DD141900A5 - INSECTICIDES MEDIUM - Google Patents

Abstract

The invention relates to an insecticidal agent with a Thiadiazolylbenzamid as an active ingredient. The new product is intended to provide a high-potency drug as a broad-spectrum insecticide. Examples of the active compounds according to the invention are N- [5- (2-indenyl) -1,3,4-thiadiazol-2-yl] -2,6-dimethoxybenzamide, N- [5- (5-methoxy-2- benzo [Ыfuryl] -1,3,4-thiadiazol-2-yl] -2,6-dimethoxybenzamide, N- [5- (5-trifluoromethyl-2-benzolb] furyl) -1,3,4-thiadiazole-2-one yl] -2,6dimethoxybenzamid.

Description

210 71

Title of the invention :

Insecticides

Application of the invention ·:

The invention relates to an insect extracting agent of about 10 to 95% of an inert carrier and about 5 to 9.0% of a Thiadiazolylbenzamids as active ingredient.

Characteristic of the known technical solutions ;

Insect control is one of the first tasks undertaken by chemical research in agriculture and requires constant development. Insects of many orders not only attack natural plants of all varieties, but also cause unhygienic conditions and spoilage through contamination of food and feed. The damage caused by insects can no longer be quantified, which is why the control of harmful insects inevitably has the highest priority.

The withdrawal of the old residue insecticides has recently revived the search for new and better insecticides.

Herbicidal 1,3,4-thiadiazol-2-yl ureas are already known from US Pat. No. 3,726,892.

Indian J. Chem. 8, 509-513 (1970) describes a process for the preparation of 2-amino-1,3,4-thiadiazoles, and these compounds are intermediates for the preparation of the present compounds.

US Pat. No. 3,748,356 discloses N-benzoyl-N'-phenylureas which are herbicidal and insecticidally active.

Insecticidally active compounds are already described in DD-PS 130 038, which are reported on Thiadiazolylbenzamide, which may be mono- or disubstituted by hydrogen , chlorine, fluorine, bromine, methyl or methoxy on the'Phenylring and their Thiadiazolring by five- or six-membered aromatic, cyclic or optionally heterocyclic radicals are substituted, which may optionally also be condensed to bicycles.

Zxel of the invention :

However, now that none of the known insecticides has properties that would be fully satisfactory in all respects, the object of the invention is to provide a novel insecticidal agent which does not have certain disadvantages of the known insecticidal agents and is distinguished above all by a high level of insecticidal activity Effectiveness as a broad spectrum insecticide. * '

Explanation of the essence of the invention:

This object is achieved according to the insecticidal agent of the type mentioned in the present invention in that it is a Thiadiazolbenzamid the formula I as the active ingredient

HO

1 "

0CH3

OCH

contains

wherein R represents one of the following radicals:

(D ₇

R- ^v · ' X

or

in which

Oxygen or sulfur means

one of the substituents R ¹ or R ²

Is hydrogen and the other is fluoro, chloro, bromo, trifluoromethyl .or. Methoxy,

one of the substituents

3 4 R or R

Is hydrogen and the other is methoxy or trifluoromethyl,

one of the substituents R ⁵ or R ⁶

one of the substituents R ⁷ or R ⁸

Is hydrogen and the other is chlorine, bromine,

Represents fluorine, trifluoromethyl or hydrogen and

Is hydrogen and the other is C ₁ -C ₃ -alkoxy which is substituted with one or more fluorine atoms.

The new Thiodiazolylbenzamide the above formula I can be prepared by reacting either

(1) a 2-amiho-5-R-substituted-1,3,4-thiadiazole of formula II

ζ wherein R has the meaning given above, with a

Benzoyl halide of the formula III

OGH ₃ ·

Halo-C- <"V.

- ra

orin Halo is chloro or bromo, acylated or

(2) a compound of formula IV

OCH ₃

oi

E-NH-CN ¹ HC-

2

where E. represents R-C-NH- or R-CiI = N- /

wherein R has the meaning given above, either with a dehydrating agent, if E for

IU / IO

Il

R-C-NH-

stands, or with an oxidizing agent, if E for

R-CH = N-.

stands, handles.

All ratios and percentages given below are by weight. The indicated temperatures are in degrees Celsius. By halogen is meant fluorine, chlorine, bromine or iodine.

The present thiadiazolylbenzamides of the formula I are prepared by known or analogous methods. All thiadiazolylbenzamides can easily be obtained by acylation of 2-amino-5-R-substituted-1,3,4-thiadiazoles of the formula II

II

wherein R has the meaning given above, with Benzoy! halides of the formula III °.

CH3

CCH O I

Il HaIo-C

CH3

where halo is chlorine or bromine. ·

The acylation is carried out in the presence of a base in a reaction solvent such as tetrahydrofuran, dimethylformamide, dimethyl sulfoxide or diethyl ether. The preferred base is sodium hydride, but organic bases such as pyridine, triethylamine Q of triethanolamine, and other inorganic bases such as sodium hydroxide, potassium carbonate or lithium bicarbonate may be used, and the temperature range of this reaction is between about -10 and about 75 ^degrees C, preferably between about 0 ⁰ C and about 25 ⁰ C.

The aminothiadiazoles required as starting materials are. _% prepared by known methods. In general, they are obtained by oxidative cyclization of a thiosemicarbazone, preferably with ferric chloride, or by dehydrating cyclization of a thiosemicarbazide with a strong acid. In this connection, reference is made to the already mentioned Indian J. Chem. 8, 509-513 (1970) and. referenced U.S. Patent 3,725,892. ,

The thiadiazolylbenzamides of the formula I in which R has the meaning already mentioned may also be obtained by cyclizing a compound of the formula IV. .

 - '- · OCHA.

E-NH-C-NH-C- ''y>. IV _}

t> ™ a ·· '"

Jena; ,

    '' o "'"; "'" ".. '' - · · '' '·.' '"

ti *. -

wherein R is R-C-NH- or R-CH = N-,

wherein the substituent R has the abovementioned meaning, with either a dehydrating agent, if E-.for '

stands, or with an oxidizing agent, if E for

•. 'R-CH = N-. ·. ·

• stands to be produced. ·

Suitable dehydration excipients include phosphoric acid, formic acid, phosphorus pentachloride, phosphorus pentoxide in the presence of a strong acid, and the chlorides and anhydrides of benzoic and alkanoic acids. The preferred dehydrating agents are the strong acids, especially methanesulfonic acid and concentrated sulfuric acid. - ·

The dehydrating cyclization is carried out at temperatures of about -20 to 80 ^° C., preferably at room temperature. Usually, this reaction is preferably carried out without a solvent, but if desired, it may also be carried out with solvents, examples of which are;

'£. IV. / 1

- halogenated benzenes and halogenated alkanes, such as chlorobenzene or methylene dichloride. '·

The preferred oxidizing agent is ferric chloride. However, other strong oxidizing agents can be used, such as calcium ferricyanide. Oxidative cyclizations are preferably carried out in lower alkanols, such as ethanol or propanol, at the reflux temperature of the reaction mixture. In general, temperatures of about 50 to 100 ⁰ C may be applied ', if appropriate. ..

The starting materials required to prepare the thiadiazolylbenzamides of formula I are readily available to one of ordinary skill in the art.

The following examples illustrate the synthesis of typical representatives of the thiadiazolylbenzamides of the present invention, and the reported procedures demonstrate the synthesis of typical starting materials. All of the compounds obtained are identified by nuclear magnetic resonance analysis, parent nuclear analysis and, in some cases, infrared analysis and mass spectroscopy

 Ausfühiungsbeispiele

f The first group of examples illustrates the preparation of thiadiazolylbenzamides of the formula I by acylation of aminothiadiazoles.

example 1

N- / 5- (4-trifluoromethoxyphenyl) -1,3,4-thiadiazol-2-yl ₁ / -2J _: 6-

dimathoxybenzamid

A mixture of 1.8 ml of pyridine and 5.2 g of 2-amino-5- (4-trifluoromathoxyphenyl) -1,3,4-thiadiazole in 50 ml of tetrahydrofuran is heated to reflux temperature. Thereafter, 4.4 g of 2,6-dimethoxybenzene chloride in 20 ml of tetrahydrofuran are added dropwise over a period of 15 minutes.

The mixture is then heated for a further 45 minutes with stirring to reflux temperature. Then the solvent is removed by vacuum and the resulting residue is recrystallized from aqueous ethanol. In this way, 7.2 g of the title compound are obtained in the form of white needle-like crystals which melt at from 201 to 203.degree.

Example 2

N- / 5- (6-methoxy-2-benzo / b / furyl) -1,3,4-thiadiazol-2-y0 / -2,6-

dimethoxybenzamide

100 ml of tetrahydrofuran containing 0.7 g of 2-amino-5- (6-methoxy-2-benzo / b / furyl) -1,3,4-thiadiazole is added with 0.3 g of sodium hydride. After bubbling ceases, 0.62 g of 2,6-dimethoxybenzoyl chloride are added. The reaction mixture is stirred for 1 hour at room temperature, after which the solvent is removed by evaporation under vacuum. The residue is treated with water, after which the acid is acidified with 1- normal hydrochloric acid. The solids are filtered off, dried and recrystallized from benzene-hexane, so as to obtain 0.12 g of the title compound which melts at 215-217 C ^0th

The process described in Examples 1 and '2 is repeated to prepare the further thiadiazolylbenzamides indicated below. The substituents present in the aminothiadiazoles and benzoyl halides required for this purpose are readily obtained from the thiadiazolylbenzamide product obtained in each case. The compounds specifically described hereinafter are referred to hereafter, while in the subsequent listings, the amounts of reactants used and the amounts and melting points of the compounds obtained are summarized.

, , , Example 3

N - / _ 5- (2-indenyl) -1,3,4-thiadiazol-2-yl / -2,6-dimethoxybenzamide

Example 4

N- / 5- (5-methoxy-2-benzo / b / furyl) -1,3,4-thiadiazol-2-yl / -2,6-dimethoxybenzamide. , ,

Example 5

N- / 5- (5-trifluoromethyl-2-benzo / b / furyl) -1,3 _/ 4-thiadiazol-2-yl / 2,6-dirnethoxybenzamide.

example

N- / 5- (6-trifluoromethyl-2-benzo / b / furyl) -1 _/ 3 _/ 4-thiadiazol-2-yl / -2,6-dimauhoxybenzamide

Example 7

N- / 5- (4-pentafluoroethoxyphenyl) -1,3,4-thiadiazol-2-yl. - 2 , S -dimethoxybenzamide ···

B e i s ρ i e 1 8

K- / 5- (5-Pluor-2-benzo / b / furyl) -1,3,4-thiadiazol-2-yl / -2, 6-

dimafhoxybenzaiide. ·, '

list

Example no. Ammothiadiazol Benzoyl chloride product Melting point, C 3 1.0 '· 1.0 0.2 230-232 4th 2.0 1.8 1.3 255 - 257 5 2.8 2.2 2.5 242 - 245 6 2.0 1.6 1.0 206-208 '7. 3.1        · 2.2   1.7 227. -P 229 8th 2.4 2.2 1.7 244 - 245,

β, ι

The next group of methods and examples illustrate typical cylizations using dehydrating agents. ·

Production method 1 .

1- (4-pentafluoroethoxybenzoyl) -4- (2,6-dimethoxybenzoyl) thiosemi-; _; carbazide

Add 0.54 g of ammonium thiocyanate to 10 ml of tetrahydrofuran, C. , The reaction mixture is heated to reflux and then treated with 1.5 g of 2,6-dimethoxybenzoyl chloride, which in. 10 ml of additional tetrahydrofuran is dissolved. The mixture is stirred for 20 minutes at reflux temperature, cooled to ambient temperature and finally treated dropwise with 1.5 ^- 4 g offset Pentafluorethoxybenzoylhydrazin, which is dissolved in 20 ml of tetrahydrofuran. The reaction mixture is then further stirred for 1.5 hours at ambient temperature. The mixture is then evaporated under vacuum to dryness and the resulting residue is washed with diethyl ether. The resulting diethyl ether solution is concentrated under vacuum and the resulting product is recrystallized to give 1.1 g of the title compound, which melts at 184-186 ⁰ C.

Example 9

N- / 5- (4-Pentafluorethoxyphenyl) -1,3,4-thiadiazol-2-yl / -2,6-

dimethoxvbenzamide ·

1 g of the intermediate formed by the above preparation 1 is slowly added to 5 g of methanesulfonic acid and the resulting mixture is then stirred for 5 hours at ambient temperature. Then pour the mixture slowly to 100 g

Ice and stir thoroughly. The pH of the aqueous mixture is then brought to 8.5 by the addition of concentrated ammonium hydroxide, the solids are filtered off and recrystallized from aqueous ethanol. In this way you get to 0.6 g of crude product. The product is purified by chromatography on silica gel using a solvent mixture of 70% toluene and 30% ethyl acetate. This gives 200 mg of pure title compound, which is identical to the product of Example 7.

Example 10 «.

N- / 5- (4 "-triphenyluroxyphenyl) -1,3,4-thiadiazol-2-yl / -2, 6- dimethoxybenzamide -.

Following the procedure described in Example 9, 1- (4-trifluoromethoxybenzoyl) -4- (2,6-dimethoxybenzoyl) thiosemicarbazide is reacted with methanesulfonic acid to give the titled compound which is identical to the compound of Example 1 ,

Example 11

, N- / 5- (6-methoxy-2-benzo / b / furyl) -1, 3,4-thiadiazol-2-yl / -2, 6-

dimethoxvbenzamid

A certain amount of 1 ~ (6-methoxy-2-benzo / b / furylcarbonyl) -4- (2,6-dimethoxybenzoyl) thiosemicarbazone is reacted with methanesulfonic acid by the method described in Example 9 to give the title compound , which is identical to the compound of Example 2.

B e i s ρ i e 1. 12 N- / 5- (2-indenyl) -1,3,4-thiadiazol-2-yl.-2,6-dimethoxybenzamide

1- (2-indenocarbonyl) -4- (2,6-dimethoxybenzoyl) thiosemicarbazide is reacted with methanesulfonic acid by the method described in Example 3 to give the title compound which is identical to the compound of Example 3.

Beispiel " Example 13" *.

N- / 5- {5-methoxy-2-benzo / b / furyl) -1,3,4-thiadiazol-2-yl / 2,6 ~

, dimethoxybenzamide ·

1- (5-Methoxy-2-benzo / b / furylcarbonyl) -4- (2,6-dimethoxybenzoyl) -thiosemicarbazide is reacted with methanesulfonic acid by the method described in Example 9 to give the title compound which is treated with the compound of Example 4 'is identical.

Example 14

N- / 5- (5-trifluoromethyl-2-benzo / b / furyl) -1,3,4-thiadiazol-2-YV

2,6-dimathoxybenzamide

A certain amount of 1- (5-trifluoromethyl-2-benzo / b / furylcarbonyl) -4- (2,6-dimethoxybenzoyl) thiosemicarbazide is reacted with methanesulfonic acid by the method described in Example 9 to give the title compound, which identical to the compound of Example 5.

Example 15 '.'. ''

N- / 5- (6-trifluoromethyl-2-benzo / b / furyl) -1,3,4-thiadiazol-2-yiy-

_ ' ; dimethoxybenzamide . ·

It is T- (6-trifluoromethyl-2-benzo / b / furylcarbonyl) -4- (2 ₇ 6-dimethoxybenzoyl) thiosemicarbazide to the method described in Example 9 with methanesulfonic acid, which leads to the title compound with the compound of Example 6- is identical. ".

Example 16 '

N- / 5- (5-fluoro-2-benzo / b / furyl) -1,3,4-thiadiazol-2 ~ yl / -2,6-

dimethoxybenzamide \ __

1- (5-Fluoro-2-benzo / b / furylcarbonyl) -4- (2,6-dimethoxybenzoyl) -thiosemicarbazide is reacted with methanesulfonic acid by the method described in Example 9 to give the title compound which is reacted with the compound of Example 8 is identical. ,

In order to determine the range of their insecticidal activity, the thiadiazolbenzamides of Forxrel I used according to the invention are extensively tested against live insects. The following investigations are exemplary for the investigations carried out and the results obtained here.

In many cases, several studies with the same application ratio, worked, and the results obtained are then geraittelt. Spaces in the tables below mean that no examination has been carried out at the said application ratio. The compounds used are characterized by their respective example number.

Investigation 1 ' ^: · · ._.

Mexican bean beetles and caterpillars of cotton moth .

Each compound to be tested is formulated by dissolving 10 mg of active ingredient in 1 ml of an anhydrous solvent mixture of one part of ethanol and one part of acetone containing a total of 36 g of a surfactant (23 g Toximul R and 13 g Toximul S) per liter. (In Toximul is "are mixtures of surface-active sulfonates and nonionic. See surfactant Stepan Chemical agents Co. ,, ^ 'Northfield, Illinois, USA). Each sample is then ^v dispersed in 9 ml of water to give a By dilution of this dispersion with water, lower concentrations can be formed if desired.The dispersion is then sprayed evenly over 10-day-old bean plants, after which the plants are set aside to dryness.

Then one takes from the plants leaves whose cut ends are wrapped in water-soaked cotton wool. In each case two leaves are placed in a 100 mm plastic Petri dish, in which then each 5 larvae of the Mexican bean beetle (Epilachna varivestis) of the second or ν ...). third appearance and 5 larvae of cotton wool (Spodoptera eridania) of the second or third appearance. For each compound to be tested, work with 3 Petri dishes each. The Petri dishes are at about 4 days. 25 ⁰ C and 51% relative humidity, followed by the first assessment of insecticidal activity. Some Petri dishes are left for another 3 days under the conditions mentioned and then subjected to a further evaluation.

The insecticidal activity of the investigated compounds is compared with the following evaluation scale

Solvent blind and untreated blank samples evaluated:. , ,

Beurtexlungsskala

O = .no fight. '1 = killing 1-7 larvae

2 = killing of 8-14 larvae

3 = killing of 15 larvae

The results obtained in the above tests are shown in the following Table I.

T a b e 1 1 e

Connection of example Application amount in Mexican bean beetle 7 days Cotton Red Caterpillar 7 days No. ppm. , 4 days 2 4 days 2 2 1Q00 2 2 2 2 100 1 1 1 3 3 , 1000 0 0 3 3 100 0 .0 2 0- 4 1000 0 0 0 0 loo 0 3 0 3 5 1000 0 2 3 3 100 0 2 3 3 6 1000 0 2 ' 3 3 100 0 Third 2 3 7 1000 2 .3 3 3 100 2 Second 3 3 8th ^: 1000 2 1 3 3 100 1 3

The compound of Example 1 is tested by the same procedure as above, but operating with a different amount of application. Instead of "from -

However, the number of killed insect larvae is expressed in the form of percentage

Killing rate. After a 4-day study of cotton moth larvae larvae, this compound gives a 100 percent kill at 5 ppm application level, and a 100 percent kill is also obtained after 7 days trial on an application. amount of only 2.5 ppm. At a corresponding. Untersuchung_ C against Mexican bean beetles results after 4-TAE ^v giger duration of the experiment at a rate of application of. .5 ppm one hundred percent kill while receiving an 80 percent kill for 7 days at a rate of only 2.5 ppm. ". ,

The experimental data presented above demonstrate the good insecticidal activity of the thiadiazolyl banzarnides of formula I. It is readily apparent to entomologists that the present compounds are to a great extent suitable for controlling insects of various orders which are detrimental to humanity and its economic activities , · - ^ '...

With the present. >. Thiadiazolylbenzamides can be used, for example, to combat the following organisms: Coleoptera, such as Anthonomus grandis, Crambus caliginosellus, Oulema · melanopus / Leptinotarsa deceralineata, Hypera postica, Anthrenus scrophulariae, Tribolium confusum, Lyctidae species, Agriotes species, Sitophilus oryzae, Nodonota puncticollis and Conotrachelus neruphar ; Diptera, such as Musca domestica, Stomoxys calcitrans, Haematobia. irritans, phormia regina, hylemya

brassicae and psila rosas; Lepidoptera, like Laspeyresia · · .-- * pornoella,

Euxoa species, Plodia interpunctella, Tartricidae species, Heliothis zea, Ostrinia nubilalis, Hellula rogatalis, Trichoplusia ni, Thyridopteryx ephemeraeformis, Malacosoma americanuni and Spodoptera frugiperda; and Orthoptera, such as Blattella germanica and Periplaneta americaria.

The present compounds are useful for reducing the population of insects. They are therefore also used in methods for reducing an insect population, which consist in applying an insecticidally effective amount of such a compound to a substance which is consumed by the insects. ". '

Insects can be made to take in a particular ingredient by applying the compound to a substance that they consume. For example, insects infesting plants can be readily combated by applying a compound to plant parts which the insects eat, especially to the foliage. Insects that infest or consume textiles, paper or wood products, can be easily combated by treating such products with the respective active ingredients. In the same way, such agents can also be used to protect stored grain or seeds.

The present compounds interfere with the formation of subsequent forms of insects that ingest these compounds. If, for example, adult insects absorb these active ingredients, they will generally not suffer any impairment, but will lay sterile eggs. If an insect larvae takes on such a compound, it dies without metamorphosis to the next larval form. Larvae of the last appearance, which take up such an active ingredient, pupate, but die off in the pupal form.

It is readily apparent to entomologists that the use of a compound of formula I does not necessarily result in the destruction of an entire insect population. In some cases, of course, the entire population is destroyed. "In other cases, however, only a portion of the insects are killed while others survive the treatment with the respective active ingredient.The part of the population killed depends on the insect species, the compound used , the application amount, the resistance force of the insects, the weather and other well known factors. sub. reducing an insect population is ζ therefore understood to mean any decrease in the number of living insects, which amounts in some cases also to the disappearance of the entire population of the insects treated.

The extent of population reduction caused by a particular compound is of course dependent on the amount of application of the particular compound. However, it must always be worked with an at least insecticidally / effective amount. This is understood to mean an amount of active ingredient which can be used to achieve a measurable reduction in the treated insect population. Insecticide effective. Amounts are generally in the range of about 1 to 1000 ppm. · '· · · -.

; , The amount of use of insecticidal agents usually represents the concentration of the insecticidal agent in the dispersion in which it is applied. The amount of application is therefore determined because this is most conveniently a sufficient amount of dispersion for covering the foliage or other substances to be treated with a thin film thereof. The applied amount of the dispersion thus depends on the surface of the edible substance to be treated, and the amount of the compound depends on its concentration in the dispersion.

The dispersions to which the present compounds are applied are prepared from conventional insecticidal preparations which are novel by the presence of the compounds of the present invention. Widely useful are aqueous dispersions which can be prepared by mixing with a small amount of a concentrated insecticide agent with an appropriate amount of water to give the desired concentration of the particular compound. Such concentrated water-dispersible compositions, which generally contain about 5 to 90% active ingredient, can be used in the form of emulsifiable concentrates, wettable powders or suspensions. · .... ·· ". '

Wettable powders are intimate mixtures of the respective active ingredient with an inert carrier which constitutes a mixture of a fine inert powder and surface-active agents. The drug concentration is usually 10 to 90% by weight. As inert powders usually attapulgite clay, montmorillonite, diatomaceous earth or purified silicates are used. Useful surfactants that make up about 0.5 to 10% of the wettable powder include the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and the nonionic surfactants such as ethylene oxide adducts of alkylphenol.

Exemplary emulsifiable concentrates of the present compounds may contain from about 50 to 500 g of active ingredient per 1 of liquid, corresponding to an amount of about 5 to 50%, dissolved in an inert carrier which is a mixture of a water-immiscible organic solvent and emulsifying agents. Suitable organic solvents for this purpose are, for example, the aromatics, in particular the xylenes, and the petroleum fractions, in particular the high-boiling naphthalene and olefin fractions of petroleum, such as high-boiling aromatic naphtha. Also other organic solvents

, - ·. can be used, for example terpene solution with the inclusion of natural resin derivatives and complex alcohols, such as 2-ethoxyethanol. Emulsifiers suitable for emulsifiable concentrates belong to the same group of substances and are used in "equal concentrations as the surface-active agents described above for the wettable powders.

Suspensions of the present compounds contain an amount of active ingredient similar to the concentration in an emulsifiable concentrate, for example a finely divided powder, in suspension in a suitable non-solvent liquid. Best suited for this purpose as non-. dissolving liquid a mixture of water and. surfactants. To prepare the suspensions, the same surfactants are used as are used to form wettable powders. Occasionally, a small amount of an inert diluent is also used to improve the suspending properties. Such inert diluents include attapulgite clays, montmorillonite, starches, and in particular, purified silicates. ,

  If desired, the active ingredient may also be used in the form of a solution in an organic solvent, usually a mild petroleum oil, such as a spray oil widely used in agrochemistry.

The present compounds may also be used in the form of dusts and aerosol formulations. - Dusts contain the respective compound in fine powder. Verified form, which is dispersed in a powdery inert carrier. The carrier is usually pulverized clay, such as pyrophyllite, bentonite, volcanic deposit or montmorillonite. Dusts normally contain the active substance in concentrations of about 0.1 to 10%.

Aerosol formulations contain or dissolve a compound of Formal I in an inert carrier consisting of a pressurizing propellant mixture and are packaged in a container from which the mixture is discharged through a ultrafine distribution valve. Propellant mixtures contain either low-boiling halogenated hydrocarbons in admixture with organic Solvents or aqueous suspensions which are pressurized with inert gases or gaseous hydrocarbons. ,

Claims (9)

ι y? invention claims 1. Insecticidal agent of about 10 to 95% of an inert carrier and about 5 to 90% of a Thiadiazolylbenzamids as active ingredient, characterized in that it as the active ingredient thiadiazolylbenzamide of the formula I. J ·. H O 1 Il R-- ". OCH ₃ A » _v (D; CHa contains wherein R represents one of the following radicals :. ι , Κ / \ A Θ O-O S or -of. o-R ' in which Oxygen or sulfur means one of the substituents R ¹ or R ² Is hydrogen and the other is fluoro, chloro, bromo, trifluoromethyl or methoxy, one of the substituents R ³ or R ⁴ Is hydrogen and the other is methoxy or trifluoromethyl, one of the substituents R ⁵ or R ⁶ Is hydrogen and the other is chlorine, bromine, fluorine, trifluoromethyl or hydrogen and one of the substituents R ⁷ or R ⁸ Is hydrogen and the other C.sub.1 -C.sub.12 alkoxy substituted with one or more fluorine atoms. 2. Insecticidal product according to item 1, characterized in that it contains as active ingredient N- / 5- (5-trifluoromethyl-2-benzo / b / furyl) -1,3,4-thiadiazol-2-y: L / Contains -2,6-dimethoxybenzamide. 3. Insecticidal composition according to item 1, characterized in that it contains as active ingredient N- / 5- (6-trifluoromethyl-2-benzo / b / furyl) -1,3,4-thiadiazol-2-yl / -2,6 -dimethoxy benzamide. 4. Insecticidal composition according to item 1, characterized in that it contains as active ingredient N- / 5- (5-fluoro-2-benzo / b / fury]) - 1, 3, 4-thiadiazol-2-y_l / -2, Contains 6-dimethoxybenzamide. 5. Insecticidal composition according to item!, Characterized in that it contains as active ingredient N- / 5- (4-Tr: ifluor- ⁱ methoxyphenyl) -1, 3,4-thiadiazol-2-yiy-2,6-dimethoxybenzamide. 6. Insecticidal composition according to item 1, characterized in that it contains as active ingredient N- / 5- (4-pentafluoroethoxyphenyl) -1,3,4-thiadiazol-2-yl / -2, 6-dimethoxybenzamid ^. An insecticidal composition according to any one of items 1 to 6, characterized in that it is in the form of a wettable powder and from about 10 to 90% of a thiadiazolylbenzamide as active ingredient, about 0.5 to 10% of a surfactant and about 0 to 89 , 5% of an inert powder. An insecticidal composition according to any one of items 1 to 6, characterized in that it is in the form of an emulsifiable concentrate and from about 5 to 50% of a thiadiazolylbenzamide as the active ingredient, about 0.5 to 10% of a surfactant and about 40 to 94.5% of an organic solvent. 9. An insecticidal composition according to one of the items 1 to 6, characterized in that it is in the form of a suspension and from about 5 to 50% of a Thiadiazoiylbensaraids as active ingredient, about 0.5 to 10% of a surface-active agent and about 40 to 94 , 5% of a non-solvent liquid.