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Author: Subject: The ant & the potato chip
Ritter
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[*] posted on 25-7-2008 at 19:00
The ant & the potato chip


I've lived in the same house for over 20 years, so both my habits & those of area insects are both very familiar.

This week brought a major change: I decided I enjoyed having potato chips with my mid-day sandwich. And a few days thereafter brought another but apparently unrelated major change: an infestation of little black ants.

The ants were apparently driven to the Tupperware container that held the chips as they could be seen intently circling the plastic interface between the top & main container.

It didn't take much thought to put together a working hypothesis for these apparently unrelated occurrences: the ants were being attracted from afar by volatile chemicals given off by the chips.

Since various alkylpyrazines are found both in ant trail-following pheromones & in potato chip volatiles, it didn't take much effort to establish a correlation between the two. The chip's alkyl pyrazines, formed by the Maillard reaction when potatoes are fried, either mimiced or duplicated the local ant species' pheromone that lead them to food sources such as my chips. See the amazing correspondence in the ChemDraw file.

Here is a reference for pyrazine potato chip volatiles: http://ift.confex.com/ift/2000/techprogram/paper_4447.htm

While the compound indicated in red might not be the exact culprit, ant pyrazine pheromones are known to be fairly general in their interspecific attraction ability.

In the spirit of amateur experimentalism, I suggest that other subscribers try this same very simple experiment & report their observations here.







[Edited on 25-7-2008 by Ritter]

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[*] posted on 26-7-2008 at 05:52


The ant infestation phenominon is something of interest for sure. You could have a nearby colony that is so persistant that no pest control method appears to work, then you change something and you never see another ant.

Case and pont-Me and my wife had a friend living with us in our condo and she had all of her non-refrigerated food and condiments in the ground level cabinet. Starting this May, black ants infested our kitchen and we put ant bait, sprayed until we where seeing stars and they kept coming! Even a single crumb or a dirty plate on the counter attracted the horde. As a last ditch effort I intentionally left out a slice of garlic toast overnight to establish a "trail" of ants to find the source. To our frustration they originated from our friend/tenants stash and we insisted she THOROUGHLY clean out the cabinet. The ants never returned even when we left something out overnight.




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[*] posted on 26-7-2008 at 06:03


The room where the potato chip/ant problem occurred has a wall to the outdoors & I observed the ants getting in through a crack in the window frame. A little pesticide & housecleaning eliminated the problem.

As a further test, the container with the chips is now in an inside room. No more ants overnight.

Given the size of these ants, these pyrazine compounds have to be active on the microgram level, so it's not surprising that the odor of chips carried on the breeze through open windows was sufficient to attract them to the odor source.

[Edited on 26-7-2008 by Ritter]




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[*] posted on 26-7-2008 at 06:17


Quote:
Originally posted by Ritter
Given the size of these ants, these pyrazine compounds have to be active on the microgram level, so it's not surprising that the odor of chips carried on the breeze through open windows was sufficient to attract them to the odor source.


Picograms, actually:

http://www.eje.cz/scripts/viewabstract.php?abstract=1143

I'm picturing someone doing a normal lab-scale prep of one of these compounds for an unrelated reason, and returning the next day to find the entire lab completely overrun with ants...
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[*] posted on 26-7-2008 at 06:29


And interestingly the compound 3-ethyl-2,5-dimethylpyrazine seems to be a very common ant trail pheromone. It would not surprise me at all if this chip volatile were indeed the culprit. It's also found in some cheeses & in coffee flavor.

A quick scan of my Aldrich catalog did not find a listing for it. I don't think it is a difficult synthesis. Some possibilities come to mind of how it might be used as a 'prank' CW agent. But your point is valid: how to make macro scale quantities of a volatile insect attractant that is active on the nanogram level without yourself becoming overrun?




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[*] posted on 26-7-2008 at 09:05


Pyrazines & other aroma chemicals arise when organic products such as potato slices are heated to high temperatures. A complex series of reactions between the natural sugars & amino acids results in the formation of a number of aliphatic, aromatic & heterocyclic compounds in what is called the Maillard Reaction.

In J. Agric. Food Chem., 54 (2), 574 -577, 2006 the Swiss aroma chemical company Firmenich study a model system as shown in the ChemDraw. No surprise that 3-ethyl-2,5-dimethylpyrazine is one of the products produced.

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[*] posted on 26-7-2008 at 10:36


That is amazing!
Is anyone going to try to attract a bunch of ants by making this? I would like too, but i don't have any L-alanine, perhaps I may get some.
I am very interested in bug pheromones, because they have so much potential.
I Imagine a lot of bugs use them, perhaps some predatory bugs such as pray mantises, and lady bugs. attracting these sort of bugs could be very beneficial for the gardener who, perhaps doesn't want to use poisons, but suffers from grasshopper and aphid problems.
Cockroaches could possibly be led into sticky traps with some of these synthetic bug pheromones.

I think it would be absolutely wonderful to make a chemical that brings in ants in by the millions :P

And great observations and reasoning Ritter! :D


Edit: Ladybugs obviously have a pheromone, because they will attract each other and hibernate in very large numbers. Perhaps a spray you put on plants that attracts the bugs, is a million dollar idea! I also hear that the chemical can last a "long time" and cause them to hibernate in the same place each year.


[Edited on 26-7-2008 by kclo4]
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[*] posted on 26-7-2008 at 10:54


Quote:
Quote:
Originally posted by kclo4
I would like too, but i don't have any L-alanine, perhaps I may get some.


I believe it is OTC in health food stores. DL-alanine would work just as well, AFAIK.

Quote:

I am very interested in bug pheromones, because they have so much potential.


Yes, they do.

Quote:

I Imagine a lot of bugs use them, perhaps some predatory bugs such as pray mantises, and lady bugs. attracting these sort of bugs could be very beneficial for the gardener who, perhaps doesn't want to use poisons, but suffers from grasshopper and aphid problems.
Cockroaches could possibly be led into sticky traps with some of these synthetic bug pheromones.

I think it would be absolutely wonderful to make a chemical that brings in ants in by the millions :P

And great observations and reasoning Ritter!


Thanks. Chemistry, like the other physical sciences, is all about observation & figuring things out.

Quote:
Edit: Ladybugs obviously have a pheromone, because they will attract each other and hibernate in very large numbers. Perhaps a spray you put on plants that attracts the bugs, is a million dollar idea! I also hear that the chemical can last a "long time" and cause them to hibernate in the same place each year.


There is a very extensive literature on pheromones going back to at least the early 1970s. It's a great area for the amateur experimentalist to work in.






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[*] posted on 26-7-2008 at 10:59


Hmm, I will have to search for the types of pheromones ladybugs release.
From what I have read, some wasps, and rodents also use pyrazine derivatives.
So, if one did this synthesis or variations of it, they would probably run into more then just ants.
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[*] posted on 26-7-2008 at 17:11


I found some references to pyrazine pheromones produced by ladybugs.

Quote:
Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs.

Cudjoe E, Wiederkehr TB, Brindle ID

Analyst 2005; 130:152-5.

Abstract
Static headspace sampling technique coupled with gas chromatography and mass spectrometry was used to investigate the presence of volatile 2-alkyl-3-methoxypyrazines in three different species of ladybugs of the Coccinellidae family. The species investigated were Coccinella septempunctata, Harmonia axyridis and Hippodemia convergens. 2-isopropyl-3-methoxypyrazine (IPMP) was identified in all three species with detectable levels of 2-sec-butyl-3-methoxypyrazine (SBMP) and 3-isobutyl-2-methoxypyrazines (IBMP) in only Hippodemia convergens and Harmonia axyridis species. Relative amounts of 2-alkyl-3-methoxypyrazines based on body mass showed that Hippodemia convergens had the highest levels of all three methoxypyrazines and Coccinella septempunctata the least.



These involve slightly different chemistry than the ant/chip pyrazines:





[Edited on 26-7-2008 by Ritter]

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[*] posted on 26-7-2008 at 17:22


Sphecid wasps also produce a pyrazine attraction pheromone:

Quote:
Pyrazines as marking volatiles in philanthine and nyssonine wasps (Hymenoptera: Sphecidae)

Journal Journal of Chemical Ecology
Publisher Springer Netherlands

ISSN 0098-0331 (Print) 1573-1561 (Online)

Issue Volume 6, Number 4 / July, 1980
DOI 10.1007/BF00990406

Pages 827-835

Subject Collection Biomedical and Life Sciences
SpringerLink Date Monday, January 10, 2005
PDF (1.1 MB)

Pyrazines as marking volatiles in philanthine and nyssonine wasps (Hymenoptera: Sphecidae)

A. -K. Borg-Karlson1, 2 and J. Tengö1, 2

(1) Department of Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden
(2) Ecological Station of Uppsala University, Ölands Skogsby, S-386 00 Färjestaden, Sweden

Received: 28 September 1979 Revised: 14 December 1979

Abstract Males of several sphecid wasps apply volatile secretion on specific sites, perches. The odor is supposed to act in premating behavior as an attracting pheromone. There are strong indications that the scenting material is produced by the mandibular glands. One philanthine species, Philanthus triangulum, and three nyssonine ones, Argogorytes fargei, A. mystaceus, and Nysson spinosus, the latter cleptoparasite on Argogorytes wasps, have been analyzed by gas chromatography-mass spectrometry. The major compound in the mandibular gland secretion of the four species was tentatively identified as 2,5-dimethyl-3-isopentylpyrazine. A few other pyrazines not yet identified were also found. Preliminary tests withP. triangulum show that alkylpyrazines influence male behavior.
Key words Pyrazines - 2,5-dimethyl-3-isopentylpyrazine - marking volatiles - mandibular gland - philanthine wasp - nyssonine wasp - premating behavior - Hymenoptera - Sphecidae



This pheromone is very similar to the ant/chip compound discussed earlier in this thread.



[Edited on 26-7-2008 by Ritter]

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[*] posted on 26-7-2008 at 23:31


Quote:
Originally posted by Ritter
I found some references to pyrazine pheromones produced by ladybugs.

Quote:
Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs.

Cudjoe E, Wiederkehr TB, Brindle ID

Analyst 2005; 130:152-5.

Abstract
Static headspace sampling technique coupled with gas chromatography and mass spectrometry was used to investigate the presence of volatile 2-alkyl-3-methoxypyrazines in three different species of ladybugs of the Coccinellidae family. The species investigated were Coccinella septempunctata, Harmonia axyridis and Hippodemia convergens. 2-isopropyl-3-methoxypyrazine (IPMP) was identified in all three species with detectable levels of 2-sec-butyl-3-methoxypyrazine (SBMP) and 3-isobutyl-2-methoxypyrazines (IBMP) in only Hippodemia convergens and Harmonia axyridis species. Relative amounts of 2-alkyl-3-methoxypyrazines based on body mass showed that Hippodemia convergens had the highest levels of all three methoxypyrazines and Coccinella septempunctata the least.



These involve slightly different chemistry than the ant/chip pyrazines:



[Edited on 26-7-2008 by Ritter]


Thanks, great find!
Well, now how would these be made?
I'm guessing different amino acids or different sugars? I don't know the mechanism of the reaction, heck, I hardly know the reaction of how they form, so I wouldn't be able to predict what could form, but I bet you could make other pyrazine derivatives with other sugars.
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[*] posted on 27-7-2008 at 06:17


Quote:
Thanks, great find!
Well, now how would these be made?
I'm guessing different amino acids or different sugars? I don't know the mechanism of the reaction, heck, I hardly know the reaction of how they form, so I wouldn't be able to predict what could form, but I bet you could make other pyrazine derivatives with other sugars.


I don't believe the 2-alkoxy-3-alkylpyrazines can be made via the Maillard reaction. I suspect that they are either made by methylating 3-alkyl-2-pyrazinols or methoxylating 3-alkyl-2-halopyrazines. A quick search didn't come up with any clever ways to prepare these.

[Edited on 27-7-2008 by Ritter]




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[*] posted on 27-7-2008 at 07:15


Though producing the pure compound would interesting (if not fascinating) its a bit out of most of our reach. Perhaps we can instead cultivate methods of increasing of concentration of said scents in food like potato chips, starting with a few simple experiments and testing them with ants to see which is most attractive.

Unfortunately i am out of my lab for the summer :( .

Chemkid




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[*] posted on 27-7-2008 at 07:24


Quote:
Originally posted by chemkid
Though producing the pure compound would interesting (if not fascinating) its a bit out of most of our reach. Perhaps we can instead cultivate methods of increasing of concentration of said scents in food like potato chips, starting with a few simple experiments and testing them with ants to see which is most attractive.

Unfortunately i am out of my lab for the summer :( .

Chemkid


It would be nice if we could but a) the 2-methoxypyrazines do not result from the Maillard rxn AIAIK and b) the isopentyl pyrazine would require an apprpriately substituted amono acid for it to be formed in that rxn & that would be a major project in its own right.

Here are references on the synthesis of 2,5-dimethyl-3-isopentylpyrazine:

Quote:
Sato, N., and Matsuura, T. 1996. Studies on pyrazines. 31. Alkylation of chloropyrazine N-oxides by Nickel-catalyzed cross-coupling reaction with dialkylzincs. J. Heterocycl. Chem. 33:1047-10490.

Sato, N., and Matsuura, T. 1996. Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones. J. Chem. Soc. Perkin Trans. 1:2345-2350.




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