DD200709A1 - INSECTICIDES AND ACARICIDE AGENTS - Google Patents

Abstract

The invention relates to novel insecticidal and acaricidal agents. As active ingredient they contain compounds of the general formula in which R = hydrogen or chlorine and n = the numbers 1 or 2. formula

Description

-a- 233 17

733 0K3MI32DIiBi: iA2 31'2'2HSZSLD Bitterfeld, 10.9, 1931

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Insecticides and acaricides ivlittel

Field of application of the invention

The compositions according to the invention are very effective xfianzen protection agents against sucking and picking insects

Characteristic of the known technical solutions

It is known that from the large number of insecticides used in agriculture only a few active substances have good control properties against both sucking and biting insects.

Thus, the Colorado beetle is known only from a few insecticides with economically and toxicologically acceptable effort-

fights with good success.

Purely insecticides from the class of halogenated hydrocarbons and phosphoric acid esters have been used in agriculture for this purpose. Due to increasing signs of resistance, Hückstandsproblemen and toxicological reasons, these insecticides must be replaced by new drugs.

W -W »# V

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As effective insecticides for this application area, it is known that, inter alia, vinylphosphoric acid esters, for example "letrachlorvinphos (IB-PS 3 ^ 02 342), have been found; however, these are often insufficient in their range of effect.

goal of

The aim of the invention is to develop new insecticidal and acaricidal agents which are equally suitable for controlling insecticidal and sucking insects.

Explanation of the Wes.ens of the invention

This object is achieved in accordance with the invention in that insecticides and acaricidal agents, in addition to customary auxiliaries and excipients, as active compounds of the general formula

GGlBr

I!

H. -4-0 VC-OP (OC ₂ H

in the

E = hydrogen or Ghlor and

η = the numbers 1 or 2, included.

The active compounds can generally be prepared by reacting equimolar or excess amounts Trialk3rIph.0sph.it with a semi-aromatic ketone produce t

4, S ^ S / J / V W

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ΟΙ!

α \ / 2 2;> 5

GGlBr

^a n - <o XCO-P (0G.H _r ) _?

8th '

This can be done, for example, according to the following rule;

Preparation of 0,0-diethyl-O- (1- (2,5-clichloropienyl) -2-chloro, lor-2-broavinyl) phosphate ester

To a solution of 0.1 mol (33.2 g) of 2,5-dichloro-2-chloro - tibromoacetopheconone and 50% of benzene are added, while stirring at a temperature of 50 to 50 ° C., 13 g of 2-ethylhexylph. dripped osph.it. After the addition of the -Sriäthylphosphits is heated for a further hour on your boiling water bath, allowed to cool and distilled in vacuo initially the benzene, Athylbromid and excess Triäthylphosphit from and finally under high vacuum, the remaining phosphoric acid ester.

3s, 39 g (39 % of theory) of the desired 0.0-diethyl-O- (1- (2,5-dichlorophenyl-2-chloro-2-bromovinyl) -phosphoric acid ester of refractive index Qtj20 _, 1.5360 were obtained.

In an analogous manner, the following compounds can be prepared;

0,0-diethyl-0- (1 (2,4-dichlorophenyl) -2-chloro-2-bromovinyl) -Ohosphorsäureester

L · Ü sj ι / uw

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O, O-Diethyl-C- (1-C3,4-dichlorophenyl) -2-chloro-2-broynovinyl) -phosphoric acid ester

^π 1

GU -P (OG ₀ H, - ^ nf. ²⁰ : 1.5449

I! ^d ? ^{d D}

0.0-diethylo-O- (1- (4-chloro-chloro-8Q7l) -2-chloro-2-bromovinyl) -phosphoric acid ester.

GCLB

- ^ ο y ~ G - 0 -? (OC ₂ H ₅ ) ₂ Q ^: 1.5391

Ss .V / urde found that the novel active ingredients have a strong insecticidal and acaricidal activity and a greater range of action compared to known 1-Pb.enylvinylph.phosphorsäureestern.

The new phosphoric acid esters have the advantage, because of their broad-spread effect, that very different types of pests can be controlled.

Compared with biting insects, such as the Colorado beetle, the new compounds show good exterminating properties, as well as against various representatives of the order Acarina.

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Ausführungsbe! Games

Example 1: Insecticidal and acaricidal activity of

Compounds of the invention in comparison, to Tetrach.lorvinph.os

The insecticides and acaricidal properties of the agents according to the invention were determined on the housefly (Musca doinestica), the German cockroach (Blattella germanica), the corn beetle (Sitophilus granarius), and also on the head of the JiOhieale (Mamestra brassicae) in the 2 nd stage , Potato beetles (Leptinodarisa decemlineata), black bean aphid (Aphis fabae) and common spider mite (Tetranychus urticae). The reference substance used was cetrachlorovinylphosphine (0,0-dimethyl-O- (1- (2, ', 4-trichloro-9-dyl) -2-chlorovinyl) ph, qsphate).

The experiments on Kusca and Sitophilus were carried out in Fetriscaalen, which were designed with a gutted dog filter (9 cia diameter). The application rate per filter was in each case 1 ml of acetone solution of the indicated concentrations.

Pur the experiments on phytophagous pests, the substances of the invention were used as 20% Smulsionskonzentrate.

The treatment of the host plants was carried out by "dipping or spraying," as host plants, Vicia faba (Maines tr, Aphis), Solanum tuberosum (Leptinotarsa) and Phaseolus vulgar is (Bpilachna, Setranychus) were used.

Exposure time was 13 hours for Musca, Blattella and Sitophilus, 24 hours for Aphis, 48 hours for Mamestra, Spilachna, Leptinotarsa and letranychus.

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In all experiments an untreated control was included.

The percentage mortality is shown; the indication of the "test concentration is in percent by weight". In the i'absllen "mean:

Compound 1: 0, O-diethyl-Q- (1 - (2,5-dichlorophenyl) -2-chloro - - -

bromovinyl) phosphoric acid esters

Compound 2 % 0 _r 0-Diethyl-0- (1- (2,4-dichlorophenyl) -2-chloro-2-

bromovinyl ^ organophosphate

Compound 3; O, O-diethyl-0- (1- (4-chlorophenyl) -2-chloro-2-bromo-

vinyl) phosphoric acid esters

(Table I: Insecticidal and acarial action of the agents according to the invention in comparison with tetrachlorobromohos

connection M ¹ j I / o - 100 Blatell he ma η i a Sitophilus ranarius 100 usca , 001 % ' = 23 S , 1 % ca S- , 1% = 5 1 doinestica , 1 % 55 0 , 01 % = 100 0 , 01 % = 0 O ,1 % 100 0 JI / 0 0 0 , 1 % = 0 2 O , 01 % 6 0 , 1 % 0 0 , 1 % = 3 O , 001 % = 100 0 = 0 0 0 O , 0001 % = 0 Λ C / j I / O , 1% = tetrachloro- O 0 0 0 vinphos O O

in the

connection Mamestra 100 Epilachna = 100 brassicae 88 varivestis 0 1 0.005% = 100 0,0001 % = 100 0,001% = 82 0.00001% = ο 2 0.05% = 96 0.1 % = 90. 0.01 % - 4-3 0.01% = ο 3 0.01 % = 100 0,0001 % = 100 0.005 % = 63 0.00001 % = 56 Detrachlor- 0.05% = 0.01% vinpiios 0.01% = 0.001%

connection Leptinotarsa decemlineata % = 96. Aphis f abae 100 'Ie tr any claus urticae 100 1 0.05 % = 10 0.1 % = 0 0.1 % = 0 0.01 % = 0 0.01% = 0 0.01 % = 0 2 0.05 % = 79 0.1% = 0 0.1% = 0 3 0.05 / 0 currently U 0.1 % = 0 0.1 % = 23 Tetrachlor-vinpiios 0.05 0.1 fo - 0.1 % =

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Example 2: Permanent action of the agents according to the invention

Studies on the long-term effects of the substances are made on plant material at the heads of the 2nd instar lobule. For this purpose were Vicia faba Jflanzen drip containing 0.1 fo active ingredient spray mixture na_ß injected and filled after 2 and 6 months for the duration of 72 hours with the beads.

In all experiments an untreated control was used.

Table Ii: Duration of action of the agents according to the invention against the heads of the soleule in the second instar

Connection '"Efficiency %

after 2 and 6 days

74 84 11

51 O

1 100 2 92 3 63 tetrachlorvinphos 100 Tr h rp ho α. 66

Claims (1)

233176 -. 9 - 2165 Breakthrough aph. Insecticidal and acaricidal agents, characterized in that, in addition to the usual excipients and carriers, they are active substances of the general formula CClBr E ... L o VC-OP (OC-H, -) ,, ¹ J, ^ ^{J C} in the H = hydrogen or chlorine and
D = the numbers 1 or 2 mean contain.