CS207681B2 - Acaricide means - Google Patents

Description

SUMMARY OF THE INVENTION The present invention provides an acaricidal composition containing (S) -alpha-cyano-m-phenoxybenzyl (1R, 3R) -3- (2,2-dibromvinyl) -2,2-dimethylcyclopropanecarboxylate (common name Decamethrin) as an active ingredient of the formula I

Br μ | / - \ (C = CH-CH-CH-C-O-CH- (O >)

bZ M

X 1 ^X ₃ ^X ₃ (I) in combination with a substance selected from the group consisting of compounds of Formulas III-VI

Vk '* ^OC 2 ^H 5 (III) (common name Triazophos)

CH

3 \ o-co-ch = c (ch ₃ ) ₂ (IV) (common name

Binapacryl) No ₂

Sn-OH (V) (common name Cyhexatin)

OH

Cl

Cl

CCI ₃ (VI) (common name Dicofol)

These compositions have been found to exhibit a synergistic effect against mites and their eggs.

Alpha-cyano-3-phenoxybenzyl-3- (2,2-dibromvinyl) -2,2-dimethylcyclopropanecarboxylate (German Patent Specification 23 26 077.7) belongs to interesting insecticides from the pyrethrin family, especially in optically active steric configuration (S) [alpha] -cyano-3-phenoxybenzyl (1R, 3R) -3- (2,2-dibromvinyl) -2,2-dimethylcyclopropanecarboxylate (I; common name Decamethrin) [DOS No. 24 39 177, see also M. Elliott et al., Nature 248, 710, 711 (1974)].

Decamethrin, however, has only an inadequate effect against mites and its eggs.

The compounds of formulas III to VI are known plant protection agents. The compound of formula III is known (see German Patent No. 1,670,876) and is used as an insecticide and acaricide with a broad spectrum of activity against absorbent and biting pests, particularly in the cultivation of cotton, fruit, vegetables, grapevine, grain and rice.

Compounds of formulas IV (German Patent Specification No. 1,099,787), V (see U.S. Patent Specification No. 3,264,177) and VI (see U.S. Patent Specification No. 2,812,280) are used as acaricides in the cultivation of fruits, vegetables and other crop plants.

The combination of a compound of formula I with a compound of formula III, IV,

V or VI, in which the weight ratio of the components is between 1: 2 and 50: 1. A ratio of from 1: 1 to 50: 1 and especially from 3: 1 to 30: 1 is preferred. Particularly preferred are mixtures of a compound of formula I with a compound of formula IV or VI in a weight ratio of 1: 1 to 30: 1, furthermore a mixture of a compound of formula I with a compound of formula III in a weight ratio of 1: 1 to 40: 1 a compound of formula V in a weight ratio of 3: 1 to 10: 1.

The pest control compositions of the present invention exhibit a higher activity against mites compared to Decamethrin alone. These compositions act as acaricides, for example, against acarina parasitic on crop plants and animals, Mesostigmata sub-species such as Dermanyssus, Metastigmata, Prostigmata such as Trombicula, Tetranychus and Panonychus, Astigmata and Crypt. because of their synergistic activity, it is successfully used to control the abovementioned pests in considerably lower amounts or concentrations than their individual components.

The active compound mixtures according to the invention can be prepared using solid or liquid inert carriers, adhesives, wetting agents, dispersing agents and grinding aids in the form of wettable powders, emulsions, suspensions, dusts, granules and compositions suitable for application by shoveling. The active compound combinations according to the invention can also be mixed with other insecticides, fungicides, nematicides and herbicides.

As solid carriers, minerals such as aluminum silicates, alumina, kaolin, chalk, silica chalk, talc, diatomaceous earth or hydrated silicas, or preparations of these minerals with special additives such as sodium stearate chalk may be used.

Liquid carriers include organic solvents such as ketones, for example methyl ethyl ketone, methyl isobutyl ketone and isophorone, esters such as butyl acetate and glycol diacetate, ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether and dibutyl ether diethylene glycol, and the like, xylene glycol, and the like. anisole, decalin and tetralin.

Suitable adhesives are cellulose sticky products or polyvinyl alcohols.

Suitable wetting agents are all suitable emulsifiers, such as oxethylated alkylphenols, polyglycol ethers of fatty alcohols, polyglycol esters of fatty acids, salts of arylsulphonic or alkylarylsulphonic acids, methyltauride salts or soaps.

Sulfite waste liquor salts, naphthalenesulfonic acid salts and, in certain circumstances, hydrated silicic acid or diatomaceous earth may be used as dispersants.

Suitable grinding aids are inorganic or organic salts, such as sodium sulfate, ammonium sulfate, sodium carbonate, sodium bicarbonate, sodium thiosulfate, sodium stearate and sodium acetate.

The acaricidal compositions according to the invention may, depending on the type of composition, contain 2 to 90% of the active ingredient in combination with the abovementioned excipients and carriers. These compositions are preferably used in the form of an emulsion concentrate containing 10 to 70% by weight of the active ingredient mixture and 5 to 15% by weight of the surfactant, the remainder being up to 100% by weight being an organic solvent. These compositions are diluted with a conventional diluent, preferably water, to the desired application concentration prior to application.

For the so-called ULV process (Ultra-Low-Volume), in which also highly concentrated mixtures are applied from airplanes by means of nozzles, pest control agents containing 20 to 95% by weight of the active compound mixture according to the invention and 80 to 5% by weight of aliphatic and / or aromatic mineral oils and / or ketones having a boiling point in each case above 120 ° C, and / or vegetable oils, such as cottonseed oil or castor oil, and / or liquid emulsifiers such as ethoxylated alkylphenols, e.g. 15 ethylene oxide units per molecule.

The concentrations of the active compound mixtures used in the spray suspensions vary depending on the type of application and the climatic conditions, in particular temperature and humidity.

These concentrations may, for example, be in the range of 0.005 to 0.05% by weight in spray-applied compositions against mites and their eggs, although concentrations of more than 0.1% by weight may, of course, be used, but this generally represents less technical effect. For combinations with a higher proportion of the compound of formula I, these concentrations are usually in the upper part, for combinations with a lower proportion of the compound of formula I

mostly at the bottom of this range. In the next section Examples of compositions according to the invention are given. A composition comprising a concentrate thereof combination of substances Decamethrin (I) and Binapacryl (IV) in the form emulsions- Component Weight ratio I: IV 1 - 1 That made the score 4 - 1 10: 1 Decamethrin (technical, 95%) Binapacryl 2.53 2.53 2.53 (technical, 97%) 2.53 0.63 0.25 calcium dodecylbenzenesulfonate (Phenylsulfonate Ca 3.00 3.00 3.00

Component

Weight ratio I: IV

That made the score 4 - 1

10: 1 castor oil polyglycol ether

(Emulsogen ED 360 3.00 3.00 3.00 triisobutylphenol polyglycol ether (Sapogenat T 100®) 0.50 0.50 0.50 stabilizer (antioxidant) 0.50 0.50 0.50 aromatic solvent (Solvesso 100®) 87.94 89.84 90.22 100.00 100.00 100.00

A composition comprising a combination of Decamethrin (I) and Triazophos (III) in a form

emulsion concentrate Component Weight ratio I: III 3 - 1 30: 1 50: 1 Decamethrin (technical, 95%) Triazophos 6.73 6.73 11.05 (technical, 92%) calcium dodecylbenzenesulfonate (Phenylsulfonat Ca ®) 2.16 0.23 0.23 8.50 8.00 7.50 castor oil polyglycol ether (Emulsogen El 400 ®) 3.00 3.00 3.00 triisobutylphenol polyglycol ether (Sapogenat T 11 0 / T 300 ®) 1.00 1.50 2.00 epoxylated soybean oil (Kronos S ®) 0.50 .0,50 0.20 an antioxidant 0.50 0.50 0.80 xylene 77.61 79.54 75.22 100.00 100.00 100.00

3. A composition comprising a combination of Decamethrin (I) and Cyhexatin (V) in the form of a wettable powder

Component Weight ratio I: V

8: 1

Decamethrin (technical, 95%) 8.40 Cyhexatin (technical, 90%) 1, ” Sodium dinaphthylmethane- disulfonic acids 9.00 oleoyl-N- sodium -me thy 11 aur i du 3.00 ligninsulfon sodium acid 3.00 diatomaceous earth 75.49 100.00

4. Composition containing a combination of Decamethrin (X) and Dicofol (VI)

(a) Emulsion concentrate

Component Weight ratio That made the score 4 - 1 Decamethrin (technical, 95%) 4.20 Dicofol (technical, 90%) 1.10 calcium salt of dodecylbenzene- sulfonic acids (Phenylsulfonate Ca ®) 5.50 castor polyglycol ether oils (Emulsogen EL 360 ®) 4.00 trii sobutylfenolpolyglykol- ether (Sapogenat T 300 ®) 1, 80 an antioxidant 1.00 xylene 82.40 100.00

b) ULV application solution

Component Weight ratio I: VI

That made the score 4 - 1

Decamethrin (technical, 95%) 4.20 Dicofol (technical, 90%) 1, 10 mixture of high-boiling aromatics (Solvesso 150®) 40.00 rapeseed oil 54.70 100.00

The biological activity of the compositions of the invention is illustrated by the following examples.

Examples 1 to 4

Combinations of compounds I and III to VI are emulsified in water to achieve the concentrations of the active ingredients listed in the following tables. The resulting mixtures are then sprayed with bean plants (Phaseolus vulgaris), which are heavily infested with the complete population (i.e., all moving and stationary stages, including eggs) of the European spider mite (Tetranychus urticae) until the drip begins. For comparative purposes, emulsions of the individual components at appropriate concentrations are used. After the spray coating has dried, the plants are transferred to a greenhouse.

The following tables show the results obtained microscopically 8 days after treatment.

Example I + III combined weight ratio I: III = 30: 1

Active substance Concentration effective substances in spraying (mass%) Effect (% mortality) acaricidal ovicidní mixture of active ingredients I + III I = 0.025 III = 0.00078 - , 00 AND 0,025 - 50 III 0.00078 - 25 mixture of active ingredients I = 0.0125 75 I + III III = 0.00039 AND 0.0125 - 40 III 0.00039 - 0 mixture of active substances I = 0.0063 90 45 I + III III = 0.0002 AND 0,0063 35 25 III '0.0002 ⁴⁰ 0 mixture of active ingredients I = 0.0031 80 35 I + III III = 0.000098 AND 0.0031 10 10 III 0.000098 , 0 0 mixture of active ingredients I = 0.0016 35 30 I + III III = 0.000048 AND 0,0016 5 0 III 0.000048 0 0 Example 2 combination I + IV weight ratio I: IV = That made the score 4 - 1 Active substance Concentration effective Effect (% mortality) substances in spraying (mass%) acaricidal ovicidní mixture of active ingredients I = 0.0063 80 75 I + IV IV = 0.0016 AND 0,0063 35 25 IV 0,0016 40 25 mixture of active ingredients I = 0.0031 50 40 I + IV IV = 0.00078 AND 0.0031 10 10 IV 0.00078 20 May 10

Active substance Concentration effective substances in spraying (mass%) Effect (% mortality) acaricidal ovicidní mixture of active ingredients I = 0.0016 25 25 I + IV IV = 0.00039 AND 0,0016 5 0 IV 0.00039 5 0

Example 3 I + V combination I: V weight ratio = 8: 1

Active substance Concentration of the active substance in the spray (mass%) mixture of active substances I I + V V I

IN

0.0125

0,0016

0.0125

0.0016 Active ingredient mixture I = 0.0063 I + V V = 0.00078

I 0,0063

At 0.00078

Ovicidal effect (% mortality) o

Example 4 combination I + VI weight ratio I: VI = 4: 1

Active substance Concentration effective substances in spraying (mass%) Effect (% mortality) acaricidal ovicidní mixture of active ingredients I = 0.0125 - I + VI VI = 0.0031 60 AND 0.0125 - 30 VI 0.0031 - 0 mixture of active ingredients I = 0.0063 I + VI VI = 0.0016 80 40 AND 0,0063 20 May 10 in/ 0,0016 40 0 mixture of active ingredients I = 0.0031 I + VI VI = 0.00078 50 20 May AND 0.0031 15 Dec 0 VI 0.00078 10 0

Claims (2)

SUBJECT OF THE INVENTION An acaricidal composition comprising as active ingredient a combination of component A consisting of a compound of formula I About CN Br ¹¹ I, C = CH-CH-CH-C-O-CH - (Q x Br ^from (I) ° AO> and a component B selected from the group consisting of formula III to VI / (5Vn-N t OCoH), 2 ⁿ 5 (III) (IV) (V) (VI) in a weight ratio of compound of formula I to component B of from 1: 2 to 50: 1. 2. The composition of item 1, with a ratio of from 1: 1 to 50: 1. characterized in that it comprises the active ingredients A and B in a mass of 3 wt. The composition of item 1, with a weight ratio of from 3: 1 to 30: 1. characterized in that it contains the active ingredients A and B in the composition of Nordography. n. p. plant 7, Most