CA2321460A1

CA2321460A1 - Substituted alxoxycarbonyl compounds

Info

Publication number: CA2321460A1
Application number: CA002321460A
Authority: CA
Inventors: Hans-Jochem Riebel; Johannes Rudolf Jansen; Stefan Lehr; Peter Heitkamper; Joachim Kluth; Markus Dollinger; Mark Wilhelm Drewes; Ingo Wetcholowsy; Randy Allen Myers; Gerd Hanssler; Karl-Heinz Kuck; Ulrike Wachendorff-Neumann
Original assignee: Individual
Current assignee: Bayer AG
Priority date: 1998-02-20
Filing date: 1999-02-13
Publication date: 1999-08-26
Also published as: BR9908098A; JP2002504482A; WO1999042457A3; AU2725599A; WO1999042457A2; EP1056734A2; CN1298399A

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); R1 stands for alkyl or cycloalkyl; R2 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

Le A 32 881-Foreien Countries ICri/by/NT
V
- -Substituted alkoxycarbonyl compounds The invention relates to novel substituted alkoxycarbonyl compounds, to processes for their preparation and to their use as crop treatment agents, in particular as herbicides, fungicides and insecticides.
It is known that certain substituted O-aryloxyalkyl N-aryl-carbamates have herbicidal properties (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A-5 399 545IW0-A-9410132, WO-A-9616941). However, the activityof these known compounds is not entirely satisfactory.
This invention, accordingly, provides the novel substituted alkoxycarbonyl compounds of the general formula (I) Ar R' O
Z
~~~Y)n in which n represents the numbers 0 or 1, Ar represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbocyclic or heterocyclic grouping, Q represents O (oxygen), S (sulphur), SO, S02, NH, N(alkyl) or CH2 (methylene), R' represents alkyl or cycloalkyl, Le A 32 881-Foreign Countries R2 represents hydrogen or alkyl, Y represents NH or N(alkyl), and Z represents in each case optionally substituted, monocyclic or bicyclic, saturated or partially unsaturated heterocyclyl which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case 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 be present in various enantiomeric (R- and S-configured forms) or diastereomeric 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 their definitions, the hydrocarbon chains, such as alkyl, are in each case straight-chain or branched - including in combination with heteroatoms, such as in alkoxy.
Ar preferably represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbocyclic or heterocyclic grouping from the group consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - likewise optionally substituted grouping below O
O

Le A 32 881-Forei;en Countries where A represents optionally halogen-substituted alkanediyl having 1 to 3 carbon atoms, where the substituents which are possible in each case are preferably selected from the list below:
cyano, vitro, halogen, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxy-carbonyl having in each case up to 6 carbon atoms;
Q preferably represents O (oxygen), S (sulphur), SO, S02, NH, N(C1-C4-alkyl) or CH2 (methylene);
R' preferably represents alkyl having 1 to 6 carbon atoms or represents cyclo-alkyl having 3 to 6 carbon atoms;
R2 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms;
Y preferably represents NH or N(C 1-C4-alkyl); and Z preferably represents in each case optionally substituted aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpho-linyl, S,S-dioxo-thiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, tetrahydroquinolinyl, perhydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, each of which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case optionally substituted cycloalkylamino having 3 to 6 carbon atoms or arylamino having 6 or 10 carbon atoms, where the substituents which are possible in each case are preferably selected from the list below:
cyano, vitro, halogen, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxy-carbonyl having in each case up to 6 carbon atoms;

i Le A 32 881-Forei,~n Countries i Ar particularly preferably represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbocyclic or heterocyclic grouping from the group consisting of cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - likewise optionally substituted groupings below O \ O \
/ A I
O O /
where A represents in each case optionally fluorine- and/or chlorine-substituted methylene or dimethylene (ethane-1,2-diyl), and where the substituents which are possible in each case are preferably selected from the list below:
cyano, nitro, fluorine, chlorine, bromine, in each case optionally fluorine-and/or chlorine-substituted 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, methylsulphinyl, ethylsulphinyl, n-or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propyl-sulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxy-carbonyl, n- or i-propoxycarbonyl;
Q particularly preferably represents O (oxygen), S (sulphur), SO, S02, NH, N(methyl) or CH2 (methylene);
R' particularly preferably represents methyl, ethyl, n- or i-propyl, or represents cyclopropyl;

I
Le A 32 881-Forei,en Countries R2 particularly preferably represents hydrogen or methyl;
Y particularly preferably represents NH, N(methyl), N(ethyl) or N(i-propyl);
and Z particularly preferably represents in each case optionally substituted pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpho linyl, S,S-dioxo-thiomorpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, tetrahydroquinolinyl, perhydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, each of which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case optionally substituted cyclohexylamino or phenylamino, where the substiutents which are possible in each case are preferably selected from the list below:
cyano, nitro, fluorine, chlorine, bromine, in each case optionally fluorine-and/or chlorine-substituted 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, methylsulphinyl, ethylsulphinyl, n-or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propyl-sulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxy-carbonyl, n- or i-propoxycarbonyl;
Q particularly preferably represents oxygen;
R' particularly preferably represents methyl, ethyl, n- or i-propyl;
Ar particularly preferably represents the grouping below Ra I
Le A 32 881-Foreign Countries r in which 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 CH2 (methylene);
Ar furthermore very particularly preferably represents one of the groupings below O ( ~ F O I ~ F O ~ F O
F' \ FI \ / F I F I
O ~ O F O ~ F O
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings given above as being preferred.
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings given above as being particularly preferred.

c Le A 32 881-Foreign Countries Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings given above as being very 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 p~O~~YjnZ
n represents the numbers 0 or l, Y represents NH, N(methyl), N(ethyl) or N(i-propyl), and Z has the meanings listed below:

Le A 32 881-Forei~2n Countries _g-\ \N \N \N CHs \N
N

\N \N \N \N \N
H CI v H3C CH3 \N ~ \N~CH3 \N \N \N~
~ I S ~O
O ~S ~Sv~ ~ ~n \N~ \N~ \N~ \N~ \N~
~N~H ~N~ ~N~C H ~N~C H -n ~N~C H -i / I \ I / I \
\N ~ \N \N \N ~ N
HsC CH CHs / /
\N \ \N \N \ \N
H C CH

\N I \ \N \N I \ \N

Le A 32 881-Foreien Countries Group 2 2Hs O
O O~~Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 3 F

/

\~ Z
O~O~~Y)r, n, Y and Z have the meanings given above in Group 1.
Grou 4 F

/

O~O~~Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 5 O~O~~Y)nZ
n, Y and Z have the meanings given above in Group 1.

Le A 32 881-Foreign Countries Group 6 FsC \
I
F ~ CZHs p~Q ~Y~ Z
n n, Y and Z have the meanings given above in Group 1.
S Group 7 F' , I \
FXO ~ CH3 O
p~Q~~Y~nZ
n, Y and Z have the meanings given above in Group 1.
Group 8 F~ I \
F O ~ C2H5 O
Q~Q~~Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 9 \ OCF3 I~

O~p~~Y>nZ
n, Y and Z have the meanings given above in Group 1.

Le A 32 881-Foreign Countries Group 10 CzHs O
O O (~')~Z
n, Y and Z have the meanings given above in Group 1.
Groin 11 F

O O (Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 12 F

O~O~~YjnZ
n, Y and Z have the meanings given above in Group 1.
Group 13 ~ Z
0I '(Y)n 1 S n, Y and Z have the meanings given above in Group 1.

L,e A 32 881-Foreign Countries Group 14 / C2Hs O
O' '(Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 15 O (Y)nZ
n, Y and Z have the meanings given above in Group 1.
Groin 16 ~ CF3 2H5~
/~ Z
(Y)n 1~
n, Y and Z have the meanings given above in Group 1.
Group 17 /
O (Y)nZ

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

Le A 32 881-Foreign Countries Group 18 S

O (Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 19 S /
CH
O (Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 20 S

O~(Y)nZ
n, Y and Z have the meanings given above in Group 1.
Group 21 S
CzHs O
O~(YjnZ
n, Y and Z have the meanings given above in Group 1.
The novel substituted alkoxycarbonyl compounds of the general formula (I) have important biological properties; in particular, they have strong and selective herbicidal activity and fungicidal and insecticidal activity.

i Le A 32 881-Foreign Countries The novel substituted alkoxycarbonyl compounds of the general formula (I) are obtained when (a) substituted alkanols of the general formula (II) Ar R' (II) ~OH

in which Ar, Q, R' and R2 are as defined above, are reacted with isocyanates of the general formula (III) O=C=N-Z (III) in which Z is as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or when (b) chloroformic esters of the general formula (IV) Ar R' O
Q ~ (IV) ~O CI

Le A 32 881-Forei , Countries in which Ar, Q, Rl and R2 are as defined above, are reacted with nucleophilic compounds of the general formula (V) H-(Y)n-Z
in which n, Y and Z are as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
Using, for example, 1-(3,4-difluoromethylenedioxy-phenylthiomethyl)-propanol and 2-methyl-benzyl isocyanate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme:

O ~ S~O + OCN
F~( F~ ~ / /
C2H5~ CHa ---~ F O ~ S v _O N
F_ O ~ / H ~ /
Using, for example, 1-(3-bromo-phenoxymethyl)propyl chloroformate and piperidine as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme:

Le A 32 881-Foreign Countries CzHs~ H
~N
Br ~ ~~~ CI
/
CH
Br ~ O~O N
- HCI
The formula (II) provides a general definition of the substituted alkanols to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I). In the formula (II), Ar, Q, R' and R2 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 preferred, particularly preferred or very particularly preferred for Ar, Q, RI
and R2.
The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A-5 399 545, cf. the Preparation Examples).
The formula (Ili) provides a general definition of the isocyanates to be used further as starting materials in the process (a) according to the invention. In the formula (11T), Z
preferably has that meaning which has already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or as being particularly preferred for Z.
The starting materials of the general formula (111) are known organic chemicals for synthesis.
The formula (IV) provides a general definition of the chloroformic esters to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (1]. In the formula (IV), Ar, Q, R' and R2 preferably have Le A 32 881-Foreign Countries 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 preferred, particularly preferred or very particularly preferred for Ar, Q, R' and R2.
The starting materials of the general formula (IV) are known and/or can be prepared by processes known per se (cf. US-A-5 099 059, US-A-5 152 827, US-A-5 194 661, US-A-5 399 545, cf. the Preparation Examples).
The formula (V) provides a general definition of the nucleophilic compounds to be used further as starting materials in the process (b) according to the invention. In the formula (V), n, Y and Z 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 preferred, particularly preferred or very particularly preferred for n, Y and Z.
The starting materials of the general formula (V) are known organic chemicals for synthesis.
Suitable reaction auxiliaries for the processes (a) and (b) are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore, also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-Le A 32 881-Foreign Countries 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 the process (b) according to the invention, the nucteophilic compounds of the general formula (V) to be used as starting materials - employed in an appropriate excess - can optionally also serve as reaction auxiliaries.
Suitable diluents for carrying out the processes (a) and (b) according to the invention are especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichtoromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyt ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
When carrying out the processes (a) and (b) according to the invention, the reaction temperatures can be varied within a relatively wide range. 1n general, the processes are carried out at temperatures between 0°C and 150°C, preferably between 10°C and 120°C.

Le A 32 881-Foreign Countries The processes (a) and (b) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - in general between 0.1 bar and 10 bar.
For carrying out the processes (a) and (b) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of in each case one of the components.
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. Work-up is carried out by customary methods (cf. the Preparation Examples).
The active compounds according to the invention can be used as defoliants, desiccants, haulm-killers and, especially, as weed-killers. Weeds, in the broadest sense, are to be understood as meaning all plants which grow in locations where they are undesired. 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 be used, for example, in connection with the following plants:
Dicotyledonous 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 and Taraxacum.

Le A 32 881-Foreign Countries Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledonous weeds of the eg nera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledonous crops of the eg nera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial cultures, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, sports turf and pasture-land, and for the selective control of weeds in annual crops.
The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous or dicotyledenous crops by both the pre- and the post-emergence method.

Le A 32 881-Foreign Countries The active compounds according to the invention have potent microbicidal activity and can be employed in practice for controlling undesirable microorganisms.
The active compounds are suitable for use as fungicides.
Fungicides are employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Some pathogens causing fungal and bacterial diseases which come under the generic names listed above are 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 (conidia form: Drechslera, syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidia 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, i Le A 32 881-Foreign Countries such as, for example, Tilletia caries; Ustilago species, such as, for example, Ustilago nude or Ustilago avenge; 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 (1) according to the invention are particularly effective against mildew (Erisyphe graminis).
The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil.
The active compounds are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, encountered in agriculture, in forests, in the protection of stored products and of materials and in the hygiene sector. They are active against normally sensitive and resistant species, and against all or individual stages of development. The abovementioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and 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, for example, Scutigerella immaculate. From the order of the Thysanura, for example, Lepisma saccharine.
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 Le A 32 881-Foreign Countries migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp. From the order of the Anoplura, for example, Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp. From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Pemphigus spp., Phorodon humuli, Phylloxera vastatrix, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corm, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp.
Psylla spp. From the order of the Lepidoptera, for example, 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., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica snn.. Psvlliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Le A 32 881-Foreign Countries Anthrenus spp., Attagenus spp., Lyctus 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., S 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 paludosa. From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp. From the order of the Arachnida, for example, Scorpio maurus, Latrodectus mactans. From the order of the Acarina, for example, Acarus Biro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp. The phytoparasitic nematodes include, for example, Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Tylenchus spp., Helicotylenchus spp., Rotylenchus spp., and Tylenchulus spp.
The compounds of the general formula (I) according to the invention are highly suitable for controlling plant-damaging insects, such as, for example, diamondback moths (Plutella spp.) and aphids (Mycus spp.).
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and also very fine capsules in polymeric substances.

Le A 32 881-Foreign Countries These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-forming agents.
If the extender used is water, it is also possible to employ for example organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are:
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
suitable emulsifiers and/or foam-forming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, Le A 32 881-Foreign Countries and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are the following herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, Le A 32 881-Foreign Countries 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), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, 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, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.

Le A 32 881-Foreien Countries 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 customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between S 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 ~C2H5 OI~
FsC \ O~O~NiN
/ H
(Process (b)) With stirring, 4.5 g ( 15 mmol) of [3-trifluoromethyl-phenoxymethyl)-propylJ
chloroformate are added to a mixture of 3.1 g (30 mmol) of N-amino-morpholine and 80 ml of toluene. The reaction mixture is stirred at room temperature (approximately 20°C) for 5 hours and then washed with water, dried with sodium sulphate and filtered. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

Le A 32 881-Foreien Countries This gives 4.8 g (88% of theory) of O-[3-trifluoromethyl-phenoxymethyl)-propyl] N-(4-morpholinyl)-urethane as a solid residue of melting point 98°C.
Analogously to Example 1, and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (n listed in Table 1 below.
Ar R O
1~

Le A 32 881-Foreign Countries Table 1: Examples of the compounds of the formula (17 Ex. n Ar Q R Y Z Physical No. data 2 0 I \ CF3 O C2H5 \ nD = 1.5157 / N I /
3 1 ( ~ CF3 CH2 C2H5 NH
/ N
4 1 I ~ CF3 CH2 C2H5 NH
O
/ NJ
/
0 I ~ CF3 CH2 C2H5 CH3 / N
6 0 ~ cF3 CH2 C2H5 /
/N

7 0 I \ CFa CH2 C2H5 / /N

8 0 ~ CF3 CH2 C2H5 H3C CH3 /
/N

9 0 I ~ CF3 CH2 C2H5 \
/
N

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 0 I ~ CFa CH2 C2H5 / /

11 0 I ~ CF3 CH2 C2H5 / N
12 ~ -- ( \ cFa CH2 C2H5 / N
13 ~ - - I \ CF3 CH2 C2H5 CH3 /N

14 0 ~ CF3 CH2 C2H5 /
/N
0 I ~ CFs CH2 C2H5 H3C N' v 16 0 I ~ CF3 CH2 C2H5 Hs N

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 17 0 I \ CF3 O C2H5 \
N
18 0 \ CF3 O C2H5 CH3 /
/N
19 0 I \ CF3 O C2H5 / ~CH3 20 0 ~ CF3 O C2H5 N

21 0 \ CFs O C2H5 H3C CH3 /
/N

22 0 \ CF3 O C2H5 \
N
23 0 \ CFs O C2H5 \

Le A 32 881-Foreign Countries Ex. n Ar Q R 1, Z _ - _ physical No. data 24 0 I ~ CF3. O C2H5 / N
25 0 I ~ CF3 O C2H5 / N
cF3 O C2H5 CH3 /N

27 0 I ~ ~F3 O C2H5 / N
28 0 ~ cF3- O C2H5 /

29 0 ( ~ CFa O C2H5 Hs /
N
30 1 ~ ~F3 O C2H5 NH
/N

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 31 - 0 I \ cF3 O C2H5 H3C
/ I\

N /
32 1 \ O C2H5 NH ~O m.p.:124°C
I /
/NJ
33 1 \ CH3 O C2H5 NH ~ m.p.:114°C
I /
/N
34 1 I \ CzHs O C2H5 NH ~O m.p.:73°C
/ NJ
/
35 1 ~ O C2H5 NH O m.p.:95°C
\ CH3 I . /NJ
/
36 0 \ O C2H5 \ n20 - 1.5539 I / I D
/N /
37 0 \ CH3 O C2H5 \ n20 = 1.5500 / N I / D
/ \/
3g_ 0 I \ CzHS O C2H5-_\ nD - 1.5481 / /N I /

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 39 0 ~ CH O C2 5 \ nD = 1.5573 \ 3 I /N I /
40 1 I \ F O C2H5 NH ~ m.p.:118°C
/ N
41 0 \ F O C2H5 \--n20 = 1.5455 I/ D
/N I /
42 1 F~~ ~ ~ O C2H5 NH ~ m.p.: 124°C
/N
43 0 F~o ~ ~ O C2H5 \
I
/N /
44 1 F O C2H5 NH ~ m.p.:78°C
\ CF3 I / /N
45 0 F CF O C2H5 \ nD = 1.5081 \ 3 I /N ~ /
46 1 ~ O C2H5 NH ~O (wax) \ CF '(3 I /NJ
/

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 47 0 ~ CF O C2H5 \ nD = 1.5086 I ~ /N /
48 1 ~ CF3 O C2H5 NH ~O m.p.:123°C
I I(/
/NJ
49 0 ~ ~F3 O C2H5 \ n20 = 1.5163 D
F / /N I /
50 1 I ~ CF3 O C2H5 NH ~ nD = 1.4756 / F /N
51 0 I ~ CF3 O C2H5 \ nD = 1.4881 / F /N I /
52 1 ( ~ oCF3 O C2H5 NH ~p (wax) / NJ
/
53 0 I ~ ocF3 O C2H5 \ nD = 1.4945 / /N I /
54 1 F~ I ~ O C2H5 NH
F o i O
/NJ
55 0 F~ ( ~ O C2H5 /N

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 56 0 ~ CF3 CH2 C2H5 H3C
/ \

N /
57 0 ~ CF3 O CH3 ~ log.P = 4.788>
/
N
58 0 ( ~ CF3 O CH3 CH3 log.P = 4.648 / N
59 0 ( ~ CF3 O CH3 log.P = 4.63$
/ N
/ CHs 60 0 I ~ CFa O CH3 log.P = 4.58a~
/ N

61 0 I ~ CF3 O CH3 H3C CH3 log.P = 5.378 / N

62 0 I ~ CFs O CH3 ~ log.P = 4.69a Le A 32 881-Forei~ Countries Ex. n Ar Q R Y Z Physical No. data 63 0 I ~ CFs O CH3 log.P = 5.53$' / N
64 0 I ~ cF3 O CH3 log.P = 4.938' / N
65 0 I ~ CFs O CH3 H3 log.P = 4.998' /N

66 0 I ~ CF3 O CH3 log.P = 5.478' / N
67 0.~ \ CF3 O CH3 log.P = 5.87a>
/ ~ J
H3C N' v 68 0 I ~ ~F3 O CH3 H3 log.P = 5.87a~
N
69 1 ~ ~F3 O CH3 NH
/
/N

Le A 32 881-Foreign Countries Ex. n Ar Q R Y Z Physical No. data 70 1 ( \ CF3 O n-C4H9 NH ~0 m.p.: 81 °C
/ NJ
71 0 ~ CF3 O n-C4H9 \ n20 = 1.5132 I ( D
/ N
72 1 F O n-C3H~ NH O - m.p.: 104°C
\ CFs I /NJ
/
73 0 F CF O n-C3H~ ~ nD = 1.5033 \ 3 /N
loge values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43°C.
(a) Mobile phases for the determination in the acidic range: 0.1 % aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile -the corresponding data in Table 1 are labelled a).
(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90%
acetonitrile - the corresponding data in Table 1 are labelled b).

Le A 32 881-Foreign Countries Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) whose loge values are known (determination of the loge values by the retention times using linear interpolation between two successive alkanones).
S The lambda max values were determined in the maxima of the chromatographic signals, using the W spectra from 200 nm to 400 nm.

Le A 32 881-Foreign Countries Starting materials of the formula (III:
Example (II-11 C2Hs C ~ OH
St_e~l C ~ O
/
A mixture of 65 g (0.50 mol) of methyl propionylacetate, 34 g (0.50 mol) of sodium ethoxide and 300 ml of 1,4-dioxane is stirred at from 80°C to 90°C for 30 minutes and then, at room temperature (approximately 20°C), admixed with stirring with 97 g (0.50 mol) of 3-trifluoromethyl-benzyl chloride. The reaction mixture is stirred at from 90°C to 95°C for 18 hours and then concentrated under water pump vacuum.
The residue is stirred at 90°C in 400 ml of 20% strength aqueous sodium hydroxide solution for 4 hours, then diluted with water to about twice its original volume and shaken with methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is worked up by distillation under reduced pressure.
This gives 79.4 g (69% of theory) of ethyl 3-(3-trifluoromethyl-phenyl)-propionate of boiling point 75°C (at 0.7 mbar).

Le A 32 881-Foreign Countries Steg 2 C2Hs F3C ~ OH
At room temperature (approximately 20°C) 23 g (0.10 mol) of ethyl 3-(3-trifluoromethyl-phenyl)-propionate are added with stirnng to a mixture of 6 g of sodium borohydride (60% strength in paraffin, 0.20 mol of NaBH4), 100 ml of tetrahydrofuran and 10 ml of water, and the reaction mixture is stirred at room temperature for 18 hours. The mixture is then diluted with water to about three times its original volume and shaken with methylene chloride, and the organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is worked up by distillation under reduced pressure.
This gives 18.2 g (78% of theory) of 1-(3-trifluoromethyl-phenyl)-pentan-3-of of boiling point 78°C to 80°C (at 0.6 mbar).
Example (II-2~
C2Hs F3C ~ OOH

A mixture of 10 g (43 mmol) of 3,5-bis-trifluoromethyl-phenol, 5 g (70 mmol) of ethyloxirane and 0.2 g of lithium hydroxide is heated under reflux for 5 hours. The volatile components are then carefully distilled off under water pump vacuum.
This gives 12 g (92% of theory) of 1-(3,5-bis-trifluaromethyl-phenyl)-butan-2-of as a solid residue of melting point 53°C.

Le A 32 881-Foreignn Countries Analogously to Examples (II-1) and (II-2) it is also possible to prepare, for example, the compounds of the formula (In listed in Table 2 below.
Ar R
Q~ (II) OH
Table 2: Examples of the compounds of the formula (In Ex. No. Ar Q R Physical data II-3 ~ CF3 O C2Hg b.p.:85°C
/ ( 1 mbar) II-4 ~ O C2H5 m.p.:56°C

/
E_5 ~ cF3 O CH3 b.p.:80°C
/ ( 1 mbar) II-6 ~ CFs O C3H~-n b.p.:95°C
/ ( 1 mbar) II-7 ~ F O C2H5 b.p.:95°C
/ (2 mbar) E-g I ~ CF3 O CZHS (amorphous) F /

Le A 32 881-Foreign Countries Ex. No. Ar Q R Physical data II_9 I ~ CF3 O C2H5 (amorphous) / F
II-10 F O C2H5 (amorphous) /
II-11 ~ O C2H5 (amorphous) /
II-12 I ~ oCF3 O C2H5 (amorphous) II-13 I ~ ~H3 O C2H5 b.p.:100°C
/ (1 mbar) II-14 ~ CzHs O C2H5 b.p.:105°C
/ (0.5 mbar) II-15 I ~ O C2H5 b.p.:100°C
/ (0.5 mbar) II-16 I ~ O C2H5 (amorphous) / CFs II-17 ~ cF3 CH2 CH3 /

Le A 32 881-Foreign Countries Ex. No. Ar Q R Physical data II-18 I ~ CF3 CH2 C3H~-n II-19 F ~ ~ O CH3 F
F /
F O
II-20 F ~ ~ O C2H5 F~ I /
F O

Le A 32 881-Foreign Countries Starting-materials of the formula (IVI:
Example (IV-1) CZHS O
C ~ 0I 'CI
At room temperature (about 20°C), a solution of 120 g (0.52 mol)) of 1-(3-trifluoromethyl-phenyl)-pentan-3-of in 600 ml of toluene is added dropwise with stirnng to a mixture of 800 ml of toluene, 3 ml of N,N-dimethyl-formamide and 54 g (0.55 mol) of phosgene. The reaction mixture is then stirred at 60°C
for 8 hours. The solvent is subsequently carefully distilled off under water pump vacuum.
This gives 144 g (94% of theory) of O-[1-ethyl-3-(3-trifluoromethyl-phenyl)-propyl]
chloroformate as an amorphous residue which can be employed without further purification as starting material for the process (b) according to the invention.

Le A 32 881-Foreign Countries Use Examples:
Example A
Pre-emergence test S
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.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the preparation of active compound. The amount of water per unit area is advantageously kept constant. The concentration of active compound in the preparation is immaterial, only the active compound application rate per unit area matters.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0 % = no effect (like untreated control) 100 % = total destruction In this test, for example, the compounds of Preparation Example 1 and 40 exhibit strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, barley.

Le A 32 881-Foreign Countries 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 of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0 % = no effect (like untreated control) 100 % = total destruction In this test, for example, the compounds of Preparation Example 1, 2, 33, 34 and 40 exhibit strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, wheat.

Le A 32 881-Foreign Countries Example C
Erysiphe test (barley) / induction of resistance Solvent: 48.8 parts by weight of N,N-dimethylformamide Emulsifier: 1.2 parts by weight of alkylaryl palyglycol 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 preparation of active compound at the stated application rate. 4 days after the treatment, the plants are inoculated with spores of Erysiphe graminis f. sp. hordei. The plants are subsequently 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 efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
In this test, for example, the compounds of Preparation Example 8, 10, 11, 12, 13, 14, 15, 16 and 56 exhibit, at an application rate of 750 g/ha, an efficacy of from 80% to 95%.

Le A 32 881-Foreign Countries 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.
Seedlings of the broad bean (Vicia faba minor) which are infested by the green peach aphid (Myzus persicae) are dipped into the preparation of active compound of the desired concentration and placed into a box made of plastic.
After the desired period of time, the kill in per cent is determined. 100%
means that all aphids have been killed; 0% means that none of the aphids have been killed.
In this test, for example, the compounds of Preparation Example 21, 26, 29 and exhibit, at an active compound concentration of 0.1 %, a kill of from 90 to 100%.

Le A 32 881-Foreign Countries Example E
Plutella test / synthetic 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 stated amount of the preparation of active compound of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, a film box lid covered with approximately 100 plutella eggs is placed onto each cavity. The freshly hatched larvae migrate onto the treated synthetic feed.
After the desired period of time, the kill in % is determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.
In this test, for example, the compounds of Preparation Examples 22, 23 and 69 exhibit, at an active compound concentration of 0.1%, an efficacy of 95%.

Claims

1. Substituted alkoxycarbonylcompounds of the general formula (I), in which n represents the numbers 0 or 1, Ar represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbocyclic or heterocyclic grouping, Q represents O (oxygen), S (sulphur), SO, SO2, NH, N(alkyl) or CH2 (methylene), R1 represents alkyl or cycloalkyl, R2 represents hydrogen or alkyl, Y represents NH or N(alkyl), and Z represents in each case optionally substituted, monocyclic or bicyclic, saturated or partially unsaturated heterocyclyl which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case optionally substituted cycloalkylamino or arylamino.

2. Substituted alkoxycarbonyl compounds according to Claim l, characterized in that n represents the numbers 0 or 1, Ar represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbocyclic or heterocyclic grouping from the group consisting of cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the - likewise optionally substituted grouping below where A represents optionally halogen-substituted alkanediyl having 1 to 3 carbon atoms, where the substituents which are possible in each case are preferably selected from the list below:
cyano, nitro, halogen, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl having in each case up to 6 carbon atoms, Q represents O (oxygen), S (sulphur), SO, SO2, NH, N(C1-C4-alkyl) or CH2 (methylene), R1 represents alkyl having 1 to 6 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms, R2 represents hydrogen or alkyl having 1 to 4 carbon atoms, Y represents NH or N(C1-C4-alkyl), and Z represents in each case optionally substituted aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thio-morpholinyl, S,S-dioxo-thiomorpholinyl, perhydroazepinyl, pipera-zinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, tetrahydroquinolinyl, perhydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, each of which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case optionally substituted cycloalkylamino having 3 to 6 carbon atoms or arylamino having 6 or 10 carbon atoms, where the substituents which are possible in each case are preferably selected from the list below:
cyano, nitro, halogen, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl having in each case up to 6 carbon atoms.

3. Substituted alkoxycarbonyl compounds according to Claim 1, characterized in that n represents the numbers 0 or l, Ar represents an in each case optionally substituted, monocyclic or bicyclic, saturated or - if appropriate partially - unsaturated, carbo-cyclic or heterocyclic grouping from the group consisting of cyclo-hexyl, phenyl, naphthyl, tetralinyl, decalinyl, furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, or the likewise optionally substituted groupings below where A represents in each case optionally fluorine- and/or chlorine-substituted methylene or dimethylene (ethane-1,2-diyl), and where the substituents which are possible in each case are preferably selected from the list below:
cyano, nitro, fluorine, chlorine, bromine, in each case optionally fluorine- and/or chlorine-substituted 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, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methyl-sulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, Q represents O (oxygen), S (sulphur), SO, SO2, NH, N(methyl) or CH2 (methylene), R1 represents methyl, ethyl, n- or i-propyl, or represents cyclopropyl, R2 represents hydrogen or methyl, Y represents NH, N(methyl), N(ethyl) or N(i-propyl), and Z represents in each case optionally substituted pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl, S,S-dioxo-thio-morpholinyl, perhydroazepinyl, piperazinyl, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, tetrahydroquinolinyl, per-hydroquinolinyl, tetrahydroisoquinolinyl or perhydroisoquinolinyl, each of which is attached via N, or - if n is 1 or Ar represents a bicyclic grouping - also represents in each case optionally substituted cyclohexylamino or phenylamino, where the substiutents which are possible in each case are preferably selected from the list below:
cyano, nitro, fluorine, chlorine, bromine, in each case optionally fluorine- and/or chlorine-substituted 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, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methyl-sulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl.

4. Substituted alkoxycarbonyl compounds according to Claim 3, characterized in that Ar represents the grouping below in which R3 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy and R4 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, and R1 represents methyl, ethyl, n- or i-propyl.

5. Substituted alkoxycarbonyl compounds according to Claim 4, characterized in that Q represents oxygen.

6. Substituted alkoxycarbonyl compounds according to Claim 4, characterized in that Q represents sulphur, SO or SO2.

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 CH2(methylene).

9. Substituted alkoxycarbonyl compounds according to Claim 3, characterized in that Ar represents one of the groupings below Q represents oxygen, R1 represents methyl, ethyl, n- or i-propyl.

10. Process for preparing substituted alkoxycarbonyl compounds according to any of claims 1 to 9, characterized in that (a) substituted alkanols of the general formula (II) in which Ar, Q, R1 and R2 are as defined in any of Claims 1 to 9 are reacted with isocyanates of the general formula (III) O=C=N-Z (III) in which Z is as defined in any 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 (b) chloroformic esters of the general formula (IV) in which Ar, Q, R1 and R2 are as defined in any of Claims 1 to 9 are reacted with nucleophilic compounds of the general formula (V) H-(Y)n-Z (V) in which n, Y and Z are as defined in any 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 of Claims 1 to 9 as herbicide, fungicide and/or insecticide.

12. Crop protection composition, characterized in that it comprises at least one substituted alkoxycarbonyl compound according to any of Claims 1 to 9 and customary extenders.