IL30933A - Pesticidal preparations containing benzimidazole compounds and new benzimidazole compounds - Google Patents

Description

The present invention provides pesticidal preparations as active at least one compound of the general I 0 wherein and are the same or different and are each or is lower alkyl or cycloalkyl X is 0 S or and is phenylalkyl or phenyl optionally substituted by one or more lower alkyl or The pesticidal preparation according to the invention may contain one or more of the following a a an dispersing a an adhesive as well as other known The active substances defined by formula I possess various interesting biocidal They not only act herbicides and but at lower at which no phytotoxic side effects they show a strong lethal action on various representatives of the order acarina mite3 and the insects and soil their eggs and storage for snails and their and bacteria and and worms and The symbol in the general formula I does not include perhalogenated aliphatic residues such as l or Where is a cycloalkyl residue it may Examples of active compounds to be used in the compositions according to the invention are compounds of formula which have an especially good herbicidal In this formula and have the same meaning as with and preferably representing lower or and representing lower alkyl or represents hydrogen or lower alkyl and represents lower alkyl or optionally substituted by alkyl or as exemplified in the following The for of formula are especially distinguished by their fungicidal and ovicidal In this formula and hive the same meaning as in formula with and preferably the meanings given for formula and wherein represents a lower lower alkylphenyl or benzyl as in the following table The active substances of formula I represent benzimidazolylurethanes and Some of them are those of the formula wherein and are independently of each other lower alkyl 1 4 02 or is lower alkyl 1 4 or cycloalkyl 3 6 is lower alkyl 1 phenyl that is unsubstituted or substituted 1 to 3 times by lower alkyl 1 4 or X is sulfur the or alkyl 1 4 0 except that when is methyl and X is cannot One group of compounds of formula are those of the formula wherein the significance given represents hydrogen or lower alkyl and represents lower alkylphenyl or except that when is methyl and is cannot be Another group of compounds of formula are those of the formula wherein and have the significance given and represents a lower lower alk lphenyl or benzyl The new compounds of formula may be manufactured by reacting a benzimidazolyl derivative of formula with a compound of formula B V are wherein A and which are able to form the grouping X II 0 whilst undergoing elimination or the procedure followed will he to in optional a reactive derivative of carbonic acid or acid with imidazole of formula IV and an of formula V an alcohol i i or phe o1 the procedure followed for the formation of the ureas will be to react an imidazole of formula IV with an isocyanate or a carbamic acid whilst in manufacture of urethanes an imidazole of formula IV is reacted with the desired chlorocarbonate The new preparations can be applied in many different for in the form of dusting powders and They can also be worked directly into the j optionally together with Possible materials the manufacture of directly solutions of the compounds of general formula I for j mineral oil fractions of high to medium boiling j for oil coal tar oil and oils of vegetable or animal as well as for 1 alkylated using and furthermore chlorinated for tric ethane and trichlorethylene or benzenes and tetrachlorobenzenes It is advantageous to use i organic solvents having boiling points above j It is especially appropriate to prepare aqueous forms application from emulsion pastes or wettable spraying powders by adding Possible emulsifiers o dispersing agents are products for j sation products of aliphatic amines or carboxylic 13 a Some known benzimidazole compounds have a carbonyl substituent in the similarly as have the compounds of formula I have been exhaustively investigated from the point of view of their chemistry or their possible pharmacological see the articles referred to in CA 8365 The French Patent 1379 540 discloses acid as polymerisation activator for the US Patent describes among other materials acid as sizing agent for paper and Finally benzimidazoles having in a perhalogenated substituent and in either hydrogen or a carbonyl or thiocarbonyl ester are disclosed as herbicidal agents in the French Patent 1 459 782 or the Dutch Patent Applications 66 and 66 The invention is illustrated by the following Examples to which it is not A mixture of g 210 of g of 0 and 70 ml of water is added into a sulfonation The flask is then externally cooled and to the stirred content is at a temperature range of 10 g of Methylthioformate The reaction is slightl When all the methylthioformate is stirring is for 1 The organic layer is then separated from the reaction mixture and dried over Then the solvent distilled off and a oil remains which becomes to Analysis N compound 15 The compounds were also analogous mann point 3 17 Example 2 A etting is manufactured from in the following 20 g of active substance are very finely ground in a pin mill together with 8 g of fine precipitated silicon available under the name as s with 6 g of Bolus g of a condensation product of 1 of octylphenol with about 8 of ethylene oxide and g of sodium thus obtained can be worked up water in any desired to give stable Example 3 was applied in the process to the test plants below using an amount 2 kg of active The application took place 12 days after sowing the test when had developed 1 to 2 Digitaria Beta Chrysanthemum 9 Brassica 9 Amaranthus Soya 2 Cotton 2 V 1 plant plant no longer viable 9 plant Example 4 The urethanes listed in Example showed a good action against weeds in the and in the The following results were achieved fo compounds 23 25 and 1 no damage plant no longer viable 9 plant completely Example 5 Compound was tested for its action mildew Courgette plants Pepo were grown in a green house and sprayed once prophylactically with an aqueous broth of the compound containing increasing quantities of active Two days after the the plants were infected with spores of cichoracearum and after days the plants ere rated as regards fungal a lower inhibitory concentration of 30 ppm of 19 insufficientOCRQuality

Claims (15)

1. Pesticidal preparations containing as an active ingredient a "benzimidazole compound of the general formula wherein ^, 2 and R^ are the same or different and are each hydrogen, halogen, alkyl, -NC^ or CF^, R^ is hydrogen lower alkyl "or cycloalkyl, X is 0, S, -WH- or N-alkyl and Rc is alkyl phehylalkyl or phenyl optionally substituted by one or more halogen, nitro, lower alkyl or CP^ groups.

2. Preparations as claimed in Claim 1, wherein there is present one or more of the following additives: a solvent, a diluent, an emulsifier, a dispersing agent, a thickener, an adhesive as well as other known pesticides.

3. ~ preparations as claimed in Claim 1 or 2, especially a herbicidal preparation, wherein the active component is a compound of formula wherein ^, 2 and ^ have the significance given in Claim 1, Rg represents hydrogen or lower alkyl and R^ represents lower alkyl, phenyl, alk lphenyl or trifluoromethylphenyl. ;> - 20 - 30933/2

4. Preparations as aclaimed in Claim 1 or 2, especially herbicidal, fungicidal or ovicidal preparations, wherein' the active component is a compound of formula wherein R^, R2 and ^ have the significance given in Claim 1, and Rg represents a lower alkyl, phenyl, halophenyl, nitro-phenyl, lower alkylphenyl or benzyl residue.

5. Preparations aa claimed in any one of Claims 1, 2 or 4 especially ovicidal preparations wherein the active component is a compound of formula wherein ^ and R^ have the significance given in Claim 1.

6. Preparations as claimed in any one of Claims 1, 2 or 4» especially herbicidal and fungicidal preparations, wherein the active component is a. compound of formula wherein RQ. represents a lower alkyl, phenyl, halophenyl, nitrophenyl, lower alkylphenyl or benzyl residue. 21 - 30935/2

7. reparations as claimed in any one of Claims 1, 2 or 4, especially herbicidal and fungicidal preparations wherein the active component is a compound of formula wherein and Eg have the significance given in Claim 1.

8. A preparation as claimed in any one of Claims 1, 2 or 4, especially a herbicidal preparation, wherein the active component is the compound of formula

9. A preparation as' claimed in any one of Claims 1, 2 or 4, especially a herbicidal preparation, wherein the active component is the compound of formula

10. , Pesticidal preparations as claimed in Claim 1 and substantially as described in any one of Examples 2 - 5 herein.

11. A method of treating living plants to combat pests, formula I in Claim 1 alone or in the form of a preparation, as claimed in Claim 1.

12. , Benzimidazole compounds of the general formula wherein and R'2 are independently of each other hydrogen, lower alkyl 1- 4 0, CF^, N02 or chlorine, '^ is lower alkyl 1 - 4 C, or cycloalkyl 3- 6 C, R1,. is lower alkyl 1 - 4 C, phenyl that is unsubstituted or substituted 1 to 3 times by halogen, nitro, lower alkyl 1-- 4 0 or OP^, X is oxygen, sulfur the -NH- or -N-lower alkyl 1 - 4 C group, except that when '^ is methyl and X is -NH, R'^ cannot be phenyl.

13. · Benzimidazole compounds according to Claim 12 of the general formula wherein R'^, R'2 and R'^ have the significance given in Claim 12, 'g represents hydrogen or lower alkyl and R* represents lower alkyl, phenyl,, alkylphenyl or trifluoro-methylphenyl, except that when R'^ is methyl and R'g is hydrogen, R'y cannot be phenyl.

14. Benzimidazole compounds according to Claim 12 of the general formula wherein R^, R'2 and R'^ have the significance given in Claim ¾ and R'g represents a lower alkyl, phenyl, halophenyl, nitro-phenyl,- lower alkylphenyl or benzyl residue.

15. Benzimidazole compounds according to Claim 12 sub-, stantially as described in Example 1 herein. PC/rb