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Author: Subject: Acetaldahyde and Fruit flies.
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[*] posted on 28-9-2009 at 14:50
Acetaldahyde and Fruit flies.


I don't know if this deserves a thread all its own but it is just an interesting observation I just made a little bit ago.

I have been looking into different methods of producing AcOH from Ethanol but I keep making Acetaldahyde which leaves the solution unoxidised in large quantitys. I decided to try a solution of MnSO4 in a partioned cell and electrochemical oxidise it to see if I could produce any Acetic acid at all. I turned on the voltage and made sure everything was running correctly. It seemed to be going ok and within seconds the solution turned cloudy. Checking to see if there was any smell of Acetic acid showed none had been produced yet or atlest not enough to be detected so I thought to give it more time and went inside to cook some dinner.

After about 1 hour or so I came back to something that struck me as cool and clearly showed the link between simple chemicals and biological creatures. The whole of the electrochemical cell when I came back to check on it was covered in fruit flys. Hundreds of them everywhere making the cell almost black in appearence.

Obviously there is a strong link between the Acetaldahyde that the cell is producing and pheromonal instincts of the fruit fly. From their point of view my electrochemical cell must have looked like a giant rotting apple ready for the picking. Sad that all they are going to find is a big bowl of warm H2SO4 with alcohol and MnSO4 in it.
:D

Just thought I would share with everyone because its something I thought was pretty neat when I seen it. What other simple chemicals do you think could be used to attract various insects and critters alike? I remember when I was running the cell before in attempts to produce Benzaldahyde I had on more then one occasion have to pull dragon flys out of the cathode solution so I can't help but wounder if BnO mimics some kind of pheromone of the dragonfly as well.

[Edited on 29-9-2009 by Sedit]





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[*] posted on 28-9-2009 at 14:56


Thank whomever that you were not making N-3-methylbutylacetamide, the yellow-jacket stinging pheromone. I have a nest of these bastards in the front yard and discovered them the "hard way".

Yellowjackets-son of a-ouch-bastards-nest,

O3

Attachment: Yellowjacketpheromone_Landolt.pdf (135kB)
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[*] posted on 28-9-2009 at 15:07


Given what I just seen from the swarming nature of fruit flys around this chemical I would not want to imagine the power some of these chemicals could have on larger more dangerous(and already prone to swarming such as the bees). Brings to mind biblical plague type behaviour from insects.

Did you ever have methylbutylacetamide near these yellow jackets to see how they reacted Ozone?





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[*] posted on 28-9-2009 at 15:34


Yes and no. Pure compound? HELL NO! I learned about this *after* I squashed one that was stinging the hell out of me and the rest attacked. Apparently, when stinging and when crushed, these wasps (Vespula, either vulgaris or squamosa) emit the N3MBA and the whole lot of them give chase. The ones on you will sting (almost at once, like imported fire ants, S. invicta), and will grab on to you making them difficult to remove.

Apparently, a dab of this, and your toast.

Extremely unpleasant; frightful.

O3

OK, maybe a dab on the end of a looooooong stick (with a dark target affixed) would be interesting. Or, a remote- control vehicle might suffice. Might want to call the paramedics, first.



[Edited on 28-9-2009 by Ozone]




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[*] posted on 28-9-2009 at 18:46


Hmmm. I have used a mixture of water, detergent, and vinegar......To kill fruitflies.

Just put it in an uncapped bottle.....they fly in, and drown.

Might not be a pheromone. They are attracted to the odor, because it signals, fermenting fruit.

Yummy! Yummy! Fruit Fly Food!
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[*] posted on 28-9-2009 at 18:57


–noun Animal Behavior. any chemical substance released by an animal that serves to influence the physiology or behavior of other members of the same species. *

Perhaps we should modify this to read ...released by an animal (or fruit)...

Just kidding. I am sure this smells delicious to them. Interestingly, they appear to usually go for the ethanol. A mutant batch of melanogaster that went berserk over acetaldehyde has been documented.

*http://dictionary.reference.com/browse/pheromone

Cheers,

O3




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[*] posted on 28-9-2009 at 19:31


So your saying that they go for Ethanol much of the time as well? I sure hate to think that a mutant batch of fruit flys going nuts over the Acetaldahyde are what are attacking my cell.... then again a mutant batch of critters is every mad scientist dreams :D .


BTW I have a site that is shows a massive amount on insect pheromones that I will look so I can post the link.





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[*] posted on 28-9-2009 at 19:47


Yellowjackets? The name is applied to several paper wasps of the family Vespidae, with yellow and black stripes, especially the mostly eastern American wasp Vespula Maculifrons; see http://en.wikipedia.org/wiki/Vespula and http://en.wikipedia.org/wiki/Yellowjacket .

I wonder if the same pheromone could be used to attract and destroy the main introduced pest wasp species here in New Zealand, the German or "Waikato" wasp, Vespula Germanica, dealt with on http://en.wikipedia.org/wiki/German_wasp , and several New Zealand web-sites including http://www.doc.govt.nz/upload/documents/conservation/threats... .

It looks very much like Vespula Maculifrons. They arrived in New Zealand around 1945, allegedly in the form of a fertilized hibernating queen wasp in a cargo of scrap aluminium from junked World War 2 military aircraft from Europe, which was destined for melting-down, and which had been sent to the Waikato region (which has a light-aircraft industry). They quickly spread over the rest of the North Island during the 1950s, and then "hitched a ride" into the South Island.

The live mainly in nests in the ground, and sometimes in big old hollow trees. In my part of New Zealand, the nests frequently keep going over winter, reaching huge sizes unless found and destroyed. As well as being a hazard from their stings, they are a menace to the bee-keeping and fruit-growing industries, and to native insects and birds by helping themselves to the honey-dew secreted in summer by some native tree species, and by eating insects and sometimes chicks.

A bounty was once paid in New Zealand for each German queen wasp collected in the springtime (when emerging from hibernation) and given to the Department of Agriculture. But mass destruction of overwintering queens had virtually no effect on wasp populations the following summer. (Even if 99.9 percent of the potential queens were eliminated, the same number of annual colonies would remain.)

In recent years, the "common wasp", Vespula Vulgaris (which has broader black bands and is much more aggressive, see http://en.wikipedia.org/wiki/Vespula_vulgaris and especially http://en.wikipedia.org/wiki/Common_wasp ), somehow got into New Zealand, in spite of much tighter biosecurity controls on imported goods, possibly by being blown across the sea from Australia. Also found here since 1979 is the Asian paper wasp (Polistes chinensis, which is similar in color but much slimmer, builds suspended nests like the related native red wasp containing only up to a few dozen wasps, and eats monarch butterfly caterpillars). However, they are not as common as the German wasp, except for Vespula Vulgaris in the South Island.

Wasp venom contains a chemical "alarm pheromone," released into the air, signaling guard wasps to come and sting whoever or whatever gets in their way, literally "scrambling" like the Air Force. If one kills a wasp just outside a nest by hitting it, that wasp will give off a pheromone which will penetrate the nest. Some flowers (particularly orchids) and fruits have volatile scents, including Chiloglottone, that appear to mimic the pheromone.

p11150nsil-GermanWasp(Left)&CommonWasp(Right)-Queens.jpg - 41kB

[Edited on 30-9-09 by JohnWW]
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[*] posted on 29-9-2009 at 14:32


Quote: Originally posted by JohnWW  

Wasp venom contains a chemical "alarm pheromone," released into the air, signaling guard wasps to come and sting whoever or whatever gets in their way, literally "scrambling" like the Air Force. If one kills a wasp just outside a nest by hitting it, that wasp will give off a pheromone which will penetrate the nest.
[Edited on 29-9-09 by JohnWW]


Might be interesting to synthesize this pheromone, then put some on the clothes of someone you don't like, like say an ex-girlfriend for example....

Just kidding, please don't actually do this, but it is a funny thought.

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[*] posted on 29-9-2009 at 15:55


It's funny unless it's happening to you. OK, even then it's funny, but only later (while explaining the event to others or watching the video of yourself running in circles and screaming like a bitch).

Anyway,

I had thought of burst charges, but then I considered it "cruel and unusual".

And hilarity ensues.

*pssht...burst charges away...Roger that...WASP crew on deck and live in 5...4...3...2..."

Or, I suppose we could scramble the FRUIT FLY squadron, instead (only effective in California). WHOA.

Seriously:

I was only stung about 7 times, and I was lucky. Targets treated with N3MBA saw over 100 "hits" (without rousting the nest), I have attached a picture of my foot (the one with only *one* sting, which remained like this for about 7 days. Imagine 100.

Brrrrrr.

O3

Vsquamosa_wrath-of_1sting_right-foot_Aug2009_smaller.jpg - 197kB

[Edited on 29-9-2009 by Ozone]




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[*] posted on 29-9-2009 at 21:06


Lots of Yellow jackets here in the US. Not really much of a problem. Provided you don't knock down a nest. Even then, a quick sprint, will carry you out of danger.

Every supermarket, gardencenter, and hardware store, sells effective Yellow Jacket poisons.

We worry much more, about "killer" bees. They look just like regular honey bees, but they are much more aggressive. If you accidentally piss them off, and it doesn't take much to piss them off.....in a mass....they will make a valiant and protracted effort to sting you to death.

Descended from super aggressive African honey bees, accidentally released in South America, they have gradually migrated, as far north as San Francisco, California. That seems to be their limit.

Fortunately, they seem unable to survive in cold Winter areas. The Queens produce a lot of brood, and the hives retain a relatively small reserve of food honey. Too small of a reserve.

When killer bees go too far North, where there is no winter nectar supply, their hives starve to death over the Winter.

[Edited on 30-9-2009 by zed]
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[*] posted on 24-10-2009 at 08:53


Pheromone synthesis might be a pretty interesting concepts; a cross between chemistry and biology. My only question is, how would one go about the synthesis of this compound? Given one had on hand, 4- methyl pentanoic acid (isohexanoic acid), the synthesis would not be very difficult I presume. Reaction of the compound with ammonia would produce 4- methyl pentanamide, which one could easily convert to the primary amine via the hoffmann route (using the fairly common reagents of bromine and sodium hydroxide, in an aqueous solvent). Finally, reacting the 3- methyl butylamine product with a dilute solution of acetic acid (I would use a diluted reagent for evident safety purposes :D) would give use the necessary 3- methylbutyl acetamide (wasp pheromone).

The only trouble is, isohexanoic acid, isn't exactly readily available for the home chemist. Any ideas on how the hell one would go about synthesising it?
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[*] posted on 25-10-2009 at 03:48


Quote: Originally posted by Theophrastus_2  
Finally, reacting the 3- methyl butylamine product with a dilute solution of acetic acid (I would use a diluted reagent for evident safety purposes :D) would give use the necessary 3- methylbutyl acetamide (wasp pheromone).


That ends up as an acetate salt of your amine...

Anyway... you could probably make isoamyl amine from the corresponding halide or alcohol before reacting with acetic anhydride.

sparky (~_~)

P.S. Blattellaquinone has a relatively simple structure... making it in the garage is bound to yield... "interesting"... results. ;)




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[*] posted on 25-10-2009 at 06:00



Quote:
Blattellaquinone, also known as gentisyl quinone isovalerate, is a sex pheromone of the German cockroach (Blattella germanica). Blattellaquinone is secreted by females to attract male cockroaches.


How disgusting but oh what fun it would be in the town near me where most of the people are dirty A-holes anyway.



Synthesis seems simple enough according to this,

Source:http://pubs.acs.org/cen/news/83/i08/8308notw1.html

Not sure its exactly something I would want to synthesis around my house though given that 5000 female roaches only produce 5ug of the compound meaning that even if you only synthesized one half of a gram of the material male roaches from miles away would think that there was an orgy going on at your place.

[Edited on 25-10-2009 by Sedit]





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[*] posted on 1-6-2010 at 04:53


I one made paraformaldehyde by heating POM (the engineering plastic) It went so good that a large excess of HCHO was released in the lab, at the moment when I started to tear my ass off, I took the apparatus and ran out of the lab with it, and left it as it was, when I came back a lot of -do-not-know-what- insect collected around it.. the one which springing with a cracking sound when falls to its back to get on foot again.. There was so many of them that I must not had been a coindicence! strange!
Anyone with a pheromone synth that attract rich and clever chemistry liking girls?:)
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[*] posted on 1-6-2010 at 06:23


Click Beetles, fun lil buggers we use to play with alot when we where kids putting a bunch in a jar and shaking it up to watch them go crazy bouncing around inside. One should expect most insect pheromones to be simple compounds such as formaldahyde or acetaldahyde so that the creature does not expend to much energy in making it.


Quote:
Anyone with a pheromone synth that attract rich and clever chemistry liking girls?

Rich, smart and liking chemistry, sure as for alot don't ya. Why not just a hot dumb blond who likes that you do chemistry.... that would be ok with me. However in rome they use to use a concoction taken from the gladiators which has all the attributes of a human pheromone system. The lead gladiator would enter a suana and coat himself in olive oil periodicly scraping the oil into a collection bin. This oil was extracted with EtOH and the extract used to "increase the vigor" of older woman.... I take this as meaning it made them horny. There is a chemical exceated in sweat that is known to increase cortisol levels in woman but I can not remember the exact name of it right now. I believe its Aldosterone but don't quote me on that.





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[*] posted on 1-6-2010 at 07:38


"click beetles" ehh:) I like the coherence of english!
what about shaking 1000 bombardier beetle in a closed stainless steel can?:)
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[*] posted on 1-6-2010 at 07:49


Yeh english people are lazy at naming things so we just name it as it sounds....
"Hey whats that noise..." ...
...."Eh must be one of those darn Click beetle thingys"


As far as a SS can... yeh I can picture that making one hell of a racket. Make some formaldahyde and catch some:D.

Honestly im kind of shocked the government hasn't invested more intrest in the control of insects and animals in warfar. I think it could be like the good ol' days back in egypt with locus and scab flys fucking the enemys day up.





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[*] posted on 2-6-2010 at 09:19


Quote: Originally posted by Jimmymajesty  
I one made paraformaldehyde by heating POM (the engineering plastic) It went so good that a large excess of HCHO was released in the lab, at the moment when I started to tear my ass off, I took the apparatus and ran out of the lab with it, and left it as it was, when I came back a lot of -do-not-know-what- insect collected around it.. the one which springing with a cracking sound when falls to its back to get on foot again.. There was so many of them that I must not had been a coindicence! strange!
Anyone with a pheromone synth that attract rich and clever chemistry liking girls?:)


There is a substance that can attract rich dumb girls called cocaine.

How did you make formaldehyde out of POM (also called Delrin)? Seems like a good method.

- Ok back on topic about bugs -

Theodore Gray's driveway was covered in butterflies after he set off a sodium explosion. http://www.periodictable.com/Stories/011.2/

I also read about someone who put a bunch of millipedes in a jar and woke up on the floor after the HCN fumes knocked him out upon opening :o




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[*] posted on 2-6-2010 at 13:30


I looked up some pheromones on the net, and all I can say regarding their synthesis.. forget about it..
It would require soo deep knowledge in chemistry that I can only dream of.. and requires exotic chems that are out of reach.. at least for me..

Yeah blattellaquinone is easy if you have blattellaquinone precursors:)

BTW palstic gears from an old casette recorder are usually made of pure POM.. or HCHO ethylene glycol copolymer, heat it for some time and after a small explosion cork the flask and lead the forming gases into water, the paraformaldehyde will precipitate in the water, take care not to clog the glass or plastic tube, also note that the initial explosion is quite violent, like hydrogen + oxygen mixtures.
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[*] posted on 2-6-2010 at 14:18


Here is a decent collection of pheromone synthesis.
http://www.scielo.br/scielo.php?pid=S0103-50532007000600003&...

Where as alot of these appear complex there are inumerable amounts of simple pheromones as well such as aldahyde, phenol and hydroquinone based ones which are quite common in insects

I love the idea about the butterflys being brought in by Sodium. Does this mean that simple table salt being +(Na)-(Cl) will attract them as well since what remained in his driveway the next day couldn't have been much more then either NaOH or carbonates.

And last but not least what about this,
http://www.ice.mpg.de/bol/research/ectocarpus/ectocarpene.ht...

Brown algae pheromones, What use could they serve?





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[*] posted on 3-6-2010 at 01:36


I don't know if the NaCl would, but Na2CO3, which is what is what was most likely there, and is also likely to be found in mudd puddles is easy to get or make -- I will hopefully remember to try this once a few butterflies are out -- I wonder how it is they detect the sodium? It isn't like something that could be smelled easily. Perhaps a spray bottle of a sodium carbonate solution would attract them more effectively then having it on the drive way?
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