WO2000036914A1 - Termite attractant and/or feeding stimulant - Google Patents

Termite attractant and/or feeding stimulant Download PDF

Info

Publication number
WO2000036914A1
WO2000036914A1 PCT/AU1999/001033 AU9901033W WO0036914A1 WO 2000036914 A1 WO2000036914 A1 WO 2000036914A1 AU 9901033 W AU9901033 W AU 9901033W WO 0036914 A1 WO0036914 A1 WO 0036914A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
feeding
feeding stimulant
substituted
hydrogen
Prior art date
Application number
PCT/AU1999/001033
Other languages
French (fr)
Inventor
Judith Reinhard
Michael James Lacey
Michael Lenz
Original Assignee
Commonwealth Scientific And Industrial Research Organisation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Commonwealth Scientific And Industrial Research Organisation filed Critical Commonwealth Scientific And Industrial Research Organisation
Priority to JP2000589037A priority Critical patent/JP2002532519A/en
Priority to BR9916480-9A priority patent/BR9916480A/en
Priority to AU15374/00A priority patent/AU762004B2/en
Priority to APAP/P/2001/002190A priority patent/AP2001002190A0/en
Priority to EP99957752A priority patent/EP1139742A4/en
Publication of WO2000036914A1 publication Critical patent/WO2000036914A1/en
Priority to HK02104481.6A priority patent/HK1042628A1/en

Links

Classifications

    • 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
    • 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

Definitions

  • the present invention is concerned with attractants and/or feeding stimulants for termites and, more particularly, with attractants and/or feeding stimulants for use in termite baits and as a component of termiticidal compositions .
  • Organochlorines have underpinned termite control around the world including in Australia, for many decades. With the ban on the use of organochlorines for termite control in Australia since 1995 and earlier or at similar times in other countries, increasing efforts are being mounted to develop alternative termite management systems. Bait systems for the control of active termite infestations are considered increasingly the key management option for such situations.
  • termites are offered a matrix on which the insects ought to feed in preference to other food sources available to a termite colony. Termites either take up a slow-acting, non-repellent lethal product which is incorporated into the food (matrix) or the termites which aggregate in the matrix are directly treated with such a product.
  • 5,756,114 describes the incorporation of certain aromatic compounds including resorcylic acid, protecatechuic acid and vanillic acid into baits on the basis that they act as food odour attractants. These compounds apparently mimic the trail-marking pheromone [ Z, Z, E) -3 , 6 , 8-dodecatrien-l-ol . Thus, while they promote termite aggregation they do not necessarily stimulate feeding behaviour, and any increased feeding may be a consequence only of the increased numbers of termites at a selected site.
  • Termites are social insects and the social organisation of termite colonies largely depends on chemical signals present in the environment or produced by members of the colony. These signals modulate a variety of behaviours including foraging for food or communal exploitation of a food source. For example, during feeding, termites release a chemical signal from an exocrine gland that stimulates nest mates to feed at the same site, thereby ensuring a rapid and efficient exploitation of the food source.
  • 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 .
  • the feeding stimulant is a compound in which at least one R is an organic group it may have feeding stimulating activity or may be a pre-cursor of a compound with feeding stimulating activity.
  • the organic group is preferably selected from the group consisting of alkyl , substituted alkyl, aryl or substituted aryl, and in the latter case is typically a compound which is hydrolysed to one having feeding stimulating activity, such as those in which the organic group is a carbohydrate moiety.
  • ⁇ -Arbutin is one such compound.
  • Polymers or oligomers such as polyphenylethers , as well as being long-lived in the environment, will progressively hydrolyse to compounds having feeding stimulating activity.
  • Compounds having feeding stimulating activity typically have an aromatic nucleus substituted by said at least two OR groups.
  • Ri is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, and substituted aralkyl;
  • R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, hydroxyl , alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, alkaryl, substituted alkaryl, alkaryloxy and substituted alkaryloxy, or R 2 and R 3 together, R 3 and R 4 together, R 4 and R 5 together and/or R 5 and R ⁇ together form an aryl group; provided only that at least one of R 2 , R 3 , R 4 , R5 or R 6 is hydroxyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkaryloxy or substituted alkaryloxy.
  • R x is selected from the group consisting of hydrogen, alkyl, aryl and alkaryl. More preferably, Ri is selected from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl. More preferably still, R x is hydrogen.
  • R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, alkoxy, aryl, aryloxy, alkaryl, and alkaryloxy.
  • R , R 3 , R 4 , R5 and R 6 are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
  • R 2; R 3 , R , R5 or R 6 is hydroxyl.
  • R 2 or Re, R3 or R 5 or R is typically hydroxyl .
  • Particularly preferred compounds for use in the present invention are selected from the group consisting of: p-hydroquinone ( 1 , 4-dihydroxybenzene) catechol ( 1 , 2-dihydroxybenzene) resorcinol ( 1 , 3-diahydroxybenzene) phloroglucinol (1,3, 5-trihydroxybenzene)
  • addition compounds such as quinhydrone (an addition compound of 1 mole hydroquinone and 1 mole quinone) are also envisaged.
  • said compound may have a plurality of aryl moieties .
  • each said aryl moiety is a benzene ring and the compound is a polyphenylether.
  • the polyphenylether is an ether of p-hydroquinone having between 2 and 5 p-hydroquinone residues.
  • composition may further comprise a biologically acceptable carrier and/or extender.
  • alkyl refers to straight or branched chain alkyl radicals, preferably C ⁇ -C ⁇ o alkyl radicals and, more preferably, C ⁇ _C alkyl radicals.
  • substituted alkyl refers to an alkyl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl , carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino .
  • aryl 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 sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings .
  • substituted aryl refers to an aryl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
  • alkoxy refers to an alkoxy radical containing a straight or branched chain alkyl radicals, preferably Ci-Cio alkyl radicals and, more preferably, C ⁇ _C alkyl radicals.
  • substituted alkoxy refers to an alkoxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino .
  • aryloxy refers to an aryloxy radical containing a six-membered carbocyclic aromatic ring or a five- or six- membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings .
  • substituted aryloxy refers to an aryloxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino .
  • alkaryl refers to an alkaryl radical comprising a straight or branched chain alkylene radical, preferably a Ci-Cio alkylene radical and, more preferably, a C ⁇ -C alkylene radical and a six-membered carbocyclic aromatic ring or a five- or six-membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings.
  • substituted alkaryl refers to an alkaryl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
  • alkaryloxy refers to an alkaryloxy radical containing a straight or branched chain alkyleneoxy group, preferably a Ci-Cio alkyleneoxy group and, more preferably, C1-C 4 alkyleneoxy group, and a six-membered carbocyclic aromatic ring or a five- or six-membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings.
  • substituted alkaryloxy refers to an alkaryloxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
  • a feeding stimulant as described above ; and (2) applying said feeding stimulant to a locus.
  • a food source at said locus.
  • a method of attracting termites to a locus comprising the steps of: (1) providing a food source at said locus,
  • the compounds of general formula I act as a feeding stimulant and/or attractant to termite species, in particular, to Mastoter es darwiniensis , Coptotermes acinaciformis , Kalotermes flavicollis, Cryptotermes brevis, Hodotermes mossambicus , Zootermopsis angusticollis , Reticuli termes flavipes , Reticuli termes santonensis ,
  • Coptotermes formosanus Nasuti termes nigriceps .
  • Nasuti termes exi tiosus Trinervi termes trinervoides and Macrotermes subhyalinus .
  • a bait for attracting termites comprising:
  • the food source is a source of cellulose such as paper, cardboard, canite, chipboard, and sound or fungally decayed wood.
  • the compound of general formula I is applied to the bait matrix in any convenient manner, such as by spraying a solution of the compound on the bait matrix, soaking the bait matrix in such a solution or by admixture with a solid compound of general formula I.
  • the bait matrix may also contain synergists and other attractants, as well as beneficial components such as nitrogen-containing compounds, carbohydrates and the like as nutrients .
  • antioxidants such as BHT, BHA or tocopherols may be added to stabilise the active compound within the bait.
  • a controlled release system for the compound of general formula I may be employed where desirable .
  • the bait matrix includes added toxins such as chitin synthesis inhibitors, insect growth regulators and other termiticides .
  • termiticidal substances can be applied to the bait matrix once it has been deployed in the field and has attracted a significant number of termites.
  • the toxin be slow-acting and non-repellent so as to be transported into the nest by foragers and there distributed throughout the colony either via food exchange or mutual grooming between the nest mates.
  • a ter iticidal composition comprising:
  • a feeding stimulant as described above.
  • a seventh aspect of the present invention there is provided 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, when used to attract termites to a locus.
  • 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, in stimulating feeding activity in termites .
  • 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, in attracting termites to a locus.
  • a compound in the manufacture of a bait for attracting termites said 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 .
  • a compound in the manufacture of a termiticidal composition said 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.
  • the compound having at least two OR groups is a compound of general formula I as described above.
  • para-hydroquinone is the natural feeding stimulant, but exists in the labial glands of termites almost entirely as its glucose conjugate, 4- hydroxyphenyl- ⁇ -D-glucopyranoside, which is commonly called ⁇ -arbutin.
  • ⁇ -Arbutin and glucose conjugates of the other compounds of general formula I may also be used in the invention described above.
  • ⁇ -arbutm or glucose conjugates of the other compounds of formula I can be incorporated into a bait matrix and, through slow decay generating an active compound of general formula I, could act as a slow-release system.
  • Example 1 Use of Labial Glands Extracts as Termite Attractants
  • termites were killed and the paired labial glands were removed.
  • the labial glands were disrupted by freezing them for 15 minutes at -20°C and extracted with 0.6 ml of water for 12 hours at room temperature. Then the extract was frozen at -20°C until used.
  • the labial gland extracts prepared and tested are listed m Table I. Each extract was chemically analysed for the presence of para-hydroquinone, and it was found to be present m all. Selected extracts were used in a bioassay to establish feeding choice, as indicated in Table 1, below.
  • Kalotermes flavicollis 40 Cryptotermes brevis 70 + + Mastotermes darwimensis 30 + + Hodotermes mossambicus 40 + Zootermopsis angus ti collis 40 + Reticul i termes flavipes 70 + + Reticuli termes san tonensis 70 + + Heterotermes indicola 120 + Schedorhmoter es la anianus 60 + Coptotermes formosanus 70 + + Coptotermes acinaci formis 80 + + Nasu ti termes mgriceps 60 + Nasu ti termes exi tiosus 70 + + Trmervi termes trmervoides 30 + Macrotermes subhyalmus 40 +
  • Feeding in termites is expressed by gnawing behaviour, which can be easily recognised by the hypognathous head positions wherein the termites bore their mandibles into the food and wriggle their heads trying to tear off little pieces, which they can then transport back to the nest.
  • the distribution of the first 20 gnawing/ feeding termites on the semicircles was registered. For example, it was observed that 19 of 20 Mas totermes darwini ensis termites responded by gnawing and eating the filter paper treated with one equivalent of its labial gland secretion while only one termite responded to the control. Similarly, 18 of 20 C. acinaciformis termites responded by gnawing and eating the filter paper treated with 2.5 equivalents of its labial gland secretion while 2 responded to the control . A further important observation was that termites of selected species also responded strongly in the bioassay to labial gland secretion from an unrelated species. For instance, C. acinaciformis termites responded to a test paper treated with one equivalent of M.
  • Example 2 Synthetic Compounds as Termite Attractants Feeding choice tests were conducted with para- hydroquinone and a number of related chemical substances in the manner described above in Example 1. The experimental data is summarised in Table 3.
  • Synthetic compounds somewhat related in molecular structure to hydroquinone also elicited feeding responses from M. darwiniensis and C. acinaciformis in the laboratory bioassays, as shown in Table 3.
  • the mode of attraction of termites to the para- hydroquinone source may well include both olfactory and gustatory stimulation.
  • the attractivity of para- hydroquinone over distance was tested both in empty and sand-filled plastic arenas (ID 14.5 cm, height 1 cm, covered with a glass plate), which were attached via a silicone tube to the housing container of the termites.
  • Tests were carried out with M. darwiniensis and C. acinaciformis .
  • two treated filter papers 25ng - 25 ⁇ g p-hydroquinone and water as control, respectively) were placed in opposite positions in the arenas. The direction of the tunnel/galleries built and the behaviour of a foraging termites in reference to the position of the filter papers were evaluated.
  • Example 4 Choice Feeding Tests Laboratory colonies of Mastotermes darwiniensis and Coptotermes acinaciformis have been tested in a choice feeding test (mimicking an actual bait situation in the field) with pieces of Eucalyptus regnans wood (ca. 3.5g) .
  • the colonies (ca. 500 termites in M. darwiniensis , 2000 termites in C. acinaciformis) were housed in plastic containers.
  • Plastic arenas of 5cm diameter, 3.5cm high were attached with perspex tubes on opposite sides of the colony container. In these arenas the wood was offered: one treated with 20ng p-hydroquinone, dissolved in water, the other just moistened as control. The wood was dried and weighed before and after the test, the difference in weight as the amount eaten by termites was analysed after 3 days , 1 week and 4 weeks .
  • Coptotermes travians (Malaysia) and Copto termes curvigna thus (Malaysia) have been tested exemplarily at infestation sites in urban areas and in the field.
  • the paper was folded and stuffed in plastic tubes. Termites had access to the bait material through holes drilled into the tubes .
  • One treated and one control bait each were placed at feeding/infestation sites of the field colonies. In case of the larger field trials, up to 24 colonies per species had been selected, and drums filled with wood had been dug into the soil around colonies as feeding sites.
  • Baits were placed on top of the infested drums and covered with plastic foil and soil. In case of the exemplary trials single infestation sites have been selected and the baits were attached directly onto the infestation and covered with plastic foil and soil, or cardboard to ensure minimum disturbance. Baits were checked after 1 to 4 days or after 2 weeks, depending on species and activity. The amount of paper eaten and the number of termites were analysed.
  • Table 6 Exemplary field baiting trials with Coptotermes frenchi (ACT) , Schedorhinotermes actuosus (NT) , Coptotermes travians (Malaysia) , Coptotermes curvigna thus (Malaysia) and Nasuti termes exi tiosus (NSW) .
  • the compounds of the present invention are useful in stimulating feeding activity in termites so as to enhance the effectiveness of termite baits .

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Food Science & Technology (AREA)
  • Toxicology (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

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

TERMITE ATTRACTANT AND/OR FEEDING STIMULANT
TECHNICAL FIELD
The present invention is concerned with attractants and/or feeding stimulants for termites and, more particularly, with attractants and/or feeding stimulants for use in termite baits and as a component of termiticidal compositions .
BACKGROUND ART
Organochlorines have underpinned termite control around the world including in Australia, for many decades. With the ban on the use of organochlorines for termite control in Australia since 1995 and earlier or at similar times in other countries, increasing efforts are being mounted to develop alternative termite management systems. Bait systems for the control of active termite infestations are considered increasingly the key management option for such situations. In bait systems termites are offered a matrix on which the insects ought to feed in preference to other food sources available to a termite colony. Termites either take up a slow-acting, non-repellent lethal product which is incorporated into the food (matrix) or the termites which aggregate in the matrix are directly treated with such a product. In both scenarios the agent is transported into the nest by the foragers and there distributed throughout the colony either via food exchange or mutual grooming between nest mates. Following considerable research around the world there is now a growing awareness that just finding an effective bait toxin, initially thought to be the main impediment to the application of baits, is no guarantee at all that a bait system will work effectively in practice. Control strategies relying on baits have to cope with the fact that termites have a choice and that the insects cannot be forced to make contact with the baits . Termites have to be able to locate a bait station in the first place, and once it is found, be attracted to it in significant numbers so that adequate transfer of the toxin from the bait site to the colony can occur. Differences in behaviour between species of termite, between colonies within a species and between conditions at various sites potentially restrict the effectiveness of this control strategy. Currently used bait matrices, in most cases just straight cellulose products (timber, cardboard, paper), do not necessarily ensure contact and build up of termite numbers in bait stations in a reliable, predictable fashion.
Attempts have been made to enhance the attraction of termites to bait matrices through the addition of attractant compounds. For example, International Application WO99/07218 describes the use of 2,4 heptadienal as an attractant for social pest insects such as wasps and termites. United States Patent No. 5,637,298 describes 2-4 naphthalenemethanol derivative substituted at the 7 or 8 position of the naphthalene ring structure by methyl, ethyl, propyl or isopropyl, and indicates that these compounds increase bait acceptance by termites. Likewise, United States Patent No. 5,756,114 describes the incorporation of certain aromatic compounds including resorcylic acid, protecatechuic acid and vanillic acid into baits on the basis that they act as food odour attractants. These compounds apparently mimic the trail-marking pheromone [ Z, Z, E) -3 , 6 , 8-dodecatrien-l-ol . Thus, while they promote termite aggregation they do not necessarily stimulate feeding behaviour, and any increased feeding may be a consequence only of the increased numbers of termites at a selected site.
Termites are social insects and the social organisation of termite colonies largely depends on chemical signals present in the environment or produced by members of the colony. These signals modulate a variety of behaviours including foraging for food or communal exploitation of a food source. For example, during feeding, termites release a chemical signal from an exocrine gland that stimulates nest mates to feed at the same site, thereby ensuring a rapid and efficient exploitation of the food source.
All species of termite have paired labial glands located in the thorax. The glandular ducts join in the head with those of the water sacs and the contents are secreted from the mouth as saliva. This secretion has been reported to have various functions depending on the species, and has variously been identified as a defensive substance in soldier termites, a regulator of nest microclimate, a supporter of fungal cultivation in the nest or as a social nutrient. In addition, the labial glands have been said to secrete a cementing substance for nest construction or gallery building and have been identified as a source of digestive enzymes. More recently, Reinhard et al . , Journal of Chemical Ecology, Vol . 23 No . 10, 1997 concluded that the labial gland secretion may play a pheromonal role during food exploitation, and that this might be a general phenomenon in termites. Reinhard et al . took labial gland extracts and used these in feeding choice tests. They observed that the labial gland secretion carries a signal that stimulates gnawing and feeding by termite workers during food exploitation. The extract of the labial gland even elicited feeding behaviour when applied without food onto glass plates. These extracts were tested with both Reticuli termes santonensls and Schedorhinotermes lamanianus and proved to elicit a significant feeding preference in the two species. In view of this, Reinhard et al . suggested that the signal function of the labial gland secretion for food exploitation is phylogenetically old and non-species specific. The chemical signal has now been identified for the first time and has proved to work as a powerful feeding stimulant at natural low concentrations on a wide range of termite species. In view of this a class of compounds which stimulate termite feeding has been identified.
DISCLOSURE OF THE INVENTION
According to a first aspect of the present invention there is provided 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 .
Where the feeding stimulant is a compound in which at least one R is an organic group it may have feeding stimulating activity or may be a pre-cursor of a compound with feeding stimulating activity.
In the former case, the organic group is preferably selected from the group consisting of alkyl , substituted alkyl, aryl or substituted aryl, and in the latter case is typically a compound which is hydrolysed to one having feeding stimulating activity, such as those in which the organic group is a carbohydrate moiety. β-Arbutin is one such compound. Polymers or oligomers such as polyphenylethers , as well as being long-lived in the environment, will progressively hydrolyse to compounds having feeding stimulating activity.
Compounds having feeding stimulating activity typically have an aromatic nucleus substituted by said at least two OR groups.
Typically such compounds have the following general formula I :
Figure imgf000007_0001
wherein Ri is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, and substituted aralkyl;
R2, R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, hydroxyl , alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, alkaryl, substituted alkaryl, alkaryloxy and substituted alkaryloxy, or R2 and R3 together, R3 and R4 together, R4 and R5 together and/or R5 and Rζ together form an aryl group; provided only that at least one of R2 , R3 , R4 , R5 or R6 is hydroxyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkaryloxy or substituted alkaryloxy.
Preferably, Rx is selected from the group consisting of hydrogen, alkyl, aryl and alkaryl. More preferably, Ri is selected from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl. More preferably still, Rx is hydrogen. Preferably, R2 , R3 , R4, R5 and R6 are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, alkoxy, aryl, aryloxy, alkaryl, and alkaryloxy.
More preferably, R , R3 , R4, R5 and R6 are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
More preferably still, at least one of R2; R3 , R , R5 or R6 is hydroxyl. In particular, R2 or Re, R3 or R5 or R is typically hydroxyl . Particularly preferred compounds for use in the present invention are selected from the group consisting of: p-hydroquinone ( 1 , 4-dihydroxybenzene) catechol ( 1 , 2-dihydroxybenzene) resorcinol ( 1 , 3-diahydroxybenzene) phloroglucinol (1,3, 5-trihydroxybenzene)
4-methoxyphenol methoxyhydroquinone (l-methoxy-2 , 5-dihydroxybenzene)
1, 4-dimethoxybenzene 4-phenoxyphenol phenylhydroquinone
4-benzyloxyphenol
Moreover, addition compounds such as quinhydrone (an addition compound of 1 mole hydroquinone and 1 mole quinone) are also envisaged.
Alternatively, said compound may have a plurality of aryl moieties .
Preferably each said aryl moiety is a benzene ring and the compound is a polyphenylether. Typically, the polyphenylether is an ether of p-hydroquinone having between 2 and 5 p-hydroquinone residues.
The composition may further comprise a biologically acceptable carrier and/or extender. As used throughout the specification and claims the term "alkyl" refers to straight or branched chain alkyl radicals, preferably Cχ-Cιo alkyl radicals and, more preferably, Cι_C alkyl radicals. As used throughout the specification and claims the term "substituted alkyl" refers to an alkyl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl , carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino .
As used throughout the specification the term "aryl" 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 sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings .
As used throughout the specification and claims the term "substituted aryl" refers to an aryl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
As used throughout the specification and claims the term "alkoxy" refers to an alkoxy radical containing a straight or branched chain alkyl radicals, preferably Ci-Cio alkyl radicals and, more preferably, Cι_C alkyl radicals.
As used throughout the specification and claims the term "substituted alkoxy" refers to an alkoxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino . As used throughout the specification and claims the term "aryloxy" refers to an aryloxy radical containing a six-membered carbocyclic aromatic ring or a five- or six- membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings .
As used throughout the specification and claims the term "substituted aryloxy" refers to an aryloxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino .
As used throughout the specification and claims the term "alkaryl" refers to an alkaryl radical comprising a straight or branched chain alkylene radical, preferably a Ci-Cio alkylene radical and, more preferably, a Cι-C alkylene radical and a six-membered carbocyclic aromatic ring or a five- or six-membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings.
As used throughout the specification and claims the term "substituted alkaryl" refers to an alkaryl radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
As used throughout the specification and claims the term "alkaryloxy" refers to an alkaryloxy radical containing a straight or branched chain alkyleneoxy group, preferably a Ci-Cio alkyleneoxy group and, more preferably, C1-C4 alkyleneoxy group, and a six-membered carbocyclic aromatic ring or a five- or six-membered heterocyclic aromatic ring containing 1, 2 or 3 oxygen, nitrogen or sulphur atoms as the heteroatom, and includes fused ring systems containing a plurality of such rings. As used throughout the specification and claims the term "substituted alkaryloxy" refers to an alkaryloxy radical substituted by any substituent, conveniently, by hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl, carbamido, amino, mono- or di- alkyl substituted amino, halogen, alkylcarbonyloxy or alkylcarbonylamino.
As used throughout the specification and claims, the words "comprise", "comprises" and "comprising" are used in a non-exclusive sense, except where the context requires otherwise. According to a second aspect of the present invention there is provided a method of stimulating feeding activity in termites, comprising the steps of:
(1) providing a feeding stimulant as described above ; and (2) applying said feeding stimulant to a locus. Preferably, there is a food source at said locus. According to a third aspect of the present invention there is provided a method of attracting termites to a locus, comprising the steps of: (1) providing a food source at said locus,
(2) providing a feeding stimulant as described above ; and
(3) applying said feeding stimulant to said locus. The compounds of general formula I act as a feeding stimulant and/or attractant to termite species, in particular, to Mastoter es darwiniensis , Coptotermes acinaciformis , Kalotermes flavicollis, Cryptotermes brevis, Hodotermes mossambicus , Zootermopsis angusticollis , Reticuli termes flavipes , Reticuli termes santonensis ,
Heterotermes indicola, Schedorhinotermes lamanianus ,
Coptotermes formosanus , Nasuti termes nigriceps ,
Nasuti termes exi tiosus , Trinervi termes trinervoides and Macrotermes subhyalinus .
According to a fourth aspect of the present invention there is provided a bait for attracting termites, comprising :
(1) a food source; and (2) a feeding stimulant as described above.
Typically the food source is a source of cellulose such as paper, cardboard, canite, chipboard, and sound or fungally decayed wood. The compound of general formula I is applied to the bait matrix in any convenient manner, such as by spraying a solution of the compound on the bait matrix, soaking the bait matrix in such a solution or by admixture with a solid compound of general formula I.
The bait matrix may also contain synergists and other attractants, as well as beneficial components such as nitrogen-containing compounds, carbohydrates and the like as nutrients .
Where necessary, antioxidants such as BHT, BHA or tocopherols may be added to stabilise the active compound within the bait. A controlled release system for the compound of general formula I may be employed where desirable .
Preferably, the bait matrix includes added toxins such as chitin synthesis inhibitors, insect growth regulators and other termiticides . Alternatively, termiticidal substances can be applied to the bait matrix once it has been deployed in the field and has attracted a significant number of termites. In either case, it is preferred that the toxin be slow-acting and non-repellent so as to be transported into the nest by foragers and there distributed throughout the colony either via food exchange or mutual grooming between the nest mates.
According to a fifth aspect of the present invention there is provided a ter iticidal composition comprising:
(1) a termiticidal substance; and
(2) a feeding stimulant as described above. According to a sixth aspect of the present invention there is provided 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, when used for stimulating feeding activity in termites .
According to a seventh aspect of the present invention there is provided 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, when used to attract termites to a locus.
According to an eighth aspect of the present invention there is provided the use of 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, in stimulating feeding activity in termites . According to a ninth aspect of the present invention there is provided the use of 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, in attracting termites to a locus. According to a tenth aspect of the present invention there is provided the use of a compound in the manufacture of a bait for attracting termites, said 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 .
According to an eleventh aspect of the present invention there is provided the use of a compound in the manufacture of a termiticidal composition, said 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.
Typically, the compound having at least two OR groups is a compound of general formula I as described above.
It has been found that para-hydroquinone is the natural feeding stimulant, but exists in the labial glands of termites almost entirely as its glucose conjugate, 4- hydroxyphenyl-β-D-glucopyranoside, which is commonly called β-arbutin. β-Arbutin and glucose conjugates of the other compounds of general formula I may also be used in the invention described above. In particular, β-arbutm or glucose conjugates of the other compounds of formula I can be incorporated into a bait matrix and, through slow decay generating an active compound of general formula I, could act as a slow-release system.
BEST MODE FOR CARRYING OUT THE INVENTION
Preferred embodiments of the invention will now be described, by way of example only, with reference to the following examples.
Example 1 - Use of Labial Glands Extracts as Termite Attractants In order to prepare labial gland extracts, termites were killed and the paired labial glands were removed. The labial glands were disrupted by freezing them for 15 minutes at -20°C and extracted with 0.6 ml of water for 12 hours at room temperature. Then the extract was frozen at -20°C until used. The labial gland extracts prepared and tested are listed m Table I. Each extract was chemically analysed for the presence of para-hydroquinone, and it was found to be present m all. Selected extracts were used in a bioassay to establish feeding choice, as indicated in Table 1, below.
Table 1 : Labial gland extracts prepared and tested
No . of glands Chemically
Termite species Bioassayed
Extracted Analysed
Kalotermes flavicollis 40 + Cryptotermes brevis 70 + + Mastotermes darwimensis 30 + + Hodotermes mossambicus 40 + Zootermopsis angus ti collis 40 + Reticul i termes flavipes 70 + + Reticuli termes san tonensis 70 + + Heterotermes indicola 120 + Schedorhmoter es la anianus 60 + Coptotermes formosanus 70 + + Coptotermes acinaci formis 80 + + Nasu ti termes mgriceps 60 + Nasu ti termes exi tiosus 70 + + Trmervi termes trmervoides 30 + Macrotermes subhyalmus 40 +
The methodology employed in the choice tests was that used by Reinhard et al . supra . In these experiments the termites were housed in a suitable container with access via a silicone tube to a foraging arena . In each experiment two semicircles of moist f ilter paper ( 2 . 5cm in diameter ) were placed close beside each other in the arena . One of the two semicircles was randomly chosen for application of one of the 25μl aliquots of labial gland extract and then moistened with water. The other semicircle was just moistened. Feeding in termites is expressed by gnawing behaviour, which can be easily recognised by the hypognathous head positions wherein the termites bore their mandibles into the food and wriggle their heads trying to tear off little pieces, which they can then transport back to the nest.
The distribution of the first 20 gnawing/ feeding termites on the semicircles was registered. For example, it was observed that 19 of 20 Mas totermes darwini ensis termites responded by gnawing and eating the filter paper treated with one equivalent of its labial gland secretion while only one termite responded to the control. Similarly, 18 of 20 C. acinaciformis termites responded by gnawing and eating the filter paper treated with 2.5 equivalents of its labial gland secretion while 2 responded to the control . A further important observation was that termites of selected species also responded strongly in the bioassay to labial gland secretion from an unrelated species. For instance, C. acinaciformis termites responded to a test paper treated with one equivalent of M. darwiniensis gland secretion while M. darwiniensis termites responded to a test paper treated with 2.5 equivalents of C. acinaciformis gland secretion. These results demonstrate that the labial gland extract is a non-specific feeding stimulant for termites. The results are summarised in Table 2. Table 2: Natural lures
Origin of labial Quantity of
Termite species gland extract (gland Response Responding to lure
Excract equivalents)
M. darwiniensis M. darwiniensis 1 +++
C . acinaci formis 2.5 +++
C. acinaciformis M. darwiniensis 1 +++
C . acinaci formis 2.5 +++
An analysis of the labial gland extract shows that para-hydroquinone is present at low levels, usually less than 1010 grams per gland, but is present at much higher concentrations in the saliva. β-arbutm is present in high concentrations in the glands but is no longer evident in the saliva. Presumably β-arbutm is broken down enzymatically into para-hydroquinone and glucose during release of the termite's saliva, hence it was postulated that para-hydroquinone was the principal chemical feeding stimulant .
Example 2 - Synthetic Compounds as Termite Attractants Feeding choice tests were conducted with para- hydroquinone and a number of related chemical substances in the manner described above in Example 1. The experimental data is summarised in Table 3.
Table 3 : Synthetic lures
Figure imgf000018_0001
* Mixture comprising mainly a pentamer of p- hydroquinone, but including dimer and trimer of p- hydroquinone as impurities. When synthetic lures were tested, none of the principal labial gland constituents (glucose, inositols, β- arbutin) elicited any feeding stimulation, except at unnaturally high concentrations where they probably served a nutritional role as food supplements. However p- hydroquinone elicited feeding stimulation at natural trace levels in the laboratory bioassays. For instance the threshold for attraction was 5 nanograms p-hydroquinone (50 pico oles) for M. darwiniensis and 100 picograms p- hydroquinone (1 picomole) for C. acinaciformis . Thus, there are different lower thresholds of feeding stimulation for different termite species.
Synthetic compounds somewhat related in molecular structure to hydroquinone also elicited feeding responses from M. darwiniensis and C. acinaciformis in the laboratory bioassays, as shown in Table 3.
Example 3 - Mode of Attraction
The mode of attraction of termites to the para- hydroquinone source may well include both olfactory and gustatory stimulation. The attractivity of para- hydroquinone over distance (olfactory perception) was tested both in empty and sand-filled plastic arenas (ID 14.5 cm, height 1 cm, covered with a glass plate), which were attached via a silicone tube to the housing container of the termites. Tests were carried out with M. darwiniensis and C. acinaciformis . Per test, two treated filter papers (25ng - 25μg p-hydroquinone and water as control, respectively) were placed in opposite positions in the arenas. The direction of the tunnel/galleries built and the behaviour of a foraging termites in reference to the position of the filter papers were evaluated. In all tests both termite species built tunnels/galleries in direction to the p-hydroquinone-treated filter paper, never towards the control filter paper. When foraging the termites usually walked slowly in a zigzag way, but when in proximity of the source of p-hydroquinone (ca. 5-6 cm), their behaviour changed suddenly: they walked straight and fast to the treated filter paper. Based on these observational data we concluded that the vapour of p- hydroquinone creates an "active space" of several centimetres, which once perceived directs the termites towards the source of the vapour by the concentration gradient. This active space did not get larger with increased p-hydroquinone concentration.
Example 4 - Choice Feeding Tests Laboratory colonies of Mastotermes darwiniensis and Coptotermes acinaciformis have been tested in a choice feeding test (mimicking an actual bait situation in the field) with pieces of Eucalyptus regnans wood (ca. 3.5g) . The colonies (ca. 500 termites in M. darwiniensis , 2000 termites in C. acinaciformis) were housed in plastic containers. Plastic arenas of 5cm diameter, 3.5cm high were attached with perspex tubes on opposite sides of the colony container. In these arenas the wood was offered: one treated with 20ng p-hydroquinone, dissolved in water, the other just moistened as control. The wood was dried and weighed before and after the test, the difference in weight as the amount eaten by termites was analysed after 3 days , 1 week and 4 weeks .
After 3 days and one week both M. darwiniensis and C. acinaciformis had eaten significantly more of the wood treated with the feeding stimulant than of the control (See Table 4) . After 4 weeks the effect was gone. Therefore p- hydroquinone does act as feeding stimulant in a choice feeding test, although as only a little p-hydroquinone was applied, the effect was only short-term. This could be improved when testing the signal in the field under natural conditions and with complete termite colonies.
Table 4 : Laboratory choice feeding tests with Mastotermes darwini ensis and Copto termes acinaci formis : Amount wood eaten [g] after 3 days, one week and four weeks, comparing wood treated with 20ng p-hydroquinone to control (mean ± sd, n=20, Wilcoxon-Matched-Pairs-Test , ***: significant difference at p<0.001, n.s.: no significant difference).
Figure imgf000021_0001
Example 5 - Field Trials
Colonies of Coptotermes lacteus (ACT) , Coptotermes acinaci formis (NT) and Mas totermes darwini ensis (NT) have been used for large baiting trials in the field.
Furthermore Coptotermes frenchi (ACT), Nasu ti termes exi ti osus (NSW), Schedorhinotermes actuosus (NT),
Coptotermes travians (Malaysia) and Copto termes curvigna thus (Malaysia) have been tested exemplarily at infestation sites in urban areas and in the field. Paper towel of ca . lOg was used as bait matrix. It was either treated with 20μg hydroquinone (dissolved in water) or moistened with water only (=control) . The paper was folded and stuffed in plastic tubes. Termites had access to the bait material through holes drilled into the tubes . One treated and one control bait each were placed at feeding/infestation sites of the field colonies. In case of the larger field trials, up to 24 colonies per species had been selected, and drums filled with wood had been dug into the soil around colonies as feeding sites. Baits were placed on top of the infested drums and covered with plastic foil and soil. In case of the exemplary trials single infestation sites have been selected and the baits were attached directly onto the infestation and covered with plastic foil and soil, or cardboard to ensure minimum disturbance. Baits were checked after 1 to 4 days or after 2 weeks, depending on species and activity. The amount of paper eaten and the number of termites were analysed.
As usual in natural field colonies there was a strong variation of data between colonies, therefore for statistical analysis data had to be transformed into log and square root, respectively. In the large field trials C. lacteus, M. darwini ensis and C . acinaciformis had all consumed significantly more of the bait material and there were more termites attracted to the baits, when hydroquinone had been applied (See Table 5) . The exemplary tests with C. frenchi , S . actuosus , C. travians and C. curvignathus all indicated increased feeding activity on treated baits over control baits (See Table 6) . Tests with N. exi tiosus showed no feeding activity even after long exposure, due to the difficult dietary preferences of this species. However, we could still show increased termite presence in treated baits compared to control baits (See Table 6) . We therefore conclude that hydroquinone in fact acts also under natural conditions in the field as strong and effective attractant and feeding stimulant on various termite species, when added to baits. Table 5 : Field baiting trials with Coptotermes lacteus (ACT) , Copcotermes acinaci formis (NT) and Mas totermes darwiniensis (NT) . ( ) : Amount bait material eaten [g] and (No): number of termites [N} in baits, comparing baits treated with 20μg hydroquinone to control baits (mean ± SE, Paired Samples T-test, ***: significant difference at p<0.001, data transformed to log or sqrt for statistical analysis ) .
Figure imgf000023_0001
Table 6 : Exemplary field baiting trials with Coptotermes frenchi (ACT) , Schedorhinotermes actuosus (NT) , Coptotermes travians (Malaysia) , Coptotermes curvigna thus (Malaysia) and Nasuti termes exi tiosus (NSW) . Proportion bait material eaten [%] or termite presence, respectively, comparing baits treated with 20μg hydroquinone to control baits.
Figure imgf000024_0001
INDUSTRIAL APPLICABILITY
The compounds of the present invention are useful in stimulating feeding activity in termites so as to enhance the effectiveness of termite baits .

Claims

THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS;
1. 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 .
2. A feeding stimulant as claimed in claim 1 wherein at least one R is an organic group and said compound has feeding stimulating activity.
3. A feeding stimulant as claimed in claim 2 wherein said organic group is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
4. A feeding stimulant as claimed in claim 1 wherein at least one R is an organic group and said compound is a precursor of a compound with feeding stimulating activity.
5. A feeding stimulant as claimed in claim 4 wherein said compound is hydrolysed to a compound in which said at least one R is hydrogen.
6. A feeding stimulant as claimed in claim 5 wherein said organic group is a carbohydrate moiety.
7. A feeding stimulant as claimed in claim 6 wherein said compound is β-arbutin.
8. A feeding stimulant as claimed in claim 1 wherein said compound has an aromatic nucleus substituted by said at least two OR groups.
9. A feeding stimulant as claimed in claim 8 wherein said compound has the following general formula I:
Figure imgf000026_0001
wherein Ri is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl;
R2 , R3 , R4 , R5 and Re are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, alkaryl, substituted alkaryl, alkaryloxy and substituted alkaryloxy, or R2 and R3 together, R3 and R4 together, R5 and R5 together and/or R5 and R6 together form an aryl group; provided only that least one of R2 , R3 , R4 , R5 or Rζ is hydroxyl, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, alkaryloxy or substituted alkaryloxy.
10. A feeding stimulant as claimed in claim 9 wherein Ri is selected from the group consisting of hydrogen, alkyl, aryl and alkaryl .
11. A feeding stimulant as claimed in claim 10 wherein Ri is selected from the group consisting of hydrogen, methyl, ethyl, phenyl and benzyl.
12. A feeding stimulant as claimed in claim 11 wherein Ri is hydrogen.
13. A feeding stimulant as claimed in any one of claims 9 to 12 wherein R2, R , R , R5 and R5 are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, alkoxy, aryl, aryloxy, alkaryl, and alkaryloxy.
14. A feeding stimulant as claimed in claim 13 wherein R , R3 , R4, R5 and R6 are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
15. A feeding stimulant as claimed in claim 14 wherein R2 or R6 is hydroxyl .
16. A feeding stimulant as 'claimed in claim 14 wherein R3 or R5 is hydroxyl.
17. A feeding stimulant as claimed in claim 14 wherein R4 is hydroxyl .
18. A feeding stimulant as claimed in claim 1 wherein said compound is selected from the group consisting of: p-hydroquinone quinhydrone catechol resorcinol phloroglucinol
4-methoxyphenol methoxyhydroquinone
1, 4-dimethoxybenzene 4-phenoxyphenol phenylhydroquinone
4-benzyloxyphenol
1 . A feeding stimulant as claimed in claim 1 wherein said compound has a plurality of aryl moieties.
20. A feeding stimulant as claimed in claimed 19 wherein each said aryl moiety is a benzene ring.
21. A feeding stimulant as claimed in claim 20 wherein said compound is a polyphenylether.
22. A feeding stimulant as claimed in any one of claims 1 to 21 further comprising a biologically acceptable carrier and/or extender.
23. A method of stimulating feeding activity in termites, comprising the steps of:
(1) providing a feeding stimulant as claimed in any one of claims 1 to 22; and
(2) applying said feeding stimulant to a locus.
24. A feeding stimulant as claimed in claim 23 wherein there is a food source at said locus.
25. A method of attracting termites to a locus, comprising the steps of: (1) providing a food source at said locus;
(2) providing a feeding stimulant as claimed in any one of claims 1 to 22; and
(3) applying said feeding stimulant to said 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. A bait as claimed in claim 26 wherein said food source is a source of cellulose.
28. A bait as claimed in claim 27 wherein said food source is selected from the group consisting of paper, cardboard, canite, chipboard, sound wood and fungally decayed wood.
29. A bait as claimed in any one of claims 26 to 28 further comprising a termiticidal substance.
30. A bait as claimed in claim 29 in which said termiticidal substance is a chitin synthesis inhibitor or an insect growth regulator.
31. A bait as claimed in any one of claims 26 to 30 further comprising an antioxidant .
32. A bait as claimed in any one of claims 26 to 31 further comprising a synergist and/or other attractants.
33. A bait as claimed in any one of claims 26 to 32 further comprising nutrients such as nitrogen-containing compounds and carbohydrates .
34. A termiticidal composition comprising:
(1) a termiticidal substance; and
(2) a feeding stimulant as claimed in any one of claims 1 to 22.
35. A termiticidal composition as claimed in claim 34 wherein said termiticidal substance is a chitin synthesis inhibitor or insect growth regulator.
36. 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, when used for stimulating feeding activity in termites.
37. A compound as claimed in claim 36 of general formula I as defined in claim 9.
38. 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, when used to attract termites to a locus.
39. A compound as claimed in claim 38 of general formula I as defined in claim .
40. The use of 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, in stimulating feeding activity in termites.
41. The use of a compound as claimed in claim 40 wherein said compound is of general formula I as defined in claim 9.
42. The use of 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, in attracting termites to a locus.
43. The use of a compound as claimed in claim 42 wherein said compound is of general formula I as defined in claim 9.
44. The use of a compound in the manufacture of a bait for attracting termites, said 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 .
45. The use of compound as claimed in claim 44 wherein said compound is of general formula I as defined in claim 9.
46. The use of a compound in the manufacture of a termiticidal composition, said 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.
47. The use of a compound as claimed in claim 46 wherein said compound is of general formula I as defined in claim 9.
PCT/AU1999/001033 1998-12-22 1999-11-25 Termite attractant and/or feeding stimulant WO2000036914A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2000589037A JP2002532519A (en) 1998-12-22 1999-11-25 Termite attractants and / or feeding stimulants
BR9916480-9A BR9916480A (en) 1998-12-22 1999-11-25 Termites or Termites Food Stimulant and Method of Stimulating Termites or Termites Food Activity
AU15374/00A AU762004B2 (en) 1998-12-22 1999-11-25 Termite attractant and/or feeding stimulant
APAP/P/2001/002190A AP2001002190A0 (en) 1998-12-22 1999-11-25 Termite attractant and/or feeding stimulant.
EP99957752A EP1139742A4 (en) 1998-12-22 1999-11-25 Termite attractant and/or feeding stimulant
HK02104481.6A HK1042628A1 (en) 1998-12-22 2002-06-17 Termite attractant and/or feeding stimulant

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
WO2000036914A1 true WO2000036914A1 (en) 2000-06-29

Family

ID=3812046

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1999/001033 WO2000036914A1 (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)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
US10575520B2 (en) * 2016-03-16 2020-03-03 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Cyclohexylamine-based compounds and uses thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1062583A (en) * 1982-01-22 1983-07-28 Montedison S.P.A. 1((5-chioro-pent-4-inyl)-oxy)-4-phenoxy-benzene
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
JPH03112903A (en) * 1989-09-27 1991-05-14 Nitto Denko Corp Termite trail pheromone preparation
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4880624A (en) * 1988-03-18 1989-11-14 The Board Of Trustees Of The University Of Illinois Volatile attractants for diabrotica species
US5780515A (en) * 1996-03-21 1998-07-14 Rockhurst University Benzoquinone and hydroquinone derivatives for use as insect feeding deterrents

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1062583A (en) * 1982-01-22 1983-07-28 Montedison S.P.A. 1((5-chioro-pent-4-inyl)-oxy)-4-phenoxy-benzene
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
JPH03112903A (en) * 1989-09-27 1991-05-14 Nitto Denko Corp Termite trail pheromone preparation
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

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
"PHLOROGLUCINOL DIHYDRATE", ALDRICH CATALOGUE, HANDBOOK OF FINE CHEMICALS, XX, XX, 1 January 1990 (1990-01-01), XX, pages 01 - 10, XP002949423 *
CHEMICAL ABSTRACTS, vol. 97, no. 15, 1982, Columbus, Ohio, US; abstract no. 122002A, YAGA SHIRYO: "Termite resistance of Okinawan timbers. VIII. New termite control agents from reduced benzoic derivatives" page 222-223; XP002949425 *
DATABASE WPI Week 8915, Derwent World Patents Index; Class C03, AN 1989-110592/15, XP002948098 *
DATABASE WPI Week 9344, Derwent World Patents Index; Class C03, AN 1993-348296/44, XP002948099 *
DATABASE WPI Week 9413, Derwent World Patents Index; Class C03, AN 1993-348296/44, XP002948100 *
Kodak Catalog no. 46, Eastman Organic Chemicals, Rochester, New York, USA 1971 (see product number 11206 (Poly-m-phenoxylene, page 159) *
MOKUZAI GAKKAISHI, vol. 28, no. 6, 1982, pages 393 - 398 (JAPANESE) *
PATENT ABSTRACTS OF JAPAN (C - 199) *
PATENT ABSTRACTS OF JAPAN (C - 856) *
See also references of EP1139742A4 *
Sigma Chemical Company Catalog of Biochemicals Organic Compounds for Research, 1993 (see product number A4256 (arbutin, page 126) XP002949424 *

Cited By (6)

* Cited by examiner, † Cited by third party
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
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
US7030156B2 (en) 2001-03-05 2006-04-18 University Of Florida Research Foundation, Inc Devices and methods for eliminating termite colonies
US7157078B2 (en) 2001-03-05 2007-01-02 The University Of Florida Research Foundation, Inc. Devices and methods for eliminating termite colonies
US10575520B2 (en) * 2016-03-16 2020-03-03 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Cyclohexylamine-based compounds and uses thereof

Also Published As

Publication number Publication date
ZA200105010B (en) 2002-06-19
EP1139742A1 (en) 2001-10-10
CN1337849A (en) 2002-02-27
OA11814A (en) 2005-08-16
ID29807A (en) 2001-10-11
JP2002532519A (en) 2002-10-02
BR9916480A (en) 2002-01-15
AP2001002190A0 (en) 2001-05-25
HK1042628A1 (en) 2002-08-23
AUPP784298A0 (en) 1999-01-21
EP1139742A4 (en) 2002-07-31

Similar Documents

Publication Publication Date Title
US5536501A (en) Use of flavenoid aldehydes as insecticides and for killing arachnids
US4049460A (en) Roach bait composition
US5900244A (en) Insect attractant
US6906108B2 (en) Extracts of vetiver oil as repellent and toxicant to ants, ticks, and cockroaches
Reierson Baits for German cockroach control
WO2004073402A2 (en) Gellable ant bait matrix
US5637298A (en) Composition and method for killing termites
WO2000036914A1 (en) Termite attractant and/or feeding stimulant
US4540711A (en) Method for combatting infestations of insects and acari, and compositions for use in said method
US5177107A (en) Method for the control of insects
Dindonis et al. Onion fly and little house fly host finding selectively mediated by decomposing onion and microbial volatiles
KR100377961B1 (en) A line fluid for an insect inducement and capture, and the manufacturing method of the above fluid
AU762004B2 (en) Termite attractant and/or feeding stimulant
US4853217A (en) Methods and compositions for controlling the pear leaf blister moth, Leucoptera scitella
WO1997014304A1 (en) Phototoxic insecticidal composition and method for controlling insect populations
Schroder et al. Evaluation of a water-soluble bait for corn rootworm (Coleoptera: Chrysomelidae) control
WO2008095016A2 (en) Insect attractant formulations
Prestwich et al. Comparative toxicity of fluorinated lipids and their evaluation as bait-block toxicants for the control of Reticulitermes spp.(Isoptera: Rhinotermitidae)
Logan et al. Laboratory trials on the toxicity of hydramethylnon (Amdro; AC 217,300) to Reticulitermes santonensis Feytaud (Isoptera: Rhinotermitidae) and Microtermes lepidus Sjöstedt (Isoptera: Termitidae)
Livingston et al. Verbenone interrupts attraction of roundheaded pine beetle, Dendroctonus adjunctus (Coleoptera: Scolytidae), to sources of its natural attractant
EP0162055A1 (en) Fruit fly attractants and baits
HU176515B (en) Composition for enticing male agrotis of cabbage
AU2005244166B2 (en) Composition for control of cockroaches
JP2000007516A (en) Termite-bait composition free from ureide
JP2004123669A (en) Poison bait for exterminating termite

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 99816317.1

Country of ref document: CN

ENP Entry into the national phase

Ref document number: 2000 15374

Country of ref document: AU

Kind code of ref document: A

AK Designated states

Kind code of ref document: A1

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2001/05010

Country of ref document: ZA

Ref document number: 200105010

Country of ref document: ZA

Ref document number: 15374/00

Country of ref document: AU

ENP Entry into the national phase

Ref document number: 2000 589037

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2001/679/KOL

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 1200100649

Country of ref document: VN

WWE Wipo information: entry into national phase

Ref document number: 1999957752

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1999957752

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09868785

Country of ref document: US

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWG Wipo information: grant in national office

Ref document number: 15374/00

Country of ref document: AU

WWW Wipo information: withdrawn in national office

Ref document number: 1999957752

Country of ref document: EP