DE2157051A1 - Novel benzimidazole compound, process for making and using the same - Google Patents

Description

PATENT LAWYERS

dr. W. Schalk dj.pl.-ing. P. Wirth dipl.-ing. G, Dannenberg dr-V-Schmied-Kowarzik · dr. P. Weinhold · dr. D. Gudel

6 FRANKFÜRT AM MAIN

CR. ESCHENHEIMER STRASSE 39

Wd / Be

PISOWS LIMITED

Harvest House,

Felixstowe ,, Suffolk ,, England

Feue benzimidazole compound, process for its preparation and use of the same.

The present invention "relates to a new benziraidazole, acaricide compositions containing the same and to a method for controlling acarids using the same.

It has been found that a particular benzimidazole, when compared to compounds of very similar structure, has an unexpected effect has high acaricidal activity and is reliable with respect to a larger number of crops grown.

The invention also relates to the use of 4,6-di3'od-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole and a method for its production.

Another object of the invention is the use of 4,6-diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole for Combating acarids in a location that is or could be infested with acarids, i.e. a process that the Applying an Akarid-kärapfenden amount of the compound

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the "relevant location as well as an acaricide composition, in which the benzimidazole compound is contained as an effective ingredient.

Me compound can be prepared by reacting 4,6-di; iodo-2-trifluorroethylbenzimidazole with isopropyl chloroformate in the presence of an acid acceptor, for example triethylamine or triethylamine. A salt, for example an alkali metal salt, expediently the sodium salt of ^, e-diiodo ^ -trifluoromethylbenzimidazole, can also be reacted with the chloroformate to produce the desired compound. A temperature from ambient temperature to about 80 ^° C. and an organic solvent, preferably acetone, can be used in each pail.

The compound is generally used in the form of an acaricidal composition which is 4,6-di; iodo-1-isopropoxy carbonyl-2-trifluoromethylbenzimidazole together with a surfactant and / or a carrier. Such compositions usually contain about 10 to 80% by weight 4,6-diiodo-isopropoxycarbonyl-2-trifluoromethylbenzimidazole and about 20 to 90 percent by weight of surfactant and / or carrier. The term "surfactant" is used in its broadest sense and includes materials which variously contain emulsifiers, Dispersing agents and wetting agents can be mentioned. Such agents are for use in acaricide compositions known.

• The carrier can be liquid. For example, the compound may be in a water-insoluble organic solvent such as a hydrocarbon (especially one whose boiling point is in the range of about 130-27O ⁰ C to be dissolved, the appropriate containing a dissolved emulsifying agents so that the solution at the Adding to water represents a self-emulsifiable oil.

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The carrier can also be a solid, for example, clays, sands, Talc, mica, solid fertilizers or a lignosulfonate (e.g. sodium, potassium, calcium or ammonium lignosulfonate). 4,6-Diood-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole can be mixed with a wetting agent with or without a solid support and form a "wettable powder" that is soluble or dispersible in water, or may be with a solid carrier mixed to form a dust, powder or granulated product.

The surfactants used can be anionic compounds such as soaps, sulfate esters, such as dodecyl sodium sulfate, fatty aromatic sulfonates such as alkylbenzene sulfonates or butylnaphthalene sulfonates, more complex fatty sulfonates, such as e.g. the amide condensation product of oleic acid and N-methyltaurine or the sodium sulfonate of dioctyl succinate.

However, the surface-active agents can also be nonionic agents, such as condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide, or fatty esters of sugar or polyhydric alcohols, or those of the latter products obtained by condensation with ethylene oxide, or products as block copolymers of ethylene oxide and propylene oxide are known »The surface-active agents can also be cationic agents such as be.

4,6-Diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenziraidazole can also be used with other pesticides, such as herbicides, insecticides, fungicides, molluscicides or others Acaricides are mixed.

The inventive compositions can by simply Mixing the ingredients are formed.

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The 4,6-di; iodine-l-isopropoxycarbonyl-2-trifluoromethylbenzimidazole can be used to control mites on plants or to control other acarids in or on stored products of plant origin, such as, for example, grain, or to control ticks on animals. This is why it is used “in stored products, in animals, land, soil or plants. Tea and beans can be used. Acaricidal activity is obtained against both adult pests and eggs and is for example against species of mites such as the greenhouse spider mite, Tetranychus telarius ; Fruit tree leaf spider mite , Metatetranychus ulroi; Strawberry mite, Tarsonemus pallidus ; Hop spider mite , Tetranychus urticae; Pear leaf bladder mite, Phytoptus piri ; Gooseberry spider mite , Bryobia praetiosa; Citrus spider mite, Panonychus citri ; oriental mite, Panonychus orientalis ; and such species of ticks as the sheep tick, Boophilus microplus and the African ear tick, Rhipicephalus appendiculatus , are effective.

4,6-Diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole is used on land, soil or crops expediently made in an amount of about 0.6 to 5.6 kg per hectare. When used to control parasitic ticks on animals the compound is conveniently made by immersing the animal in a solution or suspension, e.g. TPM 4,6-diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole contains, applied.

The present invention is explained in more detail by the following examples:

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example 1

A solution of 4,6-di; iodo-2-trifluoromethyrbenzimidazole (146 parts) in methanol (800 parts) was treated with a solution of sodium methylate (67 parts equals 7.7 parts of sodium) and the solvent evaporates, leaving the brown sodium salt was obtained. This was dissolved in dry acetone (1600 parts) and isopropyl chloroformate (41 parts) was added dropwise admitted. The mixture was then heated to reflux for five minutes, allowed to cool and filtered through celite to remove to remove formed sodium chloride.

The filtrate was then evaporated to dryness and a brown one Solid obtained as a residue. This was recrystallized from isopropyl alcohol and 103 parts of 4,6-diiodo-1-isopropoxy carbonyl-2-trifluoromethylbenzimidazole ($ 59 yield). Mp 136-138 ° C.

Analysis: found 0.27.35; H, 1.50; N, 5.15 calculated
C ₁₂ H ₉ F ₃ I ₂ N ₂ O ₂ c, 27.50; H, 1.73; N, 5.35

Example 2

Aqueous acetone solutions containing 1000, 300, 100 or 10 ppm of 4,6-diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole were mixed with 500 ppm of a surface-active agent (condensation product of nonylphenol with ethylene oxide) on young bean plants, Phaseolus vulgaris , applied, each infected with 50 adult leaf spider mites, Tetranychus telarius. The treated plants and mites were ^{kept at 25 °} C. for a period of 48 hours, all mites being killed.

Example 3

Aqueous acetone solutions of 1000, 300, 100 or 30 parts per million of 4,6-di ^ od-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole were used together with 500 ppm of a surface-active agent (condensate

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tion product of nonylphenol with ethylene oxide) on leaf disks that were cut from leaves of young bean plants, Phaseölus vulgaris , and each was provided with 50 to 100 eggs of the leaf spider mite , Tetranychug telarjus. The treated leaf disks and mite eggs were kept on moist filter paper at 25 ° C. for a period of 5 days. After that, all mite eggs were found dead.

Example 4

A mixture of 4,6-diiodo-2-trifluoromethylbenzimidazole (2500 parts) and anhydrous sodium carbonate (722 parts) in acetone (5500 parts) was refluxed. The heating was then discontinued and isopropyl chloroformate (748 parts) was gradually added at a rate such that reflux was maintained. The addition was complete after 30 minutes. The mixture was refluxed for an additional 15 minutes and then poured into cold water (2500 parts). The precipitated product was filtered, well / ater V washed with and dried at 50 ⁰ C, wherein 2932 parts of 4,6-Di3od-l-isopropoxycarbonyl-2-trifluoromethylbenzimidazole (98.2 $ yield). Melting point 137-138 ⁰ C.

The total yield for four identical runs was 11,643 parts which corresponds to an average yield of $ 97.4.

Example 5

A wettable powder was made from the following ingredients:

4,6-Diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole Natriura-oleyl-N-methyltauride.

Calcium Lignosulfonate $ 59

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Example 6

An emulsifiable oil was made from the following ingredients manufactured:

4, 6-I) i, iod-1-isopropoxycar "bonyl-2-

trifluorraethyrbenziaidazole 20 wt. fo

Calcium dodecyrbenzenesulfonate 2.2 wt. $

Condensation product from castor oil with 40 mol

Ethylene oxide 2.75 wt.

Heavy aromatic petroleum (b.p. 210-270 ⁰ C) to 100

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Claims (9)

Claims 1. 4 »6-I) i; joä-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole. / 2J Process for the production of 4j6-dirjod-1-isopropoxycarbonvl · 2-trifluoromethylbenzitnidazole, characterized in that 4,6-Diiodo-2-trifluoromethyrbenzimidazole with isopropyl chloroformate is reacted in the presence of an acid acceptor. 3. The method according to claim 2, characterized in that used as acid acceptor trimethylarain or triethylamine will. 4. A process for the preparation of 4,6-diiodo-1-isopropoxycarbonyl-2-trifluorotethylbenzimidazole, characterized in that a salt of 4,6-di; iodo-2-trifluoromethyrbenziraidazole with Isopropyl chloroformate is implemented. 5. Use of 4,6-I) i: iodine-l-isopropoxycarbonyl-2-trifluorinethyrbenzitnidazole for the control of acarids in places which are "attacked" or which can be attacked by them. 6. Embodiment according to claim 5, characterized in that "when treating animals by immersing them in a solution or suspension of benzimidazole, preferably about 100 to 2000 ppm by weight of benzimidazole contains, takes place. 7. Ausführungsfortn according to claim 5, characterized in that that the benzimidazole on land, soil or crops, preferably in an amount of about 0.6 to 5.6 kg per hectare. 2 0 9 8 2 3/1 1 6 2 8. Ausführungsforra according to claim 7, characterized in that that the benzimidazole on apples ·} pear, peach, apricot or citrus fruit trees; Grapevines; Tea or which bean plants is applied, 9. acaricidal composition, characterized in that it is 4,6-diiodo-1-isopropoxycarbonyl-2-trifluoromethylbenzimidazole together with at least one material selected from the group consisting of pesticides, surfactants and Includes carrier. 20982 3/1162