DE19937500A1 - Substituted heterocyclylbenzofurans - Google Patents

Abstract

The invention relates to novel heterocyclylbenzofuranes of general formula (I) wherein Z, R<1>, R<2>, R<3> and R<4> have the meanings as cited in the description. The invention also relates to a method for the production and use thereof as herbicides.

Description

The invention relates to new substituted heterocyclylbenzofurans, a process for their manufacture and their use as herbicides.

It is already known that certain substituted heterocyclylbenzofurans herbi have both properties (cf. EP-A-476697, EP-A-561319, WO-A-97/07104 / EP-A-850227, WO-A-97/28127 / EP-A-885885). However, these connections have has so far gained no special significance.

The new substituted heterocyclylbenzofurans of the general formula (I)

in which
R ^{1 represents} hydrogen, cyano or halogen,
R ^{2 represents} cyano or thiocarbamoyl,
R ³ for hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thio carbamoyl, halogen, for hydroxyiminoalkyl or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkoxyiminoalkyl, alkenyl, Alkenyloxy, alkenylthio, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkylalkyl, cycloalkyloxycarbonyl, phenyl or benzyl,
R ⁴ for hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, for hydroxyiminoalkyl or for optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl alkylsulfonyl, alkylcarbonylamino, alkoxyiminoalkyl, alkenyl, alkenyloxy, alkenylthio, alkenylthio Alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkylalkyl, cycloalkyloxycarbonyl, phenyl or benzyl, and
Z represents one of the heterocyclic groupings below,

in which
Q represents O (oxygen) or S (sulfur),
R ⁵ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkyl thio, alkylamino, alkoxycarbonyl, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy, alkynylthio, cycloalkyl or cycloalkyl alkyl, and
R ^{6 represents} hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where optionally two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO -, SO ₂ -, -NH- or -N (alkyl) - at the beginning (or at the end) or interrupted alkanediyl or alkenediyl within the hydrocarbon chain,
found.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl - also in connection with heteroatoms, such as in alkoxy - are in each case straight-chain or branched.
R ¹ preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
R ² preferably represents cyano or thiocarbamoyl.
R ³ preferably represents hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, hydroxyiminoalkyl having up to 6 carbon atoms, each optionally by cyano, hydroxy, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms, for each if appropriate by cyano, halogen or C ₁ -C ₄ -Alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino or alkoxyiminoalkyl, each having up to 6 carbon atoms, for alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio each having up to 6 carbon atoms each optionally substituted by cyano or halogen, each for ge optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl, cycloalkylalkyl or cycloalkyloxycarbonyl, each having 3 to 6 carbon atoms in the cy cloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy.
R ⁴ preferably represents hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, hydroxyiminoalkyl having up to 6 carbon atoms, each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms, each optionally with cyano, halogen or C ₁ -C ₄ alkoxy substituted alkoxycarbonyl, alkylcarbonylamino or alkoxyiminoalkyl, each having up to 6 carbon atoms, for alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio each having up to 6 carbon atoms, each optionally substituted by cyano or halogen, each optionally by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl, cycloalkylalkyl or cycloalkyloxy carbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy.
Z preferably represents one of the heterocyclic groupings below,

Q is preferably O (oxygen) or S (sulfur).
R ⁵ preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for each alkyl, alkoxy, alkylthio, alkylamino or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy 6 carbon atoms, for dialkylamino each having up to 4 carbon atoms in the alkyl groups, for each optionally substituted by cyano or halogen substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio each having up to 6 carbon atoms, or each optionally by cyano, halogen or C ₁ -C ₄ alkyl-substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part.
R ⁶ preferably represents hydrogen, hydroxy, amino, cyano, for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, each optionally by cyano or halogen-substituted alkenyl or alkynyl each having up to 6 carbon atoms, for each cyclo alkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl partly, or for phenyl, benzyl or phenylethyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy.

Two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - may optionally together stand for halogen-substituted and / or optionally O (oxygen), S (sulfur) or a group the series -SO-, SO ₂ -, -NH- or -N (C ₁ -C ₄ alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each with up to 5 carbon atoms.
R ¹ particularly preferably represents hydrogen, fluorine or chlorine.
R ² particularly preferably represents cyano or thiocarbamoyl.
R ³ particularly preferably represents hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for hydroxyimino methyl, hydroxyiminoethyl or hydroxyiminopropyl, for where appropriate in each case by cyano, hydroxy, fluorine, chlorine, methoxy , Ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl 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, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy n- or i-butyroylamino, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyi minoethyl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, each optionally substituted by cyano, fluorine or chlorine, for each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopropyl, Cyclo butyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropyloxycarbonyl, Cyclo butyloxycarbonyl, Cyclopentyloxycarbonyl or Cyclohexyloxycarbonyl, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl or methyl.
R ⁴ particularly preferably represents hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, hydroxyiminomethyl, hydroxyiminoethyl or hydroxyiminopropyl, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-Propoxy, methyl thio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methyl sulfonyl or ethylsulfonyl 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, methylsulfinyl, ethylsulfinyl , Methylsulfonyl or ethylsulfonyl, for methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , for each optionally by Cyano, Fl Propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, substituted for chlorine or chlorine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyloxy carbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyl oxycarbonyl, or for each phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl or methoxy.
Z particularly preferably represents one of the heterocyclic groupings below,

Q particularly preferably represents O (oxygen) or S (sulfur).
R ⁵ particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propyl amino, n-, i-, s- or t-butylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, for dimethylamino or diethylamino, each optionally with cyano or fluorine, Chloro or bromine substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, or for cyclopropyl, cyclobutyl, cyclopentyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl , Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentyl methyl or Cyclohexylmethyl.
R ⁶ particularly preferably stands for hydrogen, hydroxyl, amino, cyano, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t, which is in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t- Butoxycarbonyl, methyl amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine or chlorine, for each optionally by cyano , Fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or, or for phenyl or benzyl substituted in each case optionally by nitro, cyano, fluorine, chlorine, bromine, methyl or methoxy.

If appropriate, two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - together if appropriate together represent optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO ₂ -, -NH- or -N (methyl) - at the beginning (or at the end) or interrupted propane-1,3-diyl (trimethylene), butane within the hydrocarbon chain 1,4-diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl.
R ¹ very particularly preferably represents fluorine.
R ² very particularly preferably represents cyano.
R ³ very particularly preferably represents hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, each methyl optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally with cyano, fluorine, chlorine, Methoxy or ethoxy substituted methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl.
R ⁴ very particularly preferably represents hydrogen.
Z very particularly preferably represents one of the heterocyclic groupings below,

Q very particularly preferably represents O (oxygen) or S (sulfur).
R ⁵ very particularly preferably represents hydrogen, fluorine, chlorine, bromine, in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, methoxy, ethoxy, n- or i-propoxy, Methylamino, ethylamino, n- or i-propylamino, for dimethyl amino, for propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, each optionally substituted by cyano or fluorine, chlorine or bromine .
R ⁶ very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or propenyl, butenyl optionally substituted by cyano, fluorine or chlorine , Propynyl or butynyl.

Two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - if appropriate very particularly preferably together represent optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO ₂ -, -NH- or -N (methyl) - at the beginning (or at the end) or propane-1,3-diyl (trimethylene), butane which is interrupted within the hydrocarbon chain 1,4-diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl.

The individual radicals R ⁵ and R ⁶ - insofar as they are connected to the same heterocyclic grouping more than once, can have the same or different meanings in the context of the definitions given above as preferred, particularly preferred or very 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.

Those compounds of the formula (I) are preferred according to the invention which is a combination of the meanings listed above as preferred is present.

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

According to the invention, those compounds of the Formula (I), in which a combination of the above is particularly preferred added listed meanings is present.

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.

A very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q, R ⁵ and R ^{6 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q and R ^{6 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
R ^{5 has} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q and R ^{5 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q and R ^{5 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
R ⁵ and R ^{6 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q, R ⁵ and R ^{6 have} the meaning given above as being particularly preferred.

Another very particularly preferred group are those compounds of the formula (I) in which
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above as being particularly preferred and
Z represents the heterocyclic grouping below,

wherein
Q, R ⁵ and R ^{6 have} the meaning given above as being particularly preferred.

The new substituted heterocyclylbenzofurans of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal activity.

The new substituted heterocyclylbenzofurans of the general formula (I) are obtained if 3-alkynyloxyphenylheterocycles of the general formula (II)

in which
R ¹ , R ² , R ³ , R ⁴ and Z have the meaning given above,
pyrolyzed in the presence of basic nitrogen compounds and optionally in the presence of metal fluorides.

If, for example, 4- (3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) -5-fluoro-2 - [(1-methyl-2 -propinyl) -oxy] -benzonitrile as starting material, the course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the 3-alkynyloxyphenyl heterocycles to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), R ¹ , R ² , R ³ , R ⁴ and Z preferably or in particular have those meanings which are preferred or as already mentioned above in connection with the description of the compounds of the general formula (I) according to the invention particularly preferably for R ¹ , R ² , R ³ , R ⁴ and Z have been given.

The starting materials of the general formula (II) are known and / or can be according to processes known per se (cf. EP-A-370332, EP-A-597360, EP-A-599135, EP-A-610733, EP-A-617026, WO-A-96/18618, WO-A-97/30980, WO-A-97/26248, WO-A-97/40018, WO-A-97/46535, production examples).

The process for the preparation of compounds of general formula (I) is carried out using basic organic nitrogen compounds. These preferably include trimethylamine, triethylamine, tripropylamine, tri butylamine, ethyl diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexyl amine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-diethyl-aniline, N, N-Di methyl-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-di methylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO),  1,5-diazabicyclo [4,3,0] non-5-ene (DBN), 1,8 diazabicyclo [5,4,0] -undec-7-ene (DBU) and 1,3-dimethyl-2-imidazolidinedione.

1,3-Dimethyl-2-imidazolidinedione is a basic organic nitrogen compound particularly well suited in the method according to the invention.

The process for the preparation of compounds of general formula (I) is optionally carried out using metal fluorides. This includes preferably lithium, sodium, potassium, rubidium, cesium, magnesium, Calcium, barium and aluminum fluoride.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 150 ° C and 250 ° C, preferably between 180 ° C and 220 ° C.

The process of the invention are generally under normal pressure carried out. However, it is also possible to use the method according to the invention increased or reduced pressure - generally between 0.1 bar and 10 bar - perform.

When carrying out the process according to the invention, the reaction Components generally mixed at room temperature and the reaction Mixing is generally required for one or more hours Temperature stirred. Working up is carried out according to customary methods (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. in the following plants be used:

Dicotyledon weeds of the genera

Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera

Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera

Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera

Alijum, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.  

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.

The active compounds according to the invention are suitable depending on the concentration tration for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.

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-impregnated nated natural and synthetic substances 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, that is emulsifiers and / or dispersants and / or foam generators resources.  

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 emulsions goals such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite 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, Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (- sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, Butylates, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo methoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorine sulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra sulfuron (methyl), chlorosulam (methyl), cumyluron, cyanazine, cybutryne, 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, Di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop- (-P-ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-  methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet sulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, fluprop acil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr ( meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiaz uron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxa diazon, oxasulfisron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendi methalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primi sulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulf uron (-ethyl), pyrazoxyfen, pyribenzoxime, 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, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thia fluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarb azil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin and triflusulfuron.

Also a mixture with other known active ingredients, such as fungicides, insects ticides, acaricides, nematicides, bird repellants, plant nutrients substances 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 solder solutions, suspensions, emulsions, powders, pastes and granules 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

A mixture of 1.0 g (3 mmol) of 4- (3-difluoromethyl-4-methyl-5-oxo-4,5-dihydro- 1H-1,2,4-triazol-1-yl) -5-fluoro-2 - [(1-methyl-2-propynyl) -oxy] -benzonitrile, 20 ml 1,3- Dimethyl-2-imidazolinedione and 2 mg of potassium fluoride is stored at 200 ° C for 4 hours Stirred 210 ° C, stirred after cooling with water and with conc. Hydrochloric acid acidic set (pH 2). The precipitated product is isolated by suction, with water washed and by column chromatography on silica gel with toluene / acetic acid ethyl ester (vol .: 3: 1) cleaned.

0.40 g (40% of theory) of 4- (3-difluoromethyl-4-methyl-5-oxo-4,5- dihydro-1H-1,2,4-triazol-1-yl) -2-ethyl-5-fluoro-1-benzofuran-7-carbonitrile from Melting point 115 ° C (logP: 2.79).

Example 2

A mixture of 1.3 g (3.9 mmol) of 4- (3-difluoromethyl-4-ethyl-5-oxo-4,5-dihydro- 1H-1,2,4-triazol-1-yl) -5-fluoro-2 - [(2-propynyl) oxy] benzonitrile and 20 ml of N, N-Di ethyl aniline is stirred for one hour at 210 ° C, stirred after cooling with water and with conc. Hydrochloric acid made acidic (pH 2). The failed product by Ab  suck isolated, washed with water and column chromatographed over silica gel cleaned with toluene / ethyl acetate (vol .: 3: 1).

0.60 g (46% of theory) of 4- (3-difluoromethyl-4-ethyl-5-oxo-4,5-dihydro- 1H-1,2,4-triazol-1-yl) -2-methyl-5-fluoro-1-benzofuran-7-carbonitrile from the melt point 102 ° C (logP: 2.73).

Analogously to Examples 1 and 2 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

Table 1

Examples of the compounds of the formula (I)

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

• a) eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a) .
• b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^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 8.0 g (50 mmol) of 4-cyano 2-fluoro-5-methoxy-aniline, 7.4 g (50 mmol) phthalic anhydride and 150 ml of methanol is refluxed for 2 days heated. Then 0.8 g of 4-dimethylamino-pyridine are added and the The mixture is refluxed for a further 24 hours. Then the is concentrated Residue mixed with water and ethyl acetate, the precipitated product isolated by suction and washed with water.

11.2 g (76% of theory) of N- (2-fluoro-4-cyano-5-methoxyphenyl) are obtained. phthalimide with a melting point of 245 ° C (logP: 2.51).

Level 2

10.6 g (35.8 mmol) of N- (2-fluoro-4-cyano-5-methoxyphenyl) phthalimide are described in 300 ml of dichloromethane are introduced and at 10 ° C to 20 ° C 107 ml (107 mmol) Boron tribromide (1 molar solution in dichloromethane) was added dropwise. The Mixture is stirred at 25 ° C. for 2 days, then water is added, 10 minutes after stirred and the solid product isolated by suction.

9.2 g (91% of theory) of N- (2-fluoro-4-cyano-5-hydroxy-phenyl) -phthalate are obtained imide of melting point 247 ° C (logP: 2.04).

level 3

A mixture of 3.0 g (10.6 mmol) of N- (2-fluoro-4-cyano-5-hydroxy-phenyl) - phthalimide, 100 ml acetonitrile, 1.91 g (13.8 mmol) potassium carbonate and 1.39 g (11.7 mmol) propargyl bromide is refluxed for 18 hours. Subsequently is concentrated, the residue is mixed with ethyl acetate and 2N hydrochloric acid, and the precipitated product is isolated by suction.

1.8 g (52.9% of theory) of N- (2-fluoro-4-cyano-5-propargyloxyphenyl) are obtained. phthalimide with a melting point of 242 ° C.  

Example (II-2))

1.0 g (3.55 mmol) of N- (2-fluorine-4-cyano-5-hydroxy-phenyl) -phthalimide are described in 40 ml of tetrahydrofuran with 1.02 g (3.9 mmol) of triphenylphosphine and 0.30 g (4.26 mmol) 3-butyn-2-ol submitted and with ice cooling (max 20 ° C) 0.70 g (3.9 mmol) diethyl azodicarboxylate (dissolved in 20 ml tetrahydrofuran) given. The mixture is stirred at 25 ° C. for 24 hours, concentrated and over Silica gel cleaned with cyclohexane / ethyl acetate 2: 1.

0.35 g (29% of theory) of N- [2-fluoro-4-cyano-5- (but-1-in-3-yl) -oxy is obtained phenyl] phthalimide, melting point 170 ° C (logP: 2.92).  

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 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Amount of active ingredient is applied per unit area. The drug concentration in the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired amount of active ingredient is applied.

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 2 very 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 5- 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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 2 very strong action against weeds.

Claims (8)

1. Compounds of the general formula (I),
in which
R ^{1 represents} hydrogen, cyano or halogen,
R ^{2 represents} cyano or thiocarbamoyl,
R ³ for hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, for hydroxyiminoalkyl or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkoxyiminoalkyl, alkenyl, alkenyl, alkenyl , Alkenylthio, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkylalkyl, cycloalkyloxy carbonyl, phenyl or benzyl,
R ⁴ for hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thio carbamoyl, halogen, for hydroxyiminoalkyl or for optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl alkylsulfonyl, alkylcarbonylamino, alkoxyiminoalkyl, alkenyl, alkenyloxy, alkenylthio, alkenylthio , Alkynyloxy, alkynylthio, cycloalkyl, cycloalkylalkyl, cycloalkyloxycarbonyl, phenyl or benzyl, and
Z represents one of the heterocyclic groupings below,
in which
Q represents O (oxygen) or S (sulfur),
R ^{5 represents} hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxycarbonyl, dialkyl amino, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy, alkynylthio, Cycloalkyl or cycloalkylalkyl, and
R ^{6 represents} hydrogen, hydroxy, amino, cyano, or their optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenyl alkyl,
where optionally two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO -, SO ₂ -, -NH- or -N (alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl. 2. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, cyano, fluorine, chlorine or bromine,
R ³ for hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, for hydroxyiminoalkyl having up to 6 carbon atoms, each optionally by cyano, hydroxy, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms, each optionally with cyano, halogen or C ₁ - C ₄ -alkoxy-substituted alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino or alkoxyiminoalkyl, each having up to 6 carbon atoms, for alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio each having up to 6 carbon atoms, each optionally substituted by cyano or halogen, for each given if appropriate cycloalkyl, cycloalkylalkyl or cycloalkyloxycarbonyl substituted by cyano, halogen or C ₁ -C ₄ alkyl and each having 3 to 6 carbon atoms in the cycloalkyl groups and the like nd optionally represents up to 4 carbon atoms in the alkyl part, or represents phenyl or benzyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ⁴ for hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thio carbamoyl, halogen, for hydroxyiminoalkyl having up to 6 carbon atoms, each optionally with cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -Alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ -alkyl sulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms, for each ge optionally by cyano, halogen or C ₁ -C ₄ alkoxy substituted alkoxycarbonyl, alkylcarbonylamino or alkoxyiminoalkyl, each having up to 6 carbon atoms, for alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio, each optionally substituted by cyano or halogen, each having up to 6 carbon atoms, each optionally by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl, cycloalkylalkyl or cyclo alkyloxycarbonyl each having 3 to 6 carbon atoms in the cyclo alkyl groups and optionally up to 4 Koh lenstoffatomen in the alkyl part, or for phenyl or benzyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, and
Z for one of the heterocyclic groupings below,
in which
Q represents O (oxygen) or S (sulfur),
R ⁵ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, for alkyl, alkoxy, alkylthio, alkyl amino or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each with up to 6 carbon atoms, for dialkylamino each having up to 4 carbon atoms in the alkyl groups, for alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio each having up to 6 carbon atoms each optionally substituted by cyano or halogen, or for each optionally by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, and
R ⁶ for hydrogen, hydroxy, amino, cyano, for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, for alkenyl optionally substituted by cyano or halogen or alkynyl each having up to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, or for each phenyl, benzyl or phenylethyl optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, or
two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - optionally together if appropriate for optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the Series -SO-, SO ₂ -, -NH- or -N (C ₁ -C ₄ alkyl) - are at the beginning (or at the end) or within the hydrocarbon chain under broken alkanediyl or alkenediyl, each having up to 5 carbon atoms. 3. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, fluorine or chlorine,
R ³ for hydrogen, amino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for hydroxyiminomethyl, hydroxyiminoethyl or hydroxyiminopropyl, for where appropriate by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n - or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl 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, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionyl amino, n optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy - or i-butyroylamino, methoxyiminomethyl, ethoxyimino methyl, methoxyiminoethyl or ethoxyiminoethyl, each for where appropriate, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for cyclopropyl, cyclobutyl substituted by cyano, fluorine or chlorine , Cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxy carbonyl, or phenyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl or methoxy
R ⁴ for hydrogen, amino, nitro, carboxy, cyano, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, for hydroxyiminomethyl, hydroxy iminoethyl or hydroxyiminopropyl, each optionally with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i -Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl 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, methylsulfinyl, ethyl sulfinyl, Methylsulfonyl or ethylsulfonyl, for methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methoxy iminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminomethyl, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , each optionally substituted by cyano, fluorine or chlorine first propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclo butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyloxy carbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxycarbonyl, or for phenyl or benzyl optionally substituted in each case by nitro, cyano, fluorine, chlorine, bromine, methyl or methoxy, and
Z represents one of the heterocyclic groupings below,
in which
Q represents O (oxygen) or S (sulfur),
R ⁵ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxy carbonyl, for dimethylamino or diethylamino, for where appropriate by cyano or fluorine, chlorine or bromine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl stands, and
R ⁶ for hydrogen, hydroxy, amino, cyano, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxy carbonyl, methylamino, Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine or chlorine, for each optionally substituted by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or, or each represents phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl or methoxy, or two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - if appropriate particularly preferably together for optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO ₂ -, -NH- or -N (methyl) - at the beginning (or at the end) or interrupted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl. 4. Compounds according to claim 1, characterized in that
R ^{1 represents} fluorine,
R ^{2 represents} cyano,
R ³ for hydrogen, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, each for methyl, ethyl, n-substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for each methoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy carbonyl, n- or i-propoxycarbonyl,
R ^{4 represents} hydrogen, and
Z represents one of the heterocyclic groupings below,
in which
Q represents O (oxygen) or S (sulfur),
R ⁵ for hydrogen, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, meth- or ethoxy, n- or i-propoxy, methylamino, ethylamino, n optionally substituted by fluorine, chlorine, methoxy or ethoxy - or i-Propylamino, for dimethylamino, for propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, each optionally substituted by cyano or fluorine, chlorine or bromine, and
R ^{6 stands} for hydrogen, for amino, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine or chlorine , or
two adjacent radicals - R ⁵ and R ⁵ , R ⁶ and R ⁶ or R ⁵ and R ⁶ - if appropriate particularly preferably together for optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO ₂ -, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted propane-1,3-diyl (trimethylene), butane 1,4-diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl. 5. A method for producing connections according to one of claims 1 to 4, characterized in that
3-alkynyloxyphenyl heterocycles of the general formula (II)
in which
R ¹ , R ² , R ³ , R ⁴ and Z have the meaning given above,
be pyrolyzed in the presence of basic nitrogen compounds and optionally in the presence of metal fluorides. 6. A method for controlling unwanted vegetation, thereby characterized in that at least one compound according to one of the Claims 1 to 4 on undesirable plants and / or their habitat can act. 7. Use of at least one compound according to one of the claims 1 to 4 for controlling unwanted plants. 8. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 4 and conventional extenders and / or surfactants.