DE19834110A1 - New heterocyclyl(alkyl)-substituted pyrazolyl-pyrazole derivatives, used as herbicides and plant growth regulators, especially as pre- or post-emergence selective herbicides in crops such as rice - Google Patents

Abstract

1-(3-Pyrazolyl)-5-(N-containing heterocyclyl or heterocyclylalkyl)-pyrazole derivatives (I) are new. Pyrazolyl-pyrazoles of formula (I) are new. R1 = T, 2-6C alkenyl, 2-6C alkynyl, cycloalkyl or cycloalkyl-T- (all optionally substituted by one or more halo); R2 = T, cycloalkyl, OT, ST, SOT or SO2T (all optionally substituted by one or more halo); or R1 + R2 = group completing a 5-7 membered ring, optionally substituted by one or more of halo, T and OT; T = 1-4C alkyl; R3 = H, halo or CN; or T, cycloalkyl, OT or -T-OT (all optionally substituted by one or more halo); R4 = H or electron withdrawing group; R5, R6 = H, halo or OH; or alkyl, alkoxy or alkoxyalkyl (all optionally substituted by one or more halo); or CR5R6 = 3-6 membered ring, optionally substituted by one or more of halo, T and OT; or two adjacent or non-adjacent R5 = group completing a 3-6 membered saturated ring, optionally substituted by one or more of halo, NH2, NHT, N(T)2, OH, T and OT; or two adjacent R5 = bond; or two adjacent R5 and two adjacent R6 each = bond; n = 0-3; Q = heterocyclyl containing at least one N (optionally substituted by one or more of NH2, OH, halo, NO2, CN, O, S, COOH, CHO or SO2NH2; or alkyl, mono- or dialkylamino, alkoxy, alkoxycarbonyl, alkoxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, or mono- or dialkylaminosulfonyl (all optionally substituted by one or more halo)); provided that: (a) if R5 = H, then Q is not 4,5-dihydro-2-oxazolyl or 4,5-dihydro-2-oxazolinyl; and (b) if n = 0, then Q is not dichloromaleimido, optionally substituted 3,4,5,6-tetrahydrophthalimido, optionally substituted succinimido, optionally substituted maleimido, optionally substituted 3-aza-7,10-dioxa-spiro (5.4) decan-3-yl or N-bonded 3-, 5- or 6-membered saturated or aromatic ring containing one (and only one) N and optionally one O (optionally substituted by T); unless specified otherwise alkyl moieties have 1-6C and cycloalkyl moieties 3-8C. An Independent claim is included for the preparation of (I).

Description

The invention relates to the technical field of herbicides and Plant growth regulators, especially that of herbicides for selective Control of weeds and grass weeds in crops.

From various publications it is already known that certain pyrazolylpyrazoles possess herbicidal properties. This is how WO 94/08999 and WO 98/06702 describe 1- (3-pyrazolyl) pyrazole, which is in the 5-position of the second pyrazole ring below others by succinimid-1-yl or maleimid-1-yl derivatives are substituted. From WO 97/02690 1- (3-pyrazolyl) pyrazoles are known, which in 5- Position of the second pyrazole ring including a 4,5-dihydro-2- wear oxazolyl or 4,5-dihydro-2-oxazolinyl residue. WO 97/09313 discloses 1- (3- Pyrazolyl) pyrazole, which is in the 5-position of the second pyrazole ring among others wear substituted aryl.

However, the pyrazolylpyrazoles known from these publications are used often associated with disadvantages in practice. So is the herbicidal or plant growth regulating activity of the known compounds not always sufficient, or with sufficient herbicidal activity undesirable damage to crops was observed.

The object of the present invention is to provide herbicidal and plant growth regulating compounds which are known from the prior art Technology overcome known disadvantages.

The problem is solved by heterocyclyl- and heterocyclylalkyl-substituted pyrazolylpyrazoles of the general formula (I)

wherein
R ^{1 is} C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl or C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, these five radicals optionally being substituted by one or more identical or different halogen atoms;
R ² C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, wherein these six radicals are optionally substituted by one or more identical or different halogen atoms, or
R ¹ and R ² form with the carbon atom carrying them a 5- to 7-membered saturated ring which is optionally substituted by one or more, identical or different radicals from the group halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ -Alkoxy is substituted;
R ^{3 is} hydrogen, halogen, cyano, C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, where the four latter radicals are optionally substituted by one or more identical or different halogen atoms;
R ^{4 is} hydrogen or an electron withdrawing group;
R ⁵ and R ⁶ are each independently hydrogen, halogen, hydroxy, C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, where the last three Residues are optionally substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group together with the carbon atom carrying them form a 3- to 6-membered saturated ring which may be replaced by one or more, identical or different radicals from the group halogen, C ₁ -C ₄ - alkyl and C ₁ -C ₄ alkoxy is substituted, or
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups together with the carbon atoms carrying them form a 3- to 6-membered saturated ring which may be replaced by one or more identical or different radicals from the halogen group , Amino, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, hydroxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond;
n 0, 1, 2 or 3;
Q optionally by one or more, identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) ) -amino, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, -C ₁ -C ₆ -alkylthio, C ₁ -C ₆ - alkylsulphinyl, C ₁ -C ₆ -alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ - alkyl) aminosulfonyl, wherein the twelve last-mentioned radicals are optionally substituted by one or more identical or different halogen atoms are substituted, are substituted heterocyclyl and contain at least one nitrogen atom,
with the proviso that

• a) when R ^{5 is} hydrogen, Q must not be 4,5-dihydro-2-oxazolyl or 4,5-dihydro-2-oxazolinyl, or
• b) if n is 0, Q must not be 3,4-dichloromaleimid-1-yl, in each case unsubstituted 3,4,5,6-tetrahydrophthalimid-1-yl, succinimid-1-yl, maleinimid-1-yl, 3-aza-7,10-dioxaspiro [5.4] decan-3-yl or an unsubstituted or optionally substituted by C ₁ -C ₄ alkyl 3, 5 or 6-membered, exactly one nitrogen atom and optionally containing an oxygen atom, saturated or aromatic ring, which is linked via the nitrogen atom.

Among an electron-withdrawing remnant, as in J March, is "Advanced Organic Chemistry ", 3rd Ed., John Wiley & Sons, N.Y, 1985, pages 16-18, 33-34 and 237-238 described to understand a residue, the electronegative mesomers and / or has inductive effects. Examples of such radicals are nitro, cyano, carbonyl, Ester, carboxylic acid, amide, sulfonyl, sulfonic acid and sulfamide residues.

In formula (I) and all subsequent formulas, the carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton such as alkenyl and alkynyl each be straight-chain or branched. If not specifically indicated, the lower carbon skeletons, z. B. with 1 to 6 C atoms or in the case of unsaturated groups with 2 to 4 C atoms, preferred. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl etc. mean z. B. methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, Hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl have the Significance of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl means e.g. B. allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, But-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; Alkynyl means e.g. B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl. The multiple bond can be in any position of the unsaturated residue are located.

Unless otherwise stated, cycloalkyl means a carbocyclic, saturated ring system with three to eight carbon atoms, e.g. B. cyclopropyl, cyclopentyl or cyclohexyl. In the case of composite radicals, such as (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₆ ) -alkyl, the former radical can be located at any position of the latter.

In the case of a doubly substituted amino group, such as dialkylamino, these can the two substituents may be the same or different.

Halogen means fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are partially or fully substituted alkyl, alkenyl or alkynyl, for example by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine. B. CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ , CH ₂ CH ₂ Cl; Haloalkoxy is e.g. B. OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; The same applies to haloalkenyl and other halogen-substituted radicals.

Is the carbon chain of an alkyl, alkenyl or alkynyl radical by several Interrupted heteroatoms, these heteroatoms should not be directly adjacent his.

The term heterocyclyl means a residue derived from a heterocycle understand. Unless otherwise stated, heterocycle means a complete saturated, partially saturated, unsaturated or heteroaromatic ring system, the contains one or more heteroatoms, preferably from the group oxygen, Sulfur and nitrogen. Examples include pyridine, pyrimidine, pyridazine, pyrazine, Triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, thiazole, oxazole, Pyrrole, pyrazole, imidazole, aziridine, pyrrolidine, piperidine, piperazine, morpholine and Benzothiazole. If a heterocycle contains at least two heteroatoms, then the condition is that two oxygen atoms are not directly adjacent. At these heterocycles can be linked to the other part of the molecule Compound of formula (I) basically, i. H. provided it is the structure of the ring system allowed to occur at any point on the heterocycle.

In addition to the substituents mentioned above, a heterocycle can also be one Contain oxo group, which is on a carbon or sulfur atom of the  Ring system can be. One in the ring of the heterocycle Sulfur atom can also be substituted by two oxo groups.

The compounds of general formula (I) can, depending on the type and linkage of the substituents are present as stereoisomers. For example, are one or If there are several alkenyl groups, diastereomers can occur. are for example one or more asymmetric carbon atoms present, so Enantiomers and diastereomers can occur. Stereoisomers can be released the mixtures obtained in the production by customary separation methods, obtained, for example, by chromatographic separation processes. You can also Stereoisomers by using stereoselective reactions using optical active starting materials and / or auxiliary substances are produced selectively. The invention also affects all stereoisomers and their mixtures, those of the general Formula (I) includes but is not specifically defined.

Depending on the nature of the substituents, the compounds of the general formula (I) can form salts. In the case of substituents with acidic properties, such as COOH, the hydrogen atom of the acidic group can be replaced by a cation which is suitable for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts or salts with organic amines. Salt formation can also be caused by the addition of an acid to basic substituents, such as. B. amino and alkylamino. Suitable acids for this are strong inorganic and organic acids, for example HCl, HBr, H ₂ SO ₄ or HNO ₃ . Such salts are also the subject of the invention.

If a radical is substituted several times, this means that at least two and maximally all hydrogen atoms of these residues by identical or different ones other radicals are substituted. The possible combinations of the different Substituents of the general formula (I) are to be understood so that the general Principles of the structure of chemical compounds must be observed, d. H. that not Compounds are formed which the person skilled in the art knows that they are chemical are unstable or not possible.  

Preferred compounds of the general formula (I) are those in which
R ¹ C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₈ cycloalkyl-C ₁ - C ₄ alkyl, these four radicals optionally being substituted by one or several, identical or different halogen atoms are substituted;
R ² C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, where these six radicals are optionally substituted by one or more identical or different halogen atoms;
R ^{3 is} hydrogen, halogen, cyano, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the two latter radicals optionally being substituted by one or more identical or different halogen atoms;
R ^{4 is} hydrogen, nitro, cyano, C (X) YR ⁷ , C (X) NR ⁸ R ⁹ , C (X) R ⁷ , SO ₂ R ⁷ , SO ₂ OR ⁷ or SO ₂ NR ⁸ R ⁹ ;
R ⁵ and R ^{6 are} each independently of one another hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ - C ₆ alkoxy or C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, the three latter radicals optionally are substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group together with the carbon atom carrying them form a 3- to 6-membered saturated ring, which may be replaced by up to four identical or different radicals from the group halogen, hydroxy, C ₁ - C ₄ alkyl and C ₁ -C ₄ alkoxy is substituted;
R ^{7 is} hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the four latter radicals being optionally by one or more, identical or different Residues from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, cyano or halogen are substituted, and the carbon chain of these four residues mentioned being optionally substituted by one or more, identical or different heteroatoms from the group consisting of oxygen and sulfur is interrupted;
R ⁸ , R ⁹ each independently of one another are hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the four last-mentioned radicals optionally being substituted by a or more, identical or different radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl or halogen are substituted, and the carbon chain of these four radicals optionally being substituted by one or more, identical or different heteroatoms from the Group oxygen and sulfur is interrupted;
Q optionally by one or more, identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) ) -amino, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ - alkylthio, C ₁ -C ₆ - alkylsulphinyl, C ₁ -C ₆ -alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ - alkyl) aminosulfonyl, wherein the twelve last-mentioned radicals optionally substituted by one or several, identical or different halogen atoms are substituted, substituted heterocyclyl which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur;
X and Y each independently represent oxygen or sulfur.

Preference is also given to compounds of the general formula (I) in which
R ¹ and R ² with the carbon atom carrying them form a 5- to 7-membered saturated ring which may be replaced by one or two identical or different radicals from the group halogen, C ₁ -C ₄ -alkyl and C ₁ -C ₄ - Alkoxy is substituted.

Also preferred are compounds of general formula (I), wherein
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups together with the carbon atoms carrying them form a 3 to 6-membered saturated ring which may be substituted by up to four identical or different radicals from the group halogen, Amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, hydroxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond.

In addition, compounds of the general formula (I) are preferred in which
R ⁸ and R ⁹ together with the nitrogen atom carrying them form a 3-, 5- or 6-membered saturated, partially saturated or completely unsaturated ring, optionally substituted by up to four methyl groups, in which case one carbon atom is optionally replaced by an oxygen atom.

Compounds of the general formula (I) in which
R ^{1 is} C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl or C ₃ -C ₆ cycloalkyl, these three radicals optionally being substituted by up to five identical or different halogen atoms;
R ² C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ - C ₄ -alkylsulfonyl, these five radicals optionally being replaced by bis are substituted to five identical or different halogen atoms;
R ^{3 is} halogen, cyano or C ₁ -C ₄ alkyl, the latter radical optionally being substituted by up to five identical or different halogen atoms;
R ⁴ nitro, cyano, C (X) YR ⁷ , C (X) NR ⁸ R ⁹ or C (X) R ⁷ ;
R ⁵ and R ⁶ are each independently hydrogen, halogen, hydroxy, C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ -alkoxy-C ₁ -C ₂ alkyl, where the last three Residues are optionally substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group, together with the carbon atom carrying them, form a 3-, 5 or 6-membered saturated ring which is optionally substituted by up to four identical or different radicals from the group halogen, C ₁ -C ₂ alkyl and C ₁ -C ₂ alkoxy is substituted;
R ^{7 is} hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -alkynyl, the three latter radicals optionally being substituted by up to four identical or different radicals from the group C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkoxycarbonyl, cyano or halogen are substituted, and wherein the carbon chain of these four radicals mentioned is optionally interrupted by a heteroatom from the group consisting of oxygen and sulfur;
R ⁸ , R ⁹ each independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -alkynyl, the four last-mentioned radicals optionally being replaced by bis are substituted to four identical or different radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl or halogen, and the carbon chain of these four radicals mentioned being optionally substituted by one or two identical or different heteroatoms from the group oxygen and sulfur is interrupted;
Q optionally by up to three identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) -amino, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio , C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ alkyl) - aminosulfonyl, wherein the twelve last-mentioned radicals are optionally substituted by up to three identical or different halogen atoms are substituted, substituted heterocyclyl, which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur;
X oxygen or sulfur and
Y oxygen
mean.

Compounds of the general formula (I) in which
R ¹ and R ² with the carbon atom carrying them form a 5- or 6-membered saturated ring which may be replaced by one or two identical or different radicals from the group halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ - Alkoxy is substituted.

Likewise, particular preference is given to compounds of the general formula (I) in which R ^{4 is} SO ₂ R ⁷ or SO ₂ NR ⁸ R ⁹ .

Likewise particularly preferred are compounds of the general formula (I) in which
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups together with the carbon atoms carrying them form a 3, 5 or 6-membered saturated ring which, if appropriate, consists of up to four identical or different radicals from the Halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy group is substituted, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond.

In addition, compounds of the general formula (I) are particularly preferred in which
R ⁸ and R ⁹ together with the nitrogen atom carrying them form a 3-, 5- or 6-membered saturated, partially saturated or completely unsaturated ring which may be substituted by up to two methyl groups and in which a carbon atom may be replaced by an oxygen atom.

Compounds of the general formula (I) in which
R ¹ C ₁ -C ₄ alkyl;
R ^{2 is} C ₁ -C ₃ alkyl, C ₁ -C ₃ alkylthio, C ₁ -C ₃ alkylsulfinyl, C ₁ -C ₃ alkylsulfonyl or C ₁ -C ₃ alkoxy, these radicals optionally being substituted by up to five identical or different halogen atoms from the group fluorine and chlorine are substituted;
R ³ bromine or chlorine;
R ⁴ nitro, cyano or CSNH ₂ ;
R ⁵ and R ⁶ each independently of one another are hydrogen, fluorine, bromine, chlorine, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, the three latter radicals optionally being substituted by up to five identical or different halogen atoms;
Q optionally by up to three identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) -amino, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio , C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, aminosulfonyl, C ₁ -C ₄ alkylaminosulfonyl, di- (C ₁ -C ₄ alkyl) - aminosulfonyl, wherein the twelve last-mentioned radicals are optionally substituted by up to three identical or different halogen atoms are substituted, substituted heterocyclyl which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur.

Compounds of the general formula (1) in which
R ¹ and R ² together form a - (CH ₂ ) ₃ - or - (CH ₂ ) ₄ group.

The present invention also relates to processes for the preparation of the compounds of the general formula (I). The compounds of the invention can be prepared, for example, in such a way that

• a) in the case of n = 0 or 1
  a compound of the formula (II),
  in which R ¹ , R ² , R ³ and R ^{4 have} the meanings given in the general formula (I) and X denotes a leaving group, such as chlorine, bromine or methylsulfonyl, with a compound of the general formula (III),
  QH (III)
  wherein Q represents a heterocyclic radical which carries an acidic hydrogen atom on a nitrogen atom, is reacted in the presence of a base and optionally a catalyst;
• b) in the case of n = 0
  a compound of the general formula (IV),
  in which R ¹ , R ² and R ^{3 have} the meanings given in the general formula (I), with a compound of the general formula (V),
  in which R ⁴ and Q have the meanings given in the general formula (I) and B represents the groups OR or NRR ', where R and R' independently of one another can be C ₁ -C ₄ -alkyl;
• c) in the case of n = 2
  a compound of the general formula (VI),
  in which R ¹ , R ² , R ³ and R ^{4 have} the meanings given in the general formula (I), with a compound of the general formula (VII),
  in which R ⁵ and Q have the meanings given in the general formula (I) and Hal represents Cl or Br, in the presence of a suitable base, such as, for example, alkali metal hydrides, or alkyl lithium compounds;
• d) in the case of n = 3
  as indicated in Scheme 1, a compound of formula (VIII) reductively into a compound of formula (IX), this by halogen exchange into a compound of formula (X) and this finally by base-catalyzed reaction with a heterocyclic compound of formula (III) in a compound of formula (XI) is transferred.

Scheme 1

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ and Q therein have the meanings given in the general formula (I) and Hal represents chlorine and bromine.

The compounds of the general formula (II) used as starting materials are known for example from WO 94/08999.

Compounds of the formula (III) are known in principle and are commercially available or can be produced by customary methods known to the person skilled in the art. As Catalysts for the reaction with compounds of the formula (II) are suitable for example Cu (I) salts such as Cul, CuBr and CuCl. As bases are suitable other alkali carbonates, such as sodium carbonate, metal alcoholates, such as Sodium ethanolate, and alkali hydrides such as sodium hydride.

Compounds of the general formula (IV) are also known and described for example in EP-A 0 643 700. General connections Formula (V) are accessible, for example, according to scheme 2:

Scheme 2

Reaction of compounds of the general formula (XII), in which R ¹⁰ denotes alkyl, which are commercially available or obtainable by those skilled in the art, with acetonitrile in the presence of a suitable base, such as, for example, alkali metal alcoholates (sodium ethanolate), gives the compounds of the general formula (XIII). The compounds of the general formula (XIV) are obtained by reaction with trialkyl formic acid orthoesters or dialkylformamide dialkyl acetals.

Compounds of the general formula (VI) are also known in principle. Your Production is described for example in WO 94/08999. Connections of the General formula (VII) are commercially available or can be found in the literature Methods, see in addition, for example, Organikum, 16th edition, Deutscher Verlag der Sciences, Berlin 1986, p. 203.

Compounds of the general formula (VIII) are known in principle and will be described for example in DE-A 196 23 892 or can according to there specified processes can be produced. Implementation of connections of the general formula (VIII) with reducing agents such as lithium aluminum hydride or Diisobutylaluminum hydride analogous to that, for example, in Synthesis, 1975, p. 617 and J. Org. Chem. 1987, 52, p. 2337 provides the compounds of the general formula (IX). Implementation of the compounds (X) by Halogenation also takes place according to methods known from the literature, such as described in Tetrahedron Lett. 1989, 30, p. 557, and Liebig's Annalen der Chemie, 1930, p. 211. The subsequent reaction with a heterocyclic Compound of general formula (III) in the presence of a base, such as Alkali metal hydroxides, alkali metal carbonates, alkali or alkaline earth metal alcoholates or alkali metal hydrides analogous to that described in Synthesis, 1981, p. 124 Method provides the compounds of the general formula (XI).

In the above-mentioned base-catalyzed reactions, in addition to the In general, inorganic bases mentioned, such as triethylamine or 1,8-diazabicylco [5.4.0] undec-7-ene (DBU) can be used. The respective Base is used, for example, in the range from 0.1 to 3 molar equivalents. The base-catalyzed reactions are preferably carried out in an inert organic solvents, such as. B. tetrahydrofuran (THF), dioxane, acetonitrile, Dimethylformamide (DMF), methanol and ethanol, at temperatures between -10 ° C and the boiling point of the solvent, preferably at 20 ° C to 60 ° C. If Acid addition salts compound of formula (III) are used, this is set usually free in situ with the help of a base.  

With the "inert" designated in the above process variants Solvents "are solvents that are meant under the respective Reaction conditions are inert, but not under any Reaction conditions must be inert.

The compounds of formula (I) according to the invention have an excellent herbicidal activity against a wide range of economically important mono- and dicotyledonous harmful plants. Perennial weeds that are difficult to control, which sprout from rhizomes, rhizomes or other permanent organs well grasped by the active ingredients. It is usually irrelevant whether the Substances applied by pre-sowing, pre-emergence or post-emergence become. Some representatives of mono- and dicotyledons are examples Weed flora called, controlled by the compounds of the invention can be, without being limited to certain by the naming Species should be done. On the side of the monocot weed species, e.g. B. Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on the part of the perennial species agropyron, Cynodon, Imperata as well as sorghum and perennial Cyperus species well recorded. In dicotyledon weed species, the spectrum of activity extends to species such as: B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia in the perennial weeds. Among the specific Culture conditions occurring in rice harmful plants such. B. Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are from the Active ingredients according to the invention also fought excellently.

Are the compounds of the invention prior to germination on the Applied earth surface, so is either the emergence of the weed seedlings completely prevented or the weeds grow up to the cotyledon stage, however, they stop growing and eventually die after three up to four weeks. When applying the active ingredients to the green ones Plant parts in the post-emergence process also occur very quickly after treatment a drastic growth stop and the weed plants stay in the for  At the time of application, the growth stage is present or will die a certain time, so that in this way one for the crops harmful weed competition is eliminated very early and sustainably.

Although the compounds of the invention are excellent herbicidal Have activity against mono- and dicotyledon weeds Cultivated plants of economically important crops such as B. wheat, barley, rye, Rice, corn, sugar beet, cotton and soy barely or not at all damaged. The present compounds are very suitable for these reasons good for selective control of undesirable plant growth in agricultural crops or in ornamental crops.

Because of their herbicidal and plant growth regulatory properties the active ingredients can also be used to control harmful plants in crops of known or still to be developed genetically modified plants be used. The transgenic plants are usually characterized by special advantageous properties, for example by resistance resistance to certain pesticides, especially certain herbicides against plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. B. the crop in terms of quantity, Quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or changed starch quality or known with a different fatty acid composition of the crop.

Preference is given to using the compounds of the formula (I) according to the invention or their salts in economically important transgenic cultures of crops and Ornamental plants, e.g. B. of cereals such as wheat, barley, rye, oats, millet, rice, Cassava and corn or crops of sugar beet, cotton, soybeans, rapeseed, Potato, tomato, pea and other vegetables. Preferably, the Compounds of formula (I) used as herbicides in crops become resistant to the phytotoxic effects of herbicides are or have been made genetically resistant.  

Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described

• - genetic engineering of crops for the purpose of modifying the in starch synthesized in plants (e.g. WO 92/11376, WO 92/14827 WO 91/19806),
• - Transgenic crop plants which are active against certain herbicides of the type Glufosinate (see e.g. EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-501 3659) are resistant,
• - Transgenic crops, for example cotton, with the ability Bacillus thuringiensis toxins (Bt toxins) which the plants produce make resistant to certain pests (EP-A-01 42924, EP-A-01 93259).
• - Transgenic crop plants with a modified fatty acid composition (WO 91/13972).

Numerous molecular biological techniques that new transgenic plants use modified properties can be produced are known in principle; see e.g. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science "1 (1996) 423-431).

For such genetic engineering manipulations, nucleic acid molecules in Plasmids are introduced that have a mutagenesis or a sequence change allow by recombination of DNA sequences. With the help of the above Standard procedures can e.g. B. base changes made, partial sequences removed or natural or synthetic sequences added. For the Connection of the DNA fragments to one another can be made to the fragments adapters or linker.  

The production of plant cells with a reduced activity of one The gene product can be achieved, for example, by expression at least a corresponding antisense-RNA, a sense-RNA to achieve a Cosuppression effect or the expression of at least one accordingly constructed ribozyme that specifically transcripts the above Gene product splits.

On the one hand, DNA molecules can be used that cover the entire coding sequence of a gene product including any that are present flanking sequences include, as well as DNA molecules that are only parts of the encoding sequence, these parts must be long enough to be in to cause the cells an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coding Have sequences of a gene product, but are not completely identical.

In the expression of nucleic acid molecules in plants, the synthesized Protein can be located in any compartment of the plant cell. Around but to reach the localization in a certain compartment can e.g. B. the coding region can be linked to DNA sequences that localize in guarantee a certain compartment. Such sequences are Known to those skilled in the art (see for example Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85: 846-850 (1988); Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be whole according to known techniques Plants are regenerated. In principle, the transgenic plants can are plants of any plant species, d. H. both monocotyledon also dicotyledonous plants.

In this way, transgenic plants can be obtained that have changed properties Overexpression, suppression or inhibition of homologous (= natural) genes or Gene sequences or expression of heterologous (= foreign) genes or gene sequences exhibit.  

The compounds according to the invention can preferably be used in transgenic cultures used against herbicides from the group of sulfonylureas, Glufosinate-ammonium or Glyphosate-Isopropylammonium and similar Active ingredients are resistant.

When using the active compounds according to the invention in transgenic cultures in addition to the effects observed in other cultures Harmful plants often have effects on the application in the respective transgenic culture are specific, for example a modified or special expanded weed spectrum that can be controlled has changed Application rates that can be used for the application, preferably good combinability with the herbicides against which the transgenic culture is resistant, as well as influencing the growth and yield of the transgenic Crops.

The invention therefore also relates to the use of Compounds according to the invention as herbicides for controlling Harmful plants in transgenic crops.

In addition, the substances according to the invention have excellent properties growth regulatory properties in crops. You grab regulate in the plant's own metabolism and can thus be targeted Influencing plant ingredients and to facilitate harvesting such. B. by Triggering desiccation and stunted growth can be used. Furthermore they are also suitable for the general control and inhibition of undesired vegetative growth without killing the plants. An inhibition of the Vegetative growth plays a major role in many mono- and dicotyledon crops Role, as this can reduce or completely prevent storage.

The invention also relates to herbicides and plant growth regulators Agents containing compounds of formula (I). The invention Compounds can be in the form of customary formulations known to the person skilled in the art,  such as wettable powders, emulsifiable concentrates, sprayable solution, dusts or granules can be used.

The compounds of formula (I) can be formulated in different ways, depending on according to which biological and / or chemical-physical parameters are specified. Examples of possible formulations are: Wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water in-oil emulsions, sprayable solutions, suspension concentrates (S C), Dispersions based on oil or water, oil-miscible solutions, Capsule suspensions (CS), dusts (DP), pickling agents, granules for the litter and floor application, granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble Granules (SG), ULV formulations, microcapsules and waxes. This individual Formulation types are known in principle and are described for example in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th edition 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, Solvents and other additives are also known and will be described for example in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers ", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen," Introduction to Clay Colloid Chemistry "; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden," Solvents Guide "; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual ", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood," Encyclopedia of Surface Active Agents ", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt "Surface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Spray powders are preparations which are uniformly dispersible in water Active substance in addition to a diluent or an inert substance, also ionic and / or surfactants  non-ionic type (wetting agent, dispersing agent), e.g. B. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols polyoxethylated fatty amines, Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltauric acid sodium contain. The herbicidal active ingredients are used to produce the wettable powders for example in conventional equipment such as hammer mills, fan mills and Air jet mills finely ground and simultaneously or subsequently with the Formulation aids mixed.

Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures the organic solvent with the addition of one or more surfactants ionic and / or nonionic type (emulsifiers). As emulsifiers can be used for example: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as z. Sorbitan fatty acid esters or polyoxethylene sorbitan esters such as. B. Polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays, such as kaolin, bentonite and pyrophyllite, or Diatomaceous earth.

Suspension concentrates can be water or oil based. You can for example by wet grinding using commercially available pearl mills and optionally addition of surfactants, such as. B. above with the others Formulation types already listed can be produced.

Emulsions e.g. B. oil-in-water emulsions (EW) can be used, for example Stirrers, colloid mills and / or static mixers using  aqueous organic solvents and optionally surfactants such as z. B. already listed above for the other formulation types.

Granules can either be sprayed onto the adsorbable, granulated inert material or by applying Active ingredient concentrates by means of adhesives, e.g. B. polyvinyl alcohol, polyacrylic acid Sodium or mineral oils on the surface of carriers such as sand, Kaolinite or granulated inert material. Suitable active ingredients can also in the usual way for the production of fertilizer granules - if desired in a mixture with fertilizers - granulated.

Water-dispersible granules are generally made using the customary methods such as spray drying, fluidized bed granulation, plate granulation, mixing with High speed mixers and extrusion made without solid inert material.

For the production of plate, fluidized bed, extruder and spray granules see e.g. B. Procedure in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook ", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For more details on the formulation of crop protection products see e.g. B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook," 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations generally contain 0.1 to 99% by weight in particular 0.1 to 95 wt .-%, active ingredient of formula (I).

In wettable powders, the active ingredient concentration is e.g. B. about 10 to 90 wt .-% of The remainder to 100 wt .-% consists of conventional formulation components. At emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt .-%. Dusty formulations contain 1 up to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight Active ingredient. In the case of water-dispersible granules, the active ingredient content depends in part  depends on whether the active compound is liquid or solid and which Granulation aids, fillers, etc. can be used. With those in water dispersible granules, the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned may each contain usual adhesive, wetting, dispersing, emulsifying, penetration, preservation, Antifreeze and solvents, fillers, carriers and dyes, defoamers, Evaporation inhibitors and agents that affect pH and viscosity.

Based on these formulations, combinations with others can also be made pesticidal substances, such as. B. insecticides, acaricides, herbicides, Fungicides, as well as with safeners, fertilizers and / or growth regulators produce, e.g. B. in the form of a finished formulation or as a tank mix.

As a combination partner for the active compounds according to the invention in mixture formulations or in the tank mix, it is possible, for example, to use known active compounds, such as those described, for example, in US Pat. B. in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 1997 and the literature cited therein. As known herbicides, which can be combined with the compounds of formula (I), z. For example, the following active substances are to be named (note: the compounds are identified either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name, possibly together with a usual code number):
acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylates; cafenstrole (CH-900); carbetamide; cafentrazone (ICI-A0051); CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie 2-chloroallyl ester of diethyldithiocarbamic acid; chlomethoxyfen; chloramben; chlorazifop-butyl, chloromesulone (ICI-A0051); chlorbromuron; chlorobufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chloronitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlororthal dimethyl; chlorothiamide; cinmethylin; cinosulfuron; clethodim; clodinafop and its ester derivatives (e.g. clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g. butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop and its esters such as diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, clomazone; dimethipin; dimetrasulfuron, dinitramine dinoseb; dinoterb; diphenamide; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F523 1, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] phenyl] ethanesulfonamide; ethoxyfen and its esters (e.g. ethyl ester, HN-252); etobenzanide (HW 52); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, e.g. B. fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P and their esters, e.g. B. fluazifop-butyl and fluazifop-P-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (e.g. pentyl ester, S-23031); flumioxazin (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen fluoroglycofen-ethyl; flupropacil (UBIC-4243); fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosafen; halosulfuron and its esters (e.g. methyl ester, NC-319), haloxyfop and its esters, haloxyfop-P (= R-haloxyfop) and its esters, hexazinone; imazamethabenz-methyl, imazapyr, imazaquin and salts such as the ammonium salt, imazethamethapyr, imazethapyr, imazosulfuron, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxapyrifop, karbutilate, lactofen, CPM, lenacilacid, linacilon, MCP, linacilacid, linacil, CPA , metamitron, metazachlor, methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitraline; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenisopham; phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-1 52005); prynachlor; pyrazolinates; pyrazone; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; pyrithiobac (KIH-2031); pyroxofop and its esters (e.g. propargyl esters); quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives z. B. quizalofop-ethyl; quizalofop-P-tefuryl and ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] - 4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; sulfentrazone (FMC-97285, F-6285); sulfazuron sulfometuron-methyl; sulfosate (ICI-A0224); TCA; tebutam (GCP-5544); tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (e.g. methyl ester, DPX-66037); trimeturon; vernolate; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1H-tetrazole, UBH-509, D-489, LS 82-556, KPP-300, NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

The formulations available in commercial form are used optionally diluted in the usual manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, ground or scatter granules as well as sprayable Solutions are usually no longer mixed with other inert solutions before use Diluted substances.

With the external conditions such as temperature, humidity, the type of herbicide used, u. a. the required application rate varies Compounds of formula (I). It can fluctuate within wide limits, e.g. B. between 0.001 and 10.0 kg / ha or more of active substance, preferably it is however between 0.005 and 5 kg / ha.

The following examples illustrate the invention.

A. Chemical examples A.1 Preparation of 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (4- methylpyrazol-1-yl) -1H-pyrazol-4-carbonitrile (Example No. 37 in Table 1)

1.50 g (4.3 mmol) 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5-bromo-1H- pyrazole-4-carbonitrile are dissolved in 1 ml of dimethylformamide. With stirring 646 mg (4.7 mmol, 1.1 equivalents) potassium carbonate and 81 mg (0.4 mmol, 0.1 Equivalent copper iodide added. A solution of 524 mg (6.4 mmol, 1.5 equivalents) of 4-methylpyrazole in 10 ml of dimethylformamide dripped. The mixture is then heated under reflux for 5 hours, to room temperature cooled and the dimethylformamide removed in vacuo. The backlog will partitioned between 50 ml of ethyl acetate and 50 ml of water and the phases separated. The organic phase is washed twice with 30 ml of water. After drying with Magnesium sulfate, the solvent is removed in vacuo and the residue Chromatograph silica gel with heptane / ethyl acetate 4: 1. 280 mg (0.8 mmol, 18% of theory) 1- (4-chloro-5-difluoromethoxy-1methyl-pyrazol-3-yl) -5- (4- methylpyrazol-1-yl) -1H-pyrazol-4-carbonitrile as a colorless oil.  

A.2 Preparation of 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (pyrazole- 1-yl-methyl) -1H-pyrazole-4-carbonitrile (Example No. 1 in Table 2)

0.70 g (1.7 mmol) 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5-chloromethyl- 1H-pyrazole-4-carbonitrile is dissolved in 10 ml of dimethylformamide. To do this 232 mg (3.4 mmol, 2.0 equivalents) of pyrazole and 942 mg (6.8 mmol, 4.0 equivalents) of potassium carbonate. The mixture is left at room temperature for 6 hours stir and then partition between 100 ml of methylene chloride and 100 ml of water. The Phases are separated and the aqueous phase is washed twice with 50 ml each Extracted methylene chloride. After drying with magnesium sulfate, this becomes Solvent removed in vacuo and the residue by chromatography Silica gel cleaned with heptane / ethyl acetate 2: 1. 500 mg (1.2 mmol, 74% of theory) 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (pyrazol-1-yl methyl) -1H-pyrazole-4-carbonitrile as a colorless oil.

A.3 Preparation of 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (pyridine- 2-yl) -1H-pyrazole-4-carbonitrile (Example No. 69 in Table 1) A.3.1 Preparation of 3-dimethylamino-2- (pyridin-2-yl) carbonyl-propenonitrile

1.55 g (66.1 mmol) sodium are added to 35 ml ethanol. You leave as long Stir until the sodium has completely dissolved and then remove that Solvent in a vacuum. The residue is suspended in 70 ml of toluene and in addition at room temperature 10.0 g (66.1 mmol) ethyl 2-picolinate, 2.67 g (66.1 mmol) acetonitrile dissolved in 50 ml of toluene added dropwise. The mixture is refluxed for 6 hours heated, cooled to room temperature and the orange colored solid filtered off. After dissolving the solid in 40 ml of dimethylformamide dimethyl acetal, 3 ml Acetic acid added and stirred for 20 hours at room temperature. The mixture is then partitioned between 200 ml of water and 200 ml of ethyl acetate and the phases Cut. The aqueous phase is extracted with 75 ml of ethyl acetate and the combined organic phases dried with magnesium sulfate. The solvents are in Vacuum removed and the raw product directly implemented. 3.56 g are obtained  (17.7. Mmol, 27%) 3-dimethylamino-2- (pyridin-2-yl) -carbonyl-propenonitrile as yellow oil.

A.3.2 Conversion to 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (pyridin-2- yl) -1H-pyrazole4-carbonitrile

1.4 g (6.9 mmol) of 4-chloro-5-difluoromethoxy-3-hydrazino-1-methyl-pyrazole are in 20 ml ethanol dissolved and with stirring 1.5 g (6.9 mmol, 1 equivalent) 3- Dimethylamino-2- (pyridin-2-yl) carbonyl-propenonitrile added. The solution is heated under reflux for 1.5 hours, concentrated in vacuo and the residue Chromatograph silica gel with heptane / ethyl acetate 2: 1. 1.4 g (4.0 mmol, 58% of theory) 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- (pyridin-2- yl) -1H-pyrazole-4-carbonitrile with a fixed point of 98 ° C.

A.4 Preparation of 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- [2- (pyridin-2-yl) ethenyl] -1H-pyrazol4-carbonitrile (Example No. 41 in Table 3)

A mixture of 1.3 g (3.0 mmol) of 2-picolyltriphenylphosphonium chloride and Sodium hydride is dissolved in 10 ml of tetrahydrofuran and cooled to -78 ° C. To 1.0 g (3.3 mmol) of 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) -5- formyl-1H-pyrnzol-t-carbonitrile. Leave on within 7 hours Come to room temperature and stir for 3 days. After that, the reaction is through Addition of 80 ml of saturated ammonium chloride solution ended. The aqueous phase is extracted 3 times with 60 ml of ethyl acetate and the combined organic Phases dried with magnesium sulfate. After removing the solvent in the The residue is purified in vacuo on silica gel with heptane / ethyl acetate 1: 3. Man receives 0.76 g (67% of theory) 1- (4-chloro-5-difluoromethoxy-1-methyl-pyrazol-3-yl) - 5- [2- (pyridin-2-yl) ethenyl] -1H-pyrazol-4-carbonitrile with a fixed point of 107 to 111 ° C.  

The examples listed in the following tables were analogous above mentioned methods are produced or are analogous to those mentioned above Methods available.

The abbreviations used in the tables mean:
Bu = butyl,
Et = ethyl,
Me = methyl,
Pr = propyl,
c = cyclo,
i = so,
s = secondary,
t = tertiary,
Mp. = Fixed point.

Table 1

Compounds of the general formula (I) with n = 0

Table 2

Compounds of the general formula (I) with n = 1

Table 3

Compounds of the general formula (I) with n = 2 or 3

B. Examples of formulation B.1 dusts

A dusting agent is obtained by mixing 10 parts by weight of a compound of the general formula (I) and 90 parts by weight of talc as an inert substance and mixed in one Crushed crushing mill.

B.2 Dispersible powder

A wettable powder which is easily dispersible in water is obtained by 25 parts by weight of a compound of general formula (I), 64 parts by weight kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 Mixes parts by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and grind in a pin mill.

B.3 Dispersion concentrate

A dispersion concentrate which is easily dispersible in water is obtained by 20 parts by weight of a compound of the general formula (I), 6 parts by weight Alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (Boiling range e.g. approx. 255 to above 277 ° C) mixes and in a friction ball mill a fineness of less than 5 microns is ground.

B.4 Emulsifiable concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 Parts by weight of oxyethylated nonylphenol as an emulsifier.

B.5 Water-dispersible granules

A water-dispersible granulate is obtained by:
75 parts by weight of a compound of the general formula (I),
10 parts by weight of calcium lignosulfonate,
5 parts by weight of sodium lauryl sulfate,
3 parts by weight of polyvinyl alcohol and
7 parts by weight of kaolin
mixes, grinds on a pin mill and granulates the powder in a fluidized bed by spraying water as granulating liquid.

A water-dispersible granulate is also obtained by
25 parts by weight of a compound of the general formula (I),
5 parts by weight of 2,2'-dinaphthylmethane-6,6'disulfonic acid sodium
2 parts by weight of sodium oleoylmethyl taurine,
1 part by weight of polyvinyl alcohol,
17 parts by weight of calcium carbonate and
50 parts by weight of water
homogenized on a colloid mill and pre-comminuted, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.

C. Biological examples C.1 Pre-emergence weed action

Seeds of monocotyledonous and dicotyledonous weed plants are grown in sandy pots in cardboard pots Clay soil laid out and covered with earth. The in the form of wettable powders or emulsion concentrates formulated compounds according to the invention then as an aqueous suspension or emulsion with a water application rate of converted 600 to 800 l / ha in different dosages on the surface the covering earth is applied. After the treatment, the pots are in the greenhouse set up and kept under good growth conditions for the weeds. The optical assessment of the damage to the plants or the emergence occurs after the emergence of the Test plants after a test period of 3 to 4 weeks compared to untreated controls. As the test results show, the Compounds according to the invention have a good herbicidal pre-emergence activity a wide range of grasses and weeds. Show for example the compounds of Examples Nos. 28, 31, 37, 42 and 57 from Table 1 and compounds of Examples 1, 40, 50, 51, 70, 73, 77, 80, 81, 83, 84, 89, 90 and 91 from Table 2 very good herbicidal activity against harmful plants such as  Stellaria media, Amaranthus retroflexus, Sinapis arvensis, Avena fatua, Lolium multiflorum and Setaria viridis at a rate of 3.0 kg or even significantly less active substance per hectare.

C.2 Post-emergence weed action

Seeds of monocotyledonous and dicotyledonous weeds are grown in cardboard pots in sandy Clay soil laid out, covered with earth and in the greenhouse under good ones Growth conditions attracted. Two to three weeks after sowing the test plants are treated in three-leaf study. The as wettable powder or compounds of the invention formulated as emulsion concentrates are in different dosages with a water application rate of the equivalent of 600 to 800 l / ha sprayed on the green parts of the plant. After 3 to 4 Weeks of the test plants in the greenhouse under optimal Growth conditions will compare the effect of the preparations untreated controls rated. The agents according to the invention also have Post-emergence good herbicidal activity against a wide range economically important grasses and weeds. For example, the Compounds of Examples Nos. 28, 31, 37, 42 and 57 from Table 1 as well Compounds of Examples Nos. 40, 41, 51, 69, 73, 74, 76, 79, 83, 85, 87, 91 and 95 from Table 2 very good herbicidal activity against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapis arvensis, Avena fatua, Lolium multiflorum and Setaria viridis at a rate of 3.0 kg or significantly less Active ingredient per hectare.

C.2 Effect on harmful plants in rice

Typical harmful plants in rice crops such as Echinocloa crus galli and Cyperus iria in the greenhouse under paddy rice conditions (water retention level: 2-3 cm). After the treatment, the test plants are grown in the Greenhouse set up under optimal growing conditions and during the kept for the entire test period. It takes about three weeks after application the evaluation by means of an optical assessment of the plant damage in comparison to untreated controls. The compounds of the invention have very good ones herbicidal activity against harmful plants. For example, the  Compounds of Examples Nos. 37, 42, 45 and 57 from Table 1 and compounds of Examples Nos. 1, 50, 69, 70, 74, 77, 79, 81, 84, 85, 87, 89, 90 and 95 from Table 2 very good herbicidal activity against harmful plants such as Cyperus iria and Echinocloa crusgalli with an application rate of 3.0 kg or clearly less active ingredient per hectare. .

C.3 Compatibility with crops

In further experiments in the greenhouse, seeds of a larger number of Cultivated plants and weeds laid out in sandy loam soil and with soil covered. Part of the pots are immediately as described in Section 1 treated, the rest set up in the greenhouse until the plants two to three have developed real leaves and then with the Substances of the formula (I) according to the invention in different dosages sprayed. Four to five weeks after application and standing in the greenhouse it is determined by means of an optical rating that the compounds according to the invention dicotyledonous cultures such as B. Soy and sugar beet in the fore and Post-emergence process undamaged or even at high doses of active ingredient leave almost undamaged. Some substances also protect Gramineae crops such as B. barley, wheat and rice. The connections of the Formula (I) partially show a high selectivity and are therefore suitable for Control of unwanted plant growth in agricultural crops.

Claims (11)

1. Heterocyclyl- and heterocyclylalkyl-substituted pyrazolylpyrazoles of the general formula (I),
wherein
R ^{1 is} C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl or C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, these five radicals optionally being substituted by one or more identical or different halogen atoms;
R ² C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, wherein these six radicals are optionally substituted by one or more identical or different halogen atoms, or
R ¹ and R ² form with the carbon atom carrying them a 5- to 7-membered saturated ring which is optionally substituted by one or more, identical or different radicals from the group halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ -Alkoxy is substituted;
R ^{3 is} hydrogen, halogen, cyano, C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, where the four latter radicals are optionally substituted by one or more identical or different halogen atoms;
R ^{4 is} hydrogen or an electron withdrawing group;
R ⁵ and R ⁶ are each independently hydrogen, halogen, hydroxy, C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, where the last three Residues are optionally substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group together with the carbon atom carrying them form a 3- to 6-membered saturated ring which may be replaced by one or more, identical or different radicals from the group halogen, C ₁ -C ₄ - alkyl and C ₁ -C ₄ alkoxy is substituted, or
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups together with the carbon atoms carrying them form a 3- to 6-membered saturated ring which may be replaced by one or more identical or different radicals from the halogen group , Amino, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, hydroxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond;
n 0, 1, 2 or 3;
Q optionally by one or more, identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) ) -amino, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ - alkylthio, C ₁ -C ₆ - alkylsulphinyl, C ₁ -C ₆ -alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ - alkyl) aminosulfonyl, wherein the twelve last-mentioned radicals optionally substituted by one or several, identical or different halogen atoms are substituted, are substituted heterocyclyl and contain at least one nitrogen atom,
with the proviso that

• a) when R ^{5 is} hydrogen, Q must not be 4,5-dihydro-2-oxazolyl or 4,5-dihydro-2-oxazolinyl, or
• b) if n is 0, Q must not be 3,4-dichloromaleimid-1-yl, in each case unsubstituted 3,4,5,6-tetrahydrophthalimid-1-yl, succinimid-1-yl, maleinimid-1-yl, 3-aza-7,10-dioxaspirn [5.4] decan-3-yl or an unsubstituted or optionally substituted by C ₁ -C ₄ alkyl 3, 5 or 6-membered, exactly one nitrogen atom and optionally containing an oxygen atom, saturated or aromatic ring, which is linked via the nitrogen atom.

2. Pyrazolylpyrazole according to claim 1, wherein
R ¹ C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₈ cycloalkyl-C ₁ - C ₄ alkyl, these four radicals optionally being substituted by one or several, identical or different halogen atoms are substituted;
R ² C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, these six radicals optionally being substituted by one or more identical or different halogen atoms, or
R ¹ and R ² form with the carbon atom carrying them a 5- to 7-membered saturated ring which is optionally substituted by one or two identical or different radicals from the group halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ - Alkoxy is substituted;
R ^{3 is} hydrogen, halogen, cyano, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the two latter radicals optionally being substituted by one or more identical or different halogen atoms;
R ^{4 is} hydrogen, nitro, cyano, C (X) YR ⁷ , C (X) NR ⁸ R ⁹ , C (X) R ⁷ , SO ₂ R ⁷ , SO ₂ OR ⁷ or SO ₂ NR ⁸ R ⁹ ;
R ⁵ and R ^{6 are} each independently of one another hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ - C ₆ alkoxy or C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, the three latter radicals optionally are substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group together with the carbon atom carrying them form a 3- to 6-membered saturated ring, which may be replaced by up to four identical or different radicals from the group halogen, hydroxy, C ₁ - C ₄ alkyl and C ₁ -C ₄ alkoxy is substituted, or
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups together with the carbon atoms carrying them form a 3- to 6-membered saturated ring which may be substituted by up to four identical or different radicals from the group halogen, Amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, hydroxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond;
R ^{7 is} hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the four latter radicals being optionally by one or more, identical or different Residues from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, cyano or halogen are substituted, and the carbon chain of these four residues mentioned being optionally substituted by one or more, identical or different heteroatoms from the group consisting of oxygen and sulfur is interrupted;
R ⁸ , R ⁹ each independently of one another are hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the four last-mentioned radicals optionally being substituted by a or more, identical or different radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl or halogen are substituted, and the carbon chain of these four radicals optionally being substituted by one or more, identical or different heteroatoms from the Group oxygen and sulfur is interrupted, or
R ⁸ and R ⁹ together with the nitrogen atom carrying them form a 3-, 5- or 6-membered saturated, partially saturated or fully unsaturated ring, optionally substituted by up to four methyl groups, in which case one carbon atom is optionally replaced by an oxygen atom;
Q optionally by one or more, identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) ) -amino, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ - alkylthio, C ₁ -C ₆ - alkylsulphinyl, C ₁ -C ₆ -alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ - alkyl) aminosulfonyl, wherein the twelve last-mentioned radicals optionally substituted by one or several, identical or different halogen atoms are substituted, substituted heterocyclyl which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur, and
X and Y each independently represent oxygen or sulfur. 3. Pyrazolylpyrazole according to claim 1 or 2, wherein
R ^{1 is} C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl or C ₃ -C ₆ cycloalkyl, these three radicals optionally being substituted by up to five identical or different halogen atoms;
R ² C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ - C ₄ -alkylsulfonyl, these five radicals optionally being replaced by bis are substituted to five identical or different halogen atoms, or
R ¹ and R ² form with the carbon atom carrying them a 5- or 6-membered saturated ring which is optionally substituted by one or two identical or different radicals from the group halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ - Alkoxy is substituted;
R ^{3 is} halogen, cyano or C ₁ -C ₄ alkyl, the latter radical optionally being substituted by up to five identical or different halogen atoms;
R ⁴ nitro, cyano, C (X) YR ⁷ , C (X) NR ⁸ R ⁹ , SO ₂ R ⁷ , SO ₂ NR ⁸ R ⁹ or C (X) R ⁷ ;
R ⁵ and R ⁶ are each independently hydrogen, halogen, hydroxy, C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ -alkoxy-C ₁ -C ₂ alkyl, where the last three Residues are optionally substituted by one or more, identical or different halogen atoms, or
R ⁵ and R ⁶ each form a (CR ⁵ R ⁶ ) group, together with the carbon atom carrying them, form a 3-, 5 or 6-membered saturated ring which is optionally substituted by up to four identical or different radicals from the group halogen, C ₁ -C ₂ alkyl and C ₁ -C ₂ alkoxy is substituted, or
two R ^{5 of} two directly adjacent or not directly adjacent (CR ⁵ R ⁶ ) groups form, together with the carbon atoms carrying them, a 3, 5 or 6-membered saturated ring which, if appropriate, consists of up to four identical or different radicals from the Halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy group is substituted, or
two R ^{5 of} two directly adjacent (CR ⁵ R ⁶ ) groups together form a bond, or
two R ⁵ and two R ⁶ each of two directly adjacent (CR ⁵ R ⁶ ) groups together each form a bond;
R ^{7 is} hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -alkynyl, the three latter radicals optionally being substituted by up to four identical or different radicals from the group C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkoxycarbonyl, cyano or halogen are substituted, and wherein the carbon chain of these four radicals mentioned is optionally interrupted by a heteroatom from the group consisting of oxygen and sulfur;
R ⁸ , R ⁹ each independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -alkynyl, the four last-mentioned radicals optionally being replaced by bis are substituted to four identical or different radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl or halogen, and the carbon chain of these four radicals mentioned being optionally substituted by one or two identical or different heteroatoms from the group oxygen and sulfur is interrupted, or
R ⁸ and R ⁹ together with the nitrogen atom carrying them form a 3-, 5- or 6-membered saturated, partially saturated or completely unsaturated ring, optionally substituted by up to two methyl groups, in which case one carbon atom is optionally replaced by an oxygen atom;
Q optionally by up to three identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) -amino, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio , C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, aminosulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di- (C ₁ -C ₆ alkyl) - aminosulfonyl, wherein the twelve last-mentioned radicals are optionally substituted by up to three identical or different halogen atoms are substituted, substituted heterocyclyl, which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur;
X oxygen or sulfur, and
Y oxygen
mean. 4. Pyrazolylpyrazole according to any one of claims 1 to 3, wherein
R ¹ C ₁ -C ₄ alkyl;
R ^{2 is} C ₁ -C ₃ alkyl, C ₁ -C ₃ alkylthio, C ₁ -C ₃ alkylsulfinyl, C ₁ -C ₃ alkylsulfonyl or C ₁ -C ₃ alkoxy, these radicals optionally being substituted by up to five identical or different halogen atoms from the group fluorine and chlorine are substituted, or
R ¹ and R ² together form a - (CH ₂ ) ₃ - or - (CH ₂ ) ₄ group,
R ³ bromine or chlorine;
R ⁴ nitro, cyano or CSNH ₂ ;
R ⁵ and R ⁶ each independently of one another are hydrogen, fluorine, bromine, chlorine, hydroxy, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, the three latter radicals optionally being substituted by up to five identical or different halogen atoms;
Q optionally by up to three identical or different radicals from the group amino, hydroxy, halogen, nitro, cyano, oxo, thioxo, carboxy, formyl, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) -amino, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio , C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - alkylsulfonyl, aminosulfonyl, C ₁ -C ₄ alkylaminosulfonyl, di- (C ₁ -C ₄ alkyl) - aminosulfonyl, wherein the twelve last-mentioned radicals are optionally substituted by up to three identical or different halogen atoms are substituted, substituted heterocyclyl which contains up to 10 ring atoms, of which up to five independently of one another come from the group nitrogen, oxygen and sulfur,
mean. 5. A process for the preparation of heterocyclyl- and heterocyclylalkyl-substituted pyrazolylpyrazoles of the general formula (I) according to one of claims 1 to 4,
characterized in that

• a) in the case of n = 0 or 1
  a compound of the formula (II),
  with a compound of the general formula (III),
  QH (III)
  is reacted in the presence of a base and optionally a catalyst; b) in the case of n = 0
  a compound of the general formula (IV),
  with a compound of the general formula (V),
  is implemented;
• c) in the case of n = 2
  a compound of the general formula (VI),
  with a compound of the general formula (VII),
  is reacted in the presence of a base;
• d) in the case of n = 3
  a compound of the formula (VIII) reductively into a compound of the formula (IX), this by halogen exchange in a compound of the formula (X) and finally by base-catalyzed reaction with a heterocyclic compound of the formula (III) in a compound of the formula (XI ) is transferred.
  

6. Herbicidal agents, characterized by a content of at least one Compound of general formula (I) according to one of claims 1 to 4. 7. Herbicidal compositions according to claim 5 in a mixture with formulation auxiliaries. 8. Process for combating undesirable plants, thereby characterized in that an effective amount of at least one compound of general formula (I) according to any one of claims 1 to 4 or a herbicidal Means according to claim 5 or 6 on the plants or on the location of the undesirable Plant growth applied. 9. Use of compounds of general formula (I) according to one of the Claims 1 to 4 or of herbicidal compositions according to claim 5 or 6 for Control unwanted plants. 10. Use according to claim 8, characterized in that the Compounds of general formula (I) for controlling unwanted plants can be used in crops of crops. 11. Use according to claim 9, characterized in that the Crops are transgenic crops.