HK1042628A1 - Termite attractant and/or feeding stimulant - Google Patents
Termite attractant and/or feeding stimulant Download PDFInfo
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- HK1042628A1 HK1042628A1 HK02104481.6A HK02104481A HK1042628A1 HK 1042628 A1 HK1042628 A1 HK 1042628A1 HK 02104481 A HK02104481 A HK 02104481A HK 1042628 A1 HK1042628 A1 HK 1042628A1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
- A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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Abstract
A feeding stimulant for stimulating feeding activity in termites, comprising a compound having at least two OR groups, each of which is a substituent of an aryl moiety, and R is hydrogen or an organic group, and addition compounds thereof.
Description
Technical Field
The present invention relates to termite attractants and/or feeding stimulants, and more particularly to attractants and/or feeding stimulants for termite baits and as one of the components of a termite killing composition.
Background
Organic chlorine has been used for termite control for decades throughout the world, including australia. Since 1995 australia, and other countries, banned the use of organic chlorine to control termites at an earlier or similar time, efforts have been made to develop alternative termite control systems. Bait systems for controlling live termite infestation for such conditions have gradually been the primary control option.
Termites are provided in a bait system with a matrix that termites will preferentially feed on than other food sources suitable for the termite population. Termites either feed on long-lasting, non-repellant lethal products added to the food (matrix) or the termites that have gathered in the matrix are treated directly with such products. In both cases, the formulation is transferred to the nests by workers and distributed to the whole nest population by food exchange or mutual finishing between the termites.
Through extensive research conducted worldwide, it has now been recognized that what is being a bait toxin that is effective constitutes a major impediment to the use of baits, making it impossible to fundamentally guarantee the effective action of the bait system in practical applications. Bait-dependent control strategies must address the fact that termites have the ability to selectively feed and are unlikely to force insects into contact with the bait. Termites must first locate the bait stations and once a large number of termites are found to be attracted, a sufficient amount of toxin is transferred from the bait stations to the entire colony. Differences in termite behavior between termite species, between different populations within a species, and under different conditions at various locations potentially limit the effectiveness of such control strategies. The bait matrix currently used, which in most cases is only a pure cellulose product (wood, cardboard, paper), does not ensure a reliable and predictable way of contacting and aggregating termite populations.
Attempts have been made to increase the attractiveness of bait matrices to termites by adding attractant compounds. For example, international application WO99/07218 discloses the use of 2, 4-heptadienal as an attractant for social pests such as wasps and termites. U.S. patent 5,637,298 discloses 2-4 naphthalenemethanol derivatives substituted by methyl, ethyl, propyl or isopropyl groups at the 7 or 8 position of the naphthalene ring structure and indicates that these compounds improve termite acceptance for baits. Similarly, U.S. patent No. 5,756,114 discloses the incorporation of certain aromatic compounds, including dihydroxybenzoic acid, protecatechuic acid and vanillic acid, as bait odor attractants into bait on a substrate. These compounds are superficially similar to trackwork-pheromone (Z, Z, E) -3, 6, 8-dodecatrien-1-ol. Thus, they do not stimulate feeding behavior while promoting termite aggregation, and any increase in feeding is merely a result of an increase in the number of termites at the selected location.
Termites are social insects, and the social structure of a termite population depends largely on chemical signals present in the environment or produced by members of the population. These signals regulate various activities including foraging or social mining of food sources. For example, during feeding, termites release a chemical signal from the exocrine glands that directs the hive partner to feed at the location, thereby ensuring rapid and efficient exploitation of the food source.
All species of termites have pairs of lower labial glands located in the breast. The glandular tube is connected to the water sac glandular tube at the head, and the contents are secreted from the mouth in the form of saliva. The above secretions have been reported to have various functions according to different species and have been found in soldiers as a defensive substance, a regulator of microclimate in nests, a carrier of fungal reproduction in nests or as a social nutrient. In addition, the lower lip gland has been reported to secrete cementitious materials for building nests or constructing tunnels and was identified as a source of digestive enzymes.
Recently, Reinhard et al, Journal of Chemical Ecology, Vol.23No.10, 1997 concluded that labial gland secretions have a pheromonic role in food mining, and this may be a common phenomenon in termites. Reinhard et al removed the labial gland extract and used it in a feeding selection test. They observed that the lower labial gland secretions carried a signal during food extraction to stimulate workers to bite and eat. Even if no food is placed on the glass sheet, the lower labial gland extract can induce feeding behavior of termites. Testing with extracts of Reticulitermes santonensis and Alopecurus ostreatus (Schedorhinoptermes Camanians) confirmed feeding palatability signals in both termites. In view of the above, Reinhard et al suggested that the signaling function of food mining of lower lip gland secretions was ancient phylogenetic and not germ-line specific. Chemical signatures were now first identified and demonstrated to be potent feeding stimulants of a broad spectrum of termite species under natural low concentration conditions. In view of this, the class of compounds that stimulate termite feeding has been analyzed.
Disclosure of Invention
In a first aspect the present invention provides a feeding stimulant which stimulates feeding activity in termites, comprising a compound having at least two OR groups, each of which is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof.
The feeding stimulant may have feeding stimulating activity when it is a compound wherein at least one R is an organic group or a precursor of a compound having feeding stimulating activity.
In the former case, the organic group is preferably a group consisting of alkyl, substituted alkyl, aryl or substituted aryl, the latter case generally being a compound which can be hydrolysed to a compound having feeding stimulating activity, such as the compounds described above. Polymers or oligomers such as polyphenylene oxide gradually hydrolyze to compounds with feeding stimulating activity and can survive in the environment for extended periods of time.
The compounds having feeding stimulating activity generally comprise an aromatic nucleus substituted by at least two OR groups as defined above.
Typically, the compounds described above have the following general formula I:
wherein R is1Selected from the following groups: hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl；
R2，R3，R4，R5And R6Each independently selected from the group consisting of: hydrogen, hydroxy, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, aralkyl, substituted alkaryl, alkaryloxy and substituted alkaryloxy, or R2And R3Together, R3And R4Together, R4And R5Together and/or R5And R6Together form an aryl group;
provided that only R is2，R3，R4，R5Or R6At least one of which is a hydroxyl group, an alkoxy group, a substituted alkoxy group, an aryloxy group, a substituted aryloxy group, an alkaryloxy group or a substituted alkaryloxy group.
Preferably, R1Selected from the group consisting of hydrogen, alkyl, aryl and alkaryl.
More preferably, R1Selected from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl.
Still more preferably R1Is hydrogen.
Preferably, R2，R3，R4，R5And R6Each independently selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy, aryl, aryloxy, alkaryl, and alkaryloxy.
More preferably, R2，R3，R4，R5And R6Each independently selected from hydrogen, hydroxy, methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
Even more preferably, R2，R3，R4，R5Or R6At least one of which is a hydroxyl group. In particular, R2Or R6，R3Or R5Or R4In particular hydroxyl groups.
Particularly preferred compounds for use in the present invention are selected from the following compounds:
P-Hydroquinone (1, 4-dihydroxybenzene)
Pyrocatechol (1, 2-dihydroxy benzene)
Resorcinol (1, 3-dihydroxybenzene)
Phloroglucinol (1, 3, 5-trihydroxy benzene)
4-methoxyphenol
Methoxyhydroquinone (1-methoxy-2, 5-dihydroxybenzene)
1, 4-dimethoxybenzene
4-phenoxy phenol
Phenyl hydroquinone
4-Benzyloxyphenol
Also, addition compounds such as quinohydroquinone (an addition compound of 1 mole of hydroquinone to 1 mole of quinone) are included.
In other words, the compounds described above may carry multiple aryl moieties.
Preferably each of the aryl moieties described above is a benzene ring and the compound is a polyphenylene ether. Typically, polyphenylene ethers are ethers of p-hydroquinone with 2 to 5 p-hydroquinone residues.
The term "alkyl" as used throughout the specification and claims refers to straight or branched chain alkyl, preferably C1-C10Alkyl and more preferably C1-C4An alkyl group.
The term "substituted alkyl" as used throughout the specification and claims refers to alkyl substituted with any substituent, suitable substituents being hydroxy, alkoxy, carbonyl, carbonylalkyl, carbamoyl, ureido, amino, mono-or dialkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
The term "aryl" as used throughout this specification refers to a six-membered carbocyclic aromatic ring or a five-or six-membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulfur atoms as heteroatoms, and includes fused ring systems containing a plurality of the above rings.
The term "substituted aryl" as used throughout the specification and claims refers to aryl substituted with any substituent, suitable substituents being hydroxy, alkoxy, carbonyl, carbonylalkyl, carbamoyl, ureido, amino, mono-or dialkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
The term "alkoxy" as used throughout the specification and claims refers to a group containing straight or branched chain alkyl, preferably C1-C10Alkyl and more preferably C1-C4Alkoxy groups of alkyl groups.
The term "substituted alkoxy" as used throughout the specification and claims refers to alkoxy substituted with any substituent, suitable substituents being hydroxy, alkoxy, carbonyl, carbonylalkyl, carbamoyl, ureido, amino, mono-or dialkyl substituted amino, halo, alkylcarbonyloxy or alkylcarbonylamino.
The term "aryloxy" as used throughout the specification and claims refers to an aromatic ring containing a six-membered carbocyclic ring or an aromatic ring of a five-or six-membered heterocyclic ring containing 1, 2 or 3 oxygen, nitrogen or sulfur atoms as heteroatoms, as well as aryloxy groups comprising fused ring systems containing a plurality of the above rings.
The term "substituted aryloxy" as used throughout the specification and claims refers to aryloxy substituted with any substituent, suitable substituents being hydroxy, alkoxy, carbonyl, carbonylalkyl, carbamoyl, ureido, amino, mono-or dialkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
The term "alkaryl" as used throughout the specification and claims means containing a straight or branched chain alkylene group, preferably C1-C10Alkylene and more preferably C1-C4Alkylene radicals and aromatic rings of six-membered carbocyclic rings or containing 1, 2 or 3 oxygen, nitrogen or sulfur atomsAromatic rings of five-or six-membered heterocyclic rings as heteroatoms, and alkylaryl groups comprising condensed ring systems containing a plurality of the above rings.
The term "substituted alkylaryl" as used throughout the specification and claims refers to an alkylaryl group substituted with any substituent, suitable substituents being hydroxy, alkoxy, carboxy, carboxyalkyl, carbamoyl, ureido, amino, mono-or dialkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
The term "alkaryloxy" as used throughout the specification and claims refers to a compound containing a straight or branched chain alkyleneoxy group, preferably C1-C10Alkyleneoxy and more preferably C1-C4Alkyleneoxy groups and aromatic rings of six-membered carbocyclic rings or aromatic rings of five-or six-membered heterocyclic rings containing 1, 2 or 3 oxygen, nitrogen or sulfur atoms as heteroatoms, and alkaryloxy groups comprising condensed ring systems containing a plurality of the above-mentioned rings.
The term "substituted alkylaryloxy" as used throughout the specification and claims refers to an alkylaryloxy group substituted with any substituent, suitable substituents being hydroxy, alkoxy, carbonyl, carbonylalkyl, carbamoyl, ureido, amino, mono-or dialkyl-substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
The word "comprising" as used throughout the specification and claims is used in a non-exclusive sense unless otherwise indicated.
In a second aspect, the present invention provides a method of stimulating feeding activity in termites, comprising the steps of:
(1) providing a feeding stimulant as described above; and
(2) the feeding stimulant described above is applied to a designated site.
Preferably, a food source is present at the location.
A third aspect of the present invention provides a method of attracting termites to a designated site, comprising the steps of:
(1) a food source is provided at the location,
(2) providing a feeding stimulant as described above; and
(3) applying the feeding stimulant to the locus.
The compounds of formula I are useful as feeding stimulants and/or attractants for various termites, in particular, Australian darwiniensis (Mastotermes darwiniensis), Tripterospermum atratum (Coptotermes acinifermis), Kalottermes flaviolis, Sarcoptermes brevices (Cryptotermes brasiliensis), Gossampinus (Hodottermes sambucus), Melastoma esculentum (Zootes angusticis), Eurotiopsis lanceolatus (Reticulitermes flavipes), Reticulitermes ssonensis, Coptotermes xylostella (Heterotermes indicus), Peptotermes longus (Schizotermes lamanus), Coptotermes formosanus (Coptotermes forstericus), Naptotermes nigrus (Naptotermes nigrus), Naptotermes flavus terrestris and Maculopterus voroides.
The present invention provides, in a fourth aspect, a bait for attracting termites, comprising:
(1) a food source; and
(2) feeding stimulants as described above.
Typically the food source is a cellulosic derived material such as paper, cardboard, kainite, particleboard, and intact or fungally decayed wood. The compound of formula I is applied to the bait substrate by any suitable means, such as spraying a solution of the above compound onto the bait substrate, soaking the bait substrate in the above solution or mixing with a solid compound of formula I.
The bait matrix may also contain synergists and other attractants, as well as beneficial ingredients such as nitrogen compounds, carbohydrates, and the like as nutrients.
Antioxidants such as BHT, BHA or vitamin E may be added to stabilize the active compounds in the bait, if desired. If desired, controlled release systems for the compounds of formula I may be employed.
Preferably, the bait matrix includes supplemental toxins such as chitin synthesis inhibitors, insect growth regulators, and other termiticides. On the other hand, once the bait matrix is spread in the field and a large number of termites are attracted, the termiticide can be applied to the bait matrix. In another instance, it is preferred that the toxin be a long-acting and non-repellent agent to facilitate transfer of the formulation by workers to the nests and to distribute the formulation to the full nest population by food exchange or mutual finishing between the termites.
In a fifth aspect, the present invention provides a termite killing composition comprising:
(1) a termite-killing substance; and
(2) feeding stimulants as described above.
In a sixth aspect, the invention provides compounds having at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof, for use in stimulating feeding activity in termites.
In a seventh aspect of the invention, there are provided compounds bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof to attract termites to a given locus.
In an eighth aspect, the invention provides compounds bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety and R is hydrogen OR an organic group, and the use of adduct compounds thereof as termite feeding stimulating activity.
In a ninth aspect, the present invention provides the use of a compound bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof, to attract termites to a given locus.
In a tenth aspect, the present invention provides the use of a compound bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof, in the preparation of a bait for attracting termites.
In an eleventh aspect, the present invention provides the use of a compound bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof, for the preparation of a termiticidal composition.
Typically, the compound bearing at least two OR groups is a compound of formula I as described above.
Hydroquinone has been found to be a natural feeding stimulant, but hydroquinone present in the lower labial glands of termites is almost exclusively its glucose conjugate, 4-hydroxyphenyl- β -D-glucopyranoside, commonly known as β -arbutin. Glucose conjugates of beta-arbutin and other compounds of formula I may also be used in the above invention. In particular, glucose conjugates of beta-arbutin or other compounds of formula I may be added to the bait matrix and the active compounds of formula I produced by slow decomposition used in sustained release systems.
Best mode for carrying out the invention
Preferred embodiments of the present invention will now be described, by way of example only, with reference to the following examples.
Example 1-use of lower labial gland extract as Termite attractant
To prepare the lower labial gland extract, termites were killed and paired lower labial glands were removed. The labial glands were ruptured by freezing at-20 ℃ for 15 minutes and extracted with 0.6ml of water at room temperature for 12 hours. The extract is then frozen at-20 deg.C until use. The lower lip gland extracts prepared and tested are listed in table 1. Chemical analysis of each extract was performed to determine the presence or absence of p-hydroquinone, and as a result p-hydroquinone was found to be present in all extracts. Selected extracts were used in bioassays to assess feeding selectivity as shown in table 1 below.
Table 1: preparation of lower lip gland extract and chemical test biological test for testing termite glandular extraction
The article number Kalotermes flavicollis 40 + Sarcophyton 70 + + (Cryptotermes brevices) Dalbergia 30 + + (Mastotermes darwiniensis) Gomphytis 40 + (Hodotermes mossbiscus) ancient Bloo ants 40 + (Zootermomes angusticis) Europa 70 + + (Reticulitermes flavipes) Reticulitermes santonins 70 + + (Reticulitermes flavipes) Reticulitermes santonensis 70 + + Sarcophytomes heterotrime 120 + (Heterotomes indicus) Longipeditorella 60 + (Schizoetromes lanuginosus) Trastonitus formosanus 70 + (Coptotermes lanugensis) Subtipes sutent 70 + (Coptotermes forskotus Subtitus domesticus) Na+ (Coptotermes flavus nasutus 80 + (Coptotermes flavipes tristilex 40 + (Coptotermes flavipes tristilex latifolia) Subtitus + Tributicatus 40 + (Coptotermes flavipes terreus 80 + (Coptotermes tristilex latifolia 40 + (Coptoteres tristiles tristilex)
The method used in the selectivity test is the method used by Reinhard et al, supra. In these tests, termites were placed in suitable containers and passed through silicone tubes to foraging activity sites. Two semicircular pieces of wetted filter paper (2.5 cm in diameter) were placed close to each other in each test in the arena. One of two semicircular filter paper sheets was randomly selected, and a 25. mu.l aliquot of the lower labial gland extract was dropped thereon and then wetted with water. The other semicircular piece of filter paper was wetted with water only. Feeding by termites is expressed in gnawing behavior that is easily recognized by the position of the mouthed head, where the termites dig their jaws into the food and twist their heads to try to tear off a small piece of food before transporting it back to the nest.
The distribution of the first 20 biting/feeding termites on the semicircular piece of filter paper was recorded. For example, 19 of 20 dalveno australian termites were observed to respond, biting and eating the filter paper treated with 1 equivalent of their lower labial gland secretions, while only 1 termite responded to the control. Similarly, 18 of 20 Triplophora gondii responded, biting and eating the filter paper treated with 2.5 equivalents of its lower labial gland secretions, while only 2 termites responded to the control. Another important finding is that the termite species selected in the bioassay also responds strongly to the secretions from the lower labial glands of different species. For example, the test filters treated with 1 equivalent of the da e termite glandular secretions were reacted by the triathletes triallensis while the test filters treated with 2.5 equivalents of the da e termite glandular secretions were reacted by the da e termite. The above results demonstrate that the lower labial gland extract is a non-specific termite feeding stimulant. The results are summarized in table 2.
Table 2: the amount of the extract of origin of the extract of the lower lip glands of the termite species of the natural bait-responsive bait is responsive to the amount of the extract of origin of the extract
(equal gland)
The darwini termite, 1 + + + m.darwinienensis
Triptera ivory ant 2.5 + + +
C.acinaciformis
Opioptermes tritaefolia (L.) Kuntze 1 + + + C.Acincaciformes M.darwiniensis
Triptera ivory ant 2.5 + + +
C.acinaciformis
Analysis of the lower lip gland extract showed that hydroquinone was present at low concentrations, typically less than 10-10 grams per gland, but at higher concentrations in saliva. Beta-arbutin is present in high concentrations in glands, but is apparently not present in saliva. It is presumed that beta-arbutin is enzymatically decomposed into hydroquinone and glucose during salivary release from termites, and thus hydroquinone is assumed to be the main chemical feeding stimulant.
Example 2 Synthesis of Compounds as Termite attractants
Feeding selectivity tests were performed on hydroquinone and a number of related chemicals in the manner described above in example 1. The test data are summarized in table 3.
Table 3: synthetic bait
| Termite species responsive to bait | Compound (I) | Amount in bait | Reaction of |
| M.darwiniensis | Para-quinone | 5 | +++ |
| Quinone Hydroquinone | 5 | ++ | |
| Catechol | 5 | -/+ | |
| Resorcinol of intermediate content | 5 | + | |
| Phloroglucinol | 5 | -/+ | |
| 4-Methoxyphenol | 5 | + | |
| Methoxyhydroquinone | 5 | + | |
| 1, 4-dimethoxybenzene | 5 | ++ | |
| 4-phenoxy phenol | 5 | -/+ | |
| Phenyl hydroquinone | 5 | + | |
| Polyphenylene ether | 5 | + | |
| 4-Benzyloxol | 5 | -/+ | |
| C.acinaciformis | Para-hydroquinone | 5 | +++ |
| Quinone Hydroquinone | 5 | ++ | |
| Catechol | 5 | ++ | |
| Resorcinol | 5 | ++ | |
| Phloroglucinol | 5 | ++ | |
| 4-Methoxyphenol | 5 | + | |
| Methoxyhydroquinone | 5 | + | |
| 1, 4-dimethoxybenzene | 5 | + | |
| 4-phenoxy phenol | 5 | -/+ | |
| Phenyl hydroquinone | 5 | - | |
| Polyphenylene ether | 5 | - | |
| 4-Benzyloxol | 5 | - | |
| S.actuosus | Para-hydroquinone | 5 | +++ |
| C.brevis | Para-hydroquinone | 5 | +++ |
| N.exitiosus | Para-hydroquinone | 5 | +++ |
| R.santonensis | Para-hydroquinone | 5 | +++ |
| R.flavipes | Para-hydroquinone | 5 | +++ |
| C.formosanus | Para-hydroquinone | 5 | +++ |
The mixture includes pentamers of predominantly p-hydroquinone, but also dimers and trimers of p-hydroquinone as impurities.
When synthetic baits were tested, none of the major lower lip gland components (glucose, inositol, beta-arbutin) elicited any feeding stimulation response unless they could potentially act nutritionally as a food additive under non-natural high concentration conditions. However, in laboratory bioassays feeding stimuli can be elicited at natural trace levels to hydroquinone. For example, the minimum limit for attractant of Australian Coptotermes darwinia is 5 nanograms to hydroquinone (50 picomoles) and the minimum limit for attractant of Triplophora triceps is 100 picograms to hydroquinone (1 picomole). Therefore, the minimum value for feeding the stimulant varies among different kinds of termites.
As shown in table 3, synthetic compounds that have a somewhat similar molecular structure to hydroquinone in laboratory bioassays also induced feeding responses in australian termites darwinia and trifoliate termites.
Example 3 attracting mode
The attraction of hydroquinone sources to termites includes both olfactory and gustatory stimuli. The remote attractant capacity (olfaction) for hydroquinone was tested in empty and sand-filled plastic containers (14.5 cm internal diameter, 1cm high, covered with a glass slide) connected to a termite colony container by silicone tubing. The test was performed with Australian Termite, Dalbergia and Cochlolepis tergris. For each test, two pieces of treated filter paper (25 ng-25 μ g of hydroquinone and water, respectively, as controls) were placed in opposite positions on the indicated sites. And evaluating the direction of the tunnel/gallery built by the workers and the behavior thereof according to the position of the filter paper. The tunnels/tunnels constructed by both termites were oriented toward the hydroquinone-treated filter paper in all tests, and none were oriented toward the control filter paper. Termites usually walk slowly in a zig-zag fashion as they forage, but their behavior changes abruptly when approaching a source of hydroquinone (about 5-6 cm): they are straight and quickly crawl toward the treated filter paper sheet. From these observations we conclude that a "home zone" of a few centimeters is created for hydroquinone gas, once perceived, the termites are directed toward the source of gas created by the concentration gradient. This active zone is not enlarged by the increase in hydroquinone concentration.
Example 4 Selective feeding test
Test populations of solenopsis darwiniensis and triandra were tested in a selective feeding trial (simulating the actual bait form in the field) using Eucalyptus royal wood (eucalypus regnans) (approximately 3.5 g). Termite populations (approximately 500 dalbergia australis and 2000 campylobacter) were placed in plastic containers. A plastic arena 5cm in diameter and 3.5cm high was attached to the plexiglass tube on the opposite side of the termite population container. Providing wood in these arenas: one piece was 20ng of hydroquinone-treated wood dissolved in water, and the other piece was wetted with water only as a control. The wood was dried and weighed before and after the test, and the difference in weight due to termite feeding was analyzed after 3 days, 1 week and 4 weeks.
After 3 days and l weeks, the feeding amount of the solenopsis darussoides and the ivory termites on the wood treated with the feeding stimulant was significantly greater than that of the control (see table 4). The effect was lost after 4 weeks. Thus hydroquinone on choice does act as a feeding stimulant in the selective feeding trial, although only a very small amount of hydroquinone needs to be used and the effect is short-lived. This effect should be enhanced when the signal is tested under natural conditions and in the field where all termite populations are present.
Table 4: laboratory chow test of australian termites darwinia and koxifrage: comparing 20ng of hydroquinone treated wood with the control, the amount of wood consumed after 3 days, 1 week and 4 weeks [ g](mean ± sd, n ═ 20, Wilcoxon-Matched-Pairs-Test:significantdifference p < 0.001, n.s.: no significant difference).
| Seed of a plant | Duration of the test | Treated wood material to be eaten [ g ]] | Control wood to be eaten [ g ]] | p |
| M.darwiniensis | 3 days | 0.234±0.139 | O.121±0.108 | *** |
| 1 week | O.737±0.557 | 0.506±0.527 | ** | |
| 4 weeks | 2.397±0.968 | 2.255±O.918 | n.s. | |
| C.acinaciformis | 3 days | 0.056±0.0.36 | 0.032±0.033 | ** |
| 1 week | 0.185±0.159 | O.096±0.109 | ** | |
| 4 weeks | 1.162±0.851 | 1.209±O.929 | n.s. |
Example 5 field test
Coptotermes lacteus (ACT), Tripterodonta tricuspid (NT) and Durio darwiniensis (NT) populations were used for field large scale bait trials. Moreover, Coptotermes franchi (ACT), Nasutteries exitiosus (NSW), Schedorrhaters actasus (NT), Coptotermes fruvianass (Malaysia) and Coptotermes amantanus (Malaysia) were exemplarily tested in urban areas and in field infested locations. Approximately 10g of paper towel was used as the bait matrix. Tissues were treated with 20 μ g hydroquinone (dissolved in water) or wet with water only (control). The paper was folded and packed into plastic tubes. Termites enter the tubes through the bore holes to access the bait material. The treated baits and control baits were placed in field population feeding/infesting sites, respectively. In the case of larger field trials, up to 24 populations of each termite were selected and a wood-filled cylinder was dug into the soil surrounding the termite populations as a feeding site. Bait was placed on top of the infested cylinder and covered with plastic film and soil. In the exemplary experimental case a single infestation site was selected and the bait was directly contacted with the infestation and covered with plastic film and soil or cardboard to ensure minimal interference. The bait was checked after 1-4 days or after 2 weeks depending on the species and activity. The amount of paper fed and the number of termites were analyzed.
In nature, field populations also have large data variation among different populations, so the data must be converted into a logarithm and a square root for statistical analysis. In large-scale field trials, all c.lacteus, australian termites darwinia and thyreopsis were consuming significantly more bait material and a greater number of termites were attracted to the bait site when hydroquinone was used (see table 5). Exemplary tests conducted on new zealand lacto-termites, s.actuosus, south asian lacto-termites and opa japonicas showed that all termites had increased feeding activity on the treated baits compared to the control baits (see table 6). The test of exitiosus shows no feeding activity even after prolonged exposure to poison because of the different feeding habits of this species of termites. However, we still observed more termites present at the treated baits compared to the control baits (see table 6). We therefore concluded that hydroquinone, when added to bait, is also a potent and effective attractant and feeding stimulant for various termites in the field, in fact, under natural conditions.
Table 5: coptotermes lacteus (ACT), Tripterodonta tricuspid (NT) and Durio damascena field bait test. (W): the amount of poison bait (g) taken]And (No): number of termites { N) at the baits, 20 μ g of hydroquinone-treated baits were compared with control baits (mean ± standard deviation, paid Samples T-test,.: significant difference, p < 0.001, data scaled to log or square root for statistical analysis).
| Seed of a plant | Test of | N | Treated bait | Control bait | P | |
| C.lacteus | 3 days | 17 | W[g)No[N] | 0.392±0.156 | O.181±0.099 | *** |
| 269.7±169.1 | 198.9±147.7 | *** | ||||
| M.darwiniensis | 2 days | 12 | W[g]No[N] | O.766±0.164 | 0.368±O.126 | ** |
| 18.5±3.6 | 7.7±2.9 | ** | ||||
| C.acinaciformis | 2 days | 16 | W[g]No[N] | O.056±0.010 | 0.035±008 | ** |
| 120.6±29.5 | 84.1±20.0 | *** |
Table 6: exemplary field bait tests for lactotermes neozealand (ACT), schnorterinos actusus (NT), south asia lactotermes formosanus (Malaysia), amortis japonicus (Malaysia) and nasutiteresexitisus (nsw). The proportion of bait material consumed by each of 20 μ g of hydroquinone-treated bait compared to control bait [% ]]Or the number of termites present.
| Seed of a plant | Test of | Feeding rate/appearance of termites (bait treatment) | Feeding ratio/appearance of termites (control bait) | |
| C.frenchi | 2 weeks | 3 | 30％ | 5％ |
| 90％ | 0％ | |||
| 30％ | 0％ | |||
| S.actuosus | 4 days | 1 | 5％ | 0％ |
| C.travians | 1 day | 2 | 20％ | 20％ |
| 60％ | 40％ | |||
| C.curvignathus | 1 day | 3 | 95％ | 20％ |
| 50％ | 5％ | |||
| N.exitiosus | 2 weeks | 4 | ||
| Appearance of termites | Is not in touch with | |||
| Appearance of termites | Is not in touch with | |||
| Appearance of termites | Is not in touch with | |||
Industrial applicability
The compounds of the present invention are useful for stimulating termite feeding activity to enhance the termite killing effect of termite baits.
Claims (47)
1. A feeding stimulant that stimulates feeding activity in termites comprising a compound having at least two OR groups, each of which is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof.
2. The feeding stimulant of claim 1, wherein at least one R is an organic group and the compound has feeding stimulant activity.
3. The feeding stimulant of claim 2, wherein the organic group is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
4. The feeding stimulant of claim 1, wherein at least one R is an organic group and the compound is a precursor of a compound having feeding stimulant activity.
5. A feeding stimulant as claimed in claim 4 wherein the compound hydrolyses to a compound having at least one R being hydrogen.
6. A feeding stimulant as claimed in claim 5 wherein the organic group is a carbohydrate moiety.
7. The feeding stimulant of claim 6, wherein the compound is β -arbutin.
8. A feeding stimulant as claimed in claim 1 wherein said aryl group is an aromatic nucleus substituted by at least two of the above OR groups.
9. The feeding stimulant of claim 8, wherein the compound has the following general formula I:
wherein R is1Selected from the following groups: hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, and substituted aralkyl;
R2，R3，R4，R5and R6Each independently selected from the group consisting of: hydrogen, hydroxy, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, alkaryl, substituted alkaryl, alkaryloxy and substituted alkaryloxy, or R2And R3Together, R3And R4Together, R4And R5Together and/or R5And R6Together form an aryl group;
provided that only R is2，R3，R4，R5Or R6At least one of which is a hydroxyl group, an alkoxy group, a substituted alkoxy group, an aryloxy group, a substituted aryloxy group, an aralkyloxy group or a substituted aralkyloxy group.
10. The feeding stimulant of claim 9, wherein R1Selected from the group consisting of hydrogen, alkyl, aryl and aralkyl.
11. The feeding stimulant of claim 10, wherein R1Selected from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl.
12. The feeding stimulant of claim 11, wherein R1Is hydrogen.
13. The feeding stimulant of claim 9, wherein R2，R3，R4，R5And R6Each independently selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy, aryl, aryloxy, alkaryl, and alkaryloxy.
14. The feeding stimulant of claim 13, wherein R2，R3，R4，R5And R6Each independently selected from hydrogen, hydroxy, methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
15. The feeding stimulant of claim 14, wherein R2Or R6Is a hydroxyl group.
16. The feeding stimulant of claim 14, wherein R3Or R5Is a hydroxyl group.
17. The feeding stimulant of claim 14, wherein R4Is a hydroxyl group.
18. The feeding stimulant of claim 1, wherein the compound is selected from the group consisting of:
para-hydroquinone
Quinone Hydroquinone
Catechol
Resorcinol
Phloroglucinol
4-methoxyphenol
Methoxyhydroquinone
1, 4-dimethoxybenzene
4-phenoxy phenol
Phenyl hydroquinone
4-Benzyloxyphenol
19. A feeding stimulant as claimed in claim 1 wherein the compound carries multiple aryl moieties.
20. The feeding stimulant of claim 19, wherein each of said aryl moieties is a benzene ring.
21. A feeding stimulant as claimed in claim 20 wherein the compound is polyphenylene ether.
22. A feeding stimulant as claimed in any one of claims 1 to 21 further including a biologically acceptable carrier and/or supplement.
23. A method of stimulating feeding activity in termites, comprising the steps of:
(1) providing a feeding stimulant according to any one of claims 1 to 22; and
(2) the feeding stimulant described above is applied to a designated site.
24. The method of claim 23, further comprising the step of providing a food source in said location.
25. A method of attracting termites to a designated location, comprising the steps of:
(1) a food source is provided at the location,
(2) providing a feeding stimulant according to any one of claims 1 to 22; and
(3) applying the feeding stimulant to the locus.
26. A bait for attracting termites, comprising:
(1) a food source; and
(2) a feeding stimulant as claimed in any one of claims 1 to 22.
27. The bait of claim 26 wherein the food source is a cellulose-derived material.
28. The bait of claim 27, wherein the food source is selected from the group consisting of paper, cardboard, kainite (white), particleboard, and sound or fungally decayed wood.
29. The bait of any one of claims 26-28, further comprising a termiticide.
30. The bait of claim 29 wherein the termiticide is a chitin synthesis inhibitor or an insect growth regulator.
31. The bait of any one of claims 26 to 30, further comprising an antioxidant.
32. The bait of any one of claims 26 to 31, further comprising a potentiator and/or other attractant.
33. The bait of any one of claims 26 to 32, further comprising nutrients such as nitrogen containing compounds and carbohydrates.
34. A termite-killing composition comprising:
(1) a termite-killing substance; and
(2) a feeding stimulant as claimed in any one of claims 1 to 22.
35. The termiticide composition of claim 34, wherein the termiticide is a chitin synthesis inhibitor or an insect growth regulator.
36. A compound having at least two OR groups, wherein each OR group is a substituent of an aryl moiety and R is hydrogen OR an organic group, and adduct compounds thereof, are useful for stimulating feeding activity in termites.
37. A compound according to claim 36, which is a compound of formula I as defined in claim 9.
38. A compound having at least two OR groups, wherein each OR group is a substituent of an aryl moiety and R is hydrogen OR an organic group, and adduct compounds thereof, for use in attracting termites to a designated locus.
39. A compound according to claim 38, which is a compound of formula I as defined in claim 9.
40. Use of a compound having at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and adduct compounds thereof, for stimulating feeding activity in termites.
41. Use of a compound according to claim 40, wherein the compound is of formula I as defined in claim 9.
42. Compounds bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and their use as adduct compounds for attracting termites to a designated locus.
43. Use of a compound according to claim 42, wherein the compound is of formula I as defined in claim 9.
44. A compound having at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and the use of adduct compounds thereof in the preparation of termite attracting baits.
45. Use of a compound according to claim 44, wherein the compound is of general formula I as defined in claim 9.
46. Compounds bearing at least two OR groups, wherein each OR group is a substituent of an aryl moiety, and R is hydrogen OR an organic group, and their use in the preparation of a termiticidal composition.
47. Use of a compound according to claim 46, wherein the compound is of formula I as defined in claim 9.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPP7842A AUPP784298A0 (en) | 1998-12-22 | 1998-12-22 | Termite attractant and/or feeding stimulant compounds |
| AUPP7842 | 1998-12-22 | ||
| PCT/AU1999/001033 WO2000036914A1 (en) | 1998-12-22 | 1999-11-25 | Termite attractant and/or feeding stimulant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HK1042628A1 true HK1042628A1 (en) | 2002-08-23 |
Family
ID=3812046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HK02104481.6A HK1042628A1 (en) | 1998-12-22 | 1999-11-25 | Termite attractant and/or feeding stimulant |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1139742A4 (en) |
| JP (1) | JP2002532519A (en) |
| CN (1) | CN1337849A (en) |
| AP (1) | AP2001002190A0 (en) |
| AU (1) | AUPP784298A0 (en) |
| BR (1) | BR9916480A (en) |
| HK (1) | HK1042628A1 (en) |
| ID (1) | ID29807A (en) |
| OA (1) | OA11814A (en) |
| WO (1) | WO2000036914A1 (en) |
| ZA (1) | ZA200105010B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6978572B1 (en) | 1998-11-06 | 2005-12-27 | Colorado State University Research Foundation | Method and device for attracting insects |
| US7030156B2 (en) | 2001-03-05 | 2006-04-18 | University Of Florida Research Foundation, Inc | Devices and methods for eliminating termite colonies |
| US6716421B2 (en) | 2001-03-05 | 2004-04-06 | University Of Florida Research Foundation, Inc. | Devices and methods for eliminating termite colonies |
| US6969512B2 (en) | 2001-03-05 | 2005-11-29 | The University Of Florida Research Foundation, Inc. | Devices and methods for eliminating termite colonies |
| CN103039451B (en) * | 2012-12-21 | 2015-03-18 | 广东省农业科学院植物保护研究所 | Powder type blattaria bait |
| WO2017160995A1 (en) * | 2016-03-16 | 2017-09-21 | Roger Laine | Cyclohexylamine-based compounds and uses thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190667B (en) * | 1982-01-22 | 1988-02-24 | Montedison Spa | METHOD FOR COMBATING ANTI INFESTATION |
| JPS58157703A (en) * | 1982-03-11 | 1983-09-19 | Takeda Chem Ind Ltd | Controlling agent against termite |
| JPS6456606A (en) * | 1987-08-27 | 1989-03-03 | Tohoku Kako Kk | Ant-proofing agent |
| US4880624A (en) * | 1988-03-18 | 1989-11-14 | The Board Of Trustees Of The University Of Illinois | Volatile attractants for diabrotica species |
| JP2745331B2 (en) * | 1989-09-27 | 1998-04-28 | 日東電工株式会社 | Termite detection material |
| JPH05255007A (en) * | 1992-03-17 | 1993-10-05 | Tofti Gmbh | Natural or equivalent nontoxic formulation for exterminating ant, termite or analogous insect |
| DE4231045A1 (en) * | 1992-09-17 | 1994-03-24 | Desowag Materialschutz Gmbh | Compsns for termite control in soil - comprise phenol deriv, e.g. eugenol, terpene and carrier |
| US5780515A (en) * | 1996-03-21 | 1998-07-14 | Rockhurst University | Benzoquinone and hydroquinone derivatives for use as insect feeding deterrents |
-
1998
- 1998-12-22 AU AUPP7842A patent/AUPP784298A0/en not_active Abandoned
-
1999
- 1999-11-25 BR BR9916480-9A patent/BR9916480A/en not_active IP Right Cessation
- 1999-11-25 ID IDW00200101607A patent/ID29807A/en unknown
- 1999-11-25 OA OA1200100159A patent/OA11814A/en unknown
- 1999-11-25 HK HK02104481.6A patent/HK1042628A1/en unknown
- 1999-11-25 AP APAP/P/2001/002190A patent/AP2001002190A0/en unknown
- 1999-11-25 CN CN99816317A patent/CN1337849A/en active Pending
- 1999-11-25 WO PCT/AU1999/001033 patent/WO2000036914A1/en not_active Ceased
- 1999-11-25 EP EP99957752A patent/EP1139742A4/en not_active Withdrawn
- 1999-11-25 JP JP2000589037A patent/JP2002532519A/en not_active Withdrawn
-
2001
- 2001-06-19 ZA ZA200105010A patent/ZA200105010B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1337849A (en) | 2002-02-27 |
| ZA200105010B (en) | 2002-06-19 |
| AUPP784298A0 (en) | 1999-01-21 |
| JP2002532519A (en) | 2002-10-02 |
| OA11814A (en) | 2005-08-16 |
| WO2000036914A1 (en) | 2000-06-29 |
| EP1139742A4 (en) | 2002-07-31 |
| ID29807A (en) | 2001-10-11 |
| EP1139742A1 (en) | 2001-10-10 |
| BR9916480A (en) | 2002-01-15 |
| AP2001002190A0 (en) | 2001-05-25 |
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