CH623558A5 - Pesticide - Google Patents

Abstract

A pesticide which contains, as active component, a benzyl 2-isopropyl-4-phenyl-3-butenoate of the formula <IMAGE> in which Y denotes hydrogen, halogen or methyl, and its use for controlling various noxious animals and plants.

Description

       

  
 

** WARNING ** beginning of DESC field could overlap end of CLMS **.

 



   PATENT CLAIMS
1. A pesticide which has a 2-isopropyl-4-phenyl-3-butenoic acid benzyl ester of the formula as active component
EMI1.1
 contains, wherein Y is hydrogen, halogen or methyl.



   2. An agent according to claim 1, which as the active component is the compound of the formula
EMI1.2
 contains.



   3. Use of an agent according to claim 1 for controlling various types of animal and vegetable pests.



   4. Use of an agent according to claim 3 for combating plant-damaging insects and mites and ticks.



   The present invention relates to a pesticide which, as the active component, has a 2-isopropyl-4-phenyl-3-butenoic acid benzyl ester of the formula
EMI1.3
 contains, wherein Y is hydrogen, halogen or methyl.



   Halogen means fluorine, chlorine, bromine or iodine, but especially chlorine.



   The compounds of formula I are z. B. made as follows:
EMI1.4


<tb> <SEP> c113, cH3
<tb> <SEP> CH <SEP> acid binding
<tb> y <SEP> CH = CH-CH-C-OH <SEP> + <SEP> X-CH <SEP> t <SEP> -O <SEP> medium
<tb> <SEP> Y <SEP> 0 <SEP> CN
<tb> <SEP> (11) <SEP> (III)
<tb> <SEP> CH <SEP>, CH3
<tb> <SEP> 3C'H <SEP> 3 <SEP> acid-binding
<tb> <SEP> - <SEP> medium
<tb> y <SEP> CH = CH-CH-C-X <SEP> + <SEP> HO-CH <SEP> t <SEP> -O <SEP> t <SEP>, 1
<tb> <SEP> CH = CH-CH-C-X <SEP> + <SEP> HO-CH
<tb> <SEP> (IV) <SEP> CN <SEP> (V)
<tb> <SEP> CH <SEP> CH
<tb> CH <SEP> 3 <SEP> -H20
<tb> <SEP> / -7
<tb> <SEP> water-binding
<tb> O <SEP> Y <SEP> <SEP> <SEP> CN <SEP> medium
<tb> <SEP> (11) <SEP> (V)
<tb> <SEP> CH3 <SEP> CH3
<tb> <SEP> CH
<tb> <SEP> - <SEP> -ROH <SEP> 1
<tb> 4) <SEP> yr <SEP> kCH = CH-CH-C-OR <SEP> + <SEP> HO-CH <SEP> to <SEP> -OX <SEP> 3

   <SEP> -ROH
<tb> <SEP> 4) <SEP> ¯i / <SEP> - <SEP> H0ClHi $ N
<tb> <SEP> CN
<tb> <SEP> 1 <SEP> (V)
<tb>



   In the formulas 11, IV and V, Y has the meaning given for the formula I. In formulas III and IV, X represents a halogen atom, in particular chlorine or bromine, and in formula VI, R represents C 1 -C 4 -alkyl, in particular methyl or ethyl. Suitable acid-binding agents for processes 1 and 2 are, in particular, tertiary amines, such as trialkylamines and pyridine, furthermore hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals and alkali metal alcoholates such as, for. B. Potassium t.butylate and sodium methylate into consideration. As a water-binding agent for method 3, for. B. dicyclohexylcarbodiimide can be used.

  Processes 1 to 4 are carried out at a reaction temperature between -10 and 100 ° C., usually between 20 and 80 ° C. under normal or elevated pressure and preferably in an inert solvent or diluent. Suitable solvents or diluents are e.g. B. ether and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuan; Amides such as N, N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, especially benzene, toluene, xylene, chloroform and chlorobenzene; Nitriles such as acetonitrile; Dimethyl sulfoxide and ketones such as acetone and methyl ethyl ketone. Method 2 can also be carried out in aqueous solution.



   Starting materials of the formulas II to VI are known or can be prepared analogously to known methods. A method for the preparation of the compound of formula IV is described in Example 1.



   Compounds of the formula I can be present as mixtures of different isomers if non-uniform starting materials are used in the preparation. The various isomer mixtures can be separated into the individual isomers by known methods. These compounds of the formula I are understood to mean both the individual isomers and their mixtures.



   The compounds of formula I are suitable for controlling various types of animal and vegetable pests.



   For example, they can be used to control representatives of the phytopathogenic mites from the genus Tetranychus and Panonychus as well as ticks from the families Dermanyssidae and Ixodidae. In particular, however, they are suitable for controlling insects such. B. the families Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrida Stomoxydae, Trypetidae, Muscidae, Calliphoridae and Pulicidae.



   Above all, the compounds of the formula I are suitable for combating plant-damaging insects, in particular plant-damaging insects in ornamental and useful plants, in particular in cotton crops (for example against Spodoptera littoralis and Heliothis virescens) and vegetable crops (for example against Leptinotarsa decemlineate) and Myzus persicae).



   Active ingredients of formula I also have a very beneficial effect against flies such as. B. Musca domestica and Mükkenlarva.



   The acaricidal or insecticidal effect can be significantly broadened by adding other insecticides and / or acaricides and adapted to the given circumstances. As additives are such. B. org. Phosphorus compounds; Nitrophenols and their derivatives; Formamidines; Ureas; other pyrethrin-like compounds as well as carbamates and chlorinated hydrocarbons.



   It is particularly advantageous to combine compounds of the formula I with substances which have a synergistic or reinforcing effect on pyrethroids. Examples of such connections include. a. Piperonyl butoxide, propynyl ether, propynyl oximes, propynyl carbamates and propynyl phosphonates, 2- (3,4-methylenedioxyphenoxy) -3,6,9-trioxaunecan (Sesamex or Sesoxane), S, S, S-tributyl-phosphorotrithioate, 1, 2-methylenedioxy-4- (2- (octylsulfonyl) propyl) benzene.



   The compounds of formula I are used together with suitable carriers and / or additives. Suitable carriers or additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. B. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.



   Agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding the active compounds of the formula I with the suitable excipients, if appropriate with the addition of dispersants or solvents which are inert to the active compounds. The active ingredients can be present and used in the following processing forms: Solid processing forms:
Dusts, scattering agents, granules (coating granules, impregnation granules and homogeneous granules); Liquid processing forms: a) active ingredient concentrates dispersible in water:
Wettable powders, pastes, emulsions; b) solutions.



   The content of active substance in the agents described above is between 0.1 to 95%, it should be mentioned that concentrations of up to 99.5% of active substance can be used in the application from the airplane or by means of other suitable application devices. The active ingredients of the formula I can be formulated, for example, as follows (parts mean parts by weight): dusts:
The following substances are used to produce a) 5% and b) 2% dusts: a) 5 parts of active ingredient,
95 parts talc; b) 2 parts of active ingredient,
1 part of highly disperse silica,
97 parts of talc.

 

   The active ingredient is mixed with the excipients and ground.



  Granules:
The following substances are used to produce 5% granules:
5 parts of active ingredient,
0.25 parts of epoxidized vegetable oil,
0.25 parts of cetyl polyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (grain size 0.3-0.8 mm).



   The active substance is mixed with epoxidized vegetable oil and dissolved with 6 parts of acetone, whereupon polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and the acetone is then evaporated in vacuo.



  Spray powder:
The following constituents are used to produce a) 40%, b) and c) 25% d) 10% wettable powder: a) 40 parts of active ingredient,
5 parts of sodium lignosulfonic acid,
1 part of dibutylnaphthalenesulfonic acid sodium salt
54 parts of silica; b) 25 parts of active ingredient,
4.5 parts of calcium lignin sulfonate,
1.9 parts of champagne chalk / hydroxyethyl cellulose mixture (1: 1),
1.5 parts of sodium dibutyl naphthalenesulfonate,
19.5 parts of silica,
19.5 parts of champagne chalk,
28.1 parts kaolin; c) 25 parts of active ingredient,
2.5 parts of isooctylphenoxy-polyethylene-ethanol,
1.7 parts champagne chalk / hydroxyethyl cellulose mixture (1: 1),
8.3 parts of sodium aluminum silicate,
16.5 parts of diatomaceous earth, selgur,
46 parts of kaolin;

   d) 10 parts of active ingredient,
3 parts mixture of the sodium salts of saturated fat alcohol sulfates,
5 parts of naphthalenesulfonic acid / formaldehyde condensate sat,
82 parts of kaolin.



   The active ingredient is intimately mixed with the additive in suitable mixers and ground on appropriate mills and rollers. Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.



  Emulsifiable concentrates:
The following substances are used to prepare a) 10% b) 25% and c) 50% emulsifiable concentrate: a) 10 parts of active ingredient,
3.4 parts of epoxidized vegetable oil,
3.4 parts of a combination emulsifier consisting of
Fatty alcohol polyglycol ether and alkylarylsulfonate
Calcium salt,
40 parts of dimethylformamide,
43.2 parts xylene; b) 25 parts of active ingredient,
2.5 parts of epoxidized vegetable oil,
10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide,
57.5 parts xylene; c) 50 parts of active ingredient,
4.2 parts of tributylphenol polyglycol ether,
5.8 parts of calcium dodecylbenzenesulfonate,
20 parts of cyclohexanone,
20 parts of xylene.



   Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.



  Spray agent:
The following constituents are used to produce a) 5% and b) 95% spray: a) 5 parts of active ingredient,
1 part epoxidized vegetable oil,
94 parts of gasoline (boiling limits 160-190 C); b) 95 parts of active ingredient,
5 parts of epoxidized vegetable oil.



   Example 1
Preparation of 2-isopropyl-4-phenyl 3-butenoic acid <-cyano-m-phenoxy-benzyl ester a) 1.5 g of sodium hydride are heated in 60 ml of dimethyl sulfoxide at 70-75 C for 1.5 hours until no more hydrogen escapes.



   7.8 g of ethyl 4-phenyl-3-butenoate are added to the solution cooled to 225 ° C. Then alkylation is carried out with 7.4 g of isopropyl bromide at 15-20 ° C. The reaction mixture is stirred for two hours at 40 ° C. with Water was added and the mixture was extracted several times with ethyl acetate and, after evaporation, the product was chromatographed on silica gel using toluene to give the compound of the formula
EMI3.1
 which can be processed without further cleaning.



   b) A solution of 3.5 g of ethyl 2-isopropyl-4-phenyl-3-butenate, 10 g of 85% KOH, 30 ml of ethanol and 5 ml of water are stirred for 15 hours at 80 ° C. The solution is totally concentrated, mixed with water and washed with a little ethyl acetate After acidification, subsequent extraction and drying, the reaction mixture is stirred with 1.8 g of thionyl chloride in 30 ml of absolute toluene for 12 hours under reflux, and evaporation gives 2-isopropyl-4 -phenyl-3-butenoic acid chloride, which is further processed raw.



   c) 2.8 g of 2-isopropyl-4-phenyl-3-butenoyl chloride and 2.84 g of m-phenoxymandelic acid nitrile in 40 ml of toluene are introduced and 1.2 g of pyridine are added dropwise at 20-25 ° C. You leave
Stir for 12 hours at 20 "C and extracted once with dilute hydrochloric acid and three times with water.



   After drying and evaporation, the compound of the formula is obtained
EMI3.2
 with a refraction of nD2t = 1.573.



   The following connections are also made in an analogous manner:
EMI3.3
    22 nD22fi = 1.576
EMI3.4
    22 = = 1.574.



   Example 2 a) Insecticidal feeding poison effect
Tobacco and potato perennials were sprayed with a 0.05% aqueous active ingredient emulsion (obtained from a 10% emulsifiable concentrate).



   After the covering had dried on, the tobacco and potato plants were populated with caterpillars from Spodoptera littoralis at the L3 stage and from Heliothis virescens at the L3 stage.

 

   The test was carried out at 24 C and 60% relative humidity.



   The compounds according to Example 1 showed in the above test a positive feeding poison effect against Spodoptera littora lis and Heliothis virescens caterpillars.



   B) Insecticidal contact effect
One day before application of the active ingredient, broad beans (Vicia faba) grown in pots were infected with about 200 aphids (Aphis fabae) per plant. A spray liquor in a concentration of 1000 ppm (made from a 25% wettable powder) was applied to the leaves covered with lice by means of a compressed air syringe.



   The ratings were given 24 hours after the application.



  The compounds according to Example 1 showed good contact activity against Aphis fabae in the above test.


    

Claims (4)

 PATENT CLAIMS 1. A pesticide which has a 2-isopropyl-4-phenyl-3-butenoic acid benzyl ester of the formula as active component EMI1.1  contains, wherein Y is hydrogen, halogen or methyl.  2. An agent according to claim 1, which as the active component is the compound of the formula EMI1.2  contains.  3. Use of an agent according to claim 1 for controlling various types of animal and vegetable pests.  4. Use of an agent according to claim 3 for combating plant-damaging insects and mites and ticks.  The present invention relates to a pesticide which, as the active component, has a 2-isopropyl-4-phenyl-3-butenoic acid benzyl ester of the formula EMI1.3  contains, wherein Y is hydrogen, halogen or methyl.  Halogen means fluorine, chlorine, bromine or iodine, but especially chlorine.  The compounds of formula I are z. B. made as follows: EMI1.4 <tb> <SEP> c113, cH3 <tb> <SEP> CH <SEP> acid binding <tb> y <SEP> CH = CH-CH-C-OH <SEP> + <SEP> X-CH <SEP> t <SEP> -O <SEP> medium <tb> <SEP> Y <SEP> 0 <SEP> CN <tb> <SEP> (11) <SEP> (III) <tb> <SEP> CH <SEP>, CH3 <tb> <SEP> 3C'H <SEP> 3 <SEP> acid-binding <tb> <SEP> - <SEP> medium <tb> y <SEP> CH = CH-CH-C-X <SEP> + <SEP> HO-CH <SEP> t <SEP> -O <SEP> t <SEP>, 1 <tb> <SEP> CH = CH-CH-C-X <SEP> + <SEP> HO-CH <tb> <SEP> (IV) <SEP> CN <SEP> (V) <tb> <SEP> CH <SEP> CH <tb> CH <SEP> 3 <SEP> -H20 <tb> <SEP> / -7 <tb> <SEP> water-binding <tb> O <SEP> Y <SEP> <SEP> <SEP> CN <SEP> medium <tb> <SEP> (11) <SEP> (V) <tb> <SEP> CH3 <SEP> CH3 <tb> <SEP> CH <tb> <SEP> - <SEP> -ROH <SEP> 1 <tb> 4) <SEP> yr <SEP> kCH = CH-CH-C-OR <SEP> + <SEP> HO-CH <SEP> to <SEP> -OX <SEP> 3  <SEP> -ROH <tb> <SEP> 4) <SEP> ¯i / <SEP> - <SEP> H0ClHi $ N <tb> <SEP> CN <tb> <SEP> 1 <SEP> (V) <tb> ** WARNING ** End of CLMS field could overlap beginning of DESC **.