BR112013023587B1 - N-(1,2,5-OXADIAZOLE-3-YL)-, N-(TETRAZOLE-5-YL)- AND N-(TRIAZOLE-5-YL)BICYCLOARYL CARBOXAMIDES AND THEIR USE AS HERBICIDES - Google Patents

Abstract

CARBOXAMIDES OF N-(1,2,5-OXADIAZOLE-3-YL), N-(TETRAZOLE-5-YL) AND N-(TRIAZOLE-5-YL)BICYCLOARYL AND THEIR USE AS HERBICIDES. The present invention relates to N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloaryl carboxamide of the formula general (I) (I), which are described as herbicides. In this formula (I), R3, R4 and R5 are, in each case, radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a heterocycle. X and Y are, in each case, oxygen and sulfur.

Description

DESCRIPTION

[001] The invention relates to the technical area of herbicides, especially herbicides for the selective control of harmful weeds and grasses in useful plant crops.

[002] From documents WO2003/010143 and WO2003/010153 certain N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides and their pharmacological action are known. Under CAS No. 639048-78-5 the compound N-(1-propyltetrazol-5-yl)-2,5-dichlorobenzamide is known. No herbicidal action of these compounds is described in these documents. From European patent applications No. 0912169.0 and No. 10174893.7, which have older priority dates but not yet published as of the priority date of the present application, N-(1,2,5-oxadiazol-3-yl )-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and their use as herbicides.

[003] It has now been discovered that N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl) and N-(triazol-5-yl)bicycloaryl carboxamides are particularly well suitable as herbicides.

[004] An object of the present invention is, therefore, N-(1,2,5-oxadiazol-3-yl), N-(tetrazol-5-yl) or N-(triazol-5-yl)bicycloaryl carboxamides of formula (I) or salts thereof in which Q is a radical Q1, Q2or Q3,

[005] R1 is (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, ( C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C2-C6)-alkenyl , (C1-C6)-alkoxy-(C2-C6)-alkynyl, CH2R6, heteroaryl, heterocyclyl or phenyl, with the last three radicals being replaced, in each case, by radicals u from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl, (C1-C6 )-alkylsulfonyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl;

[006] R2 is hydrogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy , (C2-C6)-alkenyl, (C2-C6)-alkenyloxy, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-alkynyloxy, halo-(C2-C6) -alkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl , or heteroaryl, heterocyclyl or phenyl, in each case substituted by radicals or from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;

[007] R3 and R4 are, in each case, independently of each other, hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2 -C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C7)-cycloalkyl, (C3-C7)-halocycloalkyl, (C1-C6)-alkoxy, (C1 -C6)-haloalkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylathio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6 )- haloalkylsulfonyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro or cyano;

[008] R5 is hydrogen or fluorine;

[009] R6 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C3- C6)-cycloalkyl, or heteroaryl, heterocyclyl or phenyl, in each case substituted by radicals u of the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;

[0010] R7 and R8 are, in each case, independently of each other, hydrogen, (Ci-C6)-alkyl, halo-(Ci-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2 -C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C7)-cycloalkyl, halo-(C3-C7)-cycloalkyl, -OR9, S(O)mR9 , (C1-C6)-alkylthio, halo-(C1-C6)-alkylanium, (C1-C6)-alkylsulfinyl, halo-(C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, halo-(C1- C6)-alkylsulfonyl, (C1-C6)-alkoxy-(C1-C4)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, with the last three radicals being replaced, in each case, by radicals u from the group consisting of halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkylthio, (C1-C6 )-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl, or

[0011] R7 and R8, together with the carbon atom to which they are bonded, form the unit of-X1-(CH2)r-X2-, -(CH2)s-X3-, -(CH2)t-X3 -CH2-, - (CH2)v-X3-CH2CH2- or -(CH2)w-, in which each of the groups (CH2) is replaced by radicals m from the group consisting of halogen, methyl and (C1-C3) -alkoxy, or

[0012] R7 and R8, together with the carbon atom to which they are attached, form the unit of -O-N((Ci-C3)-alkyl)-CHR10-CH2- or -O- N=CR10-CH2-, in which each of the groups (CH2) is replaced by m radicals from the group consisting of halogen and methyl;

[0013] R9 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl , halo-(C2-C6)-alkynyl, (C3-C7)-cycloalkyl, (C3-C7)-halocycloalkyl, (C3-C7)-cycloalkyl-(C1-C3)-alkyl, halo-(C3-C7) -cycloalkyl-(C1-C3)-alkyl, heteroaryl, heterocyclyl or phenyl, with the last three radicals being replaced, in each case, by radicals from the group consisting of halogen, nitro, cyano, (C1-C6) -alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkylathio, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6) -alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl;

[0014] R10 is hydrogen, (C1-C3)-alkyl, or phenyl substituted by radicals or from the group consisting of (C1-C3)-alkyl, halogen, cyano and nitro;

[0015] R11 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, formyl, (C2-C6)-alkylcarbonyl, (C2-C6)-alkoxycarbonyl or ( C1-C2)-alkylsulfonyl;

[0016] X and Y are, in each case, independently of each other, O, S, SO, SO2, C=O, C=S, NR10, CR7R8, C=NOR10 or C=NN(R11)2;

[0017] X1 and X2 are, in each case, independently of each other, O, S or N((C1-C3)-alkyl); X3 is O or S; m is 0, 1 or 2; n is 1, 2 or 3; r is 2, 3 or 4; s is 2, 3, 4 or 5; t is 1, 2, 3 or 4; u is 0, 1, 2 or 3; v is 2 or 3; w is 2, 3, 4, 5 or 6.

[0018] In formula (I) and in all subsequent formulas, alkyl radicals with more than two carbon atoms can be linear or branched. Alkyl radicals mean, for example, methyl, ethyl, n- or isopropyl, n-, iso-, tert- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

[0019] Heterocyclyl is a cyclic radical, saturated, semi-saturated or completely unsaturated, which contains 3 to 6 ring atoms, of which 1 to 4 are from the oxygen, nitrogen and sulfur groups, and which can be additionally fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

[0020] Heteroaryl is a cyclic, aromatic radical, which contains 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur and which can additionally be a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl , 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1 ,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1 ,2,3,4-tetrazolyl, 1H-1,2,3,4- tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

[0021] When a group is polysubstituted by radicals, then it must be understood that this group is replaced by one or more radicals equal to or different from the aforementioned radicals.

[0022] The compounds of general formula (I), depending on the type and bonding of the substituents, may appear as stereoisomers. If, for example, several asymmetric carbon atoms are present, then enantiomers and diastereomers can occur. Stereoisomers also occur, when n represents 1 (sulfoxides). Stereoisomers can be obtained from mixtures formed in production, according to usual separation methods, by chromatographic separation processes. Stereoisomers can also be produced selectively through the use of stereoselective reactions, using basic materials and/or optically active adjuvants. The invention also relates to all stereoisomers and mixtures thereof, which are comprised by the general formula (I), but are not specifically defined.

[0023] Compounds of general formula (I) are preferred, in which

[0024] R1 is (C1-C3)-alkyl, (C3-C5)-cycloalkyl, halo-(C1-C3)-alkyl or (C1-C3)-alkoxy-(C1-C3)-alkyl;

[0025] R2 is hydrogen, (Ci-C3)-alkyl, (C3-C5)-cycloalkyl, halo-(Ci-C3)-alkyl, (Ci-C3)-alkoxy, halo-(Ci-C3)-alkoxy , cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, methoxycarbonyl, ethoxycarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or methoxymethyl;

[0026] R3 and R4, are, in each case, independent of each other, hydrogen, (Ci-C3)-alkyl, halo-(Ci-C3)-alkyl, (C3-C5)-cycloalkyl, (Ci-C3 )-alkoxy, (C1-C3)-haloalkoxy, (C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy-(C1-C4)- alkyl, halogen, nitro or cyano;

[0027] R5 is hydrogen;

[0028] R7 and R8 are, in each case, independent of each other, hydrogen, (Ci-C3)-alkyl, halo-(Ci-C3)-alkyl, (C3-C5)-cycloalkyl, -OR9, - S(O)mR9, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, with the last three radicals being replaced by radicals u from the group consisting of halogen, nitro, cyano, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C3 -C5)-cycloalkyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkoxy, halo-(C1-C3)-alkoxy and (C1 -C3)-alkoxy-(C1- C3)-alkyl, or

[0029] R7 and R8, together with the carbon atom to which they are bonded, form the unit -X1-(CH2)r-X2-, -(CH2)s-X3-, -(CH2)t-X3- CH2-, - (CH2)v-X3-CH2CH2- or -(CH2)w-, in which each of the groups (CH2) is replaced by radicals m from the group consisting of halogen, methyl and (C1-C3)- alkoxy, or

[0030] R7 and R8, together with the carbon atom to which they are linked, form the unit -O-N((Ci-C3)-alkyl)-CHR10-CH2- or -O- N=CR10-CH2-, in which each of the groups (CH2) is replaced by m radicals from the group consisting of halogen and methyl;

[0031] R9 is hydrogen, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C2-C3)-alkenyl, (C2-C4)-alkynyl, (C3-C5)-cycloalkyl, ( C3-C5)- cycloalkyl-(C1-C3)-alkyl, heteroaryl, heterocyclyl or phenyl, with the last three radicals being replaced, in each case, by radicals from the group consisting of halogen, nitro, cyano, (C1 -C3)-alkyl, halo-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1 -C3)-alkoxy, halo-(C1-C3)-alkoxy and (C1-C3)-alkoxy-(C1-C3)-alkyl;

[0032] R10 is hydrogen or (C1-C3)-alkyl;

[0033] X and Y are, in each case, independent of each other, O, SO2, C=O, C=S, CR7R8, C=NOR10;

[0034] X1 and X2 are, in each case, independent of each other, O, S, N(CH3); X3 is O or S; m is 0, 1 or 2; n is 1 or 2; r is 2 or 3; s is 2, 3 or 4; t is 1, 2 or 3; u is 0, 1 or 2; v is 2 or 3; w is 2, 3, 4 or 5.

[0035] In all formulas cited below, substituents and symbols, when not otherwise defined, have the same meaning as described under formula (I).

[0036] Compounds according to the invention, in which Q is Q1 or Q2, can be prepared, for example, by the method shown in scheme 1, by base-catalyzed reaction of a bicyclic benzoyl chloride (II) with a 5- amino-1H-1,2,4-triazole or 5-amino-1H-tetrazole (III): Scheme 1

[0037] In the same B represents CH or N. The bicyclic benzoyl chlorides of formula (II) or the benzoic acids that serve as their base are, in principle, known and can be prepared, for example, according to the methods described in WO 96/25413, WO 97/09324, WO 97/30993, WO 97/08164, WO 98/49159, WO 98/35954, WO 98/12192, WO 0014087 and EP 0636622.

[0038] Compounds according to the invention, in which Q is Q1 or Q2, can also be prepared, for example, by the method shown in scheme 2, by reacting a benzoic acid of formula (IV) with a 5-amino -1H-1,2,4-triazole or 5-amino-1H-tetrazole (III): Scheme 2 Caption: activation

[0039] For activation, it is possible to use dehydrating reagents, which are typically used for amidation reactions, for example, 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-carbonyl trioxide 2,4,6-tripropyl-1,3,5,2,4,6-trioxatrifosphinan (T3P) etc.

[0040] Compounds according to the invention, in which Q is Q1 or Q2, can also be prepared, for example, by the method shown in scheme 3, by reaction of an N-(1H-1,2,4-triazole- 5-yl)benzamide, N-(1H-tetrazol-5-yl)benzamide, N-(1H-1,2,4-triazol-5-yl)nicotinamide or N-(1H-tetrazol-5-yl)nicotinamide :

[0041] For this reaction mentioned in Scheme 3, alkylating agents, such as, for example, halogens, alkyl sulfonates or dialkyl sulfates, can be used in the presence of a base. It may be convenient to change reaction steps in their sequence. Thus, benzoic acids, which contain a sulfoxide, cannot simply be converted to their acid chlorides. In this case, the option is offered to first prepare the amide to the thioether stage and then oxidize the thioether to the sulfoxide.

[0042] The 5-amino-1H-tetrazoles of formula (III) can be obtained commercially or prepared analogously to known methods in the literature. For example, substituted 5-aminotetrazoles can be prepared from aminotetrazole according to the method described in Journal of the American Chemical Society (1954), 76, 923-924:

[0043] In the above reaction, X is a leaving group, such as iodine. 5- Substituted aminotriazoles can also be synthesized, for example, as described in the Journal of the American Chemical Society (1954) 76, 88-89:

[0044] The 5-amino-1H-triazoles of formula (III) can be obtained commercially or prepared analogously to known methods in the literature. For example, substituted 5-aminotriazoles can be prepared from aminotetrazole according to the method described in Zeitschrift für Chemie (1990), 30(12), 436 - 437:

[0045] Substituted 5-Aminotriazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97(2), 396-404:

[0046] Substituted 5-Aminotriazoles can also be synthesized, for example, as described in Angewandte Chemie (1963), 75, 918:

[0047] Compounds according to the invention, in which Q represents Q3, can be prepared, for example, by the method shown in Scheme 4, by base-catalyzed reaction of a bicyclic benzoyl chloride (II) with a 4- amino-1,2,5-oxadiazole (VI): Scheme 4

[0048] Compounds according to the invention can also be prepared by the method described in Scheme 5, reacting a bicyclic benzoic acid of formula (IV) with a 4-amino-1,2,5-oxadiazole (VI): Scheme 5

[0049] For activation, it is possible to use dehydrating reagents, which are typically used for amidation reactions, for example, 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl- 1,3,5,2,4,6-trioxatrifosphinan 2,4,6-trioxide (T3P) etc.

[0050] The 4-amino-1,2,5-oxadiazoles of formula (VI) are commercially available or can be prepared analogously to known methods in the literature. For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared from β-keto esters by the method described in Russian Chemical Bulletin, Int. Ed., vol. 54, 4, pp. 10321037 (2005):

[0051] 3-Aryl-4-amino-1,2,5-oxadiazoles can be synthesized, for example, as described in Russian Chemical Bulletin, 54(4), 1057-1059, (2005) or Indian Journal of Chemistry , Section B: Organic Chemistry Including Medicinal Chemistry, 26B(7), 690-2, (1987):

[0052] 3-Amino-4-halo-1,2,5-oxadiazoles can be prepared, for example, by a Sandmeyer reaction commercially available 3,4-diamino-1,2,5-oxadiazole by the method described in Hetero - atom Chemistry 15(3), 199-207 (2004):

[0053] Nucleophilic R2 radicals can be introduced into 3-amino-1,2,5-oxadiazoles by replacing the leaving group L, as described in Journal of Chemical Research, Synopses, (6), 190, 1985 or in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614, 2004:

[0054] Collections of compounds of formula (I) and/or salts thereof, which can be synthesized according to the reactions mentioned above, can also be prepared in parallel, and this can occur manually, partially automatically or completely automatic. In this case, it is possible, for example, to automate the execution of the reaction, the finishing or purification of products or intermediate stages. In total, this means a procedure, as described by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Günter Jung), Wiley, 1999, on pages 1 to 34.

[0055] For parallel execution of the reaction and finishing, it is possible to use various commercially obtainable instruments, for example, Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MultiPROBE Automated Workstations from PerkinElmer, Waltam, Massachusetts 02451, USA. For parallel purification of compounds of formula (I) and salts thereof or of intermediates, which occur in the course of preparation, available apparatus include chromatography apparatus, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504 , USA.

[0056] The described devices lead to a modular procedure, in which the work steps are automated, but manual operations need to be carried out between the work steps. This can be avoided by using partially or fully integrated automation systems, in which the respective automation modules are serviced by robots. These automation systems can be purchased from Caliper, Hopkinton, MA 01748, USA.

[0057] The execution of individual or multiple synthesis steps can be supported by the use of polymer-aided impurity-scavenging reagents/resins. The technical literature describes several experimental protocols, for example, ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0058] In addition to the methods described here, compounds of general formula (I) and salts thereof can be prepared completely or partially by solid phase-assisted methods. For this purpose, individual intermediates or all intermediates in the synthesis or in a synthesis adapted for the corresponding procedure are linked to a synthesis resin. Solid phase-assisted synthesis methods are sufficiently described in the technical literature, e.g., Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Günter Jung), Wiley, 1999. The use of solid phase-assisted synthesis methods allows several protocols known from the literature and they can again be executed manually or automatically. Reactions can be carried out, for example, using IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

[0059] In both solid and liquid phases, the execution of individual or multiple synthesis steps can be assisted by the use of microwave technology. A series of experimental protocols are described in the technical literature, for example, in Microwaves in Organic and Medicinal Chemistry (editor C.O. Kappe and a. Stadler), Wiley, 2005.

[0060] Preparation according to the processes described here provides compounds of formula (I) and salts thereof in the form of collections of substances, which are called libraries. Also an object of the present invention are libraries, which contain at least two compounds of formula (I) and salts thereof.

[0061] The compounds of formula (I) (and/or salts thereof), hereinafter referred to collectively as "compounds according to the invention", exhibit excellent herbicidal efficiency against a broad spectrum of annual mono- and dicotyledonous plants economically important. Even difficult-to-control perennial noxious plants that sprout from rhizomes, root stumps or other permanent organs are well covered by the active substances.

[0062] Therefore, an object of the present invention is also a process for controlling undesirable plants or for regulating plant growth, preferably in plant cultures, in which one or more compound(s) are applied in accordance with the invention on plants (e.g. harmful plants such as mono- or dicotyledonous weeds or undesirable crop plants), on seed material (e.g. grains, seeds or vegetative multiplication organs such as tubers or parts of buds with bubbles, or the area on which the plants grow (cultivation area). In this case, the compounds according to the invention can be applied, for example, in the pre-sowing process (optionally also by incorporation into the soil). ), pre-emergence or post-emergence. In detail, some representatives of the mono- and dicotyledonous weed flora are mentioned, which can be controlled by the compounds according to the invention, without the citation having to give any limitation to certain species.

[0063] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fim - bristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0064] Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex , Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lami- um, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, My- osotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus , Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0065] When the compounds according to the invention are applied to the soil surface, before germination, then the emergence of weed seedlings is totally prevented or the weeds grow to the germination leaf stage, but then stop their growth. growth and finally die completely after three to four weeks.

[0066] When applying active substances to green plant parts in the post-emergence process, after treatment, growth stops and the harmful plants remain in the existing growth stage until the moment of application or die completely, after a certain period of time, so that, in this way, competition from weeds, harmful to crop plants, is eliminated early and lastingly.

[0067] Although the compounds according to the invention exhibit excellent herbicidal activity in relation to mono- and dicotyledonous weeds, cultural plants of economically important crops, for example, dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita , Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, particularly Zea and Triticum, are damaged only to a small extent or even not damaged at all, depending on the structure of the respective compound according to the invention and the amount of application thereof. For these reasons, the present compounds are very well suited for the selective control of undesirable plant growth in crops of agriculturally useful plants or ornamental plants.

[0068] Furthermore, the compounds according to the invention (depending on their respective structure or the amount of application distributed) exhibit excellent growth-regulating properties in crop plants. They intervene in a regulatory way in the plant's endogenous metabolism and, therefore, can be used to selectively influence plant ingredients and to facilitate harvesting, such as, for example, promoting dissection and growth inhibition. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without, in this case, killing the plants. An inhibition of vegetative growth plays an important role in many mono- and dicotyledonous crops, which, for example, can reduce or completely prevent the need for storage in warehouses.

[0069] Due to their herbicidal and plant growth regulatory properties, the active substances can also be used to control harmful plants in genetically modified or conventional mutagenesis modified plant crops. Transgenic plants are distinguished by particularly advantageous properties, for example, resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or plant disease-causing agents, such as certain insects or microorganisms, such as fungi , bacteria or viruses. Other special properties refer, for example, to the harvested material, with regard to quantity, quality, storage capacity, composition and special ingredients. Thus, transgenic plants with higher starch content or modified starch quality or those with another fatty acid composition of the crop material are known.

[0070] The application of the compounds according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice and corn is preferred. or crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable species. Vegetables. Preferably, the compounds according to the invention can be used as herbicides on useful crop plants, which are resistant or have been rendered resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0071] Conventional means for the production of new plants, which in comparison with previously existing plants present modified properties, consist, for example, of classical cultivation processes and the generation of mutants. Alternatively, new plants with modified properties can be generated with the help of recombinant technology processes (see, for example, EP 0221044, EP 0131624). For example, in several cases the following have been described: - modifications of recombinant technology of crop plants, for the purpose of modifying starch synthesized in plants (e.g. WO 92/011376, WO 92/014827, WO 91/019806), - plants of transgenic crops, which are resistant against certain herbicides of the glufosinate type (comp., for example, EP-A-0242236, EP-A-0242246) or of the glyphosate type (WO 92/000377) or of the sulfonylurea type (EP-A -0257993, US 5,013,659), - transgenic crop plants, e.g. cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant against certain pests (EP-A-0142924, EP- A-0193259) - transgenic crop plants, with modified fatty acid composition (WO 91/013972), - genetically modified crop plants, with new ingredients or secondary substances, for example new phytoalexins, which produce a higher resistance to diseases (EPA 0309862, EPA0464461), - genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398), - transgenic crop plants, which produce pharmaceutically and diagnostically important proteins ("molecular pharming" ) - transgenic crop plants, which are distinguished by higher yields or better quality - transgenic crop plants which are distinguished by a combination, for example, of the properties mentioned above ("gene stacking");

[0072] Numerous molecular biology techniques, by means of which new transgenic plants with modified properties can be generated, are in principle known: see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0073] For these recombinant manipulations, nucleic acid molecules, which allow mutagenesis or a sequence change by recombination of DNA sequences, can be introduced into plasmids. For example, base substitutions can be made, partial sequences can be removed, or natural or synthetic sequences can be added with the help of standard methods. To join DNA fragments to each other, it is possible to add adapters or linkers to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone", VCH Weinheim 2nd ed., 1996.

[0074] For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one antisense RNA, one sense RNA, to obtain a cosuppression effect, or the expression of at least a correspondingly constructed ribozyme, which specifically dissociates transcripts from the gene product cited above. For this purpose, it is possible to use DNA molecules, which encompass the entire coding sequence and a gene product, including any flanking sequences that may be present, and also DNA molecules, which only encompass parts of the coding sequence, being that these parts must be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences, which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

[0075] When expressing nucleic acid molecules in plants, the synthesized protein can be located in any desired compartment of the plant cell. But, to obtain localization in a specific compartment, it is possible, for example, to link the coding region with DNA sequences, which guarantee localization in a specific compartment. Such sequences are known to the skilled artisan (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846- 850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in the organelles of plant cells.

[0076] Transgenic plant cells can be regenerated into whole plants according to known techniques. In the case of transgenic plants, they can, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.

[0077] Thus, transgenic plants are obtainable, which present properties modified by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0078] Preferably, the compounds (I) according to the invention can be used in transgenic crops, which are resistant to growth regulators, such as, for example, dicamba, or against herbicides, which inhibit essential plant enzymes, for example, acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydrophenylpyruvate dioxygenases (HPPD), or which are resistant against herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl isoxazoles and analogous active substances.

[0079] When applying the active substances according to the invention to transgenic crops, in addition to the effects to be observed in other crops, effects frequently occur in relation to harmful plants, which are specific to the application in the respective transgenic crop, e.g. a modified or specially expanded weed spectrum that can be controlled, modified application quantities that can be used for application, preferably good combining ability with the herbicides to which the transgenic crop is resistant, as well as an influence on the growth and yield of transgenic crop plants.

[0080] For this reason, it is also an object of the invention to use the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0081] The compounds according to the invention can be applied in the form of spray powders, emulsifiable concentrates, sprayable solutions, dusting agents or granulates in the usual preparations.

[0082] The compounds according to the invention can be formulated in different ways, depending on which biological and/or chemical-physical parameters have been specified. Formulation possibilities are of interest, for example: spray powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions and water in oil, sprayable solutions, suspension concentrates (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting agents (DP), disinfectants, granules for spray application and in soil, granules (GR) in the form of microgranules, spray, coating and adsorption granules, water dispersible granules (WG), water soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are in principle known and are described, for example, in: Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

[0083] The necessary formulation adjuvants, such as inert materials, surfactants, solvents and other additives are also known and are 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. Pub. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflachenaktive Ãthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

[0084] Based on these formulations, combinations can also be prepared with other pesticide-acting substances, such as, for example, insecticides, acaricides, herbicides, fungicides, as well as with surfactants, fertilizers and/or growth regulators, for example , in the form of a finished formulation or as a tank mix. Suitable antidotes are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadiphene-ethyl, cloquintocet-mexyl and dichlormid.

[0085] Spray powders are prepared, which can be uniformly dispersed in water, which in addition to the active substance, contain, in addition to a diluent or inert substance, surfactants of an ionic and/or non-ionic nature (cross-linkers, dispersing agents) , for example, polyoxethylated alkylphenols, polyoxethylated fatty alcohols, polyoxetylated fatty amines, fatty acid polyglycol ether sulfate, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalin -sodium sulfonate or also sodium oleoylmethyltaurate. For the production of spray powders, the herbicidal active substances are finely ground, for example, in usual apparatus, such as pestle mills, blow mills and air jet mills, and simultaneously or subsequently mixed with the formulation adjuvants.

[0086] Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example, butanol, cyclohexanone, dimethylformamide, xylene or higher boiling aromates or hydrocarbons or a mixture of organic solvents, under the addition of one or more surfactants of ionic and/or non-ionic nature (emulsifiers). As emulsifiers can be used, for example, calcium salts of alkylarylsulfonate, such as Cadodecylbenzenesulfonate or non-ionic emulsifiers, such as fatty acid polyglycholester, alkylaryl polyglycolether, fatty alcohol polyglycolether, propylene oxide-oxide condensation products of ethylene, alkylpolyether, sorbitan ester, such as, for example, sorbitan fatty acid ester or polyoxyethylene sorbitan ester, such as, for example, polyoxyethylene sorbitan fatty acid ester.

[0087] Dusting agents are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0088] Suspension concentrates can be water or oil based. They can be prepared, for example, by wet grinding using commercially available pearl mills and, optionally, adding surfactants, such as those already listed above, for example, in other types of formulation.

[0089] Emulsions, for example, oil-in-water (EW) emulsions, can be produced, for example, by means of agitators, colloidal mills and/or static mixers, under the use of aqueous organic solvents and, optionally, surfactants, such as already listed above in other types of formulation.

[0090] Granules can be produced by spraying the active substance on inert granulated material, suitable for adsorption, or by applying active substance concentrates using adhesive agents, for example, polyvinyl alcohol, polyacrylate sodium or also mineral oils, on the surface of support materials such as sand, kaolinite or inert granular material. Also suitable active substances can be granulated in the usual way for production and fertilizer granules - optionally, in mixture with fertilizers.

[0091] Water-dispersible granules are generally produced according to the usual processes, such as spray drying, turbulent layer granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0092] For production of dish, fluid layer, extruder and spray granules, see, for example, processes in "SprayDrying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

[0093] For other details regarding the formulation of pesticide compositions, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, page 81-96 and J.D. Freyer , S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0094] Agrochemical preparations generally contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of compounds according to the invention. In spray powders, the active substance concentration makes up, for example, approximately 10 to 90% by weight, the remainder, up to 100% by weight, consists of usual formulation components. In emulsifiable concentrates, the concentration of active substance can be approximately 1 to 90, preferably 5 to 80% by weight. Formulations in powder form contain 1 to 30% by weight of active substance, preferably most often 5 to 20% by weight of active substance, spray solutions contain approximately 0.05 to 80, preferably 2 to 50% by weight of active substance. In water-dispersible granulates, the active substance content depends, in part, on whether the active compound is present in liquid or solid form, and which granulation adjuvants, fillers, etc. are used. they're used. In water-dispersible granules, the active substance content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0095] In addition, the aforementioned active substance formulations optionally contain adhesives, crosslinkers, dispersing agents, emulsifiers, penetrating agents, preservatives, protection against frost and solvents, fillers, support materials and dyes, defoamers, inhibitors of evaporation, in each case usual, and agents that influence the pH value and viscosity.

[0096] Based on these formulations, combinations can also be produced with other substances with pesticidal action, such as, for example, insecticides, acaricides, herbicides, fungicides, as well as with surfactants, fertilizers and/or growth regulators, for example, in the form of a finished formulation or as a tank mix.

[0097] As combination components for the compounds according to the invention in mixture formulations or in tank mixing, for example, known active substances can be used, which are based on an inhibition of, for example, acetic synthase. tolactate, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimat-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytofinal saturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example , in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and literature cited there. As known herbicides or plant growth regulators, which can be combined with the compounds of the invention, there can be mentioned, for example, the following active substances (the compounds are designated or with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name or code number) and always include all forms of application, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. In this case, one and, in part, also several forms of application are mentioned: acetochlor, acibenozolar, acibenozolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alidochlor, alloxydime, alloxidime-sodium, ametrine, amicarbazone, amidochlor, amidosulfurone, aminocyclopyrachlor, aminopyralid, amitrol, ammonium sulfamate, ancymidol, anilophos, assulamon, atrazine, azafenidine, azimsulfuron, aziprothrine, beflubutamide, benazoline, ethyl benazoline, benocarbazone, benofluralin, benofuresate, bensulide, bensulfurone, bensulfurone-methyl, bentazone, benzofendizone, benzobicyclone, benzofenap, benzofluor, benzoilprop, biciclopyrone, bifenox, bilanafos, bilana- phos-sodium, bispiribac, bisspiribac-sodium, bromacil, bromobutide, bromophenoxime, bromoxynil, bromurone, buminaphos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydime, butylate, cafenstrol, carbetamide, carfenotrazone, carfenotrazone-ethyl, chlorethoxyphene, chlorambene, clorazifop, chloroazifop-butyl, chlorobromurone, chlorobufamo, chlorofenac, chlorophenoac- sodium, chlorophenprop, chloroflurenol, chloroflurenol-methyl, chloroidazone, chloroimurone, chloroimuron-ethyl, chloromequat chloride, chloronitrofen, chlorophthalim, chlorothal-dimethyl, chlorotolurone, chlorosulfuron, cynidone, cynidone-ethyl, cinmethylline, cinosulfuron, clethodime, clodinafop, clodinafop- propargyl, clofenoketo, clomazone, clomeprop, cloprop, clopyralid, cloransulamus, cloransulamo-methyl, cumilurone, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamurone, cycloxidime, cyclurone, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, ciprazole, 2,4-D, 2,4-DB, daimuron/dimrone, dalapon, daminozide, dazomet, n-decanol, desmedifamus, desmethrin, detosyl pyrazolate (DTP), dialate, dicamba, diclobenyl, dichloroprop, dichloroprop- P, diclofop, diclofop-methyl, diclofop-P- methyl, diclosulam, diethyl, diethyl-ethyl, difenoxuron, difenozoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefurone, dikegulac-sodium, dimefurone, dimepiperate, dimethachlor, dimetametri- na, dimethenoamide dimethenoamide-P, dimethipine, dimetrasulfuron, dinitramine, dinoseb, dinoterb, difenoamide, dipropetrin, diquat, diquat dibromide, dithiopyr, diuron, DNOC, eglinazinea-ethyl, endothal, EPTC, esprocarb, etalfluralin, etamethsulfuron , ethametsulfuron- methyl, ethephone, ethidimurons, ethiozins, etofumesate, ethoxyphene, ethoxyphenethyl, ethoxysulfuron, ethobenzanide, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl )-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenoyl]-ethansulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl) -1H- benozimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H, 3H)- dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, phenoxasulfone, phenotrazamide, fenurone, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florassulamus, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenoacet (thiafluamide), flufenopyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropin, fluometurone, fluordifen, fluorglycofen, fluorglyco-phenoethyl, flupoxam, flupropacil, flupropanate , flupyrsulfuron, flu-pyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluro-chloroidone, fluroxypyr, fluroxypyr-methyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, famasafen, foramsulfuron, for-chlorofenurone , fosamine, furyloxyfene, gibberylic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, ie, O-(2,4 -dimethyl-6-nitrophenoyl)-O-ethyl-isopropylphosphoramidothioate, halosaphene, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P- methyl, hexazinone, HW-02, ie, 1-(dimethoxyphosphoryl)-ethyl (2,4-dichlorophenoxy)acetate, imazametabenz, imazametabenz-methyl, ima- zamox, imazamox-ammonium, imazapic, imazapyr, imazapyr- isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazetapyr-ammonium, imazosulfuron, inabenofide, indanophane, indaziflam, indole acetic acid (IAA), 4-indole-3-isobutyric acid (IBA), iodosulfurone, iodosulfuron-methyl-sodium, ioxynyl, ipfenocarbazone, isocarbamide, isopropaline, isoproturone, isourone, isoxaben, isoxachlorotol, isoxaflutole, isoxapirifop, KUH-043, ie, 3-({[5-(difluoromethyl)-1-methyl- 3-(trifluoromethyl)-1H -pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, carbylate, ketospiradox, lactophen, lenoacyl, linaurone, maleic hydrazide, MCPA, MCPB, MCPB -methyl, -ethyl and -sodium, meco-prop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenocet, mefluidide , mepiquat chloride, mesosulfuron, methyl mesosulfuron, mesotrione, mehabenzthiazuron, metam, metamifop, metamitrone, metazachlor, metazasulfuron, methazol, methiopyrsulfuron, methiozoline, methoxyphenone, methyldimrone, 1-methylcyclopropene, methylisothiocyanate, metobenozurone, bromurona , metolachlor, S-metolachlor, metossulam, methoxurone, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrosulfate, monolinuron, monosulfuron, monosulfuron ester, monuron, MT 128, i.e. , 6-chloro-N-[(2E)-3-chloroprop-2-ene-1-yl]-5-methyl-N-phenoylpyridazin-3-amine, MT-5950, i.e. N-[3-chloroyl-4 -(1-methylethyl)-phenoyl]-2-methylpentanamide, NGGC-011, na-proanilide, napropamide, naptalamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburone , nicosulfuron, nipyraclofen, nitraline, nitrofen, sodium nitrophenolate (mixture of isomers), nitrofluorfen, nonanic acid, norflurazone, orbenocarb, orthosulfamurone, orzaline, oxadiaclay, oxadiazone, oxasulfuron, oxaziclomephone, oxyfluorfen, paclobutrazol, paraquat, paraquat-dichloride, pelargonic acid (nonanic acid), pendimethalin, pendralin, penoxsula, pentanochlor, pentoxazone, perfluidone, petoxamide, phenisopham, phenomedipham, phenomediphamo-heylyl, picloram, picolinaphene, pinoxadene, piperofos, pyrifenop, pyrifenop-butyl , pretilachlor, primisulfuron, methyl primisulfuron, probenazole, profluazole, procyazine, prodiamine, prifluralin, profoxydime, prohexadione, prohexadione-calcium, prohydrojasmon, prometone, promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor , propoxycarbazone, propoxycarbazone-sodium, propyrsulfuron, propyzamide, prosulfaline, prosulfocarb, prosulfuron, prinachlor, pyraclonil, pyraflufen, pyrafluphenethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifene, piribambenoz, ibambenoz- isopropyl, piribambenoz-propyl, piribenozoxime, piributicarb, pyridafol, pyridate, pyrifthalide, piriminobac, piriminobac-methyl, pyrimisulfan, piritiobac, pyritiobac-sodium, pyroxasulfone, piroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop- ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, safluphenoacyl, secbumetone, sethoxydime, sidurone, simazine, symethrin, SN- 106279, i.e. methyl-(2R)-2({ 7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate, sulcotrione, sulfate (CDEC), sulfenotrazone, sulfometurone, sulfometurone-methyl, sulfosate (glyphosate-trimmesic), sulfosulfuron, SYN-523 , SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-ene-2-yl-5-[2-chloro-4-(trifluoromeyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benozoxazin-6-yl]-3- propyl-2-thioxoimidazolidine-4,5-dione, tebutame, tebutiurone, technazene, tefuryltrione, tembotrione, tepraloxidime, terbacyl, terbucarb, terbuchlor, terbumetone, terbuthylazine, terbutrine, tenoylchloro, thiafluamide, thiazaflurone, thiazopyr, thidiazimin, thidiazurone, thienocarbazone, thienocarbazone-methyl, thiphenosulfurone, thiphenosulfurone-methyl, thiobenocarb, thiocarbazil, topramezone, tralkoxidime, triallate, triasulfuron, triaziflam, triazofenamide, tribenurone, tribenurone-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, triethazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturone, trinaxapac, trinaxapac-ethyl, tritosulfurone, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862 i.e. 3,4- dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, and also the following compounds:

[0098] For application, the formulations present in commercial form are optionally diluted in the usual way, for example, in spray powders, emulsifiable concentrates, dispersions and water-dispersible granules, by means of water. Preparations in the form of powders, granules for soil or spraying, as well as sprayable solutions are normally no longer diluted with other inert substances before application.

[0099] With external conditions, such as temperature, humidity, the type of herbicide used, among others, the necessary amount of application of the compounds of formula (I) varies. It can vary within wide limits, for example, between 0.0001 and 1.0 kg/ha or more of active substance, preferably, however, it is between 0.005 and 750 g/ha.

[00100] The examples below explain the invention.

A. Chemical Examples 1. Synthesis of 4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1 -dioxide (example from table No. 1928)

[00101] 1.00 g (3.14 mmol) of 4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide and 0.33 g (3 .15 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature (RT) in 35 ml of CH2Cl2, 3.02 g (4.74 mmol) of 2.4 ,6-tripropyl-1,3,5,2,4,6-trioxatrifosphinan 2,4,6-trioxide (50% solution in THF) was added and the mixture was stirred at RT for 1 h. Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61 mmol) of 4-dimethylaminopyridine (DMAP) were added and the entire mixture was stirred at RT for 16 h. This was followed by washing with water and twice with 6N hydrochloric acid, drying the organic phase over Na2SO4 and suction filtration through silica gel, thorough washing with 1:2 heptane/athylacetatol and concentration. Yield 708 mg (63%). 1H NMR (CDCl3): δ = 2.44 (s,3H), 3.53 (s,3H), 3.57 (dd,1H), 3.71 (d,1H), 5.15 (d, 1H), 7.55 (d,1H), 7.74 (d,1H), 9.40 (s,1H) 2. Synthesis of 4-chloro-N-(1-methyl-1H-1,2, 4-triazol-5-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide (example from table No. 1545)

[00102] 0.80 g (3.24 mmol) odef 4-chloro-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide, 0.72 g (2.43 mmol) of di(1-methyl-1H-1,2,4-triazol-5-amine) sulfate and 20 mg (0.164 mmol) of DMAP were initially loaded into 5 ml of pyridine, 0.65 g (5.35 mmol) of thionyl chloride were added and the mixture was stirred at 70°C for 1 h. Subsequently, 0.5 ml of water was added, and the mixture was stirred for another 30 min, acidified with saturated KHSO4 solution and extracted three times, in each case, with 100 ml of ethyl acetate. The combined organic phases were washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica gel, heptane/acetic ester). Yield 642 mg (61%). 1H NMR (DMSO-d6): δ = 3.40 (t,2H), 3.74 (t,2H), 3.79 (s,3H), 7.89 (br,3H), 11.39 ( s,1H) 3. Synthesis of N-(1-ethyl-1H-tetrazol-5-yl)-4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxamide 1 ,1-dioxide (example table No. 189)

[00103] 1.00 g (3.54 mmol) of 4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxylic acid 1,1-dioxide, 0.63 g (5.32 mmol) of 1-ethyl-5-aminotetrazol and 23 mg (0.188 mmol) of DMAP were initially loaded into 7 ml of pyridine, 0.71 g (5.86 mmol) of thionyl chloride were added and stirred. for 1 h at 70°. Subsequently, 0.5 ml of water was added, stirred additionally for 30 min, acidified with saturated KHSO4 solution and extracted three times, in each case, with 100 ml of ethyl acetate. The combined organic phases were washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica gel, heptane/acetic ester). Yield 492 mg (37%). 1H NMR (CDCl3): δ = 1.56 (s,6H), 1.64 (t,3H), 2.36 (dd,2H), 2.65 (s,3H), 2.77 (s, 3H), 3.43 (dd,2H), 4.46 (q,2H), 7.37 (s,3H), 10.16 (s,1H)

[00104] The examples listed in the tables below were prepared analogously to the above-mentioned methods or are obtainable analogously to the above-mentioned methods. The compounds listed in the tables below are especially preferred. The abbreviations used mean: Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph =phenyl Table 1: Compounds according to the invention of general formula (I), in which Q represents Q1, Y represents S(O)m, R5 represents hydrogen and n represents 2 Table 2: Compounds according to the invention of formula (I), in which Q represents Q2, Y represents S(O)m, R5 represents hydrogen and n represents 2 Table 3: Compounds according to the invention of formula (I), in which Q represents Q3, Y represents S(O)m, R5 represents hydrogen and n represents 2 Table 4: Compounds according to the invention of formula (I), in which Q represents Q1, R5 represents hydrogen and represents 1 Table 5: Compounds according to the invention of formula (I), in which Q represents Q2, R5 represents hydrogen and en represents 1 Table 6: Compounds according to the invention of formula (I), in which Q represents Q3, R5 represents hydrogen and n represents 1 Table 7: Compounds according to the invention of formula (I), in which Q represents Q1, X and Y represent, in each case, oxygen, R5 represents fluorine and n represents 1 Table 8: Compounds according to the invention of formula (I), in which Q represents Q3, Y represents 2-(1,4-pyrazinyl)oxymethyl, Y represents SO2, R5 represents hydrogen and represents 2 Table 9: Compounds according to the invention of formula (I), in which Q represents Q1, Y represents SO2, R5 represents hydrogen and n represents 1 Table 10: Compounds according to the invention of formula (I), in which Q represents Q1, R5 represents hydrogen and en represents 1 Table 11: Compounds according to the invention of formula (I), in which Q represents Q2, R5 represents hydrogen and represents 1 Table 12: Compounds according to the invention of formula (I), in which Q represents Q3, R5 represents hydrogen and n represents 1 Table 13: Compounds according to the invention of formula (I), in which Q represents Q1, R5 represents hydrogen and represents 2 Table 14: Compounds according to the invention of formula (I), in which Q represents Q2, R5 represents hydrogen and represents 2 Table 15: Compounds according to the invention of formula (I), in which Q represents Q3, R5 represents hydrogen and n represents 2

B. Formulation examples a) Dusting agents

[00105] A dusting agent is obtained by mixing 10 parts by weight of a compound of general formula (I) and 90 parts by weight of talc as an inert substance and grinding them in a percussion mill. b) A wettable powder, easily dispersible in water, is obtained by mixing 25 parts by weight of a compound of general formula (I), 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as crosslinking and dispersing agent and grinding the same in a cob disc mill. c) A dispersion concentrate easily dispersible in water is obtained by mixing 20 parts by weight of a compound of general formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (®Triton X207 ), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, e.g., about 255 to above 277°C) and grinding the mixture in a ball mill for a fineness of below 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula (I) and/or the same, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of nonylphenol, oxethylated as emulsifier. e) Water dispersion granules are obtained by mixing f) parts by weight of a compound of general formula (I) and/or salts thereof, g) parts by weight of calcium ligninsulfonate, h) parts by weight of sodium lauryl sulfate, i) parts by weight of polyvinyl alcohol and j) parts by weight of kaolin, grinding the mixture in a pin mill and granulating the powder into a fluidized layer by spraying over water as the granulation liquid. f) Granules for dispersion in water are also obtained by homogenizing and previously grinding 25 parts by weight of a compound of general formula (I) and/or salts thereof, 5 parts by weight of 2,2-dinaphthylmethane sodium -6,6'-disulfonate, 2 parts by weight of oleoylmethyltaurate solid, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water in a colloidal mill, subsequently grinding mixing in a pearl mill and pulverizing and drying the suspension thus obtained in a spray tower by means of a one-component nozzle.

C. Biological examples 1. Herbicidal effect against harmful plants in pre-emergence

[00106] Weed seeds and mono- and dicotyledonous crop plants are placed in wood fiber pots in sandy clay soil and covered with earth. The compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the covering soil as an aqueous suspension or emulsion, with an application amount of water equivalent to 300 to 800 l/ha (converted), with the addition of 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and kept under good growing conditions. Damage to test plants is assessed visually, after a 3-week test period, compared to untreated controls (herbicidal activity in percent (%): 100 action = plants died, 0% action = such as the control plants). For example, compounds No. 7, 9, 40, 187 and 189, at an application rate of 320 g/ha show, in each case, at least 80% efficacy against Abutilon teofrasti and Amarantus retroflexus. Compounds No. 9, 40, 187, 189 and 2204, at an application rate of 320 g/ha, show, in each case, at least 80% efficacy against Matricaria odorless, Stellaria media and Veronica persica.

2. Post-emergence herbicidal action against harmful plants

[00107] Seeds of weeds and monocotyledonous and dicotyledonous crop plants are placed in sandy clay soil in wood fiber pots, covered with soil, and grown in a greenhouse under good growing conditions. Two to three weeks after sowing, test plants are treated at the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants as an aqueous suspension or emulsion, at an application amount of water. 600 to 800 l/ha (converted), with the addition of 0.2% wetting agent. After the test plants have been left in the greenhouse under optimal growth conditions for about 3 weeks, the action of the formulations is assessed visually in comparison with untreated controls (herbicidal action in percent (%): 100% action = plants died, 0% action = just like control plants).

[00108] Examples of good post-emergency (PO) effectiveness. For example, compounds No. 7 and 2204, at an application rate of 80 g/ha, show, in each case, at least 80% efficacy against Abutilon teofrasti and Viola tricolor. Compounds No. 9, 187 and 189, at an application rate of 80 g/ha show, in each case, at least 80% efficacy against Abutilon teofrasti and Amarantus reflexus, Compounds No. 40, 187 and 189, at an application quantity of 80 g/ha shows, in each case, at least 80% effectiveness against Matricaria inodora, Stellaria media and Veronica persica.

Claims (10)

1. N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloaryl carboxamide, or a salt thereof, characterized by fact that it is selected from the group consisting of: 2. Herbicidal composition, characterized by the fact that it comprises a herbicidally active amount of at least one compound, as defined in claim 1. 3. Herbicidal composition according to claim 2, characterized by the fact that it is in a mixture with formulation adjuvants. 4. Herbicidal composition according to claim 2 or 3, characterized in that it comprises an antidote. 5. Herbicidal composition according to claim 4, characterized by the fact that the antidote is selected from the group consisting of cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl. 6. Herbicidal composition according to one of claims 2 to 5, characterized in that it further comprises another herbicide. 7. Method for controlling undesirable plants, characterized by the fact that it comprises applying an effective amount of at least one compound, as defined in claim 1, or of a herbicidal composition, as defined in any one of claims 2 to 6, to the plants or to the location of undesirable vegetation. 8. Use of compounds, as defined in claim 1, or herbicidal compositions, as defined in any one of claims 2 to 6, characterized by the fact that it is to control undesirable plants. 9. Use according to claim 8, characterized in that the compounds are used to control undesirable plants in useful plant crops. 10. Use according to claim 9, characterized in that the useful plants are transgenic useful plants.