EP1387831A1 - Substituted arylketones - Google Patents
Substituted arylketonesInfo
- Publication number
- EP1387831A1 EP1387831A1 EP02730220A EP02730220A EP1387831A1 EP 1387831 A1 EP1387831 A1 EP 1387831A1 EP 02730220 A EP02730220 A EP 02730220A EP 02730220 A EP02730220 A EP 02730220A EP 1387831 A1 EP1387831 A1 EP 1387831A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- cyano
- chlorine
- fluorine
- optionally
- methyl
- 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- Withdrawn
Links
- 238000000034 method Methods 0.000 claims abstract description 49
- 239000004009 herbicide Substances 0.000 claims abstract description 9
- -1 amino, cyanoamino, nitroamino, hydroxyamino, hydrazino Chemical group 0.000 claims description 744
- 239000000460 chlorine Substances 0.000 claims description 172
- 229910052801 chlorine Inorganic materials 0.000 claims description 172
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 167
- 239000001257 hydrogen Substances 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 105
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 99
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 95
- 229910052736 halogen Inorganic materials 0.000 claims description 93
- 150000002431 hydrogen Chemical class 0.000 claims description 93
- 150000002367 halogens Chemical class 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 76
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 76
- 229910052794 bromium Inorganic materials 0.000 claims description 76
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 72
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 71
- 229910052731 fluorine Inorganic materials 0.000 claims description 69
- 239000011737 fluorine Substances 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 55
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
- 125000004414 alkyl thio group Chemical group 0.000 claims description 45
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 43
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 43
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 43
- 125000001153 fluoro group Chemical group F* 0.000 claims description 42
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 230000008569 process Effects 0.000 claims description 35
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 21
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 12
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 12
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 10
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 8
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000005981 pentynyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 5
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 4
- 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 4
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- RXVBJUZEFSAYPW-UHFFFAOYSA-N 1,3-diphenylpropane-1,2,3-trione Chemical class C=1C=CC=CC=1C(=O)C(=O)C(=O)C1=CC=CC=C1 RXVBJUZEFSAYPW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 2
- 238000010931 ester hydrolysis Methods 0.000 claims description 2
- BPQPBEVHMFRECG-UHFFFAOYSA-N fluoro formate Chemical compound FOC=O BPQPBEVHMFRECG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical group [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 2
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 125000006434 propyl cyclopropyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 78
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000007858 starting material Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 241000219146 Gossypium Species 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 7
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- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
Definitions
- the invention relates to new substituted aryl ketones, processes for their preparation and their use as plant treatment agents, in particular as herbicides.
- a 1 represents a single bond or O (oxygen), S (sulfur), SO or SO 2
- a 2 represents alkanediyl (alkylene), alkenediyl or alkindiyl,
- Q represents O (oxygen) or S (sulfur),
- R 1 for hydrogen or for optionally substituted alkyl, alkoxy,
- R 2 represents hydrogen, animo, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, dialkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, Alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino
- X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
- Y represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and represents one of the groupings below
- n the numbers 0 to 6
- R represents hydrogen, halogen or optionally substituted in each case
- R 4 for hydroxyl, formyloxy, halogen, or for optionally substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonate Arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl,
- R 5 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
- R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl
- R 7 represents hydroxy, formyloxy, or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
- R 8 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfmyl or alkylsulfonyl,
- R 9 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
- R 10 represents hydrogen or represents optionally substituted alkyl or cycloalkyl
- R 1 ' represents hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfmyl or alkylsulfonyl,
- the radical X is preferably at position (2) of the phenyl ring.
- hydrocarbon chains such as alkyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
- the compounds of the general formula (I) can exist in various stereoisomeric forms, the invention includes the stereoisomeric forms which are possible in each case.
- a 1 preferably represents O or a single bond.
- a 2 preferably represents alkanediyl (alkylene), alkenediyl or alkindiyl, each having up to 6 carbon atoms.
- Q is preferably O (oxygen).
- R 1 preferably represents hydrogen, in each case optionally by cyano
- C ⁇ -C 4 haloalkyl, C 1 -C 4 - ⁇ lkoxy or Ci-C 4 each having 6 or 10 carbon atoms group haloalkoxy substituted aryl or arylalkyl in the aryl and optionally 1 to 4 carbon atoms in the alkyl part, or represents the grouping - C (Q) -R 2 .
- X preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or in each case optionally by cyano, halogen, dQ-alkoxy, C r C 4 - alkylthio, C r C 4 - alkylsulfmyl or C r C 4 - Alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylammo or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.
- Y preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by cyano, halogen, dC 4 alkoxy, C r C 4 alkylthio, C r C 4 alkylsulfmyl or C r C 4 - Alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylammo or dialkylaminosulfonyl, each with 1 to 6
- Z preferably represents one of the groupings below
- m preferably represents the numbers 0 to 3.
- R 3 preferably represents hydrogen, halogen, in each case optionally by cyano, halogen, dC 4 -alkoxy, C 1 -C 4 -alkylthio, dC -alkylsulfinyl or
- R 4 preferably represents hydroxy, formyloxy, halogen, in each case optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, dC 4 - alkylthio, dC - alkylsulfmyl or dC 4 - alkylsulfonyl-substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, Alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, each for alkenyloxy optionally substituted by halogen or alkynyloxy each having 3 to 6 carbon atoms, each for optionally using nitro,
- R 5 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl,
- Halogen in each case optionally cyano-, halogen, C 4 - alkoxy, dC 4 - alkylthio, dC 4 -Alkylsulf ⁇ nyl or C 4 - substituted alkylsulfonyl, alkyl, alkoxy, alkylthio, Alkylsulfmyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or d-C4-alkyl.
- R 6 preferably represents hydrogen, represents optionally cyano-, halogen, C ⁇ -C 4 alkoxy, dC 4 alkylthio, C 1 -C 4 -Alkylsulfmyl or C 4 alkyl sulfonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case alkenyl or alkynyl optionally substituted by cyano or halogen in each case 3 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl each optionally substituted by cyano, halogen or dC 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen , dC 4 -alkyl, C 4 haloalkyl, dC 4 --
- R 7 preferably represents hydroxyl, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or dC 4 -alkoxy, for alkenyloxy optionally substituted by cyano or halogen or alkynyl oxy each having 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, C 4 alkyl, C 1 -C 4 haloalkyl, dC 4 - alkoxy, dC 4 -haloalkoxy, C 1 -C 4 -Alkylthio, C 1 -C 4 -Halogenalkylfhio, d- C -Alkylsulfinyl, dC 4 -Halogenalkyl
- haloalkylsulfonyl substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
- R 8 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups and optionally substituted by cyano, halogen or dC-alkoxy
- R 9 preferably represents hydrogen, alkyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or dC 4 alkyl.
- R 10 preferably represents hydrogen, alkyl which is optionally substituted by cyano, halogen or dC 4 -alkoxy, or cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl.
- R 1! preferably represents hydrogen, cyano, carbamoyl, halogen, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and is optionally substituted by cyano, halogen or dC-alkoxy.
- a 2 particularly preferably represents methylene (-CH 2 -), Efhan-l, l-diyl (-CH (CH 3 ) -) 5
- Propane-1,2-diyl (-CH (CH 3 ) CH 2 -), propane-1,3-diyl (-CH 2 CH 2 CH 2 -), butane-1,3-diyl (-CH (CH 3 ) CH 2 CH 2 -), butane-1,4-diyl (-CH 2 CH 2 CH 2 CH 2 -), ethylenediyl, propendiyl, butenediyl, ethindiyl, propindiyl or butindiyl.
- R 1 particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i -
- Chlorine methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio
- X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio
- Y particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio,
- n particularly preferably represents the numbers 0, 1 or 2.
- R particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio , or for phenyl, or - if m is 2 - optionally together with a second radical R 3 for oxygen, propane-l, 3-diyl or butane-1,4
- R 4 particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfonyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butoxycarbonyloxy, methoxy , Ethoxycarbonyloxy,
- R 5 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propyl-fhio, methylsulfinyl, ethylsulfinyl, methylsul
- R 6 particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each for propenyl optionally substituted by cyano, fluorine, chlorine or bromine, butenyl, propynyl or butinyl, for each optionally substituted by cyano, fluorine, Chloro, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloprop
- R particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. Butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-
- Bromine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.
- R 8 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or in each case optionally by cyano,
- R 9 particularly preferably represents hydrogen, in each case optionally by
- R 11 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , Methylsulfonyl or ethylsulfonyl.
- a 2 very particularly preferably represents methylene (-CH 2 -), ethane-1,2-diyl (dimethylene, -CH 2 CH 2 -) or propane-1,3-diyl (-CH 2 CH 2 CH 2 -).
- R 1 very particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methyl, n- or i-propyl, n- or i -Butyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or.i-propylfhio, methylamino, ethylamino, n- or i-propylamino, for dimethylamino, for each optionally by fluorine and / or chlorine substituted propenyl, butenyl, ethynyl,
- X very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfmylmethyl, methylsulfonylmethyl, methoxy , Ethoxy, difluoromethoxy,
- Y very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, methyl Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
- n very particularly preferably represents the numbers 0 or 1.
- R 3 very particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - for the
- R 3 for oxygen, propane-1, 3-diyl or butane-1,4-diyl.
- R 4 very particularly preferably stands for hydroxyl, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl- which is optionally substituted by fluorine and / or chlorine.
- sulfinyl ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxyoxy, n- or i-propylaminocarbonyloxyoxy, methyl- , n- or i-Propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine and / or chlorine, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl , Trifluoromethyl, meth
- R 5 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, in each case methyl optionally substituted by fluorine and or chlorine,
- R 6 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each in each case optionally propenyl, butenyl, propynyl or substituted by fluorine or chlorine
- R 7 very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- which are each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy.
- R 8 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy.
- Butyroyl methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
- R 9 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
- R 10 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl which is optionally substituted by fluorine, chlorine or methyl.
- R 11 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy.
- R 1 most preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, methoxy or ethoxy or the group -C (Q) -R 2 .
- R 2 most preferably represents hydrogen, amino, hydrazino, each methyl, ethyl or n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino, for each optionally by fluorine,
- Bromine methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylfhio, trifluoromethylthio, methoxycarbonyl or ethoxycarbonyl-substituted furyl, furylmethyl, pyrylmethyl, methylmethyl, methylethyl, methylyl.
- X most preferably represents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
- Y most preferably represents hydrogen, nitro, cyano, fluorine, chlorine,
- R most preferably represents hydrogen or methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
- R 4 most preferably represents hydroxy
- R 5 most preferably represents hydrogen, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine.
- R 6 most preferably represents hydrogen or methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.
- R 7 most preferably represents hydroxyl, in each case methoxy or ethoxy optionally substituted by fluorine or chlorine, or phenylmethoxy optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy.
- A. 1, A A 2, Q r, ⁇ R »l, ⁇ R.2, X, Y and Z each have the meanings given above as preferred or very particularly preferred.
- the new substituted aryl ketones of the formula (I) are notable for strong and selective herbicidal activity.
- a 1 , A 2 , R 1 , X, Y and Z have the meaning given above,
- Q and R 2 have the meaning given above and Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
- Q 2 for halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably for chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or
- A, A, R, X, Y and Z are preferably those meanings which have already been mentioned above in connection with the description of the compounds according to the invention of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for A 1 , A 2 , R 1 , X, Y and Z have been given.
- X 1 represents halogen (preferably fluorine, chlorine, bromine or iodine, in particular chlorine or bromine),
- R 1 has the meaning given above, if appropriate in the presence of a diluent, such as tetrahydrofuran, if appropriate under elevated pressure at temperatures between 0 ° C. and 100 ° C. (cf. the preparation examples).
- a diluent such as tetrahydrofuran
- the precursors of the general formula (VIII) are known and / or can be prepared by processes known per se (cf. WO-A-95/31446, WO-A-00/68227, production examples).
- the precursors of the general formula (IX) are known synthetic chemicals.
- Formula (III) provides a general definition of the (thi) oxo compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I).
- Q and R 3 preferably have those meanings which are preferred, particularly preferred, very particularly preferred or most preferred for Q already in connection with the description of the compounds of the general formula (I) according to the invention and R have been specified;
- Q preferably represents fluorine, chlorine, bromine, dC 4 -alkoxy, C 1 -C 4 -alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.
- the starting materials of the general formula QJ) are known organic synthetic chemicals.
- Formula (TV) provides a general definition of the carboxylic acids to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
- a 1 , A 2 , Q, R 1 , R 2 , X and Y preferably have those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention preferably, very particularly preferably or most preferably for A 1 , A 2 , Q, R 1 , R 2 , X and Y have been given.
- the starting materials of the general formula (IV) are not yet known from the literature; as new substances, they are also the subject of the present application.
- a 1 , A 2 , Q, X and Y have the meaning given above and
- R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably dC 4 -alkyl, in particular methyl or ethyl),
- R 2 has the meaning given above
- a diluent such as, for example, acetonitrile or ethanol
- a diluent such as, for example, acetonitrile or ethanol
- a 1 , A 2 , R 1 , X and Y have the meaning given above and
- R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably C 1 -C 4 -alkyl, in particular methyl or ethyl),
- Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio, - or, if appropriate, with corresponding iso (thio) cyanates -
- reaction aids e.g. Potassium carbonate or triethylamine
- diluents e.g. Acetonitrile or N, N-dimethyl-formamide
- Formula (V) provides a general definition of the compounds to be used further as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
- Z preferably has the meaning which has already been given above as preferred, particularly preferred, very particularly preferred or most preferred for Z in connection with the description of the compounds of the general formula (I) according to the invention.
- the starting materials of the general formula (V) are known organic synthetic chemicals.
- Formula (Ia) provides a general definition of the substituted benzoyl ketones to be used as starting materials in process (c) according to the invention for the preparation of compounds of the general formula (I).
- a 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably, particularly preferably, very particularly preferably or most preferably for A 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y have been given.
- the starting materials of the general formula (Ia) are also the subject of the present application as new substances; they can be produced by processes (a) or (b) according to the invention.
- Formula (VI) provides a general definition of the aryl ketones to be used as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I).
- a 1 , A 2 , Q, R 1 , X, Y and Z preferably have those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention , very particularly preferred or
- Q preferably represents fluorine, chlorine, bromine, dC 3 -alkoxy, dd-alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.
- the starting materials of the formula (VI) can be prepared by processes known to those skilled in the art.
- Formula (VII) provides a general definition of the compounds to be used further as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I).
- R 2 preferably has the meaning which has already been given above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for R 2 .
- the starting materials of the general formula (VII) are known organic compounds.
- Formula (X) provides a general definition of the iso (fhio) cyanates to be used as starting materials in the process () according to the invention for the preparation of compounds of the general formula (TV).
- a 1 , A 2 , Q, X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for A 1 , A 2 , Q, X and Y has been specified.
- the starting materials of the general formula (X) can be obtained by processes known to those skilled in the art.
- Formula (XI) provides a general definition of the amino compounds to be used as starting materials in process ( ⁇ ) according to the invention for the preparation of compounds of the general formula (IV).
- a 1 , A 2 , R 1 , X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most has preferably been given for A 1 , A 2 , R ⁇ X and Y.
- the starting materials of the general formula (XI) can be prepared by processes known to those skilled in the art.
- reaction auxiliaries for processes (a), (b), (c) and (d) according to the invention are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal, acetate, amide, carbonate, bicarbonate, hydride, hydroxide or alkanoate, such as sodium, potassium or calcium acetate, lithium, sodium, Potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium -hydroxide, sodium or potassium, -mefhanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyld
- 5-ethyl-2-methyl-pyridine 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl piperidine, N-methylmorpholine, N-ethylmorpholine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] - undec-7-ene (DBU).
- DABCO 1,4-diazabicyclo [2.2.2] octane
- DBN 1,5-diazabicyclo [4.3.0] non-5-ene
- DBU 1,8-diazabicyclo [5.4.0] - undec-7-ene
- Phase transfer catalysts are also suitable as further reaction aids for processes (a), (b), (c) and (d) according to the invention.
- Examples of such catalysts are:
- Tetrabutylammonium bromide tetrabutylammonium chloride, tetraoctylammonium chloride, tetiabutylammonium hydrogen sulfate, methyl trioctylammonium chloride,
- Process (b) according to the invention for the preparation of the new substituted aryl ketones of the general formula (I) is optionally carried out using a dehydrating agent.
- a dehydrating agent The usual chemicals suitable for binding water can be considered.
- Examples of these are dicyclohexylcarbodiimide, carbonyl-bis-imidazole and propanephosphonic anhydride.
- Dicyclohexylcarbodiimide and propanephosphonic anhydride may be mentioned as particularly suitable dehydrating agents.
- diluents carried out.
- Suitable diluents for carrying out processes (a), (b), (c) and (d) in addition to water are, in particular, inert organic solvents.
- these include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,
- reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c) and (d). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
- the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
- the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
- the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally agitated several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
- the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
- the active compounds according to the invention can e.g. can be used in the following plants:
- Scirpus, Setaria, Sorghum Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
- the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
- the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.
- the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
- the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
- plants and parts of plants can be treated.
- Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including natural cultivated plants).
- Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
- Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
- the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
- all plants and their parts can be treated according to the invention.
- wild plants weeds, harmful plants
- conventional organic breeding methods such as e.g. Crossing or protoplast f ⁇ sion, preserved plant species and plant varieties (crop plants) and their parts treated.
- transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organism) and their parts are treated.
- the term "parts” or "parts of plants” or "plant parts” was explained above.
- Plant varieties are cultivated plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
- transgenic plants or plant cultivars to be treated according to the invention include all plants which are genetically engineered
- Harvest products, higher shelf life and / or workability of the harvest products are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
- animal and microbial pests such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses
- transgenic plants are the important crops such as cereals (including rice), corn, soybeans, potatoes, cotton, beets, rapeseed, cultivated grasses such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and plantation crops as mentioned oil and rubber trees, with cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed being particularly highlighted.
- the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CrylLA, CrylllA, Cry ⁇ iB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
- the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
- SAR systemic acquired resistance
- Inhibitors such as Sethoxydim, as well as Bromoxynil.
- the genes imparting the desired properties can also occur in combinations with one another in the transgenic plants.
- Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g.
- herbicide-tolerant plants are maize varieties, cotton varieties, soy varieties, cereals including rice varieties, beet varieties and rapeseed varieties sold under the trade names Roundup Ready® (tolerance against
- Glyphosate e.g. Maize, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance to glufosinates, e.g. rapeseed, corn, beet), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. maize).
- the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize, rice).
- the treatment according to the invention can also cause superadditive (“synergistic") effects. For example, reduced application rates and / or extensions of the
- Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
- the active ingredients can be converted into the usual formulations, such as
- Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
- formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
- extenders that is to say liquid solvents and / or solid carriers
- surface-active agents that is to say emulsifiers and or dispersants and / or foam-generating agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- aromatics such as xylene, toluene, or alkylnaphthalenes
- chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
- Alcohols such as butanol or glycol, and their ethers and esters
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,
- Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds according to the invention can also be used for combating weeds, as a mixture with known herbicides and / or with substances which improve crop plant tolerance ("safeners"), ready formulations or tank mixes being possible Mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
- safeners substances which improve crop plant tolerance
- herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benlububuluron, bezububuluron (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromacil, bromobutide, bromofenoxime, bromoxynil, butachlor , Butafenacil (-allyl), Butenachlor, Butralin, Butroxyd
- Dikegulac (-sodium), dimefuron, dimepiperate, dimethachlor, dimethametryn, di- methenamide (-P), dimexyflam, dinitramine, diphenamide, diquat (-dibromide), di-thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, efhametsulfuron (-methyl), efhiozin, ethofumesulfate, efhoxoxy Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-M-isopropyl, -M-methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flu-chloralin , Flufenacet, Flumetsulam, Flumiclor
- MCPA Mecoprop (-P), Mefenacet, Mesotrione, Metamitron, Metazachlor, Metha benzthiazuron, Methyldymron, Metobenzuron, Metobromuron, (S-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Mononate, Moninate, Molinate, Molinate, Napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamide, phenmedi-phamophosphonosulfonyl, prima- lulfon, prinulfil (proline), picolinmethyl (
- Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulf- uron, tribenuron (-methyl), triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron (-methyl), tritosulfuron.
- Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-
- a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
- Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
- the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
- the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
- the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive ones
- the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
- the oily residue is dissolved in 200 ml of acetonitrile, 17 g (168 mmol) of triethylamine and 3.26 g (38 mmol) of 2-hydroxy-2-methyl-propionitrile are added, and the mixture is stirred at room temperature for a further 20 hours.
- the solvent is then largely removed under reduced pressure and the oily residue is taken up in 100 ml of dichloromethane.
- the organic phase is washed with 2N hydrochloric acid and with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The filtrate is freed from the solvent under reduced pressure.
- Ammonia is heated to 90 ° C in an autoclave for 6.5 hours. The excess ammonia is largely evaporated, the product which separates is separated off by filtration and dried under reduced pressure.
- Example (IV-1) for example the compounds of the general formula (TVa) listed in Table 4 below can also be prepared.
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
- Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
- the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
- the concentration of the spray liquor is chosen so that in
- the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
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Abstract
The invention relates to novel arylketones of formula (I) wherein A<1>, A<2>, Q, R<1>, R<2>, X, Y and Z have the meaning cited in the description, the use thereof as herbicides and to methods and intermediate products for the production thereof.
Description
Substituierte ArylketoneSubstituted aryl ketones
Die Erfindung betrifft neue substituierte Arylketone, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel, insbesondere als Herbizide.The invention relates to new substituted aryl ketones, processes for their preparation and their use as plant treatment agents, in particular as herbicides.
Es ist bereits bekannt, dass bestimmte substituierte Arylketone herbizide Eigenschaften aufweisen (vgl. EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A- 186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175, EP-A- 487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797, EP-A-It is already known that certain substituted aryl ketones have herbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175, EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP -A-609 797, EP-A-
609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, US-A-5 804 532, US-A- 5 834402, US-A-5 846 906, US-A-5 863 865, WO-A-95/31466, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200, WO-A-96/26206, WO-A-97/27187, WO-A- 97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270, WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, US-A-5 804 532, US-A-5 834402, US-A-5 846 906, US-A -5,863,865, WO-A-95/31466, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200, WO-A-96/26206, WO-A-97 / 27187, WO-A-97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270 , WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-
98/31682, WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327, WO-A-99/10328, WO-A-00/05221 und vor allem WO-A-00/21924). Die Wirkung dieser Verbindungen ist jedoch nicht in allen Belangen zufriedenstellend.98/31682, WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327, WO-A-99/10328, WO-A-00 / 05221 and especially WO-A-00/21924). However, the action of these compounds is not satisfactory in all respects.
Es wurden nun die neuen substituierten Arylketone der Formel (I)The new substituted aryl ketones of the formula (I)
in welcher in which
A1 für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), SO oder SO2 steht,
A2 für Alkandiyl (Alkylen), Alkendiyl oder Alkindiyl steht,A 1 represents a single bond or O (oxygen), S (sulfur), SO or SO 2 , A 2 represents alkanediyl (alkylene), alkenediyl or alkindiyl,
Q für O (Sauerstoff) oder S (Schwefel) steht,Q represents O (oxygen) or S (sulfur),
R1 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy,R 1 for hydrogen or for optionally substituted alkyl, alkoxy,
Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aryl oder Arylalkyl, oder für die Gruppierung -C(Q)-R2 steht,Alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or represents the group -C (Q) -R 2 ,
R2 für Wasserstoff, Animo, Cyanoamino, Nitroamino, Hydroxyamino, Hydra- zino, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylamino, Dialkylamino, Alkoxy- amino, N-Alkyl-alkoxyamino, Alkylhydrazino, Dialkylhydrazino, Alkenyl, Alkenyloxy, Alkenylamino, Alkenyloxyamino, Alkinyl, Alkinyloxy, Alkinyl- amino, Cycloalkyl, Cycloalkyloxy, Cycloalkylamino, Cycloalkylalkyl, Cyclo- alkylalkoxy, Cycloalkylalkylamino, Aryl, Arylcarbonyl, Aryloxy, Aryloxy- carbonyl, Arylthio, Arylamino, Arylhydrazino, Arylalkyl, Arylalkoxy, Aryl- alkylthio, Arylalkylamino, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio, Heterocyclylamino, Heterocyclylalkyl, Heterocyclylalkoxy, Heterocyclyl- alkylthio oder Heterocyclylalkylamino steht,R 2 represents hydrogen, animo, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, dialkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, Alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylamino, arylaminoalkyl Arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,
X für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Dialkylamino- sulfonyl steht,X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
Y für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Dialkylamino- sulfonyl steht, und
für eine der nachstehenden Gruppierungen stehtY represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and represents one of the groupings below
wobeiin which
m für die Zahlen 0 bis 6 steht,m represents the numbers 0 to 6,
R für Wasserstoff, Halogen oder für jeweils gegebenenfalls substituiertesR represents hydrogen, halogen or optionally substituted in each case
Alkyl, Alkylthio oder Aryl steht, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff oder Alkandiyl (Alkylen) steht,Represents alkyl, alkylthio or aryl, or - if m represents 2 - optionally also together with a second radical R 3 represents oxygen or alkanediyl (alkylene),
R4 für Hydroxy, Formyloxy, Halogen, oder für jeweils gegebenenfalls substituiertes Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkyl- carbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyloxy, Alkyl- sulfonyloxy, Alkenyloxy, Alkinyloxy, Aryloxy, Arylthio, Aryl- sulfinyl, Arylsulfonyl, Arylcarbonyloxy, Arylcarbonylalkoxy, Aryl- sulfonyloxy, Arylalkoxy, Arylalkylthio, Arylalkylsulfinyl oder Aryl- alkylsulfonyl steht,R 4 for hydroxyl, formyloxy, halogen, or for optionally substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonate Arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl,
R5 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkoxycarbonyl oder Cycloalkyl steht,R 5 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
R6 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aryl oder Arylalkyl steht,
R7 für Hydroxy, Formyloxy, oder für jeweils gegebenenfalls substituiertes Alkoxy, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylamino- carbonyloxy, Alkylsulfonyloxy, Alkenyloxy, Alkinyloxy, Arylalkoxy, Arylcarbonyloxy, Arylcarbonylalkoxy oder Arylsulfonyloxy steht,R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, R 7 represents hydroxy, formyloxy, or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
R8 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfmyl oder Alkylsulfonyl steht,R 8 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfmyl or alkylsulfonyl,
R9 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht,R 9 represents hydrogen or represents optionally substituted alkyl or cycloalkyl,
R10 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht, undR 10 represents hydrogen or represents optionally substituted alkyl or cycloalkyl, and
R1 ' für Wasserstoff, Cyano, Carbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfmyl oder Alkylsulfonyl steht,R 1 'represents hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfmyl or alkylsulfonyl,
gefunden.found.
Der Rest X steht bevorzugt an Position (2) des Phenylrings.The radical X is preferably at position (2) of the phenyl ring.
In den Definitionen sind die Kohlenwasserstoffketten, wie Alkyl oder Alkandiyl - auch in Verbindung mit Heteroatomen, wie in Alkoxy - jeweils geradkettig oder verzweigt.
Soweit die Verbindungen der allgemeinen Formel (I) in verschiedenen stereoisomeren Formen existieren können, schließt die Erfindung die jeweils möglichen stereoisomeren Formen mit ein.In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched. Insofar as the compounds of the general formula (I) can exist in various stereoisomeric forms, the invention includes the stereoisomeric forms which are possible in each case.
Bevorzugte Substituenten bzw. bevorzugte Bereiche der in den oben und nachstehend aufgeführten Formeln vorhandenen Reste werden im Folgenden definiert.Preferred substituents or preferred ranges of the radicals present in the formulas listed above and below are defined below.
A1 steht bevorzugt für O oder für eine Einfachbindung.A 1 preferably represents O or a single bond.
A2 steht bevorzugt für Alkandiyl (Alkylen), Alkendiyl oder Alkindiyl mit j eweils bis zu 6 Kohlenstoffatomen.A 2 preferably represents alkanediyl (alkylene), alkenediyl or alkindiyl, each having up to 6 carbon atoms.
Q steht bevorzugt für O (Sauerstoff).Q is preferably O (oxygen).
R1 steht bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano,R 1 preferably represents hydrogen, in each case optionally by cyano,
Halogen, C1-C4-Alkoxy, C1-C4-Alkylthio, - - Alkylsulfmyl oder -Q- Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl oder Alkylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für Dialkylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder C1-C4- Alkyl substituiertes Cycloalkyl oder Cycloalkylalkyl mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkyl- teil, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, C1-C4-Alkyl,Halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, - - alkylsulfmyl or -Q- alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkylamino each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino each with 1 to 4 carbon atoms in the alkyl groups, each for alkenyl or alkynyl optionally substituted by cyano or halogen, each with 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C 1 -C 4 alkyl up to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C 1 -C 4 -alkyl,
Cι-C4-Halogenalkyl, C1-C4-Älkoxy oder Ci-C4-Halogenalkoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Aryl- gruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für die Gruppierung -C(Q)-R2.
steht bevorzugt für Wasserstoff, Ammo, Cyanoamino, Nitroamino, Hydroxy- amino, Hydrazino, für C1-C4-Alkyl-carbonyl, für Q- -Alkoxy-carbonyl, für jeweils gegebenenfalls durch Cyano, Halogen, C1-C4-Alkoxy, C1-C4-Alkyl- thio, -Q- Alkylsulfmyl oder C1-C -Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Alkoxyamino oder Alkylhydrazino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für Dialkylamino, N- Alkyl-alkoxyamino oder Dialkylhydrazmo mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkenyloxyamino, Alkinyl, Alkinyloxy oder Alkinylamino mit jeweils 2 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder C1-C4-Alkyl substituiertes Cycloalkyl, Cycloalkyloxy, Cycloalkylamino, Cycloalkylalkyl, Cycloalkyl- alkoxy oder Cycloalkylalkylamino mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, - -Cι-C 4 haloalkyl, C 1 -C 4 -Älkoxy or Ci-C 4 each having 6 or 10 carbon atoms group haloalkoxy substituted aryl or arylalkyl in the aryl and optionally 1 to 4 carbon atoms in the alkyl part, or represents the grouping - C (Q) -R 2 . preferably represents hydrogen, ammo, cyanoamino, nitroamino, hydroxyamino, hydrazino, C 1 -C 4 -alkylcarbonyl, Q- -alkoxy-carbonyl, each optionally by cyano, halogen, C 1 -C 4 - Alkoxy, C 1 -C 4 alkylthio, -Q- alkylsulfmyl or C 1 -C 4 -alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxyamino or alkylhydrazino, each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino, N- Alkyl-alkoxyamino or dialkylhydrazmo each having 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino, each optionally substituted by halogen, each having, if appropriate, cyano, halogen or C 1 -C 4 alkyl substituted cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl group and optionally all 1 to 4 carbon atoms in the alkyl part, each optionally with nitro, cyano, halogen, - -
Alkyl, C1-C -Halogenalkyl, - -Alkoxy, Ci-C4-Halogenalkoxy oder d-C4- Alkoxy-carbonyl substituiertes Aryl, Arylcarbonyl, Aryloxy, Aryloxycarb- onyl, Arylthio, Arylamino, Arylhydrazino, Arylalkyl, Arylalkoxy, Arylalkyl- thio oder Arylalkylamino mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, Cι-C4-Alkyl, C1-C4- Halogenalkyl, C1-C4-Alkoxy, d-C4-Halogenalkoxy, -C4- Alkylthio, CrC - Halogenalkylthio oder d-C -Alkoxy-carbonyl substituiertes monocyclisches oder bicyclisches Heterocyclyl, Heterocyclyloxy, Heterocyclylthio, Hetero- cyclylamino, Heterocyclylalkyl, Heterocyclylalkoxy, Heterocyclylalkylthio oder Heterocyclylalkylamino, wobei jeweils die Heterocyclyl-Gruppierung bis zu 10 Kohlenstoffatome und zusätzlich mindestens ein Heteroatom ausgewählt aus der Reihe Stickstoff (N) (höchstens jedoch 5 N- Atome), Sauerstoff (O) (höchstens jedoch 2 O-Atome), Schwefel (S) (höchstens jedoch 2 S- Atome), SO oder SO2 sowie gegebenenfalls zusätzlich eine Gruppe ausge-
wählt aus Oxo (C=O), Thioxo (C=S), Imino (C=NH), Cyanoimino (C=N- CN), Nitroimino (C=N-NO2) enthält.Alkyl, C 1 -C -haloalkyl, - -alkoxy, Ci-C 4 -haloalkoxy or dC 4 - alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally substituted by nitro, cyano, halo, Cι-C 4 alkyl, C 1 -C 4 - haloalkyl, C 1 -C 4 alkoxy, dC 4 -haloalkoxy, -C 4 - alkylthio, CrC - haloalkylthio or C alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylthio, hetero- cyclylamino, heterocyclylalkyl, heterocyclylalkoxy, Heterocyclylalkylthio or heterocyclylalkylamino, wherein in each case the heterocyclyl -Grouping up to 10 carbon atoms and additionally at least one heteroatom selected from the series nitrogen (N) (but not more than 5 N atoms), oxygen (O) (but not more than 2 O atoms), sulfur (S) (but no more than 2 S atoms), SO or SO 2 and, if necessary, an additional group selects from oxo (C = O), thioxo (C = S), imino (C = NH), cyanoimino (C = N-CN), nitroimino (C = N-NO 2 ).
X steht bevorzugt für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen, d-Q-AIkoxy, CrC4- Alkylthio, CrC4- Alkylsulfmyl oder CrC4-Alkylsulf- onyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkylamino, Dialkylammo oder Dialkylaminosulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen.X preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or in each case optionally by cyano, halogen, dQ-alkoxy, C r C 4 - alkylthio, C r C 4 - alkylsulfmyl or C r C 4 - Alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylammo or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.
Y steht bevorzugt für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen, d-C4-Alkoxy, CrC4-Alkylthio, CrC4- Alkylsulfmyl oder CrC4- Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkylamino, Dialkylammo oder Dialkylaminosulfonyl mit jeweils 1 bis 6Y preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally by cyano, halogen, dC 4 alkoxy, C r C 4 alkylthio, C r C 4 alkylsulfmyl or C r C 4 - Alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylammo or dialkylaminosulfonyl, each with 1 to 6
Kohlenstoffatomen in den Alkylgruppen.Carbon atoms in the alkyl groups.
Z steht bevorzugt für eine der nachstehenden GruppierungenZ preferably represents one of the groupings below
m steht bevorzugt für die Zahlen 0 bis 3.m preferably represents the numbers 0 to 3.
R3 steht bevorzugt für Wasserstoff, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, d-C4-Alkoxy, C1-C4-Alkylthio, d-C -Alkylsulfinyl oderR 3 preferably represents hydrogen, halogen, in each case optionally by cyano, halogen, dC 4 -alkoxy, C 1 -C 4 -alkylthio, dC -alkylsulfinyl or
C1-C4-Alkylsulfonyl substituiertes Alkyl oder Alkylthio mit jeweils 1 bis 6C 1 -C 4 alkylsulfonyl-substituted alkyl or alkylthio each having 1 to 6
Kohlenstoffatomen, oder für Phenyl, oder - für den Fall, dass m für 2 steht
- gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff oder Alkandiyl (Alkylen) mit 3 bis 5 Kohlenstoffatomen.Carbon atoms, or for phenyl, or - in the event that m is 2 - optionally together with a second radical R 3 for oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms.
R4 steht bevorzugt für Hydroxy, Formyloxy, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, Cι-C4-Alkoxy, d-C4- Alkylthio, d-C - Alkylsulfmyl oder d-C4- Alkylsulfonyl substituiertes Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyl- oxy oder Alkylsulfonyloxy mit jeweils 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyloxy oder Alkinyloxy mit jeweils 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Nitro,R 4 preferably represents hydroxy, formyloxy, halogen, in each case optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, dC 4 - alkylthio, dC - alkylsulfmyl or dC 4 - alkylsulfonyl-substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, Alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, each for alkenyloxy optionally substituted by halogen or alkynyloxy each having 3 to 6 carbon atoms, each for optionally using nitro,
Cyano, Halogen, d-C4-Alkyl, d-C4-Halogenalkyl, C1-C -Alkoxy, d-C4- Halogenalkoxy, d-C - Alkylthio, d-C4-Halogenalkylthio, d-C4-Alkyl- sulfmyl, d-C4-Halogenalkylsulfinyl, d-C4-Alkylsulfonyl oder d-C4-Halo- genalkylsulfonyl substituiertes Aryloxy, Arylthio, Arylsulfinyl, Arylsulfonyl, Arylcarbonyloxy, Arylcarbonylalkoxy, Arylsulfonyloxy, Arylalkoxy, Aryl- alkylthio, Arylalkylsulfinyl oder Arylalkylsulfonyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil.Cyano, halogen, C 4 alkyl, dC 4 haloalkyl, C 1 -C alkoxy, dC 4 - haloalkoxy, dC - alkylthio, haloalkylthio 4 dC, dC 4 alkyl sulfmyl, dC 4 haloalkylsulfinyl, dC 4 - alkylsulfonyl or C 4 -Halo- genalkylsulfonyl substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, Arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, aryl, alkylthio, arylalkylsulfinyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.
R5 steht bevorzugt für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl,R 5 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl,
Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, d-C4- Alkoxy, d-C4- Alkylthio, d-C4-Alkylsulfϊnyl oder d-C4- Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfmyl, Alkylsulfonyl oder Alkoxycarbonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen oder für gege- benenfalls durch Cyano, Halogen oder d-C4-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen.Halogen, in each case optionally cyano-, halogen, C 4 - alkoxy, dC 4 - alkylthio, dC 4 -Alkylsulfϊnyl or C 4 - substituted alkylsulfonyl, alkyl, alkoxy, alkylthio, Alkylsulfmyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or d-C4-alkyl.
R6 steht bevorzugt für Wasserstoff, für gegebenenfalls durch Cyano, Halogen, Cι-C4-Alkoxy, d-C4-Alkylthio, C1-C4-Alkylsulfmyl oder d-C4-Alkyl- sulfonyl substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyl oder Alkinyl mit
jeweils 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder d-C4- Alkyl substituiertes Cycloalkyl oder Cycloalkylalkyl mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C4-Alkyl, Cι-C4-Halogenalkyl, d-C4-R 6 preferably represents hydrogen, represents optionally cyano-, halogen, Cι-C 4 alkoxy, dC 4 alkylthio, C 1 -C 4 -Alkylsulfmyl or C 4 alkyl sulfonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case alkenyl or alkynyl optionally substituted by cyano or halogen in each case 3 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl each optionally substituted by cyano, halogen or dC 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen , dC 4 -alkyl, C 4 haloalkyl, dC 4 -
Alkoxy, d-C4-Halogenalkoxy, d-C4- Alkylthio, C1-C4-Halogenalkylthio, d- C4-Alkylsulfinyl, d-C4-Halogenalkylsulfinyl, d-C4- Alkylsulfonyl oder d- C4-Halogenalkylsulfonyl substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlen- stoffatomen im Alkylteil.Alkoxy, dC 4 -haloalkoxy, dC 4 - alkylthio, C 1 -C 4 -haloalkylthio, d- C 4 -alkylsulfinyl, dC 4 -haloalkylsulfinyl, dC 4 - alkylsulfonyl or d- C 4 -haloalkylsulfonyl-substituted aryl or arylalkyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
R7 steht bevorzugt für Hydroxy, Formyloxy, für jeweils gegebenenfalls durch Cyano, Halogen oder d-C4- Alkoxy substituiertes Alkoxy, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyloxy oder Alkylsulfonyloxy mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyloxy oder Alkinyl- oxy mit jeweils 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C4-Alkyl, C1-C4-Halogenalkyl, d-C4- Alkoxy, d-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylfhio, d- C -Alkylsulfinyl, d-C4-Halogenalkylsulfinyl, d-C4-Alkylsulfonyl oder Ci-R 7 preferably represents hydroxyl, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or dC 4 -alkoxy, for alkenyloxy optionally substituted by cyano or halogen or alkynyl oxy each having 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, C 4 alkyl, C 1 -C 4 haloalkyl, dC 4 - alkoxy, dC 4 -haloalkoxy, C 1 -C 4 -Alkylthio, C 1 -C 4 -Halogenalkylfhio, d- C -Alkylsulfinyl, dC 4 -Halogenalkylsulfinyl, dC 4 -Alkylsulfonyl or Ci-
C4-Halogenalkylsulfonyl substituiertes Arylalkoxy, Arylcarbonyloxy, Aryl- carbonylalkoxy oder Arylsulfonyloxy mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil.C 4 haloalkylsulfonyl substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
R8 steht bevorzugt für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder d-C - Alkoxy substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen.
R9 steht bevorzugt für Wasserstoff, für gegebenenfalls durch Cyano, Halogen oder Cj-C4-Alkoxy substituiertes Alkyl, oder für gegebenenfalls durch Cyano, Halogen oder d-C4-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoff- atomen.R 8 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups and optionally substituted by cyano, halogen or dC-alkoxy , R 9 preferably represents hydrogen, alkyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or dC 4 alkyl.
R10 steht bevorzugt für Wasserstoff, für gegebenenfalls durch Cyano, Halogen oder d-C4-Alkoxy substituiertes Alkyl, oder für gegebenenfalls durch Cyano, Halogen oder Cι-C4-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoff- atomen.R 10 preferably represents hydrogen, alkyl which is optionally substituted by cyano, halogen or dC 4 -alkoxy, or cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl.
R1 ! steht bevorzugt für Wasserstoff, Cyano, Carbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder d-C - Alkoxy substituiertes Alkyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen.R 1! preferably represents hydrogen, cyano, carbamoyl, halogen, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and is optionally substituted by cyano, halogen or dC-alkoxy.
A2 steht besonders bevorzugt für Methylen (-CH2-), Efhan-l,l-diyl (-CH(CH3)-)5 A 2 particularly preferably represents methylene (-CH 2 -), Efhan-l, l-diyl (-CH (CH 3 ) -) 5
Ethan-l,2-diyl (Dimethylen, -CH2CH2-), Propan-l,l-diyl (-CH(C2H5)-)5 Ethane-l, 2-diyl (dimethylene, -CH 2 CH 2 -), propane-l, l-diyl (-CH (C 2 H 5 ) -) 5
Propan-l,2-diyl (-CH(CH3)CH2-), Propan-l,3-diyl (-CH2CH2CH2-), Butan- 1,3-diyl (-CH(CH3)CH2CH2-), Butan- 1,4-diyl (-CH2CH2CH2CH2-), Ethen- diyl, Propendiyl, Butendiyl, Ethindiyl, Propindiyl oder Butindiyl.Propane-1,2-diyl (-CH (CH 3 ) CH 2 -), propane-1,3-diyl (-CH 2 CH 2 CH 2 -), butane-1,3-diyl (-CH (CH 3 ) CH 2 CH 2 -), butane-1,4-diyl (-CH 2 CH 2 CH 2 CH 2 -), ethylenediyl, propendiyl, butenediyl, ethindiyl, propindiyl or butindiyl.
R1 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-R 1 particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i -
Propylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfϊnyi, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethyl-
amino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, für Dimethyl- amino oder Diethylamino, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Pentenyl, Ethinyl, Propinyl, Butinyl oder Pentinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl oder Propyl substituiertes Cyclopropyl,Propylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i- Propylsulfϊnyi, methylsulfonyl, ethylsulfonyl, methylamino, ethyl amino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for each optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, pentenyl, ethynyl , Propynyl, butynyl or pentynyl, for each cyclopropyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl,
Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl oder Cyclohexylmethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Di- fluormethoxy oder Trifluormethoxy substituiertes Phenyl, Naphthyl, Phenyl- methyl, Phenylethyl, Naphthylmethyl oder Naphthylethyl oder für die Gruppierung -C(Q)-R2.Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl or for the grouping -C (Q) -R 2 .
steht besonders bevorzugt für Wasserstoff, Amino, Cyanoamino, Nitroamino, Hydroxyamino, Hydrazino, für jeweils gegebenenfalls durch Cyano, Fluor,particularly preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, each optionally by cyano, fluorine,
Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Pro- poxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Methoxyamino, Ethoxyamino, n- oder i-Propoxy- amino, n-, i-, s- oder t-Butoxyamino, Methylhydrazino, Ethylhydrazino, n- oder i-Propylhydrazino, n-, i-, s- oder t-Butylhydrazino, für Dimethylamino, Diethylammo, N-Methyl-methoxyamino, Dimethylhydrazino oder Diethylhy- drazino, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Pentenyl, Ethinyl, Propinyl, Butinyl, Pentinyl, Propenyloxy, Butenyloxy, Pentenyloxy, Propenylfhio, Butenylthio, Pentenylthio, Propenylarnino, Butenylamino, Pentenylamino, Propenyloxyamino, Butenyloxy amino, Pentenyloxyamino, Ethinyl, Propinyl, Butinyl, Pentinyl,Chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, Methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, for dimethylamino, diethylammo, N-methyl-methoxyamino, dimethylhydrazino or diethylhydrazino, for ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentenyloxy, each optionally substituted by fluorine, chlorine and / or bromine , Propenylfhio, butenylthio, pentenylthi o, propenylarnino, butenylamino, pentenylamino, propenyloxyamino, butenyloxy amino, pentenyloxyamino, ethynyl, propynyl, butynyl, pentynyl,
Propinyloxy, Butinyloxy, Pentinyloxy, Propmylarnino, Butinylamino oder
Pentinylamino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl oder Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopen- tyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclo- hexyloxy, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclo- hexylamino, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl,Propynyloxy, butynyloxy, pentynyloxy, propylarnino, butynylamino or Pentinylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopentylamino, cyclohexylamino, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentyl- methoxy, Cyclohexylmethoxy, Cyclopropylmethylamino, Cyclobutylmethyl- amino, Cyclopentylmethylamino oder Cyclohexylmethylamino, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes Phenyl, Phenyl- carbonyl, Phenoxy, Phenoxycarbonyl, Phenylthio, Phenylamino, Phenyl- hydrazino, Naphthyl, Naphthyloxy, Naphtylthio, Naphfhylamino, Phenyl- mefhyl, Phenylethyl, Phenylmethoxy, Phenylethoxy, Phenylmethylthio,Cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-prop i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, Phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio, naphthylamino, phenylmefhyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio,
Phenyle hylthio, Phenylmethylamino, Phenylethylamino, Naphthylmethyl, Naphthylethyl, Naphfhylmethoxy, Naphthylethoxy, Naphthylmethylamino oder Naphthylethylamino, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Chlor- difluormethyl, Fluordichlormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylfhio, Difluormethylthio, Trifluor- methylthio, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes monocyclisches oder bicyclisches Heterocyclyl, Heterocyclyl- oxy, Heterocyclylamino, Heterocyclylalkyl, Heterocyclylalkoxy oder Hetero- cyclylalkylamino aus der Reihe Furyl, Furyloxy, Furylamino, Furylmethyl, Furylmethoxy, Furylmethylamino, Thienyl, Thienylmethyl, Pyrrolidinyl, Pyrrolidinylamino, Oxopyrrolidinyl, Pyrrolyl, Indolyl, Pyrrolylmethyl, Pyrazolyl, Pyrazolyloxy, Pyrazolylamino, Pyrazolylmefhyl, Imidazolyl,Phenyl hylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthhylmethoxy, naphthylethoxy, naphthylmethylamino or naphthylethylamino, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, , s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylfhio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl, heterycyll Heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy or heterocyclicalkylamino from the series furyl, furyloxy, furylamino, furylmethyl, furylmethoxy, furylmethylamino, thienyl, thienylmethyl, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, py rrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmefhyl, imidazolyl,
Imidazolylmethyl, 2-Oxo-l,3-diaza-cyclopentyl, Oxazolyl, Dihydrooxazolyl
(Oxazolinyl), Isoxazolyl, Dihydroisoxazolyl (Isoxazolinyl), Tetrahydro- isoxazolyl (Isoxazohdinyl), Oxazolylmethyl, Thiazolyl, Dihydrothiazolyl (Thiazolinyl), Tetrahydrothiazolyl (Thiazolidinyl), Thiazolylmethyl, Thi- azolidinyl, Oxothiazolidinyl, Cyanoiminothiazolidinyl, Oxotriazolinyl, Oxo- tetrazolinyl, Piperidinyl, Piperidinylamino, Oxopiperidinyl, 2-Oxo-l,3-diaza- cyclohexyl, 2-Oxo-l-aza-cycloheptyl, 2-Oxo-l,3-diaza-cycloheptyl,Imidazolylmethyl, 2-oxo-l, 3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl (Oxazolinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazohdinyl), oxazolylmethyl, thiazolyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl, thiazolidinyloxy, thiazololidiazolylethyl, thiazololidinylethyl, Piperidinylamino, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, 2-oxo-l-aza-cycloheptyl, 2-oxo-l, 3-diaza-cycloheptyl,
Morpholinyl, Morpholinylamino, Piperazinyl, Pyridinyl, Pyridinyloxy, Pyridinylamino, Pyridinylmethyl, Pyridinylmethoxy, Pyrimidinyl, Pyri- midinyloxy, Pyrimidinylmethyl, Pyrimidinylmethoxy.Morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl, pyrimidinylmethoxy.
X steht besonders bevorzugt für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituier- tes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i- Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i- Propylsulfmyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl- amino, Dimethylamino, Diethylammo, Dimethylarninosulfonyl oder Diethyl- aminosulfonyl.X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylammo, dimethylarninosulfonyl or diethylaminosulfonyl.
Y steht besonders bevorzugt für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, oder für jeweils gegebenen- falls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio,Y particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio,
Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i- Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i- Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl,Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i- propylsulfonyl,
Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butyl-
amino, Dimethylamino, Diethylamino, Dimethylaminosulfonyl oder Diethyl- aminosulfonyl.Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl- amino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
m steht besonders bevorzugt für die Zahlen 0, 1 oder 2.m particularly preferably represents the numbers 0, 1 or 2.
R steht besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Brom, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, oder für Phenyl, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff, Propan-l,3-diyl oder Butan- 1,4-diyl.R particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio , or for phenyl, or - if m is 2 - optionally together with a second radical R 3 for oxygen, propane-l, 3-diyl or butane-1,4-diyl.
R4 steht besonders bevorzugt für Hydroxy, Formyloxy, Fluor oder Chlor, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methyl- sulfϊnyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyloxy, Propionyl- oxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methylaminocarbonyloxy, Efhylaminocarbonyl- oxy, n- oder i-Propylammocarbonyloxy, Methylsulfonyloxy, Ethylsulfonyl- oxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluor- methylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Trifluormethylsulfonyl substituiertes Phenyloxy,
Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Phenylcarbonyloxy, Phenylcarb- onylalkoxy, Phenylsulfonyloxy, Phenylmethoxy, Phenylmethylthio, Phenyl- methylsulfinyl oder Phenylmethylsulfonyl.R 4 particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfonyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butoxycarbonyloxy, methoxy , Ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamineocarbonyloxy, n- or i-propylammocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propylene optionally substituted by fluorine, chlorine and / or bromine, in each case Butenyloxy, propynyloxy or butynyloxy, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl, Phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylalkoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.
R5 steht besonders bevorzugt für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor oder Brom, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propyl- fhio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclo- propyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl.R 5 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propyl-fhio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl, cyclobutyl, cyclopentyl or optionally substituted in each case by cyano, fluorine, chlorine, methyl or ethyl cyclohexyl.
R6 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Brom substituiertes Propenyl, Butenyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclo- propyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclo- butylmethyl, Cyclopentylmethyl oder Cyclohexylmethyl, oder für jeweils ge- gebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i- Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i- Propylthio, n-, i-, s- oder t-Butylthio, Difluormethylthio, Trifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Efhyl- sulfonyl oder Trifluormethylsulfonyl substituiertes Phenyl oder Phenyl- methyl.
R steht besonders bevorzugt für Hydroxy, Formyloxy, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-R 6 particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each for propenyl optionally substituted by cyano, fluorine, chlorine or bromine, butenyl, propynyl or butinyl, for each optionally substituted by cyano, fluorine, Chloro, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or if necessary by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- , s- or t-butylthio, difluoromethylthio, trifluoromethylthio, Met hylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl sulfonyl or trifluoromethylsulfonyl substituted phenyl or phenylmethyl. R particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. Butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-
Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n- oder i-Propylaminocarbonyloxy, Methylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Brom substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor,Propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each for propenyloxy optionally substituted by cyano, fluorine, chlorine or bromine, butenyloxy, propinyloxy or in each case optionally with nitinyloxy, or for , Cyano, fluorine, chlorine,
Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluor- methylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methyl- sulfonyl, Ethylsulfonyl oder Trifluormethylsulfonyl substituiertes Phenyl- methoxy, Phenylcarbonyloxy, Phenylcarbonylmethoxy oder Phenylsulfonyl- oxy.Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.
R8 steht besonders bevorzugt für Wasserstoff, Cyano, Carbamoyl, Thiocarb- amoyl, Fluor, Chlor oder Brom, oder für jeweils gegebenenfalls durch Cyano,R 8 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or in each case optionally by cyano,
Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Acetyl, Propionyl, n- oder i- Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propyl- thio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl.Fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, Methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
R9 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durchR 9 particularly preferably represents hydrogen, in each case optionally by
Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertesCyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted
Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, oder für jeweils gege- benenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclo- propyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl.
R10 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durchMethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl , R 10 particularly preferably represents hydrogen, in each case optionally by
Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertesCyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted
Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, oder für jeweils gege- benenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclo- propyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl.Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl ,
R11 steht besonders bevorzugt für Wasserstoff, Cyano, Carbamoyl, Fluor, Chlor oder Brom, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl.R 11 particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , Methylsulfonyl or ethylsulfonyl.
A2 steht ganz besonders bevorzugt für Methylen (-CH2-), Ethan-l,2-diyl (Di- methylen, -CH2CH2-) oder Propan-l,3-diyl (-CH2CH2CH2-).A 2 very particularly preferably represents methylene (-CH 2 -), ethane-1,2-diyl (dimethylene, -CH 2 CH 2 -) or propane-1,3-diyl (-CH 2 CH 2 CH 2 -).
R1 steht ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n- oder i-Butyl, für Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder.i-Propylfhio, Methylamino, Ethylamino, n- oder i-Propylamino, für Dimethylamino, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyl, Butenyl, Ethinyl,R 1 very particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, methyl, n- or i-propyl, n- or i -Butyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or.i-propylfhio, methylamino, ethylamino, n- or i-propylamino, for dimethylamino, for each optionally by fluorine and / or chlorine substituted propenyl, butenyl, ethynyl,
Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl oder Cyclohexylmethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluor-
ethoxy substituiertes Phenyl, Phenylmethyl oder Phenylethyl, oder für die Gruppierung -C(Q)-R2.Propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoro- ethoxy substituted phenyl, phenylmethyl or phenylethyl, or for the grouping -C (Q) -R 2 .
steht ganz besonders bevorzugt für Wasserstoff, Amino, Hydroxyamino, Hydrazino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy,very particularly preferably represents hydrogen, amino, hydroxyamino, hydrazino, in each case optionally by cyano, fluorine, chlorine, methoxy,
Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino, Methoxyamino, Ethoxyamino, n- oder i-Propoxyamino, für Dimethylamino, für N-Methyl-methoxyamino, für Dimethylhydrazino, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Ethenyl, Propenyl, Butenyl, Propenyloxy, Butenyloxy, Prope- nylthio, Butenylthio, Propenylamino, Butenylamino, Ethinyl, Propinyl, Buti- nyl, Propinyloxy, Butinyloxy, Propinylamino oder Butinylamino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl substituiertes Cyclo- propyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclo- butylmethyl, Cyclopentylmethyl oder Cyclohexylmethyl, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes Phenyl, Phenylamino, Phenylmethyl oder Phenylethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Difluormefhyl, Trifluormethyl, Dichlormethyl, Trichlormethyl,Ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, for dimethylamino, for N-methyl-methoxyamino, for dimethylhydrazino, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, in each case optionally substituted by fluorine and / or chlorine , Propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine or methyl, for each optionally substituted by nitro, cyano, fluorine, C. chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n - or i-propoxycarbonyl substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl,
Chlordifluormethyl, Fluordichlormethyl, Methoxy, Ethoxy, n- oder i- Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Difiuormethylthio, Trifluormethylthio, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes monocyclisches oder bicyclisches Heterocyclyl oder Heterocyclylalkyl aus der Reihe Furyl,Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or b-propylcyclo-cyclo-cyclo-cyclocylyl Heterocyclylalkyl from the Furyl series,
Furylmethyl, Thienyl, Thienylmethyl, Pyrrolidinyl, Oxopyrrolidinyl,
Pyrrolyl, Pyrrolylmethyl, Pyrazolyl, Pyrazolylmethyl, Imidazolyl, Imidazolylmethyl, 2-Oxo-l,3-diazacycloρentyl, Oxazolyl, Isoxazolyl, Oxazolylmethyl, Isoxazohdinyl, Thiazolyl, Thiazolylmethyl, Piperidinyl, Oxopiperidinyl, 2-Oxo-l,3-diazacyclohexyl, Morpholinyl, Piperazinyl, Pyridinyl, Pyridinyl- methyl, Pyrimidinyl, Pyrimidinylmethyl.Furylmethyl, thienyl, thienylmethyl, pyrrolidinyl, oxopyrrolidinyl, Pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl, imidazolylmethyl, 2-oxo-l, 3-diazacycloentyl, oxazolyl, isoxazolyl, oxazolylmethyl, isoxazohdinyl, thiazolyl, thiazolylmethyl, piperidacyl, 3-piperidinyl, oxy-diazidyl, oxy-3-piperidinyl, oxy-3-piperidinyl, oxy-3-piperidinyl, oxy-3-piperidinyl, Piperazinyl, pyridinyl, pyridinyl-methyl, pyrimidinyl, pyrimidinylmethyl.
X steht ganz besonders bevorzugt für Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n- oder i-Propyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Methoxymethyl, Methylthiomethyl, Methyl- sulfmylmethyl, Methylsulfonylmethyl, Methoxy, Ethoxy, Difluormethoxy,X very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfmylmethyl, methylsulfonylmethyl, methoxy , Ethoxy, difluoromethoxy,
Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl.Trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
Y steht ganz besonders bevorzugt für Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Methoxymethyl, Methylthiomethyl, Methylsulfinylmethyl, Methylsulfonylmethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl.Y very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoromethoxy, methyl Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
m steht ganz besonders bevorzugt für die Zahlen 0 oder 1.m very particularly preferably represents the numbers 0 or 1.
R3 steht ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, Methylthio, Ethylthio, n- oder i-Propylthio, oder für Phenyl, oder - für denR 3 very particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - for the
Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweitenCase where m stands for 2 - possibly also together with a second
Rest R3 für Sauerstoff, Propan-l,3-diyl oder Butan- 1,4-diyl.R 3 for oxygen, propane-1, 3-diyl or butane-1,4-diyl.
R4 steht ganz besonders bevorzugt für Hydroxy, für Formyloxy, für jeweils gege- benenfalls durch Fluor und/oder Chlor substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methyl-
sulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyloxy, Propionyl- oxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i- Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylaminocarbonyl- oxy, n- oder i-Propylaminocarbonyloxy, Methylsulfonyloxy, Efhylsulfonyl- oxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl- oxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Phenylcarbonyloxy, Phenyl- carbonylmethoxy, Phenylsulfonyloxy, Phenylmethoxy, Phenylmethylthio, Phenylmethylsulfinyl oder Phenylmethylsulfonyl.R 4 very particularly preferably stands for hydroxyl, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl- which is optionally substituted by fluorine and / or chlorine. sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxyoxy, n- or i-propylaminocarbonyloxyoxy, methyl- , n- or i-Propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine and / or chlorine, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylsulfonyl, phenylmethylsulfonyl or phenylmethylsulfonyl or phenylmethylsulfonyl or phenylmethylsulfonyl or phenylmethylsulfonyl or phenylmethylsulfonyl or phenylmethylsulfonyl, phenylmethylsulfonyl
R5 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, für jeweils gegebenenfalls durch Fluor und oder Chlor substituiertes Methyl,R 5 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, in each case methyl optionally substituted by fluorine and or chlorine,
Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl sub- stituiertes Cyclopropyl.Ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl.
R6 steht ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Propenyl, Butenyl, Propinyl oderR 6 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each in each case optionally propenyl, butenyl, propynyl or substituted by fluorine or chlorine
Butinyl, für jeweils gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl oder Phenylmethyl.
R7 steht ganz besonders bevorzugt für Hydroxy, für Formyloxy, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n- oder i-Propylaminocarbonyloxy, Mefhylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl- methoxy, Phenylcarbonyloxy, Phenylcarbonylmethoxy oder Phenylsulfonyl- oxy.Butinyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine or methyl, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenylmethyl. R 7 very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- which are each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methyl sulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally substituted by fluorine and / or chlorine, and / or Butenyloxy, propynyloxy or butynyloxy, or for phenyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy - methoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.
R8 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propyl- thio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl.R 8 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy. Butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
R9 steht ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl sub- stituiertes Cyclopropyl.R 9 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
R10 steht ganz besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl sub- stituiertes Cyclopropyl.
R11 steht ganz besonders bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl,R 10 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl which is optionally substituted by fluorine, chlorine or methyl. R 11 very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy. Propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,
Methylsulfonyl oder Ethylsulfonyl.Methylsulfonyl or ethylsulfonyl.
R1 steht am meisten bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, für Methoxy oder Ethoxy oder für die Gruppierung -C(Q)-R2.R 1 most preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, methoxy or ethoxy or the group -C (Q) -R 2 .
R2 steht am meisten bevorzugt für Wasserstoff, Amino, Hydrazino, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl oder n- oder i-Propyl, für Methylamino, Ethylamino, n- oder i-Propylamino oder Dimethylamino, für jeweils gegebenenfalls durch Fluor,R 2 most preferably represents hydrogen, amino, hydrazino, each methyl, ethyl or n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino, for each optionally by fluorine,
Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl oder n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Phenyl, Phenylamino, Phenylmethyl oder Phenyl- ethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor,Chloro or methyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, for each phenyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl or n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, Phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine,
Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Tri- chlormethyl, Chlordifluormethyl, Fluordichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylfhio, Trifluormethylthio, Methoxycarbonyl oder Ethoxycarbonyl substituiertes Furyl, Furylmethyl, Thienyl, Thienylmethyl, Pyrrolyl oder Pyrrolylmethyl.Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylfhio, trifluoromethylthio, methoxycarbonyl or ethoxycarbonyl-substituted furyl, furylmethyl, pyrylmethyl, methylmethyl, methylethyl, methylyl.
X steht am meisten bevorzugt für Wasserstoff, Nitro, Fluor, Chlor, Brom, Methyl, Ethyl oder Trifluormethyl.X most preferably represents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
Y steht am meisten bevorzugt für Wasserstoff, Nitro, Cyano, Fluor, Chlor,Y most preferably represents hydrogen, nitro, cyano, fluorine, chlorine,
Brom, Iod, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Tri-
chlormethyl, Methoxymethyl, Methylthiomethyl, Methylsulfinylmethyl, Methylsulfonylmethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl.Bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, tri- chloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
R steht am meisten bevorzugt für Wasserstoff oder j eweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl oder Ethyl.R most preferably represents hydrogen or methyl or ethyl which is optionally substituted by fluorine and / or chlorine.
R4 steht am meisten bevorzugt für Hydroxy.R 4 most preferably represents hydroxy.
R5 steht am meisten bevorzugt für Wasserstoff, Fluor, Chlor oder für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy.R 5 most preferably represents hydrogen, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine.
R6 steht am meisten bevorzugt für Wasserstoff oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl oder n-, i-, s- oder t-Butyl.R 6 most preferably represents hydrogen or methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.
R7 steht am meisten bevorzugt für Hydroxy, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Methoxy oder Ethoxy, oder für gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy oder Ethoxy substituiertes Phenylmethoxy.R 7 most preferably represents hydroxyl, in each case methoxy or ethoxy optionally substituted by fluorine or chlorine, or phenylmethoxy optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy.
Erfindungsgemäß bevorzugt sind die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.
Erfindungsgemäß besonders bevorzugt sind die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt.
Erfindungsgemäß ganz besonders bevorzugt sind die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred. According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß am meisten bevorzugt sind die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als am meisten bevorzugt aufgeführten Bedeutungen vorliegt.Most preferred according to the invention are the compounds of formula (I) in which there is a combination of the meanings listed as most preferred above.
Die Verbindungen der Formeln (1-1) bis (1-3) werden besonders hervorgehoben:The connections of formulas (1-1) to (1-3) are particularly emphasized:
A . 1 , A A 2 , Q r , τ R»l , τ R.2 , X, Y und Z haben hierbei jeweils die oben als bevorzugt oder ganz besonders bevorzugt angegebenen Bedeutungen.A. 1, A A 2, Q r, τ R »l, τ R.2, X, Y and Z each have the meanings given above as preferred or very particularly preferred.
Weiter werden die Verbindungen der allgemeinen Formeln (I-2A) bis (I-2D) besonders hervorgehoben:
The compounds of the general formulas (I-2A) to (I-2D) are particularly emphasized:
m, A1, A2, Q, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, X und Y haben hierbei jeweils die oben als bevorzugt oder ganz besonders bevorzugt angegebenen Bedeutungen.m, A 1 , A 2 , Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , X and Y each have the Meanings given above as preferred or very particularly preferred.
Von den Verbindungen der Formeln (I-l) bis (1-3) sowie (1-2 A) bis (I-2D) seien die- jenigen, bei denen A1 für eine Einfachbindung steht und A2 für Methylen steht, ganz besonders hervorgehoben.Of the compounds of the formulas (II) to (1-3) and (1-2 A) to (I-2D), those in which A 1 stands for a single bond and A 2 stands for methylene should be particularly emphasized ,
Von den Verbindungen der Formeln (I-l) bis (1-3) sowie (1-2 A) bis (I-2D) seien weiter auch diejenigen, bei denen A1 für O (Sauerstoff) steht und A2 für Ethan-1,2- diyl (Dimefhylen) steht, ganz besonders hervorgehoben.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden.Of the compounds of the formulas (II) to (1-3) and (1-2 A) to (I-2D) are also those in which A 1 is O (oxygen) and A 2 is ethane-1, 2-diyl (dimefhylene) is particularly highlighted. The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
Die neuen substituierten Arylketone der Formel (I) zeichnen sich durch starke und selektive herbizide Wirksamkeit aus.The new substituted aryl ketones of the formula (I) are notable for strong and selective herbicidal activity.
Man erhält die neuen substituierten Arylketone der Formel (I), wenn manThe new substituted aryl ketones of the formula (I) are obtained if
(a) Aminoverbindungen der allgemeinen Formel (II)(a) amino compounds of the general formula (II)
in welcher in which
A1, A2, R1, X, Y und Z die oben angegebene Bedeutung haben,A 1 , A 2 , R 1 , X, Y and Z have the meaning given above,
mit Verbindungen der allgemeinen Formel (m)with compounds of the general formula (m)
in welcher in which
Q und R2 die oben angegebene Bedeutung haben und
Q1 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio, bevorzugt für Chlor, Brom, Methoxy, Ethoxy, Methlfhio, Ethylthio, Phenyloxy oder Phenylthio steht,Q and R 2 have the meaning given above and Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
- oder gegebenenfalls mit entsprechenden Iso(thio)cyanaten -- or, if appropriate, with corresponding iso (thio) cyanates -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder wenn manor if you
(b) Carbonsäuren der allgemeinen Formel (TV)(b) carboxylic acids of the general formula (TV)
in welcher in which
A 1 , τ
R> l , D R2 , X und Y die oben angegebene Bedeutung habenA 1, τ R> 1, D R2, X and Y have the meaning given above
- oder reaktionsfähige Derivate hiervon, wie z.B. entsprechende Säurehalogenide, Säurecyanide oder Ester -- or reactive derivatives thereof, e.g. corresponding acid halides, acid cyanides or esters -
mit Verbindungen der allgemeinen Formel (V)with compounds of the general formula (V)
H-Z (V) in welcher
Z die oben angegebene Bedeutung hat,HZ (V) in which Z has the meaning given above,
gegebenenfalls in Gegenwart eines Dehydratisierungsmittel sowie gegebenen- falls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder wenn manor if you
(c) substituierte Benzoylketone der allgemeinen Formel (Ia)(c) substituted benzoyl ketones of the general formula (Ia)
in welcher in which
A , A L 2 , τ
R> l , τ R>2 , R , 10 , X und Y die oben angegebene Bedeutung haben,A, A L 2, τ R> l, τ R> 2, R, 10, X and Y have the meaning given above,
mit einem Orthoameisensäureester oder mit einem N,N-Dimethyl-formamid- acetal oder mit einem Cyanoameisensäureester oder mit Carbondisulfid (Schwefelkohlenstoff) und einem Alkylierungsmittel und anschließend mit Hydroxylamin oder einem Säureaddukt hiervonwith an orthoformic acid ester or with an N, N-dimethylformamide acetal or with a cyanoformic acid ester or with carbon disulfide (carbon disulfide) and an alkylating agent and then with hydroxylamine or an acid adduct thereof
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder wenn man
(d) Arylketone der allgemeinen Formel (VI)or if you (d) aryl ketones of the general formula (VI)
in welcher in which
R r> l1, X, Y und Z die oben angegebene Bedeutung haben und R r> l 1 , X, Y and Z have the meaning given above and
Q2 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio, bevorzugt für Chlor, Brom, Methoxy, Ethoxy, Methlthio, Ethylthio, Phenyloxy oderQ 2 for halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably for chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or
Phenylthio steht,Phenylthio stands,
- oder gegebenenfalls entsprechende Iso(thio)cyanate -- or, if appropriate, corresponding iso (thio) cyanates -
mit Verbindungen der allgemeinen Formel (VII)with compounds of the general formula (VII)
H-R2 (VII) in welcherHR 2 (VII) in which
R die oben angegebene Bedeutung hat,R has the meaning given above,
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
und gegebenenfalls im Aiischluss an die Durchführung der erfindungsgemäßen Verfahren (a), (b), (c) oder (d) an den so erhaltenen Verbindungen der
allgemeinen Formel (I) im Rahmen der Substituentendefinition Folgeumsetzungen (beispielsweise Substitutions-, Oxidations- oder Reduktionsreaktionen) zur Umwandlung in andere Verbindungen der allgemeinen Formel (I) nach üblichen Methoden durchführt.and, if appropriate, in connection with the implementation of processes (a), (b), (c) or (d) on the compounds of the thus obtained general formula (I) in the context of the definition of substituents, subsequent reactions (for example substitution, oxidation or reduction reactions) for conversion into other compounds of the general formula (I) by customary methods.
Verwendet man beispielsweise [3-(2-Amino-ethoxy)-2-chlor-4-methylthio-phenyl]- (5-ethyl-4-isoxazolyl)-methanon und Propionsäurechlorid als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (a) durch das folgende Formelschema skizziert werden:If, for example, [3- (2-amino-ethoxy) -2-chloro-4-methylthio-phenyl] - (5-ethyl-4-isoxazolyl) methanone and propionic acid chloride are used as starting materials, the course of the reaction in the process according to the invention (a ) are outlined by the following formula scheme:
Verwendet man beispielsweise 4-Brom-3-[[(l-pyrrolidinylthioxomethyl)-amino]- mefhyl]-benzoesäure und Cyclohexan-l,3-dion als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (b) durch das folgende Formelschema skizziert werden:If, for example, 4-bromo-3 - [[(l-pyrrolidinylthioxomethyl) amino] mefhyl] benzoic acid and cyclohexane-1,3-dione are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula become:
Verwendet man beispielsweise N-[2-Chlor-5-(3-cyclopropyl-3-oxo-propanoyl)- benzylj-acetamid, N,N-Dimethyl-formamid-diethylacetal und Hydroxylamin als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (c) durch das folgende Formelschema skizziert werden: If, for example, N- [2-chloro-5- (3-cyclopropyl-3-oxo-propanoyl) benzylj-acetamide, N, N-dimethylformamide diethylacetal and hydroxylamine are used as starting materials, the course of the reaction in the process according to the invention ( c) are sketched by the following formula scheme:
Verwendet man beispielsweise N-[[2-Brom-5-[(5-hydroxy-l-mefhyl-lH-pyrazol-4- yl)-carbonyl]-phenyl]-methyl]-carbamidsäure-O-methylester und Pyrrolidin als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Verfahren (d) durch das folgende Formelschema skizziert werden:If, for example, N - [[2-bromo-5 - [(5-hydroxy-1-methyl-1H-pyrazol-4-yl) carbonyl] phenyl] methyl] carbamic acid O-methyl ester and pyrrolidine are used as starting materials , the course of the reaction in process (d) according to the invention can be outlined using the following formula:
Die beim erfindungsgemäßen Verfahren (a) zur Herstellung von Verbindungen der allgemeinen Formel (I) als Ausgangsstoffe zu verwendenden Aminoverbindungen sind durch die Formel (II) allgemein definiert. In der allgemeinen Formel (II) habenThe amino compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (II). In the general formula (II)
1 9 11 9 1
A , A , R , X, Y und Z vorzugsweise diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der all-
gemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für A1, A2, R1, X, Y und Z angegeben worden sind.A, A, R, X, Y and Z are preferably those meanings which have already been mentioned above in connection with the description of the compounds according to the invention of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for A 1 , A 2 , R 1 , X, Y and Z have been given.
Die Ausgangsstoffe der allgemeinen Formel (II) sind noch nicht aus der Literatur be- kannt; sie sind als neue Stoffe auch Gegenstand der vorliegenden Anmeldung.The starting materials of the general formula (II) are not yet known from the literature; as new substances, they are also the subject of the present application.
Man erhält die neuen Aminoverbmdungen der allgemeinen Formel (II), wenn man Halogenverbindungen der allgemeinen Formel (VIII)The new amino compounds of the general formula (II) are obtained if halogen compounds of the general formula (VIII)
in welcher in which
A , 1 , A A 2 , X, Y und Z die oben angegebene Bedeutung haben undA, 1, A A 2, X, Y and Z have the meaning given above and
X1 für Halogen (vorzugsweise Fluor, Chlor, Brom oder Iod, insbesondere Chlor oder Brom) steht,X 1 represents halogen (preferably fluorine, chlorine, bromine or iodine, in particular chlorine or bromine),
mit Ammoniak oder Aminoverbindungen der allgemeinen Formel (IX)with ammonia or amino compounds of the general formula (IX)
in welcher in which
R1 die oben angegebene Bedeutung hat,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, wie z.B. Tetrahydrofuran, gegebenenfalls unter erhöhtem Druck bei Temperaturen zwischen 0°C und 100°C umsetzt (vgl. die Herstellungsbeispiele).R 1 has the meaning given above, if appropriate in the presence of a diluent, such as tetrahydrofuran, if appropriate under elevated pressure at temperatures between 0 ° C. and 100 ° C. (cf. the preparation examples).
Die Vorprodukte der allgemeinen Formel (VIII) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. WO-A-95/31446, WO-A- 00/68227, Herstellungsbeispiele).The precursors of the general formula (VIII) are known and / or can be prepared by processes known per se (cf. WO-A-95/31446, WO-A-00/68227, production examples).
Die Vorprodukte der allgemeinen Formel (IX) sind bekannte Synthesechemikalien.The precursors of the general formula (IX) are known synthetic chemicals.
Die beim erfindungsgemäßen Verfahren (a) zur Herstellung von Verbindungen der allgemeinen Formel (I) weiter als Ausgangsstoffe zu verwendenden (Thi)Oxover- bindungen sind durch die Formel (III) allgemein definiert. In der allgemeinen Formel (III) haben Q und R3 vorzugsweise diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevor- zugt oder am meisten bevorzugt für Q und R angegeben worden sind; Q steht vorzugsweise für Fluor, Chlor, Brom, d-C4-Alkoxy, C1-C4-Alkylthio, Phenoxy oder Phenylthio, insbesondere für Chlor, Methoxy, Ethoxy oder Phenoxy.Formula (III) provides a general definition of the (thi) oxo compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), Q and R 3 preferably have those meanings which are preferred, particularly preferred, very particularly preferred or most preferred for Q already in connection with the description of the compounds of the general formula (I) according to the invention and R have been specified; Q preferably represents fluorine, chlorine, bromine, dC 4 -alkoxy, C 1 -C 4 -alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.
Die Ausgangsstoffe der allgemeinen Formel QJ ) sind bekannte organische Synthesechemikalien.The starting materials of the general formula QJ) are known organic synthetic chemicals.
Die beim erfindungsgemäßen Verfahren (b) zur Herstellung von Verbindungen der allgemeinen Formel (I) als Ausgangsstoffe zu verwendenden Carbonsäuren sind durch die Formel (TV) allgemein definiert. In der allgemeinen Formel (TV) haben A1, A2, Q, R1, R2, X und Y vorzugsweise diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für A1, A2, Q, R1, R2, X und Y angegeben worden sind.
Die Ausgangsstoffe der allgemeinen Formel (IV) sind noch nicht aus der Literatur bekannt; sie sind als neue Stoffe auch Gegenstand der vorliegenden Anmeldung.Formula (TV) provides a general definition of the carboxylic acids to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (TV) A 1 , A 2 , Q, R 1 , R 2 , X and Y preferably have those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention preferably, very particularly preferably or most preferably for A 1 , A 2 , Q, R 1 , R 2 , X and Y have been given. The starting materials of the general formula (IV) are not yet known from the literature; as new substances, they are also the subject of the present application.
Man erhält die neuen Carbonsäuren der allgemeinen Formel (TV), wenn manYou get the new carboxylic acids of the general formula (TV) if you
(α) Iso(thio)cyanate der allgemeinen Formel (X)(α) iso (thio) cyanates of the general formula (X)
in welcher in which
A1, A2, Q, X und Y die oben angegebene Bedeutung haben undA 1 , A 2 , Q, X and Y have the meaning given above and
R für Wasserstoff, ein Alkalimetall- oder Erdalkalimetall-äquivalent (vorzugsweise ein Natrium oder Kalium), oder Alkyl (vorzugsweise d-C4- Alkyl, insbesondere Methyl oder Ethyl) steht,R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably dC 4 -alkyl, in particular methyl or ethyl),
mit Verbindungen der allgemeinen Formel (VII)with compounds of the general formula (VII)
H-R2 (VII) in welcherHR 2 (VII) in which
R2 die oben angegebene Bedeutung hat,R 2 has the meaning given above,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, wie z.B. Acetonitril oder Ethanol, bei Temperaturen zwischen 0°C und 100°C umsetzt und gegebenenfalls im Anschluss daran eine Esterverseifung nach üblichen Methoden durchführt (vgl. die Herstellungsbeispiele),
oder wenn manif appropriate in the presence of a diluent, such as, for example, acetonitrile or ethanol, at temperatures between 0 ° C. and 100 ° C. and, if appropriate, subsequently carrying out ester hydrolysis by customary methods (cf. the preparation examples), or if you
(ß) Aminoverbmdungen der allgemeinen Formel (XI)(β) amino compounds of the general formula (XI)
in welcher in which
A1, A2, R1, X und Y die oben angegebene Bedeutung haben undA 1 , A 2 , R 1 , X and Y have the meaning given above and
R für Wasserstoff, ein Alkalimetall- oder Erdalkalimetall-äquivalent (vorzugsweise ein Natrium oder Kalium), oder Alkyl (vorzugsweise Cι-C4- Alkyl, insbesondere Methyl oder Ethyl) steht,R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably C 1 -C 4 -alkyl, in particular methyl or ethyl),
mit (Thi)Oxoverbindungen der allgemeinen Formel (III)with (thi) oxo compounds of the general formula (III)
in welcher in which
Q und R2 die oben angegebene Bedeutung haben undQ and R 2 have the meaning given above and
Q1 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio, bevorzugt für Chlor, Brom, Methoxy, Ethoxy, Methylthio, Ethylthio, Phenyloxy oder Phenylthio steht,
- oder gegebenenfalls mit entsprechenden Iso(thio)cyanaten -Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio, - or, if appropriate, with corresponding iso (thio) cyanates -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel, wie z.B. Kaliumcarbonat oder Triethylamin, und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel, wie z.B. Acetonitril oder N,N-Di- methyl-formamid, bei Temperaturen zwischen 0°C und 100°C umsetzt.optionally in the presence of one or more reaction aids, e.g. Potassium carbonate or triethylamine, and optionally in the presence of one or more diluents, e.g. Acetonitrile or N, N-dimethyl-formamide, at temperatures between 0 ° C and 100 ° C.
Die beim erfindungsgemäßen Verfahren (b) zur Herstellung von Verbindungen der allgemeinen Formel (I) weiter als Ausgangsstoffe zu verwendenden Verbindungen sind durch die Formel (V) allgemein definiert. In der allgemeinen Formel (V) hat Z vorzugsweise diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für Z angegeben worden ist.Formula (V) provides a general definition of the compounds to be used further as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (V), Z preferably has the meaning which has already been given above as preferred, particularly preferred, very particularly preferred or most preferred for Z in connection with the description of the compounds of the general formula (I) according to the invention.
Die Ausgangsstoffe der allgemeinen Formel (V) sind bekannte organische Synthesechemikalien.The starting materials of the general formula (V) are known organic synthetic chemicals.
Die beim erfindungsgemäßen Verfahren (c) zur Herstellung von Verbindungen der allgemeinen Formel (I) als Ausgangsstoffe zu verwendenden substituierten Benzoyl- ketone sind durch die Formel (Ia) allgemein definiert. In der allgemeinen Formel (Ia) haben A1, A2, Q, R1, R2, R10, X und Y vorzugsweise diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für A1, A2, Q, R1, R2, R10, X und Y angegeben worden sind.Formula (Ia) provides a general definition of the substituted benzoyl ketones to be used as starting materials in process (c) according to the invention for the preparation of compounds of the general formula (I). In the general formula (Ia) A 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably, particularly preferably, very particularly preferably or most preferably for A 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y have been given.
Die Ausgangsstoffe der allgemeinen Formel (Ia) sind als neue Stoffe auch Gegenstand der vorliegenden Anmeldung; sie können nach den erfindungsgemäßen Ver- fahren (a) oder (b) hergestellt werden.
Die beim erfindungsgemäßen Verfahren (d) zur Herstellung von Verbindungen der allgemeinen Formel (I) als Ausgangsstoffe zu verwendenden Arylketone sind durch die Formel (VI) allgemein definiert. In der allgemeinen Formel (VI) haben A1, A2, Q, R1, X, Y und Z vorzugsweise diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oderThe starting materials of the general formula (Ia) are also the subject of the present application as new substances; they can be produced by processes (a) or (b) according to the invention. Formula (VI) provides a general definition of the aryl ketones to be used as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I). In the general formula (VI), A 1 , A 2 , Q, R 1 , X, Y and Z preferably have those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention , very particularly preferred or
1 9 1 9 am meisten bevorzugt für A , A , Q, R , X, Y und Z angegeben worden sind; Q steht vorzugsweise für Fluor, Chlor, Brom, d-C3-Alkoxy, d-d-Alkylthio, Phenoxy oder Phenylthio, insbesondere für Chlor, Methoxy, Ethoxy oder Phenoxy.1 9 1 9 most preferably have been given for A, A, Q, R, X, Y and Z; Q preferably represents fluorine, chlorine, bromine, dC 3 -alkoxy, dd-alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.
Die Ausgangsstoffe der Formel (VI) können nach dem Fachmann bekannten Verfahren hergestellt werden.The starting materials of the formula (VI) can be prepared by processes known to those skilled in the art.
Die beim erfindungsgemäßen Verfahren (d) zur Herstellung von Verbindungen der allgemeinen Formel (I) weiter als Ausgangsstoffe zu verwendenden Verbindungen sind durch die Formel (VII) allgemein definiert. In der allgemeinen Formel (VII) hat R2 vorzugsweise diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für R2 angegeben worden ist.Formula (VII) provides a general definition of the compounds to be used further as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I). In the general formula (VII), R 2 preferably has the meaning which has already been given above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for R 2 .
Die Ausgangsstoffe der allgemeinen Formel (VII) sind bekannte organische Verbindungen.The starting materials of the general formula (VII) are known organic compounds.
Die beim erfindungsgemäßen Verfahren ( ) zur Herstellung von Verbindungen der allgemeinen Formel (TV) als Ausgangsstoffe zu verwendenden Iso(fhio)cyanate sind durch die Formel (X) allgemein definiert. In der allgemeinen Formel (X) haben A1, A2, Q, X und Y vorzugsweise diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für A1, A2, Q, X undY angegeben worden ist.
Die Ausgangsstoffe der allgemeinen Formel (X) sind nach dem Fachmann bekannten Verfahren erhältlich.Formula (X) provides a general definition of the iso (fhio) cyanates to be used as starting materials in the process () according to the invention for the preparation of compounds of the general formula (TV). In the general formula (X), A 1 , A 2 , Q, X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for A 1 , A 2 , Q, X and Y has been specified. The starting materials of the general formula (X) can be obtained by processes known to those skilled in the art.
Die beim erfindungsgemäßen Verfahren (ß) zur Herstellung von Verbindungen der allgemeinen Formel (IV) als Ausgangsstoffe zu verwendenden Aminoverbindungen sind durch die Formel (XI) allgemein definiert. In der allgemeinen Formel (XI) haben A1, A2, R1, X und Y vorzugsweise diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der allgemeinen Formel (I) als bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder am meisten bevorzugt für A1, A2, R^ X und Y angegeben worden ist.Formula (XI) provides a general definition of the amino compounds to be used as starting materials in process (β) according to the invention for the preparation of compounds of the general formula (IV). In the general formula (XI), A 1 , A 2 , R 1 , X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most has preferably been given for A 1 , A 2 , R ^ X and Y.
Die Ausgangsstoffe der allgemeinen Formel (XI) sind nach dem Fachmann bekannten Verfahren herstellbar.The starting materials of the general formula (XI) can be prepared by processes known to those skilled in the art.
Die erfindungsgemäßen Verfahren (a), (b), (c) und (d) werden vorzugsweise unterThe processes (a), (b), (c) and (d) according to the invention are preferably carried out under
Verwendung eines oder mehrerer Reaktionshilfsmittel durchgeführt. Als Reaktionshilfsmittel für die erfindungsgemäßen Verfahren (a), (b), (c) und (d) kommen im allgemeinen die üblichen anorganischen oder organischen Basen oder Säureakzeptoren in Betracht. Hierzu gehören vorzugsweise Alkalimetall- oder Erdalkalimetall-, - acetate, -amide, -carbonate, -hydrogencarbonate, -hydride, -hydroxide oder -alkano- late, wie beispielsweise Natrium-, Kalium- oder Calcium-acetat, Lithium-, Natrium-, Kalium- oder Calcium-amid, Natrium-, Kalium- oder Calciurn-carbonat, Natrium-, Kalium- oder Calcium-hydrogencarbonat, Lithium-, Natrium-, Kalium- oder Calcium-hydrid, Lithium-, Natrium-, Kalium- oder Calcium-hydroxid, Natrium- oder Kalium-, -mefhanolat, -ethanolat, -n- oder -i-propanolat, -n-, -i-, -s- oder -t-butanolat; weiterhin auch basische organische Stickstoffverbindungen, wie beispielsweise Tri- methylamin, Triethylamin, Tripropylamin, Tributylamin, Ethyl-diisopropylamin, N,N-Dimethyl-cyclohexylamin, Dicyclohexylamin, Ethyl-dicyclohexylamin, N,N- Dimethyl-anilin, N,N-Dimefhyl-benzylamin, Pyridin, 2-Methyl-, 3-Methyl-, 4-Methyl-, 2,4-Dimethyl-, 2,6-Dimethyl-, 3,4-Dimethyl- und 3,5-Dimefhyl-pyridin,Performed using one or more reaction aids. Suitable reaction auxiliaries for processes (a), (b), (c) and (d) according to the invention are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal, acetate, amide, carbonate, bicarbonate, hydride, hydroxide or alkanoate, such as sodium, potassium or calcium acetate, lithium, sodium, Potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium -hydroxide, sodium or potassium, -mefhanolate, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimefethyl benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl pyridine,
5-Efhyl-2-methyl-pyridin, 4-Dimethylamino-pyridin, N-Methyl-piperidin, N-Ethyl-
piperidin, N-Methyl-morpholin, N-Ethyl-morpholin, l,4-Diazabicyclo[2.2.2]-octan (DABCO), l,5-Diazabicyclo[4.3.0]-non-5-en (DBN), oder 1,8-Diazabicyclo[5.4.0]- undec-7-en (DBU).5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl piperidine, N-methylmorpholine, N-ethylmorpholine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] - undec-7-ene (DBU).
Als weitere Reaktionshilfsmittel für die erfindungsgemäßen Verfahren (a), (b), (c) und (d) kommen auch Phasentransfer-Katalysatoren in Betracht. Als Beispiele für solche Katalysatoren seien genannt:Phase transfer catalysts are also suitable as further reaction aids for processes (a), (b), (c) and (d) according to the invention. Examples of such catalysts are:
Tetrabutylammonium-bromid, Tetrabutylammonium-chlorid, Tetraoctylammonium- chlorid, Tetiabutylammonium-hydrogensulfat, Methyl-trioctylammonium-chlorid,Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetiabutylammonium hydrogen sulfate, methyl trioctylammonium chloride,
Hexadecyl-trimethylammonium-chlorid, Hexadecyl-trimethylammonium-bromid, Benzyl-trimethylammonium-chlorid, Benzyl-triethylammonium-chlorid, Benzyl-tri- methylammonium-hydroxid, Benzyl-triethylammonium-hydroxid, Benzyl-tributyl- ammonium-chlorid, Benzyl-tributylammonium-bromid, Tetrabutylphosphonium- bromid, Tetrabutylphosphonium-chlorid, Tributyl-hexadecylphosphonium-bromid,Hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride, benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tribon bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributylhexadecylphosphonium bromide,
Butyl-triphenylphosphonium-chlorid, Ethyl-trioctylphosphonium-bromid, Tetraphe- nylphosphonium-bromid.Butyl triphenylphosphonium chloride, ethyl trioctylphosphonium bromide, tetraphenylphosphonium bromide.
Das erfindungsgemäße Verfahren (b) zur Herstellung der neuen substituierten Aryl- ketone der allgemeinen Formel (I) wird gegebenenfalls unter Verwendung eines De- hydratisierungsmittels durchgeführt. Es kommen hierbei die üblichen zur Bindung von Wasser geeigneten Chemikalien in Betracht.Process (b) according to the invention for the preparation of the new substituted aryl ketones of the general formula (I) is optionally carried out using a dehydrating agent. The usual chemicals suitable for binding water can be considered.
Als Beispiele hierfür werden Dicyclohexylcarbodiimid, Carbonyl-bis-imidazol und Propanphosphonsäureanhydrid genannt.Examples of these are dicyclohexylcarbodiimide, carbonyl-bis-imidazole and propanephosphonic anhydride.
Als besonders gut geeignete Dehydratisierungsmittel seien Dicyclohexylcarbodiimid und Propanphosphonsäureanhydrid genannt.Dicyclohexylcarbodiimide and propanephosphonic anhydride may be mentioned as particularly suitable dehydrating agents.
Die erfindungsgemäßen Verfahren zur Herstellung der Verbindungen der allgemeinen Formel (I) werden vorzugsweise unter Verwendung von Verdünnungsmitteln
durchgeführt. Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (a), (b), (c) und (d) kommen neben Wasser vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispiels- weise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolefher,The processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents carried out. Suitable diluents for carrying out processes (a), (b), (c) and (d) in addition to water are, in particular, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,
Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldi- methyl- oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-isobutyl- keton; Nitrile, wie Acetonitril, Propionitril oder Butyronitril; Amide, wie N,N-Di- methylformamid, N,N-Dimethylacetamid, N-Methyl-formanilid, N-Methyl-pyrroli- don oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester, Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmono- ethylether, Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, deren Gemische mit Wasser oder reines Wasser.Hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (a), (b), (c) und (d) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 150°C, vorzugsweise zwischen 10°C und 120°C.The reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c) and (d). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
Die erfindungsgemäßen Verfahren werden im allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, die erfindungsgemäßen Verfahren unter erhöhtem oder vermindertem Druck - im allgemeinen zwischen 0,1 bar und 10 bar - durch- zuführen.The processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
Zur Durcliführung der erfindungsgemäßen Verfahren werden die Ausgangsstoffe im allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuss zu verwenden. Die Umsetzung wird im allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsrnittels durchgeführt und das Reaktionsgemisch wird im all-
gemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele).To carry out the processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally agitated several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
Die erfindungsgemäßen Wirkstoffe können als Defoliants, Desiccants, Krautab- tötungsmittel und insbesondere als Unkrautvernichtungsmittel verwendet werden.The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
Unter Unkraut im weitesten Sinne sind alle Pflanzen zu verstehen, die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewendeten Menge ab.Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden:The active compounds according to the invention can e.g. can be used in the following plants:
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranfhus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,Dicotyledon weeds of the genera: Abutilon, Amaranfhus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippex, Rotal Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dikotyle Kulturen der Gattungen: Arachis, Beta, Brassica, Cucu is, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucu is, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monokotyle Unkräuter 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,Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriocha, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
Scirpus, Setaria, Sorghum.
Monokotyle Kulturen der Gattungen: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.Scirpus, Setaria, Sorghum. Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf dieseHowever, the use of the active compounds according to the invention is by no means limited to these
Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.Limited genera, but extends in the same way to other plants.
Die erfindungsgemäßen Wirkstoffe eignen sich in Abhängigkeit von der Konzentra- tion zur Totalunkrautbekämpfung, z.B. auf Industrie- und Gleisanlagen und aufDepending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
Wegen und Plätzen mit und ohne Baumbewuchs. Ebenso können die erfindungsgemäßen Wirkstoffe zur Unkrautbekämpfung in Dauerkulturen, z.B. Forst, Ziergehölz-, Obst-, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen, auf Zier- und Sportrasen und Weideflächen sowie zur selektiven Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden.Because of and places with and without tree cover. The active compounds according to the invention for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.
Die erfindungsgemäßen Verbindungen der Formel (I) zeigen starke herbizide Wirksamkeit und ein breites Wirkungsspektrum bei Anwendung auf dem Boden und auf oberirdische Pflanzenteile. Sie eignen sich in gewissem Umfang auch zur selektiven Bekämpfung von monokotylen und dikotylen Unkräutern in monokotylen und di- kotylen Kulturen, sowohl im Vorauflauf- als auch im Nachauflauf- Verfahren.The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
Die erfindungsgemäßen Wirkstoffe können in bestimmten Konzentrationen bzw. Aufwandmengen auch zur Bekämpfung von tierischen Schädlingen und pilzlichen oder bakteriellen Pflanzenkrankheiten verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.In certain concentrations or application rates, the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natür-
lich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Sproß, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Ernte- gut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including natural cultivated plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkom- mende Pflanzen (Unkräuter, Schadpflanzen) und/oder durch konventionelle biologische Zuchtmethoden, wie z.B. Kreuzung oder Protoplastenfύsion, erhaltenen Pflanzenarten und Pflanzensorten (Kulturpflanzen) sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden, gegebenenfalls in Kombination mit konventionellen Methoden, erhalten wurden (Genetically Modified Organismus) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert.As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plants (weeds, harmful plants) and / or by conventional organic breeding methods, such as e.g. Crossing or protoplast fύsion, preserved plant species and plant varieties (crop plants) and their parts treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organism) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" was explained above.
Unter Pflanzensorten versteht man Kulturpflanzen mit bestimmten Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Bio- und Genotypen sein.Plant varieties are cultivated plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
Zu den erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologischeThe transgenic plants or plant cultivars to be treated according to the invention include all plants which are genetically engineered
Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vor-
teilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wassersalz- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert derModification genetic material received, which these plants special gives some valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water salt or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value
Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. AlsHarvest products, higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. As
Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen wie Getreide (einschließlich Reis), Mais, Soja, Kartoffel, Baumwolle, Rüben, Raps, Kulturgräser wie Golf- und Zierrasen, Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrus- früchten und Weintrauben) und Plantagenkulturen wie Öl- und Gummibäume erwähnt, wobei Getreide (einschl. Reis), Mais, Soja, Kartoffel, Baumwolle, Rüben und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryΙA(c), CrylLA, CrylllA, CryπiB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenz- gene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen und Wirkstoffklassen wie Glyphosate oder Glufosinate / Phosphinotricin (z.B. "PAT"-Gen), ALS-Hemmstoffe wie Imida- zolinone, Sulfonylharnstoffe und andere, PPO-Hemmstoffe (z.B. Pflanzen mit Acuron - Genen), 4-HPD-Hemmstoffe wie Isoxazole (z.B. Isoxaflutole), ACCase -Examples of transgenic plants are the important crops such as cereals (including rice), corn, soybeans, potatoes, cotton, beets, rapeseed, cultivated grasses such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and plantation crops as mentioned oil and rubber trees, with cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed being particularly highlighted. The traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryIA (b), CryΙA (c), CrylLA, CrylllA, CryπiB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. As traits, the plant's increased tolerance to certain herbicidal active substances and classes of active substances such as glyphosate or glufosinate / phosphinotricin (eg "PAT" gene), ALS inhibitors such as imidazolinones, sulfonylureas and others, PPO, are also particularly emphasized Inhibitors (e.g. plants with Acuron genes), 4-HPD inhibitors such as isoxazoles (e.g. isoxaflutole), ACCase -
Hemmstoffe wie Sethoxydim, sowie Bromoxynil.
Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B.Inhibitors such as Sethoxydim, as well as Bromoxynil. The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g.
Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid-tolerante Pflanzen seien Maissorten, Baumwollsorten, Sojasorten, Getreidesorten einschließlich Reissorten, Rübensorten und Rapssorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegenCorn, Cotton, Soybean), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties, soy varieties, cereals including rice varieties, beet varieties and rapeseed varieties sold under the trade names Roundup Ready® (tolerance against
Glyphosate z.B. Mais, Baumwolle, Soja, Rüben, Raps), Liberty Link® (Toleranz gegen Glufosinate, z.B. Raps, Mais, Rüben), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais, Reis) erwähnt.Glyphosate e.g. Maize, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance to glufosinates, e.g. rapeseed, corn, beet), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize, rice).
Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig ent- wickelten genetischen Eigenschaften ("Traits").Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive ("synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen desDepending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or extensions of the
Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfϊndungsgemäß verwendbaren Stoffe und Mittel - auch in Kombination mit anderen agrochemischen Wirkstoffen - , besseres Pflanzenwachstum der Kulturpflanzen, erhöhte Toleranz der Kulturpflanzen gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz der Kulturpflanzen gegen Trockenheit oder gegen Wassersalz- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernte-
erträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Spectrum of activity and / or an enhancement of the effect of the substances and agents which can be used according to the invention - also in combination with other agrochemical active substances - better plant growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of the crop plants to drought or to water salt or Soil salinity, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest Yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects.
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit denThe plants listed can be particularly advantageous according to the invention with the
Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden, wobei zusätzlich zu der guten Bekämpfung der Unkrautpflanzen die obengenannten synergistischen Effekte mit den oben beschriebenen Pflanzen oder Pflanzensorten auftreten. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.Compounds of the general formula (I) or the active compound mixtures according to the invention are treated, in addition to the good control of the weed plants the above-mentioned synergistic effects occurring with the plants or plant cultivars described above. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirk- Stoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oderThe treatment of the plants and plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or
Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wieThe active ingredients can be converted into the usual formulations, such as
Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Mont- morillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit,Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,
Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgato- ren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B.Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and or foaming agents are possible: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweiß- hydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymefhylcellulose, natürliche und synthetische pulvrige, körnige oder latexfδrmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Herbiziden und/oder mit Stoffen, welche die Kul- turpflanzen-Verträglichkeit verbessern („Safenern") zur Unkrautbekämpfung verwendet werden, wobei Fertigformulierungen oder Tankmischungen möglich sind. Es sind also auch Mischungen mit Unkrautbekärnpfungsmitteln möglich, welche ein oder mehrere bekannte Herbizide und einen Safener enthalten.The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, as a mixture with known herbicides and / or with substances which improve crop plant tolerance ("safeners"), ready formulations or tank mixes being possible Mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
Für die Mischungen kommen bekannte Herbizide infrage, beispielsweise Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfüron, Amitrole, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Ben- zoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromacil, Bromo- butide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil (-allyl), Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlorfhiamid, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulf- uron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlobenil, Dichlorprop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenopenten (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr,Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benlububuluron, bezububuluron (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromacil, bromobutide, bromofenoxime, bromoxynil, butachlor , Butafenacil (-allyl), Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlorfhiamid, Chloridoluronethyl, Chidortoluronethyl , Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydimb, Cyutyl), Cyhalofyl -D , 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlobenil, Dichlorprop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenopenten (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr,
Dikegulac (-sodium), Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Di-
methenamid (-P), Dimexyflam, Dinitramine, Diphenamid, Diquat (-dibromide), Di- thiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Efhametsulf- uron (-methyl), Efhiozin, Ethofumesate, Efhoxyfen, Efhoxysulfüron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-M-isopropyl, -M-methyl), Flaza- sulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flu- chloralin, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi- propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flu- propacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxy- pyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fome- safen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-ammonium, -iso- propylammonium), Halosafen, Halosulfuron (-methyl), Haloxyfop (-ethoxyethyl, -P- methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imaze hapyr, rmazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxa- difen (-ethyl), Isoxaflutole, Isoxapyrifop, Ketospiradox, Lactofen, Lenacil, Linuron,Dikegulac (-sodium), dimefuron, dimepiperate, dimethachlor, dimethametryn, di- methenamide (-P), dimexyflam, dinitramine, diphenamide, diquat (-dibromide), di-thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, efhametsulfuron (-methyl), efhiozin, ethofumesulfate, efhoxoxy Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-M-isopropyl, -M-methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flu-chloralin , Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flu-propacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-bone), Flurol Fluroxypyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fome-safen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-ammonium, -isopropylammonium), Halosafen, Halosulfuron (-methyl ), Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imaze h apyr, rmazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxydifen (-ethyl), isoxaflutole, isoxapyrifop, ketospiradox, lactofenon, lenacil, linacil
MCPA, Mecoprop (-P), Mefenacet, Mesotrione, Metamitron, Metazachlor, Metha- benzthiazuron, Methyldymron, Metobenzuron, Metobromuron, (S-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Para- quat, Pelargonsäure, Pendimethalin, Pendralin, Pentoxazone, Pethoxamid, Phenmedi- pham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim,MCPA, Mecoprop (-P), Mefenacet, Mesotrione, Metamitron, Metazachlor, Metha benzthiazuron, Methyldymron, Metobenzuron, Metobromuron, (S-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Mononate, Moninate, Molinate, Molinate, Napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamide, phenmedi-phamophosphonosulfonyl, prima- lulfon, prinulfil (proline), picolinmethyl (proline), picolinmethyl (proline), prinulfil, prinulfil, (proline) ), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxoxy
Pyributicarb, Pyridafol, Pyridate, Pyridatol, Pyriftalid, Pyriminobac (-methyl), Pyri- thiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfen- trazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin,Pyributicarb, pyridafol, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydyn, simazine , Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin,
Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulf-
uron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifloxysulfuron, Trifluralin, Tri- flusulfuron (-methyl), Tritosulfuron.Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulf- uron, tribenuron (-methyl), triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron (-methyl), tritosulfuron.
Für die Mischungen kommen weiterhin bekannte Safener in Frage, beispielsweise AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-
24, Dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG- 191, Oxabetrinil, PPG-1292, R-29148.24, dichlormid, dymron, fenclorim, fenchlorazole (-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29,148th
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Fungiziden, Insektiziden, Akariziden, Nematiziden, Schutzstoffen gegen Vogelfraß, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln ist möglich.A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertigeThe active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use
Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Spritzen, Sprühen, Streuen.Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
Die erfindungsgemäßen Wirkstoffe können sowohl vor als auch nach dem Auflaufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
Die angewandte Wirkstoffmenge kann in einem größeren Bereich schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effektes ab. Im allgemeinen liegen die Aufwandmengen zwischen 1 g und 10 kg Wirkstoff pro Hektar Bodenfläche, vorzugsweise zwischen 5 g und 5 kg pro ha.The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den nachfolgenden Beispielen hervor.
Herstellungsbeispiele:The preparation and use of the active compounds according to the invention can be seen from the examples below. Preparation Examples:
Beispiel 1example 1
(Verfahren (a))(Method (a))
Zu einer Suspension von 1,0 g (2,9 mMol) [3-(2-Aminoethoxy)-2,4-dichlor-phenyl]- (l-ethyl-5-hydroxy-lH-pyrazol-4-yl)-methanon und 0,8 g (5,8 mMol) Kalium- carbonat in 6 ml Acetonitril gibt man 0,28 g (3,6 mMol) Acetylchlorid und rührt die Reaktionsmischung 24 Stunden bei Raumtemperatur (ca. 20°C). Danach wird das Lösungs-mittel unter vermindertem Druck entfernt und der Rückstand in wenig Wasser gelöst. Die wässrige Lösung wird mit Dichlormethan gewaschen, anschlie- ßend mit konz. Salzsäure angesäuert und mit Essigsäureethylester extrahiert. Die organische Phase wird mit gesättigter wässriger Natriumchlorid-Lösung gewaschen, über Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel unter vermindertem Druck sorgfältig abdestilliert.To a suspension of 1.0 g (2.9 mmol) [3- (2-aminoethoxy) -2,4-dichlorophenyl] - (l-ethyl-5-hydroxy-1H-pyrazol-4-yl) - methanone and 0.8 g (5.8 mmol) of potassium carbonate in 6 ml of acetonitrile are added 0.28 g (3.6 mmol) of acetyl chloride and the reaction mixture is stirred for 24 hours at room temperature (approx. 20 ° C). The solvent is then removed under reduced pressure and the residue is dissolved in a little water. The aqueous solution is washed with dichloromethane, then with conc. Acidified hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.
Man erhält 0,8 g (71,5 % der Theorie) N-(2-{2,6-Dichlor-3-[(l-ethyl-5-hydroxy-lH- pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamid (Beispiel 1-2-1) als orangegelben, glasartigen Feststoff.0.8 g (71.5% of theory) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy-1H-pyrazol-4-yl) carbonyl] - phenoxy} -ethyl) -acetamide (Example 1-2-1) as an orange-yellow, glassy solid.
Log P = 1,41.
Beispiel 2Log P = 1.41. Example 2
(Verfahren (a))(Method (a))
Zu einer Suspension von 0,5 g (1,45 mMol) [3-(2-Amino-ethoxy)-2,4-dichlor- phenyl]-(l-ethyl-5-hydroxy-lH-pyrazol-4-yl)-methanon in 10 ml Methanol gibt man 0,24 g (3,3 mMol) Methylsenföl (Methylisothiocyanat) und erhitzt die Reaktions- mischung 24 Stunden unter Rückfluss zum Sieden. Nach Zusatz von Wasser undTo a suspension of 0.5 g (1.45 mmol) [3- (2-amino-ethoxy) -2,4-dichlorophenyl] - (l-ethyl-5-hydroxy-1H-pyrazol-4-yl ) -methanone in 10 ml of methanol, 0.24 g (3.3 mmol) of methyl mustard oil (methyl isothiocyanate) is added and the reaction mixture is heated to boiling under reflux for 24 hours. After adding water and
Essigsäureethylester wird die organische Phase abgetrennt, mit gesättigter wässriger Natriumchlorid-Lösung gewaschen, über Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel unter vermindertem Druck sorgfältig abdestilliert.The organic phase is separated off in ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.
Man erhält 0,55 g (91 % der Theorie) N-(2-{2,6-Dichlor-3-[(l-ethyl-5-hydroxy-lH- pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-N,-methyl-thioharnstoff (Beispiel 1-2-2) als orangegelbes zähes Öl.0.55 g (91% of theory) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy-1H-pyrazol-4-yl) carbonyl] phenoxy} is obtained. -ethyl) -N , -methyl-thiourea (Example 1-2-2) as an orange-yellow viscous oil.
Log P = 1,60.
Log P = 1.60.
Beispiel 3Example 3
(Verfahren (b))(Method (b))
In 50 ml Acetonitril werden 0,7 g (6.25 mMol) 1,3-Cyclohexandion und 2,0 g (6.25 mMol) N-(3-Carboxy-2,6-dichlor-benzyl)-N'-isopropyl-thioharnstoff vorgelegt. Man versetzt die Mischung mit 1.5 g (7.25 mMol) Dicyclohexylcarbodiimid und rührt 15 Stunden bei Raumtemperatur (ca. 20°C). Danach werden 0.7 g (7 mMol) Triethyl- amin und 0.7 g (8 mMol) 2-Hydroxy-2-methyl-propionitril dazu gegeben und die Mischung wird weitere 15 Stunden bei Raumtemperatur gerülirt. Dann wird mit 50 ml wässriger lM-Kaliumcarbonatlösung verrührt, abgesaugt und das Filtrat mit Salzsäure auf pH 4 angesäuert. Man extrahiert 3 mal mit je 30 mL Dichlormethan, trock- net die vereinigten organischen Phasen mit Magnesiumsulfat und filtriert. Dann entfernt man das Lösungsmittel unter vermindertem Druck.0.7 g (6.25 mmol) of 1,3-cyclohexanedione and 2.0 g (6.25 mmol) of N- (3-carboxy-2,6-dichlorobenzyl) -N'-isopropyl-thiourea are placed in 50 ml of acetonitrile , 1.5 g (7.25 mmol) of dicyclohexylcarbodiimide are added to the mixture and the mixture is stirred for 15 hours at room temperature (approx. 20 ° C.). Then 0.7 g (7 mmol) of triethylamine and 0.7 g (8 mmol) of 2-hydroxy-2-methyl-propionitrile are added and the mixture is stirred for a further 15 hours at room temperature. The mixture is then stirred with 50 ml of aqueous 1M potassium carbonate solution, filtered off with suction and the filtrate is acidified to pH 4 with hydrochloric acid. It is extracted 3 times with 30 mL dichloromethane each time, the combined organic phases are dried with magnesium sulfate and filtered. The solvent is then removed under reduced pressure.
Man erhält 1.1 g (30 % der Theorie) N-(3-(Cyclohex-l-en-2-ol-6-on-l-ylcarbonyl)- 2,4-dichlorbenzyl)-N'-isopropyl-thioharnstoff (Beispiel 1-2-3) als öligen Rückstand.1.1 g (30% of theory) of N- (3- (cyclohex-1-en-2-ol-6-one-1-ylcarbonyl) -2,4-dichlorobenzyl) -N'-isopropyl-thiourea are obtained (example 1-2-3) as an oily residue.
LogP = 2.74.
LogP = 2.74.
Beispiel 4Example 4
(Folgeumsetzung)(Subsequent reaction)
Zu einer Lösung von 0,193 g (0,5 mMol) N-(2-{2,6-Dichlor-3-[(l-ethyl-5-hydroxy- lH-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamid in 6 ml Toluol gibt man 0,25 g (1,0 mMol) l-Brom-4-(brommethyl)-benzol und 0,15 g 1,8-Diazabicyclo- [5.4.0]-undec-7-en (DBU) und erhitzt die Reaktionsmischung 9 Stunden unter Rück- fiuss zum Sieden. Die überstehende Toluolphase wird abdekantiert und der verbleibende ölige Rückstand säulenchromatographisch mit Dichlormethan / Methanol (9 : 1) als Laufmittel getrennt.To a solution of 0.193 g (0.5 mmol) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy-1H-pyrazol-4-yl) carbonyl] phenoxy} -ethyl) -acetamide in 6 ml of toluene are added 0.25 g (1.0 mmol) of l-bromo-4- (bromomethyl) benzene and 0.15 g of 1,8-diazabicyclo- [5.4.0] -undec -7-ene (DBU) and refluxed the reaction mixture for 9 hours. The supernatant toluene phase is decanted off and the remaining oily residue is separated by column chromatography using dichloromethane / methanol (9: 1) as the eluent.
Man erhält 0,12 g (43 % der Theorie) N-{2-[3-({5-[(4-brom-benzyl)-oxy]-l-ethyl- lH-pyrazol-4-yl} -carbonyl)-2,6-dichlor-phenoxy]-efhyl} -acetamid (Beispiel 1-2-4) als gelbes zähes Öl.0.12 g (43% of theory) of N- {2- [3 - ({5 - [(4-bromo-benzyl) -oxy] -l-ethyl-1H-pyrazol-4-yl} -carbonyl is obtained ) -2,6-dichlorophenoxy] -efhyl} -acetamide (Example 1-2-4) as a yellow viscous oil.
Log P = 2,06.Log P = 2.06.
Analog zu den Beispielen 1 bis 4 sowie entsprechend der allgemeinen Beschreibung der erfindungsgemäßen Herstellungsverfahren können beispielsweise auch die in der nachstehenden Tabelle 1 aufgeführten Verbindungen der allgemeinen Formel (I) -
bzw. der Formeln (I-l) bis (1-3) bzw. der Formeln (1-2 A) bis (I-2D) - hergestellt werden.Analogously to Examples 1 to 4 and in accordance with the general description of the production processes according to the invention, for example the compounds of the general formula (I) listed in Table 1 below can also be or the formulas (II) to (1-3) or the formulas (1-2 A) to (I-2D).
Tabelle 1: Beispiele für die Verbindungen der Formel (1-2)Table 1: Examples of the compounds of the formula (1-2)
Tabelle 2: Beispiele für die Verbindungen der Formel (1-3)Table 2: Examples of the compounds of the formula (1-3)
Die Bestimmung der in den Tabellen angegebenen logP- erte erfolgte gemäß EEC- Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromato- graphy) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The logP values given in the tables were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
(a) Eluenten für die Bestimmung im sauren Bereich: 0,1% wässrige Phosphorsäure,(a) eluents for determination in the acidic range: 0.1% aqueous phosphoric acid,
Acetonitril; linearer Gradient von 10% Acetonitril bis 90% Acetonitril - entsprechende Messergebnisse sind in Tabelle 1 und 2 mit a) markiert.acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 and 2 with a ).
(b) Eluenten für die Bestimmung im neutralen Bereich: 0,01 -molare wässrige Phos- phatpuffer-Lösung, Acetonitril; linearer Gradient von 10% Acetonitril bis 90% Acetonitril - entsprechende Messergebnisse sind in Tabelle 1 und 2 mit b) markiert.(b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 and 2 with b ).
Die Eichung erfolgte mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP- Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinanderfolgendenThe calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive ones
Alkanonen).Alkanones).
Die lambda-max- Werte wurden an Hand der UV-Spektren von 200 nm bis 400 nm in den Maxima der chromatographischen Signale ermittelt.
The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
Ausgangsstoffe der Formel (II):Starting materials of formula (II):
Beispiel (II-l)Example (II-l)
Stufe 1step 1
Zu einer Lösung von 10,0 g (42,5 mMol) 2,4-Dichlor-3-hydroxy-benzoesäure-ethyl- ester in 100 ml Acetonitril gibt man 11,7 g (85,1 mMol) Kaliumcarbonat und nach 15 min 11,0 g (46,9 mMol) 2-Chlor-ethanoltosylat. Die Reaktionsmischung wird 19 Stunden bei 70°C gerührt, nach dem Abkühlen im Vakuum aufkonzentriert und der Rückstand mit 50 ml Wasser und 50 ml Dichlormethan versetzt. Die organische Phase wird abgetrennt, mit Wasser und gesättigter wässriger Natriumchlorid-Lösung gewaschen, über Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel unter vermindertem Druck sorgfältig äbdestilliert.11.7 g (85.1 mmol) of potassium carbonate are added to a solution of 10.0 g (42.5 mmol) of ethyl 2,4-dichloro-3-hydroxy-benzoate in 100 ml of acetonitrile, and after 15 min 11.0 g (46.9 mmol) 2-chloroethanol tosylate. The reaction mixture is stirred at 70 ° C. for 19 hours, concentrated after cooling in vacuo and 50 ml of water and 50 ml of dichloromethane are added to the residue. The organic phase is separated off, washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.
Man erhält 12,1 g (95 % der Theorie) 2,4-Dichlor-3-(2-chlor-ethoxy)-benzoesäure- efhylester als Öl.12.1 g (95% of theory) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid efhylester are obtained as an oil.
Log P = 3,76
Stufe 2Log P = 3.76 Level 2
Zu einer Lösung von 10,0 g (33,6 mMol) 2,4-Dichlor-3-(2-chlor-ethoxy)-benzoe- säure-ethylester in 70 ml Ethanol gibt man eine Lösung von 2,2 g (55,0 mMol)To a solution of 10.0 g (33.6 mmol) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid ethyl ester in 70 ml of ethanol is added a solution of 2.2 g (55 , 0 mmol)
Natriumhydroxid in 40 ml Wasser. Man rührt die Reaktionsmischung 90 Minuten bei Raumtemperatur (ca. 20°C) und entfernt das Ethanol weitgehend durch Eindampfen im Vakuum. Der Rückstand wird mit konz. Salzsäure auf pH 1 gestellt und mit Essigsäureethylester extrahiert. Die organische Phase wird abgetrennt, mit gesättigter wässriger Natriumchlorid-Lösung gewaschen, über Natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel unter vermindertem Druck sorgfältig abdestilliert.Sodium hydroxide in 40 ml of water. The reaction mixture is stirred for 90 minutes at room temperature (approx. 20 ° C.) and the ethanol is largely removed by evaporation in vacuo. The residue is concentrated. Hydrochloric acid adjusted to pH 1 and extracted with ethyl acetate. The organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.
Man erhält 9,0 g (99 % der Theorie) 2,4-Dichlor-3-(2-chlor-ethoxy)-benzoesäure als weißen Feststoff.9.0 g (99% of theory) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid are obtained as a white solid.
Log P = 2.31Log P = 2.31
Stufe 3level 3
Eine Lösung von 8,5g (31,5 mMol) 2,4-Dichlor-3-(2-chlor-ethoxy)-benzoesäure in 12 ml Thionylchlorid wird eine Stunde auf 60°C erwärmt. Nach beendeter Gasentwicklung wird das überschüssige Thionylchlorid unter vermindertem Druck entfernt.
Als öligen Rückstand erhält man 9,0 g (99 % der Theorie) 2,4-Dichlor-3-(2-chlor- ethoxy)-benzoesäurechlorid.A solution of 8.5 g (31.5 mmol) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid in 12 ml of thionyl chloride is heated to 60 ° C. for one hour. After the evolution of gas has ended, the excess thionyl chloride is removed under reduced pressure. 9.0 g (99% of theory) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid chloride are obtained as an oily residue.
Stufe 4Level 4
Zu einer Lösung von 3,5 g (31,3 mMol) l-Ethyl-5-hydroxy-lH-pyrazol in 200 ml Dichlormethan gibt man nacheinander 9,5 g (94 mMol) Triethylamin, 9 g (31,3 mMol) 2,4-Dichlor-3-(2-chlor-ethoxy)-benzoesäurechlorid und 5 Tropfen N,N-9.5 g (94 mmol) of triethylamine, 9 g (31.3 mmol) are added in succession to a solution of 3.5 g (31.3 mmol) of l-ethyl-5-hydroxy-1H-pyrazole in 200 ml of dichloromethane. 2,4-dichloro-3- (2-chloroethoxy) benzoic acid chloride and 5 drops of N, N-
Dimethyl-formamid. Man rührt die Reaktionsmischung 21 Stunden bei Raumtemperatur (ca. 20°C), wäscht danach mit 2N-Salzsäure und gesättigter wässriger Natriumchlorid-Lösung, trocknet über Natriumsulfat und filtriert. Vom Filtrat entfernt man das Lösungsmittel unter vermindertem Druck.Dimethyl formamide. The reaction mixture is stirred for 21 hours at room temperature (about 20 ° C.), then washed with 2N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is removed from the filtrate under reduced pressure.
Der ölige Rückstand wird in 200 ml Acetonitril gelöst, mit 17g (168 mMol) Triethylamin und 3,26 g (38 mMol) 2-Hydroxy-2-methyl-propionitril versetzt und weitere 20 Stunden bei Raumtemperatur gerührt. Das Lösungsmittel wird dann weitgehend unter vermindertem Druck entfernt und der ölige Rückstand in 100 ml Dichlor- methan aufgenommen. Die organische Phase wird mit 2N-Salzsäure und mit gesättigter wässriger Natriumchlorid-Lösung gewaschen, über Natriumsulfat getrocknet und filtriert. Das Filtrat wird unter vermindertem Druck vom Lösungsmittel befreit.The oily residue is dissolved in 200 ml of acetonitrile, 17 g (168 mmol) of triethylamine and 3.26 g (38 mmol) of 2-hydroxy-2-methyl-propionitrile are added, and the mixture is stirred at room temperature for a further 20 hours. The solvent is then largely removed under reduced pressure and the oily residue is taken up in 100 ml of dichloromethane. The organic phase is washed with 2N hydrochloric acid and with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The filtrate is freed from the solvent under reduced pressure.
Man erhält 11,1 g (98 % der Theorie) [2,4-Dichlor-3-(2-chlor-ethoxy)-phenyl]-(l- ethyl-5-hydroxy-lH-pyrazol-4-yl)-methanon als orangegelben, kristallinen Feststoff.11.1 g (98% of theory) [2,4-dichloro-3- (2-chloroethoxy) phenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) - methanone as an orange-yellow, crystalline solid.
Log P = 2,73.
Stufe 5Log P = 2.73. Level 5
Eine Lösung von 8,0 g (22 mMol) [2,4-Dichlor-3-(2-chlor-ethoxy)-phenyl]-(l-ethyl- 5-hydroxy-lH-pyrazol-4-yl)-methanon in 150 ml Tetrahydrofuran und 200 mlA solution of 8.0 g (22 mmol) of [2,4-dichloro-3- (2-chloroethoxy) phenyl] - (l-ethyl-5-hydroxy-1H-pyrazol-4-yl) methanone in 150 ml of tetrahydrofuran and 200 ml
Ammoniak wird in einem Autoklaven 6.5 Stunden auf 90°C erwärmt. Das überschüssige Ammoniak wird weitgehend abgedampft, das sich abscheidende Produkt durch Filtration abgetrennt und unter vermindertem Druck getrocknet.Ammonia is heated to 90 ° C in an autoclave for 6.5 hours. The excess ammonia is largely evaporated, the product which separates is separated off by filtration and dried under reduced pressure.
Man erhält 4,3 g (57 % der Theorie) [3-(2-Amino-ethoxy)-2,4-dichlor-phenyl]-(l- ethyl-5-hydroxy-lH-pyrazol-4-yl)-methanon als hellgelben, kristallinen Feststoff.4.3 g (57% of theory) [3- (2-amino-ethoxy) -2,4-dichlorophenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) - methanone as a light yellow, crystalline solid.
Log P = 0,72.Log P = 0.72.
Analog zu Beispiel (II- 1) können beispielsweise auch die in der nachstehendenAnalogous to example (II-1), for example, those in the following can also
Tabelle 3 aufgeführten Verbindungen der allgemeinen Formel (II) hergestellt werden.Compounds of general formula (II) listed in Table 3 can be prepared.
Tabelle 3: Beispiele für die Verbindungen der Formel (II) Table 3: Examples of the compounds of the formula (II)
Ausgangsstoffe der Formel (IV): Beispiel (IV-1) Starting materials of the formula (IV): Example (IV-1)
Stufe 1step 1
In 60 ml Acetonitril werden bei Raumtemperatur (ca. 20°C) 15 g (59 mMol) 2,4- Dichlor-3-brommethyl-benzoesäure-methylester und danach 7.5 g (77 mMol)15 g (59 mmol) of 2,4-dichloro-3-bromomethyl-benzoic acid methyl ester and then 7.5 g (77 mmol) are in 60 ml of acetonitrile at room temperature (approx. 20 ° C)
Kaliumthiocyanat eingetragen. Nach langsamem Erhitzen zum Rückfluss wird die Reaktionsmischung 20 Stunden bei dieser Temperatur unter Rückfluss gerührt. Nach dem Abkühlen auf Raumtemperatur wird das Lösungsmittel im Vakuum abgezogen und der Rückstand mit 70 ml Diethylether verrührt. Man saugt vom Ungelösten ab, entfernt das Lösungsmittel im Vakuum und destilliert unter vermindertem Druck.Potassium thiocyanate entered. After slowly heating to reflux, the reaction mixture is stirred at this temperature under reflux for 20 hours. After cooling to room temperature, the solvent is removed in vacuo and the residue is stirred with 70 ml of diethyl ether. The undissolved material is filtered off with suction, the solvent is removed in vacuo and the residue is distilled under reduced pressure.
Man erhält 2.7 g (17 % der Theorie) 2,4-Dichlor-3-isocyanatomethyl-benzoesäure- methylester als Öl, das ohne weitere Reinigung weiter umgesetzt wird.2.7 g (17% of theory) of 2,4-dichloro-3-isocyanatomethyl-benzoic acid methyl ester are obtained as an oil, which is reacted further without further purification.
Stufe 2Level 2
5.6 g roher 2,4-Dichlor-3-isocyanatomethyl-benzoesäure-methylester werden in 20 ml Ethanol gelöst und mit 1.2 g (20 mMol) 2-Propanamin versetzt. Man erhitzt die Mischung eine Stunde zum Sieden, engt die Lösungsmittelmenge auf ein Drittel ein und saugt ab. 5.6 g of crude 2,4-dichloro-3-isocyanatomethyl-benzoic acid methyl ester are dissolved in 20 ml of ethanol and 1.2 g (20 mmol) of 2-propanamine are added. The mixture is heated to boiling for one hour, the amount of solvent is concentrated to a third and suction filtered.
Man erhält 1.7 g (9 % bezogen auf 2,4-Dichlor-3-methyl-benzoesäure-methylester) 2,4-Dichlor-3-[[[(isopropylamino)-thioxomethyl]-amino]-methyl]-benzoesäure- methylester als Feststoff (MS: M+ = 355, 2 CI nach Isotopenmuster).1.7 g (9% based on 2,4-dichloro-3-methyl-benzoic acid methyl ester) of 2,4-dichloro-3 - [[[((isopropylamino) thioxomethyl] amino] methyl] benzoic acid methyl ester are obtained as a solid (MS: M + = 355, 2 CI according to the isotope pattern).
Stufe 3level 3
5 g (15 mMol) N-(3-Methoxycarbonyl-2,6-dichlor-benzyl)-N'-isopropyl-thioharn- stoff werden in 30 ml Methanol gelöst und mit 10 ml (50 mMol) einer 30%igen Lösung von Natriummethanolat in Methanol versetzt. Im Verlauf von 30 Minuten werden 50 ml Wasser zugetropft, worauf man die Mischung 2 Stunden bei 60°C hält. Nach Neutralisation mit 2N-Salzsäure wird abgesaugt und getrocknet.5 g (15 mmol) of N- (3-methoxycarbonyl-2,6-dichlorobenzyl) -N'-isopropyl-thiourea are dissolved in 30 ml of methanol and 10 ml (50 mmol) of a 30% solution of Sodium methanolate added in methanol. 50 ml of water are added dropwise in the course of 30 minutes, after which the mixture is kept at 60 ° C. for 2 hours. After neutralization with 2N hydrochloric acid, the product is filtered off with suction and dried.
Man erhält 4,4 g (91 % der Theorie) 2,4-Dichlor-3-[[[(isopropylamino)-thioxo- methyl]-amino]-methyl]-benzoesäure als Feststoff vom Schmelzpunkt >220°C.4.4 g (91% of theory) of 2,4-dichloro-3 - [[[(isopropylamino) thioxomethyl] amino] methyl] benzoic acid are obtained as a solid with a melting point of> 220 ° C.
Analog zu Beispiel (IV-l) können beispielsweise auch die in der nachstehenden Tabelle 4 aufgeführten Verbindungen der allgemeinen Formel (TVa) hergestellt werden.
Analogously to Example (IV-1), for example the compounds of the general formula (TVa) listed in Table 4 below can also be prepared.
Tabelle 4: Beispiele für die Verbindungen der Formel (IVa)Table 4: Examples of the compounds of the formula (IVa)
Anwendungsbeispieleapplications
Beispiel AExample A
Pre-emergence-TestPre-emergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Samen der Testpflanzen werden in normalen Boden ausgesät. Nach 24 Stunden wird der Boden so mit der Wirkstoffzubereitung besprüht, dass die jeweils gewünschte Wirkstoffmenge pro Flächeneinheit ausgebracht wird. Die Wirkstoffkonzentration in der Spritzbrühe wird so gewählt, daß in 1000 Liter Wasser pro Hektar die jeweils gewünschte Wirkstoff menge ausgebracht wird.Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. Es bedeuten:After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
In diesem Test zeigen beispielsweise die Verbindungen gemäß Herstellungsbeispiel (1-2-1), (1-2-3), (1-2-5) und (1-2-6) bei zum Teil guter Verträglichkeit gegenüber Kulturpflanzen, wie z.B. Mais, Soja und Weizen, starke Wirkung gegen Unkräuter.
Beispiel BIn this test, for example, the compounds according to preparation example (1-2-1), (1-2-3), (1-2-5) and (1-2-6) show with good tolerance to crop plants, such as Corn, soybeans and wheat, strong weed control. Example B
Post-emergence-TestPost-emergence test
Lösungsmittel: 5 Gewichtsteile AcetonSolvent: 5 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschteTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level
Konzentration.Concentration.
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von 5 - 15 cm haben so, daß die jeweils gewünschten Wirkstoffmengen pro Flächeneinheit ausgebracht werden. Die Konzentration der Spritzbrühe wird so gewählt, dass inTest plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray liquor is chosen so that in
1000 1 Wasser/ha die jeweils gewünschten Wirkstoffmengen ausgebracht werden.1000 1 water / ha the desired amounts of active ingredient are applied.
Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle.After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
Es bedeuten:It means:
0 % = keine Wirkung (wie unbehandelte Kontrolle) 100 % = totale Vernichtung0% = no effect (like untreated control) 100% = total destruction
In diesem Test zeigen beispielsweise die Verbindungen gemäß Herstellungsbeispiel (1-2-1), (1-2-3), (1-2-4), (1-2-5), (1-2-6), (1-2-7) und (1-2-8) bei zum Teil guter Verträglichkeit gegenüber Kulturpflanzen, wie z.B. Mais, Raps und Weizen, starke Wirkung gegen Unkräuter.
In this test, the compounds according to Preparation Example (1-2-1), (1-2-3), (1-2-4), (1-2-5), (1-2-6), ( 1-2-7) and (1-2-8) with good tolerance to crops, such as Corn, rapeseed and wheat, strong weed control.
Claims
PatentansprtichePatentansprtiche
1. Verbindungen der Formel (I)1. Compounds of formula (I)
in welcher in which
A1 für eine Einfachbindung oder für O, S, SO, SO2 steht,A 1 represents a single bond or O, S, SO, SO 2 ,
L 2 für Alkandiyl (Alkylen), Alkendiyl oder Alkindiyl steht, L 2 represents alkanediyl (alkylene), alkenediyl or alkindiyl,
für O (Sauerstoff) oder S (Schwefel) steht,represents O (oxygen) or S (sulfur),
R1 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aryl oder Arylalkyl, oder für die Gruppierung -C(Q)-R2 steht,R 1 stands for hydrogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or for the grouping -C (Q) -R 2 ,
R2 für Wasserstoff, Amino, Cyanoamino, Nitroamino, Hydroxyamino, Hydrazino, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylamino, Dialkylamino, Alkoxyamino, N-Alkyl-alkoxyamino, Alkylhydrazino, Dialkylhydrazino, Alkenyl, Alkenyloxy, Alkenylamino, Alkenyloxy- amino, Alkinyl, Alkinyloxy, Alkinylamino, Cycloalkyl, Cycloalkyl- oxy, Cycloalkylamino, Cycloalkylalkyl, Cycloalkylalkoxy, Cyclo- alkylalkylamino, Aryl, Arylcarbonyl, Aryloxy, Aryloxycarbonyl, Arylthio, Arylamino, Arylhydrazino, Arylalkyl, Arylalkoxy, Aryl-
alkylthio, Arylalkylamino, Heterocyclyl, Heterocyclyloxy, Hetero- cyclylthio, Heterocyclylamino, Heterocyclylalkyl, Heterocyclyl- alkoxy, Heterocyclylalkylthio oder Heterocyclylalkylamino steht,R 2 for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, dialkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, alkenyl, alkenyloxy, Alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazylalkoxy, arylalkyl, alkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,
X für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Dialkylaminosulfonyl steht,X stands for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
Y für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Dialkylaminosulfonyl steht, undY stands for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and
für eine der nachstehenden Gruppierungen stehtrepresents one of the groupings below
wobeiin which
m für die Zahlen 0 bis 6 steht,m represents the numbers 0 to 6,
R für Wasserstoff, Halogen oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylthio oder Aryl steht, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff oder Alkandiyl (Alkylen) steht,
R4 für Hydroxy, Formyloxy, Halogen, oder für jeweils gegebenenfalls substituiertes Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylamino- carbonyloxy, Alkylsulfonyloxy, Alkenyloxy, Alkinyloxy, Aryloxy, Arylthio, Arylsulfϊnyl, Arylsulfonyl, Arylcarbonyl- oxy, Arylcarbonylalkoxy, Arylsulfonyloxy, Arylalkoxy, Aryl- alkylthio, Arylalkylsulfinyl oder Arylalkylsulfonyl steht,R stands for hydrogen, halogen or for optionally substituted alkyl, alkylthio or aryl, or - if m stands for 2 - optionally also together with a second radical R 3 stands for oxygen or alkanediyl (alkylene), R 4 is hydroxy, formyloxy, halogen, or represents in each case optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, Arylsulfϊnyl, arylsulfonyl, arylcarbonyl oxy, Arylcarbonylalkoxy, Arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl,
R5 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy,R 5 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy,
Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkoxycarbonyl oder Cycloalkyl steht,Alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
R6 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aryl oder Arylalkyl steht,R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R7 für Hydroxy, Formyloxy, oder für jeweils gegebenenfalls substituiertes Alkoxy, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyloxy, Alkylsulfonyloxy, Alkenyloxy,R 7 for hydroxy, formyloxy, or for each optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy,
Alkinyloxy, Arylalkoxy, Arylcarbonyloxy, Arylcarbonylalkoxy oder Arylsulfonyloxy steht,Alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
R8 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl steht,R 8 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
R9 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht,
R10 für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl oder Cycloalkyl steht, undR 9 represents hydrogen or represents optionally substituted alkyl or cycloalkyl, R 10 represents hydrogen or represents optionally substituted alkyl or cycloalkyl, and
R11 für Wasserstoff, Cyano, Carbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl steht.R 11 represents hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl.
2. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass2. Compounds of formula (I) according to claim 1, characterized in that
A1 für O oder für eine Einfachbindung steht,A 1 represents O or a single bond,
A2 für Alkandiyl (Alkylen), Alkendiyl oder Alkindiyl mit jeweils bis zu 6 Kohlenstoffatomen steht,A 2 represents alkanediyl (alkylene), alkenediyl or alkindiyl each having up to 6 carbon atoms,
Q für O (Sauerstoff) steht,Q stands for O (oxygen),
R1 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Halogen, C\- C4-Alkoxy, Cι-C4-Al ylthio, -C4- Alkylsulfinyl oder d-C4-Alkyl- sulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl oder Alkylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für Dialkylamino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 2 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder C1-C4-Alkyl substituiertes Cycloalkyl oder Cycloalkylalkyl mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C4-Alkyl, d-C -Halogen- alkyl, C1-C -Alkoxy oder C1-C -Halogenalkoxy substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Aryl-
gruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für die Gruppierung -C(Q)-R2 steht,R 1 represents hydrogen, represents in each case optionally cyano-, halogen-, C \ - C 4 -alkoxy, C 4 -alkyl ylthio, -C 4 - alkylsulfinyl or C 4 alkyl sulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, Alkylsulfonyl or alkylamino, each with 1 to 6 carbon atoms in the alkyl groups, for dialkylamino, each with 1 to 4 carbon atoms in the alkyl groups, for alkenyl or alkynyl, each optionally substituted by cyano or halogen, with 2 to 6 carbon atoms each, each optionally substituted by cyano, halogen or C 1 -C 4 alkyl-substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for in each case optionally by nitro, cyano, halogen, dC 4 -alkyl, dC -haloalkyl , C 1 -C alkoxy or C 1 -C haloalkoxy-substituted aryl or arylalkyl, each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or represents the group -C (Q) -R 2 ,
für Wasserstoff, Amino, Cyanoamino, Nitroamino, Hydroxya ino, Hydrazino, für C1-C4-Alkyl-carbonyl, für C -C -Alkoxy-carbonyl, für jeweils gegebenenfalls durch Cyano, Halogen, d-C -Alkoxy, C]-C - Alkylthio, d-C - Alkylsulfmyl oder d-C - Alkylsulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Alkoxyamino oder Alkylhydrazino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkyl- gruppen, für Dialkylamino, N-Alkyl-alkoxyamino oder Dialkyl- hydrazino mit jeweils 1 bis 4 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl, Alkenyloxy, Alkenylamino, Alkenyloxyamino, Alkinyl, Alkinyloxy oder Alkinylamino mit jeweils 2 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder d-C4-Alkyl substituiertesfor hydrogen, amino, cyanoamino, nitroamino, hydroxya ino, hydrazino, for C 1 -C 4 -alkyl carbonyl, for C -C -alkoxy-carbonyl, for each optionally by cyano, halogen, dC -alkoxy, C] -C - Alkylthio, dC - alkylsulfmyl or dC - alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxyamino or alkylhydrazino, each with 1 to 6 carbon atoms in the alkyl groups, for dialkylamino, N-alkylalkoxyamino or dialkylhydrazino, each with 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino, each optionally substituted by halogen, each having 2 to 6 carbon atoms, each optionally substituted by cyano, halogen or dC 4 -alkyl
Cycloalkyl, Cycloalkyloxy, Cycloalkylamino, Cycloalkylalkyl, Cyclo- alkylalkoxy oder Cycloalkylalkylamino mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C4-Alkyl, d-C4-Halogenalkyl, d-C -Cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino, each with 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, dC 4 alkyl, dC 4 haloalkyl , dC -
Alkoxy, d-C4-Halogenalkoxy oder C1-C4-Alkoxy-carbonyl substituiertes Aryl, Arylcarbonyl, Aryloxy, Aryloxycarbonyl, Arylthio, Aryl- amino, Arylhydrazino, Arylalkyl, Arylalkoxy, Arylalkylthio oder Arylalkylamino mit jeweils 6 oder 10 Kohlenstoffatomen in der Aryl- gruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C - Alkyl, Cι-C -Halogenalkyl, d-C -Alkoxy, d-C4-Halogenalkoxy, d- C -Alkylthio, d-C4-Halogenalkylfhio oder d-Q-Alkoxy-carbonyl substituiertes monocyclisches oder bicyclisches Heterocyclyl, Hetero- cyclyloxy, Heterocyclylthio, Heterocyclylarnino, Heterocyclylalkyl,Alkoxy, dC 4 -haloalkoxy or C 1 -C 4 -alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen, dC - alkyl, -C-C -haloalkyl, dC -alkoxy, dC 4 -haloalkoxy, d- C -alkylthio, dC 4 -haloalkylfhio or dQ-alkoxy-carbonyl substituted monocyclic or bicyclic heterocyclyl, heterocyclicoxy, heterocyclylthio, heterocyclylarnino, heterocyclylalkyl,
Heterocyclylalkoxy, Heterocyclylalkylthio oder Heterocyclylalkyl-
amino steht, wobei jeweils die Heterocyclyl-Gruppierung bis zu 10 Kohlenstoffatome und zusätzlich mindestens ein Heteroatom ausgewählt aus der Reihe Stickstoff (N) (höchstens jedoch 5 N- Atome), Sauerstoff (O) (höchstens jedoch 2 O-Atome), Schwefel (S) (höchstens jedoch 2 S-Atome), SO oder SO2 sowie gegebenenfalls zusätzlich eine Gruppe ausgewählt aus Oxo (C=O), Thioxo (C=S), Imino (C=NH), Cyanoimino (C=N-CN), Nitroimino (C=N-NO2) enthält,Heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkyl- amino, where in each case the heterocyclyl grouping has up to 10 carbon atoms and additionally at least one heteroatom selected from the series nitrogen (N) (but not more than 5 N atoms), oxygen (O) (but not more than 2 O atoms), sulfur ( S) (but at most 2 S atoms), SO or SO 2 and, if appropriate, additionally a group selected from oxo (C = O), thioxo (C = S), imino (C = NH), cyanoimino (C = N-CN) ), Contains nitroimino (C = N-NO 2 ),
X für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen, Ci-X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen, Ci
C4-Alkoxy, CrC4-Alkylthio, CrC4- Alkylsulfinyl oder C1-C4-Alkyl- sulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino oder Dialkylaminosulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,C 4 alkoxy, C r C 4 alkylthio, C r C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms is in the alkyl groups,
Y für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl,Y for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,
Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen, d-Halogen, or for each optionally by cyano, halogen, d-
C4-Alkoxy, CrC4-Alkylthio, CrC4-Alkylsulfmyl oder CrC4-Alkyl- sulfonyl substituiertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkyl- sulfonyl, Alkylamino, Dialkylamino oder Dialkylaminosulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,C 4 alkoxy, C r C 4 alkylthio, C r C 4 alkylsulfmyl or C r C 4 alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, each with 1 to 6 Carbon atoms in the alkyl groups,
Z für eine der nachstehenden Gruppierungen steht,Z represents one of the groupings below,
m für die Zahlen 0 bis 3 steht,
R3 für Wasserstoff, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, C C4-Alkoxy, d-C -Alkylthio, d-C4- Alkylsulfinyl oder C1-C4- Alkylsulfonyl substituiertes Alkyl oder Alkylthio mit jeweils 1 bis 6 Kohlenstoffatomen, oder für Phenyl, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Restm represents the numbers 0 to 3, R 3 represents hydrogen, halogen, in each case optionally substituted by cyano, halogen, CC 4 -alkoxy, dC -alkylthio, dC 4 -alkylsulfinyl or C 1 -C 4 -alkylsulfonyl-substituted alkyl or alkylthio each having 1 to 6 carbon atoms, or for phenyl , or - if m stands for 2 - optionally together with a second residue
R3 für Sauerstoff oder Alkandiyl (Alkylen) mit 3 bis 5 Kohlenstoffatomen steht,R 3 represents oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms,
R4 für Hydroxy, Formyloxy, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, Cι-C4-Alkoxy, C1-C - Alkylthio, C1-C4-Alkylsulfinyl oder d-C4-Alkylsulfonyl substituiertes Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyloxy oder Alkylsulfonyloxy mit jeweils 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Halogen sub- stituiertes Alkenyloxy oder Alkinyloxy mit jeweils 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-C4-Alkyl, d-C4-Halogenalkyl, d-C4-Alkoxy, C1-C4-Halogen- alkoxy, C1-C4-Alkylthio, d-C -Halogenalkylfhio, d-C4-Alkyl- sulfinyl, Cι-C4-Halogenalkylsulfmyl, C1-C4- Alkylsulfonyl oder d- C -Halogenalkylsulfonyl substituiertes Aryloxy, Arylthio, Aryl- sulfinyl, Arylsulfonyl, Arylcarbonyloxy, Arylcarbonylalkoxy, Arylsulfonyloxy, Arylalkoxy, Arylalkylthio, Arylalkylsulfinyl oder Aryl- alkylsulfonyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil steht,R 4 is hydroxy, formyloxy, halogen, represents in each case optionally cyano-, halogen, Cι-C 4 alkoxy, C 1 -C - alkylthio, C 1 -C 4 alkylsulfinyl or C 4 alkylsulfonyl substituted alkoxy, alkylthio, alkylsulfinyl, Alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, for each optionally substituted by halogen, alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, each optionally using nitro, cyano, halogen, dC 4 -alkyl, dC 4 -haloalkyl, dC 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, dC -haloalkylfhio, dC 4 -alkylsulfinyl, -C-C 4 -haloalkylsulfmyl, C 1 -C 4 - Alkylsulfonyl or d- C -haloalkylsulfonyl substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl each having 6 or 10 carbon atoms r is aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
R5 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, für jeweils gegebenenfalls durch Cyano, Halogen, d-C4-Alkoxy, C1-C4-R 5 for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, for each optionally by cyano, halogen, dC 4 -alkoxy, C1-C4-
Alkylthio, d-C4-Alkylsulfmyl oder d-Q-Alkylsulfonyl substitu- iertes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl oderAlkylthio, dC 4 -alkylsulfmyl or dQ-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or
Alkoxycarbonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkyl-
gruppen oder für gegebenenfalls durch Cyano, Halogen oder d-C - Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen.Alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or dC-alkyl.
R6 für Wasserstoff, für gegebenenfalls durch Cyano, Halogen, C1-C4- Alkoxy, Cι-C4-Al ylthio, C1-C4- Alkylsulfinyl oder d-C4- Alkylsulfonyl substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyl oder Alkinyl mit jeweils 3 bis 6 Kohlenstoffatomen, für jeweils gegebenenfalls durch Cyano, Halogen oder C1-C4- Alkyl substituiertes Cyclo- alkyl oder Cycloalkylalkyl mit jeweils 3 bis 6 Kohlenstoffatomen in der Cycloalkylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, d-d-Alkyl, C1-C -Halogenalkyl, d-C4-Alkoxy, C1-C - Halogenalkoxy, d-C4-Alkylthio, C1-C4-Halogenalkylthio, d-C4- Alkylsulfinyl, d-C4-Halogenalkylsulfinyl, C1-C4- Alkylsulfonyl oder d-Q-Halogenalkylsulfonyl substituiertes Aryl oder Arylalkyl mit jeweils 6 oder 10 Kohlenstoffatomen in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil steht,R 6 represents hydrogen, represents optionally cyano-, halogen-, C 1 -C 4 - alkoxy, Cι-C 4 -alkyl ylthio, C1-C4 alkylsulfinyl or C 4 - alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally Cyano or halogen substituted alkenyl or alkynyl, each having 3 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C1-C4-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part , or for each optionally by nitro, cyano, halogen, dd-alkyl, C 1 -C -haloalkyl, dC 4 -alkoxy, C 1 -C - haloalkoxy, dC 4 -alkylthio, C 1 -C 4 -haloalkylthio, dC 4 - Alkylsulfinyl, dC 4 -haloalkylsulfinyl, C 1 -C 4 - alkylsulfonyl or dQ-haloalkylsulfonyl-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part s TEHT,
R7 für Hydroxy, Formyloxy, für jeweils gegebenenfalls durch Cyano,R 7 for hydroxy, formyloxy, for each optionally by cyano,
Halogen oder d-C4-Alkoxy substituiertes Alkoxy, Alkylcarbonyloxy, Alkoxycarbonyloxy, Alkylaminocarbonyloxy oder Alkylsulfonyloxy mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen, für jeweils gegebenenfalls durch Cyano oder Halogen substituiertes Alkenyloxy oder Alkinyloxy mit jeweils 3 bis 6 Kohlenstoffatomen, oder für jeweils gegebenenfalls durch Nitro, Cyano, Halogen, C1-C4- Alkyl, d-C4-Halogenalkyl, d-d-Alkoxy, C1-C4-Halogenalkoxy, d- d-Alkylfhio, C1-C4-Halogenalkylthio, d-C -Alkylsulfinyl, C1-C4- Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl oder C1-C4-Halogenalkyl- sulfonyl substituiertes Arylalkoxy, Arylcarbonyloxy, Arylcarbonyl- alkoxy oder Arylsulfonyloxy mit jeweils 6 oder 10 Kohlenstoffatomen
in der Arylgruppe und gegebenenfalls 1 bis 4 Kohlenstoffatomen im Alkylteil steht,Halogen or dC 4 -alkoxy-substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, for alkenyloxy or alkynyloxy each optionally substituted by cyano or halogen, each having 3 to 6 carbon atoms, or for each optionally containing nitro , Cyano, halogen, C1-C4-alkyl, dC 4 -haloalkyl, dd-alkoxy, C 1 -C 4 -haloalkoxy, d- d-alkylfhio, C 1 -C 4 -haloalkylthio, dC -alkylsulfinyl, C1-C4- Haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy each having 6 or 10 carbon atoms is in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
R8 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder d-C4-Alkoxy substituiertes Alkyl, Alkylcarbonyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht,R 8 stands for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups each optionally substituted by cyano, halogen or dC 4 -alkoxy .
R9 für Wasserstoff, für gegebenenfalls durch Cyano, Halogen oder C1-C4-R 9 represents hydrogen, optionally by cyano, halogen or C 1 -C 4 -
Alkoxy substituiertes Alkyl, oder für gegebenenfalls durch Cyano, Halogen oder d-d-Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht,Alkoxy substituted alkyl, or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or d-d-alkyl,
R10 für Wasserstoff, für gegebenenfalls durch Cyano, Halogen oder C1-C4-R 10 for hydrogen, for optionally by cyano, halogen or C 1 -C 4 -
Alkoxy substituiertes Alkyl, oder für gegebenenfalls durch Cyano, Halogen oder d-C4- Alkyl substituiertes Cycloalkyl mit 3 bis 6 Kqh- lenstoffatomen steht, undAlkoxy-substituted alkyl, or cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, halogen or dC 4 -alkyl, and
R11 für Wasserstoff, Cyano, Carbamoyl, Halogen, oder für jeweils gegebenenfalls durch Cyano, Halogen oder Ci-d-Alkoxy substituiertes Alkyl, Alkoxy, Alkoxycarbonyl, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylgruppen steht.R 11 represents hydrogen, cyano, carbamoyl, halogen, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and is optionally substituted by cyano, halogen or Ci-d-alkoxy.
3. Verbindungen der Formel (I) gemäß Ansprch 1, dadurch gekennzeichnet, dass3. Compounds of formula (I) according to claim 1, characterized in that
A2 für Methylen (-CH2-), Ethan-l,l-diyl(-CH(CH3)-), Ethan-l,2-diyl (Di- methylen, -CH2CH2-), Propan-l,l-diyl(-CH(C2H5)-), Propan-l,2-diyl (-CH(CH3)CH2-), Propan-l,3-diyl (-CH2CH2CH2-), Butan-1,3-
diyl(-CH(CH3)CH2CH2-), Butan- 1,4-diyl (-CH2CH2CH2CH2-), Ethen- diyl, Propendiyl, Butendiyl, Ethindiyl, Propindiyl oder Butindiyl steht,A 2 for methylene (-CH 2 -), ethane-l, l-diyl (-CH (CH 3 ) -), ethane-l, 2-diyl (dimethylene, -CH 2 CH 2 -), propane l, l-diyl (-CH (C 2 H 5 ) -), propane-l, 2-diyl (-CH (CH 3 ) CH 2 -), propane-l, 3-diyl (-CH 2 CH 2 CH 2 -), butane-1,3- diyl (-CH (CH 3 ) CH 2 CH 2 -), butane-1,4-diyl (-CH 2 CH 2 CH 2 CH 2 -), ethylenediyl, propendiyl, butenediyl, ethindiyl, propindiyl or butynediyl,
R1 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propyl- sulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methyl- thio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i- , s- oder t-Butylamino, für Dimethylamino oder Diethylamino, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substitu- iertes Ethenyl, Propenyl, Butenyl, Pentenyl, Ethinyl, Propinyl, Butinyl oder Pentinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl oder Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutyl- methyl, Cyclopentylmethyl oder Cyclohexyhnethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl,R 1 for hydrogen, each optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propyl- sulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, each optionally substituted by fluorine, chlorine and / or bromine ized ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl cyclopropyl, cyclobutyl, cyclopentyl, cyc lohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl,
Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl, Naphthyl, Phenylmethyl, Phenylethyl, Naphthylmethyl oder Naphthylethyl oder für Gruppierung -C(Q)-R2 steht,Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl or stands for grouping -C (Q) -R 2 ,
R2 für Wasserstoff, Amino, Cyanoamino, Nitroamino, Hydroxyamino,R 2 for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino,
Hydrazino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor,Hydrazino, for each optionally by cyano, fluorine, chlorine,
Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl,Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl,
Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n-
oder i-Propyl, n-, i-, s- oder t-Butyl, n-, i-, s- oder t-Pentyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Methoxyamino, Ethoxyamino, n- oder i-Propoxyamino, n-, i-, s- oder t-Butoxyamino, Methylhydrazino, Ethylhydrazino, n- oder i-Propyl- hydrazino, n-, i-, s- oder t-Butylhydrazino, für Dimethylamino, Diethylammo, N-Methyl-methoxyamino, Dimethylhydrazino oder Di- ethylhydrazino, für jeweils gegebenenfalls durch Fluor, Chlor und/oder Brom substituiertes Ethenyl, Propenyl, Butenyl, Pentenyl,Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t -Butylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t -Butylhydrazino, for dimethylamino, diethylammo, N-methyl-methoxyamino, dimethylhydrazino or diethylhydrazino, for ethenyl, propenyl, butenyl, pentenyl optionally substituted by fluorine, chlorine and / or bromine,
Ethinyl, Propinyl, Butinyl, Pentinyl, Propenyloxy, Butenyloxy, Pente- nyloxy, Propenylthio, Butenylthio, Pentenylthio, Propenylamino, Butenylamino, Pentenylamino, Propenyloxyamino, Butenyloxyamino, Pentenyloxyamino, Ethinyl, Propinyl, Butinyl, Pentinyl, Propinyloxy, Butinyloxy, Pentinyloxy, Propinylamino, Butinylamino oder Pentinyl- amino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Brom, Methyl, Ethyl oder Propyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopen- tyloxy, Cyclohexyloxy, Cyclopropylamino, Cyclobutylamino, Cyclo- pentylamino, Cyclohexylamino, Cyclopropylmethyl, Cyclobutyl- methyl, Cyclopentylmethyl, Cyclohexyhnethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopropylmethylamino, Cyclobutylmethylamino, Cyclopentyl- methylamino oder Cyclohexylmethylamino, für jeweils gegebenen- falls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethynyl, propynyl, propynyl, pentynyloxy, pentyloxyamino Butynylamino or pentynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl cyclohexylamino, cyclopropylmethyl, cyclobutyl methyl, cyclopentylmethyl, Cyclohexyhnethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, Cyclobutylmethylamino, cyclopentyl methylamino or cyclohexylmethylamino, represents in each case gegebenen- substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl n- or i-
Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes Phenyl, Phenylcarbonyl, Phenoxy, Phenoxycarbonyl, Phenylthio, Phenyl- amino, Phenylhydrazino, Naphthyl, Naphthyloxy, Naphtylthio,Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl , Phenylthio, phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio,
Naphthylamino, Phenylmethyl, Phenylethyl, Phenylmethoxy, Phenyl-
ethoxy, Phenylmethylthio, Phenylethylthio, Phenylmethylamino, Phenylethylamino, Naphthylmethyl, Naphthylethyl, Naphthyl- methoxy, Naphthylethoxy, Naphthylmethylamino oder Naphthylethyl- amino, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl,Naphthylamino, phenylmethyl, phenylethyl, phenylmethoxy, phenyl ethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy, naphthylmethylamino or naphthylethylamino, or for each optionally by nitro, cyano, fluorine, chlorine, bromine or methyl, ethyl, n Propyl, n-, i-, s- or t-butyl,
Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Chlor- difluormethyl, Fluordichlormethyl, Methoxy, Ethoxy, n- oder i- Propoxy, n-, i-, s- oder t-Butoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Difluormethylthio, Trifluormethylfhio, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes monocyclisches oder bicyclisches Heterocyclyl, Heterocyclyloxy, Heterocyclylamino, Heterocyclylalkyl, Heterocyclylalkoxy oder Heterocyclylalkylamino aus der Reihe Furyl, Furyloxy, Furyla ino, Furylmethyl, Furyl- methoxy, Furylmethylamino, Thienyl, Thienylmethyl, Pyrrolidinyl,Difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i -Propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylfhio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclycyllalkyl, heterocyclyl alkylyl heterocyllyl heterocyllyl heterocyllyl heterocylcylamino heterocylcylcyloxyalkyl Furyloxy, furyla ino, furylmethyl, furylmethoxy, furylmethylamino, thienyl, thienylmethyl, pyrrolidinyl,
Pyrrolidinylamino, Oxopyrrolidinyl, Pyrrolyl, Indolyl, Pyrrolylmethyl, Pyrazolyl, Pyrazolyloxy, Pyrazolylamino, Pyrazolylmethyl, Imid- azolyl, Imidazolylmethyl, 2-Oxo-l,3-diaza-cyclopentyl, Oxazolyl, Dihydrooxazolyl (Oxazolinyl), Isoxazolyl, Dihydroisoxazolyl (Isoxazolinyl), Tetrahydroisoxazolyl (Isoxazohdinyl), Oxazolylmethyl, Thiazolyl, Dihydrothiazolyl (Thiazolinyl), Tetrahydro- thiazolyl (Thiazolidinyl), Thiazolylmethyl, Thiazolidinyl, Oxothi- azolidinyl, Cyanoiminothiazolidinyl, Oxotriazolinyl, Oxotetrazolinyl, Piperidinyl, Piperidinylamino, Oxopiperidinyl, 2-Oxo-l,3-diaza- cyclohexyl, 2-Oxo-l-aza-cycloheptyl, 2-Oxo-l,3-diaza-cycloheptyl,Pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolylmethyl, 2-oxo-l, 3-diaza-cyclopentyl, oxazolyl, dihydrooxoloxololyl (dihydrooxoloxololyl) (oxazolyl) dihydrooxololazolyl (dihydrooxoloxololyl) dihydrooxoloxolylyl Tetrahydroisoxazolyl (Isoxazohdinyl), oxazolylmethyl, thiazolyl, dihydrothiazolyl (thiazolinyl), tetrahydro- thiazolyl (thiazolidinyl), thiazolylmethyl, thiazolidinyl, Oxothi- azolidinyl, Cyanoiminothiazolidinyl, Oxotriazolinyl, Oxotetrazolinyl, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-l, 3-diaza cyclohexyl, 2-oxo-l-aza-cycloheptyl, 2-oxo-l, 3-diaza-cycloheptyl,
Morpholinyl, Morpholinylamino, Piperazinyl, Pyridinyl, Pyridinyloxy, Pyridinylamino, Pyridinylmefhyl, Pyridinylmethoxy, Pyri- midinyl, Pyrimidinyloxy, Pyrimidinylmethyl, Pyrimidinylmethoxy steht,
X für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl,Morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmefhyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl, pyrimidinylmethoxy, X for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl,
Fluor, Chlor, Brom, Iod, oder für jeweils gegebenenfalls durch Cyano,Fluorine, chlorine, bromine, iodine, or for each optionally by cyano,
Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl,Fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl,
Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy,Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,
Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methylamino, Ethylamino, n- oder i-Propyl- amino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino,Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,
Dimethylaminosulfonyl oder Diethylaminosulfonyl steht,Dimethylaminosulfonyl or diethylaminosulfonyl,
Y für Wasserstoff, Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl,Y for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl,
Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Dimethylamino, Diethylamino, Dimethylaminosulfonyl oder Diethylaminosulfonyl steht,Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl,
m für die Zahlen 0, 1 oder 2 steht,m represents the numbers 0, 1 or 2,
R3 für Fluor, Chlor oder Brom, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulf- onyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methylthio, Ethylthio, n- oder i-Propylfhio, n-, i-
, s- oder t-Butylthio, oder für Phenyl, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff, Propan-l,3-diyl oder Butan- 1,4-diyl steht,R 3 for fluorine, chlorine or bromine, each optionally with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylfhio, n-, i- , s- or t-butylthio, or for phenyl, or - if m is 2 - optionally together with a second radical R 3 for oxygen, propane-l, 3-diyl or butane-1,4- diyl stands,
R4 für Hydroxy, Formyloxy, Fluor oder Chlor, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propyl- thio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl,R 4 for hydroxyl, formyloxy, fluorine or chlorine, each optionally with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl,
Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methyl- aminocarbonyloxy, Ethylaminocarbonyloxy, n- oder i-Propylamino- carbonyloxy, Methylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propyl- sulfonyloxy, für jeweils gegebenenfalls durch Fluor, Chlor und/oderAcetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propyl for each optionally by fluorine, chlorine and / or
Brom substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluor- methylthio, Trifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Tri- fluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Trifiuor- methylsulfonyl substituiertes Phenyloxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Phenylcarbonyloxy, Phenylcarbonylalkoxy, Phenyl- sulfonyloxy, Phenylmethoxy, Phenylmethylthio, Phenylmethylsulfmyl oder Phenylmethylsulfonyl steht,Bromine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl or ethylsulfonyl- Phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylalkoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfmyl or phenylmethylsulfonyl,
R5 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor oderR 5 for hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or
Brom, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Bromine, each optionally with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-
Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethyl-
sulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxy- carbonyl, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor,Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for each optionally by cyano, fluorine, chlorine,
Methyl oder Ethyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht,Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R6 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-R 6 for hydrogen, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-
Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Brom substituiertes Propenyl, Butenyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmefhyl, Cyclopentylmethyl oder Cyclohexyhnethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, n-, i-, s- oder t-Butylthio, Difluormethylthio, Trifluormethyl- thio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfmyl, Methylsulfonyl, Ethylsulfonyl oder Trifluormethylsulfonyl substituiertes Phenyl oder Phenylmethyl steht,Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl optionally substituted by cyano, fluorine, chlorine or bromine, Propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmefhyl, cyclopentylmethyl or cyclohexylethyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfmyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl or phenylmethyl,
R7 für Hydroxy, Formyloxy, für jeweils gegebenenfalls durch Cyano,R 7 for hydroxy, formyloxy, for each optionally by cyano,
Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertesFluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted
Methoxy, Ethoxy, n- oder i-Propoxy, Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylamino-
carbonyloxy, n- oder i-Propylaminocarbonyloxy, Methylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Brom substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, oder für jeweils gege- benenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio, Methylsulfinyl, Ethylsulfinyl, Trifluormethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Trifluormethylsulfonyl substituiertes Phenyl- methoxy, Phenylcarbonyloxy, Phenylcarbonyl ethoxy oder Phenyl- sulfonyloxy steht,Methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino carbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, optionally substituted by cyano, fluorine, chlorine or bromine, or, if appropriate, by nitro, cyano , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonyl ethoxy or phenyl- sulfoxy,
R8 für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl, Fluor, Chlor oder Brom, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor,R 8 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or for each optionally by cyano, fluorine, chlorine,
Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Acetyl, Propionyl, n- oder i- Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oderMethoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or
Ethylsulfonyl steht,Ethylsulfonyl stands,
R9 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor,R 9 for hydrogen, for each optionally by cyano, fluorine, chlorine,
Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht,Methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R10 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, oder für jeweils gegebenenfalls
durch Cyano, Fluor, Chlor, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht, undR 10 is hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or for each if necessary cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by cyano, fluorine, chlorine, methyl or ethyl, and
R11 für Wasserstoff, Cyano, Carbamoyl, Fluor, Chlor oder Brom, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulf- onyl oder Ethylsulfonyl steht.R 11 is hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or is methyl, ethyl, n- or i-propyl, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. , i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfo- onyl or ethylsulfonyl.
4. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass4. Compounds of formula (I) according to claim 1, characterized in that
A2 für Methylen (-CH2-), Ethan-l,2-diyl (Dimethylen, -CH2CH2-) oderA 2 for methylene (-CH 2 -), ethane-l, 2-diyl (dimethylene, -CH 2 CH 2 -) or
Propan-l,3-diyl (-CH2CH2CH2-) steht,Propane-1,3-diyl (-CH 2 CH 2 CH 2 -),
R1 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethyl- sulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl,R 1 for hydrogen, for each methyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
Ethyl, n- oder i-Propyl, n- oder i-Butyl, für Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylamino, Ethylamino, n- oder i-Propylamino, für Dimethylamino, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyl, Butenyl, Ethinyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclo- butyhnethyl, Cyclopentylmethyl oder Cyclohexyhnethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl,Ethyl, n- or i-propyl, n- or i-butyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, for dimethylamino, for propenyl, butenyl, ethynyl, propynyl or butynyl optionally substituted by fluorine and / or chlorine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl each optionally substituted by cyano, fluorine, chlorine or methyl or cyclohexylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,
Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluor-
methoxy substituiertes Phenyl, Phenylmethyl oder Phenylethyl, oder für die Gruppierung -C(Q)-R2 steht,Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoro- methoxy substituted phenyl, phenylmethyl or phenylethyl, or represents the group -C (Q) -R 2 ,
für Wasserstoff, Amino, Hydroxyamino, Hydrazino, für jeweils gege- benenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-for hydrogen, amino, hydroxyamino, hydrazino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-
Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propyl- thio, Methylamino, Ethylamino, n- oder i-Propylamino, Methoxyamino, Ethoxyamino, n- oder i-Propoxyamino, für Dimethylamino, für N-Methyl-methoxy amino, für Dimethylhydrazino, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Ethenyl, Propenyl, Butenyl, Propenyloxy, Butenyloxy, Propenylthio, Butenyl- thio, Propenylamino, Butenylamino, Ethinyl, Propinyl, Butinyl,Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n - or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, for dimethylamino, for N-methyl-methoxy amino, for dimethylhydrazino, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl, each optionally substituted by fluorine and / or chlorine,
Propinyloxy, Butinyloxy, Propinylamino oder Butinylamino, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl oder Cyclo- hexylmethyl, für jeweils gegebenenfalls durch Nitro, Cyano, Fluor,Propynyloxy, butynyloxy, propynylamino or butynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine or methyl, each optionally substituted by nitro, cyano, fluorine,
Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Trifluormethoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i- Propoxycarbonyl substituiertes Phenyl, Phenylamino, Phenylmethyl oder Phenylethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano,Chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n - or i- propoxycarbonyl substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano,
Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Chlordifluormethyl, Fluordichlormethyl, Methoxy, Ethoxy, n- oder i- Propoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Difluormethylthio, Trifluormethylthio, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl substituiertes
monocyclisches oder bicyclisches Heterocyclyl oder Heterocyclylalkyl aus der Reihe Furyl, Furylmethyl, Thienyl, Thienylmethyl, Pyrrolidinyl, Oxopyrrolidinyl, Pyrrolyl, Pyrrolylmethyl, Pyrazolyl, Pyrazolylmethyl, Imidazolyl, Imidazolylmethyl, 2-Oxo-l,3-diaza- cyclopentyl, Oxazolyl, Isoxazolyl, Oxazolylmethyl, Isoxazohdinyl,Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i - Propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, furylmethyl, thienyl, thienylmethyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl, imidazolylmethyl, 2-oxo-oxo-loxyl , Isoxazohdinyl,
Thiazolyl, Thiazolylmethyl, Piperidinyl, Oxopiperidinyl, 2-Oxo-l,3- diazacyclohexyl, Morpholinyl, Piperazinyl, Pyridinyl, Pyridinyl- methyl, Pyrimidinyl, Pyrimidinylmethyl steht,Thiazolyl, thiazolylmethyl, piperidinyl, oxopiperidinyl, 2-oxo-1,3-diazacyclohexyl, morpholinyl, piperazinyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl,
X für Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n- oder i-Propyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Tri- chlormethyl, Methoxymethyl, Methylthiomethyl, Methylsulfinyl- methyl, Methylsulfonylmethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl steht,X for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinyl-methyl, methylsulfonylmethyl, methoxy, ethoxy , Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
Y für Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Methoxymethyl, Methylthiomethyl, Methylsulfinylmethyl, Methylsulfonyl- methyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl steht,Y for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylthio, Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
R3 für Wasserstoff, für jeweils gegebenenfalls durch Fluor und/oderR 3 for hydrogen, for each optionally by fluorine and / or
Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, Methylthio,Chlorine substituted methyl, ethyl, n- or i-propyl, methylthio,
Ethylthio, n- oder i-Propylthio, oder für Phenyl, oder - für den Fall, dass m für 2 steht - gegebenenfalls auch zusammen mit einem zweiten Rest R3 für Sauerstoff, Propan-1 ,3-diyl oder Butan- 1 ,4-diyl steht,
R4 für Hydroxy, für Formyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylamino- carbonyloxy, n- oder i-Propylaminocarbonyloxy, Methylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyloxy, Butenyl- oxy, Propinyloxy oder Butinyloxy, für jeweils gegebenenfalls durchEthylthio, n- or i-propylthio, or for phenyl, or - if m is 2 - optionally together with a second radical R 3 for oxygen, propane-1, 3-diyl or butane 1, 4 -diyl stands, R 4 for hydroxy, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, each optionally substituted by fluorine and / or chlorine, Propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy and for optionally / or chlorine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally by
Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyloxy, Phenylthio, Phenyl- sulfinyl, Phenylsulfonyl, Phenylcarbonyloxy, Phenylcarbonyl- methoxy, Phenylsulfonyloxy, Phenylmethoxy, Phenylmethylthio,Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, Phenylcarbonyl methoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio,
Phenylmethylsulfinyl oder Phenylmethylsulfonyl steht,Phenylmethylsulfinyl or phenylmethylsulfonyl,
R5 für Wasserstoff, Cyano, Fluor, Chlor, für jeweils gegebenenfalls durch Fluor und oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-R 5 for hydrogen, cyano, fluorine, chlorine, for methyl, ethyl, n- or i-propyl, meth- or ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i, each optionally substituted by fluorine and or chlorine -
Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, oder für jeweils gegebenenfalls durch Cyano, Fluor, Chlor oder Methyl substituiertes Cyclopropyl steht,Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl,
R6 für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Propenyl, Butenyl, Propinyl oder Butinyl, für jeweils gegebenenfalls durch Fluor, Chlor oder Methyl substituiertesR 6 for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally by fluorine or chlorine substituted propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or methyl
Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, oder für
jeweils gegebenenfalls durch Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl oder Phenylmethyl steht,Cyclopropyl, Cyclobutyl, Cyclopentyl or Cyclohexyl, or for each is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy,
R7 für Hydroxy, für Formyloxy, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy, Ethoxy, n- oder i-Propoxy substituiertes Methoxy, Ethoxy, n- oder i-Propoxy, Acetyloxy, Propionyloxy, n- oder i-Butyroyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- oder i-Propoxycarbonyloxy, Methylaminocarbonyloxy, Ethylamino- carbonyloxy, n- oder i-Propylaminocarbonyloxy, Methylsulfonyloxy, Ethylsulfonyloxy, n- oder i-Propylsulfonyloxy, für jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Propenyloxy, Butenyloxy, Propinyloxy oder Butinyloxy, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-R 7 for hydroxy, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy optionally substituted by fluorine and / or chlorine, propenyloxy, Propynyloxy or butynyloxy, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-
Propyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenylmethoxy, Phenyl- carbonyloxy, Phenylcarbonylmethoxy oder Phenylsulfonyloxy steht,Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy,
R8 für Wasserstoff, Cyano, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl steht,R 8 represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
R9 für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor,R 9 for hydrogen, for each optionally by fluorine, chlorine,
Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertesMethoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, or for optionally substituted by fluorine, chlorine or methyl
Cyclopropyl steht,
R10 für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, oder für gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl steht, undCyclopropyl stands, R 10 represents hydrogen, in each case represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl optionally substituted by fluorine, chlorine or methyl, and
R11 für Wasserstoff, Cyano, Fluor, Chlor, Brom, oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl,R 11 represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, Ethoxycarbonyl, n- or i-propoxycarbonyl,
Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl steht.Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
5. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass5. Compounds of formula (I) according to claim 1, characterized in that
R1 für Wasserstoff, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, für Methoxy oder Ethoxy oder für die Gruppierung -C(Q)-R2 steht,R 1 represents hydrogen, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, methyl, ethyl, n- or i-propyl, methoxy or ethoxy or the group -C (Q) -R 2 ,
R2 für Wasserstoff, Amino, Hydrazino, für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl oder n- oder i-Propyl, für Dimethylamino, für jeweils gegebenenfalls durch Fluor, Chlor oder Methyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, für jeweils gegebenenfalls durch Nitro,R 2 for hydrogen, amino, hydrazino, for each methyl, ethyl or n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for dimethylamino, for cyclopropyl, cyclobutyl, cyclopentyl, each optionally substituted by fluorine, chlorine or methyl or cyclohexyl, each optionally with nitro,
Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy oder n- oder i-Propoxy substituiertes Phenyl, Phenylamino, Phenylmethyl oder Phenylethyl, oder für jeweils gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Tri- fluormethyl, Dichlormethyl, Trichlormethyl, Chlordifluormethyl,Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy or n- or i-propoxy substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine , Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl,
Fluordichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluor-
methylfhio, Trifluormethylthio, Methoxycarbonyl, Ethoxycarbonyl, substituiertes Furyl, Furylmethyl, Thienyl, Thienylmethyl, Pyrrolyl oder Pyrrolylmethyl steht,Fluorodichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoro methylfhio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, substituted furyl, furylmethyl, thienyl, thienylmethyl, pyrrolyl or pyrrolylmethyl,
X für Wasserstoff, Nitro, Fluor, Chlor, Brom, Methyl, Ethyl oder Trifluormethyl steht,X represents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl,
Y für Wasserstoff, Nitro, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Dichlormethyl, Trichlormethyl, Meth- oxymethyl, Methylthiomethyl, Methylsulfinylmethyl, Methylsulfonylmethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl oder Dimethylaminosulfonyl steht,Y for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
R3 für Wasserstoff oder jeweils gegebenenfalls durch Fluor und/oderR 3 represents hydrogen or in each case optionally by fluorine and / or
Chlor substituiertes Methyl oder Ethyl steht,Chlorine substituted methyl or ethyl,
R4 für Hydroxy steht,R 4 represents hydroxy,
R5 für Wasserstoff, Fluor, Chlor oder für jeweils gegebenenfalls durchR 5 for hydrogen, fluorine, chlorine or for each optionally by
Fluor und/oder Chlor substituiertes Methyl, Ethyl, Methoxy oder Ethoxy steht,Fluorine and / or chlorine substituted methyl, ethyl, methoxy or ethoxy,
R6 für Wasserstoff oder für jeweils gegebenenfalls durch Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht,R 6 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R7 für Hydroxy, für jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Methoxy oder Ethoxy, oder für gegebenenfalls durch Nitro, Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl,R 7 for hydroxyl, for methoxy or ethoxy which are each optionally substituted by fluorine or chlorine, or for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Methoxy oder Ethoxy substituiertes Phenylmethoxy steht.
Verfahren zum Herstellen von Verbindungen der Formel I gemäß Anspruch 1, dadurch gekennzeichnet, dass manMethoxy or ethoxy substituted phenylmethoxy. A process for the preparation of compounds of formula I according to claim 1, characterized in that
(a) Verbindungen der allgemeinen Formel (II)(a) compounds of the general formula (II)
in welcher in which
1 9 1 A , A , R , X, Y und Z die in Anspruch 1 angegebene Bedeutung haben,1 9 1 A, A, R, X, Y and Z have the meaning given in claim 1,
mit Verbindungen der allgemeinen Formel (III)with compounds of the general formula (III)
in welcher in which
Q und R2 die in Anspruch 1 angegebenen Bedeutung haben undQ and R 2 have the meaning given in claim 1 and
Q1 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio steht,Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio,
- oder gegebenenfalls mit entsprechenden Iso(thio)cyanaten -- or, if appropriate, with corresponding iso (thio) cyanates -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel um- setzt,
oder dass manif appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents, or that one
(b) Carbonsäuren der allgemeinen Formel (IV)(b) carboxylic acids of the general formula (IV)
in welcher in which
A , A , Q, R , R , X und Y die in Anspruch 1 angegebene Bedeutung habenA, A, Q, R, R, X and Y have the meaning given in claim 1
- oder reaktionsfähige Derivate hiervon, wie z.B. entsprechende Säurehaloge- nide, Säurecyanide oder Ester -- or reactive derivatives thereof, e.g. corresponding acid halides, acid cyanides or esters -
mit Verbindungen der allgemeinen Formel (V)with compounds of the general formula (V)
H-Z (V) in welcherH-Z (V) in which
Z die in Anspruch 1 angegebene Bedeutung hat,Z has the meaning given in claim 1,
gegebenenfalls in Gegenwart eines Dehydratisierungsmittel sowie gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder dass man
(c) substituierte Benzoylketone der allgemeinen Formel (Ia)or that one (c) substituted benzoyl ketones of the general formula (Ia)
in welcher in which
A1, A2, Q, R1, R2, R10, X und Y die in Anspruch 1 angegebene Bedeutung haben,A 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y have the meaning given in claim 1,
mit einem Orthoameisensäureester oder mit einem N,N-Dimefhyl-formamid- acetal oder mit einem Cyanoameisensäureester oder mit Carbondisulfid (Schwefelkohlenstoff) und einem Alkylierungsmittel und anschließend mit Hydroxylamin oder einem Säureaddukt hiervonwith an orthoformic acid ester or with an N, N-dimethylformamide acetal or with a cyanoformic acid ester or with carbon disulfide (carbon disulfide) and an alkylating agent and then with hydroxylamine or an acid adduct thereof
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder dass manor that one
(d) Arylketone der allgemeinen Formel (VI)(d) aryl ketones of the general formula (VI)
in welcher in which
A1, A2, Q, R1, X, Y und Z die in Anspruch 1 angegebene Bedeutung haben undA 1 , A 2 , Q, R 1 , X, Y and Z have the meaning given in claim 1 and
Q2 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio steht,Q 2 represents halogen, alkoxy, alkylthio, aryloxy or arylthio,
- oder gegebenenfalls entsprechende Iso(thio)cyanate -- or, if appropriate, corresponding iso (thio) cyanates -
mit Verbindungen der allgemeinen Formel (VII)with compounds of the general formula (VII)
H-R2 (VII) in welcherHR 2 (VII) in which
R2 die in Anspruch 1 angegebene Bedeutung hat,R 2 has the meaning given in claim 1,
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
und gegebenenfalls im Anschluss an die Durchführung der Verfahren (a), (b), (c) oder (d) an den so erhaltenen Verbindungen der allgemeinen Formel (I) Folgeumsetzungen zur Umwandlung in andere Verbindungen der allgemeinen Formel (I) nach üblichen Methoden durchführt.and optionally following the implementation of processes (a), (b), (c) or (d) on the compounds of the general formula (I) thus obtained, subsequent reactions for conversion into other compounds of the general formula (I) by customary methods performs.
Verbindungen der Formel (fl)
in welcherCompounds of formula (fl) in which
A1, A2, R1, X, Y und Z die in Anspruch 1 angegebene Bedeutung haben.A 1 , A 2 , R 1 , X, Y and Z have the meaning given in claim 1.
Verfahren zum Herstellen von Verbindungen der Formel (II), dadurch gekennzeichnet, dass man Verbindungen der allgemeinen Formel (VIII)Process for the preparation of compounds of the formula (II), characterized in that compounds of the general formula (VIII)
in welcher in which
A , 1 , A A 2 , X, Y und Z die in Anspruch 1 angegebene Bedeutung haben undA, 1, A A 2, X, Y and Z have the meaning given in claim 1 and
X für Halogen steht,X represents halogen,
mit Ammoniak oder Aminoverbindungen der allgemeinen Formel (IX)with ammonia or amino compounds of the general formula (IX)
in welcher in which
R1 die in Anspruch 1 angegebene Bedeutung hat,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, gegebenenfalls unter erhöhtem Druck bei Temperaturen zwischen 0°C und 100°C umsetzt.R 1 has the meaning given in claim 1, if appropriate in the presence of a diluent, if appropriate under elevated pressure at temperatures between 0 ° C. and 100 ° C.
9. Verbindungen der Formel (IV)9. Compounds of formula (IV)
in welcher in which
A , A , r Q, τ R, l , R , X und Y die in Anspruch 1 angegebene Bedeutung haben.A, A, r Q, τ R, l, R, X and Y have the meaning given in claim 1.
10. Verfahren zum Herstellen von Verbindungen der Formel (IV), dadurch gekennzeichnet, dass man10. A process for the preparation of compounds of formula (IV), characterized in that
(α) Verbindungen der allgemeinen Formel (X)(α) compounds of the general formula (X)
in welcher in which
A1, A2, Q, X und Y die in Anspruch 1 angegebene Bedeutung haben undA 1 , A 2 , Q, X and Y have the meaning given in claim 1 and
R für Wasserstoff, ein Alkalimetall- oder Erdalkalimetall-äquivalent oder Alkyl steht,
mit Verbindungen der allgemeinen Formel (VII)R represents hydrogen, an alkali metal or alkaline earth metal equivalent or alkyl, with compounds of the general formula (VII)
H-R »2z (VII) in welcherHR »2 z (VII) in which
R2 die in Anspruch 1 angegebene Bedeutung hat,R 2 has the meaning given in claim 1,
gegebenenfalls in Gegenwart eines Verdünnungsmittels bei Temperaturen zwischen 0°C und 100°C umsetzt und gegebenenfalls im Anschluss daran eine Esterverseifung nach üblichen Methoden durchführt,if appropriate in the presence of a diluent at temperatures between 0 ° C. and 100 ° C. and if appropriate subsequently carrying out an ester hydrolysis by customary methods,
oder dass manor that one
(ß)Verbindungen der allgemeinen Formel (XI)(β) compounds of the general formula (XI)
in welcher in which
A . 1 , A Λ 2 , T R> 1 , X und Y die in Anspruch 1 angegebene Bedeutung haben undA. 1, A Λ 2, T R> 1, X and Y have the meaning given in claim 1 and
R für Wasserstoff, ein Alkalimetall- oder Erdalkalimetall-äquivalent oder Alkyl steht,R represents hydrogen, an alkali metal or alkaline earth metal equivalent or alkyl,
mit (Thi)Oxoverbindungen der allgemeinen Formel (TU)
in welcherwith (thi) oxo compounds of the general formula (TU) in which
Q und R2 die in Anspruch 1 angegebene Bedeutung haben undQ and R 2 have the meaning given in claim 1 and
Q1 für Halogen, Alkoxy, Alkylthio, Aryloxy oder Arylthio steht,Q 1 represents halogen, alkoxy, alkylthio, aryloxy or arylthio,
- oder gegebenenfalls mit entsprechenden Iso(thio)cyanaten -- or, if appropriate, with corresponding iso (thio) cyanates -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel bei Temperaturen zwischen 0°C und 100°C umsetzt.if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents at temperatures between 0 ° C. and 100 ° C.
11. Verbindungen der Formel (Ia)11. Compounds of the formula (Ia)
in welcher in which
A1, A2, Q, R1, R2, R10, X und Y die in Anspruch 1 angegebene Bedeutung haben.A 1 , A 2 , Q, R 1 , R 2 , R 10 , X and Y have the meaning given in claim 1.
12. Herbizide Mittel, gekennzeichnet durch den Gehalt mindestens einer Verbindung gemäß einem der Ansprüche 1 bis 5 und den üblichen Streckmitteln.
12. Herbicidal agents, characterized by the content of at least one compound according to one of claims 1 to 5 and the usual extenders.
13. Verwendung von mindestens einer Verbindung gemäß einem der Ansprüche 1 bis 5 oder eines Mittels gemäß Anspruch 12 zur Bekämpfung von unerwünschten Pflanzen.13. Use of at least one compound according to one of claims 1 to 5 or an agent according to claim 12 for controlling unwanted plants.
14. Verfahren zum Bekämpfen von unerwünschten Pflanzen, dadurch gekennzeichnet, dass man mindestens eine Verbindung gemäß einem der Ansprüche 1 bis 5 oder ein Mittel gemäß Anspruch 12 auf die unerwünschten Pflanzen und/oder ihren Lebensraum einwirken lässt.
14. A method for controlling unwanted plants, characterized in that at least one compound according to one of claims 1 to 5 or an agent according to claim 12 is allowed to act on the unwanted plants and / or their habitat.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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DE10122445 | 2001-05-09 | ||
DE10122445 | 2001-05-09 | ||
DE10136449 | 2001-07-26 | ||
DE10136449A DE10136449A1 (en) | 2001-05-09 | 2001-07-26 | Substituted aryl ketones |
PCT/EP2002/004701 WO2002090336A1 (en) | 2001-05-09 | 2002-04-29 | Substituted arylketones |
Publications (1)
Publication Number | Publication Date |
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EP1387831A1 true EP1387831A1 (en) | 2004-02-11 |
Family
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Family Applications (1)
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EP02730220A Withdrawn EP1387831A1 (en) | 2001-05-09 | 2002-04-29 | Substituted arylketones |
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US (2) | US7112554B2 (en) |
EP (1) | EP1387831A1 (en) |
JP (2) | JP3897698B2 (en) |
CN (1) | CN1297543C (en) |
BR (1) | BR0209537A (en) |
CA (1) | CA2449187A1 (en) |
MX (1) | MXPA03010120A (en) |
PL (1) | PL365734A1 (en) |
RU (1) | RU2302411C2 (en) |
WO (1) | WO2002090336A1 (en) |
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RU2003135789A (en) | 2005-05-20 |
US20060252647A1 (en) | 2006-11-09 |
CN1297543C (en) | 2007-01-31 |
CN1524075A (en) | 2004-08-25 |
JP3897698B2 (en) | 2007-03-28 |
WO2002090336A1 (en) | 2002-11-14 |
JP2004534028A (en) | 2004-11-11 |
JP2007084549A (en) | 2007-04-05 |
US7112554B2 (en) | 2006-09-26 |
MXPA03010120A (en) | 2004-03-10 |
US7456133B2 (en) | 2008-11-25 |
CA2449187A1 (en) | 2002-11-14 |
BR0209537A (en) | 2004-03-09 |
PL365734A1 (en) | 2005-01-10 |
US20040176253A1 (en) | 2004-09-09 |
RU2302411C2 (en) | 2007-07-10 |
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