OA11814A

OA11814A - Termite attractant and/or feeding stimulant.

Info

Publication number: OA11814A
Application number: OA1200100159A
Authority: OA
Inventors: Michael James Lacey; Judith Reinhard; Michael Lenz
Original assignee: Commw Scient Ind Res Org
Priority date: 1998-12-22
Filing date: 1999-11-25
Publication date: 2005-08-16
Also published as: AP2001002190A0; CN1337849A; BR9916480A; ID29807A; AUPP784298A0; WO2000036914A1; JP2002532519A; EP1139742A4; ZA200105010B; HK1042628A1; EP1139742A1

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

118 14

TERMITE ATTRACTANT AND/OR FEEDING STIMULANT

TECHNICAL FIELD

The présent invention is concerned withattractants and/or feeding stimulants for termites and,more particularly, with attractants and/or feedingstimulants for use in termite baits and as a component oftermiticidal compositions.

BACKGROUND ART

Organochlorines hâve underpinned termite controlaround the world including in Australia, for many décades.With the ban on the use of organochlorines for termitecontrol in Australia since 1995 and earlier or at similartimes in other countries, increasing efforts are beingmounted to develop alternative termite management système.Bait Systems for the control of active termite infestationsare considered increasingly the key management option forsuch situations.

In bait Systems termites are offered a matrix onwhich the insects ought to feed in preference to other foodsources available to a termite colony. Termites eithertake up a slow-acting, non-repellent léthal product whichis incorporated into the food (matrix) or the termiteswhich aggregate in the matrix are directly treated withsuch a product. In both scénarios the agent is transportedinto the nest by the foragers and there distributedthroughout the colony either via food exchange or mutualgrooming between nest mates.

Following considérable research around the worldthere is now a growing awareness that just finding aneffective bait toxin, initially thought to be the mainimpediment to the application of baits, is no guarantee atail that a bait System will work effectively in practice.Control strategies relying on baits hâve to cope with thefact that termites hâve a choice and that the insectscannot be forced to make contact with the baits. Termites

11314 I hâve to be able to locate a bait station in the firstplace, and once it is found, be attracted to it insignificant numbers so that adéquate transfer of the toxinfrom the bait site to the colony can occur. Différences inbehaviour between species of termite, between colonieswithin a species and between conditions at various sitespotentially restrict the effectiveness of this controlstrategy. Currently used bait matrices, in most cases juststraight cellulose products (timber, cardboard, paper), donot necessarily ensure contact and build up of termitenumbers in bait stations in a reliable, predictablefashion.

Attempts hâve been made to enhance the attractionof termites to bait matrices through the addition ofattractant compounds/ For example, InternationalApplication WO99/07218 describes the use of 2,4 heptadienalas an attractant for social pest insects such as wasps andtermites. United States Patent No. 5,637,298 describes 2-4naphthalenemethanol dérivative substituted at the 7 or 8position of the naphthalene ring structure by methyl,ethyl, propyl or isopropyl, and indicates that thesecompounds increase bait acceptance by termites. Likewise,United States Patent No. 5,756,114 describes theincorporation of certain aromatic compounds includingresorcylic acid, protecatechuic acid and vanillic acid intobaits on the basis that they act as food odour attractants.These compounds apparently mimic the trail-markingpheromone (Z,Z,E)-3,6,8-dodecatrien-l-ol. Thus, while theypromote termite aggregation they do not necessarilystimulate feeding behaviour, and any increased feeding maybe a conséquence only of the increased numbers of termitesat a selected site.

Termites are social insects and the socialorganisation of termite colonies largely dépends onChemical signais présent in the environment or produced bymembers of the colony. These signais modulate a variety ofbehaviours including foraging for food or communal i 18 i u exploitation of a food source. For example, during feeding, termites release a Chemical signal from an exocrine gland that stimulâtes nest mates to feed at thesame site, thereby ensuring a rapid and efficientexploitation of the food source.

Ail species of termite hâve paired labial glandslocated in the thorax. The glandular ducts join in thehead with those of the water sacs and the contents aresecreted from the mouth as saliva. This sécrétion has beenreported to hâve various functions depending on thespecies, and has variously been identified as a défensivesubstance in soldier termites, a regulator of nestmicroclimate, a supporter of fungal cultivation in the nestor as a social nutrient. In addition, the labial glandshâve been said to secrete a cementing substance for nestconstruction or gallery building and hâve been identifiedas a source of digestive enzymes.

More recently, Reinhard et al., Journal ofChemical Ecology, Vol. 23 No. 10, 1997 concluded that thelabial gland sécrétion may play a pheromonal rôle duringfood exploitation, and that this might be a generalphenomenon in termites. Reinhard et al. took labial glandextracts and used these in feeding choice tests. Theyobserved that the labial gland sécrétion carries a signalthat stimulâtes gnawing and feeding by termite workersduring food exploitation. The extract of the labial glandeven elicited feeding behaviour when applied without foodonto glass plates. These extracts were tested with bothReticulitermes santonensis and Schedorhinotermes lamanianusand proved to elicit a significant feeding preference inthe two species. In view of this, Reinhard et al.suggested that the signal function of the labial glandsécrétion for food exploitation is phylogenetically old andnon-species spécifie. The Chemical signal has now beenidentified for the first time and has proved to work as apowerful feeding stimulant at natural low concentrations ona wide range of termite species. In view of this a class 4 118 14 of compounds which stimulate termite feeding has beenidentified.

DISCLOSURE OF THE INVENTION

According to a first aspect of the présent invention thereis provided a feeding stimulant for stimulating feedingactivity in termites# comprising an effective amount of acompound capable of stimulating feeding activity intermites, said compound having at least two OR groups, eachof which is a substituent of an aryl moiety, and R ishydrogen or an organic group, and addition compoundsthereof, and a biologically acceptable carrier and/orextender.

Where the feeding stimulant is a compound inwhich at least one Ris an organic group it may hâvefeeding stimulating activity or may be a pre-cursor of acompound with feeding stimulating activity.

In the former case, the organic group ispreferably selected from the group consisting of alkyl,substituted alkyl, aryl or substituted aryl, and in thelatter case is typically a compound which is hydrolysed toone having feeding stimulating activity, such as those inwhich the organic group is a carbohydrate moiety. β-Arbutin is one such compound. Polymers or oligomers suchas polyphenylethers, as well as being long-lived in theenvironment, will progressively hydrolyse to compoundshaving feeding stimulating activity.

Compounds having feeding stimulating activitytypically comprise a benzene ring substituted by said atleast two OR groups.

Typically such compounds hâve the followinggeneral formula I:

5 118 14 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 selectedfrom the group consisting of hydrogen, hydroxyl, alkyl,substituted alkyl, alkoxy, substituted alkoxy, aryl,substituted aryl, aryloxy, substituted aryloxy, aralkyl,substituted aralkyl, aralkyloxy and substituted aralkyloxy,or R2 and R3 together, R3 and R4 together, R4 and R5 togetherand/or R5 and R6 together form an aryl group; provided only that at least one of R2, R3, R4, R5or R6 is hydroxyl, alkoxy, substituted alkoxy, aryloxy,substituted aryloxy, aralkyloxy or substituted aralkyloxy.Preferably, Ri is selected from the group consisting ofhydrogen, alkyl, aryl and aralkyl.

More preferably. Ri is selected from the group consistingof hydrogen, methyl, ethyl, phenyl and benzyl.

More preferably still, Ri is hydrogen.

Preferably, R2, R3, R4, R5 and Rs are independentlyselected from the group consisting of hydrogen, hydroxyl,alkyl, alkoxy, aryl, aryloxy, aralkyl, and aralkyloxy.

More preferably, R2, R3, R4, R5 and R6 are independentlyselected from the group consisting of hydrogen, hydroxyl,methyl, ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl andbenzyloxy.

More preferably still, at least one of R2, R3, R4, R5 or R6is hydroxyl. In particular, R2 or R6, R3 or Rs or R4 istypically hydroxyl.

Particularly preferred compounds for use in theprésent invention are selected from the group consistingof : 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) 6 118 14 1 1,4-dimethoxybenzene 4-phenoxypheno1 phenylhydroguinone 4-benzyloxyphenol

Moreover, addition compounds such as quinhydrone(an addition compound of 1 mole hydroquinone and 1 molequinone) are also envisaged.

Alternatively, said compound may hâve a pluralityof aryl moieties.

Preferably each said aryl moiety is a benzenering and the compound is a polyphenylether. Typically, thepolyphenylether is an ether of p-hydroquinone havingbetween 2 and 5 p-hydroquinone residues.

As used throughout the spécification and daimsthe term "alkyl" refers to straight or branched chain alkylradicals, preferably Ci-Ci0 alkyl radicals and, morepreferably, Ci_C4 alkyl radicals.

As used throughout the spécification and daimsthe term "substituted alkyl" refers to an alkyl radicalsubstituted 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 spécification the term"aryl" refers to a six-membered carbocyclic aromatic ringor a five- or six-membered heterocyclic aromatic ringcontaining 1, 2 or 3 oxygen, nitrogen or sulphur atoms asthe heteroatom, and includes fused ring Systems containinga plurality of such rings.

As used throughout the spécification and daimsthe term "substituted aryl" refers to an aryl radicalsubstituted by any substituent, conveniently, by alkyl,hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl,carbamido, amino, mono- or di- alkyl substituted amino,halogen, alkylcarbonyloxy or alkylcarbonylamino.

As used throughout the spécification and daimsthe term "alkoxy" refers to an alkoxy radical containing a 7 118 14 straight or branched chain alkyl radicale, preferably Ci-Cioalkyl radicals and, more preferably, C1_C4 alkyl radicals.

As used throughout the spécification and daimsùhe term "substituted alkoxy" refers to an alkoxy radicalsubstituted 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 spécification and daimsthe term "aryloxy" refers to an aryloxy radical containinga six-membered carbocyclic aromatic ring or a five- or six-membered heterocyclic aromatic ring containing 1, 2 or 3oxygen, nitrogen or sulphur atoms as the heteroatom, andincludes fused ring Systems containing a plurality of suchrings.

As used throughout the spécification and daimsthe term "substituted aryloxy" refers to an aryloxy radicalsubstituted by any substituent, conveniently, by alkyl,hydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl,carbamido, amino, mono- or di- alkyl substituted amino,halogen, alkylcarbonyloxy or alkylcarbonylamino.

As used throughout the spécification and daimsthe term "aralkyl" refers to an aralkyl radical comprisinga straight or branched chain alkylene radical, preferably aCi-Cio alkylene radical and, more preferably, a Ci_C4alkylene radical and a six-membered carbocyclic aromaticring or a five- or six-membered heterocyclic aromatic ringcontaining 1, 2 or 3 oxygen, nitrogen or sulphur atoms asthe heteroatom, and includes fused ring Systems containinga plurality of such rings.

As used throughout the spécification and daimsthe term "substituted aralkyl" refers to an aralkyl radicalsubstituted 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 spécification and daims 10 15 20 25 30

F

the term "aralkyloxy" refers to an aralkyloxy radicalcontaining a straight or branched chain alkyleneoxy group,preferably a Ci-Ci0 alkyleneoxy group and, more preferably,Ci_C4 alkyleneoxy group, and a six-membered carbocyclicaromatic ring or a five- or six-membered heterocyclicaromatic ring containing 1, 2 or 3 oxygen, nitrogen orsulphur atoms as the heteroatom, and includes fused ringSystems containing a plurality of such rings.

As used throughout the spécification and daimsthe term "substituted aralkyloxy" refers to an aralkyloxyradical substituted by any substituent, conveniently, byhydroxyl, alkoxy, carboxy, carboxyalkyl, carbamoyl,carbamido, amino, mono- or di- alkyl substituted amino,halogen, alkylcarbonyloxy or alkylcarbonylamino.

As used throughout the spécification and daims,the words "comprise", "comprises" and "comprising" areused in a non-exclusive sense, except where the contextrequires otherwise.

According to a second aspect of the présent invention thereis provided a method of stimulating feeding activity intermites, comprising the steps of: providing a feeding stimulant as described above; andapplying said feeding stimulant to a locus.

Preferably, there is a food source at said locus.

According to a third aspect of the présentinvention there is provided a method of attractingtermites to a locus, comprising the steps of:providing a food source at said locus, providing a feeding stimulant as described above; andapplying said feeding stimulant to said locus.

The compounds of general formula I act as afeeding stimulant and/or attractant to termite species, inparticular, to Mastotermes darwiniensis, Coptotermesacînaciformis, Kalotermes flavicollis, Cryptotermes brevis,Hodotermes mossambicus, Zootenoopsis angusticollis,

Reticulitermes flavipes, Reticulitermes santonensis,Heterotermes indicola, Schedorhinotermes lamanianus, 35 9 118 14

Coptotermes formosanus, Nasutitermes nigriceps,

Nasutitermes exitiosus, Trinervitermes trinervoides andMacrotermes subhyalinus.

According to a fourth aspect of the présentinvention there is provided a bait for attractingtermites, comprising: a food source; and a feeding stimulant as described above.

Typically the food source is a source ofcellulose such as paper, cardboard, canite, chipboard, andSound or fungally decayed wood. The compound of generalformula I is applied to the bait matrix in any convenientmanner, such as by spraying a solution of the compound onthe bait matrix, soaking the bait matrix in such a solutionor by admixture with'a solid compound of general formula I.

The bait matrix may also contain synergists andother attractants, as well as bénéficiai components such asnitrogen-containing compounds, carbohydrates and the likeas nutrients.

Where necessary, antioxidants such as BHT, BHA ortocopherols may be added to stabilise the active compoundwithin the bait. A controlled release System for thecompound of general formula I may be employed wheredésirable.

Preferably, the bait matrix includes added toxinssuch as chitin synthesis inhibitors, insect growthregulators and other termiticides. Alternatively,termiticidal substances can be applied to the bait matrixonce it has been deployed in the field and has attracted asignificant number of termites. In either case, it ispreferred that the toxin be slow-acting and non-repellentso as to be transported into the nest by foragers and theredistributed throughout the colony either via food exchangeor mutual grooming between the nest mates.

According to a fifth aspect of the présent invention there is provided a termiticidal composition comprising: 10 118 14 a termiticidal substance; and a feeding stimulant as described above.

According to a sixth aspect of the présentinvention there is provided a compound having at least twoOR groups, each of which is a substituent of an arylmoiety, and R is hydrogen or an organic group, and additioncompounds thereof, when used for stimulating feedingactivity in termites.

According to a seventh aspect of the présentinvention there is provided a compound having at least twoOR groups/ each of which is a substituent of an arylmoiety, and R is hydrogen or an organic group, and additioncompounds thereof, when used in an amount effective tostimulate feeding activity in termites to attract termitesto a locus.

According to an eighth aspect of the présentinvention there is provided the use of a compound having atleast two OR groups, each of which is a substituent of anaryl moiety, and R is hydrogen or an organic group, andaddition compounds thereof, in stimulating feeding activityin termites.

According to a ninth aspect of the présentinvention there is provided the use in an amount effectiveto stimulate feeding activity in termites of a compoundcapable of stimulating feeding activity in termites, saidcompound having at least two OR groups, each of which is asubstituent of an aryl moiety, and R is hydrogen or anorganic group, and addition compounds thereof, to attracttermites to a locus.

According to a tenth aspect of the présentinvention there is provided the use in an amount effectiveto stimulate feeding activity in termites of a compoundcapable of stimulating feeding activity in termites in themanufacture of a bait for attracting termites, saidcompound having at least two OR groups, each of which is asubstituent of an aryl moiety, and R is hydrogen or anorganic group, and addition compounds thereof. 118 14 11

According to an eleventh aspect of the présentinvention there is provided the use in an amount effectiveto stimulate feeding activity in termites of a compoundcapable of stimulating feeding activity in termites in themanufacture of a termiticidal composition, said compoundhaving at least two OR groupe, each of which is a substituent of an aryl moiety, and R is hydrogen or anorganic group, and addition compounds thereof.

According to a twelfth aspect of the présentinvention there is provided a method of stimulating feedingactivity in termites, comprising the steps of: (1) providing a compound effective instimulating feeding activity in termites having at leasttwo OR groups, each of which is a substituent of an arylmoiety, and R is hydrogen or an organic group, and additioncompounds thereof; and (2) applying said compound to a locus.

Typically, the compound having at least two OR groups is a compound of general formula I as describedabove.

It has been found that para-hydroquinone is thenatural feeding stimulant, but exists in the labial glandsof termites almost entirely as its glucose conjugate, 4-hydroxyphenyl-6-D-glucopyranoside, which is commonly calledβ-arbutin. β-Arbutin and glucose conjugates of the othercompounds of general formula I may also be used in theinvention described above. In particular, β-arbutin orglucose conjugates of the other compounds of formula I canbe incorporated into a bait matrix and, through slow decaygénérâting an active compound of general formula I, couldact as a slow-release System.

BEST MODE FOR CARRYING PUT THE INVENTION

Preferred embodiments of the invention will nowbe described, by way of example only, with reference to thefollowing examples.

Example 1 - Use of Labial Glands Extracts as Termite 12 118 14

Attractants

In order to préparé labial gland extracts,termites were killed and the paired labial glands wereremoved. The labial glands were disrupted by freezing themfor 15 minutes at -20°C and extracted with 0.6 ml of waterfor 12 hours at room température. Then the extract wasfrozen at -20°C until used. The labial gland extractsprepared and tested are listed in Table I. Each extract waschemically analysed for the presence of para-hydroquinone,and it was found to be présent in ail. Selected extractswere used in a bioassay to establish feeding choice, asindicated in Table 1, below.

Table 1: Labial gland extracts prepared and testedNo. of glands Chemically

Termite species Bioassayed

Extracted Analysed

Kalotermes flavicollis 40 + Cryptotermes brevis 70 + + Mastotermes darwiniensis 30 + + Hodotermes mossambicus 40 + Zootermopsis angusticollis 40 + Reticulitermes flavipes 70 + Reticulitermes santonensis 70 + + Heterotermes indicola 120 + Schedorhinotermes lamanianus 60 + Coptotermes formosanus 70 + + Coptotermes acinacïformis 80 + + Nasutitermes nigriceps 60 + Nasutitermes exitiosus 70 + + Trinervitermes trinervoides 30 + Macrotermes subhyalinus 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 withaccess via a silicone tube to a foraging arena. In eachexperiment two semicircles of moist filter paper (2.5cm indiameter) were placed close beside each other in the arena.One of the two semicircles was randomly chosen for 13 11814 » application of one of the 25μ1 aliquots of labial glandextract and then moistened with water. The othersemicircle was just moistened. Feeding in termites isexpressed by gnawing behaviour, which can be easily 5 recognised by the hypognathous head positions wherein thetermites bore their mandibles into the food and wriggletheir heads trying to tear off little pièces, which theycan then transport back to the nest.

The distribution of the first 20 gnawing/feeding10 termites on the semicircles was registered. For example, it was observed that 19 of 20 Mastotermes darwiniens!stermites responded by gnawing and eating the filter papertreated with one équivalent of its labial gland sécrétionwhile only one termite responded to the control. 15 Similarly, 18 of 20 C. acinaciformis termites responded bygnawing and eating the filter paper treated with 2.5équivalents of its labial gland sécrétion while 2 respondedto the control. A further important observation was thattermites of selected species also responded strongly in the 20 bioassay to labial gland sécrétion from an unrelated species. For instance, C. acinaciformis termites respondedto a test paper treated with one équivalent of M. darwiniensis gland sécrétion while M. darwiniensis termitesresponded to a test paper treated with 2.5 équivalents of 25 C. acinaciformis gland sécrétion. These resuits demonstrate that the labial gland extract is a non-specificfeeding stimulant for termites. The results are summarisedin Table 2.

Table 2 : Natural lures

Origin of labial Quantity of

Termite species gland extract (gland Response

Responding to lure

Extract équivalents) M. darwiniensis M.darwiniensis 1 C.acinaciformis 2.5 C.acinaciformis M. darwiniensis 1 C.acinaciformis 2.5 + + + + + + + + + +++ 30 118 14 14

An analysis of the labial gland extract showsthat para-hydroquinone is présent at low levels, usuallyless than 1O’10 grams per gland, but is présent at muchhigher concentrations in the saliva. β-arbutin is présent 5 in high concentrations in the glands but is no longer évident in the saliva. Presumably β-arbutin is broken downenzymatically into para-hydroquinone and glucose duringrelease of the termite's saliva, hence it was postulatedthat para-hydroquinone was the principal Chemical feeding 10 stimulant.

Example 2 - Synthetic Compounds as Termite Attractants

Feeding choice tests were conducted with para-hydroquinone and a number of related Chemical substances in 15 the manner described-above in Example 1. The experimentaldata is summarised in Table 3.

Table 3 : Synthetic lures

Termite species responding to lure Compound Quantity in Lure [ng] Response M. darwiniens!s p-hydroquinone 5 +++ Quinhydrone 5 ++ Catechol 5 -/ + Resorcinol 5 + Phloroglucinol 5 -/ + 4-methoxyphenol 5 + Methoxyhydrocruinone 5 + 1,4-dimethoxybenzene 5 + + 4-phenoxyphenol 5 -/ + phenylhydroquinone 5 + polyphenylether* 5 + 4-benzyloxyphenol 5 -/ + C. acinacif omis p-hydroquinone 1 + + + quinhydrone 5 + + catechol 5 + + resorcinol 5 + + phloroglucinol 5 + + 4-methoxyphenol 5 + methoxyhydroquinone 5 +

15 1,4-dimethoxybenzene 5 + 4-phenoxypheno1 5 -/ + phenvlhydroquinone 5 « polyphenylether* 5 4-benzyloxyphenol 5 S. actuosus p-hydroquinone 5 +++ C.brevis p-hvdroguinone 5 +++ N. exitiosus p-hydroqu inone 5 + + + R.santonensis p-hydroquinone 5 + + + R.flavines p-hydroquinone 5 +++ C.foxmosanus p-hydroquinone 5 +++ * 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 theprincipal labial gland constituents (glucose, inositols, β-arbutin) elicited any feeding stimulation, except atunnaturally high concentrations where they probably serveda nutritional rôle as food suppléments. However p-hydroquinone elicited feeding stimulation at natural tracelevels in the laboratory bioassays. For instance thethreshold for attraction was 5 nanograms p-hydroquinone (50picomoles) for M. darwiniensïs and 100 picograms p-hydroquinone (1 picomole) for C. acinacïformis. Thus,there are different lower thresholds of feeding stimulationfor different termite species.

Synthetic compounds somewhat related in molecularstructure to hydroquinone also elicited feeding responsesfrom M. darwiniensïs and C. acinacïformis in the laboratorybioassays, 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 andgustatory stimulation. The attractivity of para-hydroquinone over distance (olfactory perception) was 16 113 14

tested both in empty and sand-filled plastic arenas (ID 14.5 cm, height 1 cm, covered with a glass plate), whichwere attached via a silicone tube to the housing containerof the termites. Tests were carried out with M. darwinïensis and C. acinaciformis. Per test, two treatedfilter papers (25ng - 25pg p-hydroquinone and water ascontrol, respectively) were placed in opposite positions inthe arenas. The direction of the tunnel/galleries built andthe behaviour of a foraging termites in reference to theposition of the filter papers were evaluated. In ail testsboth termite species built tunnels/galleries in directionto the p-hydroquinone-treated filter paper, never towardsthe control filter paper. When foraging the termitesusually walked slowly in a zigzag way, but when inproximity of the source of p-hydroquinone (ca. 5-6 cm),their behaviour changed suddenly: they walked straight andfast to the treated filter paper. Based on theseobservational data we concluded that the vapour of p-hydroquinone créâtes an "active space" of severalcentimètres, which once perceived directs the termitestowards the source of the vapour by the concentrationgradient. This active space did not get larger withincreased p-hydroquinone concentration.

Example 4 - Choice Feeding Tests

Laboratory colonies of Mastotermes darwiniensis and Coptotermes acinaciformis hâve been tested in a choicefeeding test (mimicking an actual bait situation in thefield) with pièces of Eucalyptus regnans wood (ca. 3.5g).The colonies (ca. 500 termites in M. darwiniensis, 2000termites in C. acinaciformis) were housed in plasticcontainers. Plastic arenas of 5cm diameter, 3.5cm highwere attached with perspex tubes on opposite sides of thecolony 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 driedand weighed before and after the test, the différence in 17 118 14 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. darwiniensïsand C. acinaciformïs had eaten signïficantly more of thewood 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 achoice 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 fieldunder natural conditions and with complété termitecolonies.

Table 4 : Laboratory choice feeding tests with Mastotermesdarwiniensïs and Coptotermes acinaciformist Amount woodeaten [g] after 3 days, one week and four weeks, comparingwood treated with 20ng p-hydroquinone to control (mean ±sd, n=20, Wilcoxon-Matched-Pairs-Test, ***: significantdifférence at p<0.001, n.s.: no significant différence).

Species Duration of trial Treated wood eaten (g] Control wood eaten [g] P M.darwiniensïs 3 days 0.234±0.139 0.121+0.108 1e ★ W 1 week 0.737±0.557 0.506±0.527 ★ * 4 weeks 2.397±0.968 2.255±0.918 n.s. C.acinaciformis 3 days 0.056+0.0.36 0.032±0.033 ★ * 1 week 0.185±0.159 0.096+0.109 ** 4 weeks 1.162±0.851 1.209±0.929 n.s.

Example 5 - Field Trials

Colonies of Coptotermes lacteus (ACT),

Coptotermes acinacifomis (NT) and Mastotermes darwiniensïs(NT) hâve been used for large baiting trials in the field.Furthermore Coptotermes frenchi (ACT), Nasutitermesexitiosus (NSW), Schedorhinotermes actuosus (NT),

Coptotermes travians (Malaysia) and Coptotermes curvignathus (Malaysia) hâve been tested exemplarily at infestation sites in urban areas and in the field. Paper 18 118 14 towel of ca. 10g was used as bait matrix. It was eithertreated with 20pg hydroquinone (dissolved in water) ormoistened with water only (=control). The paper was foldedand stuffed in plastic tubes. Termites had access to thebait material through holes drilled into the tubes. Onetreated and one control bait each were placed atfeeding/infestation sites of the field colonies. In caseof the larger field trials, up to 24 colonies per specieshad been selected, and drums filled with wood had been duginto the soil around colonies as feeding sites. Baits wereplaced on top of the infested drums and covered withplastic foil and soil. In case of the exemplary trialssingle infestation sites hâve been selected and the baitswere attached directly onto the infestation and coveredwith plastic foil and soil, or cardboard to ensure minimumdisturbance. Baits were checked after 1 to 4 days or after2 weeks, depending on species and activity. The amount ofpaper eaten and the number of termites were analysed.

As usual in natural field colonies there was astrong variation of data between colonies, therefore forstatistical analysis data had to be transformed into logand square root, respectively. In the large field trialsC. lacteus, M. darwiniensis and C. acinac if orrais had ailconsumed significantly more of the bait material and therewere more termites attracted to the baits, when hydroquinone had been applied (See Table 5). The exemplarytests with C. frenchi, S. actuosus, C. travians and C.curvignathus ail indicated increased feeding activity ontreated baits over control baits (See Table 6). Tests with N. exitiosus showed no feeding activity even after longexposure, due to the difficult dietary preferences of thisspecies. However, we could still show increased termitepresence in treated baits compared to control baits (SeeTable 6). We therefore conclude that hydroquinone in factacts also under natural conditions in the field as strongand effective attractant and feeding stimulant on varioustermite species, when added to baits. 19 118 14

Table 5 : Field baiting trials with Coptotermes lacteus(ACT), Coptotermes acinaciformîs (NT) and Mastotermesdarwinïensis (NT). (W): Amount bait material eaten [g] and 5 (No): nuraber of termites [N} in baits, comparing baits treated with 20pg hydroquinone to control baits (mean ± SE,Paired Samples T-test, ***: significant différence atp<0.001, data transformed to log or sqrt for statisticalanalysis).

Species Trial N Treated Bait Control Bait P C. lacteus 3 days 17 W[g] No [N] 0.39240.156 0.18140.099 W ★ * 269.74169.1 198.94147.7 M.darvriniensis 2 days 12 W[g) No [N] 0.76640.164 0.36840.126 ** 18.543.6 7.742.9 * * C.acinaciformis 2 days 16 W[g] No [N] 0.05640.010 0.0354008 * * 120.6429.5 84.1420.0 *** 10

Table 6 : Exemplary field baiting trials with Coptotermesfrenchi (ACT), Schedorhînotermes actuosus (NT), Coptotermestravians (Malaysia), Coptotermes curvignathus (Malaysia)and Nasutïtermes exitiosus (NSW). Proportion bait material 15 eaten [%] or termite presence, respectively, comparingbaits treated with 20pg hydroquinone to control baits.

Species Trial n Proportion eaten/termite Proportion eaten/termite presence (control bait) presence bait) (treated C. frenchi 2 weeks 3 30¾ 5% 90% 0% 3 0% 0% S. actuosus 4 days 1 5% 0% C. travians 1 âay 2 20% 20% 60% 40% C. curvignathus 1 day 3 95% 20% 50% 5% N. exitiosus 2 weeks 4 Termites présent Not touched 20

Termites présent Not touched Termites présent Not touched Termites présent Not touched

INDUSTRIAL APPLICABILITE

The compounds of the présent invention are usefulin stimulating feeding activity in termites so as to 5 enhance the effectiveness of termite baits.

Claims

21 118 14 CLAIMS THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS;

1. A feeding stimulant for stimulating feedingactivity in termites, comprising an effective amount of acompound capable of stimulating feeding activity intermites, said compound having at least two OR groups, eachof which is a substituent of an aryl moiety, and R ishydrogen or an organic group, and addition compoundsthereof, and a biologically acceptable carrier and/orextender.
2. A feeding stimulant as claimed in claim 1 whereinat least one R is an organic group and said compound hasfeeding stimulating activity.
3. A feeding stimulant as claimed in claim 2 whereinsaid organic group is selected from the group consisting ofalkyl, substituted alkyl, aryl, substituted aryl, aralkyland substituted aralkyl.
4. A feeding stimulant as claimed in claim 1 whereinat least one R is an organic group and said compound is aprecursor of a compound with feeding stimulating activity.
5. A feeding stimulant as claimed in claim 4 whereinsaid compound is hydrolysed to a compound in which said atleast one R is hydrogen. 22 118 14
6. A feeding stimulant as claimed in claim 5 whereinsaid organic group is a carbohydrate moiety.
7. A feeding stimulant as claimed in claim 6 whereinsaid compound is β-arbutin.
8. A feeding stimulant as claimed in claim 1 whereinsaid aryl group is a benzene ring substituted by said atleast two OR groups.
9. A feeding stimulant as claimed in claim 8 whereinsaid compound has the following general formula I:

wherein Ri is selected from the group consistingof hydrogen, alkyl, substituted alkyl, aryl, substitutedaryl, aralkyl and substituted aralkyl; R2, R3, R4, R5 and R6 are independently selectedfrom the group consisting of hydrogen, hydroxyl, alkyl,substituted alkyl, alkoxy, substituted alkoxy, aryl,substituted aryl, aryloxy, substituted aryloxy, aralkyl,substituted aralkyl, aralkyloxy and substituted aralkyloxy,or R2 and R3 together, R3 and R4 together, R4 and R5 togetherand/or R5 and R6 together form an aryl group; provided only that least one of R2, R3, R4, R5 orRê is hydroxyl, alkoxy, substituted alkoxy, aryloxy,substituted aryloxy, aralkyloxy or substituted aralkyloxy.
10. A feeding stimulant as claimed in claim 9 wherein Ri is selected from the group consisting of hydrogen,alkyl, aryl and aralkyl. 23 118 14
11. A feeding stimulant as claimed in claim 10wherein Ri is selected from the group consisting ofhydrogen, methyl, ethyl, phenyl and benzyl.
12. A feeding stimulant as claimed in claim 11wherein Ri is hydrogen.
13. A feeding stimulant as claimed in claim 9 whereinR2, R3, R4, Rs and R6 are independently selected from thegroup consisting of hydrogen, hydroxyl, alkyl, alkoxy,aryl, aryloxy, aralkyl, and aralkyloxy.
14. A feeding stimulant as claimed in claim 13wherein R2, R3, R4, R5 and R6 are independently selectedfrom the group consisting of hydrogen, hydroxyl, methyl,ethyl, methoxy, ethoxy, phenyl, phenoxy, benzyl andbenzyloxy.
15. A feeding stimulant wherein R2 or R6 is hydroxyl.
16. A feeding stimulant wherein R3 or R5 is hydroxyl. as claimed in claim 14 as claimed in claim 14
17. A feeding stimulant wherein R4 is hydroxyl. as claimed in claim 14
18. A feeding stimulant as claimed in claim 1 wherein said compound is selected from the group consisting of: p-hydroquinonequinhydronecatecholresorcinolphloroglucinol 4-methoxyphenolmethoxyhydroquinone 1,4-dimethoxybenzene 24 113 14 4-phenoxyphenolphenylhydroquinone4-benzyloxyphenol
19. A feeding stimulant as claimed in claim 1 whereinsaid compound has a plurality of aryl moieties.
20. A feeding stimulant as claimed in claimed 19wherein each said aryl moiety is a benzene ring.
21. A feeding stimulant as claimed in claim 20wherein said compound is a polyphenylether.
22. A method of stimulating feeding activity intermites, comprising the steps of: (1) providing a feeding stimulant as claimedin any one of daims 1 to 21; and (2) applying said feeding stimulant to a locus.
23. A method as claimed in claim 22 further comprising the step of providing a food source at saidlocus.
24. 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 claimedin any one of daims 1 to 21; and (3) applying said feeding stimulant to said locus.
25. A bait for attracting termites, comprising: (1) a food source; and (2) a feeding stimulant as claimed in any oneof daims 1 to 21. « 11814
26. A bait as claimed in claim 25 wherein said foodsource is a source of cellulose.
27. A bait as claimed in claim 26 wherein said foodsource is selected from the group consisting of paper,cardboard, canite, chipboard, Sound wood and fungallydecayed wood.
28. A bait as claimed in any one of daims 25 to 27further comprising a termiticidal substance.
29. A bait as claimed in claim 28 in which saidtermiticidal substance is a chitin synthesis inhibitor oran insect growth regulator.
30. A bait as claimed in any one of daims 25 to 29further comprising an antioxidant.
31. A bait as claimed in any one of claims 25 to 30further comprising a synergist and/or other attractants.
32. A bait as claimed in any one of claims 25 to 31further comprising nutrients such as nitrogen-containingcompounds and carbohydrates.
33. A termiticidal composition comprising: (1) a termiticidal substance; and (2) a feeding stimulant as claimed in any oneof claims 1 to 21.
34. A termiticidal composition as claimed in claim33 wherein said termiticidal substance is a chitinsynthesis inhibitor or insect growth regulator.
35. A compound having at least two OR groups, eachof which is a substituent of an aryl moiety, and R ishydrogen or an organic group, and addition compounds 113 14 26 thereof, when used for stimulating feeding activity intermites.
36. A compound as claimed in daim 35 of generalformula I as defined in daim 9.
37. A compound having at least two OR groupe, each ofwhich is a substituent of an aryl moiety, and R is hydrogenor an organic group, and addition compounds thereof, whenused in an amount effective to stimulate feeding activityin termites to attract termites to a locus.
38. A compound as claimed in daim 37 of generalformula I as defined in daim 9.
39. The use of a compound having at least two ORgroups, each of which is a substituent of an aryl moiety,and R is hydrogen or an organic group, and additioncompounds thereof, in stimulating feeding activity intermites.
40. The use of a compound as claimed in claim 39wherein said compound is of general formula I as defined inclaim 9.
41. The use in an amount effective to stimulatefeeding activity in termites of a compound capable ofstimulating feeding activity in termites, said compoundhaving at least two OR groups, each of which is asubstituent of an aryl moiety, and R is hydrogen or anorganic group, and addition compounds thereof, to attracttermites to a locus.
42. The use of a compound as claimed in claim 41wherein said compound is of general formula I as defined inclaim 9. 27 118 14
43. The use in an amount effective to stimulatefeeding activity in termites of a compound capable ofstimulating feeding activity in termites in the manufactureof a bait for attracting termites, said compound having atleast two OR groups, each of which is a substituent of anaryl moiety, and R is hydrogen or an organic group, andaddition compounds thereof.
44. The use of compound as claimed in claim 43wherein said compound is of general formula I as defined inclaim 9.
45. The use in an amount effective to stimulatefeeding activity in termites of a compound capable ofstimulating feeding activity in termites in the manufactureof a termiticidal composition, said compound having atleast two OR groups, each of which is a substituent of anaryl moiety, and R is hydrogen or an organic group, andaddition compounds thereof.
46. The use of a compound as claimed in claim 45wherein said compound is of general formula I as defined inclaim 9.
47. A method of stimulating feeding activity intermites, comprising the steps of: (1) providing a compound effective instimulating feeding activity in termites having at leasttwo OR groups, each of which is a substituent of an arylmoiety, and R is hydrogen or an organic group, and additioncompounds thereof; and (2) applying said compound to a locus.
48. A method as claimed in claim 47 wherein at leastone R is an organic group and said compound has feedingstimulating activity. 28 118 14
49. A method as claimed in claim 48 wherein saidorganic group is selected front the group consisting ofalkyl, substituted alkyl, aryl, substituted aryl, aralkyland substituted aralkyl.
50. A method as claimed in claim 47 wherein at leastone R is an organic group and said compound is a precursorof a compound with feeding stimulâting activity.
51. A method as claimed in claim 50 wherein saidcompound is hydrolysed to a compound in which said at leastone R is hydrogen.
52. A method as claimed in claim 51 wherein saidorganic group is a carbohydrate moiety.
53. A method as claimed in claim 52 wherein saidcompound is β-arbutin.
54. A method as claimed in claim 47 wherein saidcompound has an aromatic nucléus substituted by said atleast two OR groups.
55. A method as claimed in claim 54 wherein saidcompound has the following general formula I:

wherein Ri is selected from the group consistingof hydrogen, alkyl, substituted alkyl, aryl, substitutedaryl, aralkyl and substituted aralkyl; R2, R3, R4/ R5 and R6 are independently selectedfrom the group consisting of hydrogen, hydroxyl, alkyl, 29 118 14 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 togetherand/or R5 and R6 together form an aryl group; provided only that least one of R2, R3, R4, R5 orR6 is hydroxyl, alkoxy, substituted alkoxy, aryloxy,substituted aryloxy, alkaryloxy or substituted alkaryloxy.
56. A method as claimed in claim 55 wherein Ri isselected from the group consisting of hydrogen, alkyl, aryland alkaryl.
57. A method as claimed in claim 56 wherein Ri isselected from the grôup consisting of hydrogen, methyl,ethyl, phenyl and benzyl.
58. A method as claimed in claim 57 wherein Rx ishydrogen.
59. A method as claimed in claim 54 wherein R2, R3, R4, R5 and R6 are independently selected from the groupconsisting of hydrogen, hydroxyl, alkyl, alkoxy, aryl,aryloxy, alkaryl, and alkaryloxy.
60. A method as claimed in claim 58 wherein R2, R3, R4, R5 and R6 are independently selected from the groupconsisting of hydrogen, hydroxyl, methyl, ethyl, methoxy,ethoxy, phenyl, phenoxy, benzyl and benzyloxy.
61. A method as claimed in claim 60 wherein R2 or R6is hydroxyl.
62. A method as claimed in claim 60 wherein R3 or R5is hydroxyl.
63. A method as claimed in claim 60 wherein R4 is 30 118 14 hydroxyl.
64. A method as claimed in claim 47 wherein saidcompound is selected from the group consisting of: 5 p-hydroquinone quinhydronecatecholresorcinolphloroglucinol 4 -methoxyphenol methoxyhydroquinone1,4 -dimethoxybenzene4-phenoxyphenolphenylhydroquinone 4-benzyloxyphenol
65. A method as claimed in claim 47 wherein saidcompound has a plurality of aryl moieties. 20 66. A method as claimed in claimed 42 wherein each said aryl moiety is a benzene ring.
67. A method as claimed in claim 43 wherein said compound is a polyphenylether.