DD295519A5 - AKARICIDAL AGENTS - Google Patents

Abstract

The invention relates to acaricidal agents and their use in agriculture and forestry and horticulture. According to the invention, acaricidal agents containing as active ingredients N-arylamino acid 2-ethylhexyl esters of the formula (I) are used. R corresponds to the substituents specified in the description of the invention. Formula (I) {Acaride agent; N-Arylaminosaeure 2-ethylhexyl; Application in horticulture; Agriculture; Forestry}

Description

Field of application of the invention

The present invention relates to akarzidide agents containing as active ingredients N-aryl amino acid 2-ethylhexylester and their application in agriculture and forestry and horticulture.

Characteristic of the known technical solutions It has already become known that the following active substances have pesticidal, in particular acaricidal properties: Phosphoric acid esters and thiophosphoric acid esters, such as: O, S-dimethyl-thiolphosphoric acid ester amide; O, O-dimethyl-S- (N-

methylcarbamoylmethyO-thiolphosphorsäureester; O.o-dimethyl-O-d ^ dibromo-dichlorethyD-organophosphate;

Thiophosphoric acid ò.ó-dimethyl-O-p-nitrophenylesteru.a. Dithiophosphorsäureester, such as. For example, O, O-dimethyl-S- (N-methyl-

carbamoylmethyl) dithiophosphate; Carbamates, such as. For example, 1-naphthyl-N-methyl-carbamate; 2-methyl-2-methylthiopropionaldehyde-O-methylcarbamoyloxime u.a. and various drugs from other classes of drugs, such. B .:

Tricyclohexyltin hydroxide, i.i.i-trichloro ^ bis-fp-chloro-phenyll-ethanol. The compounds mentioned are characterized by a relatively rapid knock-down effect compared with those in the field of land use.

and forestry as well as occurring in horticultural pests from the order Acarina.

However, the said acaricides have the disadvantage that their applicability in practice, in particular in agriculture and

is limited in horticulture for toxicological reasons.

It is also known from the literature that it is widespread in agriculture, forestry and horticulture

resistance in pest populations, especially in populations of harmful mite species. For example, Klunker (Tag.-Ber.Akad. Landw. Wiss.DDR, Bln. [1974] 126, 133-50) and Pilz et al. (Arch. Phytopathol

Pflanzensch. Bln. 14 [1978] 6,383-391) about resistance phenomena in spider mite populations (Tetranychus urticae KOCH)

Dimethoat.Laurens (Bull., Res. Lond. 70 [1980], 1-10) describes resistance to organophosphoric acaricides in bovine ticks (Acari: Ixodidae) and Crystal et. al. (J.Georgia Entomol. Soc. Vol. 19 [4] 1984, 517-523) report widespread malathion, carbaryl and Stirofos resistance in Ornithonyssus sylviarum

CANESTR.et.FANZAGO (bird mites, Acari: Macronyssidae). An increase in the drug expenditure is when using the known acaricides with regard to their relatively high

toxicological concern for the control of such pest populations not possible.

The search for alternative acaricidal agents, which in sufficient warm-blooded toxicity sufficient Fighting success in populations of harmful mites, is therefore an urgent concern. Furthermore, some N-phenyl-alanine esters are known from the literature, which are biologically active as intermediates for the synthesis DL-N-aryl-N-acyl-alanine esters are needed.

(e.g., CH 609,964, GB 1,164,160).

In the literature, however, there is no evidence to date that DL-N-arylamino acid 2-ethylhexylester has an acaricidal activity

respectively.

Object of the invention

The object of the invention is the development of novel acaricidal agents and improved efficacy and reduced toxicity to warm-blooded animals.

Explanation of the essence of the invention

The object of the invention is to develop novel acaricidal agents which have lower toxicity to warm-blooded animals with improved effectiveness.

According to the invention the object is achieved in that acaricidal agents containing as active ingredient a N-arylamino acid 2-ethylhexylesterder general formula (I),

f / ^

-NH-CH-CO-OCH ₂ -CH-C ₄ H _{9 (n}

in which

R is hydrogen, C ₁ ^ un- / branched alkyl or phenyl, is used. The representation of some N-aryl amino acid esters is known from the literature. Several publications have suggested N-aryl amino acid ester e.g. by reaction of arylamines with a-Haloalkylcarbonsäureestern represent. (DE 2,515,091, D.Huy-Diao and A. Lattes, C.R. Acta d.Sci., Paris, Ser. C 264 [23], 1864-1867 (1967]). The new DL-N-arylamino acid-2

ethylhexyl esters of the formula I can be synthesized in an analogous manner.

Preferred compounds of the N-arylamino acid 2-ethylhexyl esters according to formula I are:

CX-NH-CH-CO /

OH ₀ -CH-C ₇₁ Hq (α) ">

Verb no. -R KPCC) 140 1 -H Kpo, 15 138-140 2 -CH ₃ KPO, 3 130 3 -C ₂ H ₅ Kpo, 5 145 4 -C ₃ H, (n) Kpo.i 143 5 -C, H ₇ (i) Kpo, i (Bzn / hexane [1: 1] | 6 -C ₆ H ₆ FP66-7

The new DL-N-arylamino acid 2-ethylhexyl esters of general formula I according to the invention show a surprising

acaricidal effect. Surprisingly, the compounds of the formula I according to the invention are also capable of existing resistance or cross-resistance to organophosphorus acaricides, in particular to those from the group of thio- and dithiophosphoric acid esters in pest populations, but especially in populations of

Pests from the order Acarina, breaking. This is important because a major shortcoming in the permanent or periodic use of acaricides from the Group of phosphoric acid esters in pest populations the rapid population genetic accumulation of resistant Mutants within the gene pool of the treated population. This unwanted and unwanted selection of a Resistance strain inevitably leads to the need to use higher amounts of insecticide to decimate the population,

which seems problematic from a toxicological as well as an economic point of view.

The compounds of the formula I according to the invention offer, due to their acaricidal properties as well as their properties simultaneously

favorable toxicological parameters are a desirable alternative to conventional acaricides.

The compounds of the formula I according to the invention are therefore of considerable use in the fields of agricultural and Forestry and horticulture, as with them opportunities for breaking existing resistance in Pests of pathogens as well as possibilities of a warmblood-friendly control of the mentioned pathogens

result.

The novel acaricidal agents according to the invention may contain the usual auxiliary, dilution, modification or Pesticide conditioning agents for the preparation of preparations in the form of solutions, emulsions, Dispersions, powders, dusts, granules, etc. The amount of active ingredient in the preparations of the invention varies depending on the mode of application

of the preparation and is between about 0.05 to 95Ma .-% of the total preparation. Usually the amount is active

Component between 10 and 50% by mass. The term "active ingredient" as used herein means an N-arylamino acid 2-ethylhexyl ester of general formula I. The novel acaricidal agents can according to the invention, for example, as a wettable powder, as a microcapsule, as dust, as granules,

formulated as a solution, as an emulsifiable concentrate, as an emulsion, as a suspension concentrate or as an aerosol. You can have defined "Release" properties.

The novel acaricidal agents of the invention may also contain other ingredients, e.g. one or more Compounds with pesticidal, in particular herbicidal or fungicidal properties or attractants, eg. B. pheromones or Food ingredients for use as baits or for formulations for traps.

The invention also includes a method for controlling harmful mite species, characterized in that the acaricidal agents according to the invention are used against pests in field crops of agricultural crops as well as in other agricultural areas and in the horticultural sector. The example below illustrates the invention in more detail, but is not intended to limit its scope in any way.

embodiment Effect of compounds of the general formula I on spider mites (Tetranychusurticae KOCH) of a dimethoate-resistant

Tribal:

There are leaf discs of primary leaves of the bush beans each 5 seconds in the preparation (aqueous solution or Emulsion) exchanged and placed on moistened filter paper strips. After the coating has dried, the Leaf discs with 15 female spider mites each. After 3 days of stance at standard conditions, the mortality (%) is compared to an untreated control group

certainly.

Table 1 Mortality values for selected compounds of formula I on dimethoate-resistant spider mites (Tetranychus urtica

COOK):

substance active substance Mortality (%) concentration No. the solution (%) UK - 0 dimethoate 0.5 17.6 2 0.5 83.8 3 0.5 100 4 0.5 100 3 0.1 27.4 3 0.2 64.1 4 0.1 39.2 4 0.2 88.3

Claims (3)

1. Acaricidal agent, characterized in that it contains as active ingredient an N-arylamino acid 2-ethylhexyl ester of the general formula (I) O- NH-CH- CO-OCH ₀ - CH - ₂ - CH - C ₄ H ₉ ( _n ) in which R represents hydrogen, C ₁ ^ ₁ un- / branched alkyl or phenyl, in addition to the customary auxiliaries, diluents, modification or conditioning means of pest control. 2. Acaricidal composition according to claim 1, characterized in that they contain between 10 and 50 wt .-% of a compound of formula (I) in addition to the usual auxiliary, dilution-modifying or conditioning agents of pest control. 3. acaricidal agent according to claim 1 to 2, characterized in that they are used to combat pests from the order Acarina (mites) in agriculture and forestry and horticulture.