoside analogues with a 1,3-diene-Fe(CO)3 substructure: Stereoselective synthesis, configurational assignment, and apoptosis-inducing activity
-
The synthesis and stereochemical assignment of two classes of iron-containing nucleoside analogues, both of which contain a butadiene-Fe(CO)3 substructure, is described. The first type of compounds are Fe(CO)3-complexed 3'-alkenyl-2′,3′-dideoxy- 2′,3′-dehydro nucleosides (2,5-dihydrofuran derivatives), from which the second class of compounds is derived by formal replacement of the ring oxygen atom by a CH2 group (carbocyclic nucleoside analogues). These compounds were prepared in a stereoselective manner through the metal-assisted introduction of the nucleobase. Whilst the furanoid intermediates were prepared from carbohydrates (such as methyl-glucopyranoside), the carbocyclic compounds were obtained by using an intramolecular Pauson-Khand reaction. Stereochemical assignments based on NMR and CD spectroscopy were confirmed by X-ray structural analysis. Biological investigations revealed that several of the complexes exhibited pronounced apoptosis-inducing properties (through an unusual caspase 3-independent but ROS-dependent pathway). Furthermore, some structure-activity relationships were identified, also as a precondition for the design and synthesis of fluorescent and biotin-labeled conjugates. I gotta Fe-ling: Iron-containing nucleoside analogues, which were first synthesized during an exercise in stereoselective π-complex chemistry, exhibited pronounced cytotoxic and apoptosis-inducing activities, even against resistant cancer cell lines. Both hetero- (X=O) and carbocyclic (X=CH2) compounds were studied, and a synthetic route to R′-labeled derivatives was developed as a precondition for future biological experiments. TDS=thexyldimethylsilyl. Copyright
- Hirschh?user, Christoph,Velcicky, Juraj,Schlawe, Daniel,Hessler, Erik,Majdalani, André,Neud?rfl, J?rg-Martin,Prokop, Aram,Wieder, Thomas,Schmalz, Hans-Günther
-
p. 13017 - 13029
(2013/10/01)
-
- Tandem application of C-C bond-forming reactions with reductive ozonolysis
-
Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2- addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protocols.
- Willand-Charnley, Rachel,Dussault, Patrick H.
-
-
- Pyridine is an organocatalyst for the reductive ozonolysis of alkenes
-
Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.
- Willand-Charnley, Rachel,Fisher, Thomas J.,Johnson, Bradley M.,Dussault, Patrick H.
-
supporting information; experimental part
p. 2242 - 2245
(2012/06/30)
-
- A mild one-pot conversion of alkenes into amines through tandem ozonolysis and reductive amination
-
The selective reduction of hydroperoxyacetals to aldehydes by sodium triacetoxyborohydride provides the basis for a mild one-pot synthesis of amines from alkenes. Georg Thieme Verlag Stuttgart.
- Kyasa, Shivakumar,Fisher, Thomas J.,Dussault, Patrick H.
-
experimental part
p. 3475 - 3481
(2011/12/04)
-
- Facile synthesis of mill moth's sex pheromone components
-
An improved method for the preparation of mill moth's sex pheromone components in high diastereomeric purity is described. Copyright Taylor & Francis Group, LLC.
- Hornyanszky, Gabor,Rohaly, Janos,Novak, Lajos
-
p. 1533 - 1540
(2008/09/20)
-
- Ozonolysis in solvent/water mixtures: Direct conversion of alkenes to aldehydes and ketones
-
(Chemical Equation Presented) Ozonolysis of alkenes in the presence of solubilized water results in the direct formation of aldehydes and/or ketones, avoiding the need to isolate or decompose ozonides.
- Schiaffo, Charles E.,Dussault, Patrick H.
-
p. 4688 - 4690
(2008/09/21)
-
- Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid
-
A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.
- Kharisov,Botsman,Botsman,Ishmuratova,Ishmuratov,Tolstikov
-
p. 145 - 148
(2007/10/03)
-
- Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): Natural oxidation to pheromone components
-
The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, ω-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.
- Bartelt, Robert J.,Cosse, Allard A.,Petroski, Richard J.,Weaver, David K.
-
p. 385 - 405
(2007/10/03)
-
- STADIES ON THE WITTIG REACTION (VIII). STEREOSELECTIVITY OF DIPHENYL ALLYLIC PHOSPHONIUM YLIDS IN WITTIG REACTION
-
Ylids generated from diphenyl allylic phosphonium salts reacted with aliphatic aldehydes containing a terminal oxygen functionized group in the absence of lithium salt to give E,E-conjugated dienes.The stereoselectivity depends mainly on the base used, the allylic part of phosphonium salts also shows some effect on stereochemistry.Eight conjugated dienic insect sex pheromones and related analogues with different E-selectivities were obtained.
- Wenfang, Huang,Jun, Zhu,Wenjing, Xiao,Yanneng, Deng
-
-
- Composite insect attractant for male white-line dart moths and a process for preparing the active ingredients thereof
-
The invention relates to a composite insect attractant for male white-line dart moths [Scotia segetum] containing 7[Z]-dodecen-l-ol acetate of the formula [I] STR1 and 9[Z]-tetradecen-l-ol acetate of the formula [II] STR2 as active agents in a weight ratio of I to II of [50-99]:[50-1], optionally along with a liquid or solid adjuvant. Another object of the invention is an insect trap containing said composition and a process for attracting and trapping male white-line dart moths as well as a process for disrupting their mating by air permeation technique. The invention relates further to a novel process for the preparation of the active ingredients of the composition.
- -
-
-