JPS63152301A - Diiodomethylsulfonic insecticide - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to insecticidal compositions containing short methylsulfone derivatives and the use of said derivatives for controlling termites, cockroaches and ants.

BACKGROUND OF THE INVENTION Subterranean termites are a significant economic problem throughout the United States, with damage and cost of control estimated to exceed $7.5 billion annually. Most of this loss has been attributed to the genus Reticulitermes, which includes most infested termites and which includes Reticulitermes virginicus.
cus) species and Reticulitermes fistulahypes (Re
ticulitermes flavipes) species. Several other subterranean termite species are also highly destructive, but their impact is limited to each termite's distribution area. For example, Heterochilmes aureus (Het.
erotermes au+'eus) is a pest that cannot be ignored in the deserts of the southwest.

Taiwan subterranean termite, Kobutotermes formosanus (C
optotermes formosanus) is found in China, Taiwan, Japan, Hawaii, Guam, the Midway Islands,
It is widely distributed in tropical, subtropical, and temperate regions of the world, including South Africa, Sri Lanka, and regions of the Americas. Within the past 30 years, Louisiana, Texas,
It has been reported to be distributed in South Carolina, Frog, Alabama, Mississippi, and Tennessee. The cost of controlling this insect in 1984 was $1.2 billion in China, $4 billion in Japan, $600 million in Hawaii, and an additional $5-6 million in the southwestern states mentioned above. . Formosan termites are extremely difficult to control and, once established, are generally considered to be the most destructive pest of buildings. It turns any cellulosic material into food. This insect is thought to attack live vegetation as well as cause significant damage to buildings and other timber such as utility poles.

The pests also attack and invade non-cellulosic materials in their path as they flock to their food, such as electrical and telephone wires, wall earth, and plastic materials.

Carpenter ants that exist in the natural environment are decomposers.

5ers) and are usually found in trees and logs. However, some species have expanded their habitats to include human-occupied wooden structures. Seventy-eight percent of the building infestations investigated in Washington state were caused by Cambonotus modoc (C.
amponotus modoc)
It was reported in 985. In the northwest, black carpenter ants (b.
lack carpenter ant) [Camponotus 0 pencil vanicus (Camponotus pen)
nsylvanicus], and the New York or red carpenter ant.
[Camponotus novaeporacensis (C, novae)
two species of P. boracensis attack wooden structures. Carpenter ants are damaging pests. 19
In 1982, it was estimated that New Chassis residents spent at least $250 million a year on controlling carpenter ants in their homes. Carpenter ants are also a major cause of damage to wooden utility poles.

Cockroaches are probably the most obnoxious insects known to humans. There is considerable evidence that many cockroach species can be considered potential vectors of disease. Cockroaches are considered disgusting invaders for a number of reasons, including that they move quickly and unpredictably, and that if left undisturbed, their populations can grow to enormous numbers. and have a habit of contaminating with their characteristic odor and smearing all food and surfaces with which they come in contact with feces. As a result, cockroaches usually result in poor standards of hygiene and their presence can be psychologically unpleasant and cause troublesome mental distress. The most prevalent cockroach in the United States is the European cockroach Blatella germani.
ca).

The insecticidal composition of the present invention can be used to kill Formosan termites, termites of the genus Reticlitermes in the United States, carpenter ants, and fusiliaris native to South America [Solenobsis saevitsushima].
It is effective in controlling other varieties of ants such as S. saevissima) as well as cockroaches.

Other insects for which the compositions of the present invention may be effective include:
Monomorium pharaonis (Mono
morium pharaonis)], Powder Post Beetle [Lyctu brunneus (Lyctu
s brunneus)] and the wood-destroying beetle [Hyloturupes bajurus]
rupes bajuluS) and Anobium punctatum]
, as well as the fungus-growing termite, an agricultural pest in Africa and India.
termites) [Macro termites]
termitinae)].

Structure and effect of the invention The insecticidal composition of the present invention has the general formula: [wherein R represents R'(CR2)n, n is 0 to 4, R1 is lower alkyl, phenyl, mono-lower alkyl Phenyl, monohalophenyl, nitrophenyl, aminophenyl, acetamido-substituted phenyl, (CH2)mCO
OH-substituted phenyl (m is 1-3), dihalo-substituted phenyl, (halo) toro) phenyl, ditro) (lower alkyl) phenyl, (halo) (lower alkyl) phenyl or di-lower alkyl substituted phenyl] This composition contains the compound represented by the following as an active ingredient, and is effectively used for controlling termites, cockroaches, and ants.

The term rl)I)ml as used herein means parts by weight of active ingredient per million parts by weight of the final product (liquid or solid form).

As used herein, the term "lower alkyl"
It means straight chain and branched C, -C5 alkyl groups.

As used herein, the term "halo" refers to C0,
Represents Br or I.

As used herein, the term dihalo-substituted phenyl J refers to a compound of the formula: where X is halo.

"(halo)nitro)phenyl" used herein
The term refers to a compound of the formula: where X is halo.

As used herein, the term "nitro)(lower alkyl)phenyl" refers to a compound of the formula: where R' is lower alkyl.

As used herein, the term "(halo)(lower alkyl)phenyl" refers to a compound of the formula:

As used herein, the term "di-lower alkyl-substituted phenyl" refers to a compound of the formula: where R' is lower alkyl.

The most preferred compound of the invention is p-tolyl short methyl sulfone.

The compounds of the invention can be used in the form of compositions. The compositions are prepared by mixing a compound of the invention with one or more inert excipients or carriers, such as adjuvants or modifiers, and are in the form of dusts, wettable powders, highly concentrated The composition can be obtained in the form of a concentrate, an aqueous or non-aqueous dispersion, or a feed. Feed formulations are prepared by combining the compounds of the invention with a liquid or solid feed source that attracts the insects targeted for control. As mentioned above, the compounds of the present invention may be used in association with carriers or excipients such as finely divided solids, organic liquids, water, wetting agents, dispersing agents, emulsifying agents, or suitable combinations thereof. I can do it. Similarly, these compounds can also be used in combination with other insecticides in a preferred embodiment.

The compositions of the present invention, particularly those in liquid and easily wettable powder form, can contain a sufficient amount of surfactant so that the compositions are readily dispersible in water or oil. In the present invention, the surfactant may be a wetting agent, a dispersing agent, or an emulsifier that assists in the dispersibility of the compound of the present invention. These surfactants can include anionic, cationic or nonionic surfactants.

Suitable surfactants that can be used in the compositions of the invention include polyethylene glycol fatty acid esters and aliphatic alkylolamide condensates, alkylaryl sulfones, fatty alcohol sulfates,
Examples include dialkyl esters of sodium sulfosuccinate, fatty acid esters of sodium isothionate, polyoxyethylene ethers and thioethers, and long-chain quaternary ammonium chloride compounds. Surface-active dispersants such as lignin sulfonates, low viscosity methyl cellulose and polymerized sodium salts of alkylnaphthalene sulfonic acids are also suitable.

Among the more preferred surfactants are anionic and nonionic types. Preferred among the anionic surfactants are alkali metal salts or amine salts of alkylbenzenesulfonic acids, such as dodecylbenzenesulfonic acid, sodium lauryl sulfate, alkylnaphthalenesulfonates, N-methyl-N-oleoyltartaric acid. These include sodium, oleate ester of sodium isothionate, dioctyl sodium sulfosuccinate, and sodium dodecyl diphenyl oxide disulfonate. Preferred nonionic compounds include alkylphenoxypoly(ethyleneoxy)ethanols such as ethylene oxide adducts of nonylphenol, and polyethylene oxides of long-chain aliphatic alcohols such as trinotylnonyl polyethylene glycol red ethers. adducts, polyethylene oxide adducts of fatty acids and rosin acids, ethylene oxide adducts of long chain alkyl mercaptans, and polyethylene oxide adducts of sorbitan fatty acid esters.

Generally, up to 10% by weight of surfactant is used in the compositions of the invention, and typically the amount of surfactant ranges from 1 to 5%, but up to 1% by weight may be used. .

The compositions of the present invention may be present in the form of easily wettable powders, concentrated suspensions, dusts, granules, emulsified concentrates, aerosols or feeds, as described above.

Of course, the appropriate dosage form and concentration of the compounds according to the invention will depend on the intended use of the composition.

Generally, termiticide compositions contain about 25% of the active ingredient.
ppm to about 4,000 ppm, and the preferred concentration for killing Reticlitermes termites is about 2
5 ppm to about 800 ppm, and the preferred concentration for killing Formosan termites is about 200 ppm to about 4,000 ppm.
m range. Cockroach-killing compositions typically contain about 10% of the active ingredient. 80. from oooppm. OOOppm
and approximately 10,000pp in an anticide composition.
m - about 40. It is contained within the range of OOOppm.

(A) Easily Wettable Powders Easily wetted powders consist of the active ingredient, an inert solid filler,
and water-dispersible compositions containing one or more surfactants to enable rapid wetting and prevent aggregation of the composition with suspended matter in the water.

The inert fillers preferred for use in the easily wettable powders of this invention can be of either mineral or non-mineral origin.

Suitable fillers for the easily wettable powders of the present invention include synthetic mineral fillers derived from natural earths, diatomaceous earths, and silicas and silicates.

Preferred fillers in the present invention include kaolinite, attapulgite earth, montmorillonite earth, synthetic silica, synthetic magnesium silicate, and double gypsum. The most preferred non-mineral filler is lactose.

Among the preferred surfactants are nonionic and anionic types. Most suitable for producing the dry, easily wettable products of this invention are solid forms of compounds known to those skilled in the art as wetting agents and dispersing agents. Liquid nonionic surfactants can also often be utilized as wetting and dispersing agents.

The most preferred wetting and dispersing agents are alkylbenzene- and alkylnaphthalene sulfonates, sulfated fatty alcohols, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, These include sulfonated petroleum ethers, sulfonated vegetable oils and di-tertiary acetylenic glycols. Preferred dispersants are methylcellulose, polyvinyl alcohol, lignin sulfonates, polymerized alkylnaphthalene sulfonates, polymethylene bisnaphthalene sulfonates, polyethylene oxide adducts of sodium N-methyl-N-(long chain acid) tartrate and sorbitan fatty acid esters. It is.

Wetting agents and dispersing agents in these preferred easily wettable powder compositions of the present invention are typically about 0.5% to 5% by weight.
be present at a concentration of An inert filler is then added to formulate the formulation. Optionally, 0.1% to 5% by weight of a bulking agent may be added to an antifoaming agent and a free flow agent.
nt) - Therefore, the easily wettable powders of the invention usually contain 25 to 90% by weight of active substance, 0.5 to 2.0% by weight of wetting agent,
It contains 0.25-5.0% by weight of dispersant and 9.25-74.25% by weight of inert filler, respectively.

If the easily wettable powder contains a superplasticizer or an antifoam agent or both, the superplasticizer may be added to the composition in an amount of about 4 to 5
An amount not exceeding 0.5% by weight of an inert filler may be included to replace an equivalent amount of an inert filler;
It is included in place of an equal amount of inert filler in an amount not exceeding .

In addition to surfactants, these compositions contain finely powdered excipients such as talc, as well as natural earths such as acpargite and kaolinite, as well as pyrophyllite, diatomaceous earth, synthetic finely divided silica, and silicic acid. Calcium, carbonate, lactose, etc. can be included.

Preferred excipients are aluminum silicate hydrate, aluminum magnesium silicate hydrate and aluminum magnesium iron silicate hydrate earth.

The amount of finely divided inert solid excipient can vary over a wide range, but is generally about 10 to 9
The range is 8% by weight.

Compositions that are easily wetted can be prepared by mixing the ingredients and applying a hammer mill or an air attrition mill.
mill) or other similar equipment. Particle size can vary over a wide range, but typically the final formulation will have a particle size of 50
Sift it so that it is less than a micron.

(B) Highly Concentrated Compositions and Aqueous Concentrated Suspensions Generally, highly concentrated compositions contain 90 to 99.5% by weight of active ingredient and 0.5 to IO% by weight of liquid or solid surfactant.
Contains. Up to about half of the surfactant can be replaced with an anti-caking agent such as synthetic silica. Such highly concentrated compositions can be used in the same manner as wettable powders, but can also be suitably used in the following formulations.

Aqueous concentrated suspensions are prepared by mixing together an aqueous slurry of water-insoluble active ingredients in the presence of surfactants, dispersants, antifoaming agents, viscosity stabilizers, etc. and then milling. Ru. This results in a concentrated slurry of fine powder, or an aqueous suspension thereof, with all particle sizes below 10 microns.

The advantage of the extremely small particle size of the active ingredient is that a very uniform application is obtained upon dilution and on spraying.

These aqueous concentrated suspensions contain 15-55% by weight of active ingredient and 40-70% by weight of water, with the balance containing surfactants, dispersants, suspending agents and antifoaming agents. contain the agent.

Suspensions in organic liquids can be prepared in a similar manner, eg by replacing water with mineral oil.

(C) Dusting Agents Dusting agents are concentrated powder compositions, characterized by free-flowing and fast-setting properties, created to be applied in dry form, so that they can easily reach areas where their presence is undesirable. is not carried by the wind. It firstly contains the active substance and secondly the thick, free-flowing solid bulking agent.

The performance of the formulation may be improved by the inclusion of wetting agents, and for ease of handling, inert, absorbent grinding aids are frequently included. For the dusting compositions of the present invention, the inert bulking agent may be either vegetable or mineral, the wetting agent preferably anionic or non-ionic, and a suitable absorption agent. The grinding aid is of mineral origin.

The types of inert solid fillers suitable for dusting agent applications are organic or inorganic powders with a dense volume and are highly flowable. They are also characterized by a relatively small surface area and have poor liquid absorption performance. Suitable types of grinding aids are natural earths, diatomaceous earths, and synthetic mineral fillers obtained from silica or silicates.

A preferred inert solid filler for the dusting agent of the present invention is micaous talc.
C), pyrophyllite, kaolinite and rich kaolin soil, “
Tobacco powder and granular phosphorite, known as Phosphodust J.

Preferred grinding aids are attapulgite earth, silica, synthetic finely divided silica, and synthetic calcium and magnesium silicates.

Preferred wetting agents are those already mentioned in the section on easily wettable powders.

The inert solid fillers in the dusting agents of the present invention are usually present at a concentration of about 30-90% by weight of the total weight of the composition. Grinding aids are typically included at about 5-50% by weight of the composition and wetting agents are included at about 0-1.0% by weight of the composition. The dust composition may also contain other surfactants, such as dispersants, at concentrations up to about 0.5% by weight.

The easily wettable powders already mentioned can also be used for the production of dust formulations. The easily wettable powders mentioned above can be used directly to give dusts, and it is more convenient to dilute them to give dusts by mixing them with thick dusty excipients.

In this method, dispersants and antifoaming agents can also be included as components of the dusting agent.

Thus, the dusting agent composition of the present invention typically comprises about 5 to 20% by weight of active substance and 5 to 50% by weight of absorbent filler.
It contains 0-1.0% by weight of a wetting agent and about 30-90% by weight of a thick, free-flowing, dusty excipient. Furthermore, such dust formulations may contain small amounts of dispersants and antifoaming agents derived from the easily wettable powder used to produce the dust.

(D) Granules The composition can also be formulated into granules.

Such compositions typically contain 65-99% by weight of excipient and 1-35% by weight of active ingredient. In producing granules, the compound of the present invention is dissolved in a solvent,
The resulting solution is sprayed onto previously prepared clay-like granules and dispersed over vermiculite or similar stone, and the resulting mixture is then stirred to disperse the active ingredient throughout the mass of granules. let The particle size of such granules can range from +60 mesh to +4 mesh, and the active ingredient content is preferably from 1 to 6% by weight. Granules of smaller size are manufactured in a similar manner from appropriately designed equipment. Such granules can also be produced by mixing a finely powdered excipient and a finely powdered compound; for example, by pulverizing them together;
Granules can then be produced by adding water and subjecting the resulting spheres to a rotary dryer. Additionally, they may be prepared by mixing the finely divided compound with a granular carrier such as attapulgite or vermiculite and then spraying over the whole with a non-volatile liquid to bind the active ingredient to the carrier component.

(E) Concentrated suspension agent Concentrated suspension agent is prepared by soaking and pulverizing each component (wet-mi 11
ing), e.g. ball milling or sand milling (s
and-grinding), which makes it possible to obtain a good dispersion of the fine particles of the active compound within the scope of the invention in the excipient. Typically, such compositions contain 15-50% by weight of active ingredient and are characterized by total particle diameters of 10 microns or less.

(F) Emulsifying Suspension Water-emulsifying oil compositions can also be used with one or more of the compounds of this invention. In these compositions,
Using surfactants and oils, we create liquids that are easy to pour and measure. In use, these liquid concentrates can be mixed with water. Such compositions are difficult to use, since oil often acts as an inhibitor of foam formation.
This is advantageous in that it reduces the tendency for undesirable foam formation due to the use of large amounts of surfactants. These oil preparations contain finely powdered compounds dispersed in an insoluble carrier. An insoluble carrier is an oil in which the compound has a low solubility, e.g.
It is an oil that dissolves only at % or less. Examples of such insoluble carriers include many aliphatic hydrocarbon oils, vegetable oils and mineral oils.

In these emulsified oil suspensions, the compounds are present in amounts ranging from 5 to 35% by weight. Upon application, the oil suspension is diluted by mixing with water so that the active ingredient is present at 0.5-2% by weight in the final formulation.

(G) Aerosols Yet another liquid formulation convenient for small-scale applications is an aerosol formulation, which is compressed and sealed in a suitable container. The liquid phase can be a suspension, emulsion or solution. For ease of manufacture and use,
A solution is preferred. Pressure can be obtained by low boiling liquids, such as propane or chlorofluorocarbons, or by using relatively insoluble gases, such as carbon dioxide or nitrous oxide. Chlorofluorocarbons are preferred to eliminate flammability and to combine easily soluble powders.

It is preferred that the active ingredients remain fully soluble in the total solution formulation at 0°C or a lower storage temperature at which long-term storage can theoretically be expected. To ensure this, amphoteric solvents may be included in the formulation, which may be water-miscible even in emulsified concentrates.

Organic liquids suitable for preparing solutions, suspensions and emulsified concentrates of the compounds of the invention include alcohols, glycerols, mono- and dialkyl ethers of ethylene glycol and their derivatives, calpitols, ketones,
These include esters, sulfoxides, sulfones, sulfamides, amides, paraffin hydrocarbons, aromatic hydrocarbons, and halogenated hydrocarbons.

(H) Feed formulations Feed formulations incorporate the active ingredients into products that are likely to attract insects, such as certain forms of feed sources (liquid or solid).
It can be manufactured by mixing with

For example, for termites, a piece of wood is impregnated with a solution of the compound. Sometimes partially rotted wood is also preferred, or paper or pole paper.

27-1 Preparation examples and test examples of the composition of the present invention are shown below.

Example 1 Preparation of p-tolyl-short methyl sulfone This compound was prepared in reference to US Pat. No. 3,615,745 (1
issued October 26, 1971), U.S. Patent No. 365,735
No. 3 (issued April 18, 1972) and U.S. Pat.
No. 663623 (published May 16, 1972).

Generally, the compounds of the invention are prepared by halogenating R-sulfonylacetic acid with sodium hypohalite in an alkaline aqueous solution followed by decarboxylation. This reaction is shown by the following formula.

R-5-C-C-〇Na+2NaOX I 1 OH → R-5-CH
T) (Threnobsis invicta bren) poison bait test: The test was carried out using disposable plastic drug cups (top diameter 4
0 mm, a conical shape with a bottom diameter of 32 mm and a height of 38 mm). Drill a hole in the bottom of each cup (6 m diameter)
m) and place a dental lab stone (dent
al 1abstoneXRanson Randol
ph Co.

Inject a layer made by Toledo, OH).

Cover the hole with this rubstone and saturate its cup 1/4″
When installed on the foam pad, it functions as a wick that absorbs water. The cup was placed in a tray and covered with a transparent glass sheet to prevent water from evaporating quickly from the foam pad. High humidity had to be maintained in the cup, which prevented the ants from drying out.

Twenty worker ants selected from a laboratory colony that had been deprived of food for 14 days were placed in the test chamber approximately 24 hours before the start of the test. This pretreatment period calmed the ants and directed them toward the container. Only worker ants collected from the reared cells containing eggs were subjected to the test.

p4 Reloujode methyl sulfone (prepared in Example 1)
A fixed amount of was directly dissolved in the diet (single refined soybean oil).

A cotton sponge saturated with the poison solution was placed in a test chamber in a small vial cup, on which an ant was placed and the poison solution was given to the ant.

The ants were given free access to poisoned food for 24 hours. The poisoned bait was then removed from the test chamber and the ants were kept for an additional 24 hours without food. A new vial cup containing a cotton sponge saturated with soybean oil was then placed in the test chamber and left for the remainder of the test period. 1.2.3.6.8, IO and 1 after the start of the test
The number of deaths was counted on the 4th day. Each test was performed three times.

Room temperature was maintained at 80±2°F.

The results are shown in Table 1.

31 - Example 3 Carpenter Ant (Camponotus pensylvanicus and Novaeporacensis) Selection Test: A laboratory colony of carpenter ants was placed in a plastic 9' x 12" shoe box. The measuring section of the box was coated with liquid Teflon non-stick. Each box contained a large test tube with a wet cotton plug as a nest in the bottom.The box was covered and placed in an incubator at 22°C for 12- It was subjected to a 12 hour light-dark cycle.

A 50:50 mixture of wild flower nectar and distilled water (hereinafter referred to as
(denoted as honey water) was prepared. A fine aqueous suspension of p-1 lyludiiodomethylsulfone (Example 1) was prepared as described in section (B).

Since honey water and aqueous suspensions are both viscous substances and cannot be measured accurately with a pipette, the following method was adopted in this experiment. Empty sterile polystyrene petri dish (dimensions 100 m)
The weight of the container was measured using a Mettler scale.

The p-tolyl-short methyl sulfone was placed on a plate and weighed. Next, honey water was added and the total weight was measured. The mixture was stirred and drawn onto a 1" x 1" square cellulose sheet.

The treated cellulose cubes were placed on one half of the bedding dish, and the cellulose cubes that had simply absorbed honey water were placed on the other half. The number of foraging workers on each side was counted every minute or every 5 minutes for 25 minutes, depending on the activity of the ants.

The following processing was performed.

In test 1, 14 Cambotus novaeporacensis workers were used. Six ants spend time on the processing side,
Eleven animals spent time on the non-treated side.

The ants appeared to sense something about the treatment, as they approached the cellulose as usual, but ate only a small amount of food.

Tests 2 and 3 both used 15 Nova Evora sensis workers. In neither test did the ants show any hesitation towards the treated food.

Seven ants in Test 2 were on the treated side and 10 were on the non-treated side. In Study 3, two animals spent time on the treated side and three animals spent time on the non-treated side.

Test 4 used 10 Camponotus pensylvanicus workers. The ants did not show any preferential behavior, with 9 ants spending time on the treated side and 6 on the non-treated side.

From the above, p-tolyl-short methyl sulfone about 15
It is concluded that treatment with honey water containing ,000 ppm is suitable for laboratory tests.

Example 4 Carpenter Ant Laboratory Test One colony of A. pennsylvanicus (colony 1) and five colonies of A. novaevorasesis (colony-2 to 6) were reduced to approximately 200 workers. Each of these colonies was fed a Petri dish containing treated cellulose sheets. One colony was fed honey water containing more than 15,000 ppm of p-tolyl-short methyl sulfone for comparison. Treatments were removed after one week and normal honey water and cicada pupae were fed for the remainder of the study.

The following processing was performed.

The results are shown in Table 2.

Basically, the entire colony died. Control colonies kept in the same incubator did not die at all. The smaller workers (the minority) died first, and the larger workers, the majority, lived longer.

Female worker ants were always among the last to survive.

Example 5 Test against Formosan termites: 100 Coptotermes formosanus collected from a wild colony in Balrampur, Florida were treated with the compound of Example 1 at 0.1,000.2°000 and 4.0
Filter paper (Whitm
an No. 1, 5, 5 cm). Three replicates of each treatment were prepared for a total of 12 experimental units. All units were held at 29±1'C for 24 hours. p-Tolyl-short methyl sulfone (prepared in Example 1) was gavaged for 24 hours before being transferred to a Petri dish containing untreated filter paper moistened with deionized water. ■ Observations were made every day for 7 days, and dead and dying ants were counted and removed from the Petri dish. Mortality of worker ants was evaluated using a response variable.

The results are shown in Table 3. The control mortality rate was 1 after 17 days.
It was 5.0±4.2%. Mortality with the test compound was concentration dependent, and K. formosanus was characterized by a delayed effect.

This delayed or latent effect is a particularly important factor in termiticidal effectiveness. Like ants and bees, termites are gregarious insects that live in complex, ordered communities. Warrior insects are fed and cared for by worker insects, so a slow-acting termite killer is better than a fast-acting one.

This allows termites exposed to the poison to live long enough to return to their own termite colony, where they feed and care for other termites. Additionally, fast-acting poisons will produce a repellent response, shielding or repelling live termites from treated areas containing large numbers of dead termites.

401 Example 6 Study of local toxicity and mortality time (Kobutotermes formosanus shiraki): Thirty Formosan subterranean termite workers were pre-anaesthetized with carbon dioxide gas for 20 seconds, and then p-tolyl-short methyl Sulfone from O to 4,000ppm-(400p
increase by pm) and 6,000 to 10,000 ppm
A 0.5 μQ drop of an acetone solution containing a concentration of (increased by 2,000 ppm) was inoculated. Micro applicator (
Model M, Instrumentation
The solution was administered to the abdomen of the insect using a 3-specialties Co., Ltd., Inc.). Dose is 0
．． 0.2.0.4.0.6.0, 8.1.0.1.2.
1.6, ■.

8.2, 0.3, 0.4.0 and 5.0 μg/termite. This process was repeated three times. Its dosage (μ
g/termite) was converted to pg/g using the colony's average worker biomass of 5.33±1.51 mg.

The treated termites were transferred to a Petri dish (5.0 cm diameter x 1.5 cm height) containing two filter discs (Whatman No, l) moistened with deionized water.

Three warrior ants were added to each unit to approximate the proportion of warrior ants in the colony.

The experimental units were stored in an environmental chamber at 29±1'o.

Dead and dying workers were recorded and removed from each unit daily for 12 days. The number of deaths at 14 days was used for evaluation as local L D s o by probit analysis.

The effective lethal time (the time required to kill 90% of termites with a certain amount of ELTsoX) was used to measure the time to death.

The local LD of p-tolyl-short methyl sulfone against P. formosanus is 110.4 ~
141.7μ with 95% confidence limit of 168.3μg/g
It was evaluated as g/g. Its inverse equation is Y4.1641+o
, o O60x (±0.0007 slope SE).

When administered topically, the efficacy of p-tolyl-short methyl sulfone was fully exerted 14 days after inoculation. At that time, 1.8μg/termite or more (approximately 337.7μg/g)
Only the group given 90% or higher mortality. As shown in Figure 1, ELT, o is 8.4-
18.9 EI, which indicates that p-tolyl-short methyl sulfone is slow-acting against Formosan termites.

Example 7 Study of slow-acting anti-dietary poison bait (Reticlitermes virginicus): An experiment using poison bait was conducted in order to identify it as a slow-acting substance and to determine the concentration that exhibits minimal anti-dietary properties. Using dyed α-cellulose as a substrate, a chemical substance that showed no activity in soil was tested.

Calco Oil Blue
e DyeXo, 25% by weight) was used for staining to quantitatively compare the treated diets with those of the control. A 30 ml container (cup) with a small hole in the bottom was used as the test device. This was filled with a 1 cm layer of rubstone/gypsum mixture to wick water from a layer of damp cotton placed below the cup. Approximately 0.1 g of treated cellulose was placed in each cup, and 25 worker termites (Reticulitermes) were placed in each cup.
Bilginix) was added. All cups were kept in a larger container with a lid.

43 - control and treatment concentrations 12.5-5. Three replicates were prepared for use in varying the OOO ppm range. The test units were tested for two weeks and termite behavior and physical reactions were observed daily. Dead termites were removed from each test system to minimize fungal and bacterial contamination.

All termites were killed two weeks after exposure to 5.000 ppm of the compound of Example 1. Furthermore, at 100 to 1,500 ppm of the compound of Example 1, the termite survival rate was significantly reduced by treatment.

Example 8 Test for intestinal protozoa of the termite (Reticulitermes virginicus): p-tolyl-
Low concentrations of short methyl sulfone (25, 50, 75,
and lOOppm). One chamber contained 1,000 termites (Reticlitermes bilginicus) collected from untreated wood chips and wild colonies.

The second chamber contains a fungus (Gloephylum traveler-44).
= pre-decay treated with p-1-lilujode methyl sulfone and vacuum impregnated with an acetone solution (ASTM).
(in the manner specified in DI 413-61).

After two weeks of testing, the rear corners of the termites were removed and examined for intestinal protozoa.

Compared to controls, the number of protozoa in the termite hindgut was p-
When treated with 1100 pp of tolyl-short methyl sulfone for 2 weeks, it decreased by about 80%. The survival rate of these termites was only slightly less than the control group after 2 weeks.

However, if additional time elapsed, survival rates were expected to decrease significantly. This is because termites cannot survive without symbiotic protozoa that digest cellulose.

One species of intestinal protozoa, Belsonympha species, was completely destroyed after two weeks. Termites require all four species of protozoa present in their back corners to survive, so their destruction hastens death.

Example 9 German cockroach [Blatella germanii (Linaus)]
] Test for: The test was conducted using a circular glass container stored in a dark room. The compound of Example 1 was added to a 20% protein diet j: 40,00
Mixed at a concentration of 0 ppm. Fifty cockroaches (Blatella germanii) were fed this diet and another 50 control cockroaches were fed an untreated protein diet. 6.13.2
Mortality was counted at 0.27 and 34 days. The total weight of all live cockroaches was divided by the number of cockroaches in each group and the control group to calculate the average weight of the treatment and control groups. The results are shown in Table 4.

On average, the weight of control cockroaches was 7 times greater than that of cockroaches fed p-tolyl-short methyl sulfone during the same period, although not completely paired. The overall mortality rate was also similar.

Table 4 Similar experiments were conducted using 50 second stage nymphs of Blatella germanii for treated and control groups. The results are shown in Tables 5 and 6.

2 mg) 2 mg) 48 In the control group, the eggs molted in 5 weeks, and it was possible to distinguish between males and females, and to count their numbers. Nymphs treated with p-tolyl-short methylsulfone did not reach adulthood.

Example 1O Cockroach (Blatella germanii) behavior and sex test: 10012!2 European cockroaches (40 adults, 60 nymphs) were placed in a completely darkened enclosure (52,5 cm x 42
．． 5cm). A liquid Teflon non-stick coating was coated on the inside to prevent cockroaches from escaping. Two diets were placed in the enclosure, one a control diet and one containing 40.000 ppm of p-1 lyludiiodomethylsulfone.

I took photos with the flash on every 10 minutes for 12 hours.

The distribution of individual cockroaches was recorded and statistically analyzed.

Inside the enclosure, the cockroaches exhibited a normal rhythm of activity. Cockroach dispersal generally increased (aggregated) from the center of the enclosure to the edges, and the two linear regression curves showing dispersibility around treated and untreated baits were similar. There was no statistical difference in the average number of cockroaches at 5 and 10 cm from the control and treated baits. There was also no statistical difference between the average number of cockroaches fed the two diets.

Thus, at a concentration of 40,000 ppm, p-tolyl-short methyl sulfone did not repel or attack Graftella germanica.

The above merely shows examples of the present invention, and the present invention is not limited thereto. Various other embodiments that will be apparent to those skilled in the art are also within the scope of the invention.

[Brief explanation of the drawing]

FIG. 1 is a graph showing the relationship between drug dosage (μg/g) and effective lethal time (ELT, .) in a local toxicity test against termites.

Claims (1)

[Claims] 1. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents R^1(CH_2)n, and n is 0 to 4
and R^1 is lower alkyl, phenyl, mono-lower alkylphenyl, monohalophenyl, nitrophenyl,
Aminophenyl, acetamide-substituted phenyl, (CH_2
)mCOOH-substituted phenyl (m is 1 to 3), dihalo-substituted phenyl, (halo)(nitro)phenyl, (nitro)
(lower alkyl) phenyl, (halo) (lower alkyl)
phenyl or di-lower alkyl-substituted phenyl] An insecticidal composition comprising a compound represented by the following as an active ingredient. 2. The composition according to claim 1, wherein n is 0 and R^1 is p-tolyl. 3. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents R^1(CH_2)n, and n is 0 to 4
and R^1 is lower alkyl, phenyl, mono-lower alkylphenyl, monohalophenyl, nitrophenyl,
Aminophenyl, acetamide-substituted phenyl, (CH_2
)mCOOH-substituted phenyl (m is 1 to 3), dihalo-substituted phenyl, (halo)(nitro)phenyl, (nitro)
(lower alkyl) phenyl, (halo) (lower alkyl)
phenyl or di-lower alkyl substituted phenyl] about 25 ppm to about 4,000 ppm
1. A method for killing termites, which comprises treating with an insecticidal composition containing an insecticidal composition. 4. The method of claim 3, wherein n is 0 and R^1 is p-tolyl. 5. The method of claim 3 or 4, wherein the termite is the Formosan subterranean termite, and the composition contains about 200 ppm to about 4,000 ppm of the compound. 6. The method according to claim 3 or 4, wherein the termite belongs to the genus Reticlitermes and the composition contains about 25 ppm to about 80 ppm of the compound. 7. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents R^1(CH_2)n, and n is 0 to 4
and R^1 is lower alkyl, phenyl, mono-lower alkylphenyl, monohalophenyl, nitrophenyl,
Aminophenyl, acetamide-substituted phenyl, (CH_2
)mCOOH-substituted phenyl (m is 1 to 3), dihalo-substituted phenyl, (halo)(nitro)phenyl, (nitro)
(lower alkyl) phenyl, (halo) (lower alkyl)
phenyl or di-lower alkyl substituted phenyl] from about 10,000 ppm to about 80.0 ppm
1. A method for killing cockroaches, comprising treating with an insecticidal composition containing 00 ppm. 8. The method of claim 7, wherein n is 0 and R^1 is p-tolyl. 9. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents R^1(CH_2)n, and n is 0 to 4
and R^1 is lower alkyl, phenyl, mono-lower alkylphenyl, monohalophenyl, nitrophenyl,
Aminophenyl, acetamide-substituted phenyl, (CH_2
)mCOOH-substituted phenyl (m is 1 to 3), dihalo-substituted phenyl, (halo)(nitro)phenyl, (nitro)
(lower alkyl) phenyl, (halo) (lower alkyl)
phenyl or di-lower alkyl substituted phenyl] from about 10,000 ppm to about 40.0 ppm
A method for killing ants, characterized by treating with an insecticidal composition containing 00 ppm. 10. The method of claim 9, wherein n is 0 and R^1 is p-tolyl.