DE1121880B - Insect repellants - Google Patents

Description

The compounds known as "cyclodienes" and produced according to the principle of diene synthesis are obtained an ever increasing importance in the control of insects which are harmful to plants. Of the The focus of action of these preparations is on pests with biting M and tools, such as Beetles and their larvae, as well as caterpillars.

This group of "cyclodienes" includes several effective products that can be produced by the addition of halogenating cyclopentadienes on unsaturated cyclic ethers and acetals are represented (cf. z. B. German Patent 960 284; German Auslegeschriften 1006 431, 1013 290, 1020 346 and German patent 1,075,373).

It has now been found that the adducts of unsaturated open-chain alkoxyalkenes with more than 2 carbon atoms in the alkene group on halogenated cyclopentadienes have a strong insecticidal potency which in some cases exceeds that of known cyclodienes.

The active ingredients to be used as insect control agents according to the invention are to compounds of the general formula

Cl

Insecticides

Applicant:

Paint factories Bayer Aktiengesellschaft,
Leverkusen-Bayerwerk

Dr. Klaus Schwarzer, Dr. Arnold Hausweiler,

Cologne-Flittard,

and Dr. Günther Unterstenhöfer, Opladen,
have been named as inventors

or bisalkoxyalkenes to halogenated cyclopentaao dienes (better effectiveness against a number of Insects) was used as a comparison substance 1,4,5,6 known from German patent specification 960 989, 7.7-hexachlor-2,3-bis (oxymethylene) -bicyclo [2,2,1] -hepten-5 the formula

, -CH ₂ OH

CH ₂ OH

Cl

in which X stands for a radical of the general formula - CH ₂ - O - R, which can also partially contain chlorine instead of the hydrogen atoms and in which R is a lower alkyl or haloalkyl group and in which Y = X or hydrogen and alkyl - Or haloalkyl radicals.

In German patent specification 960 989 and USA patents 2,841,484 and 2,841,485 even the adducts of unsaturated alcohols or their esters with halogenated cyclopentadienes described. Compared to these known products of analogous constitution, those according to the invention are distinguished compounds to be used by a clearly superior insecticidal effectiveness, as can be seen from the results of corresponding comparative tests reported below.

Used to demonstrate the superior technical properties of the adducts of Monohero to be used as pesticides according to the invention. The compound showed, when used in a concentration of 0.2 ° / ₀ following biological effects:

Checkout on evaluation
after Mortification
in% Cockroaches (Plutella maculipennis) 3 days 0 Fruit flies (Drosophila melanogaster) .. 24 hours 0 Green apple aphids (Aphis pomi) 24 hours 0 Common spider mites (Tetranychus telarius) 48 hours 0 Oat lice (Sitobium granarium) 8 days 0 109 759/404

The compounds to be used according to the invention are used for combating harmful Insects usual way of application, both in the form of solid dusts and liquid combinations can be applied.

As solid extenders or thinners, especially talc, chalk, bentonite, kieselguhr or similar in question. If emulsifiable dusts are to be produced, it is advisable to use them as well suitable emulsifiers, especially those on a non-ionic basis, such as. B. of aryloxy polyglycol ethers, of which different types are on the market.

To produce liquid combinations, solutions of the active ingredients in inert organic solvents, z. B. in alcohols or hydrocarbons, especially chlorinated lower hydrocarbons such as chloroform, trichlorethylene and the like can be used. Also water is in connection with suitable Emulsifiers and solubilizers for the aforesaid Purpose useful. When preparing aqueous formulations, it is expedient to start from a mixture Active ingredient, emulsifier, solubilizer, the latter being mainly dimethylformamide, acetone, Xylene or o-dichlorobenzene come into question and as Emulsifiers the above can be used.

The compounds to be used as insecticides according to the invention are prepared by addition from hexachlorocyclopentadiene to unsaturated open-chain mono- or bis-alkoxy-alkenes and optionally subsequent chlorination with the usual agents.

Example la

Testing of chlorinated 2-isopropyl-oxymethylene, 4,5,6,7,7-hexachlorobicyclo- [1,2,2] -hepten- (5) _on Colorado beetles (Leptinotarsa decemlineata)

The said chlorinated adduct is made with the aid of dimethylformamide as a dissolving aid and benzyl-oxydiphenyl-polyglycol ether (emulsifier) brought into a sprayable aqueous formulation. This is used to spray the potato shoots covered with potato beetles. The following are obtained Results:

Active ingredient concentration
in·/.

0.2
0.02

Dead beetles after 6 days

0 /

/O

100
80

Active ingredient concentration Kill in ° / ₀ after
24 hours 0.2
0.02
0.002 100
100
100

Example 2a

Testing of chlorinated 2,3-bis-isopropyl-oxymethylene -1,4,5,6,7,7 - hexachlor - bicyclo - [1,2,2] - heptenes) on Colorado beetles (Leptinotarsa decemlineata)

The chlorinated adduct is made with the help of dimethylformamide and benzyl oxydiphenyl polyglycol ether and subsequent dilution with water brought into a sprayable formulation. Then sprayed potato shoots populated with Colorado beetles are treated with aqueous emulsions of the concentrations given below to the point of dew. The following results are obtained:

»5

Filter paper disks are treated with the compound mentioned in Example 1a. Then will tested with Drosophila.

Test results

Active ingredient concentration Dead beetles after 6 days Example 2b in"/. V. 0.2
0.02
0.002 100
100
20th

»5 testing on the fruit fly (Drosophila melanogaster)

Filter paper is treated in the same way with the same compound as in Example 2a and then tested with Drosophila.

Dead flies after 24 hours Test results 100
100 Active ingredient concentration
35 in · /. 0.2
0.02

Example 2c

Testing on cockroaches (Plutella maculipennis)

Cabbage shoots that are occupied with caterpillars of the species Plutella maculipennis are associated with the same compound as described in Example 2a, sprayed.

Test results

Active ingredient concentration in"/.

Example Ib
Testing on the fruit fly (Drosophila melanogaster) 0.2
0.02

Kill in% after 4 days

100
100

Example 3a

Testing of chlorinated 2,3-bis-tert-butyl-oxymethylene -1,4,5,6,7,7 - hexachlor - bicyclo - [1,2,2] - hepten- (5) on the fruit fly (Drosophila melanogaster)

The chlorinated adduct mentioned is made with dimethylformamide (solvent aid) and benzyloxydiphenyl polyglycol ether (Emulsifier) and subsequent dilution with water brought into a sprayable aqueous formulation. With this emulsion filter paper discs are treated and tested against

excluding with Drosophila. The following results are obtained:

Active ingredient concentration
in ° / o

0.2
0.02

Dead flies after 24 hours

0 / / 0

100 100

Example 3b

Active ingredient concentration

in ° / o

0.2

0.02

0.002

Killing in% after 4 days

100 100 100

Example 4

Brought aqueous formulation. With this aqueous emulsion filter paper disks are treated and then tested with Drosophila. The following results are obtained:

Active ingredient concentration
in"/. Dead flies after 24 hours 0.2
0.02 100
100

Testing on cockroaches (Plutella maculipennis)

In the same way as described in Example 3a, caterpillars of the species Plutella maculipennis are populated fresh cabbage shoots sprinkled with the same compound. The following results are obtained:

Testing of chlorinated 2-isopropyl-oxymethylene-3 - methyl -1,4,5,6,7,7 - hexachlor - bicyclo - [1,2,2] - hepten- (5) on the fruit fly (Drosophila melanogaster)

The chlorinated adduct is made with the help of dimethylformamide as a solvent and benzyl-oxydiphenyl-polyglycol ether as an emulsifier and subsequent dilution with water into a sprayable

Claims (1)

Claim. Insecticides containing compounds of the general formula as active ingredients Cl- in which X stands for a radical of the general formula - CH ₂ - O - R, which can in some cases also contain chlorine instead of the hydrogen atoms and in which R is a lower alkyl or haloalkyl group and in which Y = X or is hydrogen or alkyl - Or haloalkyl radicals. Documents considered: German Patent No. 960 989; U.S. Patent Nos. 2,841,484, 2,841,485. © 109 759/404 1.62