AP1174A

AP1174A - Termite Control

Info

Publication number: AP1174A
Application number: APAP/P/1998/001424A
Authority: AP
Inventors: Villiers Vivian De; Ernest Jacobus Robbertse; Der Westhuizen Michael Christiaan Van
Original assignee: Bayer Ag; Bayer Pty Ltd
Priority date: 1997-12-30
Filing date: 1998-12-28
Publication date: 2003-06-30
Also published as: BR9805735A; MY157868A; ZA9711701B; ID21614A; AP9801424A0

Abstract

The present invention is concerned with the control of harvester termites of the order isoptera and the species hodotermidae spp. By using bait compositions comprising agonists or antagonists of the nicotinergic receptors of insects and carriers form palitable grass or lucerne particles.

Description

Termite Control

The present invention is concerned with the control of harvester termites of the order Isoptera and the species Hodotermidae spp. by using bait compositions comprising agonists or antagonists of the nicotinergic acetyicholin receptors of insects and carriers from palitable grass or luceme particles. ·

The use of agonists or antagonists of nicotinergic acetyicholin receptors of insects against material damaging termites is known. But the methods useful in protecting technical material could not be used when it comes to the protection of green fields against the attack from harvester termites. Harvester termites live underground. They feed their imature stages with stuff they prepare from fermentation of parts of green plant material harvested above ground and carried underground into their rests.

For this the adults forage in the surroundings of their subterraneous burrow and carry back plant parts they cut from plants they find. Thus damage is done especially to pastures, lawn, golf courses, fields etc.

Conventional treatment is difficult because it would mean to treat the insects and their immature stages in their burrow. As the burrows could extend over many thousands of square meters and often beyond the area where damage is observed it is not possible to use the methods developed for combating material damaging termites.

It has now been found that based upon active compounds from the agonists or antagonists of nicotinergic acetyicholin receptors of insects also known as nicotinolcompounds, mostly nitromethylene-, nitroguanidine-, cyanomethylene-, cyanoguanidine-compounds termite control could be achieved with a bait system.

Subject of the present invention is

1. Use of agonists or antagonists of nicotinergic acetyicholin receptors of insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp.

APO η11 γ 4

2. Use of agonists or antagonists of nicotinergic acetylchoiin receptors of insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp. in the form of baits comprising the active compounds and particles of palitable grass or lucerne and optionally usual formulating additives.

3. Use of agonists or antagonists of nicotinergic acetylchoiin receptors of insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp. in the form of bait material which is applied broadcast on the surface of the soil where the termites are foraging.

4. Bait for use of agonists or antagonists of nicotinergic acetylchoiin receptors of insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp. characterized that it comprises the active compounds and as carrier particles of grass or lucerne and optionally usual formulation additives.

5. Bait according to 4 characterized that It contains active compound in a con20 centration of 0,001-1% by weight and the carrier in a concentration of

94-99.99 % by weight and optional formulation additives up to 5 % by weight.

Agonists and antagonists of nicotinergic acetylchoiin receptors of insects are known compounds.

They are disclosed, for example in European Offeniegungsschriften No. 464 830, 428 941, 425 978, 386 565, 3S3 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389; German Offeniegungsschriften No.

3 639 877, 3 712 307; Japanese Offeniegungsschriften No. 03 220 176, 02 207 083,

307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, US Patent Specifications No. 5 034 524, 4 948 798, 4 918 086, 5 039 686, 5 034 404; PCT

AP/r/ 9 8 / 0 1 4 2 4

23APO 0 117 4

-3 Applications No. WO 91/17 659, 91/4965; French Application No. 2 611 114; Brazilian Application No. 88 03 621.

Reference is made expressly to the methods, processes, formulae and definitions de5 scribed in these publications and to the individual preparations and compounds described therein.

These compounds may preferably be represented by the general formula (I) (A)

II io ^X“^E in which

R represents hydrogen, optionally substituted radicals from the group consisting 15 of acyl, alkyl, aryl, aralkyl, heteroaryl or heteroarylalkyl;

A represents a monofunctional group from the series consisting of hydrogen, acyl, alkyl and aryl, or represents a bifunctional group which is linked to the radical Z;

E represents an electron-attracting radical;

X represents the radicals -CH= or =N-, it being possible for the radical -CH= to be linked to the radical Z instead of an H atom;

Z represents a monofunctional group from the series consisting of alkyl, -O-R,

-S-R and

R /

-N

R

AP/P/ 9 8 / 0 1 4 2 4

23-.

AP 0 0 117 4

- 4 or represents a bifiinctionai group which is linked to the radical A or the radical X.

Particularly preferred compounds of the formula (I) are those in which the radicals have the following meanings:

R represents hydrogen and optionally substituted radicals from the series consisting of acyl, alkyl, aryl, aralkyl, heteroaryl and heteroasylalkyl.

Acyl radicals which may be mentioned are formyl, alkylcarbonyl, arylcarbonyl, alkylsulphonyl, arylsulphonyl or (alkyl-)-(aryl-)-phosphoryt all of which may, in turn, be substituted.

Alkyl which may be mentioned is Cj.^o-alkyl, in particular Cj^-alkyi, specifically methyl, ethyl, i-propyl and sec- or t-butyl, all of which can, in turn, be substituted.

Aryl which may be mentioned is phenyl or naphthyl, in particular phenyl.

Aralkyl which may be mentioned is phenylmethyl or phenethyl.

Heteroaryl which may be mentioned is heteroaryl having up to 10 ring atoms and N, O, S, in particular N, as hetero atoms. The following may be mentioned specifically: thienyl, furyl, thiazolyl, imidazolyl, pyridyl and benzothiazolyl.

Heteroarylalkyl which may be mentioned is heteroarylmethyl or heteroarylethyi having up to 6 ring atoms and N, O, S, in particular N, as heteroaioms. The following may be mentioned specifically: pyridylmethyl, thiazolyl30 methyl, furylmethyl which are optionally substituted.

The following substituents may be mentioned by way of example and as being preferred:

AP/P/ 9 8 / 0 1 4 2 4

23-0

APO Ο 117 4

- 5 alkyl having preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methyl, ethyl, n- and i-propyl and η-, 1- and t-butyl; alkoxy having preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n- and ipropyloxy and η-, i- and t-butyloxy; alkylthio having preferably 1 to 4, in par5 ticuiar 1 or 2, carbon atoms, such as methylthio, ethylthio, n- and i-propylthio and η-, i- and t-butylthio; halogenoalkyl having preferably 1 to 4, in particular or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3, halogen atoms, the halogen atoms being identical or different, and preferred halogen atoms being fluorine, chlorine or bromine, in particular fluorine, such as trifluoro10 methyl; hydroxyl; halogen, preferably fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl- and dialkylamino having preferably 1 to 4, in particular 1 or 2, carbon atoms per alkyl group, such as methylamino, methyi-ethyl-amino, n- and i-propylamino and methyl-n-butylamino; carboxyl; carbalkoxy having preferably 2 to 4, in particular 2 or 3, carbon atoms such as carbomethoxy and carboethoxy; sulpho (-SO₃H); alkylsulphonyl having preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methylsulphonyi and ethylsulphonyl; arylsulphonyl having preferably 6 or 10 aryl carbon atoms, such as phenylsulphonyi, and also heteroarylamino and heteroarylalkylamino, such as chloropyridylamino and chlo20 ropyridyimethylamino.

A particularly preferably represents hydrogen and also optionally substituted radicals from the series consisting of acyl, alkyl and aryl, ail of which preferably have the meanings given in the case of R. A furthermore represents a bifunctional group. The following group may be mentioned; optionally substituted alkylene having 1-4, in particular 1-2, C atoms, suitable substituents which may be mentioned being those listed further above and it being possible for the alkylene groups to be interrupted by one or more hetero atoms from the series consisting of N, 0 and S.

A and Z together with the atoms to which they are bonded can form a saturated or unsaturated heterocyclic ring. The heterocyclic ring can contain a further 1 or identical or different hetero atoms and/or hetero groups, hetero atoms are

AP/P/ 98/01424

APOO1174

- 6 preferably oxygen, suiphur or nitrogen, and hetero groups are N-alkyl, the alkyl of the N-alkyl group preferably containing 1 to 4, in particular 2 or 2, carbon atoms. Alkyl which may be mentioned is methyl, ethyl, n- and i-propyl and η-, i- and t-butyl. The heterocyclic ring contains 5 to 7, preferably 5 or 6, ring members.

Examples of the heterocyclic ring which may be mentioned are pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-1,3,5-triazine and morpholine, all of which can optionally be substituted, preferably by methyl.

E represents an electron-attracting radical, radicals which may be mentioned being, in particular, NCE, CN and halogenoalkylcarbonyl such as 1,5-halogeno-Ci_4-carbonyl, in particular COCF₃.

X represents-CH= or-N-.

Z represents optionally substituted radicals alkyl, -OR, -SR and -NRR, R and the substituents preferably having the abovementioned meaning.

Z can not only form the abovementioned ring, but can also, together with the atom to which it is bonded and X forming the radical =C — form a saturated or unsaturated heterocyclic ring. The heterocyclic ring can contain a further 1 or 2 identical or different hetero atoms and/or hetero groups. Hetero atoms are preferably oxygen, sulphur or nitrogen, and hetero groups are N-alkyl, the alkyl or N-alkyl group preferably containing i to 4, in particular 1 or 2, carbon atoms. Alkyl which may be mentioned is methyl, ethyl, n- and i-propyl and η-, i- and t-butyl. The heterocyclic ring contains 5 to 7, preferably 5 or 6, ring members.

*2*10/86 /d/dV

Examples of the heterocylic ring which may be mentioned are pyrrolidine, piperidine, piperazine, hexamethyleneimine, morpholine and N-methylpiperazine.

23-(

APO 0 117 4

-7 The compounds of the general formulae (II) and (III) may be mentioned as compounds which can be used very particularly preferably according to the invention:

Subst.

QN —'

C /-(CH₂)_n-N .(A)

X-E

Subst.

.(A) (CH,) -/ /(2)

X-E (II), (III), in which n represents 1 or 2,

Subst. represents one of the abovementioned substituents, in particular halogen, very particularly chlorine, and

Z, X and E have the abovementioned meanings.

The following compounds may be mentioned specifically.

AP/P/ 9 8/01424

23APO 0 117 4

-8CH, r ί

Ν N — CHN·

CH,

S

CH,

NO,

Cl

A

N N II

N.

•CH, 'NO,

* 2 * I 0 / 8 6 Zd/dV

23-OK·;

A

no₂

ch₃

CH

I no₂

AP/P/ 9 8 / 0 1 4 2 4

CH, — N NH

Y

NO,

CH

NO,

CH₂ - NH . NHCH₃ no₂

Particularly preferred are the following compounds:

•CH,

N NH H

CH ''NO,

APO 0 117 4

^NO2

NO4

Imidacloprid

Nitenpyram

Acetamiprid

Cl —(\

Ν' ch₂-n ch₃

I ³

A

N-CH, ch₂- n

Ci

N-NO,

Η H .N-CH. II

N-NONA

CK₂ -NN- CH₃

N-NO.

AP/P/ 9 8 / 0 1 4 2 4

Termites to be combated by the present method are those of the order of isoptera and family of acrididae especially mentioned are Hodotermidae spp.

The carrier material on which the inventive baits are based is preferably chopped or shredded grass, cereal, corn, lucerne. The plant particles could be used freshly produced or in dried form.

Particles of dry lucerne hay, dry wheat straw or any palatable grass species could also be used.

The material should preferably be chopped in little sticks 5 to 20 mm in length, 1 to 3 mm thick and the bulk of density of the bait material will depend on the type of material used.

23-CT

AP001174

- 11 Concentration of the active compound is 0.001-1 % by weight, preferably 0.005-0.5 % by weight.

The bait formulations may be produced in known manner, for example by mixing the 5 active compounds with the carrier material, optionally with the use of additives such as surface-active agents, that is to say emulsifying agents and/or dispersing agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. The active compounds might be used as such or in the form of solutions or suspensions in liquid solvents. As such are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethyiforaiajnide and dimethyl-sulphoxide, as well as water.

As emulsifying agents there may be used non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products. Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulation.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs.

AP/P/ 9 8/01424

These additives are used in concentrations of about 0.0001-0.1 % by weight, preferably 0.001-0.1 % by weight.

23APO 0 117 4

- 12 Example 1

A bait according to the invention is made by mixing 10 g Imidacloprid in circa 5 litres 5 of clean water. 10 kg of dry wheat straw (length 2 cm) is spread to a thickness of circa 2 cm over a clean surface (tarpaulen ect.). The Imidacloprid/water mixture is evenly applied by means of a spray to the surface of the carrier material. Carrier material is turned and mixed and spread out again to a thickness of circa 2 cm. This procedure is repeated until the total volume of circa 5 litres of Imidacloprid/water mixture is thoroughly blended with the carrier material.

AP/P/ 9 8/01424

Claims

Patent Claims

1. Use of agonists or antagonists of nicotinergic acetytcholin receptors of insects in the control of harvester termites from the insect order of isoptera and

5 species Hodotermidae spp.
2. Use of agonists or antagonists of nicotinergic acetylcholin receptors of insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp. in the form of baits comprising the active

10 compounds and particles of palitable grass or lucerne and optionally usual formulating additives.
3. Use of agonists or antagonists of nicotinergic acetylcholin receptors of insects in the control of harvester termites from the insect order of isoptera and

15 species Hodotermidae spp. in the form of bait material which is applied as (a strip or band) on the surface of the soil in an area which has to be protected from termite attack.
4. Bait for use of agonists or antagonists of nicotinergic acetylcholin receptors of

20 insects in the control of harvester termites from the insect order of isoptera and species Hodotermidae spp. characterized that it comprises the active compounds and particles of grass or lucerne and optionally usual formulation additives.

25 5. Bait according to claim 4 characterized that in contains active compound in a concentration of 0.001-1 % by weight and the carrier in a concentration of 94-99.99 % by weight and optional formulation additives up to 5 % by weight.