DE19844192A1 - New substituted alkoxycarbonyl compounds - Google Patents

Abstract

Substituted alkoxycarbonyl compounds (I) are new. Substituted alkoxycarbonyl compounds of formula (I) are new. n = 0 or 1; Ar' = an optionally substituted mono- or bicyclic saturated or partially unsaturated carbo- or heterocyclic group; Q = O, S, SO, SO2, NH, N(alkyl) or CH2; R<1> = alkyl or cycloalkyl; R<2> = H or alkyl; Y = NH or N(alkyl); Z' = optionally substituted mono- or bicyclic saturated or partially unsaturated N-bound heterocycle.

Description

The invention relates to new substituted alkoxycarbonyl compounds, processes for their production 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). The effectiveness however, these known compounds are 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 represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or CH ₂ (methylene),
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 bicyclic grouping - also stands for optionally substituted cycloalkylamino or arylamino .

The compounds of general formula (I) according to the invention contain min least an asymmetrically substituted carbon atom and can therefore in ver different enantiomeric (R- and S-configured forms) or diasteromeric Shapes are available. The invention relates to both the different possible individual enantiomeric or stereoisomeric forms of the compounds of the general my formula (I) as well as the mixtures of these stereoisomeric compounds.

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

The invention preferably relates to compounds of the formula (I) in which
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, benzox , 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 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,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C ₁ -C ₄ alkyl) or CH ₂ (methylene),
R ^{1 represents} alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
R ^{2 represents} hydrogen or alkyl having 1 to 4 carbon atoms,
Y represents NH or N (C ₁ -C ₄ alkyl), and
Z for each optionally substituted and bonded via N, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S, S-dioxothiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolynolol, perhydroindolynolynolol , Tetrahydroisoquinolinyl or perhydroisoquinolinyl, or - in the event that n is 1 or Ar is a bicyclic grouping - is also optionally substituted cycloalkylamino having 3 to 6 carbon atoms or arylamino having 6 or 10 carbon atoms, where 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.

The invention relates in particular to compounds of the formula (I) in which
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, benzoxazylyl, thiazole Benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, iso quinolinyl, pyrimidinyl, or the - also optionally substituted below groupings

where A is methylene or dimethylene (ethane-1,2-diyl) 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, methyl thio, 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 represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or CH ₂ (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 represents in each case optionally substituted and is bonded via N pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl, S, S-dioxo-thio morpholinyl, perhydroazepinyl, piperazinyl, indolinyl, iso indolinyl, Perhydroindolinyl, Perhydroisoindolinyl, tetrahydroquinolinyl, Perhydrochinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, or - if 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, methyl thio, 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.

A particularly preferred group are those compounds of the formula (I) in which
Q represents oxygen,
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ^{2 represents} hydrogen or methyl,
Y represents NH, N (methyl), N (ethyl) or N (i-propyl) and
Ar represents the grouping below

wherein
R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, di fluoromethoxy or trifluoromethoxy and
R ^{4 represents} hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
and n and Z have the meaning given above as being particularly preferred.

Another particularly preferred group are those compounds of the formula (I) in which
Q represents sulfur, SO or SO ₂ ,
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ^{2 represents} hydrogen or methyl,
Y represents NH, N (methyl), N (ethyl) or N (i-propyl) and
Ar represents the grouping below

wherein
R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, di fluoromethoxy or trifluoromethoxy and
R ^{4 represents} hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
and n and Z have the meaning given above as being particularly preferred.

Another particularly preferred group are those compounds of the formula (I) in which
Q represents NH or N (methyl),
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ^{2 represents} hydrogen or methyl,
Y represents NH, N (methyl), N (ethyl) or N (i-propyl) and
Ar represents the grouping below

wherein
R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, di fluoromethoxy or trifluoromethoxy and
R ^{4 represents} hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
and n and Z have the meaning given above as being particularly preferred.

Another particularly preferred group are those compounds of the formula (I) in which
Q represents CH ₂ (methylene),
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ^{2 represents} hydrogen or methyl,
Y represents NH, N (methyl), N (ethyl) or N (i-propyl) and
Ar represents the grouping below

wherein
R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, di fluoromethoxy or trifluoromethoxy and
R ^{4 represents} hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
and n and Z have the meaning given above as being particularly preferred.

Another particularly preferred group are those compounds of the formula (I) in which
Q represents oxygen,
R ^{1 represents} methyl, ethyl, n- or i-propyl,
R ^{2 represents} hydrogen or methyl,
Y represents NH, N (methyl), N (ethyl) or N (i-propyl) and
Ar represents one of the groupings below

and n and Z have the meaning given above as being particularly preferred.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

Particularly preferred examples of the compounds of the general My formula (I) 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 stand out in particular through strong and selective herbicidal activity as well as through fungicidal and insecticidal effectiveness.  

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 = NZ (III)
  in which
  Z has the meaning given above,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
  or if you
• (b) chloroformic acid esters of the general formula (IV)
  in which
  Ar, Q, R ¹ and R ^{2 have} the meaning given above,
  with nucleophilic compounds of the general formula (V)
  H- (Y) _n -Z (V)
  in which
  n, Y and Z have the meaning given above,

optionally in the presence of a reaction auxiliary and optionally in 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 reaction sequence 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). In formula (II), Ar, Q, R ¹ and R ² preferably have, or in particular those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as 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 according to known processes can be prepared (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A-5 399 545, cf. the manufacturing examples).

To continue to be used as starting materials in process (a) according to the invention The isocyanates are generally defined by the formula (III). In the formula (III) Z preferably or in particular has the meaning already mentioned above in Zu connection with the description of the compounds of the invention Formula (I) preferably or as particularly preferred for Z was specified.  

The starting materials of the general formula (III) are known organic synthesis 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 are preferred or as particularly preferred for Ar, especially in connection with the description of the compounds of the formula (I) according to the invention, Q, R ¹ and R ² were given.

The starting materials of the general formula (IV) are known and / or can be according to known processes can be prepared (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A-5 399 545, cf. the manufacturing examples).

To continue to be used as starting materials in process (b) according to the invention The nucleophilic compounds are generally defined by the formula (V). In of the formula (V) n, Y and Z preferably or in particular have those interpretations already above in connection with the description of the Invention compounds of formula (I) preferably or as in particular before given for n, Y and Z were given.

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

Reaction aids for processes (a) and (b) are generally those usual inorganic or organic bases or acid acceptors into consideration. These preferably include alkali metal or alkaline earth metal, acetates, amides, -carbonates, -hydrogencarbonate, -hydride, -hydroxide or -alkanolate, such as as 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 -methanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or t-butanolate; also basic organic nitrogen compounds, such as tri methylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-Di methyl 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-me thyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diaza bicyclo [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 the process (b) according to the invention, those which may be used as off nucleophilic compounds of the general formula to be used (V) - used in a corresponding excess - serve as reaction aids.

As a diluent for carrying out processes (a) and (b) Inert organic solvents are particularly suitable. This includes in particular aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra chlorinated carbon; 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 acetic acid methyl ester 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 mono ethyl ether, their mixtures with water or pure water.  

The reaction temperatures can be carried out when carrying out the inventive Processes (a) and (b) can be varied over a wide range. In general one works at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

Processes (a) and (b) according to the invention are generally below normal printing done. However, it is also possible to use the method according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out.

To carry out processes (a) and (b) according to the invention, the off Common materials generally used in approximately equimolar amounts. It is however, it is also possible to use one of the components in a large excess to use. The implementation is generally in a suitable Ver diluent, optionally in the presence of a reaction auxiliary leads and the reaction mixture is generally several hours at which required temperature stirred. The processing is carried out according to usual methods carried out (see the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. 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, Carduippum, Sonuanum , 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, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

However, the use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections to weed beds fighting in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hops plants, on ornamental and sports turf and pastures and for selective weeds fighting in annual crops.  

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocotyledon and dicotyledon weeds in monocotyledons and dicotyledon cultures both pre-emergence and post-emergence.

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

Fungicides in crop protection are used to combat plasmo diophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Bactericidal agents are used in plant protection to combat Pseudomonada ceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae used.

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, for example, Venturia inaequalis; Pyrenophora species, such as, for example, 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, for example, 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 show in particular good effect against mildew (Erisyphe graminis).

The good plant tolerance of the active ingredients in the fight against Concentrations necessary for plant diseases allow treatment of above-ground parts of plants, planting and seeds, and the soil.

The active compounds 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 z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda z. B. Blaniulus guttulatus. From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec. From the order of the Symphyla z. B. Scutigerella immaculata. From the order of the Thysanura z. B. Lepisma saccharina. From the order of the Collembola z. B. Onychiurus armatus. From the order of Orthoptera z. B. 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 z. B. Auricular Forficula. From the order of the Isoptera z. B. Reticulitermes spp. From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp. From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci. From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Pemphigoronumpp padi, 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 z. B. 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., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hof mannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnidana, Homona magnidana. From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthos celides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptino tarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephusus spp., Or spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus sppium, sides., Nipt ., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa. From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp. From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans. From the order of Acarina z. B. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chori Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp. The plant parasitic nematodes include z. B. 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., Tylenchulus spp.

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

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im  impregnated natural and synthetic materials as well as very fine encapsulation in polymers Fabrics.

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

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates  as well as protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite leach and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are 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), Bromo butides, bromofenoxim, bromoxynil, butachlor, butroxydim, butylates, cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlomitrofen, Chlorsulfuron, Chlortoluron, Cin methylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyan  azines, cycloates, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Di ethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphen amide, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethal fluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, eto benzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), Flaniprop (-methyl), flazasulfuron, fluazifop (-P-butyl), flumetsulam, flumi clorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluoro chloridones, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), flurprimidol, hallway tamone, fluthiacet (methyl), fluthiamide, fomesafen, glufosinate (ammonium), Glyphosate (-isopropylammonium), halosafen, haloxyfop (-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, metoxuron, metribuzin, met sulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulf uron, oxazicldmefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pent oxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Pro sulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulfuron (-ethyl), pyraz oxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-so dium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalo fop (-P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfen trazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thi fensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, Tribenuron (methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.  

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.  

Manufacturing examples

example 1

(Method (b))

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

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

Analogous to Example 1 and in accordance with the general description of the inventions Manufacturing processes according to the invention can also be carried out, for example, in the Table 1 listed compounds of formula (I) are prepared.

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

The logP values specified 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 ^b) .

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 using the Retention times through linear interpolation between two consecutive Alkanones).  

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

Starting materials of formula (II)

Example (II-1)

step 1

A mixture of 65 g (0.50 mol) methyl propionylacetate, 34 g (0.50 mol) sodium ethylate and 300 ml 1,4-dioxane is at 30 ° C for 30 minutes Stirred at 90 ° C and then at room temperature (approx. 20 ° C) with stirring with 97 g (0.50 Mol) 3-trifluoromethyl-benzyl chloride added. The reaction mixture is 18 hours which is stirred at 90 ° C to 95 ° C 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 with methylene chloride shaken. The organic phase is separated off, washed with water, with Dried sodium sulfate and filtered. The filtrate is distilled under ver worked up under reduced pressure.

79.4 g (69% of theory) of 3- (3-trifluoromethylphenyl) propanoic acid are obtained ethyl ester with a boiling point of 75 ° C (at 0.7 mbar).  

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 ₄ ), 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 1- (3-trifluoromethyl-phenyl) -pentan-3-ol are obtained Boiling point 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) Ethyloxirane and 0.2 g of lithium hydroxide are 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 solid residue of melting point 53 ° C.  

Analogous to Examples (II-1) and (II-2), for example, those in the Compounds of formula (II) listed in Table 2 below become.

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

Starting materials of formula (IV)

Example (IV-1)

To a mixture of 800 ml toluene, 3 ml N, N-dimethylformamide and 54 g (0.55 Mol) of phosgene becomes a solution of at room temperature (approx. 20 ° C.) with stirring 120 g (0.52 mol)) 1- (3-trifluoromethyl-phenyl) -pentan-3-ol in 600 ml of toluene given dropwise. The reaction mixture is then ge at 60 ° C for 8 hours stirs. The solvent is then carefully removed in a water jet vacuum distilled.

144 g (94% of theory) of chloroformic acid-O- [1-ethyl-3- (3-trifluoro methyl-phenyl) -propyl] ester as an amorphous residue, which without further purification can be used as starting material in process (b) according to the invention.  

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 prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is poured with the active ingredient preparation. You keep the water quantity per unit area expediently constant. The drug concentration in the preparation does not matter, only the application rate of the Active ingredient 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 annihilation.

In this test, for example, the compounds according to Preparation Example 1 are shown and 40 with partially good tolerance to crops, such as. B. barley, strong action against weeds.  

Example B Post emergence test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of Have 5-15 cm so that the desired amounts of active ingredient per area unit can be deployed. The concentration of the spray liquor is chosen so that the desired amounts of active ingredient 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 annihilation.

In this test, for example, the compounds according to the preparation example show 1, 2, 33, 34 and 40 with good tolerance to crops, such as e.g. B. wheat, strong action against weeds.  

Example C Erysiphe test (barley) / resistance induction

Solvent: 48.8 parts by weight of N, N-dimethylformamide
Emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for resistance-inducing effectiveness, young cereals are sprayed plant with the active ingredient preparation in the specified application rate. 4 days after the treatment, the plants are covered with spores of Erysiphe graniinis f. sp. Hordei inoculated. The plants are then grown in a greenhouse at 70% relative humidity and a temperature of 18 ° C.

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

In this test, for example, the compounds according to Preparation Example 8 show 10, 11, 12, 13, 14, 15, 16 and 56 with an application rate of 750 g / ha Efficiency from 80% to 95%.  

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 prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified given amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Seedlings of broad bean (Vicia faba minor), which with the green peach leaf lice (Myzus persicae) are infected in the active ingredient preparation of the Gewün dipped in concentration and placed in a plastic can.

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

In this test, e.g. B. the compounds according to Preparation 21, 26, 29th and 40 at an active ingredient concentration of 0.1% a degree of killing of 90% until 100%.  

Example E Plutella test / artificial feed

Solvent: 100 parts by weight of acetone
Emulsifier: 1900 parts by weight of methanol.

To prepare a suitable preparation of active compound, 1 Ge is mixed important part of the active ingredient with the specified amount of solvent and dilutes the Concentrate with methanol to the desired concentrations.

A specified amount of active ingredient is added to a standardized amount of synthetic feed pipetted preparation of the desired concentration. After the methanol ver is vaporized, a film can lid covered with approx. 100 plutella eggs per cavity put on. The newly hatched larvae migrate to the treated synthetic food.

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

In this test, e.g. B. the compounds according to Preparation Example 22, 23rd and 69 with an active ingredient concentration of 0.1% an efficiency of 95%.

Claims (12)

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 represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or CH ₂ (methylene),
R ^{1 represents} alkyl or cycloalkyl,
R ^{2 represents} hydrogen or alkyl,
Y represents NH or N (alkyl), and
Z represents optionally substituted, monocyclic or bicyclic, saturated or partially unsaturated heterocyclyl bonded via N,
or - if n stands for 1 or Ar stands for a bicyclic grouping - also stands for optionally substituted cycloalkylamino or arylamino. 2. 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 grouping from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl , Thiazolyl, benzthiazolyl, pyrazolyl, pyridinyl, quinolinyl, iso quinolinyl, pyrimidinyl, or the - also optionally substituted below grouping below
where A is halogen-substituted alkanediyl having 1 to 3 carbon atoms, and where the possible substituents are preferably 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,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C ₁ -C ₄ alkyl) or CH ₂ (methylene),
R ^{1 represents} alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,
R ^{2 represents} hydrogen or alkyl having 1 to 4 carbon atoms,
Y represents NH or N (C ₁ -C ₄ alkyl), and
Z for each optionally substituted and bonded via N, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thio morpholinyl, S-oxothiomorpholinyl, S, S-dioxothiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroindolinyl, perhydroindolinyl , Perhydro quinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, or - if n stands for 1 or Ar stands for a bicyl group - also stands for optionally substituted cycloalkylamino with 3 to 6 carbon atoms or arylamino with 6 or 10 carbon atoms, 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 with 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 grouping 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 according to the following groups
where A is 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:
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 represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or CH ₂ (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 pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S, S-dioxothiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoraholynolinolinolynolinolynolinolynolinolynolin, Tetrahydroiso quinolinyl or perhydroisoquinolinyl,
or - in the event that n stands for 1 or Ar stands for a bicyclic grouping - also stands for optionally substituted cyclohexylamino or phenylamino, 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-Bu toxy, 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. 4. 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 ^{4 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 = NZ (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 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 any one of claims 1 to 9 and usual extenders.