CH457029A - Pesticides - Google Patents

Description

  

  



  Pesticides
The present invention relates to a pesticide containing a compound of the general formula as the active component
EMI1.1
 where Ri and Ra are lower aliphatic radicals and Ra is hydrogen or chlorine.



   The new funds are suitable for. B. to control harmful insects, acarids, nematodes and gastropods. The action against harmful insects, aphids and acarids should be emphasized, with the new compounds acting on their various stages of development, such as eggs, larvae and imagines. The new compounds act both as feeding poisons and as contact poisons and are distinguished above all by their systemic effectiveness.



  Their low toxicity to bees is also particularly beneficial. The new compounds of general formula (I) can, for. B. be prepared in such a way that a compound of the general formula
EMI1.2
 in which R3 has the meaning given above in the case of the general formula (I), with a trialkyl phosphite of the general formula
EMI1.3
 wherein Ro and RZ have the meaning given above in the case of the general formula (I) and R4 is a lower aliphatic radical, in the presence of an inert organic solvent, e.g.

   B. chlorobenzene, sund at elevated temperature, preferably between 50 and 150 C, with splitting off a compound R4CI.



   Those compounds of the general formula (I) in which R 1 and R 2 are the methyl or ethyl radical and R g is chlorine are distinguished by a particularly favorable action against the pests mentioned at the outset.



   In addition to the new active ingredients of the general formula (I), the new agents contain other components. There are thus numerous application forms for the new active ingredients, which will be discussed in more detail below:
The sprayable solutions for direct use contain z. B. mineral oil fractions of high to medium, in particular above 100 C boiling range, such as diesel oil or kerosene, coal tar oil or oils of vegetable or animal origin and hydrocarbons, such as alkylated naphthalenes, tetrahydronaphthalene, xylene mixtures, cyclohexanols and optionally also ketones, chlorinated hydrocarbons, such as Tetrachloroethane, trichlorethylene or tri- and tetrachlorobenzenes.



   Solutions of the active ingredients in water and, if appropriate, emulsion concentrates, pastes or wettable wettable powders are suitable for use in aqueous application forms. Suitable emulsifiers or dispersants are nonionic products, e.g. B. Condensation products of aliphatic alcohols, amines or carboxylic acids with a long-chain hydrocarbon radical of about 10 to 30 carbon atoms with ethylene oxide,

   such as the condensation product of octadecyl alcohol and 25 to 30 mol of ethylene oxide or that of soy fatty acid and 30 mol of ethylene oxide or that of technical oleylamine and 15 mol of ethylene oxide or that of dodecyl mercaptan and 12 mol of ethylene oxide. However, condensation products of ethylene oxide with hydroaromatic polycyclic carboxylic acids or amines can also be used.

   Among the anion-active emulsifiers that can be used, there may be mentioned: the sodium salt of dodecyl alcoholsulfuric acid ester, the sodium salt of dodecylbenzenesulfonic acid, the potassium or triethanolamine salt of oleic acid or abietic acid or mixtures of these acids or the sodium salt of petroleum sulfonic acid. Quaternary ammonium and phosphonium compounds, such as. B. the cetylpyridinium chloride or the Dioxyäthylbenzyldodecylammoniumchlorid into consideration.



   The dusts or grit used contain talc, kaolin, bentonite, sand, calcium carbonate, calcium phosphate, but also coal, cork flour and wood flour and other materials of vegetable origin as solid carriers. The various preparations can in the usual way contain an addition of substances which improve the distribution, the adhesive strength or the penetration capacity; as such substances, fatty acids, resins, glue, casein or z. B. Alginates. The use of the preparations in granulated form is also very useful. The new compounds can be present as the only active ingredients in the pesticides, or else in combination with other insecticides, acaricides, nematocides, molluscicides.



  The use of such preparations in crop protection takes place according to the usual spraying, pouring, dusting and smoking processes.



   In the following examples, parts mean parts by weight; Percentages mean percentages by weight; the temperatures are given in degrees Celsius.



   example 1
1. 30 parts of α, α-dichloroacetoacetic acid diallylamide (boiling point 0.17 110-115) are heated to 130 in 50 parts by volume of chlorobenzene. 16.35 parts of trimethyl phosphite are added dropwise over the course of 5 minutes and the temperature is then kept at 130-140 for a further hour. The reaction product of the formula
EMI2.1
 is distilled in a high vacuum: boiling point o.1 145-150.



  Analysis: Cl2HogClNO P found: N 4, 0, P 9, 3%; calculated: N 4, 3, P 9, 6%
2. In an analogous manner, the compound of the formula is obtained from 30 parts of a, a-dichloroacetoacetic acid diallylamide and 21.9 parts of triethyl phosphite
EMI2.2
 Kp. O. 5 160-162.



  Analysis: C14H23CINOsP found: N 4, 0, P 8, 4%; calculated: N 4, 0, P 8, 8%
3. In an analogous manner, the compound of the formula is obtained from 30 parts of a-monochloroacetoacetic acid diallylamide (boiling point 0.2103) and 18.9 parts of trimethyl phosphite
EMI2.3
 Bp 0.05 126.



  Analysis: C12H2oNO5P found: N 4, 9, P 10, 7%; calculated: N 4, 8, P 10, 7%
4. In an analogous manner, the compound of the formula is obtained from 30 parts of α-monochloroacetoacetic acid diallylamide and 25.3 parts of triethyl phosphite
EMI2.4
   KpjosoÏ 131.



  Analysis: C14H24NO5P found: N 4, 6, P 9, 7%; calculated: N 4, 4, P 9, 8%
Example 2
There were 2 parts of a condensation product according to Example 1, Nos. 1 and 2 with 1 part of the condensation product from 1 mol of tert. Octylphenol and 8 moles of ethylene oxide and 7 parts of isopropanol 'mixed. A clear solution was obtained which was used as a spray concentrate and which could be emulsified by pouring it into water.



   To determine the contact effect on aphids, the following experiment was carried out, using spray liquors with 0.08, 0.04, 0.02 and 0.01% active ingredient content: P, green beans that were heavily infested with aphids were sprayed on all sides and afterwards 48 hours noticed the effect. The results obtained are summarized in Table I below.



   A symbol is used for each plant. + means that there are no live lice.



   table
Concentration Compound Compound of the active ingredient Example 1 Example 1 in the spray mixture No. 1 No. 2 0, os ++ ++ 0, 04% ++ ++
0.02% ++ ++
0.01% + + + +
Compounds No.s also showed a clear aphicidal effect under the above test conditions.



  3 and 4 according to example 1.



   Example 3 a) To determine the acaricidal effect on the red spider mite, Tetranychus urticae, spray liquors of the composition given above in Example 2, each containing 0.04% of the compounds listed under 1. and 2. in Example 1, were used.



  Test method:
Broad beans, which are heavily infested with red spider mites, are sprayed on all sides with the spray liquor in question and the acaricidal or ovicidal effect is determined after 7 days.



   Compounds Nos. 1 and 2 according to Example 1 showed that all spider mites had been killed after 7 days at the latest. b) Against the black beetle, Gastroidea viridula, the compounds Nos. 1 and 2 according to Example 1, used in an active ingredient concentration of 0.04%, also showed very good activity, that is to say a killing effect of 100%.



   Compounds Nos. 1 and 2 according to Example 1 also have good to very good food poison action against Musca domestica, Carausius morosus and Orgyia gonostigma.



      PATENT CLAIMS I. Pesticides containing a compound of the general formula as active component
EMI3.1
 where Ri and R2 are lower aliphatic radicals and Rs is hydrogen or chlorine.

 

Claims (1)

II. Use of the agent according to claim I for combating harmful insects, acarids, nematodes and gastropods. SUBClaims 1. Agent according to patent claim I, containing as active component a compound of the general formula given in patent claim I, in which Ri and R2 denote the methyl or ethyl radical and R3 denotes chlorine. 2. Agent according to claim I, containing the compound of the formula as the active component EMI3.2