WO2002081473A1 - Substituted azoloazin(thi)ones - Google Patents

Abstract

The invention relates to novel substituted azoloazin(thi)ones of general formula (I), wherein Q1, Q2, Q3, Q4, R, Y and Z have the meaning as cited in the description. The invention also relates to a method for the production thereof and the use thereof as plant treating agents.

Description

Substituted azoIoazin (thi) one

The invention relates to new substituted azoloazin (thi) ones and a process for their preparation as well as the use of substituted azoloazin (thi) ones

Plant treatment agents, in particular as herbicides.

Individual substituted azolotriazinones, such as the compounds 3-acetyl-pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one, l-oxopyrrolo [l, 2-d] [l, 2,4] triazine-2 (1H) -acetic acid, 1-oxoxyrrolo [1, 2-d] [1, 2,4] triazine-2 (1 H) -acetic acid methyl ester, 4-methyl-1 - oxo-pyrrolo [l, 2-d] [l, 2,4] triazine-2 (lH) acetic acid and 4-methyl-l-oxo-pyrrolo [l, 2-d] - [l, 2,4] triazine-2 (1H) -acetic acid methyl ester (cf. J. Heterocycl. Chem. (1980), 17, 631-635 - cited in Chem. Abstracts 94: 3990), the compound 3-acetyl-1-acetyloxy -pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one (cf. J. Heterocycl. Chem. (1981), 18, 743-746 - cited in Chem. Abstracts 95: 169141), the compounds 4-oxopyrazolo

[1, 5-d] [1, 2,4] triazine-5 (4H) -acetic acid and 4-oxo-pyrazolo [1, 5-d] [1, 2,4] triazine-5- (4H) - methyl acetate (cf. J. Heterocycl. Chem. (1982), 19, 817-822 - cited in Chem. Abstracts 98: 53805), as well as the compounds 1,8-dimethyl-3- (2-oxo-2- phenyl-ethyl) -6-propyl-imidazo [1,5-d] [1,2,4] triazin-4 (3H) -one, 1,8-dimethyl-4-oxo-6-propyl-imidazo [1 , 5-d] [1, 2,4] triazin-3 (4H) -acetic acid, 1, 8-dimethyl-4-oxo-6-propyl-imidazo [l, 5-d] [l, 2,4] ethyl triazine-3 (4H) -acetate, 8-methyl-4-oxo-6-propyl-imidazo [1,5-d] [1,2,4] ethyl-triazine-3 (4H) -acetate, 8 -Methyl-4-oxo-imidazo [l, 5-d] [l, 2,4] triazin-3 (4H) -acetic acid ethyl ester and 4-oxo-imidazo [l, 5-d] - [l, 2 , 4] triazine-3 (4H) -acetic acid ethyl ester (cf. J. Med. Chem. 28 (1985), 1704-1716 - cited in Chem. Abstracts 104: 5848) are already known from the (patent) literature

(See also CR Acad. Sci., Ser. C (1972), 274, 1703-1706 - cited in Chem. Abstracts 77: 61962; Tetrahedron Lett. (1973), 35, 3239-3241; J. Heterocycl. Chem . (1979), 16, 277-282; J. Org. Chem. (1993), 58, 6620-6624; Heterocycles (1995), 41, 329-336; Tetrahedron (1999), 55, 13703-13724; US -4107309; US-5750522). However, the use of these compounds as plant treatment agents has hitherto not been disclosed. Some imidazotriazinones, optionally substituted by alkyl groups, such as, for example, the compounds imidazo [1,5-d] l, 2,4] triazin-4 (3H) -thione, 8-methylimidazo [1,5-d] [l , 2,4] triazine-4 (3H) -thione, 6-propyl-imidazo [l, 5-d] l, 2,4] triazine-4 (3H) -thione, 6,8-dimethyl-imidazo [l , 5-d] [l, 2,4] triazine-4 (3H) -thione, 6-methyl-imide-azo [l, 5-d] [l, 2,4] triazine-4 (3H) -thione , 6-propyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -thione, 6,8-dimethyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -one, 6-butyl-imidazo [l, 5-d] - [l, 2,4] triazin-4 (3H) -one, 6-methyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -one and 8-methyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -one, but are already considered potential Herbicides have become known (see US-4,107,307, US-4,124,766, US-4, 168,964).

The new substituted azoloazin (thi) ones of the general formula (I)

in which

a bond drawn in dashed lines represents a single bond or a double bond,

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

Q ^{3 stands} for N (nitrogen) or C (carbon) with the proviso that in each

In individual cases the neighboring atoms Q ^{3 are} different and Q ³ if it is for C (Carbon) is connected via a double bond to the neighboring Q ⁴ ,

Q ^{4 stands} for N (nitrogen) or the grouping CX,

R is hydrogen, hydroxyl, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, Alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, dialkylamino or aryl,

X is hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylamino-nylsulfonyl stands,

Y stands for a single bond or for optionally substituted alkanediyl, alkenediyl, alkindiyl or cycloalkanediyl, and

Z for hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, or for each optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino, N-alkyl-hydroxyamino, alkylhydrazino, dialkylamino, N-alkylalkoxyamino .

Dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy, alkynylamino, dialkenylamino, dialldnylaniino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylhydrazinσ, cycloalkylalkyl, cycloalkylalkyl, arylyl aryl, arylylyl aryl, arylyl aryl, arylyl aryl, arylyl aryl, arylyl aryl, arylyl aryl, arylyl aryl, arylyl aryl, arylamino Arylalkyl, arylalkoxy, arylalkylthio,

Arylalkylamino, N-alkyl-N-arylalkylamino, N-alkyl-N-arylamino, N- Alkenyl-N-aryl-amino, N-alkynyl-N-aryl-amino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,

found,

where the above-mentioned compounds known from the literature 3-acetyl-pyrrolo [1,2-d] [1,2,4] triazin-4 (3H) -one, l-oxopyrrolo [1,2-d] [ 1,2,4] triazine-2 (1H) acetic acid, 1-oxopyrrolo [1,2-d] [1,2,4] triazine-2 (1H) -acetic acid methyl ester, 4-methyl-1 -oxo-pyrrolo [l, 2-d] [l, 2,4] triazin-2 (lH) -acetic acid and 4-methyl-l-oxo-pyrrolo [l, 2-d] [l, 2,4] triazine-2 (1H) -acetic acid methyl ester (cf. J. Heterocycl. Chem. (1980), 17, 631-635 - cited in Chem. Abstracts 94: 3990), the compound 3-acetyl-1-acetyloxy-pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one (see J. Heterocycl. Chem. (1981), 18, 743-746 - cited in Chem. Abstracts 95: 169141) , the compounds 4-oxopyrazolo [l, 5-d] [l, 2,4] triazin-5 [4H) acetic acid and 4-oxopyrazolo [l, 5-d] [l, 2, 4] triazin

5 [4H) -acetic acid methyl ester (cf. J. Heterocycl. Chem. (1982), 19, 817-822 - cited in Chem. Abstracts 98: 53805), as well as the compounds 1, 8-dimethyl-3- (2 -oxo-2-phenyl-ethyl) -6-propyl-imidazo [l, 5-d] [l, 2,4] triazin-4 (3H) -on, l, 8-dimethyl-4-oxo-6- propyl-imidazo [1, 5-d] [1, 2,4] triazin-3 (4H) -acetic acid, 1, 8-dimethyl-4-oxo-6-propyl-imidazo [1,5-d] [l , 2,4] triazine-3 (4H) -acetic acid ethyl ester, 8-methyl-4-oxo-6-propyl-imidazo [l, 5-d] [l, 2,4] triazine-3 (4H) - ethyl acetate, 8-methyl-4-oxo-imidazo [l, 5-d] [l, 2,4] triazine-3 (4H) -acetic acid ethyl ester and 4-oxo-imidazo [l, 5-d] [- 1,2,4] triazine-3 (4H) -acetic acid ethyl ester (cf. J. Med. Chem. 28 (1985), 1704-1716 - cited in Chem. Abstracts 104: 5848) are excluded by disclaimer.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as in alkoxy. Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.

The compounds of the general formula (I) according to the invention optionally contain one or more asymmetrically substituted carbon atoms and in these cases can be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms. In these cases, the invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the

Mixtures of these isomeric compounds.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are described below.

Q ¹ preferably represents O (oxygen).

Q ² preferably represents O (oxygen).

Q ⁴ preferably represents the grouping CX.

R preferably represents hydrogen, hydroxy, amino, cyano, carboxy, carbamoyl, Thiocarbarnoyl, halogen, represents in each case optionally cyano-, halogen, _{Cι-C4-alkoxy,} Ci- alkylcarbonyl, C ₁ -C ₄ - alkoxycarbonyl, CC ₄ -Alkylthio, C ₁ -C ₄ -Alkylsulfιnyl or C ₁ -C -alkylsulfonyl substituted

Alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkoxycarbonylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally by halogen, C 1 -C -Alkyl or CrC-ralkoxy substituted phenyl or naphthyl. X preferably represents hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by cyano, halogen, CrC ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl, C ** - C ₄ - Alkoxycarbonyl, -C-C ₄ - alkylthio, C -C ₄ alkylsulfmyl or - alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl in each case with the 1-bisulfonyl alkyl groups.

Y preferably represents a single bond or alkanediyl, alkenediyl, alkynediyl each having up to 6 carbon atoms or cycloalkanediyl having 3 to 6 carbon atoms, each of which is optionally substituted by nitro, cyano, hydroxy, mercapto, amino or the —C (Q ^! ) -Z group , where appropriate the Z of the above group -C (Q ¹ ) -Z may also together with the Z defined below represent O (oxygen), NH or alkanediyl having 1 to 3 carbon atoms.

Z preferably represents hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, each in each case optionally by cyano, halogen, Ci

C ₄ -alkoxy, dC ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl, C * ι-C ₄ - alkylthio, -C ₄ - alkylsulfinyl or - -alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino , N-alkyl-hydroxyamino, alkylhydrazino, dialkylamino, N-alkylalkoxyamino or dialkylhydrazino, each having 1 to 10 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkmyloxy or alkynylamino optionally substituted by cyano or halogen 2 to 6 carbon atoms in each case, for dialkenylamino or dialkinylamino in each case up to 10 carbon atoms in the alkenyl or alkynyl groups, for each optionally by cyano,

Halogen or C ₁ -C ₄ alkyl substituted cycloalkyl, cycloalkyloxy, cyclo- alkylamino, Cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy or Cycloalkylalkylamino with 3 alkyl group up to 6 carbon atoms in the cyclo and optionally 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally substituted by nitro, cyano, hydroxy, halogen, C ^* ι-C ₄ - alkyl, Cj-C ₄ haloalkyl, -C-C ₄ alkoxy or C ₁ -C ₄ -HaJogenalkoxy substituted

Aryl, arylcarbonyl, aryloxy, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, NC ₁ -C ₄ -alkyl-N-arylalkyl-amino, NC ₁ -C ₄ -alkyl-N-aryl-amino, NC ₂ -C ₄ -alkenyl-N-arylamino, NC ₂ --C ₄ -alkynyl-N-arylamino, each having 6 or 10 carbon atoms in the aryl group and optionally up to 4 carbon atoms in the alkyl part, or for each optionally by nitro , cyano, hydroxy, halogen, C * ι-C ₄ - alkyl, C ₁ -C ₄ -haloalkyl, C * ι-C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, Cι * -C ₄ - alkylthio, C --C ₄ -Halogenalkylthio, C ₁ -C ₄ - alkylsulfinyl, C] -C ₄ -haloalkylsulfinyl, Cι-C ₄ -alkylsulfonyl or C ₁ -C ₄ -haloalkylsulfonyl-substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino

Heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclicalkylamino each with up to 10 carbon atoms, up to 5 nitrogen atoms and / or up to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part.

particularly preferably represents hydrogen, hydroxyl, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n - or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetyloxy, propionyloxy, n - or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino , Propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, dimethylamino or diethylamino.

X particularly preferably represents hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl , Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl , n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, dietyl or diethylaminosulfonyl.

Y particularly preferably represents a single bond or methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene) which is optionally substituted by nitro, cyano, hydroxyl, mercapto, amino or the —C (Q ¹ ) -Z group , - CH (CH ₃ ) -), ethane-l, 2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ », propane -l, 2-diyl (-CH (CH ₃ ) CH ₂ -), propane-l, 3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-l, 2-diyl (-CH = CH -), propene-1,2-diyl (- CH = C (CH ₃ », propene-1,3-diyl (-CH = CH-CH ₂ -), ethine-1,2-diyl or ethine-1, 3-diyl, cyclopropane-l, l-diyl, cyclopropane-1,2-diyl, cyclobutane-l, l-diyl, cyclobutane-1,2-diyl, cyclopentane-l, l-diyl, cyclopentane 1,2- diyl, cyclohexane-l, l-diyl or cyclohexane-1,2-diyl. particularly preferably represents hydrogen, hydroxy, mercapto, amino,

Hydroxyamino, hydrazino, carbamoyl, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio , Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i -Butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarb- onyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino , Methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, dimethylamino, diethylamino, N-methyl-methoxyamino or dimethylhydrazino, each optionally with cyano, fluorine, chlorine or or bromine-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for diallyla ino or dipropargyla ino, for where appropriate by cyano, fluorine , Chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclohexylmethyl propylmethyl , Cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, each optionally with nitro, cyano, hydroxy, fluorine, chlorine, bromine or methyl, ethyl, n-, n- , i-, s- or t-butyl, difluorme ethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluoro-dichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di- fluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, naphthyl, phenylcarbonyl, naphthylcarbonyl, phenyloxy, naphthyloxy, phenylthio, naphthylthio, phenylamino, naphthylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylethylmethylethylmethyloxyphenyl Phenylethylamino, N-

Methyl-N-phenylmethyl-amino, N-ethyl-N-phenylmethyl-amino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino, Ni Propyl-N-phenyl-amino, N-allyl-N-phenyl-amino or N-propargyl-N-phenyl-amino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, Fluordichlormethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, methylthio, ethylthio, difluoromethylthio, tri- fluoromethylthio, fluorodichloromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclyl-methyl, heterocyclyl-methoxy, Heterocyclylmethylthio or heterocyclylmethy lamino where in each case the heterocyclyl group is selected in particular from the series

Furyl, tetrahydrofuryl, thienyl, pyrrolyl, indolyl, indolinyl, pyrazolyl, pyrazolinyl, pyrrolidinyl, oxazolyl, isoxazolyl, isoxazolidinyl, thiazolyl, pyridinyl, piperidinyl, quinolinyl, isoquinolinyl, tetrahydroquinolinyl, tetra.

very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl tes methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, acetyloxy, propionyloxy, methoxycarbonyloxy, ethoxy carbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, acetylamino, propionylamino, methoxycarbonylamino, ethoxyethylaminoamino.

X very particularly preferably represents hydrogen, nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl,

Ethyl, n- or i-propyl, acetyl, propionyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino , Dimethylamino, Dimethylaminocarbonyl or Dimethylaminosulfonyl.

Y very particularly preferably represents a single bond or methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH.) Which is optionally substituted by cyano, hydroxyl or the grouping -C (Q ¹ ) -Z ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ ) -),

Propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,3-diyl (-CH = CH- CH ₂ -), ethyne-1,2-diyl or ethyne-1,3-diyl.

Z very particularly preferably represents hydrogen, hydroxy, mercapto, amino,

Carbamoyl, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy, each optionally substituted by cyano, fluorine, chlorine or bromine, Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclohexyloxy, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Cyclopropylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethylamino, Cyclo-pentylmethylamino or Cyclohexylmethylamino r each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy-substituted phenyl, phenyl, phenyl, phenyl Phenyloxy, phenylthio, phenylamino, phenylmethyl, phenylmethoxy, phenylmethylthio, phenylmethylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or Ni-propyl- N-phenylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl , Trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl,

Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluorodichloromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, fluorodichloromethylthio, chlorodifluoromethyl-methylylethyl, methylsulfonyl, methylsilyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsilyl, methylsulfonyl, methylsulfonyl, methylsiloxyl, methylsiloxyl, methylsiloxyl substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclyl amino, heterocyclylmethyl, heterocyclylmethoxy, heterocyclylmethylthio or heterocyclylmethylamino where in each case the heterocyclyl group is selected in particular from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazylidyl, thiazolyl, thiazole.

R most preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, acetyl, methoxy, ethoxy, acetyloxy, propionyloxy, methoxycarbonyl or ethoxycarbonyl.

X most preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, acetyl, propionyl, methoxy or ethoxy, each of which is optionally substituted by fluorine or chlorine.

Y most preferably represents a single bond, methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ ) -) or ethane-1,2-diyl (dimethylene,

-CH ₂ CH).

Z most preferably represents hydrogen, hydroxy, amino, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, for methylamino, ethylamino, n- or i-propylamino, for dimethylamino or diethylamino, each optionally by fluorine, chlorine, methyl, ethyl, difluoromethoxy, trifluoromethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylamino or phenylmethyl.

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

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

Most preferred according to the invention are the compounds of formula (I) in which there is a combination of the meanings listed as most preferred above.

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

A very particularly preferred group of compounds of the general formula (I) are the compounds of the following formula (IA)

in which

A represents N (nitrogen) or the grouping C-X,

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur), R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,

Ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio,

Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ^I for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl Y for a single bond or for methylene (-CH ₂ -), ethane-U-diyl (ethylidene, -CH (CH ₃ ) -), ethane which is optionally substituted by cyano, hydroxy or the grouping -C (Q ^! ) -Z - 1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-l, 2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,3-diyl ( -CH = CH-CH ₂ -), ethine-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl,

Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,

Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i -, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy which are each optionally substituted by cyano, fluorine, chlorine or bromine,

Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy,

Fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl, phenyl oxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or Ni-propyl-N-phenyl-amino.

The above-mentioned known compounds 3-acetyl-pyrrolo [1,2-d] [1,2,4] triazine

4 (3H) -one and 3-acetyl-l-acetyloxy-pyrrolo [1,2-d] [1,2,4] triazin-4 (3H) -one are complete for the compounds defined by formula (LA.) Disclaimer excluded.

Another very particularly preferred group of compounds of the general formula (I) are the compounds of the general formula (LB)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q -.2 ^{z represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino

X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine,

Chlorine, bromine, or for methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl or ethylsulfonyl,

Y for a single bond or for methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH. Optionally substituted by cyano, hydroxy, mercapto, amino or the group -C (Q ¹ ) -Z ₃ ) -), ethane-1,2-diyl

(Dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -) , Propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ -), ethyne-1,2-diyl or ethyne-1,3-diyl, and Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i -Propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each for optionally by Cyano, fluorine, chlorine or bromine substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or he butynylamino, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N Propyl-N-phenyl-amino or Ni-propyl-N-phenyl-amino.

The above-mentioned known compounds 1 -oxo-pyrrolo [1,2-d] [1,2,4] triazine-2 (1 H) -acetic acid, 1 -oxo-pyrrolo [1,2-d] [1,2 , 4] triazine-2 (1H) -acetic acid methyl ester, 4-methyl-1-oxopyrrolo [1, 2-d] [1, 2,4] triazine-2 (1H) -acetic acid and 4-methyl- 1-oxopyrrolo [l, 2-d] [l, 2,4] triazine-2 (lH) -acetic acid methyl ester are for those by formula

(TB) defined connections excluded by disclaimer. Another very particularly preferred group of compounds of the general formula (I) are the compounds of the general formula (IC)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methoxy,

Ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for each optionally substituted by cyano, hydroxy, mercapto, amino or the grouping -C (Q ^! ) -Z

Methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l -diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ -), ethyne-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,

Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy optionally substituted by cyano, fluorine, chlorine or bromine, Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, each for if appropriate

Cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclo- butyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, Phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, N-propyl-N-phenylamino or Ni-propyl-N-phenylamino.

The above-mentioned known compounds 1,8-dimethyl-3- (2-oxo-2-phenyl-ethyl) -6-propyl-imidazo [1,5-d] [1,2,4] triazine-4 (3H) -one, 1,8-dimethyl-4-oxo-6-propyl-imidazo [1,5-d] [1,2,4] triazin-3 (4H) -acetic acid, 1,8-dimethyl-4-oxo -6-propyl-imidazo [l, 5-d] [l, 2,4] triazine-3 (4H) -acetic acid, ethyl ester, 8-methyl-4-oxo-6-propyl-imidazo [l, 5-d ] [l, 2,4] triazine-3 (4H) -acetic acid ethyl ester, 8-methyl-4-oxo-imidazo- [l, 5-d] [l, 2,4] triazine-3 (4H) - ethyl acetate and 4-oxo-imidazo [1,5-d] 2,4,4-triazine-3 (4H) -acetic acid ethyl ester are excluded from the disclaimer for the compounds defined by formula (IC).

Another very particularly preferred group of compounds of the general formula (I) are the compounds of the general formula (ID)

in which

Q ^{1 represents} O (oxygen) or S (sulfur), Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl, ethylsulfonyl

Y for a single bond or for each optionally by cyano,

Hydroxy, mercapto, amino or the group -C (Q ^! ) -Z substituted

Methylene (-CH ₂ -), ethane-1,1-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-1,1 -diyl (propylidene, -CH (C ₂ H ₅ ) -), propane

1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), Ethene-1,2-diyl (-CH = CH-), propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ - ), Ethine-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl,

Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy each optionally substituted by cyano, fluorine, chlorine or bromine , Propynylamino or butynylamino, for each cyclopropyl, cyclobutyl, cyclopentyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, Cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy-substituted phenyl, phenylcarbonyl, phenylcarbonyl, Phenylthio, phenylamino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, N-propyl-N-phenylamino or Ni-propyl-N-phenylamino.

The above-mentioned known compounds 4-oxopyrazolo [l, 5-d] [l, 2,4] triazine ** - 5-

(4H) -acetic acid and 4-oxo-pyrazolo [1,5-d] [1,2,4] triazine-5 (4H) -acetic acid-methyl- esters are excluded from the disclaimer for the compounds defined by formula (ID).

Another very particularly preferred group of compounds of the general formula (I) are the compounds of the following formula (IE)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl,

Ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, X is hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for each optionally by cyano,

Hydroxy or the grouping -C (Q ¹ ) -Z substituted methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-1,1-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane 1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,3-diyl (-CH = CH-CH ₂ -) , Ethyne-1,2-diyl or ethyne

1,3-diyl stands, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i -Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,

Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine,

Propynyloxy, butynyloxy, propynylamino or butynylamino, for each optionally cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, substituted by cyano, fluorine, chlorine, methyl or ethyl, or, in each case, optionally by nitro , Hydroxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n - or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl- N-phenyl-amino or Ni-propyl-N-phenyl-amino.

The new substituted azoloazin (thi) ones of the general formula (I) and also the compounds excluded by disclaimers are notable for strong and selective herbicidal activity.

The new substituted azoloazin (thi) ones of the general formula (I) are obtained if azoloazin (thi) ones of the general formula (II)

in which

Q ² , Q ³ , Q ⁴ and R have one of the meanings given above,

with compounds of the general formula (III)

in which

Q ¹ , Y and Z have one of the meanings given above and

X ^{3 represents} halogen or the grouping -YC (Q ¹ ) -Z, where Y, Q ¹ and Z in turn have one of the meanings given above,

if appropriate in the presence of one or more reaction auxiliaries and, if appropriate, in the presence of one or more diluents,

and optionally the compounds of the general formula (I) thus obtained are converted into other compounds of the general formula (I) according to the definition of the substituent by customary methods.

If, for example, pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one and ethyl chloroacetate are used as starting materials, the course of the reaction in the process according to the invention can be sketched using the following formula:

The azoloazin (thi) ones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II), üi the general formula (II) have Q ² , Q ³ , Q ⁴ and R preferably those meanings which have already been mentioned above in connection with the description of the compounds of the general Formula (I) has been given as preferred, particularly preferred, very particularly preferred or most preferred for Q ² , Q ³ , Q ⁴ and R.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. C. R. Acad. Sei., Ser. C (1972),

274, 1703-1706 - cited in Chem. Abstracts 77: 61962; Tetrahedron Lett. (1973), 35, 3239-3241; J. Heterocycl. Chem. 16: 277-282 (1979); loc. cit. 17: 631-635 (1980); loc. cit. 18: 743-746 (1981); loc. cit. 19: 817-822 (1982); J. Med. Chem. 28: 1704-1716 (1985); J. Org. Chem. (1993), 58, 6620-6624; Heterocycles (1995), 41, 329-336; Tetrahedron (1999), 55, 13703-13724; US 4107307; US 4107309; US 4124766; US

4168964; US 5,750,522).

Formula (III) provides a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III) Q ¹

Y and Z preferably have the meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for Q ¹ , Y and Z; X ³ preferably represents chlorine, bromine, iodine or the grouping -YC (Q ¹ ) -Z, where Q ¹ , Y and Z have the meanings given above as preferred, particularly preferred, very particularly preferred or most preferred.

The starting materials of the general formula (HI) are organic synthetic chemicals known to the person skilled in the art.

The process for the preparation of the compounds of the general formula (I) is preferably carried out using one or more reaction auxiliaries. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanols, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium , Potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or

Potassium methoxide, ethanolate, n- or i-propanolate, n-, i-, -s or t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, 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-methylpiperidine, 1,4-diazabicyclo [2.2.2] octane (DABCO), l, 5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1.8 diazabicyclo [ 5.4.0] -undec-7-en (DBU).

Phase transfer catalysts are also suitable as further reaction aids for the process according to the invention. Examples of such catalysts are:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromimididylammonidylammonylammonylammonylammonylammonylammonylammonylammonyl benzylammonium benzylammonium benzyl methylammonium hydroxide, berizyl triethyl ammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributylhexadecylphosphonium phosphonium bromide, butyl triphenyl triphenyl triphenyl, ethyl Tetraphenylphosphonium bromide.

The process according to the invention for the preparation of the compounds of the general

Formula (I) is preferably carried out using one or more diluents. carried out medium. In addition to water, diluents for carrying out the process according to the invention are in particular inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be varied over a wide range in the implementation of the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

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

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.

Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

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

Dicotyledon weeds of the genera: 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, Rorippex, Rotal 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.

Monocotyledon 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: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means limited to these

Limited genera, but extends in the same way to other plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on

Because of and places with and without tree cover. The active compounds according to the invention for weed control in permanent crops, e.g. Forest, 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 land as well as for selective purposes Weed control can be used in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

In certain concentrations or application rates, the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crops). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.

Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying,

Evaporation, nebulization, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by means of single- or multi-layer coating.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,

Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.

Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are also possible possible with weed control agents which contain one or more known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenimole, cafenimole Carbetamides, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidone (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (- propargon) Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Dialates, dicamba, dichloroprop (-P), diclofop (-methyl), diclosula m, diethatyl (-ethyl), difenzoquate,

Diflufenican, Diflufenzopyr, Dimefiiron, Dimepiperate, Dimethachlor, Dimetha- metryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, EtobenzanidPenamide, Fenoxap, Flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,

Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyr-sulfüron (-methyl, -sodium), Flurenol (-butyl), Fluroxyryl (-butoxy-propyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fom-safen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, - P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturonaben, Isouronach, Isouron, Isouron, Isouron, Isouron, Isouron, Isouron, Isouron Isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, methyl sulfonin, metrulfurin, metribuzin Monolinuron, Naproanilide, Napropamide, Neburon, Nico sulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, pico-linafen, piperophos, pretilachynlu, primazulfurlu, primazulfurl, primisulfurl Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarbi-, Pyrid, Pyributicarbi-, Pyridate Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl) , Sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobarbcarb, tiocarbazil, tralkoxyduulfuron, triallate, triallate, triallate, triallate, triallate, triallate, triallate ron (-methyl), Triclopyr, Tridiphane, Trifluralin, Trifloxysulfuron, Triflusulfuron (-methyl), Tritosulfuron.

Known safeners are also suitable for the mixtures, for example

AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, Dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

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

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

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

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wildly occurring mende or plant species and their parts obtained by conventional organic breeding methods, such as crossing or protoplast fusion. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified

Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. There are, for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals

Active substances -, better plant growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of the crop plants to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of crop products, higher

Shelf life and / or workability of the harvested products possible, which go beyond the effects to be expected.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, received genetic material which contained them Gives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicides

Agents. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton and rapeseed are highlighted. The traits are particularly emphasized as the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryLA (b), CryLA (c), CryLIA, CrylllA, CryIILB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YLELD GARD® (e.g.

Corn, Cotton, Soybean), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rapeseed), LMI® (tolerance against Imidazolinone) and STS®

(Tolerance to sulfonylureas e.g. maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market with these or future-developed genetic properties ("traits").

The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I or the active compound mixtures according to the invention, the above-mentioned synergistic effects also occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

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

Manufacturing examples:

example 1

A mixture of 0.54 g (4.0 mmol) of imidazo [1,2-d] [1,2,4] triazin-5 (6H) -one, 0.535 g (4.4 mmol) of ethyl chloroacetate, 0 , 66 g (4.8 mmol) of potassium carbonate and 40 ml of acetonitrile is heated to boiling under reflux for 15 hours. The mixture is then concentrated under reduced pressure, the residue is taken up in ethyl acetate and shaken with aqueous 1N hydrochloric acid. The aqueous phase is shaken with ethyl acetate and the organic phases are then combined, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with diethyl ether / petroleum ether and the product obtained in crystalline form is isolated by suction.

0.50 g (55% of theory) of 5-oxo-imidazo [1,2-d] [1,2,4] triazine-6 (5H) ethyl acetate of melting point 88 ° C. is obtained.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, the compounds of the general formula (I) - or of the formulas (LA), (LB), (IC), (LD ) or (IE).

Table 1: Examples of the compounds of the formula (I) or of the formulas (LA), (ffi), (IC), (LD) or (IE)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

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

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

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

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

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, it is mixed

1 part by weight of active ingredient with the specified amount of solvent, add the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

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

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

In this test, for example, the compounds according to Preparation Examples 4, 5 and 14, with good tolerance to crop plants, such as, for example, maize, show a 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 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

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

1000 1 water / ha the desired amounts of active ingredient are applied.

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

It means:

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

In this test, for example, the compounds according to Preparation Examples 1, 4, 5 and 14 show that they are well tolerated by crop plants, such as e.g. Corn and sugar beet, strong weed control.

Claims

claims

1. Compounds of the general formula (I)

in which

a bond drawn in dashed lines represents a single bond or a double bond,

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

Q ^{3 stands} for N (nitrogen) or C (carbon) with the proviso that the neighboring atoms Q ^{3 are} different in each individual case and Q ³ , if it stands for C (carbon), is connected to the neighboring Q ⁴ via a double bond is

Q ^{4 stands} for N (nitrogen) or the grouping CX,

R for hydrogen, hydroxy, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkoxy- carbonylamino, alkylaminocarbonylamino, dialkylamino or aryl,

X represents hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl

Y for a single bond or for each optionally substituted

Alkanediyl, alkenediyl, alkindiyl or cycloalkanediyl, and

Z represents hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino,

Alkoxyamino, N-alkyl-hydroxyamino, alkylhydrazino, dialkylamino, N-alkyl-alkoxyamino, dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkmyloxy, alkynylamino, dialkenylamino, dialkynylamino, cycloalkyl, cycloalkylamino, cycloalkylo cycloalkylino, cyclo Cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, N-alkyl-N-arylalkylamino, N-alkyl-N-arylamino, N-alkenyl-N- arylamino, N-alkynyl-N-arylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,

where the compounds 3-acetyl-pyrrolo [l, 2-d] [l, 2,4] triazin-4 (3H) -one, 1-oxo-pyrrolo [l, 2-d] [l, 2,4] triazin-2 (lH) acetic acid, l-oxopyrrolo [l, 2-d] -

[l, 2,4] triazine-2 (lH) -acetic acid methyl ester, 4-methyl-l-oxo-pyrrolo [l, 2-d] - [1, 2,4] triazine-2 (1 H) -acetic acid, 4-methyl-1-oxo-pyrrolo [1, 2-d] [1, 2,4] triazine-2 (1 H) -acetic acid methyl ester , 3-acetyl-l-acetyloxy-pyrrolo [l, 2-d] [l, 2,4] triazine-4 (3H) -one, 4-oxo-pyrazolo [l, 5-d] [l, 2,4] triazine-5 (4H) -acetic acid, 4-oxopyrazolo [1,5-d] [1,2,4] triazine-5 (4H) -acetic acid methyl ester, 1,8-dimethyl-3 - (2-oxo-2-phenyl-ethyl) -6-propyl-imidazo [1,5-d] 1,2,4] triazin-4 (3H) -one, 1,8-

Dimethyl-4-oxo-6-propyl-imidazo [1,5-d] [1,2,4] triazine-3 (4H) -acetic acid, 1,8-dimethyl-4-oxo-6-propyl-imidazo [ l, 5-d] [l, 2,4] triazine-3 (4H) -acetic acid, ethyl ester, 8-methyl-4-oxo-6-propyl-imidazo [l, 5-d] [l, 2,4 ] triazine-3 (4H) - ethyl acetate, 8-methyl-4-oxo-imidazo [1,5-d] [1,2,4] triazine-3 (4H) - ethyl acetate, 4-oxo- imidazo [1, 5-d] [1, 2,4] triazine-3 (4H) -acetic acid ethyl ester are excluded.

2. Compounds of formula (I) according to claim 1, characterized in that

Q ^{1 stands} for O (oxygen),

Q ^{2 stands} for O (oxygen),

Q ⁴ stands for the grouping CX,

R for hydrogen, hydroxy, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for each optionally by cyano, halogen, C ₁ -C ₄ -alkoxy, CrC ₄ -alkylcarbonyl, C1-C ₄ -alkoxycarbonyl, - C -alkylthio , C ₁ -C ₄ alkylsulfinyl or - alkylsulfonyl substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkoxycarbonylamino or dialkylamino, each with 1 to 6 carbonamino in the alkyl groups, or for each optionally by Halogen, dC ₄ alkyl or C * -C ₄ alkoxy substituted phenyl or naphthyl,

X for hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by

Cyano, halogen, -C ₄ alkoxy, C 1-C ₄ - alkylcarbonyl, Cι-C ₄ alkoxy carbonyl, C ₁ -C ₄ alkylthio, Cι-C - alkylsulfinyl or C ₁ -C ₄ substituted alkyl -Alkylsulf- onyl , Alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl each with 1 to 6

Carbon atoms in the alkyl groups,

Y for a single bond or for alkanediyl, alkenediyl, alkynediyl, each optionally substituted by nitro, cyano, hydroxy, mercapto, amino or the grouping -C (Q ¹ ) -Z, each with up to 6

Carbon atoms or cycloalkanediyl having 3 to 6 carbon atoms, where appropriate the Z of the above group -C (Q ¹ ) -Z also together with the Z defined below are O (oxygen), NH or alkanediyl having 1 to 3 carbon atoms can, and

Z for hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, for each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, CrC ₄ - alkylcarbonyl, C ₁ -C ₄ - alkoxycarbonyl, C ₁ - C ₄ - alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ - alkylsulfonyl substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino, N-alkyl-hydroxyamino, alkylhydrazino, dialkylamino, N-alkylalkoxyamino or dialkylhydrazino each having 1 to 10 carbon atoms in the alkyl groups, for alkenyl optionally substituted by cyano or halogen,

Alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino each having 2 to 6 carbon atoms, for dialkenylamino or dialkynylamino each having up to 10 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkyloxy, cycloalkylamino which are optionally substituted by cyano, halogen or C 1 -C ₄ -alkyl, Cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, hydroxy, halogen, C ₁ -C ₄ -alkyl, - -haloalkyl , Cι-C ₄ -alkoxy or C ^* ι-C ₄ haloalkoxy substituted aryl,

Arylcarbonyl, aryloxy, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, NC ₁ -C ₄ -alkyl-N-arylalkyl-amino, NC ₁ -C ₄ -alkyl-N-aryl-amino, NC ₂ -C _4- alkenyl-N-aryl-amino, NC ₂ -C ₄ -alkynyl-N-aryl-amino, each having 6 or 10 carbon atoms in the aryl group and optionally up to 4

Carbon atoms in the alkyl part, or for each optionally by nitro, cyano, hydroxy, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ** - C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, -C ₄ - haloalkylthio, ^ -alkylsulfonyl, C ₁ -C ₄ haloalkylsulfinyl, C ^* ι-C4 alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted

Heterocyclyl, heterocyclyloxy, heterocyclyltbio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino, each with up to 10 carbon atoms, up to 5 nitrogen atoms and / or up to 2 oxygen or sulfur atoms and optionally 1 to 4 sulfur atoms and 1 to 4 sulfur atoms

Carbon atoms in the alkyl part.

3. Compounds of formula (I) according to claim 1 or 2, characterized in that R for hydrogen, hydroxy, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,

Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i- propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarb- onyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarb- onyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i- Propylaminocarbonyloxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, acetylamino, propionylamino, n- or i-butyroylylamino, methoxy , n- or i-propoxycarbonylamino, dimethylamino or diethylamino,

X for hydrogen, nitro, amino, formyl, cyano, carboxy, carbamoyl,

Thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n - or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino .

Ethylamino, n- or i-propylamino, dimethylamino, diethylamino, Dimethylaminocarbonyl, Diefhylaminocarbonyl, Dimethylaminosulfonyl or Diethylaminosulfonyl stands,

Y for a single bond or for methylene (-CH ₂ -), ethane-1,1-diyl (ethylidene, -CH) optionally substituted by nitro, cyano, hydroxyl, mercapto, amino or the grouping -C (Q ¹ ) -Z (CH ₃ ) -), ethane-l, 2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1, 2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimefhylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), Propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ -),

Ethyne-1,2-diyl or ethyne-1,3-diyl, cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclobutane-1,2-diyl, Cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclohexane-1,1-diyl or cyclohexane-1,2-diyl and

Z for hydrogen, hydroxy, mercapto, amino, hydroxyamino, hydrazino, carbamoyl, for in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,

Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n- , i-, s- or t-butylhydrazino, dimethylamino, diethylamino, N-methyl-methoxyamino or dimethylhydrazino, for each optionally substituted by cyano, fluorine, chlorine or bromine Ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for diallylamino or dipropargylamino, for cyclopropyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclobutyl

Cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclo-pentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino, cyclopentylhydrazyl, cyclohexylhydrazyl, cyclo-propylmethyl, cyclo-propylmethyl, cyclo-propylmethyl, cyclo-propylmethyl Cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, each optionally with nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, naphthyl, phenylcarbonyl, naphthyloxy, naphthyl, carbonyl , Phenylamino, naphthylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino, N-methyl-N-phenylmethylamino, N-ethyl-N-phenylmethylamino, N-methyl-N -phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino, Ni-propyl-N-phenyl-amino, N-allyl-N-phenyl-amino or N-propargyl-N phenylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, Trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-

Propoxy, difluoromethoxy, trifluoromethoxy, fluorodichloromethoxy, Chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, fluorodichloromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonylsulfonyl, trifluoromethylsulfonyl, trifluoromethyl

Heterocyclylamino, Heterocyclylmethyl, Heterocyclylmethoxy, Heterocyclylmethylthio or Heterocyclylmethylamino where the heterocyclyl group in each case is selected in particular from the series Furyl, Tetrahydrofuryl, Thienyl, Pyrrolyl, Indolyl, Indolinyl, Pyr-azolazolylolyl, pyrolylazolyl, pyrolazolyl, pyrolazolyl, pyrolazolylazolylyl, pyrolazolylazolylolyl, pyrolazolylazolylolylazolylylazolylazolylylazolylazolylylazolylazolylazolylazolylazolyloxyrylazolyl, pyrolazolylazololylazolylazolylazolylazolyloloxylazolyloxylazolylazolyloxyloloxylazolyloxyrylazolylazolylazolyloxylazolylazolyloxyloloxylazolylazolylazolylazolyloxyrylazolylazole

Thiazolyl, pyridinyl, piperidinyl, quinolinyl, isoquinolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, pyrimidinyl, morpholinyl or piperazinyl.

Compounds of formula (I) according to any one of claims 1 to 3, characterized in that

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, acetyloxy, propionyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, propylamino, methylamyl, ethylamylamino, methylamyl, ethylamyl, methylamyl, ethylamyl, methylamyl, ethylamyl, methylamyl, ethylamyl, methylamyl, ethylamyl, methylamyl, ethylamyl, methylamyl, methylamyl, methylamyl, methylamyl, ethylamylamino or methylamyl , Acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino or dimethylamino,

X represents hydrogen, nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by Cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxy, ethoxy, n - or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, dimethylamino, dimethylaminocarbonyl or dimefhylaminosulfonyl,

Y for a single bond or for methylene (-CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ », ethane, optionally substituted by cyano, hydroxy or the group -C (Q ¹ ) -Z) - 1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl (propylidene, -CH (C ₂ H ₅ », propane-l, 2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene,

-CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,3-diyl (-CH = CH-CH ₂ -), ethyne-1,2-diyl or ethine-1,3-diyl and

Z for hydrogen, hydroxy, mercapto, amino, carbamoyl, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, Propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each for optionally by Cyano, fluorine, chlorine or bromine substituted ethenyl, propenyl, butenyl, propenyloxy, Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclobutyloxy, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclohexyloxy,

Cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, each optionally by cyano,

Hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl,

Phenyloxy, phenylthio, phenylamino, phenylmethyl, phenylmethoxy, phenylmethylthio, phenylmethylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or Ni-propyl-N- phenylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl , Trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoro-dichloromefhoxy, chlorodifluoromethoxy, fluorethoxy, chloroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethylthio, trifluoromethyl Methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylmethyl, heterocyclic ethoxy, heterocyclylmethylthio or heterocyclylmethylamino where eils the heterocyclyl group in particular selected is from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl or pyrimidinyl.

5. Compounds of formula (I) according to any one of claims 1 to 4, characterized in that

R represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, acetyl, methoxy, ethoxy, acetyloxy, propionyloxy, methoxycarbonyl or ethoxycarbonyl,

X represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, acetyl, propionyl, methoxy or ethoxy which are each optionally substituted by fluorine or chlorine,

Y for a single bond, methylene (-CH ₂ -), ethane-1,1-diyl

(-CH (CH ₃ ) -) or ethane-1,2-diyl (-CH ₂ CH ₂ -) and

Z for hydrogen, hydroxy, amino, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, methoxy, ethoxy, n- or i-propoxy, n -, i-, s- or t-butoxy, for methylamino,

Ethylamino, n- or i-propylamino, represents dimethylamino or diethylamino, each represents phenyl, phenylcarbonyl, phenyloxy, phenylamino or phenylethyl, optionally substituted by fluorine, chlorine, methyl, ethyl, difluoromethoxy, trifluoromethoxy.

6. Compounds of the formula (IA)

in which

A represents N (nitrogen) or the grouping C-X,

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino,

Is ethylamino or dimethylamino,

X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, X for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for each optionally by cyano,

Fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Ethoxycarbonyl, methylthio,

Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for methylene optionally substituted by cyano, hydroxy or the grouping -C (Q ¹ ) -Z (-

CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-l, l-diyl ( Propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ - ), Ethene-l, 2-diyl (-CH = CH-), propene-l, 3-diyl (- CH = CH-CH ₂ -), ethyne-l, 2-diyl or ethyne-1, 3-diyl stands, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-

Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n- , i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for each ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino optionally substituted by cyano, fluorine, chlorine or bromine, Ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopentylamino or Cyclohexylamino, or for each optionally by nitro, C yano,

Hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl,

Phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or N-i-propyl-N-phenyl-amino,

where the compounds 3-acetyl-pyrrolo [1,2-d] [1,2,4] triazin-4 (3H) -one and

3-Acetyl-1-acetyloxy-pyrrolofl, 2-d] [1, 2,4] triazin-4 (3H) -one are excluded.

7. Compounds of formula (IB)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X is hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for methylene (-CH ₂ -), ethane-1,1-diyl (ethylidene, -CH (CH. Optionally substituted by cyano, hydroxy, mercapto, amino or the group -C (Q ^! ) -Z ₃ », ethane-1,2-diyl (dimethylene, -CH ₂ CH -), propane-1,1-diyl (propylidene, -CH (C ₂ H ₅ », propane-l, 2-diyl (-CH ( CH ₃ ) CH ₂ -), propane-l, 3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,2 - diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ -), ethyne-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t -Butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy which are optionally substituted by cyano, fluorine, chlorine or bromine , Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl , Cyclohexyloxy, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino or Cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, tri chloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N -phenyl-amino, N-propyl-N-phenyl-amino or Ni-propyl-N-phenyl-amino,

where the compounds l-oxo-pyrrolo [l, 2-d] [l, 2,4] triazin-2 (lH) acetic acid, 1-oxoxyrrolo [1, 2-d] [1,2,4] methyl triazine-2 (1 H) -acetate, 4-methyl-1-oxo-pyrrolo [l, 2-d] [1,2,4] triazine-2 (lH) -acetic acid and 4-methyl-l - oxopyrrolo [1, 2-d] [1, 2,4] triazine-2 (1 H) -acetic acid methyl ester are excluded.

8. Compounds of formula (IC)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for methylene (-CH ₂ -), ethane-1,1-diyl (ethylidene, -CH (CH.) Optionally substituted by cyano, hydroxy, mercapto, amino or the group -C (Q ') - Z ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-1,1-diyl (propylidene,

-CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ - ), Ethene-1,2-diyl (-CH * = CH-), propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH- CH ₂ -), ethine-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i Propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each in each case optionally by cyano, Fluorine, chlorine or bromine substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or Butinylamino, each optionally by cyano, fluorine, chlorine, methyl or Ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, n, bromine, methyl, ethyl - or i-Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy Phenyl, phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenylamino, N-

Ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or N-i-propyl-N-phenyl-amino,

where the compounds 1,8-dimethyl-3- (2-oxo-2-phenyl-ethyl) -6-propyl-imidazo [1,5-d] 1,2,4] triazin-4 (3H) -one, 1,8-dimethyl-4-oxo-6-propyl-imidazo

[1, 5-d] [1, 2,4] triazine-3 (4H) -acetic acid, 1, 8-dimethyl-4-oxo-6-propyl-imidazo [1, 5-d] [1, 2 , 4] triazine-3 (4H) -acetic acid ethyl ester, 8-methyl-4-oxo-6-propyl-imidazo [l, 5-d] [l, 2,4] triazine-3 (4H) -acetic acid- ethyl ester, 8-methyl-4-oxo-imidazo [l, 5-d] [l, 2,4] triazine-3 (4H) -acetic acid ethyl ester and 4-oxo-imidazo [1, 5-d] 1 , 2,4] triazine-3 (4H) -acetic acid ethyl ester are excluded.

Compounds of formula (ID)

in which

Q ^{1 represents} O (oxygen) or S (sulfur),

Q -.2 stands for O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino,

Is ethylamino or dimethylamino,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for each optionally by cyano,

Fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for each optionally by cyano,

Hydroxy, mercapto, amino or the group -C (Q ^! ) -Z substituted methylene (-CH ₂ -), ethane-1,1-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2- diyl (dimethylene, -CH ₂ CH ₂ -), propane-1,1-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ - ), Propane-1,3-diyl (tri-methylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,2-diyl (-CH = C (CH ₃ ) -), propene-1,3-diyl (-CH = CH-CH ₂ -), ethyne-1,2-diyl or ethyne-1,3-diyl, and

Z for hydrogen, hydroxy, mercapto, amino, each in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy,

Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i- Propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i -, s- or t-butylamino, dime ylamino or diethylamino, for ethenyl, propenyl, butenyl, propenyloxy which are each optionally substituted by cyano, fluorine, chlorine or bromine, Butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, or for each optionally by nitro, cyano, hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy,

Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl, phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N-ethyl-N-phenyl-amino, N-propyl -N-phenyl-amino or Ni-propyl-N-phenyl-amino,

where the compounds 4-oxo-pyrazolo [l, 5-d] [l, 2,4] triazin-5 (4H) -acetic acid and 4-oxo-pyrazolo [l, 5-d] [l, 2, 4] triazine-5 (4H) -acetic acid methyl ester are excluded.

10. Compounds of the formula (IE)

in which

Q ^{1 represents} O (oxygen) or S (sulfur), Q ^{2 represents} O (oxygen) or S (sulfur),

R for hydrogen, cyano, fluorine, chlorine, bromine, for each methyl, ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino,

X ¹ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for each optionally by cyano,

Fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, acetyl, propionyl,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

X ² for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,

Fluorine, chlorine, bromine, or for methyl, ethyl, acetyl, propionyl, methoxy, ethoxy, methoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Ethoxycarbonyl, methylthio,

Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Y for a single bond or for methylene optionally substituted by cyano, hydroxy or the grouping -C (Q ¹ ) -Z (-

CH ₂ -), ethane-l, l-diyl (ethylidene, -CH (CH ₃ ) -), ethane-1,2-diyl (di- methylene, -CH ₂ CH ₂ -), propane-1,1-diyl (propylidene, -CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), Propane-1,3-diyl (trimethylene, -CH ₂ CH ₂ CH ₂ -), ethene-1,2-diyl (-CH = CH-), propene-1,3-diyl (- CH = CH-CH ₂ -), Ethin-1, 2-diyl or Ethin-1, 3-diyl, and

for hydrogen, hydroxy, mercapto, amino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n - or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i- Propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each optionally with cyano, fluorine , Chlorine or bromine substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or B utinylamino, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, or for each optionally by nitano .

Hydroxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy or chloroethoxy substituted phenyl, phenylcarbonyl,

Phenyloxy, phenylthio, phenylamino, N-methyl-N-phenyl-amino, N- Ethyl-N-phenyl-amino, N-propyl-N-phenyl-amino or Ni-propyl-N-phenyl-amino is.

11. A process for the preparation of compounds of the formula (I), characterized in that compounds of the formula (II)

in which

Q ² , Q ³ , Q ⁴ and R one of those specified in one of claims 1 to 5

Have meanings

with compounds of the general formula (III)

in which

Q ¹ , Y and Z have one of the meanings given in one of claims 1 to 5 and

X ^{3 represents} halogen or the grouping -YC (Q ^! ) -Z, where Y, Q ¹ and Z in turn have one of the meanings given in one of claims 1 to 5, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,

and optionally the compounds of the general formula thus obtained

(I) converted into other compounds of the general formula (I) according to the substituent definition by customary methods.

12. Composition, characterized by a content of at least one compound according to one of claims 1 to 10 and conventional extenders.

13. Use of a compound according to any one of claims 1 to 10 or an agent according to claim 12 for controlling unwanted plants.

14. A method for controlling unwanted plants, characterized in that a compound according to one of claims 1 to 10 or an agent according to claim 12 is allowed to act on the plants and / or their habitat.