EP1056734A2 - Substituted alxoxycarbonyl compounds - Google Patents

Abstract

The invention relates to novel substituted alkoxycarbonyl compounds of formula (I), wherein n stands for 0 or 1; Ar stands for an optionally substituted monocyclic or bicyclic saturated or optionally partially- unsaturated carbocyclic or heterocyclic group; Q represents O (oxygen), S (sulfur), SO, SO2, NH, N(Alkyl) or CH2 (methylene); R<1> stands for alkyl or cycloalkyl; R<2> stands for hydrogen or alkyl; Y stands for NH or N(alkyl) and Z stands for optionally substituted monocyclic or bicyclic, saturated or partially unsaturated heterocyclyl bonded by N or it also stands for optionally substituted cycloalkylamino or arylamino in case n stands for 1 and Ar stands for a bicyclic group. The invention also relates to the production of said compounds and to their use as agents in the treatment of plants, more particularly as a herbicide, fungicide and insecticide.

Description

Substituted alkoxycarbonyl compounds

The invention relates to new substituted alkoxycarbonyl compounds, processes for their preparation and their use as plant treatment agents, in particular as herbicides, fungicides and insecticides.

It is known that certain substituted N-aryl-O-aryloxyalkyl-carbamates have herbicidal properties (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A- 5 399 545 / WO-A-9410132, WO-A-9616941). However, the effectiveness of these known compounds is not satisfactory in all respects.

The new substituted alkoxycarbonyl compounds of the general formula (I) have now been found

in which

n represents the numbers 0 or 1,

Ar represents an optionally substituted, monocyclic or bicyclic, saturated or - optionally partially - unsaturated, carbocyclic or heterocyclylic group,

Q for O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or CH ₂

(Methylene) stands,

R ^{1 represents} alkyl or cycloalkyl, R ^{2 represents} hydrogen or alkyl,

Y represents NH or N (alkyl), and

Z stands for optionally substituted, monocyclic or bicylic, saturated or partially unsaturated heterocyclyl bonded via N, or - if n stands for 1 or Ar stands for a bicyl group - also stands for optionally substituted cycloalkylamino or arylamino.

The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in various enantiomeric (R- and S-configured forms) or diasteromeric forms. The invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these stereoisomeric compounds.

In the definitions, the hydrocarbon chains, such as alkyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.

Ar preferably represents an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclic group from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl,

Thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - also optionally substituted below grouping

where A is alkanediyl having 1 to 3 carbon atoms which is optionally substituted by halogen, and the substituents which are possible in each case are preferably selected from the following list:

Cyano, nitro, halogen, each optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 6 carbon atoms;

Q preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C, -C ₄ -

Alkyl) or CH ₂ (methylene);

R ¹ preferably represents alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms;

R ² preferably represents hydrogen or alkyl having 1 to 4 carbon atoms;

Y is preferably NH or N (C i -C i-alkyl);

Z preferably represents in each case optionally substituted and bound via N, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S, S-dioxothiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydro - hydroisoindolinyl, tetrahydroquinolinyl, perhydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, or - if n is 1 or Ar is a bicyl group - also optionally substituted cycloalkylamino having 3 to 6 carbon atoms or arylamino having 6 or 10 carbon atoms , where the possible substituents are preferably selected from the following list:

Cyano, nitro, halogen, each optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 6 carbon atoms;

particularly preferably represents an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclic group from the series cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl,

Thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - also optionally substituted below groupings

where A stands for methylene or dimethylene (ethane-1,2-diyl) which is optionally substituted by fluorine and / or chlorine, and where the possible substituents are preferably selected from the following list:

Cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl; Q particularly preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or CH ₂ (methylene);

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, or cyclopropyl;

R ² particularly preferably represents hydrogen or methyl;

Y particularly preferably represents NH, N (methyl), N (ethyl) or N (i-propyl);

Z particularly preferably represents in each case optionally substituted and above

N-linked pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl, S, S-dioxo-thiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, tetra-hydrohydroquinololinol, tetra-hydroquinroololinol isol or - in the event that n stands for 1 or Ar stands for a bicyclic grouping - also for optionally substituted cyclohexylamino or phenylamino, the possible substituents in each case preferably being selected from the following list:

Cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl;

Q particularly preferably represents oxygen;

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl; Ar particularly preferably represents the grouping below

wherein

R3 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy and

R4 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl;

Q furthermore very particularly preferably represents CH ₂ (methylene);

Ar still very particularly preferably represents one of the groupings below

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Particularly preferred examples of the compounds of the general formula (I) according to the invention are listed in the groups below.

Group 1

n stands for the numbers 0 or 1, Y for NH, N (methyl), N (ethyl) or N (i-propyl), and Z has the meanings listed below:

Group 2

n, Y and Z have the meanings given above in Group 1.

Group 3

n, Y and Z have the meanings given above in Group 1.

Group 4

n, Y and Z have the meanings given above in Group 1.

Group 5

n, Y and Z have the meanings given above in Group 1. Group 6

n, Y and Z have the meanings given above in Group 1.

Group 7

n, Y and Z have the meanings given above in Group 1.

Group 8

n, Y and Z have the meanings given above in Group 1.

Group 9

n, Y and Z have the meanings given above in Group 1. Group 10

n, Y and Z have the meanings given above in Group 1.

Group 11

n, Y and Z have the meanings given above in Group 1.

Group 12

n, Y and Z have the meanings given above in Group 1.

Group 13

n, Y and Z have the meanings given above in Group 1. Group 14

n, Y and Z have the meanings given above in Group 1.

Group 15

n, Y and Z have the meanings given above in Group 1.

Group 16

n, Y and Z have the meanings given above in Group 1.

Group 17

n, Y and Z have the meanings given above in Group 1. Group 18

n, Y and Z have the meanings given above in Group 1.

Group 19

n, Y and Z have the meanings given above in Group 1.

Group 20

n, Y and Z have the meanings given above in Group 1.

Group 21

n, Y and Z have the meanings given above in Group 1.

The new substituted alkoxycarbonyl compounds of the general formula (I) have interesting biological properties; they are characterized in particular by strong and selective herbicidal activity and by fungicidal and insecticidal activity. The new substituted alkoxycarbonyl compounds of the general formula (I) are obtained if

(a) substituted alkanols of the general formula (II)

in which

Ar, Q, R ¹ and R ^{2 have} the meaning given above,

with isocyanates of the general formula (III)

O = C = N-Z (III)

in which

Z has the meaning given above,

optionally in the presence of a reaction auxiliary and optionally in

In the presence of a diluent,

or if you

(b) chloroformic acid esters of the general formula (IV) in which

Ar, Q, R and R ^"have the meaning given above,

with nucleophilic compounds of the general formula (V)

H-OOn-Z (V)

in which

n, Y and Z have the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

If, for example, 1- (3,4-difluoromethylenedioxy-phenylthiomethyl) propanol and 2-methyl-benzyl isocyanate are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, chloroformic acid [1- (3-bromo-phenoxymethyl) propyl] ester and piperidine are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the substituted alkanols to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). Ar, Q, R ¹ and R ^{2 in} formula (II) preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for Ar, Q, R ¹ and R ^{2 were} given.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,194,661, US Pat. A-5 399 545, see the production examples).

Formula (III) provides a general definition of the isocyanates which are further to be used as starting materials in process (a) according to the invention. In the formula (III), Z preferably has the meaning which has already been given as preferred or particularly preferred for Z in connection with the description of the compounds of the formula (I) according to the invention. The starting materials of the general formula (III) are known organic synthetic chemicals.

Formula (IV) provides a general definition of the chloroformic acid esters to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I). In formula (IV), Ar, Q, R ¹ and R ² preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, as being particularly preferred or very particularly preferred for Ar, Q, R ¹ and R ^{2 were} given.

The starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,194,661, US Pat. A-5 399 545, see the production examples).

Formula (V) provides a general definition of the nucleophilic compounds to be used further as starting materials in process (b) according to the invention. In formula (V), n, Y and Z preferably have those meanings which have already been given above as preferred, particularly preferred or very particularly preferred for n, Y and Z in connection with the description of the compounds of the formula (I) according to the invention were.

The starting materials of the general formula (V) are known organic synthetic chemicals.

The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, Potassium or

Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or Calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine,

N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4 -Dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1, 4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or

1,8-diazabicyclo [5,4,0] -undec-7-ene (DBU).

In process (b) according to the invention, the nucleophilic compounds of the general formula (V) to be used as starting materials, if used in a corresponding excess, can also serve as reaction auxiliaries.

Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene,

Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide,

N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out processes (a) and (b) according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a large excess. The reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,

Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus,

Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus,

Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena,

Seeale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. The compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut,

Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants are used on ornamental and sports turf and pasture land and for selective weed control in annual crops. The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence method.

The active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms. The active ingredients are suitable for use as fungicides.

Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes,

Basidiomycetes, Deuteromycetes.

Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae; Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia

Species such as Venturia inaequalis; Pyrenophora species, such as wise Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia-

Species such as Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The active compounds of the general formula (I) according to the invention in particular show good activity against mildew (Erisyphe graminis).

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active ingredients are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec. From the order of the Symphyla e.g. Scutigerella immaculata. From the order of the Thysanura, for example Lepisma saccharina. From the order of the Collembola, for example Onychiurus armatus. From the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera e.g. Forficula auricularia. From the order of the Isoptera e.g. Reticulitermes spp .. From the order of the Anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp. From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci. From the order of the

Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Pemphigylloxumum. Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp. From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella,

Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplellaocapsi. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnidana, Homona magnidana. From the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Acanthosceles obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica sppo, Psyllphala, chrys Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderus spp.,. Anthenhrenus spp.,. Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp

Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula palosa. From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the order of the Arachnida e.g. Scoφio maurus, Latrodectus mactans. From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp .. The plant parasitic nematodes include, for example Pratylenchus spp., Radopholus spp.,

Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Tylenchus spp., Helicotylenchus spp., Rotylenchus spp ..

The compounds of the general formula (I) according to the invention are very suitable for controlling plant-damaging insects, such as e.g. Cabbage cockroaches (Plutella spp.) And aphids (Mycus spp.).

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. also organic

Solvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable

Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural

Rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: eg broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Suitable emulsifying and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates as well as protein hydrolyzates; Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight

Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate , Bensulfuron (-methyl), bentazone,

Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidaz, Chloronben, Chloramben, Chloramben, Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cin- methylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop,

Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyan- azine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop (-methyl), diclosulam, diethyl ( -ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, flurocarbin, ethalc, esulfuron ), Ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl,

-sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Fluφrimidol, Flur- tamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Halosafen -ethoxyethyl), haloxy-fop (-P-methyl), hexazinones, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon,

Isouron, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metibonethyl, Metoxuron, Metoxuron, Metoxuron Molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxoxetulfurone, phenoxamphosphone, phenophone (proxy), pentoxazulfuron ), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Pro-sulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyraz-oxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-m Pyrithiobac (- sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosates, Sul fosulfuron, tebutam, tebuthiuron, Terbuthylazine, Terbutryn, thenylchlor, Thiafluamide, thiazopyr, thidiazimin, thionyl fensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, Triasulf- uron, tribenuron (-methyl), triclopyr, Tridiphane, trifluralin and Triflusulfuron. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

(Method (b))

4.5 g (15 mmol) of chloroformic acid [3-trifluoromethyl-phenoxymethyl) propyl] ester are added with stirring to a mixture of 3.1 g (30 mmol) of N-amino-moleholin and 80 ml of toluene. The reaction mixture is stirred for 5 hours at room temperature (approx. 20 ° C.), then washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

4.8 g (88% of theory) of N- (4-Mθφholinyl) -O- [3-trifluoromethyl-phen-oxymethyl) propyl] urethane are obtained as a solid residue of melting point 98 ° C.

Analogously to Example 1 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a ).

(b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^D ). The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

Starting materials of formula (II):

Example (II- 1)

step 1

A mixture of 65 g (0.50 mol) of propionylacetic acid methyl ester, 34 g (0.50 mol) of sodium ethylate and 300 ml of 1,4-dioxane is at 30 ° C for 30 minutes

Stirred at 90 ° C. and then 97 g (0.50 mol) of 3-trifluoromethylbenzyl chloride were added at room temperature (about 20 ° C.) while stirring. The reaction mixture is stirred at 90 ° C. to 95 ° C. for 18 hours and then concentrated in a water jet vacuum. The residue is stirred in 400 ml of 20% sodium hydroxide solution for 4 hours at 90 ° C., then diluted to about twice the volume with water and shaken with methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is worked up by distillation under reduced pressure.

79.4 g (69% of theory) of ethyl 3- (3-trifluoromethyl-phenyl) propanoate with a boiling point of 75 ° C. (at 0.7 mbar) are obtained. Level 2

23 g (0.10 mol) of 3- (3-trifluoromethyl-phenyl) propanoic acid ethyl ester at room temperature (approx. 20 ° C.) with stirring to a mixture of 6 g of sodium boranate (60% in paraffin, 0.20 Mol NaBH-i), 100 ml of tetrahydrofuran and 10 ml of water are added and the reaction mixture is stirred at room temperature for 18 hours. The mixture is then diluted to about three times the volume with water, shaken with methylene chloride, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is worked up by distillation under reduced pressure.

18.2 g (78% of theory) of l- (3-trifluoromethyl-phenyl) -pentan-3-ol are obtained from the boiling point of 78 ° C. to 80 ° C. (at 0.6 mbar).

Example (II-2)

A mixture of 10 g (43 mmol) of 3,5-bis-trifluoromethylphenol, 5 g (70 mmol) of ethyloxirane and 0.2 g of lithium hydroxide is heated under reflux for 5 hours. Then the volatile components are carefully distilled off in a water jet vacuum.

12 g (92% of theory) of 1- (3,5-bis-trifluoromethyl-phenyl) -butan-2-ol are obtained as a solid residue with a melting point of 53 ° C. Analogously to Examples (II-1) and (II-2), for example the compounds of the formula (II) listed in Table 2 below can also be prepared.

Table 2: Examples of the compounds of the formula (II)

Starting materials of formula (IV):

Example (IV- 1)

A solution of 120 g (0.52 mol) is added to a mixture of 800 ml of toluene, 3 ml of N, N-dimethylformamide and 54 g (0.55 mol) of phosgene at room temperature (approx. 20 ° C.) with stirring. ) 1- (3-Trifluoromethyl-phenyl) -pentan-3-ol in 600 ml of toluene added dropwise. The reaction mixture is then stirred at 60 ° C. for 8 hours. The solvent is then carefully distilled off in a water jet vacuum.

144 g (94% of theory) of chloroformic acid O- [l-ethyl-3- (3-trifluoromethylphenyl) propyl] ester are obtained as an amorphous residue which, without further purification, is the starting material in the process according to the invention (b ) can be used.

Examples of use:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Examples 1 and 40, with good tolerance to cultivated plants, such as barley, show strong activity against weeds. Example B

Post emergence test

Solvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, the compounds according to Preparation Examples 1, 2, 33, 34 and 40, for example, show strong activity against weeds, in some cases with good tolerance to cult pot plants, such as, for example, wheat. Example C

Erysiphe test (barley) / resistance induction

Solvent: 48.8 parts by weight of N, N-dimethylformarnide emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for resistance-inducing activity, young cereal plants are sprayed with the active compound preparation in the stated application rate. 4 days after the treatment, the plants are spotted with Erysiphe graminis f. sp. Hordei inoculated. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 18 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds according to Preparation Examples 8, 10, 11, 12, 13, 14, 15, 16 and 56 show an efficiency of 80% to 95% at a rate of 750 g / ha.

Example D

Myzus test

Solvent: 6 parts by weight of dimethylformamide

67 parts by weight of methanol emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Field bean seedlings (Vicia faba minor), which are infested with the green peach aphid (Myzus persicae), are immersed in the active compound preparation of the desired concentration and placed in a plastic can.

After the desired time, the kill is determined in percent. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the compounds according to Preparation Examples 21, 26, 29 and 40 show a degree of destruction of 90%> to 100% at an active ingredient concentration of 0.1%.

Example E Plutella test / artificial feed

Solvent: 100 parts by weight of acetone emulsifier: 1900 parts by weight of methanol

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with methanol to the desired concentrations.

A specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, a film can lid with about 100 plutella eggs is placed on each cavity. The newly hatched larvae migrate to the treated synthetic food.

After the desired time, the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, e.g. the compounds according to Preparation Examples 22, 23 and 69 have an efficiency of 95% at an active ingredient concentration of 0.1%.

Claims

claims

1. Substituted alkoxycarbonyl compounds of the general formula (I),

in which

n represents the numbers 0 or 1,

Ar represents an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclylic grouping,

Q for O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or CH ₂

(Methylene) stands,

R ^{1 represents} alkyl or cycloalkyl,

R ^{2 represents} hydrogen or alkyl,

Y represents NH or N (alkyl), and

Z for in each case optionally substituted, monocyclic or bicyclic, saturated or partially unsaturated, bound via N

Heterocyclyl stands, or - if n is 1 or Ar is a bicyclic grouping - is also optionally substituted cycloalkylamino or arylamino.

Substituted alkoxycarbonyl compounds according to claim 1, characterized in that

n represents the numbers 0 or 1,

Ar for an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclylic group from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, Benzoxazolyl, thiazolyl, benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - also optionally substituted below grouping below

where A is halogen-substituted alkanediyl having 1 to 3 carbon atoms, and the respective possible substituents are preferably selected from the following list: cyano, nitro, halogen, each optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl , Alkylcarbonyl, alkoxycarbonyl each having up to 6 carbon atoms, Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C, -C ₄ alkyl) or CH ₂ (methylene),

R ¹ for alkyl with 1 to 6 carbon atoms or for cycloalkyl with 3 to

6 carbon atoms,

R ^{2 represents} hydrogen or alkyl having 1 to 4 carbon atoms,

Y represents NH or N (C \ -C ₄ alkyl), and

Z for each optionally substituted and bound via N

Aziridinyl, Azetidinyl, Pyrrolidinyl, Piperidinyl, Morpholinyl, Thi-morpholinyl, S-Oxo-thiomorpholinyl, S, S-Dioxo-thiomoφholinyl, Perhydroazepinyl, Piperazinyl, Indolinyl, Isoindolinyl, Perhydro-indolinyl, Perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolinyl, perhydroisoindolynol Perhydroisoquinolinyl, or - if n stands for 1 or Ar stands for a bicyclic grouping - also stands for optionally substituted cycloalkylamino with 3 to 6 carbon atoms or arylamino with 6 or 10 carbon atoms, with the respective possible substituents preferably are selected from the following list: cyano, nitro, halogen, in each case optionally substituted by halogen alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 6 carbon atoms.

3. Substituted alkoxycarbonyl compounds according to claim 1, characterized in that n represents the numbers 0 or 1,

Ar for an optionally substituted, monocyclic or bicyclic, saturated or — optionally partially — unsaturated, carbocyclic or heterocyclylic group from the series

Cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - also optionally substituted following groups

where A is methylene or dimethylene (ethane-1, 2-diyl) which is optionally substituted by fluorine and or chlorine, and the possible substituents are preferably selected from the following list:

Cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-

Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or CH (methylene),

R ^{1 represents} methyl, ethyl, n- or i-propyl, or cyclopropyl,

R ^{2 represents} hydrogen or methyl,

Y represents NH, N (methyl), N (ethyl) or N (i-propyl), and

Z for each optionally substituted and bound via N

Pyrrolidinyl, Piperidinyl, Moφholinyl, Thiomoφholinyl, S-Oxo-thio-moφholinyl, S, S-Dioxo-thiomoφholinyl, Perhydroazepinyl, Piperazinyl, Indolinyl, Isoindolinyl, Perhydroindolinyl, Perhydroiso- indolinyl, Tetrahydroquinolinolinolhydroquinololinolinolhydroquinololinolhydroquinololinolinol or or - in the event that n stands for 1 or Ar stands for a bicyclic grouping - also stands for optionally substituted cyclohexylamino or phenylamino, the possible substituents in each case preferably being selected from the following list:

Cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i- Propylsulfinyl,

Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.

. Substituted alkoxycarbonyl compounds according to claim 3, characterized in that

Ar represents the grouping below

wherein

R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy and

R ^ represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, and

R ^{1 represents} methyl, ethyl, n- or i-propyl.

5. Substituted alkoxycarbonyl compounds according to claim 4, characterized in that

Q stands for oxygen.

6. Substituted alkoxycarbonyl compounds according to claim 4, characterized in that

Q represents sulfur, SO or SO ₂ .

7. Substituted alkoxycarbonyl compounds according to claim 4, characterized in that Q represents NH or N (methyl).

8. Substituted alkoxycarbonyl compounds according to claim 4, characterized in that

Q represents CH ₂ (methylene).

9. Substituted alkoxycarbonyl compounds according to claim 3, characterized in that

Ar represents one of the groupings below

Q represents oxygen,

R ^{1 represents} methyl, ethyl, n- or i-propyl.

10. A process for the preparation of substituted alkoxycarbonyl compounds according to any one of claims 1 to 9, characterized in that

(a) substituted alkanols of the general formula (II)

in which

Ar, Q, R ¹ and R ^{2 have} the meaning given in one of claims 1 to 9,

with isocyanates of the general formula (III)

O = C = N-Z (III)

in which

Z has the meaning given in one of claims 1 to 9,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or that one

(b) chloroformic acid esters of the general formula (IV)

in which

Ar, Q, R ¹ and R ^{2 have} the meaning given in one of claims 1 to 9,

with nucleophilic compounds of the general formula (V) H- (Y) _n -Z (V)

in which

n, Y and Z have the meaning given in one of claims 1 to 9,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

11. Use of at least one substituted alkoxycarbonyl compound according to any one of claims 1 to 9 as a herbicide, fungicide and / or insecticide.

12. Plant protection products, characterized by the content of at least one substituted alkoxycarbonyl compound according to one of claims 1 to 9 and conventional extenders.