EP3068772A1 - 2-hetaryl-pyridazinone derivatives and their use as herbicides - Google Patents

2-hetaryl-pyridazinone derivatives and their use as herbicides

Info

Publication number
EP3068772A1
EP3068772A1 EP14796087.6A EP14796087A EP3068772A1 EP 3068772 A1 EP3068772 A1 EP 3068772A1 EP 14796087 A EP14796087 A EP 14796087A EP 3068772 A1 EP3068772 A1 EP 3068772A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
halo
heterocyclyl
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP14796087.6A
Other languages
German (de)
French (fr)
Inventor
Ralf Braun
Christian Waldraff
Ines Heinemann
Arnim Köhn
Hartmut Ahrens
Alfred Angermann
Stephen David Lindell
Dirk Schmutzler
Hansjörg Dietrich
Christopher Hugh Rosinger
Elmar Gatzweiler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP14796087.6A priority Critical patent/EP3068772A1/en
Publication of EP3068772A1 publication Critical patent/EP3068772A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • WO2013 / 083774 A1 describes pyridazinones as herbicides. However, these drugs do not always show a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important
  • Crops such as cereals, corn and rice.
  • Object of the present invention is to provide alternative herbicidal active ingredients. This task is described by the following
  • An object of the present invention are thus 2-hetaryl-pyridazinone derivatives of the formula (I) or salts thereof
  • Q is Q 1 or Q 2 ,
  • R 1 denotes hydrogen, halogen, cyano, amino, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkyl, C 6 ) alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -
  • R 3 is hydrogen, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S-carbonyl, Arylcarbonyl or aryl-S (O) n , where the latter two radicals are each substituted by s radicals R 4 , R 4 is halogen, (Ci-C) alkyl, halogeno (Ci-C) alkyl or (Ci -C) -alkoxy,
  • X 1 is N or CZ 1 ,
  • X 2 is N or CW
  • X 3 is N or CR 5 ,
  • X 4 is N or CY 2
  • Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (C 1 -C 6 ) -Alkyl-S (O) n R 7 , (
  • Y 2 is hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C3-C6) cycloalkyl , (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R
  • radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl and
  • Z 1 is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3 -C 6) cycloalkyl, (Ci-C6) -alkyl- (C3-C6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl - (C 1 -C 6 ) -alkyl, COR 6 , COOR 6
  • Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, halo (C 2 -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (Ci-C6) -alkyl- (C3-C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, OR 6 , OCOOR 6 , NR 6 COOR 6 ,
  • W is hydrogen, halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, ( C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C6) alkyl, (Ci-C 4) alkoxy or (Ci-C 4) haloalkoxy, or Z 1 or Z 2, and W together with the two carbon atoms to which they are attached form a five- or six-membered
  • R 5 is hydrogen, halogen, (C 1 -C 4) -alkyl, halogeno (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy,
  • R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl
  • R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl,
  • R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl,
  • R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2 , 3, 4, 5 or 6.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl.
  • alkenyl means e.g. Allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring.
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl
  • Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring.
  • 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,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • the invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • the compounds of formula (I) can form salts. Salt formation can through
  • Suitable bases are organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates
  • Suitable cation for example metal salts, in particular alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • metal salts in particular alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
  • Q is Q 1 or Q 2 ,
  • R 1 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, (C 2 - C 6) alkynyl, (C3-C 6) Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
  • R 2 is hydrogen, halogen, cyano, (Ci-C6) alkyl, halo (Ci-C6) alkyl, (C2-C6) alkenyl, (C 2 -C 6) -alkynyl or (Ci-C 6 ) -alkyl-S (O) n ,
  • R 3 is hydrogen
  • R 4 is halogen, (C 1 -C 4 ) -alkyl, halogeno (C 1 -C 4 ) -alkyl or (C 1 -C 4) -alkoxy, X 1 is N or CZ 1 , X 2 is N or CW, X 3 is N or CH, X 4 is N or CY 2 ,
  • Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl
  • Y 2 is hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, halo (C 2 -C 6) alkenyl, ( C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6) - alkyl-S (O)
  • Z 1 represents hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ -CycloalkyKCi-Ce) - alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, -OCOOR 6, NR 6 COOR 6, C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C
  • Heterocyclyl carries n oxo groups
  • Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C2-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C ( O) N (R 6 ) 2 , OC (O) N (
  • R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) al
  • R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocycly
  • R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl or phenyl, R 9 represents (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl or phenyl,
  • R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3, 4, 5 or 6.
  • R 1 is hydrogen, (C 1 -C 4) -alkyl, (C 2 -C 6) -alkenyl, propargyl, cyclopropyl or S (O) n CH 3 ,
  • R 2 is hydrogen
  • R 3 is hydrogen, X 1 is N or CZ 1 ,
  • X 2 is N or CW
  • X 3 is N or CH
  • Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, OR 6, S (O) n R 7, (Ci-C 6) -Alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , (C 1 -C 6 ) -alkyl heteroaryl or (Ci C6) -alkyl heterocyclyl, where the latter two radicals are each represented by s radicals from the group consisting of halogen, (Ci-C
  • Heterocyclyl carries n oxo groups
  • W is hydrogen, halogen, (C 1 -C 4 ) -alkyl
  • R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl Heteroaryl, Heterocycl, (Ci-C 6) alkyl-heter
  • R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (Cs-CeJ-cycloalkylene alkyl, (C 3 - C 6) Cycloalkenyl, (C 1 -C 6) -alkyl-O- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkyl,
  • Phenyl phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl-NR 3 -heteroaryl or (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are each represented by s radicals from the group consisting of cyano, halogen, nitro,
  • Rhodano OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 ,
  • R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl,
  • R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6.
  • substituents and symbols unless otherwise defined, have the same meaning as described for formula (I).
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology.
  • IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology.
  • a number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the invention have an excellent herbicidal
  • Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the seeds eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds
  • the area on which the plants grow eg the acreage
  • the compounds of the invention for example in Vorsaat- (possibly also by Incorporation into the soil), pre-emergence or post-emergence procedures.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be named, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • Crops such as agricultural crops or ornamental plantings.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special special traits for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Properties relate eg to the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others Fatty acid composition of the crop known.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
  • Ornamental plants e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
  • the compounds of the invention as herbicides in
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops characterized by a combination z. B. the o. G.
  • Numerous molecular biological techniques with which new transgenic plants with altered properties can be produced are known in principle, see, for example, BI 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).
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in to cause the cells an antisense effect. 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.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • DNA sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106).
  • Expression of the nucleic acid molecules can also be found in the
  • transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD Hydroxyphenylpyruvat dioxygenases
  • Harmful plants In the application of the active compounds according to the invention in transgenic cultures, in addition to the effects to be observed in other cultures Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
  • the compounds of the invention may be in the form of wettable powders
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
  • EC emulsifiable concentrates
  • EW emulsions
  • Water-in-oil emulsions sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents such as butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: 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, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
  • the formulations present in commercially available form are optionally diluted in customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
  • Solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • the following examples illustrate the invention.
  • 5-Bromo-4-methoxy-2- (5- (trifluoromethyl) pyridine-1-oxide-2-yl) pyridazin-3-one (5 mmol, crude) in 15 ml of DMF are treated with 7 ml (50 mmol) of trifluoroacetic anhydride added and stirred at 90 ° C for 3h. The mixture is then poured onto ice-water and extracted with ethyl acetate. The organic phase is washed several times with water and sat. Washed brine, dried and the solvent removed in vacuo. The residue 5-bromo-4-methoxy-2- (3- (trifluoromethyl) pyrid-2-on-6-yl) pyridazin-3-one is used without further purification in the next step.
  • Q 1 , R 2 and R 3 are each hydrogen, and X 1 is CZ 1 , X 2 is CH and X 3 is CH.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by adding 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • a water-dispersible granules are obtained by
  • a water-dispersible granule is also obtained by
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • the compound no. 1 -3 at an application rate of 80 g / ha at least 80% effect against Echinochloa crus galli, Seta a viridis, Matricaria inodora, Ipomoea purpurea, Stellaria media, Viola tricolor, Amaranthus retroflexus and Veronica persica.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to 2-hetaryl-pyridazinone derivatives of general formula (I) as herbicides. In said formula (I), R1, R2 and R3 are groups such as hydrogen, organic groups such as alkyl, and other groups such as halogen. Q is a substituted heterocycle.

Description

2-Hetaryl-Pyridazinonderivate und ihre Verwendung als Herbizide  2-hetaryl-pyridazinone derivatives and their use as herbicides
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
Nutzpflanzenkulturen. Crops of useful plants.
Aus WO2013/083774 A1 sind Pyridazinone als Herbizide beschrieben. Allerdings zeigen diese Wirkstoffe nicht immer eine ausreichende Wirkung gegen Schadpflanzen und/oder sie sind zum Teil nicht ausreichend verträglich mit einigen wichtigen WO2013 / 083774 A1 describes pyridazinones as herbicides. However, these drugs do not always show a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important
Kulturpflanzen, wie Getreidearten, Mais und Reis. Crops such as cereals, corn and rice.
Aufgabe der vorliegenden Erfindung ist es, alternative herbizid wirksame Wirkstoffe bereitzustellen. Diese Aufgabe wird durch die nachfolgend beschriebenen Object of the present invention is to provide alternative herbicidal active ingredients. This task is described by the following
erfindungsgemäßen Pyridazinon-derivate gelöst. dissolved pyridazinone derivatives according to the invention.
Ein Gegenstand der vorliegenden Erfindung sind somit 2-Hetaryl-Pyridazinonderivate der Formel (I) oder deren Salze An object of the present invention are thus 2-hetaryl-pyridazinone derivatives of the formula (I) or salts thereof
worin wherein
Q bedeutet Q1 oder Q2, Q is Q 1 or Q 2 ,
R1 bedeutet Wasserstoff, Halogen, Cyano, Amino, (Ci-C6)-Alkyl, Halogen-(Ci-C6)- alkyl, (C2-C6)-Alkenyl, (C2-C6)-Cycloalkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C3)-alkyl, (Ci-C6)-R 1 denotes hydrogen, halogen, cyano, amino, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkyl, C 6 ) alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -
Al koxy-(C2-C6)-al koxy, (Ci -C6)-Al koxy-(C2-C6)-al koxy-(Ci -C3)-al kyl , (Ci -C6)-Al kyl-S(O)n, Halogen-(Ci-C6)-alkyl-S(O)n, (Ci-C6)-Alkyl-S(O)n-(Ci-C3)-alkyl, Halogen-(Ci-C6)-alkyl- S(O)n-(Ci-C3)-alkyl, (Ci-C6)-Alkylamino oder (Ci-CeJ-Dialkylamino, R2 bedeutet Wasserstoff, Halogen, Cyano, Hydroxy, Nitro, Amino, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkyl-S(O)n, Halogen-(Ci-C6)-alkyl- S(O)n, (Ci-C6)-Alkyl-S(O)n-(Ci-C3)-alkyl, Halogen-(Ci-C6)-alkyl-S(O)n-(Ci-C3)-alkyl, (Ci- C6)-Alkylamino oder (Ci-C6)-Dialkylamino, Al alkoxy- (C 2 -C 6) -al koxy, (Ci-C6) alkoxy- -Al (C 2 -C 6) -al alkoxy- (Ci -C 3) -alkyl, (C 6 -C ) -Alkyl-S (O) n , halo (C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S (O) n - (C 1 -C 3 ) -alkyl , Halogen- (C 1 -C 6 ) -alkyl- S (O) n - (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -alkylamino or (C 1 -C 16 -dialkylamino, R 2 denotes hydrogen, halogen, cyano, hydroxy, nitro, amino, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-Ce) alkoxy, (Ci-C 6) alkyl-S (O) n, halo ( C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S (O) n - (C 1 -C 3 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl-S (O) n - (C 1 -C 3 ) -alkyl, (C 1 -C 6) -alkylamino or (C 1 -C 6) -dialkylamino,
R3 bedeutet Wasserstoff, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Alkoxycarbonyl, (Ci-C6)- Alkyl-S(O)n, (Ci-C6)-Alkyl-S-carbonyl, Arylcarbonyl oder Aryl-S(O)n bedeutet, wobei die zwei letztgenannten Reste jeweils durch s Reste R4 substituiert sind, R4 bedeutet Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci-C )-Alkoxy, R 3 is hydrogen, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S-carbonyl, Arylcarbonyl or aryl-S (O) n , where the latter two radicals are each substituted by s radicals R 4 , R 4 is halogen, (Ci-C) alkyl, halogeno (Ci-C) alkyl or (Ci -C) -alkoxy,
X1 bedeutet N oder CZ1, X 1 is N or CZ 1 ,
X2 bedeutet N oder CW, X 2 is N or CW,
X3 bedeutet N oder CR5, X 3 is N or CR 5 ,
X4 bedeutet N oder CY2, Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)- Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (C1-C6)- Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)- alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, X 4 is N or CY 2 , Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (C 1 -C 6 ) -Alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , ( C 1 -C 6 -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl CN, (Ci-C 6) alkyl-SO 2 N (R 6) 2, (Ci-C 6) - alkyl-NR 6 COR 6, (Ci-C 6) alkyl-NR 6 SO 2 R 7, CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the last three radicals each are by s radicals from the group consisting of halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (Ci -Ce) alkoxy, halo (Ci-Ce) - alkoxy, and wherein Heterocycly l carries oxo groups,
Y2 bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, CO(NOR1)R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (Ci-C6)-Alkyl- S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)- Alkyl-CO2R1, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (C1- C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)- Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die sechs Y 2 is hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C3-C6) cycloalkyl , (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , CO (NOR 1 ) R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 (C 1 -C 6 ) -alkyl-S (O) n R 2, (Ci-C 6) alkyl-OR 1, (Ci-C 6) alkyl-OCOR 1, (Ci-C 6) alkyl-OSO2R 2, (Ci-C 6) - alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-CN, (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) - Alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P ( O) (OR 5) 2, CH 2 P (O) (OR 5) 2, (Ci-C 6) -alkyl-phenyl, (Ci-C 6) alkyl-heteroaryl, (Ci-C 6) - alkyl Heterocyclyl, phenyl, heteroa Ryl or heterocyclyl, wherein the six
letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl und the last-mentioned radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl and
Cyanomethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Ci-C6)-alkyl-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)- Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Cyanomethyl substituted, and heterocyclyl wherein n transmits oxo groups, Z 1 is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3 -C 6) cycloalkyl, (Ci-C6) -alkyl- (C3-C6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl - (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 . OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 1 , (Ci-C 6) - alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) -alkyl-SO 2 OR 6, (Ci-C 6) alkyl -CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each represented by s radicals selected from the group consisting of halogen, nitro, cyano, ( Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) - Alkoxy and halogeno (Ci-C6) -alkoxy are substituted, and whereby Heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
Z2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (Ci-C6)-alkyl-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen- (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, halo (C 2 -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (Ci-C6) -alkyl- (C3-C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, OR 6 , OCOOR 6 , NR 6 COOR 6 ,
C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (Ci-C 6) -alkyl-OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals mentioned are each represented by s radicals selected from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6 ) -alkoxy, and wherein heterocyclyl n
Oxogruppen trägt, W bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-Alkoxy oder (Ci-C4)-Haloalkoxy, oder Z1 oder Z2 und W bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t W is hydrogen, halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, ( C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C6) alkyl, (Ci-C 4) alkoxy or (Ci-C 4) haloalkoxy, or Z 1 or Z 2, and W together with the two carbon atoms to which they are attached form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C6)-alkyl substituiert ist, Carbon atoms and p heteroatoms from the group consisting of N, O and S, where this ring is represented by q radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) - alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy and (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl,
R5 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci- C )-Alkoxy, R 5 is hydrogen, halogen, (C 1 -C 4) -alkyl, halogeno (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl-R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl
Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8- Heterocyclyl, wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl NR 8 -heteroaryl or (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl, where the 21 latter radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl,R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl,
Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl-NR 3 -heteroaryl or (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl, where these 17 radicals consist of s radicals from the group from cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci-C) alkoxy- (C 2 -C 6 ) alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Al kinyl oder Phenyl, R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl,
R10 bedeutet (Ci-C4)-Al kyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2 , 3, 4, 5 or 6.
In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl. Analog bedeutet Alkenyl z.B. Allyl, 1 -Methylprop-2-en-1 -yl, In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl. Analogously, alkenyl means e.g. 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 und 1 -Methyl-but-2-en-1 -yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1 -yl, But-3-in-1 -yl, 1 -Methyl-but-3-in-1 -yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Analog bedeutet Cycloalkenyl eine monocyclische Alkenylgruppe mit drei bis sechs Kohlenstoffringgliedern, z.B. Cyclopropenyl, Cyclobutenyl, 2-methylprop-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. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can each be in any position of the unsaturated radical. Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
Cyclopentenyl und Cyclohexenyl, wobei sich die Doppelbindung an beliebiger Position befinden kann. Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
Halogen steht für Fluor, Chlor, Brom oder lod. Halogen is fluorine, chlorine, bromine or iodine.
Heterocyclyl bedeutet einen gesättigten, teilgesättigten oder vollständig ungesättigten cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring annelliert sein kann. Beispielsweise steht Heterocyclyl für Piperidinyl, Pyrrolidinyl, Tetrahydrofuranyl, Dihydrofuranyl und Oxetanyl, Heteroaryl bedeutet einen aromatischen cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring annelliert sein kann. Beispielsweise steht Heteroaryl für 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, 1 H-1 ,2,3,4-Tetrazolyl, 1 ,2,3,4-Oxatriazolyl, 1 ,2,3,5-Oxatriazolyl, 1 ,2,3,4-Thiatriazolyl und 1 ,2,3,5-Thiatriazolyl. Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl, Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by 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, 1 H-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.
Ist eine Gruppe mehrfach durch Reste substituiert, so ist darunter zu verstehen, daß diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. If a group is repeatedly substituted by radicals, it is to be understood that this group is substituted by one or more identical or different radicals.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn n für 1 steht Diastereomers occur. Likewise, stereoisomers occur when n is 1
(Sulfoxide). Stereoisomere lassen sich aus den bei der Herstellung anfallenden(Sulfoxides). Stereoisomers can be obtained from the resulting in the preparation
Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Mixtures according to customary separation methods, for example by chromatographic separation methods obtained. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Auxiliaries are selectively produced. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
Die Verbindungen der Formel (I) können Salze bilden. Salzbildung kann durch The compounds of formula (I) can form salts. Salt formation can through
Einwirkung einer Base auf Verbindungen der Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate Effect of a base on compounds of formula (I) take place. Examples of suitable bases are organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates
und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are
Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (Ci- C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Compounds in which the acidic hydrogen is used for agriculture is replaced by suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Preference is given to compounds of the general formula (I) in which
Q bedeutet Q1 oder Q2, Q is Q 1 or Q 2 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder (Ci-Ce)-Alkoxy- (Ci-C6)-alkyl, R 1 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, (C 2 - C 6) alkynyl, (C3-C 6) Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
R2 bedeutet Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder(Ci-C6)-Alkyl-S(O)n, R 2 is hydrogen, halogen, cyano, (Ci-C6) alkyl, halo (Ci-C6) alkyl, (C2-C6) alkenyl, (C 2 -C 6) -alkynyl or (Ci-C 6 ) -alkyl-S (O) n ,
R3 bedeutet Wasserstoff, R 3 is hydrogen,
R4 bedeutet Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci-C )-Alkoxy, X1 bedeutet N oder CZ1, X2 bedeutet N oder CW, X3 bedeutet N oder CH, X4 bedeutet N oder CY2, R 4 is halogen, (C 1 -C 4 ) -alkyl, halogeno (C 1 -C 4 ) -alkyl or (C 1 -C 4) -alkoxy, X 1 is N or CZ 1 , X 2 is N or CW, X 3 is N or CH, X 4 is N or CY 2 ,
Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-C6)- alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) - Alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl- Heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the three last-mentioned radicals are in each case represented by s radicals from the group consisting of halogen, cyano, nitro, (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6 ) -alkoxy, and where heterocyclyl carries n oxo groups,
Y2 bedeutet Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)- Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3- C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)- Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (C1- C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (C1- C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y 2 is hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, halo (C 2 -C 6) alkenyl, ( C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6) - alkyl-S (O) n R 7, (Ci-C 6) -alkyl-OR 6, (Ci-C 6) alkyl-OCOR 6, (Ci-C 6) alkyl -OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the three last-mentioned radicals are each represented by s radicals from the group consisting of halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (Ci -Ce) alkoxy and halo (Ci-C6) -alkoxy are substituted, and wob carries heterocyclyl n oxo groups,
Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (C1- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z 1 represents hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ -CycloalkyKCi-Ce) - alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, -OCOOR 6, NR 6 COOR 6, C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl -OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) -Alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl -NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, H alogen- (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (Ci-C 6) - alkyl, (Ci-C6) alkoxy and halo (Ci-C6) -alkoxy are substituted, and wherein
Heterocyclyl n Oxogruppen trägt, Z2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)- Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci- C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, W bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, Heterocyclyl carries n oxo groups, Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C2-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C ( O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6) 2, NR 6 SO 2 R 7, NR 6 COR 6, (Ci-C 6) - alkyl-S (O) n R 7, (Ci-C 6) -alkyl-OR 6, (Ci- C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (Ci C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C C 6 ) alkyl, halo (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl , (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6 ) -alkoxy, and where heterocyclyl carries n oxo groups, W denotes hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl , (C 2 -C 6) - alkenyl, (C2-C6) -alkynyl, (C3-C6) -cycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C) haloalkoxy,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8- Heterocyclyl, wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl-NR 8 heteroaryl or (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl, where the 21 last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci- C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl -O-heterocyclyl, C 6) -alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl are substituted, and where heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl or phenyl, R 9 represents (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0, 1 , 2, 3, 4, 5 oder 6. R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3, 4, 5 or 6.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
Q bedeutet Q1, Q is Q 1 ,
R1 bedeutet Wasserstoff, (Ci-C )-Alkyl, (C2-C )-Alkenyl, Propargyl, Cyclopropyl oder S(O)nCH3, R 1 is hydrogen, (C 1 -C 4) -alkyl, (C 2 -C 6) -alkenyl, propargyl, cyclopropyl or S (O) n CH 3 ,
R2 bedeutet Wasserstoff, R 2 is hydrogen,
R3 bedeutet Wasserstoff, X1 bedeutet N oder CZ1, R 3 is hydrogen, X 1 is N or CZ 1 ,
X2 bedeutet N oder CW, X3 bedeutet N oder CH, X 2 is N or CW, X 3 is N or CH,
Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, OR6, S(O)nR7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, (Ci-C6)-Alkyl-Heteroaryl oder (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die 3 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, OR 6, S (O) n R 7, (Ci-C 6) -Alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , (C 1 -C 6 ) -alkyl heteroaryl or (Ci C6) -alkyl heterocyclyl, where the latter two radicals are each represented by s radicals from the group consisting of halogen, (Ci-C6) alkyl, halogeno (Ci-C6) alkyl, S (O) n - (Ci -C 6) alkyl, (C 1 -C 6) alkoxy and halo (C 1 -C 6) alkoxy, and wherein heterocyclyl carries n oxo groups, Z 1 represents hydrogen, halogen, cyano, rhodano, nitro, (C 1 -C 6 ) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo ( C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce) - alkyl, halo (C3-C6) - cycloalkyl- (C 1 -C 6 ) alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7, NR 6 COR 6, (Ci-C 6) alkyl-S (O) n R 7, (Ci-C 6) -alkyl-OR 6, (Ci-C 6) - alkyl -OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (Ci- C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -Alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the 3 latter radicals are each represented by s radicals selected from the group consisting of halogen, nitro , cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (Ci-C 6) - alkyl, (Ci- C 6) alkoxy and halo (C 1 -C 6) alkoxy, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
W bedeutet Wasserstoff, Halogen, (Ci-C4)-Alkyl, W is hydrogen, halogen, (C 1 -C 4 ) -alkyl,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8- Heterocyclyl, wobei die 21 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl Heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl NR 8 heteroaryl or (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl, where the 21 latter radicals are in each case represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci - C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl are substituted, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (Cs-CeJ-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl,R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (Cs-CeJ-cycloalkylene alkyl, (C 3 - C 6) Cycloalkenyl, (C 1 -C 6) -alkyl-O- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkyl,
Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl-NR 3 -heteroaryl or (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are each represented by s radicals from the group consisting of cyano, halogen, nitro,
Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 ,
NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Al kinyl oder Phenyl, R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6. In all of the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
Erfindungsgemäße Verbindungen, in denen R1 für Halogen steht, können Compounds of the invention in which R 1 is halogen can
beispielsweise gemäß Schema 1 analog den in WO2013/083774 A1 genannten Methoden hergestellt werden. Hai bedeutet in Schema 1 Halogen. Aus diesen For example, according to Scheme 1 analogously to the methods mentioned in WO2013 / 083774 A1. Hai in Scheme 1 is halogen. From these
Verbindungen können durch Halogenaustausch weitere dem erfindungsgemäße Verbindungen hergestellt werden, in denen R1 andere Bedeutungen als Halogen hat. Solche Methoden des Halogenaustauschs sind dem Fachmann bekannt. Compounds can be prepared by halogen exchange further compounds of the invention in which R 1 has meanings other than halogen. Such methods of halogen exchange are known to those skilled in the art.
Schema 1 Scheme 1
(Ii) (Iii)  (Ii) (iii)
(i) Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in (i) collections of compounds of the formula (I) and / or their salts, which can be synthesized after the abovementioned reactions, can also be found in
parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise be prepared in a parallelized manner, this manual, in part
automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die automated or completely automated way. It is possible, for example, the reaction procedure, the work-up or the
Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Automate cleaning of products or intermediates. Overall, this is understood as a procedure, as described for example by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley 1999, at pages 1 to 34.
Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso- Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, For the parallelized reaction procedure and workup, a number of commercially available devices can be used, for example Calypyso reaction blocks (Caylpso reaction blocks) from Barnstead International,
Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England oder Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England or
MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, MultiPROBE Automated Workstations from Perkin Elmar, Waltham,
Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. Massachusetts 02451, United States. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, among others, chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer-supported reagents/Scavanger-Harze unterstützt werden. In der The implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. In the
Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1 , Polymer-Supported Scavengers and Reagents for Solution- Phase Synthesis (Sigma-Aldrich). Technical literature describes a number of experimental protocols, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or one for the corresponding
Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Approach adapted synthesis bound to a synthetic resin. Solid phase-assisted synthesis methods are adequately described in the specialist literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. The use of solid phase assisted
Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. The preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries. The present invention also provides libraries containing at least two compounds of formula (I) and their salts.
Die erfindungsgemäßen Verbindungen weisen eine ausgezeichnete herbizide The compounds of the invention have an excellent herbicidal
Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Effectiveness against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat perennial
Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfasst. Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Compound (s) on the plants (e.g., weeds such as mono- or dicotyledons
Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im Einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Weeds or unwanted crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied. In this case, the compounds of the invention, for example in Vorsaat- (possibly also by Incorporation into the soil), pre-emergence or post-emergence procedures. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be named, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria und Sorghum. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishamedum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, 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, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola und Xanthium. Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium. If the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
vollkommen ab. Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizidecompletely off. When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated. Although the compounds of the invention are excellent herbicides
Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Have activity against monocotyledonous and dicotyledonous weeds, are crops economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea , in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Crops such as agricultural crops or ornamental plantings.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen, abhängig von ihrer jeweiligen chemischen Struktur und der ausgebrachten Aufwandmenge, In addition, the compounds of the invention, depending on their respective chemical structure and the applied application rate,
hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Des excellent growth regulatory properties in crops. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Of
Weiteren eignen sie sich auch zur generellen Steuerung und Hemmung von Furthermore, they are also suitable for the general control and inhibition of
unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special
Eigenschaften betreffen z.B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Properties relate eg to the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others Fatty acid composition of the crop known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemaßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Maniok, Tomate, Erbse und anderen Gemüsesorten. Ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Preferably, the compounds of the invention as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe for example, in classical breeding methods and the generation of mutants. Alternatively, new plants with altered properties can help
gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen genetic engineering methods are produced (see eg EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/1 1376, WO 92/14827,  genetic modification of crops for the purpose of modifying the starch synthesized in the plants (eg WO 92/1 1376, WO 92/14827,
WO 91/19806),  WO 91/19806),
- transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ transgenic crops which are resistant to certain herbicides of the
Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate  Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind,  (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit  transgenic crops, for example cotton, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die  Bacillus thuringiensis toxins (Bt toxins) to produce, which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259).  Make plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972).  Transgenic crop plants with modified fatty acid composition (WO 91/13972).
- gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder - genetically modified crops with new content or
Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte  Secondary materials z. B. new phytoalexins, which increased one
Krankheitsresistenz verursachen (EPA 309862, EPA0464461 ) gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398). Disease resistance cause (EPA 309862, EPA0464461) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).
Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming")  Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming")
- transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen - Transgenic crops characterized by higher yields or better quality
transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking") Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ).  transgenic crops characterized by a combination z. B. the o. G. Numerous molecular biological techniques with which new transgenic plants with altered properties can be produced are known in principle, see, for example, BI 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).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in For such genetic manipulations, nucleic acid molecules can be used in
Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA- Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines corresponding antisense RNA, a sense RNA to obtain a
Cosuppressionseffekt.es oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den Cosuppressionseffekt.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in to cause the cells an antisense effect. 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. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
Organellen der Pflanzenzellen stattfinden. Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Organelles of the plant cells take place. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available, the altered properties by
Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen  Overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences. Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Herbicides containing essential plant enzymes, e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte In the application of the active compounds according to the invention in transgenic cultures, in addition to the effects to be observed in other cultures Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen als Herbizide zur Bekämpfung von Schadpflanzen in transgenen The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
Kulturpflanzen. Crops.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, The compounds of the invention may be in the form of wettable powders,
emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. emulsifiable concentrates, sprayable solutions, dusts or granules are used in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and
Wasser-in-ÖI-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), Water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
ULV-Formulierungen, Mikrokapseln und Wachse. ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden These individual formulation types are known and will be known in principle
beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", for example, described in: Winnacker-Kuchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. 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.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are, for example
beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid described in Watkins, Handbook of Insecticides 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, "Grenzflächenaktive Chemistry, 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schonfeldt, "Surface Active
Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix. Suitable safeners are
beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-mexyl und Dichlormid. for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromide.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykol- ethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate,
2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem Emulsifiable concentrates are made by dissolving the active ingredient in one
organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie organic solvents such as butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
Polyoxyethylensorbitanfettsäureester. Polyoxyethylene.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
Formulierungstypen bereits aufgeführt sind, hergestellt werden. Formulation types already listed are produced.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. For the preparation of plate, fluid bed, extruder and spray granules, see e.g.
Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. Method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81 -96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101 -103. For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche  In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser Granulation aids, fillers, etc. are used. In the water
dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. dispersible granules, the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Antifreeze and solvents, fillers, carriers and dyes, defoamers,
Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel.  Evaporation inhibitors and pH and viscosity affecting agents.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare For use, the formulations present in commercially available form are optionally diluted in customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 1 ,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 750 g/ha. Die nachstehenden Beispiele erläutern die Erfindung. Solutions are usually no longer diluted with other inert substances before use. With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha. The following examples illustrate the invention.
A. Chemische Beispiele A. Chemical examples
1 . Synthese von 4-Hydroxy-5-methyl-2-(1 -methyl-3-(trifluormethyl)pyrid-2-on-6- yl)pyridazin-3-on (Tabellenbeispiel Nr. 1 -3)  1 . Synthesis of 4-hydroxy-5-methyl-2- (1-methyl-3- (trifluoromethyl) pyrid-2-one-6-yl) pyridazin-3-one (Table Example No. 1-3)
Eine Mischung aus 5 g (19 mmol) 3,4-Dibrom-2-hydroxy-2H-furan-5-on und 3.4 g (19 mmol) 2-Hydrazino-5-(trifluormethyl)pyridin werden 4h in 75 nl 4N HBr erhitzt. Nach Abkühlen wird mit Wasser verdünnt und die Kristalle abgesaugt. Es werden 5.5 g (73% Ausbeute) 4,5-Dibrom-2-(5-(trifluormethyl)pyridin-2-yl)pyridazin-3-on erhalten, die ohne weitere Reinigung in die nächste Stufe eingesetzt werden.  A mixture of 5 g (19 mmol) of 3,4-dibromo-2-hydroxy-2H-furan-5-one and 3.4 g (19 mmol) of 2-hydrazino-5- (trifluoromethyl) pyridine are stirred for 4 h in 75 μl of 4N HBr heated. After cooling, it is diluted with water and the crystals are filtered off with suction. There are obtained 5.5 g (73% yield) of 4,5-dibromo-2- (5- (trifluoromethyl) pyridin-2-yl) pyridazin-3-one, which are used without further purification in the next stage.
1H-NMR (DMSO-De): 9.08 (s,1 H), 8.53 (dq,1 H), 8.35 (s,1 H), 7.94 (d,1 H). 1 H-NMR (DMSO-De): 9.08 (s, 1H), 8.53 (dq, 1H), 8.35 (s, 1H), 7.94 (d, 1H).
5.5 g (13.8 mmol) 4,5-Dibrom-2-(5-(trifluormethyl)pyridin-2-yl)pyridazin-3-on in 80 ml Dioxan werden mit 2.8 ml (15.1 mmol) Natriummethanolatlösung (5.4M/Methanol) versetzt. Nach 2h bei Raumtemperatur wird mit Wasser Undwenig 2N Salzsäure versetzt und die erhaltenen Kristalle abgesaugt. Es werden 4.3 g (89% Ausbeute) 5- Brom-4-methoxy-2-(5-(trifluormethyl)pyridin-2-yl)pyridazin-3-on erhalten, die ohne weitere Reinigung in die nächste Stufe eingesetzt werden. 5.5 g (13.8 mmol) of 4,5-dibromo-2- (5- (trifluoromethyl) pyridin-2-yl) pyridazin-3-one in 80 ml of dioxane are mixed with 2.8 ml (15.1 mmol) of sodium methoxide solution (5.4M / methanol). added. After 2 h at room temperature, 2N hydrochloric acid is added sparingly with water and the resulting crystals are filtered off with suction. There are obtained 4.3 g (89% yield) of 5-bromo-4-methoxy-2- (5- (trifluoromethyl) pyridin-2-yl) pyridazin-3-one, which are used without further purification in the next stage.
1H-NMR (DMSO-De): 9.06 (s,1 H), 8.50 (dq,1 H), 8.28 (s,1 H), 7.92 (d,1 H), 4.18 (s,3H). 1 H-NMR (DMSO-De): 9.06 (s, 1H), 8.50 (dq, 1H), 8.28 (s, 1H), 7.92 (d, 1H), 4.18 (s, 3H).
Eine Mischung von 1 .75 g (5 mmol) 5-Brom-4-methoxy-2-(5-(trifluormethyl)pyridin-2- yl)pyridazin-3-on und 1 .65 g (17.5 mmol) H2O2-Harnstoff in 20 ml Dichlorethan werden bei >5°C mit 1 .93 ml (13.8 mmol) Trifluoressigsäureanhydrid versetzt und dann 2h bei Raumtemperatur gerührt. Anschließend wird mit Wasser und 1 M Natriumbisulfitlösung gewaschen, die organische Phase getrocknet und das Lösungsmittel im Vakuum entfernt. Der Rückstand 5-Brom-4-methoxy-2-(5-(trifluormethyl)pyridin-1 -oxid-2- yl)pyridazin-3-on wird ohne weitere Reinigung in die nächste Stufe eingesetzt. A mixture of 1.75 g (5 mmol) 5-bromo-4-methoxy-2- (5- (trifluoromethyl) pyridin-2-yl) pyridazin-3-one and 1.65 g (17.5 mmol) H2O2 urea in 20 ml of dichloroethane are added at> 5 ° C with 1.93 ml (13.8 mmol) of trifluoroacetic anhydride and then stirred for 2 h at room temperature. It is then washed with water and 1 M sodium bisulfite solution, the organic phase is dried and the solvent is removed in vacuo. The residue 5-bromo-4-methoxy-2- (5- (trifluoromethyl) pyridine-1-oxide-2- yl) pyridazin-3-one is used without further purification in the next stage.
1H-NMR (DMSO-De): 9.06 (s,1 H), 8.06 (d,1 H), 8.34 (s,1 H), 7.91 (dq,1 H), 4.17 (s,3H). 1H-NMR (DMSO-De): 9.06 (s, 1H), 8.06 (d, 1H), 8.34 (s, 1H), 7.91 (dq, 1H), 4.17 (s, 3H).
5-Brom-4-methoxy-2-(5-(trifluormethyl)pyridin-1 -oxid-2-yl)pyridazin-3-on (5 mmol, roh) in 15 ml DMF werden mit 7 ml (50 mmol) Trifluoressigsäureanhydrid versetzt und 3h bei 90°C gerührt. Die Mischung wird dann auf Eiswasser gegeben und mit Essigester extrahiert. Die organische Phase wird mehrmals mit Wasser und ges. Kochsalzlösung gewaschen, getrocknet und das Lösungsmittel im Vakuum entfernt. Der Rückstand 5- Brom-4-methoxy-2-(3-(trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on wird ohne weitere Reinigung in die nächste Stufe eingesetzt. 5-Bromo-4-methoxy-2- (5- (trifluoromethyl) pyridine-1-oxide-2-yl) pyridazin-3-one (5 mmol, crude) in 15 ml of DMF are treated with 7 ml (50 mmol) of trifluoroacetic anhydride added and stirred at 90 ° C for 3h. The mixture is then poured onto ice-water and extracted with ethyl acetate. The organic phase is washed several times with water and sat. Washed brine, dried and the solvent removed in vacuo. The residue 5-bromo-4-methoxy-2- (3- (trifluoromethyl) pyrid-2-on-6-yl) pyridazin-3-one is used without further purification in the next step.
1H-NMR (DMSO-De): 8.26 (s,1 H), 8.22 (d,1 H), 7.78 (brs,1 H), 7.12 (d,1 H), 4.16 (s,3H). 1 H-NMR (DMSO-De): 8.26 (s, 1H), 8.22 (d, 1H), 7.78 (brs, 1H), 7.12 (d, 1H), 4.16 (s, 3H).
5-Brom-4-methoxy-2-(3-(trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on (5 mmol, roh) und5-Bromo-4-methoxy-2- (3- (trifluoromethyl) pyrid-2-on-6-yl) pyridazin-3-one (5 mmol, crude) and
1 ,38 g (10 mmol) Kaliumcarbonat in 20 ml DMF werden bei <5°C mit 1 .26 g (10 mmol) Dimethylsulfat versetzt. Man lässt auf Raumtemperatur kommen und versetzt nach 6 h die Mischung mit Wasser und Essigester. Die organische Phase wird mehrmals mit 2N1, 38 g (10 mmol) of potassium carbonate in 20 ml of DMF are added at <5 ° C with 1 .26 g (10 mmol) of dimethyl sulfate. It is allowed to come to room temperature and after 6 hours the mixture is mixed with water and ethyl acetate. The organic phase is repeated with 2N
Salzsäure, dann mit ges. Natriumhydrogencarbonat-Lösung und mit Kochsalzlösung gewaschen. Nach Trocknen und Einengen wird der Rückstand Hydrochloric acid, then with sat. Sodium bicarbonate solution and washed with saline. After drying and concentration, the residue
säulenchromatographisch mit Heptan/Essigester gereinigt. purified by column chromatography with heptane / ethyl acetate.
Fraktion A 0.40 g (21 % Ausbeute) 5-Brom-4-methoxy-2-(2-methoxy-3-Fraction A 0.40 g (21% yield) 5-bromo-4-methoxy-2- (2-methoxy-3-)
(trifluormethyl)pyridin-6-yl)pyridazin-3-on (Trifluoromethyl) pyridin-6-yl) pyridazin-3-one
1 H-NMR (DMSO-De): 8.36 (d,1 H), 8.27 (s,1 H), 7.43 (d,1 H), 4.17 (s,3H), 3.98 (s,3H). Fraktion B 1 .1 g (58% Ausbeute) 5-Brom-4-methoxy-2-(1 -methyl-3- (trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on  1 H-NMR (DMSO-De): 8.36 (d, 1H), 8.27 (s, 1H), 7.43 (d, 1H), 4.17 (s, 3H), 3.98 (s, 3H). Fraction B 1 .1 g (58% yield) 5-bromo-4-methoxy-2- (1-methyl-3- (trifluoromethyl) pyrid-2-on-6-yl) pyridazin-3-one
1H-NMR (DMSO-De): 8.35 (s,1 H), 8.15 (d,1 H), 6.66 (d,1 H), 4.20 (s,3H), 3.28 (s,3H). 1H-NMR (DMSO-De): 8.35 (s, 1H), 8.15 (d, 1H), 6.66 (d, 1H), 4.20 (s, 3H), 3.28 (s, 3H).
Zu 9 ml (6.3 mmol) ZnCI2-Lösung (0.7M/THF) werden unter Argon bei <5°C 1 .8 ml (5.4 mmol) Methylmagnesiumchlorid-Lösung (3M/THF) zugegeben. Anschließend wird 15 min. bei Raumtemperatur gerührt, wieder abgekühlt und 100 mg PdC dppf To 9 ml (6.3 mmol) ZnCl 2 solution (0.7M / THF) are added under argon at <5 ° C 1 .8 ml (5.4 mmol) of methyl magnesium chloride solution (3M / THF). Subsequently, 15 min. stirred at room temperature, cooled again and 100 mg PdC dppf
zugegeben. Zu dieser Mischung gibt man eine Suspension von 1 .03 g (2.7 mmol) 5- Brom-4-methoxy-2-(1 -methyl-3-(trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on in THF und erhitzt 2 h unter Rückfluss. Nach Abkühlen versetzt man mit 2N Salzsäure, verdünnt mit Essigester, trennt die Phasen und wäscht die organische Phase mit 2N Salzsäure, dann mit ges. Natriumhydrogencarbonat- und Kochsalzlösung. Nach Trocknen und Einengen wird der Rückstand säulenchromatographisch mit Heptan/Essigester gereinigt. Ausbeute 520 mg (61 %) an 4-Methoxy-5-methyl-2-(1 - methyl-3-(trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on. added. To this mixture is added a suspension of 1 .03 g (2.7 mmol) of 5-bromo-4-methoxy-2- (1-methyl-3- (trifluoromethyl) pyrid-2-one-6-yl) pyridazine-3- on in THF and heated for 2 h under reflux. After cooling, it is mixed with 2N hydrochloric acid, diluted with ethyl acetate, the phases are separated and the organic phase is washed with 2N hydrochloric acid, then with sat. Sodium bicarbonate and saline. To Drying and concentration, the residue is purified by column chromatography with heptane / ethyl acetate. Yield 520 mg (61%) of 4-methoxy-5-methyl-2- (1-methyl-3- (trifluoromethyl) pyrid-2-one-6-yl) pyridazin-3-one.
1 H-NMR (DMSO-De): 8.13 (d,1 H), 8.07 (s,1 H), 6.62 (d,1 H), 4.06 (s,3H), 3.23 (s,3H), 2.14 (s,3H).  1 H-NMR (DMSO-De): 8.13 (d, 1H), 8.07 (s, 1H), 6.62 (d, 1H), 4.06 (s, 3H), 3.23 (s, 3H), 2.14 ( s, 3H).
490 mg (1 .55 mmol) 4-Methoxy-5-methyl-2-(1 -methyl-3-(trifluormethyl)pyrid-2-on-6- yl)pyridazin-3-on in 3 ml Morpholin werden 1 h bei 100°C erhitzt. Anschließend wird eingeengt, der Rückstand mit Essigester aufgenommen und die Mischung mehrmals mit 2N Salzsäure und ges. Kochsalzlösung gewaschen. Nach Trocknen und Einengen erhält man die gewünschte Verbindung 4-Hydroxy-5-methyl-2-(1 -methyl-3- (trifluormethyl)pyrid-2-on-6-yl)pyridazin-3-on. Ausbeute 460 mg (98 %). 490 mg (1 .55 mmol) of 4-methoxy-5-methyl-2- (1-methyl-3- (trifluoromethyl) pyrid-2-one-6-yl) -pyridazin-3-one in 3 ml of morpholine are added 1 h heated at 100 ° C. It is then concentrated, the residue taken up with ethyl acetate and the mixture several times with 2N hydrochloric acid and sat. Washed saline. After drying and concentration, the desired compound 4-hydroxy-5-methyl-2- (1-methyl-3- (trifluoromethyl) pyrid-2-on-6-yl) pyridazin-3-one is obtained. Yield 460 mg (98%).
Die in nachfolgender Tabelle aufgeführten Beispiele sind ganz besonders bevorzugt. The examples listed in the following table are very particularly preferred.
Die verwendeten Abkürzungen bedeuten: The abbreviations used mean:
Me = Methyl Et = Ethyl Ph = Phenyl cPr = cyclo-Propyl  Me = methyl Et = ethyl Ph = phenyl cPr = cyclopropyl
Tabelle 1 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 1: Compounds of the invention of the general formula (I) wherein Q is
Q1 steht, R2 und R3 jeweils für Wassserstoff stehen, und X1 CZ1, X2 CH und X3 CH bedeuten. Q 1 , R 2 and R 3 are each hydrogen, and X 1 is CZ 1 , X 2 is CH and X 3 is CH.
Nr. R1 Y Z1 Physikalische Daten No. R 1 YZ 1 Physical data
( H-NMR, DMSO-d6, 400 MHz) (H-NMR, DMSO-d 6 , 400 MHz)
1-1 Me Me H  1-1 Me Me H
1-2 Me Me Me  1-2 Me Me Me
1-3 Me Me CF3 11.33 (brs,1 H), 8.13 (d,1 H), 7.98 (s,1 H), 6.63 1-3 Me Me CF 3 11.33 (brs, 1H), 8.13 (d, 1H), 7.98 (s, 1H), 6.63
(d,1 H), 3.22 (s,3H), 2.09 (s,3H)  (d, 1H), 3.22 (s, 3H), 2.09 (s, 3H)
1-4 Me Me Ph  1-4 Me Me Ph
1-5 Me Me 4-FPh  1-5 Me Me 4-FPh
1-6 Me Me 4-CIPh 1-6 Me Me 4-CIPh
Formulierungsbeispiele formulation Examples
Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill. A wettable powder readily dispersible in water is obtained by adding 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. potassium lignosulfonate and 1 part by weight oleoylmethyltaurine sodium as wetting and dispersing agent and grinding in a pin mill.
Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew.-Teilen A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight
Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic
Mineralöl (Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer An emulsifiable concentrate is obtained from 15 parts by weight of a
Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator. Compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
Ein in Wasser dispergierbares Granulat wird erhalten indem man A water-dispersible granules are obtained by
75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 75 parts by weight of a compound of the formula (I) and / or salts thereof,
10 Gew.-Teile ligninsulfonsaures Calcium, 10 parts by weight of lignosulfonic acid calcium,
5 Gew.-Teile Natriumlaurylsulfat, 5 parts by weight of sodium lauryl sulfate,
3 Gew.-Teile Polyvinylalkohol und 3 parts by weight of polyvinyl alcohol and
7 Gew.-Teile Kaolin 7 parts by weight kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit.
Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man A water-dispersible granule is also obtained by
25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the formula (I) and / or salts thereof,
5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonate sodium
2 Gew.-Teile oleoylmethyltaurinsaures Natrium,  2 parts by weight oleoylmethyltaurine acid sodium,
1 Gew.-Teil Polyvinylalkohol,  1 part by weight of polyvinyl alcohol,
17 Gew.-Teile Calciumcarbonat und  17 parts by weight of calcium carbonate and
50 Gew.-Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. 50 parts by weight of water Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.
C. Biologische Beispiele C. Biological examples
1 . Herbizide Wirkung gegen Schadpflanzen im Vorauflauf  1 . Herbicidal action against weevils in pre-emergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Wood fiber pots laid in sandy loam soil and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Emulsion with a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil. After the treatment, the pots are placed in the greenhouse and under good
Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur der Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigt beispielsweise die Verbindung Nr. 1 -3 bei einer Aufwandmenge von 320 g/ha eine mindestens 80%-ige Wirkung gegen Echinochloa crus galli, Abutilon theophrasti, Setaria viridis, Matricaria inodora, Stellaria media, Viola tricolor, Amaranthus Maintained growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants). In this case, for example, the compound no. 1 -3 at an application rate of 320 g / ha at least 80% effect against Echinochloa crus galli, Abutilon theophrasti, Setaria viridis, Matricaria inodora, Stellaria media, Viola tricolor, Amaranthus
retroflexus und Veronica persica. 2. Herbizide Wirkung gegen Schadpflanzen im Nachauflauf retroflexus and veronica persica. 2. Herbicidal action against harmful plants in postemergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in  Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Wood fiber pots laid in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontroll pflanzen). Dabei zeigt beispielsweise die Verbindung Nr. 1 -3 bei einer Aufwandmenge von 80 g/ha eine mindestens 80%-ige Wirkung gegen Echinochloa crus galli, Seta a viridis, Matricaria inodora, Ipomoea purpurea, Stellaria media, Viola tricolor, Amaranthus retroflexus und Veronica persica. Emulsion sprayed with an amount of water equivalent of 600 to 800 l / ha with the addition of 0.2% wetting agent on the green plant parts. After about 3 weeks life of the test plants in the greenhouse under optimal Growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = as control plants). In this case, for example, the compound no. 1 -3 at an application rate of 80 g / ha at least 80% effect against Echinochloa crus galli, Seta a viridis, Matricaria inodora, Ipomoea purpurea, Stellaria media, Viola tricolor, Amaranthus retroflexus and Veronica persica.

Claims

Patentansprüche BCS13-1020 Claims BCS13-1020
1 . 2-Hetaryl-Pyridazinonderivate der Formel (I) oder deren Salze 1 . 2-hetaryl-pyridazinone derivatives of the formula (I) or salts thereof
worin wherein
Q bedeutet Q1 oder Q2, Q is Q 1 or Q 2 ,
Q1 Q2 Q 1 Q 2
R1 bedeutet Wasserstoff, Halogen, Cyano, Amino, (Ci-C6)-Alkyl, Halogen-(Ci-C6)- alkyl, (C2-C6)-Alkenyl, (C2-C6)-Cycloalkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkoxy-(Ci-C3)-alkyl, (Ci-C6)- Al koxy-(C2-C6)-al koxy, (Ci -C6)-Al koxy-(C2-C6)-al koxy-(Ci -C3)-al kyl , (Ci -C6)-Al kyl-S(O)n, Halogen-(Ci-C6)-alkyl-S(O)n, (Ci-C6)-Alkyl-S(O)n-(Ci-C3)-alkyl, Halogen-(Ci-C6)-alkyl- S(O)n-(Ci-C3)-alkyl, (Ci-C6)-Alkylamino oder (Ci-CeJ-Dialkylamino, R 1 denotes hydrogen, halogen, cyano, amino, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkyl, C 6 ) alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- Ci-C 3) alkyl, (Ci-C 6) - Al alkoxy- (C 2 -C 6) -al koxy, (Ci-C6) alkoxy- -Al (C 2 -C 6) alkoxy- -al (Ci -C 3) -alkyl, (Ci-C6) -alkyl-S (O) n, halo (Ci-C6) alkyl-S (O) n, (Ci-C6) alkyl -S (O) n - (C 1 -C 3 ) -alkyl, halo (C 1 -C 6 ) -alkyl, -S (O) n - (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -alkylamino or (Ci-CeJ-dialkylamino,
R2 bedeutet Wasserstoff, Halogen, Cyano, Hydroxy, Nitro, Amino, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, (Ci-C6)-Alkyl-S(O)n, Halogen-(Ci-C6)-alkyl- S(O)n, (Ci-C6)-Alkyl-S(O)n-(Ci-C3)-alkyl, Halogen-(Ci-C6)-alkyl-S(O)n-(Ci-C3)-alkyl, (Ci- C6)-Alkylamino oder (Ci-C6)-Dialkylamino, R3 bedeutet Wasserstoff, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Alkoxycarbonyl, (Ci-C6)- Alkyl-S(O)n, (Ci-C6)-Alkyl-S-carbonyl, Arylcarbonyl oder Aryl-S(O)n bedeutet, wobei die zwei letztgenannten Reste jeweils durch s Reste R4 substituiert sind, R4 bedeutet Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci-C )-Alkoxy, R 2 is hydrogen, halogen, cyano, hydroxyl, nitro, amino, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) - alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-Ce) alkoxy, (Ci-C 6) alkyl-S ( O) n , halogeno (C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S (O) n - (C 1 -C 3 ) -alkyl, halogenated C 6 ) -alkyl-S (O) n - (C 1 -C 3 ) -alkyl, (C 1 -C 6) -alkylamino or (C 1 -C 6) -dialkylamino, R 3 is hydrogen, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 1 -C 6 ) -alkyl-S (O) n , (C 1 -C 6 ) -alkyl-S-carbonyl, Arylcarbonyl or aryl-S (O) n , where the latter two radicals are each substituted by s radicals R 4 , R 4 is halogen, (Ci-C) alkyl, halogeno (Ci-C) alkyl or (Ci -C) -alkoxy,
X1 bedeutet N oder CZ1, X 1 is N or CZ 1 ,
X2 bedeutet N oder CW, X 2 is N or CW,
X3 bedeutet N oder CR5, X 3 is N or CR 5 ,
X4 bedeutet N oder CY2, Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)- Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (C1-C6)- Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)- alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, X 4 is N or CY 2, Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl - (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -Alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2, (Ci-C 6) -alkyl-CN, (Ci-C 6) alkyl-SO 2 N (R 6) 2, (Ci-C 6) - alkyl-NR 6 COR 6, (Ci-C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -Alkyl-heterocyclyl, where the three latter radicals are in each case by s radicals from the group consisting of halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (Ci-C 6 ) alkyl, (Ci-Ce) alkoxy, halogen (Ci-Ce) - alkoxy substitui and wherein heterocyclyl carries n oxo groups,
Y2 bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, CO(NOR1)R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (Ci-C6)-Alkyl- S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)- Alkyl-CO2R1, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (C1- C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)- Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die sechs Y 2 is hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C3-C6) cycloalkyl , (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , CO (NOR 1 ) R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 (C 1 -C 6 ) -alkyl-S (O) n R 2, (Ci-C 6) alkyl-OR 1, (Ci-C 6) alkyl-OCOR 1, (Ci-C 6) alkyl-OSO2R 2, (Ci-C 6) - alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-CN, (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P (O) (OR 5 ) 2 , CH 2 P (O) (OR 5 ) 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) - alkyl heterocyclyl, phenyl, heteroaryl or heterocyclyl, wherein the six
letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl und the last-mentioned radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl and
Cyanomethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Substituted cyanomethyl, and wherein heterocyclyl carries n oxo groups,
Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Ci-C6)-alkyl-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, Z 1 represents hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Ci-C6 ) -alkyl- (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 ,
OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)- Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 1 , (Ci-C 6) - alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) -alkyl-SO 2 OR 6, (Ci-C 6) alkyl -CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each represented by s radicals selected from the group consisting of halogen, nitro, cyano, ( Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) - Alkoxy and halogeno (Ci-C6) -alkoxy are substituted, and whereby Heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
Z2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (Ci-C6)-alkyl-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen- (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, halo (C 2 -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (Ci-C6) -alkyl- (C3-C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, OR 6 , OCOOR 6 , NR 6 COOR 6 ,
C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (Ci-C 6) -alkyl-OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals mentioned are each represented by s radicals selected from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - ( C 1 -C 6 -alkyl, (C 1 -C 6 ) - Alkoxy and halo (C 1 -C 6) alkoxy, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
W bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-Alkoxy oder (Ci-C4)-Haloalkoxy, oder W is hydrogen, halogen, cyano, nitro, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C 6) -alkynyl, (C2-C6) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -haloalkoxy, or
Z1 oder Z2 und W bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z 1 or Z 2 and W together with the two carbon atoms to which they are attached form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Cs-CeJ-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C6)-alkyl substituiert ist, Carbon atoms and p heteroatoms from the group consisting of N, O and S, where this ring is represented by q radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) - alkyl, (Cs-CeJ-cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy) (C 1 -C 6) -alkyl is substituted,
R5 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci- C )-Alkoxy, R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (Cs-CeJ-Cycloalkyl, (C3- C6)-Cycloalkenyl, (Cs-CeJ-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (Cs-Ce)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8-R 5 is hydrogen, halogen, (C 1 -C 4) -alkyl, halogeno (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxy, R 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkyl C 6) haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) -alkynyl, (C2-C6) haloalkynyl, (Cs-CeJ-cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, (Cs-CeJ-halocycloalkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (Cs-Ce) -cycloalkyl- (C 1 -C 6 ) - alkyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl-heteroaryl, heterocycl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl- O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl-NR 8 -heteroaryl or (Ci-C 6) alkyl-NR 8 -
Heterocyclyl, wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Heterocyclyl, wherein the 21 latter radicals by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6) -alkyl heteroaryl, heterocyclyl, C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl-NR 3 -heteroaryl or ( C 6) -alkyl-NR 3 -heterocyclyl, wherein these 17 radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci-C) -alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder Phenyl, R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. R 9 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl or phenyl, R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4 , 5 or 6.
2. 2-Hetaryl-Pyridazinonderivate nach Anspruch 1 , worin 2. 2-hetaryl-Pyridazinonderivate according to claim 1, wherein
Q bedeutet Q1 oder Q2, Q is Q 1 or Q 2 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder (Ci-Ce)-Alkoxy- (Ci-C6)-alkyl, R 1 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) alkynyl, (C3-C6 ) -Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
R2 bedeutet Wasserstoff, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder(Ci-C6)-Alkyl-S(O)n, bedeutet Wasserstoff, R 2 denotes hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl or (C 1 -C 6 ) -alkynyl C 6 ) -alkyl-S (O) n , means hydrogen,
R4 bedeutet Halogen, (Ci-C )-Alkyl, Halogen-(Ci-C )-alkyl oder (Ci-C )-Alkoxy, X1 bedeutet N oder CZ1, X2 bedeutet N oder CW, X3 bedeutet N oder CH, R 4 is halogen, (C 1 -C 4 ) -alkyl, halogeno (C 1 -C 4 ) -alkyl or (C 1 -C 4) -alkoxy, X 1 is N or CZ 1 , X 2 is N or CW, X 3 is N or CH,
X4 bedeutet N oder CY2, X 4 is N or CY 2 ,
Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-Ce)- alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y2 bedeutet Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)- Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3- C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)- Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci- C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C3-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) alkyl SO 2 OR 6, (Ci-C 6) alkyl-CON (R 6) 2, (Ci-C 6 ) -Alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) ( OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the three last-mentioned radicals each consist of s radicals from the group from halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen- (Ci-C 6 ) -alkoxy are substituted, and wherein heterocyclyl n oxo groups t rägt, Y 2 is hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, halo (C 2 -C 6) alkenyl , (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl-, (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7, (Ci-C 6) - alkyl-S (O) n R 7, (Ci-C 6) -alkyl-OR 6, (Ci-C 6) alkyl-OCOR 6, (Ci-C 6) Alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl
SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci- C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the last three radicals are each represented by s radicals from the group consisting of halogen, Cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6) -alkoxy, and wherein heterocyclyl carries n oxo groups,
Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (C1- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z 1 represents hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) - alkenyl, (C2-C6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ-CycloalkyKCi- Ce) -alkyl, halogen- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , ( Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals each consist of s radicals the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen- ( Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (Ci-C 6) - alkyl, (Ci-Ce) alkoxy and halo (Ci-C6) alkoxy substituted are, and where
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
Z2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)- Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (C1- C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Z 2 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C 6) alkynyl, halo (C2-C6) -alkynyl, (C3-C6) cycloalkyl, halo (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C ( O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2, NR 6 SO 2 R 7, NR 6 COR 6, (Ci-C 6) - alkyl-S (O) n R 7, (Ci-C 6) -alkyl-OR 6, (Ci-C 6) - Alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -Alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (Ci-C6) - Alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6 ) -alkoxy, and where heterocyclyl carries n oxo groups,
W bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8- Heterocyclyl, wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n W is hydrogen, halogen, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C 2 -C 6) - alkenyl, (C2-C6) -alkynyl, (C3-C6) -cycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C ) -haloalkoxy, R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl-NR 8 heteroaryl or (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl, where the 21 last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci- C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl- (C 1 -C 4 -alkyl) 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -Alkyl-O-heterocyclyl, (C 1 -C 6) -alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are selected from s consisting of cyano, halogen, nitro , Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Al kinyl oder Phenyl, R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, R 9 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl or phenyl, R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2,
P bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. P is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6.
3. 2-Hetaryl-Pyridazinonderivate nach Anspruch 1 oder 2, worin 3. 2-hetaryl-Pyridazinonderivate according to claim 1 or 2, wherein
Q bedeutet Q1, R1 bedeutet Wasserstoff, (Ci-C )-Alkyl, (C2-C )-Alkenyl, Propargyl, Cyclopropyl oder S(O)nCH3, Q is Q 1 , R 1 is hydrogen, (C 1 -C 4) -alkyl, (C 2 -C 6) -alkenyl, propargyl, cyclopropyl or S (O) n CH 3 ,
R2 bedeutet Wasserstoff, R3 bedeutet Wasserstoff, R 2 is hydrogen, R 3 is hydrogen,
X1 bedeutet N oder CZ1, X 1 is N or CZ 1 ,
X2 bedeutet N oder CW, X 2 is N or CW,
X3 bedeutet N oder CH, X 3 is N or CH,
Y1 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, OR6, S(O)nR7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, (Ci-C6)-Alkyl-Heteroaryl oder (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y 1 represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, OR 6, S (O) n R 7, (Ci-C 6) -Alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , (C 1 -C 6 ) -alkyl heteroaryl or (Ci C6) -alkyl heterocyclyl, where the latter two radicals are each represented by s radicals from the group consisting of halogen, (Ci-C6) alkyl, halogeno (Ci-C6) alkyl, S (O) n - (Ci -C 6) -alkyl, (C 1 -C 6) -alkoxy and halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups,
Z1 bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die 3 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z 1 represents hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ -CycloalkyKCi-Ce) - alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 6, COOR 6, -OCOOR 6, NR 6 COOR 6, C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (Ci-C 6) -alkyl-OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the 3 last-mentioned radicals are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) - Cycloalkyl, S (O) n - (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy and halo (C 1 -C 6) alkoxy, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
W bedeutet Wasserstoff, Halogen, (Ci-C4)-Alkyl, W is hydrogen, halogen, (C 1 -C 4 ) -alkyl,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl oder (Ci-C6)-Alkyl-NR8- Heterocyclyl, wobei die 21 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci- C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-C 6) alkyl heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) -Alkyl-NR 8 -Heteroaryl or (Ci-C 6 ) -alkyl-NR 8 - heterocyclyl, wherein the 21 latter radicals in each case by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O ) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl, and wherein heterocyclyl n
Oxogruppen trägt, R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Oxo groups carrying, R 7 represents (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal kyl, ( C 3 -C 6 -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl- C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -Alkyl-O-heterocyclyl, (C 1 -C 6) -alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are each represented by s radicals from the group consisting of cyano, halogen , Nitro,
Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 ,
NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups, R 8 is hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder Phenyl, R 9 is (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C 2 -C 6) alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. A herbicidal composition, characterized by a herbicidally active content of at least one compound of the formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. A herbicidal composition according to claim 4 in admixture with formulation auxiliaries.
6. Herbizide Mittel gemäß Anspruch 4 oder 5 enthaltend mindestens einen weiteren pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 6. A herbicidal composition according to claim 4 or 5 containing at least one further pesticidal active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
7. Herbizide Mittel gemäß Anspruch 6 enthaltend einen Safener. 7. A herbicidal composition according to claim 6 containing a safener.
8. Herbizide Mittel gemäß Anspruch 7 enthaltend cyprosulfamid, cloquintocet- mexyl, mefenpyr-diethyl oder isoxadifen-ethyl. 8. A herbicidal composition according to claim 7 containing cyprosulfamide, cloquintocet- mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
9. Herbizide Mittel gemäß einem der Ansprüche 6 bis 8 enthaltend ein weiteres Herbizid. 9. A herbicidal composition according to any one of claims 6 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels gemäß einem der 10. A method for controlling undesirable plants, characterized in that an effective amount of at least one compound of formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to one of
Ansprüche 4 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Claims 4 to 9 on the plants or on the location of the undesirable
Pflanzenwachstums appliziert. Plant growth applied.
1 1 . Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln gemäß einem der Ansprüche 4 bis 9 zur Bekämpfung unerwünschter Pflanzen. 1 1. Use of compounds of the formula (I) according to one of Claims 1 to 3 or of herbicidal agents according to one of Claims 4 to 9 for controlling unwanted plants.
12. Verwendung gemäß Anspruch 1 1 , dadurch gekennzeichnet, daß die 12. Use according to claim 1 1, characterized in that the
Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. Compounds of formula (I) for controlling undesirable plants in crops of crops are used.
13. Verwendung gemäß Anspruch 12, dadurch gekennzeichnet, daß die 13. Use according to claim 12, characterized in that the
Nutzpflanzen transgene Nutzpflanzen sind. Crop plants are transgenic crops.
EP14796087.6A 2013-11-15 2014-11-10 2-hetaryl-pyridazinone derivatives and their use as herbicides Withdrawn EP3068772A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14796087.6A EP3068772A1 (en) 2013-11-15 2014-11-10 2-hetaryl-pyridazinone derivatives and their use as herbicides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13193109 2013-11-15
PCT/EP2014/074130 WO2015071206A1 (en) 2013-11-15 2014-11-10 2-hetaryl-pyridazinone derivatives and their use as herbicides
EP14796087.6A EP3068772A1 (en) 2013-11-15 2014-11-10 2-hetaryl-pyridazinone derivatives and their use as herbicides

Publications (1)

Publication Number Publication Date
EP3068772A1 true EP3068772A1 (en) 2016-09-21

Family

ID=49582662

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14796087.6A Withdrawn EP3068772A1 (en) 2013-11-15 2014-11-10 2-hetaryl-pyridazinone derivatives and their use as herbicides

Country Status (5)

Country Link
US (1) US20160326135A1 (en)
EP (1) EP3068772A1 (en)
JP (1) JP2016538284A (en)
CN (1) CN105899499A (en)
WO (1) WO2015071206A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201117019D0 (en) * 2011-10-04 2011-11-16 Syngenta Ltd Herbicidal compounds
CN105745199A (en) * 2013-11-12 2016-07-06 拜耳作物科学股份公司 Pyridazinone derivatives and their use as herbicides
US20220312767A1 (en) * 2019-09-25 2022-10-06 Nippon Soda Co., Ltd. Pyridazine compounds and herbicides
WO2023166067A1 (en) 2022-03-02 2023-09-07 Syngenta Crop Protection Ag Microbiocidal pyridazinone amide derivatives
WO2024132895A1 (en) 2022-12-19 2024-06-27 Syngenta Crop Protection Ag Microbiocidal dihydrooxadiazinyl pyridazinone compounds

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3202678A1 (en) * 1982-01-28 1983-08-04 Basf Ag, 6700 Ludwigshafen SUBSTITUTED 4,5-DIMETHOXY-PYRIDAZONE, METHOD FOR THE PRODUCTION THEREOF, THE HERBICIDES CONTAINING IT AND THEIR USE AS HERBICIDES
WO1984002919A1 (en) 1983-01-17 1984-08-02 Monsanto Co Plasmids for transforming plant cells
BR8404834A (en) 1983-09-26 1985-08-13 Agrigenetics Res Ass METHOD TO GENETICALLY MODIFY A PLANT CELL
BR8600161A (en) 1985-01-18 1986-09-23 Plant Genetic Systems Nv CHEMICAL GENE, HYBRID, INTERMEDIATE PLASMIDIO VECTORS, PROCESS TO CONTROL INSECTS IN AGRICULTURE OR HORTICULTURE, INSECTICIDE COMPOSITION, PROCESS TO TRANSFORM PLANT CELLS TO EXPRESS A PLANTINIDE TOXIN, PRODUCED BY CULTURES, UNITED BY BACILLA
ATE80182T1 (en) 1985-10-25 1992-09-15 Monsanto Co PLANT VECTORS.
ES2018274T5 (en) 1986-03-11 1996-12-16 Plant Genetic Systems Nv VEGETABLE CELLS RESISTANT TO GLUTAMINE SYNTHETASE INHIBITORS, PREPARED BY GENETIC ENGINEERING.
IL83348A (en) 1986-08-26 1995-12-08 Du Pont Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
DE3733017A1 (en) 1987-09-30 1989-04-13 Bayer Ag Stilbene synthase gene
DE3807896A1 (en) * 1988-03-10 1989-09-21 Basf Ag 2-PHENYLPYRIDAZINE-3-ON COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
EP0472722B1 (en) 1990-03-16 2003-05-21 Calgene LLC Dnas encoding plant desaturases and their uses
JP3325022B2 (en) 1990-06-18 2002-09-17 モンサント カンパニー Increased starch content in plants
WO1992000377A1 (en) 1990-06-25 1992-01-09 Monsanto Company Glyphosate tolerant plants
DE4107396A1 (en) 1990-06-29 1992-01-02 Bayer Ag STYLE SYNTHASE GENES FROM VINEYARD
SE467358B (en) 1990-12-21 1992-07-06 Amylogene Hb GENETIC CHANGE OF POTATISE BEFORE EDUCATION OF AMYLOPECT TYPE STARCH
DE4104782B4 (en) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Novel plasmids containing DNA sequences that cause changes in carbohydrate concentration and carbohydrate composition in plants, as well as plants and plant cells containing these plasmids
GB201121317D0 (en) 2011-12-09 2012-01-25 Syngenta Ltd Herbicidal compounds
CN105745199A (en) * 2013-11-12 2016-07-06 拜耳作物科学股份公司 Pyridazinone derivatives and their use as herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2015071206A1 *

Also Published As

Publication number Publication date
WO2015071206A1 (en) 2015-05-21
JP2016538284A (en) 2016-12-08
CN105899499A (en) 2016-08-24
US20160326135A1 (en) 2016-11-10

Similar Documents

Publication Publication Date Title
WO2017055146A1 (en) Acylated n-(1,2,5-oxadiazole-3-yl)-, n-(1,3,4-oxadiazole-2-yl)-, n-(tetrazole-5-yl)- and n-(triazole-5-yl)-aryl carboxamides, and use thereof as herbicides
EP2844649A1 (en) N-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide salts and use thereof as herbicides
WO2017144402A1 (en) N-(5-halogen-1,3,4-oxadiazol-2-yl)aryl carboxylic acid amides and the use thereof as herbicides
EP2855437B1 (en) N-(tetrazol-5-yl)- and n-(triazol-5-yl)aryl carboxylic acid athioamides and use of same as herbicides
WO2016146561A1 (en) Salts of n-(1,3,4-oxadiazol-2-yl) aryl carboxylic acid amides and the use of same as herbicides
EP3416961A1 (en) Quinazolinedione-6-carbonyl derivatives and their use as herbicides
WO2014053473A1 (en) 1,2,4-triazine-3,5-dione-6-carboxamides and use thereof as herbicide
WO2014086746A1 (en) N-(isoxazol-3-yl)-aryl-carboxylic acid amides and use thereof as herbicides
EP3317272A1 (en) N-(1,3,4-oxadiazol-2-yl)aryl carboxamide derivatives with herbicidal action
EP2928887A1 (en) N-(oxazol-2-yl)-aryl-carboxylic acid amides and use thereof as herbicides
EP3145917A1 (en) 5-(hetero)aryl-pyridazinones and their use as herbicides
EP3068773B1 (en) Pyridazinone derivatives and their use as herbicides
EP2844650B1 (en) 6-pyridon-2-carbamoyl-azoles and their application as herbicides
WO2017005567A1 (en) N-(tetrazole-5-yl)- and n-(triazole-5-yl)aryl carboxamide derivatives with herbicidal action
EP3068772A1 (en) 2-hetaryl-pyridazinone derivatives and their use as herbicides
WO2014086737A1 (en) Condensed 2-pyridone-3-carboxamides and the use thereof as herbicides
EP3174871B1 (en) Bicyclic aryl carboxilic acid amides and their use as herbicides
WO2015007632A1 (en) Uracil-5-carboxamides and their use as herbicides
WO2015007662A1 (en) Azin-2-one-3-carboxamides and their use as herbicides
WO2015007633A1 (en) 6-azinone-2-carbonyl derivatives and their use as herbicides
EP3393244A1 (en) 2-amino-5-ketoxime-pyrimidine derivatives and their use for controlling undesired plant growth
EP2882732B1 (en) Herbicidally active derivatives of 6&#39;-phenyl-2,2&#39;-bipyridin-3-carboxylic acid
WO2014023669A1 (en) Herbicidally active 2&#39;-phenyl-2,4&#39;-bipyridine-3-carboxylic acid derivatives
EP2918581A1 (en) 2-(Azinedionyl)-pyridazinone derivatives and their use as herbicides
WO2014086738A1 (en) Herbicidally active 4-amino-6-acyloxymethyl pyrimidine and 4-amino-2-acyloxymethyl pyridine

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20160615

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20170112