DE1922926A1 - 2-Alkyl-4,6-dinitrophenol derivatives, processes for their preparation and their use as insecticidal and acaricidal active ingredients - Google Patents

Description

LE VERKU S E N - Bayerwerk Patent department

S.

2-alkyl-4,6-dinitrophenol derivatives, process for their Production and their use as insecticidal and acaricidal active ingredients

The present invention relates to new 2-alkyl-4,6-dinitrophenol derivatives, which have insecticidal and acaricidal properties and processes for their manufacture.

It is already known that certain 2-alkyl-4,6-dinitrophenol derivatives e.g. the ester of the formula

, 3 Q-C-OH = GH-OH,

^C 6 ^H 1 3-

can be used as acaricides (see The Journal of Horticultural Science 34, 39-50 (1959)).

It has been found that the new 2-alkyl-4 $ 6-dinitrophenol derivatives of the general formula

Le A 12 194

(I)

009847/1853

in which

R represents branched alkyl with 3-12 carbon atoms,

R «represents hydrogen or methyl,

R "represents hydrogen, alkyl, haloalkyl or alkenyl,

R " ^{1 represents} alkyl, alkenyl, cycloalkyl optionally substituted by halogen, cyano or alkoxy, aralkyl optionally substituted by halogen or optionally substituted phenyl,

have strong insecticidal and acaricidal properties.

It has also been found that the 2-alkyl-4> 6-dinitrophenol derivatives of formula (I) obtained when one

a) 2-Alkyl-4 »6-dinitrophenols of the formula

(II)

in which R and R ^{1 have} the meaning given above,

with isocyanates of the formula

R "'- NGO (III)

in which R ^{HI has} the meaning given above, with the exception that R ^H 'must not stand for cyanoalkyl,

optionally reacts in the presence of a solvent, or Le A 12 194 - 2 -

009847/1863

b) 2-alkyl-4,6-dinitrophenyl chlorocarbonate of formula

(IV)

in which
R land R ^{1 have} the meaning given above,

with secondary amines of the formula

/ R "

mr (ν)

in which

R "and R ¹¹ V have the same meaning as above, with the exception that R" must not stand for hydrogen,

optionally reacted in the presence of a solvent.

Surprisingly, the 2-alkyl-4,6-dinitrophenol derivatives obtainable according to the invention show a higher level of insecticidal properties and acaricidal activity than the prior art 2-alkyl-4,6-dinitrophenol derivatives which chemically are the closest active ingredients with the same type of action. The substances according to the invention thus represent an enrichment of technology.

Using 2 sec-butyl-4,6-dinitrophenol and methyl isocyanate as starting materials, the course of the reaction can according to Method (a) represented by the following diagram ! ■ will:

le A 12 194 - 3 -

9847 / 18S3-

C ₀ H ^ -CH

_{+ CH} ^ _NC0

2 5

0-C-ITH-OH

NO ₉ 2

When using the chlorocarbonic acid ^ -sec.-butyl ^, 6-dinitrophenyl ester and dimethylamine as starting materials, the reaction according to process (b) can be represented as follows:

'2 ^iX 5

0-6-01

? ^H 3

C ₉ Hc-CH ^ -

O-C-N "

^f ^ CH

n ^N0 2

NO,

The phenols to be used for the reaction according to the invention are clearly characterized by the formula (II) given above. Xn of the formula, R preferably represents alkyl having 3-8 carbon atoms, especially isopropyl, sec-butyl, tert-butyl, pentyl- (2), octyl- (2), octyl- (3) * R ¹ represents Hydrogen or methyl.

As an example of the phenols which can be used according to the invention, the following may be mentioned in detail:

2-isopropyl-4> 6-dinitrophenol, 2-sec-butyl-4 »6-dinitrophenol, 2-sec-butyl-5-methyl-4 »6-dinitrophenol, 2-tert-butyl-4> 6-dinitrophenol, 2-tert-butyl-5-methyl-4,6-dinitrophenol, 2- (pentyl- (2)) - 4,6-dinitrophenol, 2- (octyl- (2)) - 4,6-dinitrophenol, 2- (octyl- (3)) -4,6-dinitrophenol, 2- (decyl- (2)) -4,6-dinitrophenol.

The isocyanates to be used for the reaction according to the invention are clearly characterized by the formula (III).

Le A 12 194

4 -

1 SSi

R " ¹ therein preferably represents alkyl with 1-14 carbon atoms, which can be substituted by chlorine or bromine or by alkoxy with 1-4 carbon atoms, for alkenyl with 3-4 carbon atoms, for cycloalkyl with 5-7 carbon atoms in the ring system; for aralkyl with 1-4 carbon atoms in the aliphatic chain and phenyl as an aromatic radical, which can be substituted by chlorine and bromine; as well as for phenyl, which is substituted by halogen (preferably chlorine and bromine), alkyl with 1-12 carbon atoms, Haloalkyl (preferably lower haloalkyl radicals, especially

with chlorine and / or fluorine as halogen such as trichloromethyl and trifluoromethyl), for alkoxy and / or alkyl mercapto, each with 1-4 carbon atoms.

Examples of such isocyanates are:

Methyl isocyanate, ethyl isocyanate, propyl isocyanate, isopropyl isocyanate, Butyl isocyanate, isobutyl isocyanate, tetradecyl isocyanate, 2-chloroethyl isocyanate, 2-bromoethyl isocyanate, methoxymethyl isocyanate, 3-ethoxypropyl isocyanate, allyl isocyanate, cyclohexyl isocyanate, benzyl isocyanate, 4-chlorobenzyl isocyanate, Phenyl isocyanate, 3-chlorophenyl isocyanate, 4-chlorophenyl isocyanate, 4-bromophenyl isocyanate, 3,4-dichlorophenyl isocyanate, 3-methylphenyl isocyanate, 4-chloro-3-methylphenyl isocyanate, 3-chloro-4-methylphenyl isocyanate, 4-dodecylphenyl isocyanate, 4-trifluoromethylphenyl isocyanate, 3-chloro-4-trifluoromethylphenyl isocyanate, 3-trifluoromethylphenyl isocyanate, 3-chloro-4-methoxyphenyl isocyanate, 4-methyl mercaptophenyl isocyanate, 4-ethyl mercaptophenyl isocyanate.

The 2-alkyl-4,6-dinitrophenyl chlorocarbonate which can be used for the process according to the invention are sufficiently characterized by the formula (IV). R and R ¹ have the same meaning as given for formula (II). As examples of such-

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0 09847/1853

tiger phenyl chlorocarbonate are: chloroformic acid-2-sec-butyl-4,6-dinitrophenyl ester, chloroformic acid-2-tert-butyl-4 t 6-dinitrophenyl ester, chloroformic acid-2-octyl (2) -4 '6-dinitrophenyl . '

The secondary amines which are used for the process according to the invention are clearly characterized by the formula (V). In the formula, R "stands for alkyl with 1-14 carbon atoms and alkenyl with 3-4 carbon atoms, optionally substituted by halogen, preferably chlorine or bromine. R ¹ " has the same meaning as described for formula (III). In addition, R "'stands for a cyanoalkyl radical with 3-8 carbon atoms in which the cyano group is geminal to the nitrogen atom of the amine.

Examples of the secondary amines which can be used according to the invention are: dimethylamine, diachylamine, diisopropylamine, Dibutylamine, diisobutylamine, didodecylamine, methyldecylamine, Methyldodecylamine, methyl-2-chloroä1; hylamine, methyl-2-cyanopropyl- (2) -amine, Diallylamine, ethylcyelohexylamine, methylbenzylamine, Methylaniline, isobutylaniline, N-ethyl-2-chloroaniline, Methyl-o-toluidine, butyl-m-toluidine, N-methyl-4-tert-o-butylani- lin, N-methyl-4-trifluoromethylaniline, N-methyl-4-propylmercaptoaniline.

The isocyanates used for process (a) according to the invention are known. The use of chlorocarbonic acid € -alkyl-4,6-dinitrophenyl ester are new, but can be achieved by reacting the corresponding phenols with excess phosgene in the presence of a hydrogen chloride acceptor, preferably a tert. Amine, at temperatures around 0 ° C in the usual way getting produced. The chlorocarbonic acid phenyl esters fall here in sufficiently pure form and can be used directly.

Le A 12 194 - 6 -

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The reactions according to the invention are preferably carried out in the presence of a diluent. When working with solvents, preference is given to using those "which do not react with the isocyanates or chlorocarbonic acid esters. Examples of such solvents are: hydrocarbons such as benzene, toluene, chlorinated hydrocarbons such as methylene chloride, dichloroethane, chloroform, chlorobenzene, dichlorobenzene, ither such as diethyl ether, dibutyl ether, Tetrahydrofuran, dioxane, and any mixtures of the solvents mentioned.

In the reaction of the phenols with the isocyanates, all catalysts customary for such a reaction can be used will. These preferably include tertiary amines such as triethylamine or pyridine.

The reaction temperatures can be varied within a relatively wide range. The reaction of the phenols with the isocyanates is generally carried out between room temperature and 100 ° C., preferably between 40 and 60 ° C .; the reaction of phenyl chlorocarbonate with the secondary amines is generally carried out in a temperature range between -20 and 50 ° C, preferably at temperatures between -5 and +10 ⁰ C.

In general, the reactants will be approximately equimolar Proportions used.

The reaction of the phenols with the isocyanates can, for example, be carried out in such a way that a solution of the corresponding Phenol, the corresponding isocyanate and a few drops of pyridine in methylene chloride heated to boiling for 4-5 hours and after cooling down in a vacuum. The mostly crystalline products can be recrystallized from white spirit will.

To implement the phenyl chlorocarbonate with secondary ! mining is "for example © Ine solution dee corresponding

009847/1 ^ 53

Eaters in benzene or ether at O - 10 ⁰ C was treated dropwise with the appropriate amine was added, the solution stirred for a short time at room temperature, then precipitated is suction filtered AlNiN hydrochloride and the solvent evaporated in vacuo. The resulting reaction products are mostly oily and can be cleaned by falling over from hot petroleum ether.

The active ingredients according to the invention have low toxicity to warm-blooded animals and phytotoxicity have strong insecticidal and akarizl.de effects. The effects set in quickly and last a long time. You can therefore with good success for the control of harmful sucking and biting insects, Diptera as well as mites are used in the plant protection area and in the hygiene, because of their high alkali resistance especially for treating whitewashed walls.

The sucking insects mainly include aphids, such as the peach aphid (Myzus persicae). the black bean aphid (Doralis fabae); Scale insects, such as Aspidiotus hederae, lecanium hesperidum, Pseudococcus maritimusj Thysanoptera, such as Hercinothrips fermoralis; and bed bugs such as the beet bug (Piesma quadrata) and the bed bug (Cimex lectularius).

The biting insects mainly include caterpillars such as Plutella maculipennis, Lymantria disparj beetles, such as the grain beetle (Sitophilus granarius), the Colorado potato beetle (leptinotarsa decemlineata), but also species living in the ground such as wireworms (Agriotes sp.) and white grubs (Melolontha melolontha); Cockroaches, such as the German cockroach © lattella germanica) j Orthoptera, such as the cricket (Acheta domesticusj termites, like Reticulitermes; Hymenoptera, like ants.

The Diptera include in particular the flies, such as the fruit fly (Drosophila melanogaster), the Mediterranean fruit fly (Ceratitis capitata), the housefly (Musca domestica) and Mosquitoes, such as the mosquito (Aedes aegypti).

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Among the mites, the spider mites (Tetranychidae) are particularly important, such as the common spider mite (Tetranyehus urticae), the fruit tree spider mite (Panonychus ulmi); Gall mites, such as the currant gall mite (Eriophyes ribis) and tarsonemids such as Tarsonemus pallidus; as well as ticks.

The active compounds according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These will produced in a known manner, e.g. by mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifying agents and / or dispersants. If water is used as an extender, organic solvents, for example, can also be used can be used as co-solvents. As a liquid Solvents are mainly used: aromatics such as xylene and benzene, chlorinated aromatics such as chlorobenzenes, Paraffins such as petroleum fractions, alcohols such as methanol and butanol, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; as solid carriers: natural rock flour, kaolins, clays, talc and chalk, and synthetic rock flour, such as finely divided ones Silicic acid and silicates; as emulsifiers: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, Alkyl sulfonates and aryl sulfonates; as a dispersant: e.g. lignin, sulphite waste liquors and methyl cellulose.

The active compounds according to the invention can be present in the formulations as a mixture with other known active compounds.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90,

The active compounds can be used as such, in the form of their formulations or in the form of the use forms prepared therefrom, such as

Le A 12 194 - 9 -

009847/1853

Ready-to-use solutions, emulsions, suspensions, powders, pastes and granulates can be used. The application happens in the usual way, e.g. by spraying, splattering, scattering, dusting and watering.

The active ingredient concentrations can be varied over a wide range. In general, active ingredient concentrations are used from 0.001 to 20 percent by weight, preferably from 0.002 to 5.

Should the active ingredient preparations according to the ULV process (ultra-low-volume method) are applied so, lie the active ingredient concentrations are very high, between 40 and 95 percent by weight.

The 2-alkyl-4,6-dinitrophenol derivatives obtainable according to the invention also show a fungitoxic effect, e.g. against powdery mildew and soil-borne fungi. You can therefore used as a dressing and soil treatment agent for combating fungal plant diseases. After all, they have an antimicrobial effect and a repellent effect against warm-blooded animals.

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Example a
Tetranychus test

Solvent 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount Solvent containing the specified amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Bean plants (Phaseolus vulgaris), which are approximately 10 to 30 cm in height, sprayed until dripping wet. These bean plants are strong with everyone Developmental stages of the common spider mite (Tetranychus urticae) infested.

After the specified times, the effectiveness of the active ingredient preparation is determined by counting the dead animals. The degree of destruction obtained in this way is indicated in #. 100 io means that all spider mites have been killed, 0 # means that none of the spider mites have been killed.

Active ingredients, active ingredient concentrations, evaluation times and results are shown in the following table:

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0098A7 / 1853

1922928

T a btl.l e (plant-killing mites )

Tetranychus test

Active ingredient

Active ingredient concentrate in %

Degree of destruction in % after

48 h

0? ^H 3 O-C-CH = CH-CH,

NO

(known)

CH, O-C-NH-CH,

0.02
0.002

0.02
0.002

100 0

100 95

0 H ₇ 0 , 02 CH ₅ 0-C-NH-C, 0 , 002 O ₂ H ₅ -CH ^ IN
I. NO ₂ 0 ₂ -O-CH ₅ O, 02 CH ₅ O-C-NH-CH O, 002 C ₂ H ₅ -CH ^

100 100

100 100

NO,

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Ti b 1 1 e (plant # nichldig # nd mites)

letranychus test

Active ingredient

Active ingredient concentration in %

Abtötungigrad in% after

H

0.02
0.002

0.02
0.002

100 100

100 80

NO,

O 0.02 CH ₃ PC-NH-ZhN , 0.002 C ₂ H ₅ -CH 1 -N-NU ₂ NO ₂ 0.02 OTT - Λ O — W — OXT // \\ 0.002 C ₂ H ₅ -OHYY-NO ₂
ίο 0
ir, -.

CH ₃ O-C-NH- / ^ Cl 0.02 ^ ^ζ '^ 0.002 0.0002

NO,

Ie A 12 194

- 13 -0098A7 / 1853 100 100

100 80

100 99 40

T from φ 1 It (vegetal ldlgtnd Milbtn)

Tetranychus test

Ie A 12 194 - 14 -

009847/1853

Active ingredient ingredient concentration degree in %

tr »tion in % J \? ^cn

C ₂ H ₅ ^^ CH ₅ OCN V / "^{0> 02 10} °

0.002 30

NO ₂

CH ₃

CH ₃ O-C-NH-C CN 0.02 100

C ₂ H ₅ -CH ^ Ύ ^ γ NO ₂ CH ₃ 0.002 100

NO ₂

O-C-NH-CH ₂ -CH = CH ₂ 0.02 100

NO ₂ 0.002 100

Example B.
Phaedon larvae test.

Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Mixed to produce an appropriate preparation of active ingredients 1 part by weight of active ingredient with the specified amount Solvent containing the specified amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are sprayed to runoff with the preparation of active compound and are populated with mustard beetle larvae (Phaedon cochleariae).

After the specified times, the degree of destruction is determined in #. 100 # means that all beetle larvae have been killed. 0 $> means that none of the beetle larvae have been killed.

Active ingredients, active ingredient concentrations, evaluation times and results are shown in the following table:

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0 0.9 8 A 7/1 853

Table , (plant-damaging insects)

Phaedon Lärven test

Active ingredients

Active ingredient concentration
in %

Degree of destruction in % after 3d

CH

0 C

CH, 0-C-CH = CH-CH, » ■? ι

(known)

CH,
C ₂ H ₅ -CH - ^

NO,

0 κ

O-C-NH-CH-O-CH ₃

-NO,

NO, 0.2
0.02

0.2
0.02

0.2
0.02

100 0

100 95

100 95

fl

C ₀ H ^ -CH
^ 5

NO 0.2
0.02

100 95

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009 847/1853

Active ingredients

it

Tab 1 1 e (plant-damaging insects)

Phaed on-Ierven-T it t

Active ingredient concentration
in 96

Degree of destruction in% after 3 d

CH, OC-MH- <H ₇

^{1 3} * ■ Λ V- /

O ', 2

0.02

0.002

0.2
0.02

100 80 40

100 40

CJH ₃ OCN- / 7-OH ₃ C ₂ H ₅ -CH-

NO, 0.2
0.02

100 70

O-C-NH-CH ₉ -CH = CH ₀

NO, Le A 12 194 0.2
0.02

0.2
0.02

- 17 009847/1853

100 60

100 95

Example 0

Myzus test (contact effect)

Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount Solvent that contains the specified amount of emulsifier and dilute the concentrate with water to the desired concentration * tration.

Cabbage plants (Brassica oleracea), which are heavily infested by the peach leaf (Myzus persicae), sprayed dripping wet.

After the specified times, the degree of destruction is determined in % . 100% means that all aphids have been killed, 0 % means that none of the aphids have been killed.

Active ingredients, active ingredient concentrations, evaluation times and The results are shown in the table below:

Ie A 12 10.4 - 18 -.

009847 / 18-6

Active ingredients

43

Table (plant-damaging insects)

Myzug test active ingredient concentration
in %

Degree of destruction in % after 24 h

. ο

OH, O-C-CH = CH-CH, ι 3 j ^

NOo

NO,

(known)

Il

O-C-NH-CH

C _O H, -C'H

0.2

0.2
0.02

100 95

0.

Il

C ₀ Hc-CH

CH ₃
C ₂ H ₅ -CH

NO

0 0-C-NH-C ₃ H ₇

NO, 0.2

0.2

100

100

CH ₃

0-0-NH-CH ₂ -O-OH ₃

NO, 0.2
0.02

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100 85

Active ingredients

Table (plant-damaging insects)

Myzue test drug concentration
in %

Degree of destruction in % after h

C ₂ H ₅ -CH

CH ₅ O-C-NH-C ₁₄ H ₂₉ CH ^

NO,

C ₂ H ₅ -CH

0 η

0-C-NH

NO

CH-

NO,

O η

ο-σ-

NO

CH ₃

C ₂ H ₅ -CH

OC-NH-G-CN ^N0 2CH,

? ^Η 3
C ₂ H ₅ -CH

NO,

0-0-NH-CH ₀ -GH = CH ₀ ad.

NO, 0.2

0.2

0.2

0.2

0.2

100

100

100

100

Le A 12 194

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example 1

A solution of 48 g of 2-sec-butyl-4,6-dinitrophenol (0.20 mol), 13 g of methyl isocyanate (0.23 mol) and 5! Drops of pyridine in 300 ml Methylene chloride is heated to boiling for 5 hours. After cooling, the solvent is evaporated off in vacuo. The oily The residue crystallizes on stirring with white spirit. After recrystallization from toluene / petroleum ether, 34 g are obtained N-methylcarbamic acid 2-sec-butyl-4,6-dinitrophenyl ester of formula

0 0-C -NH-CH, .-

of pp. 123 - 124 ° C as yellow needles.

In the same manner as above, the following compounds are made obtain:

O-C-NH-R "'·

NO ₂

R "

Pp 82 - 83 ⁰ C

O ₁₄ H ₂₉ pp: 59 ^° C

CH ₂ -O-CH ₃ pp 115-116 ⁰ C

OH ₂ -CH = CH ₂ . Pp. _Σ 105 - 106 ⁰ C

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Pp .: 132-133 ⁰ C pp .: 93-95 ⁰ C oil

Example 2

In a solution of 83 g of chloroformic acid-2-sec-butyl-4,6-dinitrophenyl ester (0.275 mol) in 600 ml of toluene is introduced at 0 - 5 ⁰ C 25 g of dimethylamine (0.55 mol), stirred for 15 minutes at Room temperature, sucks off the dimethylammonium chloride and evaporates the piltrate in a water jet vacuum. The oily residue is dissolved in hot white spirit, the solution filtered and cooled. The lower layer which separates out is separated off and freed from the remaining petroleum ether in a high vacuum. 41 g of N, N-dimethylcarbamic acid 2-sec-butyl-4,6-T dinitrophenyl ester of the formula are obtained

as red oil, n-p 1.5456.

The chlorocarbonic acid-2-sec-butyl-4,6-dinitrophenyl ester used for the reaction is new and can be made in the following ways:

79g of phosgene (0.8 mol) are dissolved at -2O ⁰ C in 200 ml of ether is added dropwise at the same temperature a solution of 48 g of 2-sec-butyl-4,6-dinitrophenol (0.2 mol) in 100 ml of ether and

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then 20 g of triethylamine. It is left for 30 minutes at room temperature, sucks off and evaporates the piltrate. 56 g of the desired product are obtained as an orange-colored oil without further purification is used.

In the same way as indicated in Example 2, the following compounds are obtained:

CH ₂ -GH = OH ₂

CH,

CH,

R " ¹ OH,

-C-CN

CH,

CH ₂ -CH = CH ₂

Cl

-CH

Pp .: 97-98 ^U C

oil

1.5604

n / ⁵ 1.5775

1.5538

n _D ²⁰ 1.5632 n _D ²⁰ 1.5578

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Claims (6)

Claims 'Λ) i2-alkyl-4,6-dinitrophenol derivatives of the formula (D in which R for branched alkyl with 5 - 12 carbon atoms ' stands, R ¹ stands for hydrogen or methyl, R "represents hydrogen, alkyl, haloalkyl or alkenyl stands, R "'for optionally by halogen, cyano or alkoxy substituted alkyl, alkenyl, cycloalkyl, optionally halogen-substituted aralkyl or optionally substituted phenyl. 2) Process for the preparation of 2-alkyl-4,6-dinitrophenol derivatives, characterized in that one \ a) 2-Alkyl-4,6-dinitrophenols of the formula (ID in which
R and R ^{1 have} the meaning given above. with isocyanates of the formula R "'- NCO (III) 1863 in which
R "'has the meaning given above, with the Exception that R " ^{1 must} not stand for cyanoalkyl, optionally reacts in the presence of a solvent, or b) 2-alkyl-4,6-dinitrophenyl chlorocarbonate of formula Il O-C-Cl \ (IV) in which
R and R ^{1 have} the meaning given above, with secondary amines of the formula R "» in which R "and R" ^{1 have} the same meaning as above, with the exception that R "must not stand for hydrogen, optionally reacted in the presence of a solvent. 3) Insecticidal and acaricidal agents, characterized by a content of 2 ~ alkyl-4,6-dinitrophenol derivatives according to Claim.1. 4) A method for combating insects and mites, characterized in that 2-alkyl-4-, 6-dinitrophenol derivatives according to Claim 1 are allowed to act on the insects and acarids or their living space. le λ 12 194 - 25 - 0098 47/1883 5) Process for the preparation of insecticides and acaricidal agents, characterized in that 2-alkyl-4,6-dinitrophenol derivatives according to claim 2 mixed with extenders and / or surface-active agents. 6) Use of 2-alkyl-4,6-dinitrophenol derivatives according to Claim 1 for combating insects and acarids. Le A 12 194. - 26 - 009847/1853