DE2520739A1 - PESTICIDE - Google Patents

Description

The present invention relates to a novel pesticide such as an acaricide and an aphicide which is a compound as an active ingredient the general formula

Il

has, wherein R- is an alkyl having 8 to 14 carbon atoms, which can be straight-chain, branched or cyclic, and Rp denotes an alkyl having 1 to 6 carbon atoms, which can be branched or straight-chain, or a cycloalkyl having 3 to 6 carbon atoms.

The present invention also relates to a method of controlling aphids and mites using of the listed compounds.

In U.S. Patents 2,553,647 and 2,553,648, the class of

509847/1

2-Alkyl-3-hydroxy-1 ^ -naphthoquinonecarboxylic acid and its corresponding Described ester derivatives. These compounds are said to have an antagonistic effect against organisms, that cause malaria infections.

Nakanishi et al. JACS 1952, 3910-3915 describes the n-undecyl analogue of 2-alkyl-3-hydroxy-1,4-naphthoquinone. This publication discusses the action of this compound and their use said nothing.

As already stated at the outset, the present invention also relates to a method for controlling mites and aphids by applying the compound to the object to be protected, preferably a plant, namely an acaricidally or aphicidally effective amount of a compound of the formula

wherein R ^ is an alkyl radical having 8 to 14 carbon atoms, straight-chain, branched or cyclic, and R _{2 is} a straight-chain or branched alkyl radical having 1 to 6 carbon atoms or a cycloalkyl radical having 3 to 6 carbon atoms.

The compounds of the formula I are acaricides and aphicides. An effective amount of these compounds is brought into contact with mites or aphids, these pests are killed. The compounds proposed according to the invention can therefore be used to protect plants and animals against the action of mites or aphids.

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The present invention therefore also has acaricidal and aphicidal agents which contain at least one compound of the Formula I included as an active ingredient.

Because of the simplicity of synthesis and greater acaricidal or aphicidal activity, such compounds are the Formula I preferred, in which R ^ is an alkyl radical with 11 to 14 Carbon atoms, either branched or straight-chain, especially straight-chain, and Rp is an alkyl radical having 1 to 4 carbon atoms mean.

The following compounds are particularly preferred because of their very high acaricidal and aphicidal effectiveness:

3-acetoxy-2-n-tetradecyl-1,4-naphthoquinone, 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone, 3-propionyloxy-2-n-tetradecyl-1,4-naphthoquinone, 2-n-dodecyl-3-propionyloxy-1,4-naphthoquinone, 3-cyclopropylcarbonyloxy-2-n-tetradecyl-1,4-naphthoquinone, 3-butyryloxy-2-n-dodecyl-1,4-naphthoquinone, 2-n-dodecyl-3-isobutyryloxy-i, 4-naphthoquinone, 3-cyclopropylcarbonyloxy-2-n-dodecyl-1,4-naphthoquinone, 3-butyryloxy-2-n-tetradecyl-1,4-naphthoquinone.

According to a preferred embodiment of the present invention, the compounds according to the invention are mixed with a top oil, preferably with a lesser amount of top oil, e.g. less than 5 wt .- 6 applied. The one with it The acaricidal effect obtained is greater than the sum effect. Upper oils are discussed in Chapman et al. Selection of a Plant Spray Oil Combining Full Pesticidal Efficiency with Minimum Plant Injury Hazards, Jour. Econ. Ent., 1962, 55: 737-43 described. The obtained mixture of the compound with the oil above is new.

509847/1 166

The compounds of the formula I can be prepared by the procedures as described in the initially cited Article from J.Am. Chem. Soc. and U.S. Patents 2,553,647 and 2,553,648. The final stage of the synthesis can also be carried out by using the appropriate 2-alkyl-3-hydroxy-1,4-naphthoquinone with a suitable acid chloride or anhydride in the presence of at least one Equivalent of amine, such as pyridine or triethylamine, treated. The following examples serve to illustrate the preparation of the compounds used according to the invention.

example 1

Preparation of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone

Ii OC-CH ₃

ⁿ ~ ^C 12 ^H 25

A mixture of 2 parts of 2-n-dodecyl-3-hydroxy-1,4-naphthoquinone, 0.81 part of triethylamine and 0.63 part of acetyl chloride and 50 parts of methylene chloride are stirred at room temperature for 30 hours. The mixture obtained is partitioned between methylene chloride and water. The methylene chloride layer is separated, dried over magnesium sulfate, then filtered and evaporated under reduced pressure. The residue is crystallized from Bxs petroleum ether (boiling point 30 to 60.degree. C.) and gives 1.2 parts of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone with a melting point of 57 to 58.degree.

Example 2

Preparation of 2-n-dodecyl-3-propionyloxy-1,4-naphthoquinone

509847/1 1 66

OCCH ₂ CH ₃

A mixture of 4 parts of 2-n-dodecyl-3-hydroxy-1,4-naphthoquinone, 4.4 parts of propionic anhydride and 50 parts of pyridine is stirred at room temperature for 16 hours. The resulting mixture is then evaporated under reduced pressure to remove the pyridine. The residue is recrystallized from methanol, so that 2.9 parts of 2-n-dodecyl-3-propionyloxy-1,4-naphthoquinone with a melting point of 42 to 44 ^° C. are obtained.

Using an appropriate 2-alkyl-3-hydroxy-1,4-naphthoquinone and a corresponding acid chloride or anhydride can be the compounds listed in Table 1 similarly using the procedures given in Examples 1 and 2.

Table 1

OCR,

509047/1166

R ₁ - ^R 2 Melting point ~ ⁿ " ^C 8 ^H 17
-11-C ₉ H ₁₉ -C ₂ H ₅ 51-53 -Xi-C ₁₁ H ₂₃ -CH ₂ CH ₃ Njp 1.5209 -11-C ₁₁ H ₂₃
" ⁿ ~ ^c 12 ^H 25 —CHpCHpCH-z
-CH (CH ₃ ) ₂
-CH3
—CHpCH-2
—CHpCHpCH- ^ NJp 1.5131
Njp 1.5155
57-58
42-44
N ^ ⁵ 1.5120 -Xi-C ₁₃ H ₂₇ -CH3 -CH ₂ -CH-C ₉ H ₁₀
CH ₃
- (CH ₂ ) ₉ -CH (CH ₃ ) ₂ -CH ₃
CH ₃
-CH-CH ₃ -CH ₂ CH ₃ "GXD -CH ₃ -HC ₁₄ H ₂₉ -CH ₃ 62-63 -11-C ₁₂ H ₂₅ -CH (CH ₃ ) ₂
-CH ₃ Njp 1.5157 -HC ₁₄ H ₂₉ CHpCH-7 52-53 -HC ₁₄ H ₂₉ CHpCHpCH-z 40-41

-HC ₁₄ H ₂₉ -CH I 65-67

503847/1166

Table 1 continued

R ₁

R,

Melting point

-nC ₁₂ H ₂₅

-CH

-CH,

59-61

-nC ₁₂ H ₂₅

50-52

- (CHg) ₄ CH,

1.5133 1.5133

The method of preparation of the compounds used according to the invention is not critical.

The compounds of the formula I are used as acaricides and serve to protect plants and animals against the harmful effects of these pests. In particular, fruit, field crops, vegetables, ornamental plants, birds and other warm-blooded animals including humans are protected.

The acarines come into contact with the compounds to be used according to the invention either in the form of sprays or by walking over surfaces which have been treated with a compound of the formula I, whereby they are irritated and leave this area or be killed if they are one

5098 4 7/1166

effective dose. Most plants or animals can have the presence of a very small number Tolerated by acarins without an apparent deleterious effect, however, the reproductive rate of these pests is enormously. In general, the acarine populations multiply very rapidly, so that they can often no longer be achieved with the usual methods can be brought under control to fight parasites. If a rapid increase in acarines is found, measures must be taken immediately to avoid damage to economically important crops. It exists thus a need for a method for the immediate reduction of the multiplication of acarines and thus for prevention of damage to important crops or animals.

The compounds of the formula I are also valuable aphicides and can therefore be used to protect fruit, field crops and vegetables, Ornamental plants and other plants against the attack of aphids to serve. If they are used against aphids or in locations with aphid infestation, they will be killed or driven away by the plants.

The inventive method in which the Akarinen or Aphids brought into contact with an acaricidally or aphicidally effective concentration of compounds of the formula I. is the preferred method for combating these pests, as e.g. very small amounts of compounds of formula I are acaricidally or aphicidally effective. In addition, the compounds to be used according to the invention are not washed away too quickly from the foliage by rain! In addition, they have no harmful effects on ladybugs, the are important natural enemies for mites and aphids. Furthermore, the connections in the surrounding area become quick reduced. The compounds are also effective against phosphorus-resistant acarine strains.

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The acaricidally or aphicidally effective amount depends on the specific Situation. One of the variables to consider when choosing the amount of the substance is the respective compound itself, then the respective mite or aphid to be controlled, the weather conditions, the type of crop, its stage of development, the volume of the spray to be applied, the population pressure and the Intervals between the individual application steps. For Under certain circumstances, crop protection solutions or suspensions with 5 ppm of active ingredient in a spray solution can already be used be effective. When used outdoors, however, higher volumes, i.e. aqueous spray preparations, are generally used Use 40 to 4,000 ppm active ingredient. Suspensions with 80 to 1000 ppm and in particular those with are preferred up to 500 ppm. Based on the area, 0.03 to 15 kg / ha are generally sufficient, in particular 0.06 to 8 kg, preferably 0.1 to 4 kg. In fruit growing, it is sprayed until drops form.

It may be desirable or expedient to combine the compounds proposed according to the invention with other agricultural Mixing pesticides or additives. Such mixtures often increase the effectiveness of the application to acarins and expand the control range by including other pests such as insects, fungi, nematodes or bacteria. A blend with pesticide (refined petroleum) or top oil shows a greater effect on acarins than the pure Cumulative effect. Other pesticides that use the compounds proposed according to the invention for broadening of the spectrum of activity can be mixed are the following:

Diazinon - 0,0-diethyl-0- (2-isopropyl-4-methyl-6-

pyrimidyl) phosphorothioate 503847/1 166

- ίο -

Disulfoton Phorate

Oxamyl Methomyl Benomyl Captan

Carboxin streptomycin

- 0,0-diethyl-S-2- (ethylthio) ethylphosphorodithioate

- 0, O-diethyl-S- (ethylthio) methylphosphorodithioate

- S-methyl-1 - (dimethylcarbamoyl) -N - / "(methylcarbamoyl) oxy / thiof ormimidat

- S-methyl-N- (methylcarbamoyloxy) thioacetimidate

- 1-butylcarbamoyl-2-benzinidazole carbamine acid-a thyle ster

- N-trichloromethylthiophthalimide

- Ethylenebisdithiocarbamic acid manganese salt

- 5,6-Dihydro-2-methyl-1, ^ - oxathiin-J-carboxanilide

- 2,4-Diguanidino-3 , 5,6-trihydroxycyclohexyl-5-deoxy-2-o- (2-deoxy-2-methylamino- ^ -glycopyranosyl) -3-formylpentofuranoside.

The compounds are particularly suitable for protecting living plants, such as fruit-bearing trees and nut-bearing trees Trees, ornamental trees, forest trees, vegetable plantations, garden crops (including ornamental gardens, small fruits and berries), grain fruits and seeds. Apple trees, peach trees, Cotton, citrus trees, beans and peanuts are particularly sensitive to mite and aphid infestation and can be protected by using the compounds of the invention. To get protection during the Waciist period secure (e.g. from June to August in the northern hemisphere) should a multiple application in the desired At intervals.

Many types of mites - can be caused by the inventive method

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ties are fought. The following is a list of representative mite mites with the type of damage, which cause them given:

Panonychus ulmi and Tetranychus urticae, in general as "orchard mites" are named and very many Deciduous trees attack such as apple, pear, cherry, plum and peach trees; Tetranychus atlanticus, T. cinnabarinus and T. pacificus, which attack cotton, and numerous other plants; Paratetranychus citri and others, the citrus fruits infested; Phyllocoptruta oleivora, which citrus rust causes; Bryobia praetiosa, which affects clover, alfalfa and other plants, and Aceria neocynodomis, which affects grasses and others Infects plants.

Aphids controllable by compounds according to the invention are for example:

Aphis fabae, Myzus persicae, Aphis pomi, Annezphis roseus, Macrosiphum euphorbiae, Toxoptera graminum, Brevicoryne brassicae and Aphis spiraecola.

Useful agents containing the compounds of the formula I can be prepared in a customary manner. These are dusts Granules, tablets, solutions, suspensions, emulsions, wetting powders, emulsion concentrates and the like. Many of these types of application can be used directly. Sprays can be stretched through suitable media and in spray volumes from a few to several hundred liters per hectare can be applied. Concentrated funds are in the first place used as semi-finished products for further formulations. Such semi-concentrates generally contain approximately 1 to 99% by weight of active ingredient (s) and at least one additive a) with about 0.1 to 20% by weight of surfactant (s) and b) with about 5 to 99% solid (s) or liquid (s) diluent (s). In particular, these agents contain the components

5 0 9 δ Λ 7/1 1 6 6

in the following approximate proportions:

Table 2

Active ingredient Dilution
middle Surfactant (s) Mesh powder 20-90 0-74 1-10 oil suspensions, emul
sions, solutions (a
finally emulsions
concentrates) 5-50 40-95 0-15 Aqueous suspensions 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules or tablets 1-95 5-99 0-15

High percentage concentrates 90-99 0-10 0-2

It goes without saying that higher or lower contents of active ingredient can be used depending on the intended use and the physical properties of the compound. Higher surfactant to active ingredient ratios are sometimes used are desired and are obtained by incorporation into the composition or by mixing in the tank.

Typical solid diluents are described by Watkins et al. in the "Handbook of Insecticide Dust Diluents an Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. described. More absorbent diluents are preferred for wetting powders, denser ones for Dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd. Edn., Interscience, New York, described in 1950. A solubility below 0.1 # is

5 0 S 8 4 7/1 1 6 6

preferred for suspension concentrates, whereby solution concentrates should preferably be stable against phase separation at ⁰ ° C. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, list surfactants and the recommended uses. All of these agents can contain minor amounts of additives to prevent foaming, caking, corrosion, microbiological growth, etc. Preferably, the ingredients of the blends should be approved for use by the US Environmental Protection Agency.

The manufacturing processes for the mixtures are known. Solutions are made by simply mixing the ingredients. Fine solids are made by pickling and usually grinding in a hammer mill or mill Jet mill. Suspensions can be prepared by wet milling (see e.g. U.S. Patent 3,060,084). Granules and tablets can be prepared by spraying the active ingredient onto preformed granulated carriers or by agglomeration. See J.E. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147 ff and Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, N.Y., 1963, pp. 8-59 ff.

As a further source of information for the production of the invention For means, reference is made to the following literature:

J.B. Buchanan, U.S. Patent 3,576,834, April 27, 1971, column 5, Line 36 to column 7, line 70 and Examples 1-4, 17, 106, 123-140.

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R.R. Shaffer, U.S. Patent 3,560,616, Feb. 2, 1971, column 3, line 48 to column 7, line 26 and examples 3-9, 11-18.

E. Somers, "Formulation", Chapter 6 in Torgenson, "Fungicides", Volume I ₁ Academic Press, New York, 1967.

Another liquid application, especially for small consumption is suitable is the aerosol form, which is packaged under pressure in a suitable container. The active substance can be in a suspension, emulsion or solution. Solutions are made for ease of manufacture and use preferred. The pressure can be caused by low boiling liquids such as propane or chlorofluorocarbons or by relative soluble gases such as carbon dioxide or nitrogen dioxide are generated. The chlorofluorocarbons are preferred because they combine good solvability and low flammability.

The acaricidal action of the compound of the formula I is illustrated by the following examples.

Example 3

Test units from pots are used for this experiment two red kidney beans in the two-leaf stage per pot. The plants become infected with mites of the species Tetranychus urticae and sprayed with solutions of the compounds according to the invention until drops form. The solutions are made by dissolving weighed amounts of active ingredient in 10 ml of acetone and diluting with water to a volume containing 1: 3,000 of a surfactant, namely TREM 014 *. The degree of destruction was determined two days after spraying.

* TREM 014 is a trademark of Nopco Chemical Company for a polyhydric ester.

503847/1166

Table 3

nC ₁₂ H ₂₅

Connections O

Kill of mites, %

_. Pray concentration , % _

0.005 0.002 0.001 0.0005 0.00025

Il

-C-CH ₃

-C-CH ₂ CH ₃

-C-CH ₂ CH ₂ CH ₃ 100

100

100

99

99

100

90

60
56

ⁿ ~ ^C 12 ^H 25

ⁿ ~ ^C 11 ^H 23

ⁿ " ^C 11 ^H 23

-C-CH (CH ₃ ) ₂

-C-CH,

-C-CH ₂ CH ₃

100

99

98

92

45

26th

ro cn ro ο

CD OO ■ C- -0

Table 3 (continued)

Rr

ⁿ " ^C 11 ^H 23

ⁿ " ^C 12 ^H 25

n-C

12 ^H 25

Killing of the mites, % spray concentration, %

0.005 0.002 0.001 0.0005 0.00025

-C-CH (CH ₃ ) ₂ 100

—C— ^ CHp ) (-

100 100

-CC (CH ₃ ) ₃ 100

100

100 100

99

98 65 93 70

44

41

Example 4

Bean plants were "until droplet formation with the specified Concentrations of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone in TREM 014: water as 1: 3,000 sprayed. The sprayed Plants were left to stand for 3 days, and then with mites of the species Tetranychus urtical.

Assessment was made on the day after infection and 11 days made afterwards.

Spray concentration kill after kill after tration, % first day, % eleven days, %

0.01 99 100

0.005 90 100

0.002 58 mites multiply

themselves

Example 5

Bean plants were treated with the indicated concentrations of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone until the droplets formed in TREM 014: water sprayed as 1: 3,000. The sprayed plants were allowed to stand for 3 days and then with 7 mm Raining rain. After drying, the plants were infected with mites of the species Tetranychus urtical. The review was carried out on the day after infection and 11 days after

Spray concentration kill after kill after tration, % one day, % 11 days, %

0.01 97 100

0.005 94 99

0.002 42 no killing

'509847/1 1 66

Example 6

Apple seedlings about 13 cm high are infected with mites of the species Panonychus ulmi and then until droplets are formed with the indicated concentrations of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone in TREM 014: water sprayed as 1: 3,000. The evaluation was made two days after the spraying.

Spray concentration
tion, % Degree of destruction 0.005 100 0.002 100 0.001 100 0.0005 95 Example 7

Red kidney beans are infected with mites of the species Tetranychus urticae and sprayed with 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone alone and in combination with Λ% UNICO * pesticide oil. Ratings are averages from 3 replicates and are taken two days after spraying. The results show that the values are greater than the total values when compounds according to the invention are used in combination with a spray oil.

link

2-acetoxy-3-dodecyl-1,4 naphthoquinone

concentration

0.002

0.001

0.0005

0.00025

0.0001

Mortification,

100

99

86

23

* UNICO is a trademark of United Co-operatives, Inc. Alliance, Ohio. It is a refined petroleum distillate with approximately 3% inerts and classified as a top oil.

509847/1 166

link

Concentration kill,

2-acetoxy-3-dodecyl-1,4-naphthoquinone + 1% UNICO oil in the spray solution

Λ% UNICO pesticide oil

0.002 100 0.001 100 0.0005 100 0.00025 97 0.0001 60 0

Example 8

Red kidney beans at the two-leaf stage grew to form droplets treated with solutions of 2-dodecyl-3-acetoxy-1,4-naphthoquinone at concentrations of 10, 5 and 2.5 ppm. The plants were allowed to dry. Two sets of two replicates were made of each concentration. A number became infected with normal mites of the species Tetranychus urticae and the other with a methyl parathion-resistant strain. the Results are given below and show that the resistant mite strains when treated with the compounds of the invention were just as sensitive as the normal mites.

Active ingredient concentration, %

Degree of kill in 48 hours, % Normal mites Resistant mites

0.001 0.0005

100
80

100 81

The aphicidal properties of the compounds according to the invention of formula I are illustrated in the following examples.

50S84 7/1166

Example 9

Nasturtium in pots is mixed with aphids of the species Aphis fabae and placed on a rotating table with 2-acetoxy-3-dodecyl-1,4-naphthoquinone sprayed at concentrations of 100, 50 and 25 ppm. The degree of destruction is 72 hours after carried out spraying. The results are shown below.

Spray concentration kill

100 100 89

0 , 01 0 , 005 0 , 0025 example 10

Solutions of the compounds according to the invention are in concentrations of 150 ppm on potted nasturtium plants sprayed on that were infected with aphids of the species Aphis fabae. The spray solutions are made with a hand-held "Son-ofa Gun "® sprayer applied. Du Pont L-144-WDG was in one Ratio 1: 2,000 present in the spray as a wetting agent. The degree of destruction is determined after 24 hours.

R ₁

R ₁ R ₂ degree of destruction,

0.

Ii

-C-CH, 100

0 3 8 4 7/1166

Rp degree of destruction, %

C-CH ₃ 99

C-CH ₂ CH ₃ 98

C ₁₄ H ₂₉ -C-CH ₂ CH ₃ 99

O / ₂

C-CH I 97

-C-CH I 93

₂₅ • C-CH ₂ CH ₂ CH ₃ 98

O
C ₁₄ H ₂₉ C-CH ₂ CH ₂ CH ₃ 87

Example 11

Aphids of the species Myzus persicae on slices, cut from Chinese cabbage leaves, are placed on a rotating table sprayed with acetone solutions of the compounds according to the invention. The leaf disks are under constant environmental conditions Held for 24 hours, after which the degree of destruction is determined. The concentrations used and the percentage Aphid destruction are listed below.

5 0 3 8 4 7/1166

Connections O

C ₁₄ H ₂₉

-C-CH ₃

I! -C-CH ₃

I! -C-CH ₂ CH ₃

I!

—C-CHpCH ^

ii

-C-CH

-C-CH

CH

'CH, CH.

Degree of destruction, %
Spray center! Concentration, %

0.1 0.5 0.01

100

89

100

100

100

66

0.005

90 85 94 98 88

80

83 71

25th

C ₁₂ H ₂₅ C-CH ₂ CH ₂ CH ₃ 12th 100 100 C ₁₄ H ₂₉ IcH ₂ CH ₂ CH ₃ 100 100 example

93

75

79

A 25? 6% emulsifiable preparation of 2 ~ acetoxy-3-dodecyl-1,4-naphthoquinone was applied to Golden Delicius apple trees in a Delaware orchard using a commercially available device upset. The application was carried out four times a week

509847/1166

at intervals, starting on May 8th and in 15.5, 31.1 and 124.4 g / 454.6 liters (0.5, 1 and 4 oz / 100 gallons) quantities. The counts were 3 days after the last Spraying performed and showed excellent control of the aphid Aphis pomae as indicated below. on the non-sprayed control trees ended up being average 573 aphids detected.

Spray concentration, % kill, % 92/100 gallons

0.5

93 , 7 97 , 6 99 ,8th

b 0 9 8 4 7/1 1 B 6

Claims (18)

Claims 1. Pesticidal agent, characterized by a content of one or more compounds the formula OC-R, wherein Rj is an alkyl radical with 8 to 14 carbon atoms which is straight-chain, can be branched or cyclic, and Rp is a branched or straight-chain alkyl radical with 1 to 6 Carbon atoms or a cycloalkyl radical having 3 to 6 carbon atoms represents. 2. Pesticidal agent according to claim 1, gekennzei c h ■ net by a content of top oil. 3. Pesticidal agent according to claim 1, characterized by a content of 3-acetoxy-2-n-dodecyl- 1,4-naphthoquinone. 4. Pesticidal agent according to claim 1, marked 50984 7/1166 net by a content of 2-n-dodecyl-3-propionyloxy-1,4-naphtho chinone. 5. Pesticidal agent according to claim 1, characterized by a content of 3-butyryloxy-2-n-dodecyl-1,4-naphthoquinone. 6. Pesticidal agent according to claim 1 to 5, characterized by a content of liquid and / or solid diluents and / or surface-active agents and / or other pesticides. 7. Pesticidal agent for controlling aphids according to one of claims 1 to 6, characterized in that that it contains 40 to 4,000, in particular 80 to 1,000, preferably 150 to 500 ppm of active ingredient. 8. Pesticide according to one of claims 1 to 6, characterized in that it contains 1 to 99 wt .-? 6 active ingredient and at least a) about 0.1 to 20% by weight of a surfactant and b) contains 5 to 99 % solid or liquid diluent. 9. A method for protecting plants against attack by mites or aphids, characterized in that that one is on the plant or the place to be protected 509847/1166 an acaricidally or aphicidally effective amount of a compound the formula applies, whereby R ^ is an alkyl radical with 8 to 14 carbon atoms that is branched, can be cyclic or straight-chain, and R-2 is a straight-chain or branched alkyl radical with 1 to 6 Carbon atoms or a cycloalkyl radical having 3 to 6 carbon atoms represents. 10. The method according to claim 9, characterized thereby hnet that one applies a compound, where R-j is an alkyl radical with Tl to 14 carbon atoms, either straight-chain or branched, and Rp represent methyl or ethyl. 11. The method according to claim 9, characterized in that treating an animal as an object to be protected. 12. The method according to claim 9, characterized in that the control agent is an agent 509847/1166 used containing 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone. 13. The method according to claim 9, characterized in that the control agent is 2-n-dodecyl-3-propionyloxy-1,4-naphthoquinone contains. 14. The method according to claim 9, characterized that the control agent 3-butyryloxy-2-n-dodecyl-1,4-naphthoquinone contains. 15. The method according to claim 9 ». characterized in that the pesticide apple, citrus or treats peach trees, cotton, peanuts, or beans. 16. The method according to claim 9, characterized in that one apple trees at certain intervals the growing season treated. 17. The method according to claim 9 »characterized in that the active compound is mixed to apply with a top oil. 18. The method according to claim 9, characterized in that 0.03 to 15 kg of active ingredient per hectare, in particular 0.06 to 8 kg, preferably 0.1 to 4 kg per hectare. 509847/1166