MX2008010702A - Cycloalkylphenyl substituted cyclic ketoenols - Google Patents
Cycloalkylphenyl substituted cyclic ketoenolsInfo
- Publication number
- MX2008010702A MX2008010702A MXMX/A/2008/010702A MX2008010702A MX2008010702A MX 2008010702 A MX2008010702 A MX 2008010702A MX 2008010702 A MX2008010702 A MX 2008010702A MX 2008010702 A MX2008010702 A MX 2008010702A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkoxy
- compounds
- formula
- optionally substituted
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 327
- 230000002363 herbicidal Effects 0.000 claims abstract description 35
- 239000004009 herbicide Substances 0.000 claims abstract description 19
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 Ci-C6 alkyl Chemical group 0.000 claims description 236
- 238000000034 method Methods 0.000 claims description 202
- 125000000217 alkyl group Chemical group 0.000 claims description 181
- 239000001257 hydrogen Substances 0.000 claims description 175
- 229910052739 hydrogen Inorganic materials 0.000 claims description 175
- 125000003545 alkoxy group Chemical group 0.000 claims description 152
- 150000002367 halogens Chemical group 0.000 claims description 142
- 229910052736 halogen Inorganic materials 0.000 claims description 140
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 136
- 150000002431 hydrogen Chemical group 0.000 claims description 133
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
- 239000002253 acid Substances 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 101
- 239000000460 chlorine Chemical group 0.000 claims description 94
- 229910052801 chlorine Inorganic materials 0.000 claims description 93
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 89
- 239000003085 diluting agent Substances 0.000 claims description 87
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 80
- 239000001301 oxygen Substances 0.000 claims description 80
- 229910052760 oxygen Inorganic materials 0.000 claims description 80
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 79
- 239000011737 fluorine Substances 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 78
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 70
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 70
- 125000001153 fluoro group Chemical group F* 0.000 claims description 69
- 125000001188 haloalkyl group Chemical group 0.000 claims description 67
- 239000011593 sulfur Substances 0.000 claims description 65
- 229910052717 sulfur Inorganic materials 0.000 claims description 65
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 57
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 57
- 229910052799 carbon Inorganic materials 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 41
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000004414 alkyl thio group Chemical group 0.000 claims description 31
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 26
- 239000011780 sodium chloride Substances 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 125000005842 heteroatoms Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000004429 atoms Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 150000007513 acids Chemical class 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 239000002516 radical scavenger Substances 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 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 15
- 150000004820 halides Chemical class 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 230000001276 controlling effect Effects 0.000 claims description 8
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 8
- 239000011630 iodine Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000000575 pesticide Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- MCNOFYBITGAAGM-UHFFFAOYSA-N (±)-Furilazole Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 6
- OZWKMVRBQXNZKK-UHFFFAOYSA-N Ketorolac Chemical class OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000005108 alkenylthio group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4H-pyrazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- ICJSJAJWTWPSBD-UHFFFAOYSA-M 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)[O-])=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-M 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005631 2,4-D Substances 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 4
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical compound N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 3
- YNQSILKYZQZHFJ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,5-trimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 3
- ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-N-[2-oxo-2-(prop-2-enylamino)ethyl]-N-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 claims description 3
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical compound 0.000 claims description 3
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- MWKVXOJATACCCH-UHFFFAOYSA-N ethyl 5,5-diphenyl-4H-1,2-oxazole-3-carboxylate Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- HZBAVWLZSLOCFR-UHFFFAOYSA-N oxosilane Chemical class [SiH2]=O HZBAVWLZSLOCFR-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atoms Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical compound 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- UKSLKNUCVPZQCQ-GZTJUZNOSA-N (E)-1-(4-chlorophenyl)-N-(1,3-dioxolan-2-ylmethoxy)-2,2,2-trifluoroethanimine Chemical compound C=1C=C(Cl)C=CC=1/C(C(F)(F)F)=N\OCC1OCCO1 UKSLKNUCVPZQCQ-GZTJUZNOSA-N 0.000 claims description 2
- PYKLUAIDKVVEOS-JLHYYAGUSA-N (Z)-N-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(/C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-JLHYYAGUSA-N 0.000 claims description 2
- VXJKYWLPNZBSMY-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(naphthalen-1-ylsulfamoyl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC=C12 VXJKYWLPNZBSMY-UHFFFAOYSA-N 0.000 claims description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 claims description 2
- JTBBWRKSUYCPFY-UHFFFAOYSA-N 2,3-dihydro-1H-pyrimidin-4-one Chemical compound O=C1NCNC=C1 JTBBWRKSUYCPFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002794 2,4-DB Substances 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-Dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
- AXHCGXRBOHBEQA-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C=C1OCC(O)=O AXHCGXRBOHBEQA-UHFFFAOYSA-N 0.000 claims description 2
- YNDNIPMGZASSRG-UHFFFAOYSA-N 2-methoxy-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(OC)C1=CC=CC=C1 YNDNIPMGZASSRG-UHFFFAOYSA-N 0.000 claims description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-M 3,6-dichloro-2-methoxybenzoate Chemical compound COC1=C(Cl)C=CC(Cl)=C1C([O-])=O IWEDIXLBFLAXBO-UHFFFAOYSA-M 0.000 claims description 2
- YJJIKUFGJJZYIX-UHFFFAOYSA-N 4-(5-chloro-2-methylphenyl)butanoic acid Chemical compound CC1=CC=C(Cl)C=C1CCCC(O)=O YJJIKUFGJJZYIX-UHFFFAOYSA-N 0.000 claims description 2
- ZAYKVYVNMLEAMI-UHFFFAOYSA-N 4-(carboxymethyl)-2,3-dihydrochromene-4-carboxylic acid Chemical compound C1=CC=C2C(CC(=O)O)(C(O)=O)CCOC2=C1 ZAYKVYVNMLEAMI-UHFFFAOYSA-N 0.000 claims description 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N 4-Chlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 2
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005574 MCPA Substances 0.000 claims description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N Mecoprop Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
- CMCJQHLLWDPWPK-UHFFFAOYSA-N N-[4-(cyclopropylcarbamoyl)phenyl]sulfonyl-2-methoxy-5-methylbenzamide Chemical compound COC1=CC=C(C)C=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 CMCJQHLLWDPWPK-UHFFFAOYSA-N 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- 102100014526 TBC1D8 Human genes 0.000 claims description 2
- 101710035852 TBC1D8 Proteins 0.000 claims description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006323 alkenyl amino group Chemical compound 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- QJBRNNNJBVJKPK-UHFFFAOYSA-N but-1-en-3-yne Chemical group C=[C]C#C QJBRNNNJBVJKPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 2
- JEMXUSHXYOXNFL-UHFFFAOYSA-N ethyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC)=CC=C(Cl)C2=C1 JEMXUSHXYOXNFL-UHFFFAOYSA-N 0.000 claims description 2
- YNZGZAJXHXGDBF-UHFFFAOYSA-N ethyl 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1C1=CC=CC=C1 YNZGZAJXHXGDBF-UHFFFAOYSA-N 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- DSLIOOISXCVKML-UHFFFAOYSA-N methyl 2-(8-chloroquinoxalin-5-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC)=CC=C(Cl)C2=N1 DSLIOOISXCVKML-UHFFFAOYSA-N 0.000 claims description 2
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- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 230000002633 protecting Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 229960002132 pyrrolnitrin Drugs 0.000 description 1
- 229910052904 quartz Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N τ-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
Abstract
The invention relates to novel cycloalkylphenyl substituted cyclic ketoenols of formula (I), where J, X, Y, m and CKE have the given meanings, method and intermediates for production thereof and use thereof as pest control agent and/or herbicide. The invention further relates to selective herbicides containing cycloalkylphenyl substituted cyclic ketoenols and a compound improving the cultivated plant tolerance. The invention also relates to the increase in efficacy of plant protection agents containing compounds of formula (I) by the addition of ammonium or phosphonium salts and optionally penetration improvers.
Description
CETOENOLES CYCLES REPLACED WITH CYCLAL ALCHYLPHENYL
FIELD OF THE INVENTION The present invention relates to cyclic ketoenols substituted with cycloalkylphenyls, to a plurality of processes for their preparation and use as pesticides and / or herbicides. The invention also provides selective herbicidal compositions comprising, first, the cyclic ketoenols substituted with cycloalkylphenyls and, second, a compound for improving the compatibility of crop plants. The present invention further relates to increasing the activity of crop protection compositions comprising, in particular, cyclic ketoenols substituted with cycloalkylphenyls by the addition of ammonium or phosphonium salts and, if appropriate, penetrants, to the corresponding compositions, to procedures for their preparation and their use in the protection of crops such as insecticides and / or acaricides and / or to prevent unwanted vegetation.
BACKGROUND OF THE INVENTION The pharmaceutical properties of 3-acylpyrrolidin-2,4-diones are described in the prior art (S. Suzuki et al., Chem. Pharm. Bull. 15 1120 (1967)). In addition, R. Schmierer
REF. : 195579
and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095) synthesized N-phenylpyrrolidin-2,4-diones. No biological activity of these compounds has been described. EP-A-0 262 399 and GB-A-2 266 888 describe compounds of a similar structure (3-arylpyrrolidin-2,4-diones); however, no herbicidal, insecticidal or acaricidal action of these compounds is known. The unsubstituted bicyclic derivatives of 3-arylpyrrolidin-2,4-dione are known to have a herbicidal, insecticidal or acaricidal action (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670). , and also substituted monocyclic derivatives of 3-arylpyrrolidin-2,4-dione (EP-A-377 893 and EP-A-442 077). Polycyclic derivatives of 3-arylpyrrolidin-2,4-dione (EP-A-442 073), and also derivatives of lH-arylpyrrolidinedione are also known (EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96 / 25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99 / 16748, WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/007448, WO 04 / 024688, WO 04/065366, WO 04/080962, WO 04/111042, WO 05/044791, O 05/044796, WO 05/048710, WO 05/049596, WO 05/066125, WO
- -
05/092897, WO 06/000355, WO 06/029799, WO 06/056281, WO 06/056282, O 06/089633, DE-A-05051325, DE-A-05059891). It is known that certain derivatives of A3-dihydrofuran-2-one have herbicidal properties (see DE-A-4 014 420). The synthesis of the tetronic acid derivatives (such as, for example, 3- (2-methylphenyl) -4-hydroxy-5- (4-fluorophenyl) -? 3 -dihydrofuranone- (2) which are used as starting materials are also described in DE-A-4 014 420. From the publication of Campbell et al., J.
Chem. Soc, Perkin Trans. 1, 1985, (8) 1567-76 compounds of a similar structure are known whose insecticidal and / or acaricidal activity is not discussed. In addition, 3-aryl-3-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO 99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354 and WO 01/74770, WO 03/013 249, WO 04/024 688, WO
04/080 962, WO 04/111 042, WO 05/092897, WO 06/000355, WO06 / 029799, WO 06/089633, DE-A-05051325, DE-A-05059891.
The derivatives of 3-aryl-β-dihydrothiophenone are also known (WO 95/26 345, 96/25 395, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05638, WO 98/25928, WO
- -
99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17772, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/080 962, WO 04/111 042. , WO 05/092897, WO 06/029799). Certain unsubstituted derivatives in the phenyl ring of phenylpyrone are already known (see AM Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. .9_1, 2849); however, a possible use of these compounds as pesticides is not reported. Phenylpyrone derivatives which are substituted on the phenyl ring and have herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97 / 02 243, WO 97/16 436, WO 97/19 941, WO 97/36 868, WO 98/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01 / 74770, WO 03/013249, WO 04/080 962, WO 04/111 042, WO 05/092897, WO 06/029799. Certain derivatives of 5-phenyl-1,3-thiazine which are unsubstituted in the phenyl ring are already known (see E. Ziegler and E. Steiner, Monatsh 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl, Chem. 1_0, 223 (1973)); however, a possible use of these compounds as pesticides is not reported. In WO 94/14 785, WO 96/02 539, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/02 243, WO 97/36 868, WO 99/05638, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962, WO
- -
04/111 042, WO 05/092897, O 06/029799 describes 5-phenyl-1,3-thiazine derivatives which are substituted on the phenyl ring and have herbicidal, acaricidal and insecticidal action. It is known that certain substituted 2-arylcyclopentanediones have herbicidal, insecticidal and acaricidal properties (see, for example, US-4 283 348, 4 338 122, 4 436 666, 4 526 723, 4 551 547, 4 632 698; 96/01 798, WO 96/03 366, WO 97/14 667 and also WO 98/39281, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03 / 013249, WO 04/080 962, WO 04/111 042, WO 05/092897, WO 06/029799). Compounds substituted in a similar manner are also known; 3-hydroxy-5, 5-dimethyl-2-phenyl-cyclopent-2-en-l-one from the publication of Micklefield et al., Tetrahedron, (1992), 7519-26 and the natural compound involutin (- ) -cis -5- (3, 4-dihydroxyphenyl) -3,4-dihydroxy-2- (4-hydroxyphenyl) cyclopent-2-enone from the publication of Edwards et al., J. Chem. Soc. S, (1967), 405-9. No insecticidal or acaricidal action is described. 2- (2,4,6-Trimethylphenyl) -1,3-indandione is also known from the publication J. Economic Entomology, 6_6, (1973), 584 and open publication for public inspection of document DE-A 2 361 084, citing herbicidal and acaricidal actions. It is known that certain substituted 2-arylcyclohexanediones have herbicidal, insecticidal and acaricidal properties (US Pat. Nos. 4 175 135, 4 209 432, 4 256 657, 4 256 658,
- -
4 256 659, 4 257 858, 4 283 348, 4 303 669, 4 351 666, 4 409 153, 4 436 666, 4 526 723, 4 613 617, 4 659 372, DE-A 2 813 341, and also Wheeler , TN, J. Org. Chem. 44, 4906 (1979)), WO 99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/013249, WO 04/080 962, WO 04 / 111 042, WO 05/092897, WO 06/029799). It is known that certain substituted 4-arylpyrazolidin-3,5-diones have acaricidal, insecticidal and herbicidal properties (see, for example, WO 92/16 510, EP-A-508 126, WO 96/11 574, WO 96 / 21 652, WO 99/47525, WO 01/17 351, WO 01/17 352, WO 01/17 353, WO 01/17 972, WO 01/17 973, WO 03/028 466, WO 03/062 244 , WO 04/080 962, WO 04/111 042, WO 05/005428, WO 05/016873, WO 05/092897, WO 06/029799).
It is known that certain tetrahydropyridones have herbicide properties: JP-A-0 832 530. Specific 4-hydroxytetrahydropyridones having acaricidal, insecticidal and herbicidal properties are also known: JP-A-11 152 273. In addition, 4-hydroxytetrahydro- pyridones as pesticides and herbicides in WO 01/79204. It is further known that certain 5,6-dihydropyrone derivatives as protease inhibitors have antiviral properties: WO 95/14012. In addition, 4-phenyl-6 - (2-phenethyl) -5,6-dihydropyrone is known from the synthesis of kavalactone derivatives: Kappe et al., Arch. Pharm. 309,
- -
558-64 (1976). Also, 5,6-dihydropyrone derivatives are known as intermediates: White, J.D., Brenner, J.B., Deinsdale, M.J., J. Amer. Chem. Soc. 93, 281-2 (1971). In O 01/98288 there are disclosed 3-phenyl-5,6-dihydropyrone derivatives which can be applied as crop protection agents. However, the efficacy and spectrum of activity of these compounds, in particular at application rates and low concentrations, are not always satisfactory. In addition, the compatibility of these compounds with crops is not always sufficient.
DETAILED DESCRIPTION OF THE INVENTION This invention now provides novel compounds of the formula (I)
wherein J represents optionally substituted cycloalkyl which may optionally be interrupted by heteroatoms, X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy, Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
- - m represents a number 1, 2 or 3, with the proviso that at least one of the radicals J, X or Y is located at position 2 of the phenyl radical and is not hydrogen, CKE represents one of the groups
in which
- -
A represents hydrogen, in each case alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl optionally substituted by halogen, saturated or unsaturated cycloalkyl optionally substituted wherein optionally at least one ring atom is substituted with one heteroatom, or aryl, arylalkyl or hetaryl in each case optionally substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro. B represents hydrogen, alkyl or alkoxyalkyl, or A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cyclic residue which optionally contains at least one heteroatom, D represents hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl wherein optionally one or more ring members are substituted by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or A and D together with the atoms to which they are attached represent a saturated or unsaturated cyclic moiety that is unsubstituted or substituted on the moiety A, D and optionally contains at least one heteroatom (in the case of CKE = 8 an additional one), or A and Q1 together represent alkanediyl or alkenediyl which
- - is optionally interrupted by a carbonyl group or heteroatoms, which are optionally substituted by optionally substituted halogen, hydroxyl, -alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl in each case and in which optionally two not directly adjacent carbon atoms form an additional optionally substituted cyclic moiety that can optionally be interrupted by heteroatoms or D and Q1 together with the atoms to which they are attached represent a saturated or unsaturated cyclic moiety that optionally contains at least one heteroatom and is unsubstituted or is substituted on the remainder D, Q1, Q1 represents hydrogen, alkyl, alkoxyalkyl, optionally substituted cycloalkyl (wherein optionally a methylene group is replaced by oxygen or sulfur) or optionally substituted phenyl, Q2 / Q4 / Q5 and Q6 independently of one another represent hydrogen or alkyl, Q3 represents hydrogen, represents alkyl op optionally substituted, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (wherein optionally a methylene group is replaced by oxygen or sulfur) or optionally substituted phenyl, or Q1 and Q2 together with the carbon atom to which they are attached represent an unsubstituted cyclic moiety or replaced that
- - optionally contains a heteroatom, or Q3 and Q4 together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cyclic moiety that optionally contains a heteroatom, G represents hydrogen (a) or represents one of the groups
wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl in each case optionally substituted by halogen or cycloalkyl optionally substituted with halogen, alkyl or alkoxy which may be interrupted by at least one optionally substituted heteroatom, phenyl, phenyl-alkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R2 represents alkyl, alkenyl, alkoxyalkyl,
- - polyalkoxyalkyl in each case optionally substituted by halogen or represents optionally substituted cycloalkyl, phenyl or benzyl in each case, R3, R4 and R5 independently of one another represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio in each case optionally substituted with halogen or represents optionally substituted phenyl, benzyl, phenoxy or phenylthio in each case, R6 and R7 independently of each other represent hydrogen, represent alkyl, cycloalkyl, al-quenyl, alkoxy, alkoxyalkyl each optionally substituted with halogen, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the N atom to which they are attached represent a cyclic moiety that is optionally interrupted by oxygen or sulfur. Depending among others on the nature of the substituents, the compounds of the formula (I) may be present in the form of geometric and / or optical isomers or mixtures of isomers of variable composition which, if appropriate, may be separated in the customary manner. The present invention provides both pure isomers and mixtures of isomers, their preparation and use, and compositions comprising them. However, for simplicity,
- 1 - hereinafter only reference is made to the compounds of the formula (I), although what is intended is both the pure compounds and, if appropriate, also the mixtures having variable proportions of isomeric compounds. Including the meanings (1) to (10) of the CKE group, the following main structures (1-1) to (I-10) are obtained:
- -
as defined above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (Ila) a (Ilg) if CKE represents the group (1)
- -
(I-l-c) (I-l-d)
(I-l-e): (I-l-f):
(i-i-g)
wherein A, B, D, E, J, L, m, M, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -2-a) a ( ? -2-g) if CKE represents the
- -group 2 )
(?-2 g) :
R °
wherein A, B, E, J, L, m, M, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -3-a) a ( ? -3-g) if CKE represents the group (3)
- -
(? -3-c) (? -3-d)
wherein A, B, E, J, L, m, M, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above.
- -
Depending on the position of the substituent G, the compounds of the formula (1-4) may be present in the two isomeric forms of the formulas (I-4-A) and (I-4-B)
which is intended to be indicated by the dashed line of formula (1-4). The compounds of the formulas (1-A) and (I-4-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, the mixtures of the compounds of the formulas (I-4-A) and (I-4-B) can be separated in a manner known per se by physical methods, for example by chromatographic methods. For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the compounds may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -4-a) a ( ? -4-g) if CKE represents the
- - group () (? -4-b):
- -
(? -4-g):
wherein A, D, E, J, L, m, M, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -5-a) a ( ? -5-g) if CKE represents the group (5)
(? -5-a) (? -5-b)
- -
(? -5-c): (? -5-d):
(? -5-g):
wherein A, E, J, L, m, M, X, Y, R1, R2, R3, R, R5, R6 and R7 are as defined above. Depending on the position of substituent G, the
- - compounds of the formula (1-6) can be present in the two isomeric forms of the formulas (I-6-A) and (I-6-B)
(I-6-A) (I-6-B)
which is intended to be indicated by the dashed line of formula (I). The compounds of the formulas (I-6-A) and (I-6-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, the mixtures of the compounds of the formulas (I-6-A) and (I-6-B) can be separated by physical methods, for example by chromatographic methods. For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the compounds may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -6-a) a ( ? -6-g):
??
- -
(? -6-g):
wherein A, B, J, Q1, Q2, E, L, m, M, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Depending on the position of the substituent G, the compounds of the formula (1-7) may be present in the two isomeric forms of the formulas (I-7-A) and (I-7-B), which is intended to indicate by the dashed line of formula (1-7):
(I-7-A) (I-7-B) The compounds of the formulas (I-7-A) and (I-7-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, mixtures of the compounds of the formulas (I-7-A) and (I-7-B) can be separated
by physical procedures, for example by chromatographic methods. For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the relevant compound may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -7-a) a ( ? -7-g): (? -7-a): (? -7-b):
(? -7-c): (? -7-d)
- -
(? -7-e): (? -7-f):
wherein A, B, J, E, L, m, M, Q3, Q4, Q5, Q6, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Depending on the position of the substituent G, the compounds of the formula (1-8) can be present in the two isomeric forms the formulas (I-8-A) and (1-8-B)
which is intended to be indicated by the broken line in
- - the formula (1-8). The compounds of the formulas (I-8-A) and (I-8-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, the mixtures of the compounds of the formulas (I-8-A) and (I-8-B) can be separated in a manner known per se by physical methods, for example by chromatographic methods. For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the compounds may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -8-a) a ( ? -8-g) if CKE represents group (8) (l-8-a): (l-8-b):
- -
wherein A, D, E, J, L, M, m, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined above. Depending on the position of the substituent G, the compounds of the formula (1-9) may be present in the two isomeric forms of the formulas (I-9-A) and (I-9-B)
- -
(I-9-A) (I-9-B) which is intended to be indicated by the broken line in formula (1-9). The compounds of the formulas (I-9-A) and (I-9-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, the mixtures of the compounds of the formulas (I-9-A) and (I-9-B) can be separated in a manner known per se by physical methods, for example by chromatographic methods. For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the compounds may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -9-a) a ( ? -9-g) if CKE represents the group (9)
- - (? -9-a): (? -9-b):
- - (? -9-g):
wherein A, B, D, E, J, L, m, M, Q1, Q2, X, Y, R1, R, R3, R4, R5, Rs and R7 are as defined above. Depending on the position of the substituent G, the compounds of the formula (1-10) may be present in the two isomeric forms of the formulas (I-10-A) and (I-10-B)
(I-10-A) (I-10-B) which is intended to be indicated by the dashed line of formula (1-10). The compounds of the formulas (I-10-A) and (I-10-B) can be present both in the form of mixtures and in the form of their pure isomers. If appropriate, mixtures of
- compounds of the formulas (I-10-A) and (I-10-B) can be separated in a manner known per se by physical methods, for example by chromatographic methods.
For clarity, hereinafter only one of the possible ones is shown in each case. This does not prevent that, if appropriate, the compounds may be present in the form of mixtures of isomers or of the respective other isomeric form. Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures are obtained (? -10-a) a ( ? -10-g) if CKE represents group (10) (? -10-a): (? -10-b):
- -
(? -10-c): (? -10-d)
(? -10-e): (? -10-f):
(? -10-g)
wherein A, B, E, L, m, M, Q1, Q2, X, Y, R1, R2, R3, R4, R5, R6 and R7 as defined above.
Furthermore, it has been found that the novel compounds of the formula (I) are obtained by one of the methods described below: (A) 3-Substituted phenylpyrrolidine-2,4-diones or their enols of the formula (I-1-a)
wherein A, B, D, J, m, X and Y are as previously obtained when N-acylamino acid esters of the formula (
wherein A, B, D, J, m, X and Y are as defined above
and R8 represents alkyl (preferably Ci-C6 alkyl)
- - are condensed intramolecularly in the presence of a diluent and in the presence of a base. (B) In addition, it has been found that the substituted 3-phenyl-4-hydroxy-A3-dihydrofuranone derivatives of the formula (α -2-a)
wherein A, B, J, m, X and Y are as defined above are obtained when the carboxylic esters of the formula (III)
wherein A, B, J, m, X, Y and R8 are as defined above are condensed intramolecularly in the presence of a diluent and in the presence of a base. (C) In addition, it has been found that the substituted 3-phenyl-4-hydroxy-A3-dihydrothiophenone derivatives of the formula
- -
(? -3-a)
wherein A, B, J, m, X and Y are as defined above are obtained when β-ketocarboxylic esters of the formula (IV)
wherein A, B, J, m, X, Y and R8 are as defined above and V represents hydrogen, halogen, alkyl
(preferably Ci-C6 alkyl) or alkoxy (preferably Ci-C8 alkoxy) are cyclized intramolecularly, if appropriate in the presence of a diluent and in the presence of an acid. (D) In addition, it has been found that the novel substituted 3-phenylpyrone derivatives of the formula (? -4-a)
- -
wherein A, D, J, m, X and Y are as defined above are obtained when carbonyl compounds of the formula (V) O
D-C-CH2-A m
wherein A and D are as defined above or their silylene ethers of the formula (Va) CHA D - C - OS (R8) 3 (Va)
wherein A, D and R8 are as defined above are reacted with halides of ketonic acids of formula (VI)
wherein J, m, X and Y are as defined above and Hal represents halogen (preferably chlorine or bromine),
- - if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor. In addition, it has been found (E) that novel derivatives of substituted phenyl-1,3-thiazine of the formula (? -5-a)
wherein A, J, m, X and Y are as defined above are obtained when the thioamides of the formula (VII) S H2N-C-A (VI I)
wherein A is as defined above are reacted with halides of ketonic acids of the formula (VI)
wherein Hal, J, m, X and Y are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
- -
In addition, it has been found (F) that the compounds of the formula (? -6-a)
wherein A, B, Q1, Q2, J, m, X and Y are as defined above are obtained when ketocarboxyl esters of the formula (VIII)
wherein A, B, Q1, Q2, J, m, X and Y are as defined above and R8 represents alkyl (in particular CIB alkyl) are cyclized intramolecularly, if appropriate in the presence of a diluent and in presence of a base. It has also been found (G) that the compounds of the formula (? -7-a)
- -
wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above are obtained when 6-aryl-5-ketohexanoic esters of the formula (IX)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above
and R8 represents alkyl (preferably Ci-C6 alkyl) are condensed intramolecularly in the presence of a diluent and in the presence of a base. (H) In addition, it has been found that the compounds of the formula (? -8-a)
- -
wherein A, D, J, m, X and Y are as defined above are obtained when compounds of the formula (X) AHN (X) DH where A and D are as defined above a) are they react with compounds of the formula
(SAW)
wherein Hal, m, X, Y and J are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, or ß) are reacted with compounds of the formula
(XI)
- -
wherein J, m, X and Y are as defined above and U represents NH2 or O-R8, where R8 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or?) are reacted with compounds of the formula
(XII)
wherein A, D, J, m, X, Y and R8 are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of a base. Likewise, it has been found that the novel compounds of the formula (I) are obtained by one of the methods described below: (I) Tetrahydropyridin-2,4-substituted diones or their
- - Enols of the formula (? -9-a)
wherein A, B, D, J, m, Q1, Q2, X and Y are as defined above are obtained when N-acylamino acid esters of the formula (XIII)
wherein A, B, D, J, m, Q1, Q2, X and Y are as defined above
R represents alkyl (preferably Ci-C6 alkyl) are condensed intramolecularly in the presence of a diluent and in the presence of a base.
- -
In addition, (J) has been found that substituted 5,6-dihydropyrones of the formula (I-10-a)
wherein A, B, J, m, Q1, Q2, X and Y are as defined above are obtained when O-acylhydroxycarboxylic esters of the formula (XIV)
wherein A, B, J, m, Q1, Q2, X and Y are as defined above and R8 represents alkyl (preferably Ci-C6 alkyl) are condensed intramolecularly in the presence of a
- - diluent and in the presence of a base. It has also been found (K) that the compounds of the formulas (Ilb) to (1-10-b) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q \ Q5 , Q6, R1, X and Y are as defined above are obtained when compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1 , Q2, Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted (a) with acid halides of the formula (XV) Hal ^ R1 (XV)
wherein R1 is as defined above and Hal represents halogen (in particular chlorine or bromine) or (ß) with carboxylic anhydrides of the formula (XVI) Ri-CO-O-CO-R1 (XVI) wherein R1 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger; (L) than the compounds of the formulas (I-1-c) to (1-10-c) shown above in which A, B, D, J, m, Q1,
Q2, Q3, Q4, Q5, Q6, R2, M, X and Y are as defined above and L represents oxygen are obtained when compounds of the formulas (Ila) to (? -10-a) shown above in which A (B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted with chloroform esters or chloroform thioesters of the formula (XVII R2-M-C0-C1 (XVII) wherein R2 and M are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger; of the formulas (Ilc) to (1-10-c) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, R2, M, X and Y they are as defined above and L represents sulfur are obtained when compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q, Q3 , Q, Q5, Qe, X and Y are as defined above in each if they are reacted with chloromonothioform esters or chlorodithioform esters of the formula (XVIII)
(XVIII)
in which
- and R2 are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger, and (N) that the compounds of the formulas (Ild) to (1-10-) d) which are shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, R3, and Y are as defined above are obtained when compounds of the formulas (Ila) ) a (? -10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Qs, X and Y are as defined above in each case are reacted are reacted with sulfonyl chlorides of the formula (XIX) R3-S02-C1 (XIX) wherein R3 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger, (O) that the compounds of the formulas (Ile) to (1-10-e) shown above in which A, B, D, J, m, L, Q1, Q2, Q3, Q4, Q5, Q6 4 R5, X and Y are as defined They are obtained when compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X are And they are as defined above in each case
- - are reacted with phosphorus compounds of the formula (XX)
/ R4 Hal - P (xx) "s LR where L, R4 and R5 are as defined above and Hal represents halogen (in particular chlorine or bromine), if appropriate in the presence of a diluent and if appropriate in presence of an acid scavenger, (P) that the compounds of the formulas (Ilf) to (1-10-f) shown above in which A, B, D, E, J (m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above are obtained when compounds of the formulas (Ila) to (? -10-a) in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted with metal compounds or amines of the formulas (XXI) or (XXII)
R 10 R 11 Me (OR 10) t (XXI) 12 (XXII) R in which Me represents a monovalent or divalent metal (preferably an alkali metal or an alkaline earth metal, such as lithium, sodium, potassium, magnesium or calcium), or
represents an ammonium ion
R, 0s®, R1 ° N R11 / V2 t represents the number 1 or 2 and R10, R11, R12 independently of one another represent hydrogen or alkyl (preferably Ci-C8 alkyl), if appropriate in the presence of a diluent , (Q) than the compounds of the formulas (Ilg) to (1-10-g) shown above in which A, B, D, J, m, L, Q1, Q2, Q3, Q4, Q5, Q6, R6, R7, X and Y are as defined above are obtained when compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q5, X and Y are as defined above in each case
(a) are reacted with isocyanates or isothiocyanates of the formula (XXIII) R6-N = C = L (XXIII) wherein R6 and L are as defined above if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or (ß) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formulas (XXIV)
- -
wherein L, R6 and R7 are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger, (R) than the compounds of the formulas (Ila) to (1) -10- g) which are shown above in which A, B, D, G, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above are obtained when compounds of the formulas (? -1 ') a (I-lO'-g) in which A, B, D, G, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above and J 'preferably represents bromine or iodine
- -
they are coupled with cycloalkylboronic acid derivatives capable of coupling, for example with cycloalkylboronic acids of the formula (XXV)
J- (XXV) OH or its esters, in the presence of a solvent, in the presence of a catalyst (for example Pd complexes) and in the presence of a base (for example sodium carbonate, potassium dihydrogen phosphate). In addition, it has been found that novel compounds of
- the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides and / or herbicides. Surprisingly, it has also now been found that certain substituted cyclic ketoenols, when used together with the compound to improve the compatibility of crop plants (safener / antidotes) described below, are very good at preventing damage to crop plants and can be used with particular advantage as combined broad-spectrum products for the selective control of unwanted plants in the crops of the useful plants, such as, for example, in cereals, but also in corn, soybeans and rice. The invention also provides selective herbicidal compositions comprising an effective amount of a combination of active compounds comprising, as components, (a1) at least one substituted cyclic ketoenol of the formula (I) wherein CKE, J, m, X and Y are as defined above and (b1) at least one compound to improve the compatibility of crop plants from the following group of compounds: 4-dichloroacetyl-l-oxa-4-azaspiro [4, 5] decane (AD -67, MON-
- -
4660), l-dichloroacetylhexahydro-3, 3, 8a-trimethylpyrrolo [1, 2-a] pyrimidin-6 (2H) -one (dicyclonon, BAS-145138),
4 - . 4 - . 4-Dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (benoxacor), 5-chloroquinolin-8-oxyacetate 1-methylhexyl (cloquintocet-methyl - see also related compounds in documents EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3- (2-chlorobenzyl) -1- (1-methyl-1-phenylethyl) urea
(cumyluron), a- (cyanomethoximino) phenylacetonitrile
(cyometrinil), 2, 4-dichlorophenoxyacetic acid (2,4-D), (2,4-DB), 1- (1-methyl-1-phenylethyl) -3- (4-methylphenyl) urea of 4 - acid (2,4-dichlorophenoxy) butyric (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), Sl-methyl-1-phenylethyl piperidin-1-thiocarboxylate (dimepiperate), 2,2-dichloro -N- (2 - ??? - 2- (2 -propenylamino) ethyl) -N- (2 -propeni1) -acetamide (DKA-24), 2,2-dichloro-N, -di- 2 -propenylacetamide ( dichloride), 4,6-dichloro-2-phenylpyrimidine (phenchlorim), 1- (2,4-dichlorophenyl) -5-trichloromethyl-lH-1,2,4-triazole-3-ethylcarboxylate (fenchlorazole-ethyl- see also the compounds listed in EP-A-174562 and EP-A-346620), 2-chloro-4-trifluoromethylthiazole-5-phenylmethylcarboxylate (flurazole), 4-chloro-N- oxime (1, 3 -dioxolan-2-ylmethoxy) -a -trifluoroacetophenone (fluxofenim), 3-dichloro-acetyl-5- (2-furanyl) -2, 2-dimethyloxazolidine (furilazole, MON-13900), 4,5-dihydro-5, 5-diphenyl-3-isoxazolecarbox ethyl ilate (isoxadifen-ethyl - see also related compounds
- in WO-A-95/07897), 3,6-dichloro-2-methoxybenzoate of 1- (ethoxycarbonyl) ethyl (lactidiclor), (4-chloro-o-tolyloxy) acetic acid (MCPA), acid 2- (4-chloro-o-tolyloxy) ropionic (mecoprop), 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-diethyl dicarboxylate (mefenopyridyl) diethyl - also see the related compounds in WO-A-91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro [ 4, 5] decane-4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a- (1,3-dioxolan-2-ylmethoximino) phenylacetonitrile (oxabetrinyl),
2, 2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2 -propeni1) acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3 -dichloroacetyl-2, 2, 5-trimethyloxazolidine (R-29148), 4- (4-chloro-o-tolyl) butyric acid, 4- (4-chlorophenoxy) utyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate Ethyl 1- (2-chlorophenyl) -5-phenyl-lH-pyrazole-3-carboxylate, 1- (2,4-dichlorophenyl) -5-methyl-1H-pyrazole-3-ethylcarboxylate, 1- ( 2, 4-dichlorophenyl) -5-isopropyl-1H-pyrazole-3-ethylcarboxylate, 1- (2,4-dichloro-phenyl) -5- (1,1 -dimethylethyl) -lH-pyrazole-3-carboxylate from. ethyl, 1- (2,4-dichlorophenyl) -5-phenyl-1H-pyrazole-3-ethylcarboxylate (see also the related compounds in EP-A-269806 and EP-A-333131), 5 - ( 2,4-dichlorobenzyl) -2-isoxazolin-3-ethylcarboxylate, ethyl 5-phenyl-2-isoxazolin-3-carboxylate, 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-
- -
3 - . 3-ethyl carboxylate (see also the related compounds in WO-A-91/08202), 1,3-chloroquinolin-8-oxyacetate 1,3-dimethylbut-1-yl, 5-chloroquinolin-8-oxyacetate 4 allyloxybutyl, l-allyloxyprop-2-yl 5-chloroquinolin-8-oxyacetate, methyl 5-chloroquinoxalin-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxalin-8-oxyacetate, -chloroquinolin-8-oxyacetate-2-oxoprop-1-yl, 5-chloroquinolin-8-oxymethonate-diethyl, 5-chloroquinoxalin-8-diallyl-oxalonate, 5-chloroquinolin-8-oxymethonate-diethyl (see also related compounds in EP-A-582198), acid
4 -carboxychroman-4-ylacetic acid (AC-304415, see EP-A-613618), 4-chlorophenoxyacetic acid, 3, 3 * -dimethyl-4-methoxy-benzophenone, l-bromo-4-chloromethylsulfonylbenzene, l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (also known as N- (2-methoxybenzoyl) -4- [(methylaminocarbonyl) amino] benzenesulfonamide), 1- [4- ( N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-di-methylurea, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4 - (N-naphthylsulfamoyl) phenyl] -3,3-dimethylurea, N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds, defined by the general formulas, of the general formula (lia)
- -
or of the general formula (Ilb)
or of the formula (lie)
where m represents a number 0, 1, 2, 3, 4 or 5, A1 represents one of the divalent heterocyclic groups shown below
n represents a number 0, 1, 2, 3, 4 or 5, A2 optionally represents alkanediyl substituted with Ci-C4 alkyl and / or Ci-C4 alkoxycarbonyl and / or (Ci-C4 alkenyloxy) carbonyl having 1 or 2 carbon atoms; carbon, R14 represents hydroxyl, mercapto, amino, Ci-C6 alkoxy,
Ci-C6 alkylthio, Ci-C6 alkylamino or di (Ci-C4 alkyl) amino, R15 represents hydroxyl, mercapto, amino, Ci-C7 alkoxy, Ci-C6 alkenyloxy ((Ci-C6 alkenyloxy) Ci-C6 alkoxy, alkylthio Ci-C6, alkylamino Ci-Ce or di (Ci-C4 alkyl) amino, R16 represents Ci-C4 alkyl in each case optionally substituted with fluorine, chlorine and / or bromine, R17 represents hydrogen, Ci-C6 alkyl, C2 alkenyl C6 or C2-C3 alkynyl, (C1-C4 alkoxy) Ci-C4 alkyl, dioxolanylalkyl Ci-C4, furyl, furyalkyl Ci-C4 thienyl, thiazolyl, piperidinyl each optionally substituted with fluorine, chlorine and / or bromine, or phenyl optionally substituted with fluorine, chlorine and / or bromine or Ci-C4 alkyl, R18 represents hydrogen, Ci-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, (Ci-C4 alkoxy) Ci-C4 alkyl, dioxolanylalkyl Ci-C4 , furyl, C 1 -C 4 -arylaryl, thienyl, thiazolyl, piperidinyl each optionally substituted with fluorine, chlorine and / or bromine, or phenyl optionally substituted with fluorine, chlorine and / or bromine or C1-C4 alkyl, R17 and R18 also together represent C3-Ce or C2-C5 alkanediyl, each of which is optionally substituted by Ci-C4 alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, they form a 5 or 6 membered carbocycle, R19 represents hydrogen, cyano, halogen, or represents C1-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case
optionally substituted with fluorine, chlorine and / or bromine, R20 represents hydrogen, Ci-C6 alkyl, C3-C6 cycloalkyl or tri- (C1-C4 alkyl) silyl optionally substituted by hydroxyl, cyano, halogen or C-CJ alkoxy, R21 represents hydrogen, cyano, halogen, or represents Ci-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, X1 represents nitro, cyano, halogen, Ci-C4 alkyl, haloalkyl Cx-C4 , Ci-C4 alkoxy or Ci-C haloalkoxy, x2 represents hydrogen, cyano, nitro, halogen, alkyl
CÍ-CJ, haloalkyl Ci-C4, alkoxy 0? -04 or haloalkoxy CX-C4, X3 represents hydrogen, cyano, nitro, halogen, C1-C4 alkyl, Ci-C4 haloalkyl, C1-C4 alkoxy or Ci-C4 haloalkoxy, and / or the following compounds, defined by the general formulas, of the general formula (lid)
or of the general formula (lie)
t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R22 represents hydrogen or Ci-C4 alkyl / R23 represents hydrogen or Ci-C4 alkyl, R24 represents hydrogen, Ci-C3 alkyl, Ci-C6 alkoxy, Ci-C6 alkylthio, Ci-C6 alkylamino or di (C1-C4 alkyl) amino in each case optionally substituted with cyano, halogen or Ci-C4 alkoxy (or C3 cycloalkyl) -C6, C3-C6 cycloalkyloxy, C3-C6 cycloalkylthio or C3-C6 cycloalkylamino in each case optionally substituted with cyano, halogen or Ci-C4 alkyl, R25 represents hydrogen, Ci-C6 alkyl optionally substituted with cyano, hydroxyl, halogen or alkoxy Ci-C, C3-Ce alkenyl or C3-C6 alkynyl in each case optionally substituted with cyano or halogen, or C3-C6 cycloalkyl optionally substituted with cyano, halogen or Ci-C4 alkyl, R26 represents hydrogen, Ci-C6 alkyl optionally substituted with cyano, hydroxyl, halogen or C! -C4 alkoxy, C3-C6 alkenyl or C3-C6 alkynyl in each case nally substituted with cyano or halogen, C3-C6 cycloalkyl
- - optionally substituted with cyano, halogen or C 1 -C alkyl, or phenyl optionally substituted with nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cx-C4 alkoxy or Ci-C4 haloalkoxy, or together with R25 represents C2-C6 alkanoidyl or C2-C5 oxalkanoidyl in each case optionally substituted with Ci-C alkyl, X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamollo, hydroxyl, amino, halogen, C1-C4 alkyl, Ci-C4 haloalkyl, Ci-C4 alkoxy or Cx-C4 haloalkoxy, and X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, Ci-alkyl C, Ci-C4 haloalkyl, Cx-C alkoxy or Ci-C4 haloalkoxy. The formula (I) provides a general definition of the compounds according to the invention. Preferred substituents or ranges of the radicals listed in the formulas given above are illustrated below: J preferably represents C3-C8 cycloalkyl which may optionally be interrupted by oxygen and which may optionally be substituted with halogen, Ci-C6 alkyl , Ci-C6 alkoxy, haloalkyl-06 or phenyl or C3-C6 cycloalkyl optionally substituted by Ci-C4 alkyl, Ci-C4 alkoxy, halogen, Ci-C4 haloalkyl, Ci-C4 haloalkoxy, X preferably represents hydrogen, halogen, alkyl d-C6, haloalkyl Ci-C4, alkoxy Ci-C6 or haloalkoxy Cx-C4,
And preferably represents hydrogen, Ci-C6 alkyl, haloalkyl CÍ-CJ, halogen, Ci-C6 alkoxy or Ci-C4 haloalkoxy, m preferably represents a number 1, 2 or 3, with the proviso that at least one of the radicals J , X or Y is located at position 2 of the phenyl radical and is not hydrogen, CKE preferably represents one of the groups
- -
A preferably represents hydrogen or CX-C12 alkyl, C3-C8 alkenyl ((Ci-Cio alkoxy) -alkyl (Ci-Cio alkylthio) -Ci-C6 alkyl optionally substituted with halogen, C3-C8 cycloalkyl optionally substituted by halogen , Ci-C6 alkyl or Ci-C6 alkoxy in which optionally one or two not directly adjacent ring members are substituted by oxygen and / or sulfur or represent phenyl, naphthyl, hetaryl having 5 or 6 ring atoms (e.g. , furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl), phenyl-Ci-CG alkyl or naphthyl-C6 alkyl optionally substituted with halogen, Ci-C6 alkyl, Ci-C6 haloalkyl, alkoxy Ci-C6, Ci-C6 haloalkoxy, cyano or nitro or, B preferably represents hydrogen, Ci-Ci2 alkyl or (Ci-C8 alkoxy) Ci-C6 alkyl or A, B and the carbon atom to which they are attached preferably represent saturated C3-C10 cycloalkyl or unsaturated C5-C10 cycloalkyl, in the Which optionally a ring member is replaced by oxygen or sulfur and which are optionally monosubstituted or disubstituted by
- Ci-C8 alkyl (C3-Ci0 cycloalkyl, CX-C8 haloalkyl, Ci-C8 alkoxy ((Ci-C4 alkoxy) Ci-C4 alkoxy (Ci-C8 alkylthio, halogen or phenyl or A, B and the carbon atom to which they are attached preferably represent C3-C6 cycloalkyl which is substituted with an alkylene dicalyl group or by an alkylenedioxyl group or by an alkylenedithioyl group optionally containing one or two oxygen and / or sulfur atoms not directly adjacent and which is optionally substituted with alkyl Ci-C4, which group, together with the carbon atom to which it is attached, forms an additional ring of five to eight members, or A, B and the carbon atom to which they are attached preferably represent C3-C8 cycloalkyl or C5 cycloalkenyl -C8 in which two substituents together with the carbon atoms to which they are attached represent C2-C6 alkanediyl, C2-C6 alkenediyl or C4-C3 alkanediylioyl optionally substituted with Ci-C6 alkyl, Ci-Ce alkoxy or halogen in which optional A methylene group is replaced by oxygen or sulfur, D preferably represents hydrogen, alkyl-C12, C3-C8 alkenyl, C3-C8 alkynyl, (Ci-Ci0 alkoxy) C2-C8 alkyl optionally substituted with halogen, cycloalkyl C3-C8 optionally substituted with halogen, CX-C alkyl,
alkoxy d-C or haloalkyl d-C * ° 'in the < 3 optionally a ring member is substituted with oxygen or sulfur or phenyl, hetaryl having 5 or 6 ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl, pyrazoyl, pyrimidyl, pyrrolyl, thienyl or triazolyl), phenyl -Ci-C6 alkyl or hetaryl-Ci-C6 alkyl having 5 or 6 ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl or triazolyl) each optionally substituted by halogen, alkyl d-C6, haloalkyl Ci-C6, alkoxy Ci-C6, haloalkoxy C1-C5l cyano or nitro, or A and D together preferably represent C3-C6 alkanediyl or C3-Ce alkenediyl each optionally substituted in which optionally a methylene group it is replaced by a carbonyl, oxygen or sulfur group, the substituents being possible in each case: halogen, hydroxyl, mercapto or alkyl d-do, d-C6 alkoxy, Ci-C6 alkylthio, C3-C7 cycloalkyl, phenyl or benzyloxy in each case optionally substitute case with phenyl, or a C3-C6 alkanediyl group, C3-C6 alkenediyl or an additional butadienyl group which are optionally substituted by Ci-C6 alkyl or in which optionally two adjacent substituents together with the carbon atoms to which they are attached form an additional saturated or unsaturated cyclic moiety having 5 or 6 ring atoms (in the case of the compound of the formula
- -
(1-1) A and D in this case together with the atoms to which they are attached represent, for example, the AD-1 to AD-10 groups mentioned below) which may contain oxygen or sulfur or which optionally contain one of the following groups
or A and Q1 together preferably represent C3-C6 alkanediyl or C4-C6 alkenediyl, each of which is optionally monosubstituted or disubstituted with identical or different substituents from the group consisting of halogen; hydroxyl; Ci-Ci0 alkyl, C1-C6 alkoxy, alkylthio
- -
Ci-C6 C3-C7 cycloalkyl, each of which is optionally monosubstituted to trisubstituted with identical or different halogen substituents; and benzyloxy or phenyl, each of which is optionally monosubstituted to trisubstituted with identical or different substituents from the group consisting of halogen, Ci-C6 alkyl and Ci-C6 alkoxy; which C3-C6 alkanediyl or C4-C6 alkenediyl optionally contain one of the following groups
or has a bridge of a C1-C2 alkanediyl group or of an oxygen atom or D and Q1 together preferably represent C3-Cs alkanediyl which in each case is optionally monosubstituted or disubstituted with C1-C4 alkyl or C1-C alkoxy identical or different and is optionally interrupted by an atom of
Oxygen or Q1 preferably represents hydrogen, Ci-C6 alkyl, (Ci-C6 alkoxy) Ci-C2 alkyl, C3-C8 cycloalkyl optionally substituted by fluorine, chloro, Ci-C4 alkyl, haloalkyl C: .- C2 or C1-C4 alkoxy wherein optionally a methylene group is replaced by oxygen or sulfur or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 alkoxy, Ci-C2 haloalkyl, Ci-C2 haloalkoxy, cyano or nitro or Q2, Q4, Q5 and Qs independently of one another preferably represent hydrogen or C 1 -C 4 alkyl, Q 3 preferably represents hydrogen, C 1 -C 6 alkyl, (C 1 -C 6 alkoxy) C 1 -C 2 alkyl, (C 1 -C 6 alkyl) thioalkyl Ci-C 2 / C 3 cycloalkyl -C8 optionally substituted with CJ.sub.4 -C.sub.4 alkyl or C.sub.1 -C.sub.1 alkoxy wherein optionally a methylene group is replaced by oxygen or sulfur or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkyl , Ci-C2 haloalkoxy, cyano or nitro, Q1 and Q2 together with the carbon atom to which they are attached. preferably they represent C3-C7 cycloalkyl optionally substituted with Ci-C6 alkyl, Ci-C6 alkoxy or Ci-C2 haloalkyl in which optionally one ring member is replaced by oxygen or sulfur, or Q3 and Q4 together with the carbon atom at which are attached preferably represent a C3-C7 ring optionally substituted with C1-C4 alkyl, C1-C4 alkoxy or haloalkyl C! -C2
wherein optionally a ring member is replaced by oxygen or sulfur, G preferably represents hydrogen (a) or represents one of the groups
E (f) 0 - N. 7 (q) L R W in particular (a), (b), (c) or (g)
wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 preferably represents Ci-C2o alkyl, C2-C2o alkenyl (Ci-Cs alkoxy) Ci-Ce alkyl, (Ci-C8 alkylthio) Ci-C8 alkyl, (Ci-C8 polyalkoxy) Ci-c8 alkyl in each case optionally
substituted with halogen or C3-C8 cycloalkyl optionally substituted with halogen, Ci-C6 alkyl or Ci-C6 alkoxy in which optionally one or more (preferably not more than two) non-directly adjacent ring members are substituted by oxygen and / or sulfur , preferably represents phenyl optionally substituted with halogen, cyano, nitro, C1-C6 alkyl, C1-C6 alkoxy, Ci-C6 haloalkyl, Ci-C6 haloalkoxy, C1-C6 alkylthio or
- -
(Ci-Ce alkyl) sulfonyl, preferably represents phenyl-Ci-C6 alkyl optionally substituted with halogen, nitro, cyano, Ci-C6 alkyl, Ci-C6 alkoxy, haloalkyl x-6 or Ci-C6 haloalkoxy, preferably represents hetaryl of or 6 members
(for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl) optionally substituted with halogen or Ci-C6 alkyl, preferably represents phenoxy-Ci-C6 alkyl optionally substituted by halogen or Ci-C6 alkyl or preferably represents hetaryloxy-Ci- C6 of 5 or 6 members (for example pyridyloxy-C! -C6alkyl, pyrimidyloxy-Ci-C6alkyl or thiazolyloxy-Ci-C6alkyl) optionally substituted by halogen, amino or Ci-C6alkyl, R2 preferably represents C1-C20alkyl alkenyl
C2-C20 (Ci-C8 alkoxy) C2-Ca alkyl, (Ci-Ca polyalkoxy) C2-C8 alkyl, each optionally substituted with halogen, preferably represents C3-C8 cycloalkyl optionally substituted with halogen, Ci-C6 alkyl or alkoxy Ci-C6 or preferably represents phenyl or benzyl in each case optionally substituted with halogen, cyano, nitro, Ci-C6 alkyl, Ci-C6 alkoxy, C6-C6 haloalkyl or Ci-C6 haloalkoxy, R3 preferably represents i-C8 alkyl optionally substituted with halogen or represents phenyl or
- - benzyl in each case optionally substituted by halogen, d-C6 alkyl, Ci-C6 alkoxy, haloalkyl C1-C, haloalkoxy Ci-C, cyano or nitro, R4 and R5 independently of each other preferably represent Ci-C8 alkyl , alkoxy CL-CB, Ci-C8 alkylamino, di- (Ci-C8 alkyl) amino, Ci-C8 alkylthio, C2-C8 alkenylthio, C3-C7 cycloalkylthio in each case optionally substituted with halogen or represent phenyl, phenoxy or phenylthio in each case optionally substituted with halogen, nitro, cyano, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, Ci-C4 alkyl or Ci-C4 haloalkyl, R6 and R7 independently of one another preferably represent hydrogen, represent C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyl, C 1 -C 8 alkoxy C 1 -C 8 alkyl optionally substituted with halogen, represent phenyl optionally substituted with halogen, haloalkyl Cx-Cs, Ci-C8 alkyl or Ci-C8 alkoxy, benzyl optionally and substituted with halogen, Cx-Cs alkyl, Ci-C8 haloalkyl or Ci-C8 alkoxy or together represent a C3-C6 alkylene radical optionally substituted with Ci-C4 alkyl wherein optionally a carbon atom is substituted with oxygen or sulfur, R13 preferably represents hydrogen, preferably represents Ci-C8 alkyl or Ci-C8 alkoxy at each
- - optionally substituted with halogen, represents C3-C8 cycloalkyl optionally substituted by halogen, Ci-C4 alkyl or Ci-C4 alkoxy in which optionally a methylene group is replaced by oxygen or sulfur, or represents phenyl, phenyl-C1-6alkyl C4 or phenyl-C 1 -C 4 alkoxy each optionally substituted by halogen, Ci-C6 alkyl, Ci-Ce alkoxy, Ci-C4 haloalkyl, Ci-C4 haloalkoxy, nitro or cyano, Ri preferably represents hydrogen or Ci-C8 alkyl or R13 and R14a together preferably represent alkanediyl
C-C6, R1 a and R1Sa are identical or different and preferably represent Ci-C6 alkyl or R15a and R16a together preferably represent a C2-C4 alkanediyl radical which is optionally substituted with Ci-C6 alkyl, Ci-C6 haloalkyl or by optionally substituted phenyl with halogen, Ci-C6 alkyl, haloalkyl CÍ-CJ, Ci-C6 alkoxy, Cx-C4 haloalkoxy, nitro or cyano, R17a and R18a independently of one another preferably represent hydrogen, represent Ci-C8 alkyl optionally substituted with halogen or represent phenyl optionally substituted with halogen, Ci-C6 alkyl, Ci-Cg alkoxy, Cx-C4 haloalkyl, haloalkoxy C, LC, nitro or cyano or R17a and R18a together with the carbon atom to which they are attached preferably represent a carbonyl group or
- - represent C5-C7 cycloalkyl optionally substituted with halogen, C1-C4 alkyl or Ci-C4 alkoxy in which optionally a methylene group is replaced by oxygen or sulfur, R19a and R20a independently of one another preferably represent C1-C10 alkyl, C2-Ci0 alkenyl, C1-C10 alkoxy, C1-C10 alkylamino, C3-C10 alkenylamino, di- (Ci-Ci0 alkylamino) or di- (C3-C10 alkenyl) amino. In the definitions of the radicals mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. J particularly preferably represents C3-C6 cycloalkyl which is optionally interrupted by an oxygen atom and is optionally monosubstituted or disubstituted with fluorine, chlorine, Ci-C4 alkyl, C3-C6 cycloalkyl, Ci-C4 alkoxy or Ci-C2 haloalkyl, X is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, Ci-C4 alkyl, trifluoromethyl, C1-C4 alkoxy, difluoromethoxy or trifluoromethoxy, and is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, alkyl Ci-C4, trifluoromethyl, C1-C4 alkoxy, difluoromethoxy or trifluoromethoxy, particularly preferably represents a number 1 or 2
- - with the proviso that at least one of the radicals J, X or Y is located at the 2-position of the phenyl radical and is not hydrogen, CKE particularly preferably represents one of the groups
- -
A particularly preferably represents hydrogen, represents Ci-C6 alkyl, (C1-C4 alkoxy) Ci-C2 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine or chlorine, represents C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with Ci-C2 alkyl or Cx-C2 alkoxy or (but not in the case of the compounds of formulas (1-3), (1-4), (1-6) and (1-7)) represents phenyl or benzyl, each of which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, Ci-C4 alkyl, haloalkyl Cx-C2, alkoxy C1-C4, haloalkoxy C! -C2, cyano or nitro, B in particular preferable represents hydrogen, C1-C4 alkyl or (C1-C2 alkoxy) C1-C2 alkyl or A, B and the carbon atom to which they are particularly preferably attached represent saturated or unsaturated C5-C cycloalkyl in which optionally a member of the ring is replaced by oxygen or sulfur and that is optionally monosubstituted or disubstituted with Ci-C6 alkyl, trifluoromethyl, Ci-C6 alkoxy or (C1-C3 alkoxy) C1-C3 alkoxy, with the proviso that in this case Q3 is particularly preferably hydrogen or methyl or A, B and the atom of carbon to which they are particularly preferably attached represent C5-C6 cycloalkyl which is substituted with an alkylene dicalcyl group or by an alkylenedioxyl group or by an alkylene dithiol group
- - optionally contains one or two oxygen or sulfur atoms not directly adjacent and which is optionally substituted with methyl or ethyl, which group together with the carbon atom to which it is attached, forms an additional five or six member ring, with the condition that Q3 in this case particularly preferably represents hydrogen or methyl, or A, B and the carbon atom to which they are particularly preferably attached represent C3-C6 cycloalkyl or C5-C6 cycloalkenyl in which two substituents together with the carbon atoms to which they are attached in each case represent C2-C4 alkanediyl, C2-C4 alkenediyl or butadye-diyl optionally substituted by Ci-C2 alkyl or C, L-C2 alkoxy; with the proviso that Q3 in this case particularly preferably represents hydrogen or methyl, D represents hydrogen, represents Ci-C6 alkyl, C3-C6 alkenyl, (C1-C4 alkoxy) C2-C3 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, represents C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with C 1 -C 4 alkyl, C 1 -C 4 alkoxy or Ci-C 2 haloalkyl in which optionally a methylene group is replaced by oxygen or (but not in the case of the compounds of the formula (1-1)) represents phenyl or pyridyl, each of which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, Ci-C4 alkyl (haloalkyl Cx-C ^, alkoxy C1 -C4 or C1-C4 haloalkoxy, or
- -
A and D together particularly preferably represent C3-C5 alkanediyl optionally monosubstituted or disubstituted wherein a methylene group may be substituted with a carbonyl group (but not in the case of the compounds of the formula (1-1)), oxygen or sulfur, the possible substituents being Ci-C2 alkyl or C1.-C2 alkoxy, or A and D (in the case of the compounds of the formula (1-1)) together with the atoms to which they are attached represent one of Groups AD-1 to AD-10:
AD-1 AD-2 AD-3
AD-4 AD-5 AD-6
AD-7 AD-8 AD-9
- -
AD-10 or A and Q1 together particularly preferably represent C3-C4 alkanediyl which is in each case optionally monosubstituted or disubstituted with identical or different substituents which are selected from the group consisting of Ci-C2 alkyl and Ci-C2 alkoxy or D and Q1 together particularly preferably represent C3-C4 alkanediyl which is optionally interrupted by an oxygen atom, or Q1, particularly preferably represents hydrogen, Ci-C4 alkyl, Ci-C4 alkoxy Ci-C2 alkyl or C3-C6 cycloalkyl optionally substituted by methyl or methoxy in which optionally a methylene group is replaced by oxygen, Q2 of particularly preferably it represents hydrogen, methyl or ethyl, Q4 Q5 and Q6 independently of one another, particularly preferably they represent hydrogen or C1-C3 alkyl, Q3, particularly preferably represents
- - hydrogen, Ci-C4 alkyl, or C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with methyl or methoxy, Q1 and Q2 together with the carbon to which they are particularly preferably attached represent saturated C5-C6 cycloalkyl optionally substituted with alkyl C1-C4 or C1-C4 alkoxy wherein optionally a ring member is replaced by oxygen, or Q3 and Q4 together with the carbon to which they are particularly preferably attached represent a saturated C5-C6 ring optionally substituted with C1-6alkyl C2 or C1-C2 alkoxy in which optionally a ring member is replaced by oxygen or sulfur, with the proviso that in this case A particularly preferably represents hydrogen or methyl, G particularly preferably represents hydrogen (a) or represents one of the groups
OL R4 ^ R1 (b), M - R2 (C), / SC "R3 (d), - - r5 (e) ^ R6 E (f) or - N (g in particular (a), (b), (c) or (g) LR in which E represents a metal ion equivalent or an ammonium ion,
- -
L represents oxygen or sulfur M represents oxygen or sulfur, R1 particularly preferably represents Ci-C8 alkyl, C2-C18 alkenyl, (Ci-C4 alkoxy) C2-6 alkyl, (Ci-C4 alkylthio) C-alkyl; L-C2, each of which is optionally monosubstituted to trisubstituted with fluorine or chlorine, or C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, Ci-C2 alkyl or Ci-C2 alkoxy and in which optionally one or two not directly adjacent ring members are substituted by oxygen, particularly preferably represents phenyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, cyano, nitro, C1-C4 alkyl, C1-C4 alkoxy, haloalkyl, C2 or C1-C2 haloalkoxy, R2, particularly preferably represents Ci-C8 alkyl, C2-C8 alkenyl or (C1-C4 alkoxy) C2-C alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, particularly preferred rible represents C3-C3 cycloalkyl which is optionally monosubstituted with Ci-C2 alkyl or Cx-C2 alkoxy or particularly preferably represents phenyl or benzyl, each of which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, cyano,
- - nitro, C 1 -C 4 alkyl, C 1 -C 3 alkoxy, trifluoromethyl or trifluoromethoxy, R 3 is particularly preferably C alquilo-CÉ alkyl which is optionally mono-substituted to trisubstituted with fluorine or represents phenyl which is optionally monosubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R 4 is particularly preferably C 1 -C 6 alkyl, alkoxy i 5, alkylamino C x -Cg, di- (Ci alkyl) -C6) amino, Cilt-C6 alkylthio, C3-C4 alkenylthio, C3-C6 cycloalkylthio or represents phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with fluorine, chlorine, bromine, nitro, cyano, C1-6 alkoxy C3, C1-C3 haloalkoxy, C1-C3 alkylthio, haloalkylthio CJ.-C3, C1-C3 alkyl or trifluoromethyl, R5, particularly preferably represents Ci-C6 alkoxy or Ci-C6 alkylthio, Rs is particularly preferably hydrogen, Ci-C6 alkyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, al C3-C6 quenyl, (Ci-C6 alkoxy) C1-C4 alkyl, represents phenyl which is optionally monosubstituted with fluorine, chlorine, bromine, trifluoromethyl, C1-C4 alkyl or C1-C4 alkoxy, represents benzyl which is optionally monosubstituted with fluorine, chlorine, bromine, C1-C4 alkyl, trifluoromethyl or C1-C4 alkoxy, R7 is particularly preferably represented
- - Ci-C6 alkyl, C3-C6 alkenyl or (C-C6 alkoxy) Ci-C4 alkyl, R6 and R7 together particularly preferably represent a C4_C5 alkylene radical which is optionally substituted with methyl or ethyl and in which optionally A methylene group is replaced by oxygen or sulfur. The definitions of radicals that are mentioned as being particularly preferred, halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine. J very particularly preferably represents cyclopl, dicyclopl, cyclobutyl, cyclopentyl, cyclohexyl, oxetanyl, tetrahydrofurfuryl, tetrahydranyl, X very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, pl, methoxy or ethoxy, and very particularly preferably represents hydrogen, chlorine, bromine, methyl, ethyl, pl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, very particularly preferably represents the number 1 or 2, with the proviso that at least one of the radicals J , X or Y is located at the 2-position of the phenyl radical and is not hydrogen. Here, the radicals J, X and Y that have their preferred meanings in a very particular way, are arranged in a very
- - particularly preferable in the following phenyl substitution patterns
(H) Y † H O Y | H (J) Y † H
(K) Y = H (L)? =? where only in the substitution patterns of the phenyl (B), (K) and (L), X can also represent hydrogen, CKE very particularly preferably represents
- - one of the groups
A very particularly preferably represents hydrogen, represents Ci-C4 alkyl or (Ci-C2 alkoxy) Ci-C2 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, represents cyclopropyl, cyclopentyl or cyclohexyl and, only in in case of
the compounds of the formula (1-5) represents phenyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, form B very particularly preferably represents hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are bonded very particularly preferably represent saturated C5-Cg cycloalkyl in which optionally a ring member is replaced by oxygen or sulfur and which is optionally monosubstituted with methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy, methoxyethoxy, butoxy, methoxymethyl or ethoxyethoxy, with the proviso that in this case Q3 very particularly preferably represents hydrogen, or A, B and the carbon atom to which they are bonded very particularly preferably represents C6 cycloalkyl which is optionally substituted with an alkylenedioxyl group which is n has two oxygen atoms not directly adjacent, with the proviso that in this case Q3 very particularly preferably represents hydrogen, or A, B and the carbon atom to which they are bonded very particularly preferably represent cycloalkyl C5-CG or C5-C6 cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent
- - C2-C alkanediyl or C2-C4 alkenediyl or butadiene-diol, with the proviso that in this case Q3 very particularly preferably represents hydrogen, D very particularly preferably represents hydrogen, represents CX-C4 alkyl, C3-C4 alkenyl , (C 1 -C 4 alkoxy) C 2 -C 3 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, represents cyclopropyl, cyclopentyl or cyclohexyl or (but not in the case of the compounds of the formula (1-1) ) represents phenyl or pyridyl, each of which is optionally monosubstituted with fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or trifluoromethyl, or A and D together very particularly preferably represent C3-C5 alkanediyl which is optionally monosubstituted with methyl or methoxy and in which optionally a carbon atom is substituted with oxygen or sulfur or represents the group AD-1, A and Q1 together very particularly preferably they represent C3-C4 alkanediyl which is optionally monosubstituted or disubstituted with methyl or methoxy or D and Q1 together very particularly preferably represent C3-C4 alkanediyl, Q1 very particularly preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl ,
- - cyclopentyl or cyclohexyl, Q2 very particularly preferably represents hydrogen or methyl, Q4, Q5 and Q6 independently of one another, very particularly preferably represent hydrogen or methyl, Q3 very particularly preferably represents hydrogen, methyl, ethyl or propyl, or Q1 and Q2 together with the carbon to which they are bonded very particularly preferably represent saturated C5-C6 cycloalkyl which is optionally substituted with methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or butoxy and in which optionally a ring member is replaced by oxygen, or Q3 and Q4 together with the carbon to which they are attached very particularly preferably represent a saturated C5-C6 ring that is optionally monosubstituted with methyl or methoxy, with the proviso that in this Case A very particularly preferably represents hydrogen, G very particularly preferably represents hydrogen no (a) or represents one of the groups
-S02-R3 (d)
- - in which L represents oxygen or sulfur, M represents oxygen or sulfur and E represents an ammonium ion R1 very particularly preferably represents Cx-Cg alkyl, C2-Ci7 alkenyl, (Ci-C2 alkoxy) -alkyl d, ( alkylthio C, L-C2) alkyl CLF each of which is optionally monosubstituted with chlorine, or represents cyclopropyl or cyclohexyl, each of which is optionally monosubstituted with fluorine, chlorine, methyl or methoxy, very particularly preferably represents phenyl which is optionally monosubstituted with fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R2 very particularly preferably represents Ci-C8 alkyl, C2-C6 alkenyl or (Ci-C4 alkoxy) C2-C3 alkyl , each of which is optionally monosubstituted with fluorine, or represents phenyl or benzyl, R3 very particularly preferably represents Ci-C8 alkyl. J most preferably represents cyclopropyl, X most preferably represents chloro, methyl or ethyl, and most preferably represents chloro, methyl,
- - ethyl or hydrogen, m most preferably represents the number 1 or 2, with the proviso that at least one of the radicals J,
X or Y is located at the 2-position of the phenyl radical and is not hydrogen. Here, the radicals J, X and Y which have their most preferred meanings, are particularly preferably arranged in the following phenyl substitution patterns.
(E) Y † H (H) Y † H (K) Y = H (L) Y = H
CKE most preferably represents one of the groups
Most preferably it represents Ci-C4 alkyl or cyclopropyl, B most preferably represents hydrogen or methyl
- or A, B and the carbon atom to which they are attached most preferably represent saturated C5-Ce cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted with methoxy, ethoxy, butoxy or methoxymethyl, A, B and the carbon atom to which they are attached most preferably represent C6 cycloalkyl which is optionally substituted with a C2-C3 alkylenedioxy group having two oxygen atoms not directly adjacent, D most preferably represents hydrogen or A and D together more preferably represent C3-C5 alkanediyl, A and Q1 together most preferably represent C3-C4 alkanediyl, most preferably represents hydrogen, G most preferably represents hydrogen (a) or represents one of the groups
it most preferably represents C-C6 alkyl or represents phenyl which is monosubstituted with chlorine, most preferably represents Ci-C8 alkyl, most preferably represents Ci-Ca alkyl.
The definitions or illustrations of general or preferred radicals given above may be combined with each other as desired, ie including combinations between respective ranges and preferred ranges. They apply both to final products and, correspondingly, to precursors and intermediates. According to the invention preference is given to the compounds of the formula (I) which contain a combination of the meanings that are previously offered as preferred (preferable). According to the invention, particular preference is given to the compounds of the formula (I) which contain a combination of the meanings given above as being particularly preferred. According to the invention, very particular preference is given to the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. According to the invention, preference is given to the compounds of the formula (I) which contain a combination of the meanings given above as being more preferred. The saturated or unsaturated hydrocarbon radicals, such as alkyl, alkanediyl or alkenyl, in each case can be straight or branched chain whenever this is possible,
including the combination with heteroatoms, such as, for example, in alkoxy. Unless otherwise indicated, the optionally substituted radicals may be monosubstituted or polysubstituted, where in the case of polysubstitution the substituents may be identical or different. In addition to the compounds mentioned in the preparation examples, mention may be made of the following compounds of the formula (I-1-a):
Table 1: J = 2 - [> -; X = H; Y = H.
- -
- -
- -
- -
- -
Table 2: A, B and D as reflected in Table 1
J = 2 > - X = 4-CH3; Y = H Table 3: A, B and D as reflected in Table 1
J: = 2 > ~; = 6- CH3; Y = H. Table 4: A, B and D as reflected in Table 1
J: = 2 - D > - X = 6-C2H5; Y = H. Table 5: A, B and D as reflected in Table 1
X: = 2-CH3; Y = H; J = = 5 - -; Table 6: A, B and D as reflected in Table 1
X: = 2-CH3; Y - 4-CH3, r J = 5 - [> -; Table 7: A, B and D as reflected in Table 1
J = = 2 | > ~; X = = 4 -CH3; Y = 6-CH3. Table 8: A, B and D as reflected in Table 1
J: = 2 | "O"; X: = 6 -C2H5; Y = 4-CH3. Table 9: A, B and D as reflected in Table 1
J: = 2 | - -; = = 6 -CH3; Y = 4-Cl. Table 10: A, B and D as reflected in Table 1
J = = 2 - -; X = = 6 -C2H5; Y = 4-Cl.
- -
Table 11: A, B and D as reflected in Table 1
J = - _; = 6-Cl; Y = 4-CH3. Table 12: A, B and D as reflected in Table 1
J = 2 - O-; X = 5-CH3; Y = 4-CH3. Table 13: A, B and D as reflected in Table 1
X = 2-CH3; J = 4 - "&; -; Y = H. Table 14: A, B, and D as reflected in Table 1
X = 2 - C2H5; J = 4 - [> -; Y = H. Table 15: A, B and D as reflected in Table 1
X = 2-CH3; J = 4 - Y = 6-CH 3 · Table 16: A, B and D as reflected in Table 1
X = 2 - C2H5; J = 4 - [> -; Y = 6- CH3. Table 17: A, B and D as reflected in Table 1
X = 2-| C2H 5 '' J = 4-O-; Y = 6-C2H5. Table 18: A, B and D as reflected in Table 1
X = 2-C1; J = - 4 - > - - Y = 6-CH3. Table 19: A, B and D as reflected in Table 1
X = 2-C1; J = = 4 - O-; Y = 6-C2H5 Table 20: A, B and D as reflected in Table 1
X = 2-CH3; J = 4 -| 'Y = 5-CH3 Table 21: A, B and D as reflected in Table 1
X = 2-CH3; J = 3 - "[- '' Y = 6-CH3
Table 22: A, B and D as reflected in Table 1
J = 2 - [> -; X = 5 - CH3; Y = H. Table 22a: A and B as reflected in Table J = 2-O-; X = 5- O-; Y = H.
Table 23 J = 2 - [> -; X = H; Y = H.
-
AB-CH2-CHOCH3- (CH2) 3- -CH2-CHOC2H5- (CH2) 3 -CH2-CHOC3H7- (CH2) 3 - -CH2-CHOC4H9- (CH2) 3 -CH2-CHO- (CH2) 2-OCH3 - (CH2) 3- -CH2-CH- (CH2) 3- ° x? - (CH2) 2 - CHCH3 - (CH2) 2 - - (CH2) 2-CHC2H5- (CH2) 2- - (CH2) 2-CHC3H7- (CH2) 2- - (CH2) 2-CHi-C3H7- ( CH2) 2- - (CH2) 2-CHOCH3- (CH2) 2 ~
- (CH2) 2- HOC2H5- (CH2) 2- - (CH2) 2-CHOC3H7- (CH2) 2- - (CH2) 2-CHO-i-C3H7- (CH2) 2- - (CH2) 2-C (CH3) 2- (CH2) 2- CH2 - (CHCH3) 2 - (H2) 2"-CH2-CH- (CH2) 2-CH CH2
- -
- -
- -
Table 24: A and B as reflected in Ta
J = 2 -0- '· X-4-CH3; Y = H Table 25: A and B as reflected in the Table
J = 2 - [-; X = 6- CH3; Y = H Table 26: A and B as reflected in the Table
J = 2 - X = 6-C2H5; Y = H Table 27: A and B as reflected in the Table
X = 2 - CH3; Y = H; J = 5 - > - ·
Table 28: A and B as reflected in the Table
X = 2 - CH3; Y = 4-CH3; J = 5 - > -.
Table 29: A and B as reflected in the Table
J - 2 - t > -; X = 4-CH3; Y = 6-CH3.
- -
Table 30: A and B as reflected in Table 23
J = 2 - [> -; X = 6-C2H5; Y = 4-CH3. Table 31: A and B as reflected in Table 23
J = 2 - O -; X = 6-CH3; Y = 4-C1. Table 32: A and B as reflected in Table 23
J = 2 - O -; X = 6-C2H5; Y = 4-C1. Table 33: A and B as reflected in Table 23
J = 2 - > -; X = 6-C1; Y = 4-CH3. Table 3: A and B as reflected in Table 23
J = 2 - [> -; X = 5-CH3; Y = 4-CH3. Table 35: A and B as reflected in Table 23
X = 2-CH3; J = 4 - O -; Y = H. Table 36: A and B as reflected in Table 23 X = 2-C2H5; J = 4 - O -; Y = H. Table 37: A and B as reflected in Table 23
X = 2-CH3; J = 4 - t > -; Y = 6-CH3. Table 38: A and B as reflected in Table 23 X = 2-C2H5; J = 4 - [> -; Y = 6- CH3. Table 39: A and B as reflected in Table 23 X = 2-C2H5; J = 4 - [> -; Y = 6-C2H5. Table 40: A and B as reflected in Table 23 X = 2-C1; J = 4 - [> -; Y = 6-CH3.
- -
Table 41: A and B as reflected in Table 23 X = 2-C1; J = 4 - O-; Y = 6-C2H5. Table 42 A and B as reflected in Table 23 X = 2-CH 3; J = 4 - >; Y = 5 - CH3. Table 43 A and B as reflected in Table 23 X = 2-CH3; J = 3 - > -; Y = 6- CH3. Table 44 A and B as reflected in Table 23 J 2 -O-; X = 5-CH3; Y = H Table 45 A and B as reflected in Table 23 J = 2 - -; X = 5- -; Y = H.
Table 46: J = - > -; x = H; Y = H.
A D
CH 3 CH 3 CH 3 - (CH 2) 2 OH CH 3 - (CH 2) 2 OCH 3 CH 3 - (CH 2) 2-0- (CH 2 2 -OCH 3
- (CH2) 2 -0-CH3 - (CH2) 2-0-CH3 - (CH2) 2 -0- (CH2) 2-OCH3 - (CH2) 2-0- (CH2) 2-OCH3
- -
- -
Table 47: A and D as reflected in Table J = 2 - X = 4-CH3; Y = H Table 48: A and D as reflected in Table 46
J = 2 > ~! X = 6- CH3; Y = H. Table 49: A and D as reflected in Table 46
J = 2 - X = 6-C2H 5 '"Y = H. Table 50: A and D as reflected in Table 46
X = 2- CH3; Y = H; J = 5 - > -: Table 51: A and D as reflected in Table 46
X = 2- CH3; Y = 4-CH3; J = 5 - ^; Table 52: A and D as reflected in Table 46
J = 2 - -; X = = 4-CH3; Y = 6-CH3.
Table 53: A and D as reflected in Table 46
- -
J = 2 - X = 6-C2H5; Y = 4-CH3.
Table 54: A and D as reflected in Table 46
J = 2 - [-; X = 6-CH3; Y = 4-C1. Table 55: A and D as shown in Table 46
J = 2 - X = 6-C2H5; Y = 4-C1.
Table 56: A and D as reflected in Table 46
J = 2 - -; X = 6-C1; Y = 4-CH3. Table 57: A and D as reflected in Table 46 J = 2 - ^; X = 5-CH3; Y = 4-CH3.
Table 58: A and D as reflected in Table 46
X = 2 - CH3; J = 4 | - Y = H. Table 59: A and D as reflected in Table 46
X = 2-| C2H5; j = Y = H. Table 60: A and D as reflected in Table 46
X = 2-| CH3; J = 4 · - · Y = 6-CH3.
Table 61: A and D as reflected in Table 46
X = 2- C2H5; j - 4 - [> - Y = 6- CH3. Table 62: A and D as reflected in Table 46
X = 2- C2H5; j = 4 - -; = 6-C2H5. Table 63: A and D as reflected in Table 46
X = 2- Cl; J = 4 - = 6-CH3. Table 64: A and D as reflected in Table 46
- -
X = 2-C1; J = 4 - [> -; Y = 6-C2H5. Table 65: A and D as reflected in Table 46 X = 2-CH3; J = 4-0-; Y = 5-CH3. Table 66: A and D as reflected in Table 46 X = 2-CH3; J = 3 - [-; Y = 6-CH3. Table 67: A and D as reflected in Table 46 J = 2 - [> -; X = 5-CH3; Y = H. Table 68: A and D as reflected in Table 46 J = 2 - £ > -; X 5- -; Y = H. The preferred definitions of the groups listed above relating to the compound to improve the compatibility of the crop plants ("safeners against herbicides") of the formulas (Ha), (Ilb), (lie), (lid) ) and (He) are defined later. mpreferably represents the numbers 0, 1, 2, 3 or 4. A1 preferably represents one of the divalent heterocyclic groups shown below
Preferably represents the numbers 0, 1, 2, 3 or 4. A2 preferably represents methylene or ethylene in each case optionally substituted with methyl, ethyl,
- - methoxycarbonyl or ethoxycarbonyl. R14 preferably represents hydroxyl, mercapto, amino, 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, dimethylamino or diethylamino. R15 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, non-propoxy, n, i, t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyletoxy, methylthio, ethylthio, non-propylthio, n, i, t-butylthio, methylamino, ethylamino, non-propylamino, n, i, t-butylamino, dimethylamino or. diethylamine. R16 preferably represents in each case methylene or ethylene optionally substituted with fluorine, chlorine and / or bromine. R17 preferably represents hydrogen, methyl, ethyl, non-i-propyl, n, i, t-butyl, propenyl, butenyl, propinyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl. in each case optionally substituted with fluorine and / or chlorine, or phenyl optionally substituted with fluorine, chlorine, methyl, ethyl, non-propyl, n, i, t-butyl. R18 preferably represents hydrogen, methyl, ethyl, n-i-propyl, n, i, s or t-butyl, propenyl, butenyl, propinyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl,
- - piperidinyl in each case optionally substituted with fluorine and / or chlorine, or phenyl optionally substituted with fluorine, chlorine, methyl, ethyl, non-i-propyl, n, i, t-butyl, or together with R17 represents one of the radicals -CH2-O- (. ¾ - (- ¾- and -CH2-CH2-O-CH2-CH2-) which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, they form a 5- or 6-membered carbocycle R19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents methyl, ethyl, non-propyl, cyclopropyl, cyclobutyl, cyclopentyl , cyclohexyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine.
R 20 preferably represents hydrogen, methyl, ethyl, n-or i-propyl, n, i, s or t-butyl optionally substituted with hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n or i-propoxy. R21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents methyl, ethyl, non-propyl, n, i, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl each optionally substituted with fluorine, chlorine and / or bromine. X1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i-, t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, no. -
- - propoxy, difluoromethoxy or trifluoromethoxy. X2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i, t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, i-propoxy, difluoromethoxy or trifluoromethoxy.
X3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i, t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, i-propoxy, difluoromethoxy or trifluoromethoxy. t preferably represents the numbers 0, 1, 2, 3 or 4. v preferably represents the numbers 0, 1, 2 or 3. R22preferably represents hydrogen, methyl, ethyl, n or i-propyl. R 23 preferably represents hydrogen, methyl, ethyl, n or i-propyl. R24 preferably represents hydrogen, methyl, ethyl, non-propyl, n, i, t-butyl, methoxy, ethoxy, non-propoxy, n, i, t-butoxy, methylthio, ethylthio, non-propylthio, n, i, t-butylthio, methylamino, ethylamino, n-i-propylamino, n, i, t-butylamino, dimethylamino or diethylamino in each case optionally substituted with cyano, fluorine, chlorine, methoxy-, ethoxy, not i- propoxy, or cyclopropyl, cyclobutyl, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,
- cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutyl-amino, cyclopentylamino or cyclohexylamino in each case optionally substituted with cyano, fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl. R 25 preferably represents hydrogen, methyl, ethyl, non-i-propyl, n, io-s-butyl in each case optionally substituted with cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, non-propoxy, propenyl, butenyl, propinyl or butynyl in each case optionally substituted with cyano, fluorine, chlorine or bromine, or methyl, ethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted with cyano, fluoro, chloro, bromo. R 26 preferably represents hydrogen, methyl, ethyl, non-i-propyl, n, io-s-butyl in each case optionally substituted with cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, non-propoxy, propenyl, butenyl, propinyl or butynyl in each case optionally substituted with cyano, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl each optionally substituted with cyano, fluorine, chlorine, bromine, methyl, ethyl, non-i-propyl, or phenyl optionally substituted with nitro , cyano, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i, t-butyl, trifluoromethyl, methoxy, ethoxy, i-propoxy, difluoromethoxy or trifluoromethoxy, or together with R25 represents butan- 1 , 4 -diyl (trimethylene),
- pentan-1, 5-diyl, 1-oxabutan-1, 4-diyl or 3-oxapentan-1, 5-diyl in each case optionally substituted with methyl or ethyl. X4 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i, t-butyl, trifluoromethyl, methoxy, ethoxy, i-propoxy, difluoromethoxy or trifluoromethoxy. X5 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, non-propyl, n, i, t-butyl, trifluoromethyl, methoxy, ethoxy., no i-propoxy, difluoromethoxy or trifluoromethoxy. Examples of the compounds of the formula (lia) which are very particularly preferred as safeners against herbicides according to the invention are listed in the following table.
Table Examples of the compounds of the formula
(He has)
- -
-
- -
Examples of the compounds of the formula (Ilb) which are very particularly preferred as safeners against herbicides according to the invention are listed in the following table.
- -
Table Examples of the compounds of the formula
examples of the compounds of the formula (lie) that
- - very particular preference as safeners against herbicides according to the invention are listed in the following table.
Table Examples of the compounds of the formula
- -
Examples of the compounds of the formula (lid) which are particularly preferred as safeners against herbicides according to the invention are listed in the following table.
Table Examples of the compounds of the formula
- -
- -
- -
Examples of the compounds of the formula (lie) which are particularly preferred as safeners against herbicides according to the invention are listed in the following table.
Table Examples of the compounds of the formula
- -
Most preferred as a compound for improving the compatibility of crop plants [component (b ')] are cloquintocet-methyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, phenchlorim, cumyluron, dymron, dimethoperate and compounds IIe. -5 and IIe-11, and emphasizes
- - particularly cloquintocet-methyl and mefenpyr-diethyl. The compounds of the general formula (lia) to be used as safeners according to the invention are known and / or can be prepared by methods known per se (see WO-A-91/07874, WO-A-95/07897) . The compounds of the general formula (Ilb) to be used as safeners according to the invention are known and / or can be prepared by methods known per se (see EP-A-191736). The compounds of the general formula (lie) to be used as safeners according to the invention are known and / or can be prepared by methods known per se (see DE-A-2218097, DE-A-2350547). The compounds of the general formula (lid) to be used as safeners according to the invention are known and / or can be prepared by methods known per se (see DE-A-19621522 / US-A-6235680). The compounds of the general formula (He) to be used as safeners according to the invention are known and can be prepared by methods known per se (see WO-A-99/66795 / US-A-6251827). Examples of the combinations of selective herbicides according to the invention comprising in each case an active compound of the formula (I) and one of the safeners defined above are listed in the following table.
- - Table Examples of the combinations according to the invention
- -
- -
- -
It has now surprisingly been found that the combinations of active compounds of cyclic ketoenols substituted with cycloalkylphenyls of the general formula (I) defined above and the safeners (antidotes) from the group (b ') described above combine a very good tolerance of plants with a particularly high herbicidal activity and can be used in various crops, particularly in cereals (especially wheat), but also in soybeans, potatoes, corn and rice, for the selective control of weeds. In this context it is considered surprising that, from a multiplicity of known safeners or antidotes capable of acting as antagonists of the harmful effect of a herbicide on the crop plants, specifically those compounds of group (b ') described above are those which are suitable to compensate - almost completely - the harmful effect of the cyclic ketoenols substituted with cycloalkylphenyls on the crop plants, without at the same time having any adverse adverse effect on the herbicidal activity against the weeds.
Here, the particularly advantageous effect of the pairs of particularly preferred and most preferred combinations of the group (b ') can be emphasized, particularly with respect to the gentle treatment of cereal plants, such as wheat, barley and rye, for example , but also corn and rice, as crop plants. Bibliography descriptions have already been provided on the effect that the activity of various compounds can be increased by the addition of ammonium salts. The salts in question, however, are salts with a detergent effect (for example WO 95/017817) and / or salts having relatively long alkyl and / or aryl substituents, which have a permeabilizing effect or which increase the solubility of the active compound (for example EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, US 4 844 734, US 5 462 912, US 5 538 937, US-A 03/0224939, US-A 05/0009880, US-A 05/0096386). In addition, the prior art describes the activity only for certain active compounds and / or certain applications of the composition in question. In still other cases, they are salts of sulphonic acids in which the acids on the other hand have a paralyzing action on the insects (US 2 842 476). An increase in activity is described, for example, by means of ammonium sulphate for glyphosate and phosphinothricin herbicides (US 6 645 914, EP-A2 0 036 106). However, this prior technique neither
describes or suggests a corresponding activity for insecticides. Also, the use of ammonium sulfate as a formulation aid for certain active compounds and applications has been described (WO 92/16108), but is used here in order to stabilize the formulation, not to increase the activity. It has now been found, quite surprisingly, that the activity of insecticides and / or acaricides and / or herbicides of the class of spirocyclic ketoenols substituted with cycloalkylphenyl can be significantly increased through the addition of ammonium salts or phosphonium salts to the use solution or through the incorporation of these salts into a formulation comprising cyclic ketoenols substituted with cycloalkylphenyls. Accordingly, the present invention provides the use of ammonium salts or phosphonium salts to increase the activity of compositions for the protection of crops comprising cyclic ketoenols substituted with active cycloalkylphenyls as insecticides and / or acaricides as the active compound. The invention also provides compositions comprising cyclic ketoenols substituted with active cycloalkylphenyls as insecticides and ammonium salts or phosphonium salts that increase activity, which specifically include not only the active compounds
- - formulated if not also ready-to-use compositions (spray liquids). Finally, the invention also provides the use of these compositions for controlling harmful insects and / or acarids and / or unwanted vegetation. The compounds of the formula (I) have a broad insecticidal and / or acaricidal and / or herbicidal action; however, in specific cases the activity and / or compatibility with the crops is not satisfactory. The active compounds can be used in the compositions according to the invention in a wide concentration range. Here, the concentration of the active compounds of the formulation is usually 0.1-50% by weight. The ammonium salts and the phosphonium salts which, according to the invention, increase the activity of the compositions for the protection of crops comprising inhibitors of fatty acid biosynthesis are defined by the formula (???)
wherein D represents nitrogen or phosphorus, D preferably represents nitrogen,
R26 ', R27, R28 and R29 independently of one another represent hydrogen or Ci-C8 alkyl in each case optionally substituted or Ci-C8 alkylene monounsaturated or polyunsaturated, optionally substituted, wherein the substituents may be selected from the group consisting of halogen, nitro and cyano, R26 ', R27, R28 and R29 preferably independently from each other represent hydrogen or optionally substituted Ci-C4 alkyl, wherein the substituents can be selected from the group consisting of halogen, nitro and cyano, R26 ', R27, R28 and R29, particularly preferably independently of one another, representing hydrogen, ml, l, n-propyl, isopropyl, n-butyl , isobutyl, s-butyl or t-butyl, R26 ', R27, R28 and R29 very particularly preferably represent hydrogen, n represents 1, 2, 3 or 4, n preferably represents 1 or 2, R30 represents an inorganic anion or organic, R30 preferably represents bicarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, tartrate, sulfate, nitrate, thiosulfate, thio cyanate, formate, lactate, acetate, propionate, butyrate, pentanoate or oxalate,
- -
R30 is particularly preferably represented as lactate, sulfate, nitrate, thiosulfate, thiocyanate, oxalate or formate, R30 very particularly preferably represents sulphate. The combinations of active compound, salt and penetrant which are especially preferred according to the invention are listed in the table below. Here, "penetrating according to the test" means that each compound acting as a penetrant in the cuticle penetration test (Baur et al., 1997, Pesticide Science 51, 131-152) is adequate. The ammonium salts and the phosphonium salts of the formula (III ') can be used in a wide range of concentration to increase the activity of the compositions for the protection of cultures comprising ketoenols. In general, ammonium salts or phosphonium salts are used in a crop protection composition ready for use at a concentration of 0.5 to 80 mmol / 1, preferably 0.75 to 37.5 mmol / 1, particularly preferably from 1.5 to 25 mmol / 1. In the case of a formulated product, the concentration of the ammonium salt and / or phosphonium salt in the formulation is chosen to be within these general, preferred or highly preferred ranges outlined after the formulation has been diluted to the
- - concentration of active compound desired. The concentration of the salt in the formulation herein is usually 1-50% by weight. In a preferred embodiment of the invention, the activity is increased by adding to the crop protection compositions not only an ammonium salt and / or a phosphonium salt but also also a penetrant. It is considered totally surprising that even in these cases an even greater activity increase is observed. The present invention thus also provides the use of a combination of a penetrant and ammonium salts and / or phosphonium salts to increase the activity of crop protection compositions comprising cyclic ketoenols substituted with cycloalkylphenyls active as insecticides as a compound active. The invention likewise provides compositions comprising cyclic ketoenols substituted with cycloalkylphenyls active as insecticides, penetrants and ammonium salts and / or phosphonium salts, which specifically include not only the active compounds formulated but also ready-to-use compositions (liquids). in spray). The invention further provides, finally, the use of these compositions to control harmful insects. Suitable penetrants in the present context include all those substances which are commonly used to enhance the penetration of the active compounds as
phytosanitary in the plants. Penetrants are defined in this context by their ability to penetrate from the liquid in aqueous spray and / or from the spray coating to the cuticle of the plant and thus increase the motility of the active compounds in the cuticle. The procedure described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Suitable penetrants are, for example, alkanoyl alkoxylates. The penetrants according to the invention are the alkoxylates of alkanols of the formula (IV) RO- (-AO) V_R '(IV) in which R represents straight or branched chain alkyl having 4 to 20 carbon atoms, R 1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl or n-hexyl, AO represents an ethylene oxide radical, a propylene oxide radical, an oxide radical butylene or represents radical mixtures ethylene oxide and propylene oxide or butylene oxide radicals and v represents numbers from 2 to 30. A preferred group of penetrants are alkanoyl alkoxylates of the formula
R-O- (-EO-) n -R '(IV-a)
wherein R is as defined above, R 'is as defined above, EO represents -CH2-CH2-0- and n represents numbers from 2 to 20. A further preferred group of penetrants are alkanoyl alkoxylates of the formula RO- (-EO-) p- (-PO-) gR '(IV'-b)
wherein R is as defined above, R 'is as defined above, EO represents -CH2-CH2-0, PO represents CH-CH-0-CH3
p represents numbers from 1 to 10 and q represents numbers from 1 to 10. A further preferred group of penetrants are alkanoyl alkoxylates of the formula R-O- (-PO-) r- (EO-) S-R '(IV'-c)
wherein R is as defined above, R 'is as defined above, EO represents -CH2-CH2-0,
- - I
PC represents -CH ^ CH-O-CH3
r represents numbers from 1 to 10 and s represents numbers from 1 to 10. A further preferred group of penetrants are the alkoxylates of alkanols of the formula RO- (-EO-) p- (-BO-) qR '(IV -d) wherein R and R1 are as defined above, EO represents CH2-CH2-0, BO represents -CH-CH1-CH-0, CH3
p represents numbers from 1 to 10 and q represents numbers from 1 to 10. A further preferred group of penetrants are the alkoxylates of alkanols of the formula RO- (-BO-) r- (-EO-) SR '(IV -e) wherein R and R1 are as defined above, BO represents -CH¿-CH-CH-0, CH3
EO represents CH2-CH2-0, r represents numbers from 1 to 10 and s represents numbers from 1 to 10.
-
A further preferred group of penetrants are alkanoyl alkoxylates of the formula CH3- (CH2) t-CH2-0- (-CH2-CH2-0-) uR '(IV -f) wherein R' is as defined above, t represents numbers from 8 to 13 or represents numbers from 6 to 17. In the above formulas, Rpreferably represents butyl, isobutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, -ethylhexyl, nonyl, isononyl, decyl, n-dodecyl, isododecyl, lauryl, myristyl, isotridecyl, trimethylnonyl, palmityl, stearyl or eicosyl. An example that can be mentioned of an alkanol alkoxylate of the formula (III-c) is 2-ethylhexyl alkoxylate of the formula CH 5 CH 2 CH 2 CH 2 - CH 2 O (PO) - (EO) 6-H
(IV -c-1)
wherein EO represents -CH2-CH2-0 PO represents CH2, - CI H-O and
the numbers 8 and 6 are average values. An example that can be mentioned of an alkanoyl alkoxylate of the formula (IV-d) is the formula CH3- (CH2) io-0- (-E0-) 6- (-BO-) 2-CH3 (IV -d- 1) in which EO represents CH2-CH2-0, BO represents -CH1-CHj-CH-0 and CH3 the numbers 10, 6 and 2 are average values. The alkylene alkoxylates of the formula (IV -f) which are particularly preferred are the compounds of this formula in which t represents numbers from 9 to 12 and u represents numbers from 7 to 9. The alkanoylalkoxylate of the formula (IV - f-1) CH3- (CH2) t-CH2-0- (-CH2-CH2-0-) uH (IV -f-1) where t represents the mean value 10.5 yu represents the mean value 8, 4 can be mentioned as being preferred in a very particular way. The above formulas provide a general definition of alkanoyl alkoxylates. These substances are mixtures of substances of the type that are cited with different
chain lengths. The indexes therefore have average values that can also deviate from the integers. The alkanoyl alkoxylates of the recited formulas are known and in some cases commercially available or can be prepared by known processes (see WO 98/35 553, WO 00/35 278 and EP-A 0 681 865). Suitable penetrants also include, for example, substances that promote the availability of the compounds of formula (I) in a spray coating. These include, for example, mineral and vegetable oils. Suitable oils are all mineral or vegetable oils - modified or not - which can be used usually in phytosanitary compositions. Mention may be made, for example, of sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn oil, cottonseed oil and soybean oil, or the asters of said oils. Preference is given to rapeseed oil, sunflower oil or its methyl or ethyl esters. The concentration of penetrants in the compositions according to the invention can vary over a wide range. In the case of a composition formulated for crop protection, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, particularly preferably from 15 to 40% by weight. In ready-to-use compositions (liquids
spray), the concentration is generally between 0.1 and 10 g / 1, preferably between 0.5 and 5 g / 1. The compositions for crop protection according to the invention can also comprise other components, for example, surfactants and / or dispersion aids or emulsifiers. The nonionic surfactants and / or adjuvants of the dispersion include all substances of this type that can be customarily used in plant protection compositions. Preferred are the block copolymers of ethylene oxide / propylene oxide, the polyethylene glycol ethers of straight-chain alcohols, the reaction products of fatty acids with ethylene oxide and / or propylene oxide, as well as the alcohol of polyethylene glycol. polyvinyl, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic esters, and also alkyl ethoxylates and alkylaryl ethoxylates, which optionally can be phosphated and optionally neutralized with bases, examples of which which may be mentioned are sorbitol ethoxylates, and also polyoxyalkyleneamine derivatives. Anionic surfactants include all substances of this type that can be commonly used in plant protection compositions. Preference is given to alkali metal salts and alkaline earth metal salts
alkylsulfonic acids or alkylarylsulfonic acids. A preferred group of anionic surfactants and / or dispersion adjuvants are the following salts which are of low solubility in vegetable oils: salts of polystyrenesulfonic acids, salts of polyvinyl sulfonic acids, condensation products of naphthalenesulfonic acid / formaldehyde salts, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde, and salts of lignosulfonic acid. Suitable additives which can be included in the formulations according to the invention are emulsifiers, foam inhibitors, preservatives, antioxidants, dyes and inert fillers. Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethoxylated arylalkylphenols, and also ethoxylated and propoxylated arylalkyphenols, and also arylalkyl ethoxylates and / or sulphated or fofated arylalkyl ethoxyproxylates, mentioning for example of the sorbitan derivatives, such as esters of fatty acids of ethylenosorbitan polyoxide and esters of sorbitan fatty acids. Using, for example, according to the procedure (A) N- (2,6-dimethyl-4-cyclopropyl-phenylacetyl) -1-amino-cyclohexanecarboxylate ethyl as starting material, can
The development of the method according to the invention is represented by the following reaction scheme:
Using, for example, according to the process (B) O- (2,6-dimethyl-4-cyclopropylphenylacetyl) -2-hydroxyisobutyrate ethyl ester, the development of the process according to the invention can be represented by the following reaction scheme :
Using, for example, according to the procedure
Ethyl 2- (2,6-dimethyl-4-cyclopropyl-phenyl) -4- (4-methoxy) benzylmercapto-4-methyl-3-oxovalerate, the development of the process according to the invention can be represented by the following reaction scheme :
Using, for example, according to the procedure (D) 2- (2,6-dimethyl-4-cyclopropylphenyl) ketene of chlorocarbonyl and acetone as starting materials, the development of the process according to the invention can be represented by the scheme of next reaction:
Using, for example, according to the procedure (E) 2- (2,6-dimethyl-4-cyclopropylphenyl) ketene chlorocarbonyl and thiobenzamide as starting materials, the development of the process according to the invention can be represented by the scheme of next reaction:
- -
Using, for example, according to the procedure (F) ethyl 5- (2,6-dimethyl-4-cyclopropyl-phenyl) -2,3-trimethylene-4-oxovalerate, the development of the process according to the invention can be represented. using the following reaction scheme:
Using, for example, according to the procedure (G) ethyl 5- [(2,6-dimethyl-4-cyclopropyl) phenyl] -2-methyl-5-oxohexanoate, the development of the process according to invention by means of the following reaction scheme:
Using, for example, according to the procedure (Ha) hexahydropyridazine and chlorocarbonyl 2- (2,6-dimethyl-4-cyclopropyl) phenyl ketene as starting materials, the development of the reaction of the process according to the invention can be represented by The following reaction scheme:
Using, for example, according to the procedure (γ) hexahydropyridazine and dimethyl 2- (2,6-dimethyl-4-cyclopropyl) phenylmalonate as starting materials, the development of the process according to the invention can be represented by the scheme of reaction below:
Using, for example, according to the procedure (??) l-ethoxycarbonyl-2- [(2,6-dimethyl-4-cyclopropyl) -phenylacetyl] hexahydropyridazine as starting material, can
- - represent the development of the reaction by means of the following scheme:
Using, for example, according to the process (I) ethyl N- (2,6-dimethyl-4-cyclopropylphenylacetyl) -1-aminocyclohexanecarboxylate as starting material, the development of the process according to the invention can be represented by The following reaction scheme:
Using, for example, according to the process (J) O- (2,6-dimethyl-4-cyclopropylphenylacetyl) -3-hydroxy-2, 2-ethyl dimethylpropionate, the development of the process according to the invention can be represented. using the following reaction scheme:
- -
Using, for example, according to the procedure (Ka) 3- (2-methyl-4-cyclopropyl-6-ethylphenyl) -5,5-dimethylpyrrolidin-2,4-dione and pivaloyl chloride as starting materials, it can be represented the development of the process according to the invention by means of the following reaction scheme:
Using, for example, according to the procedure (? ß) 3- (2,6-dimethyl-4-cyclopropyl-phenyl) -5,5-dimethylpyrrolidin-2,4-dione and acetic anhydride as starting materials, the development can be represented of the process according to the invention by means of the following reaction scheme:
Using, for example, according to the procedure (J) 8- [(2,6-dimethyl-4-cyclopropyl) phenyl] -1-aza-bicyclo (4, 3, O '6) nonan- 7, 9- dione and ethyl chloroformate as starting materials, the development of the process according to the invention can be represented by the scheme
- - following reaction:
Using, for example, according to procedure (M), 3- (2,6-dimethyl-4-cyclopropyl-phenyl) -4-hydroxy-5-methyl-6- (3-pyridyl) -pyrone and methyl chloromonothioformate as initial materials, the development of the reaction can be represented as follows:
Using, for example, according to the procedure (N) 3- (2,6-dimethyl-4-cyclopropyl-phenyl) -5,5-pentamethylene-pyrrolidine-2,4-dione and methanesulfonyl chloride as starting materials, the development can be represented of the reaction by the following reaction scheme:
- -
Using, for example, according to the procedure (0)
3- (2,6-dimethyl-4-cyclopropylphenyl) -4-hydroxy-5,5-di-methylpyrrolidin-2,4-dione and 2,2,2-trifluoroethylmethanethiophosphonyl chloride as starting materials, the development of the reaction by the following reaction scheme:
Using, for example, according to the procedure (P) 3- (2-ethyl-4-cyclopropyl-6-methylphenyl) -5-cyclopropyl-5-methylpyrrolidin-2,4-dione and NaOH as components, the development of the process according to the invention by the following reaction scheme Na (+)
- -
Using, for example, according to process (Q) variant to 3- (2,6-dimethylcyclopropylphenyl) -4-hydroxy-5,5-tetramethylene-A3-dihydrofuran-2-one and ethyl isocyanate as starting materials, The development of the reaction can be represented by the following reaction scheme:
Using, for example, according to the process (Q) variant β 3- (2-methyl-4-cyclopropyl-6-ethylphenyl) -5-methylpyrrolidin-2,4-dione and dimethylcarbamoyl chloride as starting materials, can be represented the development of the reaction using the following scheme:
Using, for example, according to the procedure (R) 3- (4-bromo-2, 6-dimethylphenyl) -5,5-dimethylpyrrolidin-2,4-dione and cyclopropylboronic acid as starting materials,
- - represent the development of the reaction by means of the following scheme:
The compounds, necessary as starting materials in the process (a) according to the invention, of the formula (II)
wherein A, B, D, J, m, X, Y and R8 are as defined above, are novel. The asters of the acylamino acids of the formula (II) are obtained, for example, when amino acid derivatives of the formula (XXVI)
in which
A, B, R and D are as defined above are acylated with substituted phenylacetic acid derivatives of the formula (XXVII)
(XXVII)
wherein J, m, X and Y are as defined above and Z represents a leaving group introduced by carboxylic acid activating reagents such as carbonyldiimidazole, carbodiimides (such as, for example, dicyclohexylcarbodiimide), phosphorylating agents (such as , for example, POCI3, BOP-Cl), halogenation agents, for example, thionyl chloride, oxalyl chloride, phosgene or chloroform esters, (Chem. Reviews 5J2, 237-416 (1953); Bhattacharya, Indian J. Chem 6, 341-5, 1968) or when the acylamino acids of the formula (XXVIII)
(XXVIII)
wherein A, B, J, m, X and Y are as defined above
- - are esterified (Chem. Ind. (London) 1568 (1968)) The compounds of the formula (XXVIII)
(XXVIII)
wherein A, B, D, J, m, X and Y are as defined above are novel. The compounds of the formula (XXVIII) are obtained when amino acids of the formula (XXIX)
wherein A, B and D are as defined above are acylated with substituted phenylacetic acid derivatives of the formula (XXVII)
(XXVII)
wherein J, m, X and Y are as defined above and Z is as defined above, for example according to Schotten-Baumann (Organikum,
- -
VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page 505). The compounds of the formula (XXVII) are novel. They can be prepared by methods known in principle and as shown in the examples (see, for example, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 8, pages 467-469 (1952 )). The compounds of the formula (XXVII) are obtained, for example, when the substituted phenylacetic acids of the formula (XXX)
wherein J, m, X and Y are as defined above are reacted with halogenating agents (for example thionyl chloride, thionyl bromide, oxalyl chloride, phosphene, phosphorus trichloride, phosphorus tribromide or sodium pentachloride). phosphorus), phosphonylating agents (such as, for example, POCI3, BOP-Cl), carbonyldiimidazole, carbodiimides (for example dicyclohexylcarbodiimide), if appropriate in the presence of a diluent (for example optionally chlorinated aliphatic or aromatic hydrocarbons, such as toluene) or methylene chloride, or ethers, for
- - example tetrahydrofuran, dioxane, methyl tertiary butyl ether), at temperatures from -20 ° C to 150 ° C, preferably from -10 ° C to 100 ° C. Some of the compounds of the formulas (XXVI) and (XXIX) are known from the patent literature that is cited at the beginning, and / or can be prepared by known procedures (see, for example, Compagnon, Miocque Ann. Chim. (Paris) [14] 5, pages 11-22, 23-27 (1970)). The substituted cyclic aminocarboxylic acids of the formula (XXIX) in which A and B form a ring can generally be obtained by Bucherer-Bergs synthesis or by Strecker synthesis, where they are obtained in each case in different isomeric forms. Thus, the conditions of the synthesis of Bucherer-Bergs predominantly provide the isomers (hereinafter referred to more simply as ß) in which the radicals R and the carbonyl group are in equatorial positions, while the Strecker synthesis conditions predominantly provide the isomers (hereinafter for simplicity will be referred to a) in which the amino group and the radicals R are in equatorial positions.
H H
- -
Synthesis of Bucherer-Bergs Synthesis of cker (ß-isomer) (isomer a) (L. Munday, J. Chem. Soc. 4372 (1961); J.T. Eward, C.
Jitrangeri, Can. J. Chem. 5_3, 3339 (1975). The initial materials, which are used in the above procedure (A), of the formula (II)
wherein A, B, D, J, m, X, Y and R8 are as defined above can also be prepared by reacting the aminonitriles of the formula (XXXI)
D wherein A, B and D are as defined above with substituted phenylacetic acid derivatives of the formula (XXVII)
- -
(XXVII)
wherein J, m, X, Y and Z are as defined above providing compounds of the formula (XXXII)
(XXXII)
wherein A, B, D, J, m, X and Y are as defined above, and then subjecting them to an acid alcoholysis. The compounds of the formula (XXXII) are also novel. The compounds, necessary as starting materials in the process (B) rding to the invention, of the formula (III)
in which
- -
A, B, J, m, X, Y and R8 are as defined above are novel. They can be prepared by methods known in principle. Thus, the compounds of the formula (III) are obtained, for example, when the 2-hydroxycarboxylic esters of the formula (XXXIII-A)
A C02R8? ""! (XXXIII-A) OH in which A, B and R8 are as defined above are acylated with substituted phenylacetic acid derivatives of the formula (XXVII)
(xxvii)
wherein J, m, X, Y and Z are as defined above (Chem. Reviews 52, 237-416 (1953)). In addition, the compounds of the formula (III) are obtained when the substituted phenylacetic acids of the formula (XXX)
- -
wherein J, m, X and Y are as defined above
they are alkylated with a-halocarboxylic esters of the formula (XXXIII-B)
A C02R8 (XXXIII-B) B Hal wherein A, B and R8 are as defined above and Hal represents chlorine or bromine. Some of the compounds of the formula (XXXIII) are commercially available, some are known; however, some are also novel. The compounds of the formula (XXXIII-B) are commercially available. The compounds of the formula (XXX) are novel. The compounds of the formula (XXX),
wherein J, m, X and Y are as defined above
- - are obtained, for example, when phenylacetic esters formula (XXXIV)
(XXXIV)
wherein J, m, X, Y and R8 are as defined above are hydrolyzed in the presence of acids or bases, in the presence of a solvent under generally known standard conditions. The compounds of the formula (XXXIV) are novel. The compounds of the formula (XXXIV)
(XXXIV)
wherein J, m, X, Y and R8 are as defined above are obtained by the process described in the examples analogously to the process (R) when the phenylacetic esters of the formula (XXXIV-a)
(XXXIV-a)
wherein R8, m, X and Y are as defined above
- and J 'represents bromine or iodine are reacted in the presence of cycloalkylboronic acid derivatives which can be coupled, for example cyclopropane-acid boronic, in the presence of a base and, if appropriate, in the presence of a catalyst (preferably palladium salts and a complex former, such as, for example, palladium acetate / tricyclohexylphosphine). The phenylacetic esters of the formula (XXXIV-a) are known in principle, for example from the open patent applications for public inspection WO 96/35 664, WO 97/02243, WO 97/01535, WO 98/05638 and DE-A-10 301 804, and can be prepared by the procedures described in these publications. The compounds, necessary as starting materials for the process (C) above, of the formula (IV)
wherein A, B, J, m, V, X, Y and R8 are as defined above are novel.
- -
They can be prepared by methods known in principle. The compounds of the formula (IV) are obtained, for example, when the substituted phenylacetic esters of the formula (XXXIV)
(XXXIV)
wherein J, m, X, Y and R8 are as defined above acylated with 2-benzylthiocarbonyl halides of formula (XXXV)
wherein A, B and V are as defined above and Hal represents halogen (in particular chlorine or bromine) in the presence of strong bases (see, for example,
M.S. Chambers, E.J. Thomas, D.J. Williams, J. Chem. Soc. Chem.
Commun., (1987), 1228). Some of the benzylthiocarbonyl halides of the formula (XXXV) are known, and / or can be prepared by known methods (J. Antibiotics (1983), 26, 1589).
- -
The halocarbonylketenes of the formula (VI) required as starting materials for the above processes (D), (E) and (H-a) are novel. They can be prepared by methods known in principle (see, for example, Org. Prep. Int.Proc. 7, (4), 155-158, 1975 and DE 1 945 703). Thus, for example, the compounds of the formula (VI)
wherein J, m, X and Y are as defined above and Hal represents chlorine or bromine are obtained when substituted phenylmalonic acids of the formula (XXXVI)
(XXXVI)
wherein J, m, X and Y are as defined above are reacted with acid halides, such as, for example, thionyl chloride, phosphorus chloride (V), phosphorus chloride (III), oxalyl, phosphene or thionyl bromide, if appropriate in the presence of catalysts,
- - such as, for example, dimethylformamide, methylstearylformamide or triphenylphosphine, and, if appropriate, in the presence of bases, such as, for example, pyridine or triethylamine. The substituted phenylmalonic acids of the formula
(XXXVI) are novel. They can be prepared in a simple manner by known processes (see, for example, Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page 517 ff, and EP-A-528 156, WO 96/35 664, WO 97/02 243 , WO 97/01535, WO 97/36868 and WO 98/05638). Thus, the substituted phenylmalonic acids of the formula (XXXVI)
(XXXVI)
wherein J, m, X and Y are as defined above are obtained when the phenylmalonic esters of the formula (XI)
wherein J, m, X and Y are as defined above
and u represents ORa,
- - where R is as defined above, they are initially hydrolyzed in the presence of a base and a solvent and then carefully acidified (see, for example, EP-A-528 156, WO 96/35 664, WO 97/02 243). The malonic esters of the formula (XI)
J, m, X and Y are as defined above and U represents OR8, where R8 is as defined above, are novel. They can be prepared by generally known methods of organic chemistry (see, for example, Tetrahedron Lett 27_, 2763 (1986), Organikum VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page 587 ff.), And WO 96/35664, WO 97. / 02243, WO 97/01535, WO 97/36868, WO 98/05638 and WO 99/47525). The carbonyl compounds, necessary as starting materials for the process (D) according to the invention, of the formula (V)
- -
wherein A and D are as defined above or their silylene ethers of the formula (Va) CHA D-C-OS (R8) 3 (Va)
wherein A, D and R8 are as defined above are commercially available compounds, generally known compounds or compounds obtainable by known procedures. The preparation of the ketal acid chlorides of the formula (VI), necessary as starting materials for carrying out the process (E) according to the invention, have already been described above. The thioamides, necessary to carry out the process (E) according to the invention, of the formula (VII)
wherein A is as defined above are compounds that are generally known in organic chemistry.
- -
The compounds, necessary as starting materials in the above process (F), of the formula (VIII)
wherein A, B, J, m, Q1, Q2, X, Y and R8 are as defined above are novel. They can be prepared by methods known in principle. The 5-aryl-4-ketocarboxylic esters of the formula (VIII) are obtained, for example, when the 5-aryl-4-ketocarboxylic acids of the formula (XXXVII)
(XXXVII)
wherein J, m, X, Y, A, B, Q1 and Q2 are as defined above are esterified (see, for example, Organikum, 15th edition, Berlin, 1977, page 499) or rented (see
- -
Preparation Example) The 5-aryl-4-ketocarboxylic acids of the formula (XXXVII)
(XXXVII)
wherein A, B, J, m, Q1, Q2, X and Y are as defined above are novel; however, they can be prepared by methods known in principle (documents O 96/01 798, WO 97/14667, WO 98/39281). The 5-aryl-4-ketocarboxylic acids of the formula (XXXVII) are obtained, for example, when the 2-phenyl-3-oxoadipic esters of the formula (XXXVIII)
(XXXVIII)
wherein A, B, J, m, Q1, Q2, X and Y are as defined above and
R8 and R8 'represent n alkyl (in particular Ci-C8 alkyl) Y, when the compound of the formula (XL-a), R8 is used
- - represents hydrogen, is decarboxylated, if appropriate in the presence of a diluent and if appropriate in the presence of a base or an acid (see, for example, Organikum, 15th edition, Berlin, 1977, pages 519 to 521, and WO 96/01798, WO 97/14667, WO 98/39281). The compounds of the formula (XXXVIII)
(XXXVIII)
wherein A, B, J, m, Q1, Q2, X, Y, R8, R8 'are as defined above and, when the compound of the formula (XL-a) is used, R8 represents hydrogen, are new. The compounds of the formula (XXXVIII) are obtained, for example, when the chlorides of dicarboxylic monoesters of the formula (XXXIX),
C02R (XXXIX)
in which
- -
A, B, Q1, Q2 and R1 are as defined above and Hal represents chlorine or bromine or carboxylic anhydrides of the formula (XL-a)
wherein A, B, Q1 and Q2 are as defined above acylate with a phenylacetic ester of the formula (XXXIV)
(XXXIV)
wherein J, m, X, Y and R8 'are as defined above in the presence of a diluent and in the presence of a base
(see, for example, M.S. Chambers, E.J. Thomas, D.J.
Williams, J. Chem. Soc. Chem. Commun. , (1987), 1228, see also the Preparation Examples). Some of the compounds of formulas (XXXIX) and (XL-a) are known compounds of organic chemistry, and / or can be prepared in a simple manner by methods known in principle. The compounds, necessary as initial materials in
- - the above procedure (G), of the formula (IX)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X, Y and R8 are as defined above, are novel. They can be prepared by methods known in principle. The 6-aryl-5-ketocarboxylic esters of the formula (IX) are obtained, for example, when the 6-aryl-5-ketocarboxylic acids of the formula (XLI)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above are esterified (see, for example, Organikum, 15th edition, Berlin, 1977, page 499, and WO documents
- -
99/43649, WO 99/48869). The 6-aryl-5-ketocarboxylic acids of the formula (XLI)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above are novel. They can be prepared by methods known in principle (WO 99/43649, WO 99/48869), for example when substituted 2-phenyl-3-oxoheptanedioic esters of the formula (XLII)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above and R8 and R8 'represent n alkyl (preferably Ci-C6 alkyl) and, when the compound is used of the formula (XL-b), R8 represents hydrogen
they are hydrolyzed and decarboxylated, if appropriate in the presence of a diluent and if appropriate in the presence of a base or an acid (see, for example, Organikum, 15th edition, Berlin, 1977, pages 519 to 521, and WO 99 / 43649, WO 99/48869). The compounds of the formula (XLII)
wherein A, B, J, m, Q3, Q4, Q5, Q6, X, Y, R8 and R8 'are as defined above are novel and can be obtained when dicarboxylic esters of the formula (XLIII),
(XLIII)
wherein A, B, Q3, Q4, Q5, Q6 and R8 are as defined above or carboxylic anhydrides of the formula (XL-b)
- -
wherein A, B, Q3, Q4, Q5, Q6 are as defined above are condensed with a substituted phenylacetic ester of the formula (XXXIV)
(XXXIV)
wherein J, m, X, Y and R8 'are as defined above in the presence of a diluent and in the presence of a base.
Some of the compounds of the formula (XLIII) are known, and / or can be prepared by known methods.
Some of the hydrazines, necessary as starting materials for the processes (Ha) and (β-β) according to the invention, of the formula (X) A-NH-NH-D (X) in which A and D are as defined above are known, and / or can be prepared by methods known from the literature (see, for example,
- -
Liebigs Ann. Chem. 585, 6 (1954); Reaktionen der organischen Synthese [Reactions of organic synthesis], C. Ferri, pages 212, 513; Georg tieme Verlag Stuttgart, 1978; Liebigs Ann. Chem. 443, 242 (1925); Chem. Ber. 98, 2551 (1965), and EP-A-508 126, WO 92/16510, WO 99/47 525, WO 01/17 972). The compounds, necessary for the process (? -?) According to the invention, of the formula (XII)
wherein A, D, J, m, X, Y and R8 are as defined above are novel. The acylcarbazates of the formula (XII) are obtained, for example, when the carbazones of the formula (XLIV)
A. / C02R8 N 2 I (XLIV) .NH D
wherein A, R8 and D are as defined above are acylated with substituted phenylacetic acid derivatives of the formula (XXVII)
(XXVII)
wherein J, m, X, Y and Z are as defined above (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968). Some of the carbazatos of the formula (XLIV) are commercially available compounds and some are known compounds, or they can be prepared by organic chemistry methods known in principle. The compounds of the formula (XXVII) have already been described related to the precursors for the processes (A) and (B). The compounds, necessary as starting materials for the process (I) according to the invention, of the formula (XIII)
where A, B, D, J, m, Q1, Q2, X, Y and R8 are as defined
- - previously, they are novel. The esters of the acylamino acids of the formula (XIII) are obtained, for example, when amino acid derivatives of the formula (XLV)
wherein A, B, Q1, Q2, R8 and D are as defined above are acylated with substituted hetarylacetic acid derivatives of the formula (XXVII)
(XXVII)
wherein J, m, X, Y and Z are as defined above (Chem. Reviews 5_2, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968) or when the acylamino acids of the formula (LXVI)
-
wherein A, B, J, m, D, Q1, Q2, X and Y are as defined above are esterified (Chem. Ind. (London) 1568 (1968)). The compounds of the formula (LXVI)
wherein A, B, D, J, m, Q1, Q2, X and Y are as defined above are novel. The compounds of the formula (XLVI) are obtained when the β-amino acids of the formula (XLVII)
(XLVII)
wherein A, B, Q1, Q2 and D are as defined above are acylated with substituted phenylacetic acid derivatives of the formula (XXVII)
(XXVII) in which J, m, X, Y and Z are as defined above, for example according to Schotten-Baumann (Organikum,
VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page
505). The compounds of the formula (XXVII) are novel. They can be prepared by methods known in principle (see, for example, H. Henecka, Houben-Weyl, ethoden der Organischen Chemie, Vol. 8, pages 467-469 (1952), and WO 97/02243, WO 99/43699 ), or are generated in situ using the reagents listed above. Some of the compounds of the formulas (XLV) and (XLVII) are known from WO 01/79204, or can be prepared by the process, known in principle, which is provided in this publication. The compounds, necessary as starting materials for the process (J) according to the invention, of the
- - formula (XIV)
wherein A, B, J, m, Q1, Q2, X, Y and R8 are as defined above, are novel. The acylhydroxycarboxylic esters of the formula (XIV) are obtained, for example, when the hydroxycarboxylic esters of the formula (XLVIII)
(XLVIII)
wherein A, B, Q1, Q2 and R8 are as defined above are acylated with substituted phenylacetic acid derivatives to formula (XXVII)
(XXVII)
- - wherein J, m, X, Y and Z are as defined above (see Preparation examples of the formula (II)). Some of the compounds of the formula (XLVIII) are known from WO 01/98288, or can be prepared by processes known in principle, for example by the synthesis of Reformatskij (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1990, 18a ed., page 501 ff.) The compounds of the formula (XXVII) are novel.
They can be prepared by methods known in principle (see, for example, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie, Vol. 8, pages 467-469 (1952), and WO 97/02243, WO 99/43649) . The acid halides of the formula (XV), carboxylic anhydrides of the formula (XVI), chloroformic esters or chloroform thioesters of the formula (XVII), chloromonothioformic esters or chlorodithioformic esters of the formula (XVIII), sulfonyl chlorides of the formula (XIX), phosphorus compounds of the formula (XX) and metal hydroxides, metal alkoxides or amines of the formulas (XXI) and (XXII) and isocyanates of the formula (XXIII) and carbamoyl chlorides of the formula (XXIV) and also derivatives of cycloalkylboronic acids (XXV) also needed as starting materials to carry out the processes (K), (L), (M), (N),
-
(0), (?), (Q) and (R) according to the invention are generally known compounds of organic or inorganic chemistry. In addition, the compounds of formulas (V), (VII), (X), (XXVI), (XXIX), (XXXI), (XXXIII-A), (XXXIII-B), (XXXV), (XXXIX) , (XL-a), (XL-b), (XLIII), (XLIV), (XLV), (XLVII) and (XLVIII) are likewise known from the patent applications cited at the beginning, and / or they can be prepared by the procedures that are provided in these publications. Process (A) is characterized in that the compounds of the formula (II) in which A, B, D, J, m, X, Y and R8 are as defined above are subjected to an intramolecular condensation in the presence of a base. Suitable for use as diluents in process (A) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tere-butanol. Suitable bases (deprotonation agents) for carrying out process (A) according to the invention are all common proton acceptors. Is granted
- - preference for the use of alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C8-Cio) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When the process (A) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (A) according to the invention is generally carried out at atmospheric pressure. When the process (A) according to the invention is carried out, the components of the reaction of the formula (II) and the deprotonating bases are generally used in
amounts approximately double the equimolars. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. Process (B) is characterized in that the compounds of the formula (III) in which A, B, J, m, X, Y and R8 are as defined above are subjected to an intramolecular condensation in the presence of a diluent and in the presence of a base. Suitable for use as diluents in process (B) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol. Suitable bases (deprotonation agents) for carrying out process (B) according to the invention are all common proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and carbonate.
- - calcium, which can also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 -Cy) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When the process (B) according to the invention is carried out, the reaction temperatures can vary in a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (B) according to the invention is generally carried out at atmospheric pressure. When carrying out the process (B) according to the invention, the reaction components of the formula (II) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. Process (C) is characterized in that the compounds
- of the formula (IV) in which A, B, V, J, m, X, Y and R8 are as defined above are cycled intramolecularly in the presence of an acid and, if appropriate, in the presence of a diluent . Suitable diluents for process (C) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as halogenated hydrocarbons, such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N- methylpyrrolidone. It is also possible to use alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol. If appropriate, the acid used can also serve as a diluent. Suitable for use as the acid in process (C) according to the invention are all customary inorganic and organic acids, such as, for example, hydrohalic acids, sulfuric acid, alkylsulfonic, arylsulfonic and haloalkylsulfonic acids, in particular halogenated alkylcarboxylic acids, such as, for example, trifluoroacetic acid. When the process (C) according to the invention is carried out, the reaction temperatures may vary
- - in a relatively broad range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (C) according to the invention is generally carried out at atmospheric pressure. When the process (C) according to the invention is carried out, the reaction components of the formula
(IV) and the acid are used, for example, in equimolar amounts. However, it is also possible, if appropriate, to use the acid as a solvent or as a catalyst. The process (D) according to the invention is characterized in that the carbonyl compounds of the formula
(V) or its enol ethers of the formula (V-a) are reacted with halides of ketonic acids of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid acceptor. Suitable diluents for use in process (D) according to the invention are all inert organic solvents. Preference is given to the use of optionally halogenated hydrocarbons, such as toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, in addition to ethers, such as dibutyl ether, glycol dimethyl ether, diglycoldimethyl ether and diphenyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide or N-methylpyrrolidone.
The acid acceptors suitable for carrying out the process variant (D) according to the invention are all customary acid acceptors. Preference is given to the use of tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononane (DBN), Hünig's base and N, -dimethylaniline. When the process variant (D) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. Conveniently, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.
The process (D) according to the invention is conveniently carried out at atmospheric pressure. When carrying out the process (D) according to the invention, the reaction components of formulas (V) and (VI), wherein A, D, J, m, X and Y are as previously defined and Hal represents halogen, and, if appropriate, acid acceptors are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 5 moles) of one or other components. The process (E) according to the invention is characterized in that the thioamides of the formula (VII) are reacted with halides of ketonic acids of the formula (VI)
in the presence of a diluent and, if appropriate, in the presence of an acid acceptor. Suitable for use as diluents in the process variant (E) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone. Suitable for use as acid acceptors to carry out process (E) according to the invention are all customary acid acceptors. Preference is given to the use of tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononane (DBN), Hünig's base and N, N-dimethylaniline. When carrying out the process (E) according to the invention, the reaction temperatures can vary over a relatively wide range. Conveniently, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 20 ° C and 220 ° C. The process (E) according to the invention is conveniently carried out at atmospheric pressure. When the procedure (E) is carried out according to
- - with the invention, the reaction components of formulas (VII) and (VI), wherein A, J, m, X and Y are as defined above and Hal represents halogen, and, if appropriate Acid acceptors are generally used in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 5 moles) of one or other components. The process (F) is characterized in that the compounds of the formula (VIII) in which A, B, J, m, Q1, Q2, X, Y and R8 are as defined above are subjected to an intramolecular condensation in the presence of from a base. Suitable diluents for use in the process (F) according to the invention are all organic solvents which are inert towards the compounds participating in the reaction. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone. It is also possible to use alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol. Suitable bases (deprotonation agents) to carry out the process (F) according to the invention are all common proton acceptors. Is granted
Preference is given to using oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C8-Cio) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When the process (F) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at temperatures between -75 ° C and 250 ° C, preferably between -50 ° C and 150 ° C. The process (F) according to the invention is generally carried out at atmospheric pressure. When carrying out the process (F) according to the invention, the reaction components of the formula (VIII) and the deprotonating bases are generally used in
- - approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. The process (G) is characterized in that the compounds of the formula (IX) wherein A, B, Q3, Q4, Q5, Q6, J, m, X, Y and R8 are as defined above are subjected to a intramolecular condensation in the presence of bases. Suitable diluents for use in process (G) according to the invention are all organic solvents which are inert towards the compounds participating in the reaction. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone. It is also possible to use alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol. Suitable bases (deprotonation agents) for carrying out process (G) according to the invention are all common proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, carbonate
- - potassium and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (methyltrialkyl (C8_Q) ammonium chloride) or TDA 1 ( = tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When carrying out the process (G) according to the invention, the reaction temperatures can vary in a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (G) according to the invention is generally carried out at atmospheric pressure. When carrying out the process (G) according to the invention, the reaction components of the formula (IX) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component.
- -
The process (? -a) according to the invention is characterized in that hydrazines of the formula (X) or the salts of these compounds are reacted with halides of ketonic acids of the formula (VI) in the presence of a diluent and, if was appropriate, in the presence of an acid acceptor. Suitable diluents for use in process (H-a) according to the invention are all inert organic solvents. Preference is given to the use of optionally chlorinated hydrocarbons, such as, for example, mesitylene, chlorobenzene and dichlorobenzene, toluene, xylene, as well as ethers, such as dibutyl ether, glycol dimethyl ether, diglycoldimethyl ether and diphenylethane, in addition to polar solvents, such as dimethyl sulfoxide. , sulfolane, dimethylformamide or N-methylpyrrolidone. The acid acceptors suitable for carrying out the process variant (H-a) according to the invention are all customary acid acceptors. Preference is given to the use of tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononane (DBN), Hünig's base and N, -dimethylaniline. When the process variant (H-a) according to the invention is carried out, the reaction temperatures can vary in a relatively wide range. So
- - convenient, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.
The process (H-a) according to the invention is conveniently carried out at atmospheric pressure. When carrying out the process (Ha) according to the invention, the reaction components of the formulas (VI) and (X), wherein A, D, J, m, X and Y are as previously defined and Hal represents halogen, and, if appropriate, acid acceptors are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 5 moles) of one or other components. The process (? -β) is characterized in that the hydrazines of the formula (X) or the salts of this compound, wherein A and D are as defined above, are subjected to a condensation with malonic esters or malonamides of the formula (XI) in which U, J, m, X, Y and R8 are as defined above, in the presence of a base. Suitable diluents for use in the process (? -β) according to the invention are all inert organic solvents. Preference is given to the use of optionally halogenated hydrocarbons, such as toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane,
- - diphenyl ether, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide, dimethylacetamide and
N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol. Suitable bases (deprotonation agents) for carrying out the process (β-β) according to the invention are all customary proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C8-Cio) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. It is also possible to use tertiary amines, such as
- - triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononane (DBN), Hünig base and N, -dimethylaniline. When the process (β-β) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 280 ° C, preferably between 50 ° C and 180 ° C. The process (? -ß) according to the invention is generally carried out at atmospheric pressure. When the process (? -ß) according to the invention is carried out, the reaction components of the formulas (XI) and (X) are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or other components. The process (? -?) Is characterized in that the compounds of the formula (XII) in which A, D, J, m, X, Y and R8 are as defined above are subjected to an intramolecular condensation in the presence of a base. Suitable for use as diluents in the process (? -?) According to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers,
- - such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol. Suitable bases (deprotonation agents) for carrying out the process (? -?) According to the invention are all common proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C8-Cio) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.
- -
When the process (? -?) According to the invention is carried out, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (? -?) According to the invention is generally carried out at atmospheric pressure. When the process (? -?) According to the invention is carried out, the reaction components of the formula
(XII) and the deprotonating bases are generally used in approximately twice the equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. Process (I) is characterized in that the compounds of the formula (XIII) wherein A, B, D, J, m, Q1, Q2, X, Y and R8 are as defined above are subjected to an intramolecular condensation in the presence of a base. Suitable for use as diluents in process (I) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethyl sulfoxide,
- - formamide, dimethylacetamide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol. Suitable bases (deprotonation agents) for carrying out process (I) according to the invention are all common proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 -Cy) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When carrying out the process (I) according to the invention, the reaction temperatures can vary in a relatively wide range. In general, the procedure is carried out at temperatures between -80 ° C and 180 ° C.
- -
° C, preferably between -50 ° C and 120 ° C. The process (I) according to the invention is generally carried out at atmospheric pressure. When the process (I) according to the invention is carried out, the reaction components of the formula (XIII) and the deprotonating bases are generally used in approximately twice the equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. The process (J) is characterized in that the compounds of the formula (XIV) wherein A, B, Q1, Q2, J, m, X, Y and R8 are as defined above, are subjected to an intramolecular condensation in presence of a base. Suitable for use as diluents in process (j) according to the invention are all inert organic solvents. Preference is given to the use of hydrocarbons, such as toluene and xylene, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol. The suitable bases (deprotonation agents) for carrying out the process (J) according to the invention
they are all habitual proton acceptors. Preference is given to the use of oxides of alkali metals and alkaline earth metals, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which may also be used in the presence of phase transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl (C 8 -Cy) ammonium chloride) or TDA 1 (= tris (methoxyethoxyethyl) amine). It is also possible to use alkali metals, such as sodium or potassium. It is also possible to use amides and hydrides of alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. When the process (J) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C. The process (J) according to the invention is generally carried out at atmospheric pressure. When the process (J) according to the invention is carried out, the reaction components of the formula
- -
(XIV) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 moles) of one or the other component. The process (K-ct) is characterized in that the compounds of the formulas (Ila) to (? -10-a) are in each case reacted with carbonyl halides of the formula (XV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger. The diluents suitable for use in the process
(K-a) according to the invention are all solvents that are inert toward the acid halides. Preference is given to the use of hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, in addition to halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, as well as ketones, such as acetone and methyl isopropyl ketone, likewise to ethers, such as diethyl ether, tetrahydrofuran and dioxane, additionally to carboxylic esters, such as ethyl acetate, and also to very polar solvents, such as dimethyl sulfoxide and sulfolane. If the hydrolytic stability of the acid halide allows, the reaction can also be carried out in the presence of water. The acid binders suitable for the reaction of
according to the procedure (? -a) according to the invention are all customary acid acceptors. Preference is given to the use of tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononane (DBN), Hünig base and N, N-dimethylaniline, in addition to alkaline earth metal oxides, such as magnesium and calcium oxide, likewise alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide. The reaction temperatures in the process (K-a) according to the invention can vary over a relatively wide range. In general, the process is carried out at temperatures between -20 ° C and +150 ° C, preferably between 0 ° C and 100 ° C. When the process (Ka) according to the invention is carried out, the starting materials of the formulas (I-1-a) to (α-10-a) and the carbonyl halide of the formula (XV) are used each generally in approximately equivalent amounts. However, it is also possible to use a relatively large excess (up to 5 mol) of the carbonyl halide. The processing is done through the usual procedures.
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The process (? -ß) is characterized in that the compounds of the formulas (Ila) to (? -10-a) are reacted with carboxylic anhydrides of the formula (XVI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid trap. Suitable for use as diluents in the process (? -β) according to the invention are preferably diluents which are also preferred when acid halides are used. In addition, it is also possible during an excess of carboxylic anhydride to act simultaneously as a diluent. Acid scavengers suitable for the process (? -β), which are added, if appropriate, are preferably the acid scavengers which are also preferred when acid halides are used. The reaction temperatures in the process (β-β) according to the invention can vary over a relatively wide range. In general, the process is carried out at temperatures between -20 ° C and +150 ° C, preferably between 0 ° C and 100 ° C. When the process (β-β) according to the invention is carried out, the starting materials of the formulas (I-1-a) to (α-10-a) and the carboxylic anhydride of the formula (XVI) are they each use generally in approximately equivalent quantities. However, it is also possible to use a relatively large excess (up to 5 mol) of the carboxylic anhydride.
The processing is done through the usual procedures. In general, the diluent and the excess carboxylic anhydride and the carboxylic acid formed are removed by distillation or washing with an organic solvent or with water. The process (L) is characterized in that the compounds of the formulas (Ila) to (? -10-a) in each case are reacted with chloroformic esters or chloroform thioesters of the formula (XVII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger. The acid binders suitable for the reaction according to Process (L) according to the invention are all customary acid acceptors. Preference is given to the use of tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig base and N, N-dimethylaniline, in addition to alkaline earth metal oxides, such as magnesium oxide and calcium oxide, as well as carbonates of alkali metals and alkaline earth metals, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide. Suitable diluents for use in process (L) according to the invention are all solvents which
they are inert for chloroform esters or chloroform thioesters. Preference is given to the use of hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, in addition to halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and
0-dichlorobenzene, also to ketones, such as acetone and methyl isopropyl ketone, also to ethers, such as diethyl ether, tetrahydrofuran and dioxane, in addition to carboxylic esters, such as ethyl acetate, and also to very polar solvents, such as dimethyl sulfoxide and sulfolane. When the process (L) according to the invention is carried out, the reaction temperatures can vary over a relatively wide range. If the reaction is carried out in the presence of a diluent and an acid scavenger, the reaction temperatures are generally between -20 ° C and +100 ° C, preferably between 0 ° C and 50 ° C. The process (L) according to the invention is generally carried out at atmospheric pressure. When the process (L) according to the invention is carried out, the starting materials of the formulas (I-1-a) to (α-10-a) and the chloroformic ester or the appropriate chloroform thioester of the formula ( XVII) are generally used in approximately equivalent amounts. However, it is also possible to use a relatively excess
- - large (up to 2 mol) of one or the other components. The processing is done through the usual procedures. In general, the precipitated salts are removed and the remaining reaction mixture is concentrated by removing the diluent under reduced pressure. The process (M) according to the invention is characterized in that the compounds of the formulas (Ila) to (? -10-a) in each case are reacted with compounds of the formula (XVIII) in the presence of a diluent and, if appropriate, in the presence of an acid trap. In the preparation process (M), about 1 mole of chloromonothioformic ester or chlorodithioformic ester of the formula (XVIII) is reacted per mole of the initial material of the formulas (Ila) to (α-10-a) a from 0 to 120 ° C, preferably from 20 to 60 ° C. Suitable diluents, which are added, if appropriate, are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, and also halogenated alénes. Preference is given to the use of dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride. If, in a preferred embodiment, the enolate salt of the compounds (Ila) to (? -10-a) is prepared by the addition of potent deprotonation agents, such as, for example, sodium hydride or potassium tert-butoxide, can
- - avoid the subsequent addition of acid scavengers. If acid scavengers are used, customary inorganic or organic bases are usually suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine. The reaction can be carried out at atmospheric pressure or at elevated pressure and is preferably carried out at atmospheric pressure. The processing is done through the usual procedures. The process (N) according to the invention is characterized in that the compounds of the formulas (Ila) to (? -10-a) are in each case reacted with sulfonyl chlorides of the formula (XIX), if appropriate in presence of a diluent and if appropriate in the presence of an acid scavenger. In the preparation process (N), about 1 mole of sulfonyl chloride of the formula (XIX) is reacted per mole of starting material of the formula (Ila a? -10-a), at -20 to 150 ° C , preferably from 20 to 70 ° C. Suitable diluents, which are added, if appropriate, are all inert polar organic solvents, such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons, such as methylene chloride. Preference is given to the use of dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride.
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If, in a preferred embodiment, the enolate salt of the compounds (Ila) to (? -10-a) is prepared by the addition of potent deprotonation agents (such as, for example, sodium hydride or potassium tert-butoxide) the subsequent addition of acid scavengers can be avoided. If acid scavengers are used, customary inorganic or organic bases are usually suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine. The reaction can be carried out at atmospheric pressure or at elevated pressure and is preferably carried out at atmospheric pressure. The processing is done through the usual procedures. The process (O) according to the invention is characterized in that the compounds of the formulas (Ila) to (? -10-a) in each case are reacted with phosphorus compounds of the formula (XX), if appropriate in presence of a diluent and if appropriate in the presence of an acid scavenger. In the preparation process (O), to obtain compounds of the formulas (Ile) to (? -10-e) 1 to 2, preferably 1 to 1.3 moles of the phosphorus compound of the formula (XX) are used per mole of the compounds (Ila) to (? -10-a), at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C.
Suitable diluents, which are added, if appropriate, are all inert polar organic solvents, such as ethers, amides, nitriles, alcohols, sulfides, sulfones, sulfoxides, etc. Preference is given to the use of acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride. Suitable acid scavengers, which are added, if appropriate, are the customary inorganic or organic bases, such as hydroxides, carbonates or amines. Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine may be mentioned by way of example. The reaction can be carried out at atmospheric pressure or at elevated pressure and is preferably carried out at atmospheric pressure. The processing is done through the usual procedures of organic chemistry. The final products obtained are preferably purified by crystallization, chromatographic purification or by so-called "incipient distillation", ie removal of the volatile components under reduced pressure. The process (P) is characterized in that the compounds of the formulas (Ila) to (? -10-a) are reacted with metal hydroxides or metal alkoxides of the formula (XXI) or amines of the formula (XXII), if appropriate in the presence of a diluent.
- -
Suitable for use as diluents in the process (P) according to the invention are preferably ethers, such as tetrahydrofuran, dioxane, diethyl ether, or else alcohols, such as methanol, ethanol, isopropanol, but also water. The process (P) according to the invention is generally carried out at atmospheric pressure. The reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C. The process (Q) according to the invention is characterized in that the compounds of the formulas (Ila) to (? -10-a) are in each case reacted with (Qa) compounds of the formula (XXIII), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or (Q-ß) with compounds of the formula (XXIV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger. In the preparation process (Qa), about 1 mole of the isocyanate of the formula (XXIII) is used per mole of the initial material of the formulas (Ila) to (α-10-a), at 0 to 100 ° C, preferably from 20 to 50 ° C. Suitable diluents, which are added, if appropriate, are all inert organic solvents, such as ethers, amides, nitriles, sulfones, sulfoxides.
- -
If appropriate, catalysts can be added to accelerate the reaction. Suitable for use as catalysts are, very advantageously, organotin compounds, such as, for example, dibutyltin dilaurate. The reaction is preferably carried out at atmospheric pressure. In the preparation process (QS), about 1 mole of carbamoyl chloride of the formula (XXIV) is used per mole of the starting material of the formulas (Ila) to (α-10-a) at -20 to 150 ° C , preferably from 0 to 70 ° C. Suitable diluents, which are added, if appropriate, are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides or halogenated alkanes. Preference is given to the use of dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride. If, in a preferred embodiment, the enolate salt of the compounds (Ila) to (? -10-a) is prepared by the addition of potent deprotonation agents (such as, for example, sodium hydride or potassium tert-butoxide) the subsequent addition of acid scavengers can be avoided. If acid scavengers are used, customary inorganic or organic bases are usually suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine. The reaction can be carried out at atmospheric pressure or at
- - high pressure and preferably carried out at atmospheric pressure. The processing is done through the usual procedures. The catalysts suitable for carrying out the process (R) according to the invention are palladium (O) complexes. Preference is given, for example, to tetrakis (triphenylphosphine) palladium. If appropriate, it is also possible to use palladium (II) compounds, for example PdCl2,
Pd (0AC) 2- If palladium (II) compounds are used, phosphines, such as, for example, tricyclohexylphosphine, are generally used as complexing agents. The acid acceptors suitable for carrying out the process (R) according to the invention are inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate or ammonium acetate. , sodium carbonate, potassium carbonate, cesium carbonate or ammonium carbonate, sodium bicarbonate or potassium bicarbonate, alkali metal fluorides, such as, for example, cesium fluoride, alkali metal phosphates, such as, for example, potassium dihydrogen phosphate, and also tertiary amines, such as
- triraethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, -dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononane (DBN) or diazabicycloundecene (DBU). The diluents suitable for carrying out the process (R) according to the invention are water, organic solvents and any mixtures thereof. The following may be mentioned by way of example: aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, tethylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane or tetrachlorethylene; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl-t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole; alcohols, such as methanol, ethanol, n-isopropanol, n-iso, sec or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether; Water . When the process (R) according to the invention is carried out, the reaction temperature can vary over a relatively wide range. In general, the procedure
- - performs at temperatures between 0 ° C and +140 ° C, preferably between 50 ° C and +100 ° C. When the process (R) according to the invention is carried out, the boronic acids of the formula (XXV), wherein J is as defined above and the compounds of the formulas (? -1 ') a ( ? - ?? '), in which A, B, D, G, m, Q1, Q2, Q3, Q4, Q5 / Q6 X, Y, and J' are as defined above are used in a molar ratio from 1: 1 to 3: 1, preferably from 1: 1 to 2: 1. In general, from 0.005 to 0.5 mol, preferably from 0.01 mol to 0.1 mol, of catalyst are used per mol of the compounds of the formulas (? -α ') to (1-10'). The base is generally used in excess. The active compounds / combinations of active compounds of the invention, which combine good plant tolerance and favorable toxicity for warm-blooded animals and are well tolerated environmentally, are suitable for protecting plants and plant organs, to increase the yield of the crops, to improve the quality of the material collected and to control the pests of animals, in particular insects, arachnids, helminths, nematodes and molluscs, found in agriculture, in horticulture, in breeding of animals, in forests, gardens and recreational facilities, in the protection of stored products and materials, and in the hygiene sector. Preferably they can be used as
- - agents for the protection of crops. They are active against normally sensitive and resistant species and against all or some of the stages of development. The pests mentioned above include: From the order of the Anoplura (ftiraptera), for example,
Damalinia spp., Haematopinus spp. , Linognathus spp. , Pediculus spp., Trichodectes spp. From the Arachnida class, for example, Acarus served, Sheldoni mill, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae,
Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus. latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. From the Bivalve class, for example, Dreissena spp. From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp. From the order of the Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,
Anthonomus spp. , Anthrenus spp. , Apogonia spp. , Atomaria spp. , Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp. , Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzbphilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp. From the order of the Collembola, for example, Onychiurus armatus. From the order of the Dermaptera, for example, Forfícula auricularia. From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis , Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami , Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Typula paludosa, Wohlfahrtia spp. From the Gastropoda class, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp. From the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp. ., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Entero-bius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp. , Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides
stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella native, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti. It is also possible to control protozoa, such as Eimeria. From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livid, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp. , Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp. From the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycol spp., Brevicoryne brassicae,
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Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanígera, Cercopidae, Ceroplastes spp. , Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp. , Cryptorayzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp. , Diaspis spp., Doralis spp., Drosicha spp. , Dysaphis spp., Dysraicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp. , Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecaniura spp., Lepidosaphes spp., Lipaphis erysimi, acrosiphum spp. , Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp. , Nasonovia ribisnigri, Nephotettix spp. , Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp. , Pemphigus spp., Peregrinus maidis, Phenacoccus spp. , Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagon, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp. , Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera,
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Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Tri-aleurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. From the order of the Hyraenoptera, for example, Diprion spp. ,
Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber. From the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp. From the order of Lepidoptera, for example, Acronicta major, Aedy leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp. , Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanimous, Hyponomeuta padella, Laphygma spp. ., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Alacosoma neustria, Amestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp.,
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Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp. From the order of Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria. From the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of the Thysanura, for example, Lepisma saccharina. Phytoparasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema. spp. If appropriate, the compounds / combinations of active compounds according to the invention may,
- - certain concentrations or rates of application, also used as herbicides, protectants, growth regulators or agents to improve the properties of plants, or as microbicides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLO (organisms of the mycoplasma type) and RLO (organisms of the Rickettsia type). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds. All plants and all parts of plants can be treated according to the invention. In the present context it should be understood that plants refers to all plants and plant populations such as desired and unwanted wild plants or crop plants (including natural crop plants). The crop plants can be plants that can be obtained by conventional plant breeding and optimization procedures or by biotechnological and genetic engineering procedures or by combinations of these methods, which include the transgenic plants and which include the crop plant varieties that they may or may not be protected by the rights of the growers of the plants. The parts of the plants should be understood as meaning all the parts and organs of the plants above and below the ground, such as shoots, leaves, flowers and roots, may be mentioned as
- - examples the leaves, thorns, stems, trunks, flowers, fruit entities, fruits and seeds, roots, tubers and rhizomes. the parts of the plants also include the collected material and the material of vegetative propagation and by generation, for example cuttings, tubers, rhizomes, shoots and seeds. The treatment according to the invention of the plants and parts of the plant with the active compounds / combinations of active compounds is carried out directly or allowing the compounds to act in their surroundings, habitat or storage space by the usual treatment procedures, by example by immersion, spraying, evaporation, fogging, dispersion, painting or injection and, in the case of propagation material, in particular in the case of seeds, also by the application of one or more layers. The active compounds / combinations of active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions with water and oil base, powders, dusts, pastes, soluble powders, soluble granules, granules for emission, concentrates of suspension and emulsion, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and microencapsulations in polymeric substances.
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These formulations are produced in known manner, for example by mixing the active compounds / active compound combinations with fillers, i.e. liquid solvents and / or solid carriers, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam formers If the filler used is water, it is also possible to use, for example, organic solvents such as auxiliary solvents. Solvents suitable liquids are essentially aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic such as chlorobenzenes, chloroethylenes 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 also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, very polar solvents such as dimethyl sulfoxide, and also water. Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as high silica dispersion, alum and silicates; solid vehicles suitable for
- - granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, or if not synthetic granules of inorganic and organic powders, and granules of organic material such as sawdust, coconut shell, ears of corn and tobacco stalks; emulsifiers and / or forming suitable foam are nonionic and anionic example emulsifiers such as fatty acid esters, polyoxyethylene fatty alcohol ethers of polyoxyethylene, for example, ethers of alkylaryl sulfonates, alkyl sulfates, alkyl sulfonates, aryl , or if not protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose. In formulations can be used tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or polymer, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins dispersions, and synthetic phospholipids. Other additives can be mineral and vegetable oils. It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron,
manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
The active compound / combinations of active compounds according to the invention may be present in their commercially available formulations, as well as in the forms of use, prepared from these formulations, in the form of a mixture with other active compounds, such as insecticides , attractants, sterilizers, bactericides, acaricides, nematicides, fungicides, growth regulating substances, herbicides, protectants or fertilizers or semiochemical substances. Components particularly favorable mixing are for example the following compounds: Fungicides: Inhibitors of nucleic acid synthesis benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozilacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadioxilo, oxolinic acid inhibitors of mitosis and cell division benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide inhibitors of respiratory chain complex I diflumetorim the complex inhibitors of respiratory chain II
- - boscalid, carboxin, fenfuram, flutolanil, furametpir, mepronil, oxycarboxin, pentiopyrad, tifluzamide Inhibitors of the respiratory chain complex III azoxystrobin, cysoxamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin , picoxystrobin, trifloxystrobin Decouplers dinocap, fluazinam Inhibitors of ATP production fentin acetate, fentin chloride, fentin hydroxide, siltiofam Inhibitors of amino acid biosynthesis and protein biosynthesis andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipirim, pyrimethanil Inhibitors of signal transduction fenpiclonil, fludioxonil, quinoxifene Inhibitors of synthesis of lipids and membranes clozolinate, iprodione, procymidone, vinclozolin ampropilfos, potasium-ampropilfos, edifenfos, iprobenfos
(IBP), isoprothiolane, pyrazophos tolclofos-methyl, biphenyl iodocarb, propamocarb, propamocarb hydrochloride Inhibitors of ergosterol biosynthesis
fenhexamid, azaconazole, bitertanol, bromuconazole, ciproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, imazalil, imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pirifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorf, dodemorf , dodemorf acetate, fenpropimorf, tridemorph, fenpropidin, spiroxamine, naftifine, pyributicarb, terbinafine Inhibitors of cell wall synthesis bentiavalicarb, bialaphos, dimetomorf, flumorf, iprovalicarb, polyoxins, polioxorim, validamycin A Inhibitors of melanin biosynthesis capropamid, diclocimet , phenoxanyl, ftalid, pyroxy n, triciclazole Induction of acibenzolar-S-methyl, probenazole, tiadinyl resistance With several sites of captafol activity, captan, chlorothalonil, copper salts such
- - as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxina-copper and Bordeaux mixture, diclofluanide, dithianon, dodine, dodin free base, ferbam, folpet, fluorofolpet, guazatine , guazatine acetate, iminoctadine, iminoctadine albesilate ,. iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulfide, strip, tolilfluanid, zineb, ziram Unknown mechanism amibromdol, benthiazole, betoxazin, capsimycin, carvone, quinometionat, chloropicrin, cufraneb, ciflufenamide, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, dichlorophen, difenzoquat, diphenoquat methyl sulfate, diphenylamine, etaboxam, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, metasulfocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyl dithiocarbamate, nitrothal isopropyl, octhilinone, oxamocarb, oxyfentin, pentachlorophenol and salts, 2-phenylphenol and salts, piperalin, propanosine-sodium, proquinazid, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamid and 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1,3,3-trimethyl-1H-inden- 4-yl) -3-pyridinecarboxamide, 3- [5- (4-
- - chlorophenyl) -2, 3-dimethylisoxazolidin-3-yl] iridine, cis-1- (4-chlorophenyl) -2- (1H-1, 2, 4-triazol-1-yl) cycloheptanol, 2,4-dihydro- 5-methoxy-2-methyl-4- [[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1,2,3-triazol-3-one (185336) -79-2), methyl 1- (2,3-dihydro-2, 2-dimethyl-lH-inden-1-yl) -lH-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile , methyl 2 - [[[cyclopropyl [(4-methoxy phenyl) imino] methyl] thio] methyl] -alpha- (methoxymethylene) benzacetate,
4 - . 4-chloro-α-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] benzacetamide, (2S) -N- [2- [4- [[3- (4-chlorophenyl) ) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methylsulfonyl) amino] butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2, 4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine,
- . 5-chloro-6- (2,4,6-trifluorophenyl) -N- [(IR) -1,2,2-trimethylpropyl] - [1, 2, 4] triazolo [1, 5-a] pyrimidin-7 -amine, 5-chloro-N- [(IR) -1,2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7- amine, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] 2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl 2,4-dichloronicotinamide, 2-Butoxy-6-iodo-3-propylbenzopyranon 4-one, N-. { (Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy)
2,3-difluorophenyl] methyl} -2-benzacetamide, N- (3-ethyl-3,5,5 trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2- [[[[1 [3 (1-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha- (methoxyimino) -N-methyl-alphaE-benzacetamide, N-. { 2- [3-Chloro 5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoro-
- - methyl) benzamide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -l-methyl-lH-pyrazole-4-carboxamide, N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide, l - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-lH-imidazole-1-carboxylic acid, O- [1- [(4-methoxyphenoxy) methyl] -2 acid, 2-dimethylpropyl] -lH-imidazole-1-carbothioic acid, 2- (2 { [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2 - (methoxyimino) -N-methylacetamide Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. Insecticides / acaricides / nematicides: Acetylcholine esterase inhibitors (AChE) carbamates, for example alanicarb, aldicarb, aldoxicarb, aloxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxicarboxim, carbaryl, carbofuran, carbosulfan, cloetocarb, dimethylan, etiofencarb , fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate organophosphates,
- - for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlofenthion, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fention, flupirazophos, fonophos, formothion, fosmetilane, fosthilazate, heptenophos, iodophenes, iprobenfos, isazofos, isofenfos, isopropil O-salicylate, isoxation, malathion, mecarbam, methacryphs, methamidophos, metidation, mevinfos, monocrotophos, naled, ometoato , oxidometon-methyl, paration (-methyl / -ethyl), phenoate, phorate, phosalone, fosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propafos, propetamfos, protiofos, protoato, piraclofos, piridafention , pyridation, qu inalfos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion modulators / blockers of the sodium channel / channel blockers dependent sodium pyrethroids voltage, for example acrinathrin, allethrin (d-cis -trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, isomer bioalertin-s-cyclopentyl, bioetheromethrin, biopermethrin, bioresmethrin,
- - clovaportrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocitrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, teta-, zeta-), cyphenothrin, deltamethrin, empentrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpiritrine, fenvalerate, flubrocitrinate, flucitrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprotrin, kadetrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin ( lR-trans isomer), prallethrin, profluthrin, protrifenbuto, piresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, teralethrin, tetramethrin (IR isomer), tralometrine, transfluthrin, ZXI 8901, pyrethrins (pyrethrum) DDT oxadiazines, example indoxacarb semicarbazones, for example metaflumizone (BAS3201) Agonists / antagonists of acetylcholine receptors chloronicotinyl, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitiazine, thiacloprid, thiamethoxam nicotine, bensultap, cartap Modulators of acetylcholine receptors
- - spinosyns, for example spinosad Antagonists of the chloride channel controlled by organochlorinated GABA, for example camfeclor, clordane, endosulfan, gamma-HCH,
HCH, heptachlor, lindane, methoxychlor fiproles, for example acetoprol, ethiprole, fipronil, pyrafluprol, pyriprole, vaniliprole Mectin chloride channel activators, for example abamectin, emamectin, emamectin-benzoate, ivermectin, milbemycin Hormone mimetics of juveniles, or example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene agonists / disruptors diacylhydrazines ecdysone, for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide biosynthesis inhibitors of benzoylureas chitins, for example bistrifluron, clofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron,
- - triflumuron buprofezina ciromazina Inhibitors of oxidative phosphorylation, alterations of
ATP diafentiuron organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxide Decouplers of oxidative phosphorylation that act by interrupting the proton gradient H pyrrole, for example chlorfenapyr dinitrophenols, for example binapacirl, dinobuton, dinocap, DNOC Inhibitors of electron transport in the I METI site, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpirad hydramethylnon dicofol Inhibitors of electron transport in site II rotenone Inhibitors of electron transport in site III acequinocyl, fluacrypirim
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Microbial Alterators of the Intestinal Membrane of Insects Bacillus thuringiensis Strains Inhibitors of Lipid Synthesis Tetronic Acids, for example Spirodiclofen, Spiromesifen Tetramic Acids, for example Spirotetramat Carboxamides, for example Flonicamid Octopaminergic Agonists, for example Amitraz Magnesium-stimulated ATPase Inhibitors , propargite Effectors of ryanodine receptors, a) dicarboxamides of benzoic acid, for example flubendiamide b) anthranilamides, for example rinaxipir (3-bromo-N-. {4-chloro-2-methyl-6- [(methylamino)) carbonyl] phenyl.} -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide) Nereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultap-sodium Biological substances, hormones or pheromones azadirachtin, Bacillus spp . , Beauveria spp. , codlemone,
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Metarrhizium spp., Paecilomyces spp. , thuringiensine, Verticillium spp. Active compounds with unknown mechanisms of action or non-specific fumigants, for example aluminum phosphide, methyl bromide, sulfuryl fluoride, antifeedant substances, for example cryolite, flonicamide, pymetrozine, Acid growth inhibitors, for example clofentazine, etoxazole, hexythiazox amidoflumet, benclotiaz , benzoximate, bifenazato, bromopropilato, buprofezina, quinometionat, clordimeform, chlorobenzilate, chloropicrina, clotiazoben, ciclopreno, ciflumetofen, diciclanilo, fenoxacrim, fentrifañilo, flubencimina, flufenerim, flutenzina, gossyplure, hidrametilnona, japonilure, methoxadiazone, petroleum, piperonilo butoxide, oleato sodium, pyridalyl, sulfluramide, tetradifon, tetrasul, triaratene, verbutin. It is also possible to mix with other known active compounds, such as herbicides, fertilizers, growth regulators, protectants, semiochemicals or else with agents to improve the properties of the plants. When used as insecticides, the active compounds / combinations of active compounds according to the
The invention can also be present in its commercially available formulations and in the forms of use, prepared from these formulations, in the form of a mixture with synergistic agents. The synergists are compounds that increase the action of the active compounds, without the addition of the synergistic agent being necessary for it to be active.
When used as insecticides, the active compounds / combinations of active compounds according to the invention can also be present in their commercially available formulations and in the forms of use, prepared from these formulations, in the form of a mixture with inhibitors that they reduce the degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in the tissues of plants. The compound content of the use forms prepared from the commercially available formulations can vary within very wide ranges. The concentration of active compound of the forms of use can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight. The compounds are used in a customary manner suitable for the forms of use. As already mentioned above, it is possible to treat all the plants and their parts according to the invention. In a preferred embodiment, species of
- - wild plants and varieties of crop plants, or those obtained by conventional biological breeding procedures, such as cross-linking or fusion with protoplasts, and their parts. In a further preferred embodiment, transgenic plants and crop plant varieties obtained by genetic engineering methods are treated, if appropriate in combination with conventional procedures (Genetically Modified Organisms) and their parts. The terms "parts", "parts of plants" and "parts of the plant" have been explained above. Particularly preferably, the plants of the crop plant varieties that are in each case commercially available or in use are treated according to the invention. Varieties of crop plants should be understood as meaning plants that have novel properties ("characteristics") that have been obtained by conventional breeding, by mutagenesis or by genetic engineering techniques. These can be varieties of crop plants, biotypes or genotypes. Depending on the plant species or varieties of crop plants, their location and growth conditions (soil, climate, vegetation period, diet), the treatment according to the invention can also cause superadditive ("synergistic") effects. . So, for example, it is
- - possible a reduced application rate and / or an extension of the activity spectrum and / or an increase in the activity of the substances and compositions that can be used according to the invention, better growth of the plant, greater tolerance to high temperatures or low, greater tolerance to drought or to the salt content of water or soil, greater flowering, greater ease of harvesting, accelerated maturation, higher yields of the harvest, higher quality and / or a higher nutritional value of the products harvested, better stability and / or processing capacity of the products collected, which exceed the effects that really should have been expected. The transgenic plants or cultivation plant varieties (obtained by genetic engineering) that should preferably be treated according to the invention include all plants which, thanks to genetic modification, receive material that confers advantageous useful characteristics to these plants. Examples of these characteristics are better growth of the plant, greater tolerance to high or low temperatures, greater tolerance to drought or the salt content of water or soil, greater flowering, greater ease of harvesting, accelerated maturation, higher yields of the harvest, higher quality and / or greater nutritional value of the products harvested, better stability and / or processing capacity of the products harvested.
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Additional and particularly emphasized examples of these characteristics are a better defense of plants against animal and microbial pests, such as against insects, acarids, phytopathogenic fungi, bacteria and / or viruses, and also greater tolerance of plants to certain active compounds such as herbicides. Examples of transgenic plants that may be mentioned are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beet, tomatoes, peas and other plant varieties, cotton, tobacco, rapeseed and also fruit plants ( with fruits such as apples, pears, citrus fruits and grapes) and particularly corn, soy, potatoes, cotton, tobacco and rape are emphasized. The features that are emphasized are in particular greater defense of the plants against insects, arachnids, nematodes and slugs and snails thanks to the toxins formed in the plants, in particular those formed in the plants by the genetic material of Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also their combinations) (referred to as "Bt plants" below). The characteristics that are also emphasized in a particular way are the plants' greatest defense against fungi, bacteria and viruses through an acquired systemic resistance (SAR), systemin genes, phytoalexins, elicitors and resistance and the proteins and toxins that are expressed from
- - corresponding form. The features that are further emphasized in particular are the greater tolerance of the plants to certain active compounds such as herbicides, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes that confer the desired characteristics in question may also be present in combination with each other in the transgenic plants. Examples of "Bt plants" that may be mentioned are maize varieties, cotton varieties, soya varieties and potato varieties sold under the tradenames YIELD GARD® (eg corn, cotton, soybean), KnockOut® ( for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants that may be mentioned are maize varieties, cotton varieties and soybean varieties that are sold under the trade names Roundup Ready® (glyphosate tolerance, eg corn, cotton, soybean), Liberty Link® ( tolerance to phosphinothricin, for example rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example corn). Herbicide-resistant plants (plants conventionally reproduced for herbicide tolerance) that may be mentioned include varieties sold under the name Clearfield® (e.g. corn). Of course, these statements also apply to the
- - varieties of crop plants that have these genetic characteristics or genetic characteristics that still need to be developed, varieties of crop plants that will be developed and / or marketed in the future. The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I and / or the mixtures of active compounds according to the invention. The preferred ranges mentioned above for the active compounds or their mixtures are also applicable to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in this text. The active compounds / compositions of active compounds according to the invention act not only against plant pests, hygiene or stored products, but also in the field of veterinary medicine against animal parasites (ectoparasites and endoparasites), such as ticks. hard, soft ticks, scabies mites, leaf mites, flies (stinging and sucking), larvae of parasitic flies, lice, hair lice, lice from feathers and fleas. These parasites include: From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp. , Pediculus spp. , Phtirus spp. , Solenopotes spp.
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From the order of the allophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp. From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp. , Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp. From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp. From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. From the subclass of the Acari (Acariña) and the orders of the Meta- and Mesostigmata, for example, Argas spp.,
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Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. ., Varroa spp. Of the order of the Actinedida (Prostigmata) and Acaridida
(Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp. , Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. The active compounds / compositions of active compounds of the formula (I) according to the invention are also suitable for controlling arthropods that infest productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels , buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish and also the so-called laboratory animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, the cases of death and reduction of productivity (of meat, milk, wool, skins, eggs, honey, etc.) should be reduced so that the raising of animals is possible.
- - economical and easier by using the active compounds according to the invention. The active compounds / compositions of active compounds according to the invention are used in the veterinary field and in animal husbandry in a known manner by enteral administration in the form, for example, of tablets, capsules, potions, concoctions, granules, pastes , boluses, the delivery process with the food and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by parenteral administration, by dermal use in the form, by example, immersion or bathing, spraying, pouring and application in drops, washing and dusting, and also with the aid of molded articles containing the active compound, such as collars, lobular labels, labels for the tail, bands for the legs, purlins , marking devices and the like. When used for cattle, poultry, pet animals and the like, the active compounds of the formula (I) can be used as formulations (eg powders, emulsions, flowing compositions), which comprise the active compounds in an amount of 1. to 80% by weight, directly or after a dilution of 100 to 10,000 times, or can be used as a chemical bath.
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Furthermore, it has been found that the compounds / compositions of active compounds according to the invention also have a potent insecticidal action against insects that destroy industrial materials. The following insects may be mentioned as examples and as preferred, but without limitation: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spp. Tryptodendron spp. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spp. Dinoderus minutus; Hymenoptera, such as Sirex juvencus, Urocerus gigas,
Urocerus gigas taignus, Urocerus augur; Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heteroterm.es indicala, Reticulitermes flavipes, Reticuli termes santonensis, Reticulitermes lucifugus, Masto-termes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Silver minnows, such as Lepisma saccharina. Industrial materials in the present case should be understood as meaning non-living materials, such as, preferably, plastics, adhesives, glues, papers and
- - cartons, leather, wood and processed wood products and coating compositions. The materials to be protected in a very particularly preferable way against the attack of insects are wood and processed wood products. The wood and processed wood products that can be protected by the composition according to the invention or their mixtures comprising said composition should be understood to mean, for example: Wood products processed for construction, wooden beams, sleepers of the train tracks, bridge components, docks, wooden vehicles, boxes, pallets, containers, telephone poles, wood veneers, windows and doors made of wood, boards, DM, joinery, or wood products that, quite generally, they are used in the construction of houses or in cabinetmaking. The active compounds can be used as such, in the form of concentrates or generally in customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes. The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, if appropriate, dryers and stabilizers against the UV rays
- - and, if appropriate, dyes and pigments and other process adjuvants. The compositions or concentrates of insecticides which are used for the protection of wood and wood materials comprise the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular of 0.001 to 60% by weight. The amount of the compositions or concentrates that is used depends on the species and the presence of the insects and the environment. The optimum application rate can be determined in each case by a series of tests. However, in general, it is sufficient to employ from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, of the active compound, based on the material to be protected. The solvent and / or diluent used is a solvent or mixture of organochemical solvents and / or a solvent or mixture of oily or oily low volatility organochemical solvents and / or a solvent or mixture of polar organochemical solvents and / or water and, if appropriate, an emulsifier and / or wetting agent. The organochemical solvents that are preferably used with oily or oily type solvents having an evaporation number greater than 35 and a gas evolution temperature higher than 30 ° C, preferably higher than 45 ° C. The substances that are used as such
- oily or oily type solvents having a low volatility and suitable mineral oils or their aromatic fractions, or mixtures of solvents containing mineral oils, preferably turpentine, petroleum and / or alkylbenzene, are insoluble in water. The substances that are used advantageously are mineral oils with a boiling range of 170 to 220 ° C, turpentine with a boiling range of 170 to 220 ° C, extra-light oil with a boiling range of 250 to 350 ° C, petroleum or aromatics boiling range 160 to 280 ° C, turpentine and the like. In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or mixtures with high boiling points of aliphatic and aromatic hydrocarbons having a boiling range of 180 to 220 ° C and / or extra-light oil and / or monochloronaphthalene, preferably α-monochloronaphthalene. Oily or low-volatility oily organic solvents having an evaporation number greater than 35 and a gassing temperature of greater than 30 ° C, preferably higher than 45 ° C, can be partially replaced by high volatility organochemical solvents or medium, with the proviso that the solvent mixture also has an evaporation number greater than 35 and a gas evolution temperature higher than 30 ° C,
- - preferably higher than 45 ° C, and the insecticide / fungicide mixture is soluble or emulsifiable in this solvent mixture. In a preferred embodiment, part of the solvent or mixture of organochemical solvents or a solvent or mixture of aliphatic polar organochemical solvents is replaced. The substances which are preferably used are aliphatic organochemical solvents having hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters and the like. The organochemical binders that are used within the scope of the present invention are the synthetic resins and / or binder drying oils which are known per se and can be diluted with water and / or are soluble or dispersible or emulsifiable in the organochemical solvents that are used, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol, hydrocarbon resin, such as indene / coumaron resin, silicone resin, vegetable and / or drying oils and / or physically drying binders with a natural and / or synthetic resin base. The synthetic resin that is used as a binder can
- - used in the form of an emulsion, dispersion or solution. Up to 10% by weight of bitumen or bituminous substances can also be used as binders. In addition, colorants, pigments, water repellents, substances that mask the odor and inhibitors or anticorrosives known per se and the like may be employed. The composition or concentrate preferably comprises, according to the invention, at least one alkyd resin or a modified alkyd resin and / or a drying vegetable oil as an organochemical binder.
Preferably according to the invention, alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are used. All or some of the aforementioned binders can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to avoid volatilization of the active compounds and crystallization or precipitation. Preferably they replace 0.01 to 30% of the binder (based on the 100% binder used). Plasticizers are the chemical classes of phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, phosphoric esters, such as tributyl phosphate, adipic esters, such as di (2-ethylhexyl) adipate, stearates, such as stearate
butyl or amyl stearate, the oleates, such as butyl oleate, the glycerol ethers or the glycol ethers with relatively high molecular weights, glycerol esters and p-toluenesulfonic esters. Chemically-binding agents are based on polyvinylalkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethylenebenzophenone. Particularly suitable as a solvent or diluent is also water, if appropriate in the form of a mixture with one or more of the organochemical solvents or diluents, emulsifiers and dispersants mentioned above. In particular, effective protection of the wood is achieved by large-scale industrial impregnation processes, for example vacuum, double-vacuum or pressure processes. The ready-to-use compositions may, if appropriate, comprise other insecticides and, if appropriate, also one or more fungicides. Suitable additional components that can be mixed are preferably the insecticides and fungicides that are mentioned in WO 94/29 268. The compounds mentioned in that document are expressly part of the present patent application.
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The most preferred components that can be mixed are insecticides, such as chlorpyrifos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiaclopride, methoxyfenoxide, triflumuron, clothianidin, spinosad, tefluthrin, and fungicides, such as epoxiconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, ciproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, do-2-propyl butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one. The compounds according to the invention can be used at the same time to protect objects which are in contact with salty or brackish water from the scale, in particular helmets, meshes, nets, buildings, moorings and signaling systems. The inlays by sessile Oligochaeta, such as Serpulidae, and of shells and species of the Ledamorpha group (barnacles), such as various species of Lepas and Scalpellum, or by species of the Balanomorpha group (Balanus), such as Balanus species o Pollicipes, increases friction traction of ships and as a consequence, causes a significant increase in operating costs due to higher energy consumption and frequent access to the dry dock.
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Apart from the incrustations by algae, for example of Ectocarpus sp. and Ceramio sp. , the incrustations by sessile Entomostraka groups, which are known by the generic term of Cirripedia (cirriped crustaceans), is of particular importance. Surprisingly, it has now been found that the compounds according to the invention, alone or in combination with other active compounds, have an outstanding antifouling action. Using the compounds according to the invention, alone or in combination with other active compounds, makes it possible to avoid the use of heavy metals such as, for example, in the sulfides of bis (trialkyltin), tri-n-butyltin laurate, tri-chloride -n-butyltin, copper oxide (I), triethyltin chloride, tri-n-butyl- (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, ethylene ethylene carbothiocarbamate, zinc dimethyldithiocarbamate, zinc ethylembistiocarbamate, zinc salts and copper salts of 2-pyridinatiol-1-oxide, bis-dimethyldithiocarbamoyl-cyclopentylcarbamate, zinc, copper ethylenebisdithiocarbamate (I), copper thiocyanate, copper naphthenate and tributyltin halides, or reduce the concentration of these compounds in a
- - substantial. If appropriate, ready-to-use antifouling paints may also comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
Preferably the suitable components combined with the antifouling compositions according to the invention are: algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endotal, fentin acetate , isoproturon, metabenzthiazuron, oxyfluorfen, quinoclamine and terbutrin fungicides such as benzo [b] thiophenecarboxylic acid cyclohexylamide S, S-dichloride, diclofluanide, fluorfolpet, 3-iodo-2-propynyl butylcarbamate, tolylfluanide and azoles such as azaconazole, ciproconazole , epoxiconazole, hexaconazole, metconazole, propiconazole and tebuconazole; molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimetacarb, Fe chelates; or conventional antifouling active compounds such as
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4, 5-dichloro-2-octyl-4-isothiazolin-3-one, di-sodomethylparatrile sulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 1-oxide 2-pyridinethanol, pyridintriphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetra-tetraethyl thiuram disulfide and 2,4,6-trichlorophenylmaleimide. The antifouling compositions which are used comprise the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight. Also, the antifouling compositions according to the invention comprise customary components such as, for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge , 1973. In addition to the active compounds algicides, fungicides, molluscicides and insecticidal active compounds according to the invention, antifouling paints comprise, in particular, binders. Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system,
- - vinyl chloride / vinyl acetate copolymers in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins combined with tar or bitumen compounds, asphalt and epoxy, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins. If appropriate, the paints also comprise inorganic pigments, pigments or organic dyes that are preferably insoluble in salt water. The paints may further comprise materials such as rosin to allow controlled release of the active compounds. In addition, the paints may comprise plasticizers, modifiers that affect the rheological properties and other conventional constituents. The compounds according to the invention or the mixtures mentioned above can also be incorporated into self-polishing antifouling systems. The active compounds are also suitable for controlling animal pests, in particular insects, arachnids and acarids, which are found in closed spaces, such as, for example, houses, factories, offices, vehicle cabins and the like. They can be used in insecticide products for the home to control these pests alone or
- - combined with other active compounds and adjuvants. They are active against sensitive and resistant species and against all stages of development. These pests include: From the order of the Scorpionidea, for example, Buthus occitanus. From the order of the Acariña, for example, Argas persicus, Argas reflexus, Bryobia sspp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae. From the order of the Araneae, for example, Aviculariidae, Arañeidae. From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. From the order of the Isopoda, for example, Oniscus asellus,
Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp. From the order of the Chilopoda, for example, Geophilus spp. From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus. From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta
- - brunnea, Periplaneta fuliginosa, Supella longipalpa. From the order of the Saltatoria, for example, Acheta domesticus. From the order of the Dermaptera, for example, Forfícula auricularia. From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp. From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp. From the order of the Coleoptera, for example, Anthrenus spp.,
Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum. From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp. , Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Typula paludosa. From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans,
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Tunga penetrans, Xenopsylla cheopis. From the order of Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum. From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis. From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans. They are used in the field of domestic insecticides, they are used alone or in combination with other suitable active compounds, such as phosphoric esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds of other kinds of known insecticides.
They are used in aerosols, sprayed products without pressure, for example pump sprays and atomizers, automatic fogging systems, nebulizers, foams, gels, products for evaporators with tablets for cellulose or polymer evaporators, liquid evaporators, evaporators for gels and membranes , evaporators propelled by propellants, evaporation systems that do not use energy or passives, strips for moths, bags for moths and gels for moths, in the form of granules or powders, in baits to spread or in bait stations.
The active compounds / combinations of active compounds according to the invention can also be used as defoliants, drying agents, for removing stubbles and as herbicides. Weeds in its broadest sense is meant to mean all plants that grow in places where they do not want them to grow. Whether the substances according to the invention act as non-selective or selective herbicides depends essentially on the application rate. The active compounds / combinations of active compounds according to the invention can be used, for example, in the following plants: Dicotyledonous herbs of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium , Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Atricaria, 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. Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana,
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Phaseolus, Pisum, Solanum, Vicia. Monocotyledonous herbs of the genera: Aegilops, Agro-pyron, Agrostis, Alopecurus, Apera, Oats, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digi-taria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Erio-chloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Monocotyledonous crops of the genera: Allium, Ananas,
Asparagus, Oats, Hordeum, Oryza, Panicum, Saccharum, Sécale, Sorghum, Triticale, Triticum, Zea. However, the use of the active compounds / combinations of active compounds according to the invention is not restricted in any way to these genera, but extends in the same way to other plants. Depending on the concentration, the active compounds / combinations of active compounds according to the invention are suitable for the non-selective control of weeds, for example, in industrial lands and railways and in roads and locations with and without trees. In the same way, the active compounds according to the invention can be used to control weeds in perennial crops, for example forests, ornamental tree plantations, orchards, vineyards, citrus plantations,
nut plantations, banana plantations, coffee plantations, tea plantations, rubber plantations, palm oil plantations, coconut plantations, soft fruit plantations and hop fields, on turf, sod and pasture and for selective control of weeds in annual crops. The compounds of the formula (I) / combinations of active compounds according to the invention have a potent herbicidal activity and a broad spectrum of activity when used in the soil and in aerial parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence. At certain concentrations or application rates, the active compounds / combinations of active compounds according to the invention can also be used to control animal pests and fungal or bacterial diseases in plants. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds. The active compounds / combinations of active compounds can be converted into customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders,
- - granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very thin capsules in polymeric substances. These formulations are produced in a known manner, for example by mixing the active compounds with fillers, ie the liquid solvents and / or solid carriers, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foamers. If the filler used is water, it is also possible to use, for example, organic solvents such as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic chlorinated hydrocarbons and chlorinated aliphatics such as chlorobenzenes, chloroethylenes 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 also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, very polar solvents such as dimethyl sulfoxide, and also water. Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as
- - high dispersion silica, alum and silicates; suitable solid vehicles for the granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic powders, and granules of organic material such as sawdust, peel coconut, corn cobs and tobacco stems; suitable emulsifiers and / or foam formers are, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates , or if not protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose. In the formulations, adhesion agents such as carboxymethylcellulose and natural and synthetic polymers can be used in the form of polymeric powders, granules or dispersions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other possible additives are mineral and vegetable oils. It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and phthalocyanine dyes
- - metallic, and trace nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. The formulations generally comprise between 0.1 and 95 weight percent active compound, preferably between 0.5 and 90%. The active compounds / combinations of active compounds according to the invention, as such or in their formulations, can also be used for weed control purposes as a mixture with known herbicides and / or with substances that improve the tolerance of crop plants. ("safeners"), which can be in ready-to-use mixtures or in tank mixes. Therefore, mixtures with herbicidal products containing one or more known herbicides and a safener are also possible. The herbicides which are suitable for the mixtures are known herbicides, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryn, amicarbazone, amidochlor, amidosulfuron, aminopyralid, anilofos, asulam, atrazine, azaphenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, bencarbazone, benzofendizone, benzobicyclone, benzophenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromophenoxy, bromoxynil, butachlor, butafenacilo (-alil), butroxidim, butylate, cafenstrol, caloxydim, carbetamide,
- - carfentrazone (-ethyl), clometoxifen, chloramben, chloridazon, chlorimuron (-ethyl), clornitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl), cinmethilin, cinosulfuron, clefoxidim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clo-pyralid, clopirasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutrin, cycloate, cyclo-sulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, diclorprop (-P), diclofop (-methyl), diclosulam, dietltil (-ethyl), difenzoquat, diflufenican, diflufenzopir, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, etalfluralina, etametsulfuron (-methyl), etofumesato, ethoxifen, ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flur acyclorac (-pentyl), flumioxazin, flumipropin, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpirsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -methyl) ), flurprimidol, flurtamone, flutiacet (-methyl), flutiamide, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxifop (-ethoxyethyl, -P-methyl), hexazinone, HOK-201, imazametabenz (-metil), imaza-
- - metapyr, imazamox, imazapic, imazapir, imazaquin, imazetapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxinil, isopropalin, isoproturon, isouron, isoxaben, isoxaclortole, isoxaflutole, isoxapirifop, lactofen, lenacil, linuron, MCPA, mecoprop , mefenacet, mesosulfuron, mesotrione, metamifop, metamitron, metazachlor, metabenzthiazuron, methobenzuron, methobromuron, (alpha-) metolachlor, metosulam, methoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon , orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxsulam, pentoxazone, fenmedifam, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron (-methyl), profluazol, prometryn, propane, propanil, propaquizafop, propisoclor, propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrosulfotol, pyrazoglyl, pyrazole ato, pirazosulfuron (-ethyl), pirazoxifen, piribenzoxim, piributicarb, pyridate, pyridatol, piriftalide, piriminobac (-methyl), pyrimisulfan, piritiobac (-sodium), piroxsulam, piroxasulfone, quinclorac, quinmerac, quinoclamine, quizalofop (-P-ethyl) , -P-tefuril), rimsulfuron, sethoxydim, simazine, symmetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tembotrione, tepraloxidim, terbutilazine, terbutryn, tenilchlor,
- - thiafluamide, thiazopyr, thidiazimine, thiencarbazonemethyl, thifensulfuron (-methyl), thiobencarb, thiocarbazyl, topramezone, tralcoxydim, trialate, triasulfuron, tribenuron (-methyl), triclopyr, tridifone, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron and
It is also possible to mix with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners. The active compounds / combinations of active compounds can be applied as such, in the form of their
- - formulations or forms of use prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are applied in the usual way, for example pouring, spraying, atomising, spreading. The active compounds / combinations of active compounds according to the invention can be applied both before and after the emergence of the plants. They can also be incorporated into the soil before planting. The application rate of the active compound can vary within a substantial range. Essentially, it depends on the nature of the desired effect. In general, the application rates are between 1 g and 10 kg of active compound per hectare of land area, preferably between 5 g and 5 kg per ha. The advantageous effect of the compatibility with the crop plants of the combinations of active compounds according to the invention is particularly pronounced at certain concentration ratios. However, the proportions by weight of the active compounds in the combinations of active compounds can vary in relatively wide ranges. In general, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100 parts by weight, particularly preferably from 0.05 to 20 parts by weight, of one of the compounds that improves the
- - compatibility of the crop plants (antidotes / safeners) mentioned above in (b1) per part by weight of active compound of the formula (I). The combinations of active compounds according to the invention are generally applied in the form of finished formulations. However, the active compounds contained in the combinations of active compounds can also be mixed during use, in the form of individual formulations, ie applied in the form of cistern mixtures. For certain applications, in particular by the post-emergence process, it may further be advantageous to include, as additional additives to the formulations, mineral or vegetable oils which are compatible with the plants (for example the commercial preparation "Rako Binol"), or ammonium salts, such as, for example, ammonium sulfate or ammonium thiocyanate. The combinations of novel active compounds can be used as such, in the form of their formulations or the forms of use prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is in the usual way, for example by watering, spraying, atomizing, dusting or spreading. The application rates of the combinations of
- active compounds according to the invention can be varied within a certain range; they depend, among others, on factors of time and the earth. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha, particularly preferably between 0.01 and 0.5 kg per ha. The combinations of active compounds according to the invention can be applied before and after the emergence of the plants, ie by the pre-emergence and post-emergence procedure. Depending on their properties, the safeners to be used according to the invention can be used to pre-treat the seed of the crop plant (seed coating) or can be introduced into the seed furrows before planting or can be used separately before the herbicide or together with the herbicide, before or after the emergence of the plants. Examples of plants that can be mentioned are important crop plants, such as cereals (wheat, barley, rice), corn, soybeans, potatoes, cotton, rapeseed, beet, sugar cane and also fruit plants (with fruits apples, pears, citrus and grape vines), placing great emphasis on cereals, corn, soy, potatoes, cotton and rapeseed. The term "active compounds" also always includes
- - the combinations of active compounds mentioned here. Preparation examples Example I-1-a-1
Initially, 0.88 g of potassium tert-butoxide are charged in 10 ml of N, N-dimethylformamide at 60 ° C, 1 g of the compound of Example II-1 are added, dissolved in 5 ml of N, N-dimethylformamide. , drop by drop during a period of 30 minutes and the mixture is stirred at 60 ° C for 4 h. The mixture is taken up in 100 ml of water, adjusted to pH 1 using 1 N HCl, concentrated, again taken up in water and concentrated. The residue is taken up in 10 ml of water and extracted with dichloromethane, and the extract is dried with sodium sulfate and concentrated. The residue is then stirred in 4 ml of ethyl acetate and filtered off with suction. This gives 0.3 g of a colorless solid (yield 36% of theory) of mp: 218 ° C.
Analogously to Example (I-1-a-1) and in accordance with the general guidelines on preparation, the following compounds of the formula (I-1-a) are obtained
A B pf ° C Isomer
2 - . 2 -C2H5 6- CH3 (CH2) 2-CHOCH3 222 ß
(CH2) 2- l-a-3 1 2 -C2H5 6- CH3 H -CH2-CHOC4H9- 203 ß
(CH2) 3- l-a-4 1 - (CH2) 2-CHOCH3 264 ß
(CH2) 2-
-C2H5 4- CH3 CH CH 262
n. ° of m X Y pf ° C Isomer Ex I-l-a-6 C2H5 4- CH3 (CH2) 2-CHOCH3- 245 ß
(CH2) 2- I-l-a-7 1 -CH3 6- CH3 (CH2) 2-CHOCH3- 113 ß
(CH2) 2-
I-l-a-8 1 -CH3 6- CH3 CH3 CH3 100
I-l-a-9 1 CH3 6- CH3 (CH2) 2-CHOC2H5 109 ß
(CH2) 3-
I-1-a-1-Cl-CH 3 CH 3 CH 3 * 1.33 ppm (s, 6 ?, 10 C (CH 3) 2), 0.75
(m, 2H, CH2
(cyclopropyl)), 0.60 and 0.51 ppm (in each case m, 1H,
n. ° of m A B pf ° C Isomer
Ex
CH2 (cyclopropyl)
) 6-C1 4- CH3 (CH2) 2-CHOCH3- * 3.26 ppm (s, 3H,
11 (CH2) 2- 0-CH3), 0.75 (m,
2H, CH2
(cyclopropyl)), 0.59 and 0.51 ppm 10 (in each case m, 1H, CH2 (cyclopropyl)
) -Cl 4- CH 3 -CH 2 -CHOC 4 H 9 - * 3.58 ppm (m, 2H,
12 (CH2) 3- OCH2), 0.80 (m,
2H, CH2
No. of m J X Y D A B pf ° C Isomer
Ex
(cyclopropyl)), 0.67 and 0.53 ppm (in each case ra, 1H, CH2 (cyclopropyl))
fifteen
n ° of Ej m J X Y D A B pf ° C Isomer
I-l-a-14 6-C1 4-CH3 H -CH2-CHOC2H5- * 3.45 ppra (m, 2H, ß
(CH2) 3- 0 ^ 2) / 0 ^ 75 (m, 2H, CH2
(cyclopropyl)), 0.59 and 0.51 ppm (in each case m, 1H, CH2 (cyclopropyl))
2.6_ < ] 4- CH3 - (CH2) 2-HOCH3- 258-260 ß
(CH2) 2- H2) 2- 283 ß
I-l-a-17 1 4- CH3 6-CH3 H -CH2-CHOC4H9- * 3.55 ppm (m, 2H, ß
(CH2) 3- OCH2), 0.75 (m, 2H,
CH2
° of Ej m JXY pf ° C Isctane (cyclopropyl)), 0.64 and 0.49 ppm (in each case m, 1H, CH2 (cyclopropyl)) la-18 1 6-C2H5 4-CH3) 3- 224- 226
0 of Ej m J X Y A B pf ° C Isomer l-a-20 1 6-CH3 4-C1 - (CH2) 2-CHOCH3- * 3.41 ppm (s, 3H, ß
(CH2) 2- O-CH3), 0.88 (m,
2H, CH2
(cyclopropyl)), 0.72 and 0.51 ppm (in each case m, 1H,
n. ° ds Ex m J A B pf ° C Isomer CH2 (cyclopropyl))
I-l-a-21 2 6-C2H5 H H CH3 CH3 216-219
I-l-a-22 2 6-C2H5 H H - (CH2) 2-CHOCH3- 245-248 ß
(CH2) 2-
I-l-a-23 2 4- CH3 H H CH3 222-225
I-l-a-24 1 2-a½ 6-CH3 H -CH2-CHOCH3- 202-205 cis
(CH2) 2- 10
-25 1 4 2-CH3 6-CH3 H -CH2-CHOCH3- 80-90 trans
(CH2) 2-
-26 2-CH3 6-CH - (CH2) 2-CH- (CH2) 2- 251 ß I
CH2OCH3
Initially 0.14 g of the compound of Example Ila-5 are charged to 8 ml of ethyl acetate, 0.05 g of triethylamine and 1.5 mg of 4-N, N '-dimethylaminopyridine are added and the mixture is heated to a 60 ° C. A solution of 0.05 g of isobutyl chloride in 2 ml of ethyl acetate is added in 7 portions over a period of 60 minutes, and the mixture is stirred at 60 ° C for 6 h. The mixture is allowed to stand overnight, then semiconcentrated sodium chloride solution is added and the organic phase is removed by separation and purified by column chromatography on silica gel (gradient of EtOAc / n-heptane 1: 9 to ethyl acetate). ethyl / n-heptane 100: 0). This gives 90 mg of a colorless solid (yield 60% of theory), mp: 151 ° C.
Analogously to Example (I-1-b-1) and according to the general guidelines on the preparation, the following compounds of the formula (I-1-b) are obtained
n. ° m J A B R1 pf ° C Isomer of Ej i-i- i * - < ] 2-C2H5 6- CH3 H -CH2-CHOC4H9- (CH2) 3- I-C3H7 173 b-2 I-l- 1 4_ | 2-C2H5 6- CH3 H - (CH2) 2-CHOCH3- i-C3H7 * 0.99 (dd, β-3 (CH2) 2-6H, CH (CH3) ^) 2.18 (s, 3H, Ar- C¾) 3.21 (m, lH,
n. ° m J X Y D A B r1 Pf ° C Isomer of Ex
? ¾ ?? 3) 1-1- 1 2-CH-3 6- CH3 H - (CH2) 2-HOCH3- i-C3H7 194-196 ß b-4 (CH2) 2- 1-1- 4_ ^ j 2-CH3 6"CH3 H-CH2-CHOC2H5-" ¾) 3- i-C3H7 199-202 ß b-5 1-1-] 6-C2H5 H - (CH2) 2-CHOCH3- i-C3H7 190 ß b -6 (CH2) 2-10 1-1- 2.6 4-CH3 HH? ™ 3 i-C3H7 162-163 b-7
1-1- 2 2.6- < ] 4-CH3 CH3 CH3 i-C3H7 171 b-9 1-1- 1 4-CH3 6-CH3 H -CH2-CHOC4H9- (CH2) 3- H3 * 3.47 ppm (m, ß
pf ° C Isomer n ° ° JXYD of Ej 2H, OCH2), b-io 2.04 ppm (s, 3H, COCH3), 5 0.85 - 0.50 ppm (broad multiplet, 4H, CH2 (cyclopropyl) 10) - (CH2) 2-CHOCH3 '-C3H7 220-222 ß 1-1- 2 2.6 4-CH3 HH b-11 (CH2) 2- -CHOCH3 -C3H7 186-187 ß
-CH3 H H 3 CH3 -C3H7 176-177 1-1- 2 CH 2, 6
n. ° m J X Y D A B R1 pf QC Ex isomer b-13 1-1- 2 6"C2Hs H H - (aí2) 2-CHOCH3- Í-C3H7 190-192 ß
b-14 (CH2) 2-
n. ° m J X Y D A B 1 pf ° C Isomer of Ej 1-1- 1 2 - < 6 ~ C2ÍÍ5 4_CH3 - (CH2) 3- H i-C3H7 * 4.75 ppm (m, 1H, CH-N-b-15 (bridgehead)), 1.10 ppm (m, 9H, Ar- CH2) -CH3 and CH (CH3)), 0.95 - 0.54 ppm (broad signal accumulation, 4H, C¾ (cyclopropyl)) * 1 H NMR (400 MHz, CDCl 3): displacements d in ppm
Example I-1-c-1
Initially 0.15 g of the compound of Example Ila-2 and 0.05 g of triethylamine in 8 ml of dichloromethane are charged, the mixture is stirred at room temperature for 5 minutes, 0.05 g of ethyl chloroformate are added and the The mixture is stirred at room temperature overnight. 5 ml of Na2CC solution > 3 to 10%, the mixture is stirred at room temperature for 10 minutes, separated using extraction cartridges and concentrated using a rotovap, and the residue is purified by column chromatography on silica gel using ethyl acetate / n-heptane 1/1 This provides 68 g of an oil (yield 38% of theory). 1 H NMR (400 MHz, CDCl 3): d = 2.18 (s, 3 H; Ar-CH 3), 3.23 (m, 1 H, CHOCH 3), 4.01 (q, 2 H, OCH 2 CH 3) PPm-
Analogously to Example (I-1-c-1) and in accordance with the general guidelines on preparation, the following compounds of the formula (I-1-c) are obtained
n ° of m J X Y D A B M R pf ° C Isomer Ex OO
I-l-c-2 1 ~ 2_C2H5 6 ~ ^ 3 H -CH2-CHOC4H9- * 2.46 (m, 2H, Ar-OI2)
(CH2) 2- 3.38 (m, lH, OIO-CH2)
4.01 (q, 2H, O-CH2-CH3)
- < -CH3 6- CH3 H - (CH2) 2-CHOCH3- OR C2H5 200-202
(CH2) 2-
2-CH3 6- CH3 H -CH2-CHOC2H5 O C2H5 190-192 ß
(CH2) 3-
B M R2 pf ° C Iscinero
I-l-c-5 1 4 2-CH 3 6- CH 3 H -CH 2 -CHOCH 3 O C 2 H 5 114-116 cis
(CH2) 2-5 I-l-c-6 1 4 2-CH3 6- CH3 H -? ^ - ???? ^ - O C2H5 177 trans
(CH2) 2-
I-l-c-7 1 2 ^ J 4 -CH3 6- CH3 H - (CH2) 2-CHOCH3 O C2H5 * 4.01 ppm (q, 2H, O- ß
(CH2) 2- CH2),
3.38 ppm (s, 3H, ¾
OCH3), 0.83 0.75,
0.66, 0.56 ppm (in each case m, 1H, CH2
(cyclopropyl))
4-CH3 6- CH3 H -CH2-CHOC2H5- O C2H5 * 4.01 ppm (q, 2H, O- ß
(CH2) 3- CH2), 3.53 ppm (s,
n ° of m J X Y D A B M R2 pf ° C Isomer Ex 2H, OCH2), 0.86 -
0.5 ppm (accumulation of signals, joints 5 4H, CH2
(cyclopropyl))
6-C1 4- CH 3 H. - (CH2) 2-CHOCH3 O C2H5 199-202 ß o or (CH2) 2-
4- CH3 6- CH3 H CH3 CH3 O C2H5 * 4.03 ppm (q, 2H, O- - 10 CH2), 1.51 ppm (s,
6H, C (CH3) 2), 0.81
0.74, 0.64, 0.55 ppm 15 (in each case m, 1H, CH2 (cyclopropyl))
No. of pf ° C Isomer Ex
Ilc- 1 2-CH 3 6- CH 3 H (CH 2) 2-0- (CH 2): ¾H 5 210 11 Il-1 6-Cl 4 CH 3 H CH 2 CH 5 Cl 5 H 5 188-189 ß 12 (CH 2) 3- Il - - 2 4- CH3 HH CH3 CH3 C2H5 * 4.05 ppm (q, 2H, - 13 OCH2), 1.51 ppm (s, 6H, C (CH3) 2), 0.79 ppm (m, 4H, CH2 (cyclopropyl)), 0.70 and 0.59 ppm (in each case m, 2H, 15 CH2 (cyclopropyl)) 4- CH3 6- CH3 H -CH2-CHOC2H5 O C2H5 236-237 ß 14
No. of m J X Y D A B M R pf ° C Isomer Ex
14 (CH2) 3- Il- 1 6-C1 4- CH3 H -O ^ -CHC ^ - O C¾ 230-231 ß 15 (H2) 3- Ilc- 1 4- CH3 6- CH3 H -CH2-CHOC4H9 O C2H5 173 ß 16 (CH2) 3-
4- CH3 6- CH3 H -CH2-CHOC4H9 O C¾ 180-183 ß 17 L O
2, ^ 0 4- CH3 H H O O C2H5 155-156 18
2ß- < ] 4"ffl3 H H - (CH2) 2-CHOCH3 O C2H5 205-208 ß
(CH2) 2-
I-l-c 4- Cl 6- CH 3 H - (CH 2) 2 -CHOCH 3 O C 2 H 5 176-177 ß 15 (CH 2) 2-
4? < ^ 6-C2H5 H H CH3 CH3 O C2H5 167-168
n ° of m J Y D A B M R2 pf ° C Isomer Ex 21
I-1-C-2 2 - < ] 6_C2H5 H H "(H2) 2-CHOCH3 O C2H5 * 4.05 ppm (q, 2H, O- ß
22 (GH2) 2- CH2),
3.40 ppm (s, 3H, O-CH3),
0.81 (m, 4H, CH2
(cyclopropyl)), or
0.61, 0.60 ppm (in each case m, 2H, CH2
(cyclopropyl)) I-1-c-2 2i 4? j 6-C2H5 HH - (CH2) 2-CHOCH3 O CH3 * 3.63 ppm (s, 2H, ß 23 (CH2) 2- COO-CH3), 3.40 ppm 15 (s, 3H, O-CH3) ,
0.92 (m, 2H, CH2
n ° of m J X Y D A B M R2 pf ° C Isomer Ej (cyclopropyl)), 0.82 - 0.55 ppm (wide accumulation 5 of signals, 6H, C¾
(cyclopropyl))
n. of m B M R2 pf ° C Isomer o
Ex 10 Il-6-C2H5 4- CH3 (CH2) H 0 C2H5 * 4.75 ppm (m, 1H, CH-N-24 (bridgehead)), 4.19 ppm (dg, 2H, 0-CH2 ),
0.95 - 0.54 ppm
(wide accumulation of signals, 4H, C¾
(cyclopropyl))
of m J X Y D A B M R2 f Isomer
c- 1 2- < ] 6_C2H5 4- CH3 H CH3 CH 0 CH3 * 3.63 ppm (s, 2H, 0-CH3), 3.51 ppm (s, 6H, (CH3) 2), 0.78 (m, 2H, CH2 (cyclopropyl)), 0.67, 0.59 ppm (in each case m, 1H, (_¾ (cyclopropyl)) * 1 H NMR (400 MHz, CDCl 3): displacements d in ppm
Initially 0.15 g (0.415 mmol) of the compound of Example I-20, 0.07 ml of triethylamine and 1.5 mg of DMAP in 10 ml of chloroform are charged, the mixture is stirred at room temperature for 10 minutes and added 0.04 ml of methanesulfonyl chloride. The mixture is stirred at room temperature for about 18 h. After the reaction is complete, the mixture is poured into 5 ml of 5% sodium bicarbonate solution and stirred at room temperature for 10 minutes. The organic phase is removed by separation and dried over Na 2 SO 4, and the solvent is removed under reduced pressure using a rotary evaporator. The residue is purified by column chromatography (ethyl acetate / n-heptane 1: 1). Yield: 0.082 g (45% of theory) NMR of XH (400MHz, CDC13): d = 0.67, 0.89 ppm (2m, in each case 2H, CH2-cyclopropyl), 2.57 ppm (s, 3H) , SO2-CH3),
3.40 ppm (s, 3H, O-CH3).
Analogously to Example (I-1-d-1), one obtains
Isomer ß NMR of H. (400MHz, CDCl 3): d = 3,40 ppm (s, 3H, 0-CH 3),
2.47 ppm (s, 3H, S02-CH3), 0.87, 0.81, 0.67, 0.62 ppm (in each case m, 1H, CH2 (cyclopropyl)). Example II-l
1 g of the compound of Example (XXX-2) is dissolved in 30 ml of dichloromethane, 2 drops of N, N-dimethylformamide and 0.76 g of oxalyl chloride are added and the mixture is heated to boiling under reflux for 2 hours. until the gas evolution is over, concentrate, take twice in 20 ml of dichloromethane in each case, concentrate again and take in 20 ml of dichloromethane (solution 1). Initially, 0.7 g of 1- hydrochloride are charged
Methyl aminoisobutylate in 30 ml of dichloromethane, 0.97 g of triethylamine are added, the mixture is stirred at room temperature for 15 minutes, then solution 1 is added dropwise over a period of 30 minutes, the mixture is stirred at At room temperature overnight, 30 ml of water are added, the mixture is stirred for 20 minutes and the organic phase is separated off, dried and purified by chromatography on silica gel (gradient of ethyl acetate / heptane 5: 95 to 100: 0). This gives 1.05 g of a colorless solid (yield 72% of theory), mp: 127 ° C.
Analogously to Example (II-1) and according to the general guidelines on the preparation, the following compounds of the formula (II) are obtained:
# M J X Y D A B R8 pf ° C Isomer of Ex. II-2 1 4. ^ j 2-C2H5 6-CH3 H - (O-2) 2-CH0CH3- (CH2) 2- 123 ß
II-3 1 4 __ ^ j 2-C2H5 6-CH3 H -CH2-CHOC4H9- (CH2) 3- CH3 * 2.89 (m / lH, ß CHO CH2) 3.58 (s, 2H, Ar-CH2- CO) II-4 1 4 ._ ^ j 2 -CH 3 6 -CH 3 H - (CH 2) 2 -CHOCH 3 - (CH 2) 2 - CH 3 * 3,12 (m, 1 H, β CHO CH 3) 6.80 (s) , 2H, Ar-H) II-5 1 2-] 6_C2H5 4-CH 3 H CH 3 CH 3 CH 3 114
No. X Y D A B pf ° C Isomer of Ex. II-6 6-C2H5 4-CH3 H - (aí2) 2-CHOCH3- (CH2) 2- CH3 96-98 ß
II-7 4- CH 3 6-CH 3 H - (CH 2) 2-CHOCH 3 - (CH 2) 2 - CH 3 * 3.12 (m, 1 H, β CHO CH 3) 3.80 (m, 2H,
Ar-CH2-CO)
II-8 4- CH 3 6-CH 3 H CH 3 CH 3 CH 3 * 1, 43 (s, 6H, 0 (013) 2) 3.68 (s, 2H, 10 Ar-CH 2 -CO)
II-9 4- CH3 6-CH3 H-CH2-CHOC2H5- (CH2) 3- CH3 * 2.99 (m, lH / a? (?? 2-?
) 11-10 2-CH3 6-CH3-CH2-CHOC2H5- (CH2) 3- CH3 131 ß
11-11 2- CH3 6-CH3 H - (CH2) 2-0- (CH2) 2- CH3 189
11-12 2-CH3 6-CH3 H CH2-OCH3 CH3 156 ß I - (CH2) 2-CH- (CH2) 2-
No. m J X? B pf ° C Isomer of Ex 11-13 2 4-CH3 H H - (CH2) 2-CHOCH3- (CH2) 120 ß
11-14 2 2.6-] 4_CH3 H H CH3 CH3 118-119
11-15 1 4-CH3 6-CH3 H -CH2-CHOC4H9- (CH2) 3- directly ß react more 10 11-16 1 2-? < ] 6-C2H5 4-CH3- (CH2) 3- H CH3 * 4.52 ppm (m, 1H, -CH-N), 0.85 (m, 2H, CH2 (cyclopropyl)), 0.62 ppm ( m, 2H, 15 CH2 (cyclopropyl))
# M J X Y D A pf ° C Isomer of Ex II 2-CH 3 6-CH 3 H - (CH 2) 2-C- (CH 2); 174 / \ O O 5 11-18 1 2- < ] 4-C1 6-CH3 H - (CH2) 2-CHOCH3- (?? 2) 2- CH3 129-131 ß
11-19 1 2 ._ ^ | 6-C1 4-CH3 H CH3 CH3 CH3 122-123
11-20 1 2-? < ] 6-C1 4-CH3 H - (a? 2) 2-80a? 3- (a? 2) 2- H3 129-131 ß w tO
11-21 1 2. ^ j 6-C1 4-CH 3 H -CH 2 -CHOC 4 H 9 - (CH 2) 3- < ¾ 100-101 ß
fifteen
n. ° J X Y D A B pf ° C Iscnero of Ej 11-22 1 2-- < ] 6-C1 4-CH3 H-CH2-CHOC2H5- (CH2) 3- CH3 * 3.68 ppm (s, 3H, ß OCH3), 3.41 ppm (m, 2H, 0C¾), 0.99 and 0 , 66 (in each case m, 2H, C¾ (cyclopropyl)) 11-23 2 24 ^ 6-C2HB CH3 CH3 CH3 124-125
11-24 2 2, -] 6-C2H5 - (CH2) 2-CHOCH3- (CH2) 2- CH3 - ß
11-25 2 2.6- < ] _CH3 ^ CH3 CH3 * 3.70 ppm (s, 3H, - COO-CH3), 1.37 ppm (s, 3H,
n. ° m J X Y D A B pf ° C Isomer of Ej CH3),
1.89 ppm (m, 2H, Ar-CH (cyclopropyl)) 11-26 6-CH 3 H H CH 3 * 1.42 ppm (s, 6H, - (CH 3) 2C-NH), 3.80 ppm
(s, 2H, Ar-CH2-CO)
11-27 1 4__ < J 4-CH 3 6-CH 3 - (CH 2) 3- H CH 3 * 4.18 ppm (m, 2H, O- - 3 H 2), 3.95 and 3.81 ppm (in each case m, together 1H , CH-O), 0.94 and 0.67 (in each case m, 2H, CH2
(cyclopropyl)) * 1 H NMR (400 MHz, CDCl 3): displacements d in ppm
(III-l)? -2-a-l I- 2-a-2
Initially, 0.59 g (1.466 mmol) of the compound of Example (III-1) is charged in 10 ml of DF, 0.247 g (2.199 mmol) of potassium tert-butoxide are added and the mixture is stirred at room temperature for 12 hours. h. The DMF is removed using a rotary evaporator, the residue is partitioned between water and methyl tert-butyl ether, the aqueous phase is acidified with hydrochloric acid, the product is extracted with dichloromethane and the organic phase is dried and concentrated using a rotary evaporator. For further purification and separation of the isomers, 0.37 g of the crude product is chromatographed on silica gel RP18 (acetonitrile / water). Yield: 89 mg? -2-a-l (17% of theory), logP = 2.81 132 mg I-2-a-2 (25% of theory), logP = 3.07
Analogously to the Examples (? -2-a-1) and (I-2-a-2) and in accordance with the general guidelines on the preparation, the following compounds of the formula (I 2-a) are obtained:
n. "m AB logP Ex Isomer 1-2- 1 2-CH3 - (CH2) 2-CHOCH3- 2.64 cis a-3 CH- (CH2) 2- 1-2- 1 - (CH2) 2-CHOCH3- 2.88 trans
a-4 CH3 (CH2) 2- 1-2- 1 -O2-CH3 6- - (CH2) 2-0- (CH2) 2- 2.36 a-5 CH-
Initially 50 mg (0.14 mmol) of the compound of Example 2 -2-a are charged in 5. ml of dichloromethane, 17 mg (0.168 mmol) of triethylamine and 20 mg (0.168 mmol) of pivaloyl chloride are added and the The mixture is stirred at room temperature for 12 h. The mixture is concentrated and the crude product is purified by chromatography on silica gel RP18 (acetonitrile / water). Yield: 60 mg (97% of theory), logP = 5.03 Example (III-l)
With a bath temperature of 120 ° C, 0.854 g (4.224 mmol) of ethyl 4-methoxy-l-hydroxy-cyclohexanecarboxylate and 1 g (4.224 mmol) of 2-cyclopropyl-6-ethyl chloride are stirred.
4-Methyl-phenylacetyl for 6 h and, after cooling, is degassed in a rotary evaporator, the residue is dissolved in methyl tert-butyl ether and washed with 5% aqueous sodium hydroxide solution and the organic phase is dried and concentrated using a Rotavapor Yield: 0.59 g (35% of theory), oil, logP =
, 15 Example? -6-a-l
Initially 0.58 g (1.7 mmol) of the compound of Example VIII-1 and 0.38 g of potassium tert-butoxide (3.4 mmol) in 10 ml of anhydrous DMF are charged and heated to 50 ° C. for 3 h. After cooling, the mixture is added to ice water, acidified to pH 2 using 2 N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed twice with water, dried (sodium sulfate) and concentrated using a rotary evaporator. Chromatography on silica gel using hexane / ethyl acetate (v / v = 70: 30) gives 286 mg (54%) of the compound of Example 6-a-1 as colorless crystals. mp 189-190 ° C
RN of * H (d5-D SO, 400 MHz): d = 0.45 and 0.67 (in each case I, in each case 1H), 1.38 and 1.62 (in each case I, in each case) case 2H), 1.80 (me, 1H), 2.22 (s, 3H) Example VIII-1
1.50 g (4.6 mmol) of the compound of Example XXXVII-1 are boiled in 30 ml of acetone, 1.30 g of potassium carbonate and 1.96 g (13.8 mmol) of iodomethane at reflux for 4 hours. it is then taken up in ethyl acetate, stirred with water and dried (magnesium sulfate), and the solvent is distilled off. Chromatography on silica gel using ethyl acetate / hexane (v / v = 70:30) provides 1.23 g (78%) of the compound of the formula (VIII-1) as a colorless solid of mp 84-85 °. C. Example XXXVII-1
At -30 ° C, 3.38 g (13.9 mmol) of 2-cyclopropyl-
Methyl 6-ethyl-4-methylphenylacetate slowly dropwise to a solution of lithium diethylamide, prepared from 3.5 g of diethylamine in 25 ml of THF, and 14 ml of a 2.5 molar solution of n- butyl lithium in hexane, and the mixture is stirred at room temperature for another 30 minutes. Then 2.15 g (13.9 mmol) of cyclohexane-1,2-dicarboxylic anhydride, dissolved in 10 ml of THF, are added at -20 ° C, and the mixture is stirred at room temperature for 12 h. The addition of 30 ml of saturated ammonium chloride solution, covering with a layer of ethyl acetate, washing with water, drying (magnesium sulfate) and concentrating using a rotary evaporator provides approximately 5.4 g of a solid to which, without Further purification, 2.2 g of potassium hydroxide in 50 ml of water are added, and the mixture is refluxed for 24 h. The mixture is then acidified to pH 2 using 2N hydrochloric acid, and the resulting precipitated solid is removed by suction filtration. This gives 1.68 g (37%) of the compound of the formula (XXXVII-1) in the form of yellowish crystals with mp 187-188
Example? -8-a-l
Initially 0.982 g (9 mmol) of potassium tert-butoxide are charged in 35 ml of anhydrous N-dimethylformamide. Then 1.1 g of the compound of Example XII-1 in N, N-dimethylformamide is added dropwise, and the mixture is stirred at 80 ° C for 2 h. Ice water is added and the mixture is acidified to pH 1 using concentrated hydrochloric acid and extracted with methylene chloride, and the extract is dried and concentrated under reduced pressure using a rotary evaporator. Yield: 0.75 g (? 86% of theory)! NMR data of JH in CDCI3, 400 MHz: d = 3.75-3.60 (m, 4H); 2.30-2.20 (m, 2H); 1.85-1.75 (m, 4H); 1.55 (m, 1 cyPr-H); 0.90 (m, 1 cyPr-H); 0.85 (m, 1 cyPr-H); 0.75 (m, 1 cyPr-H); 0.65 (m, 1 cyPr-H) ppm.
Example? -8-b-l
Initially 0.15 g (0.5 mmol) of the compound of Example? -8-al and 0.113 g (1 mmol) of potassium carbonate in tetrahydrofuran are charged, and isobutyl chloride (0.04 ml) is added at room temperature. . After a reaction time of 3 h, the solvent is evaporated under reduced pressure, water is added to the residue, the mixture is extracted with ethyl acetate and the extract is again concentrated under reduced pressure. Yield: 0.12 g (? 70% of theory) l-NMR data of * H in CDCl3, 400 MHz: d = 6.85 (s, 1H); 6.55 (s, 1H); 3.90 (m, 1H), 3.80 (m, 1H); 3.35 (m, 2H); 2.65-2.55 (m, 2H); 2.50 (Sept. 1H); 2.25 (s, 3H); 1.95 (m, 2H); 1.85 (m, 2H); 1.80 (m, 1 cyPr-H); 1.15 (tr, 3H); 1.05 (m, 6H) 0.75 (m, 2 cyPr-H); 0.60 (m, 1 cyPr-H); 0.55 (m, 1 cyPr-H) ppm.
Analogously to the Example (? -8-b-l), the
Example (I-8-b-2)
l-NMR data of XH in CDCl 3, 400 MHz: d = 6.85 (s, 1H); 6.50 (s, 1H); 3.90 (m, 1H), 3.80 (m,
1H) 3.35 (m, 2H) 2, 60-2, 40 (m, 2H); 2.25 (s, 3H); 1.95 (m, 2H) 1.85 (m, 2H); 1.80 (m, 1 cyPr-H); 1.15 (tr, 3H); 1.05 (s, 9H) 0.80 (m, 2 cyPr-H); 0.60 (m, 1 cyPr-H); 0.55 (m, 1 cyPr-H) ppm
Analogously to Example? -8-b-l, lo? -8-c-l is obtained
! -NHR NMR data in CDCI3, 400 MHz: d = 6.90 (s, 1H); 6.60 (s, 1H); 4.15 (q, 2H)
(m, 2H), 3.40 (tr, 2H); 2.65-2.45 (m, 2H); 2.25 (s, 3H); 1.95 (m, 2H); 1.85 (m, 2H); 1.80 (m, 1 cyPr-H); 1.20 (tr, 3H); 1.15 (tr, 3H); 0.75 (m, 2 cyPr-H); 0.65 (m, 1 cyPr-H); 0.55 (m, 1 cyPr-H) ppm. Example XII-1
In anhydrous tetrahydrofuran, 2.28 ml (16 mmol) of triethylamine are added to 1.7 g (8 mmol) of the compound of Example XXX-3, 2.46 g (11 mmol) of ethyl hexahydropyridazinecarbazate are added, after 10 minutes a further 2.28 ml (16 mmol) of triethylamine is added dropwise, followed immediately after the dropwise addition of 0.73 ml (8 mmol) of phosphorus oxychloride. The solution is refluxed for 30 minutes, the solvent is removed, the residue is taken up in methyl acetate and the mixture is washed twice with water, dried and concentrated. The residue is taken up in n-heptane and filtered through a little silica gel. The filtrate is concentrated. Performance: 2.3g (? 74% of theoretical)
l-R N data of H in CDCl 3, 400 MHz: d = 6.85 (s, 1H); 6.75 (s, 1H); 4.55 (dbr, 1H); 4.30-4.20
(mbr, 3H); 4.00 (d, 1H); 3.80 (d, 1H), 2.95 (mbr, 1H); 2.75
(trbr, 1H); 2.55 (q, 2H); 2.25 (s, 3H); 1.80 (m, 1 cyPr-H);
1.75-1.60 (mbr, 4H); 1.15m (tr, 3H); 0.90-0.75 (m, 2 cyPr-H); 0.70-0.55 (m, 2 cyPr-H) ppm. Example XXX-1
Initially, 4.8 g of the compound of Example (XXXIV-2) are charged to 200 ml of tetrahydrofuran, 0.5 of lithium hydroxide is added, dissolved in 80 ml of water, and the mixture is stirred at room temperature for approximately 70 minutes. h. The tetrahydrofuran is removed using a rotary evaporator, using 1 N HC1, the aqueous phase is adjusted to pHl, then the aqueous phase is stirred at room temperature for 10 minutes and the precipitate is filtered off with suction through a grinding wheel. The residue is dissolved in ethyl acetate, the mixture is dried over sodium sulfate and concentrated using a rotary evaporator, the residue is taken up in 30 ml of n-heptane, the mixture is treated with ultrasound during
minutes and it is removed by filtration with suction through a grinder, and the product is dried. This gives 4.0 g of a colorless solid (yield 89% of theory), mp: 138 ° C.
Analogously to Example (XXX-1) and according to the general guidelines on the preparation, the following compounds of the formula (XXX) are obtained:
(J) m
n. ° of m X pf ° C Ex
XXX-6 1 6-CH3 4-C1 224-226
0.93, 0.62
n. ° of m pf ° C Ex (2m, 4H, CH2 (cyclopropyl))
XXX-9 2 4-CH 3 H * 4,18 (s, 2H,
CH2C02) 0.91, 0.64 (2m, 4H, CH2 (cyclopropyl)) * H NMR (400 MHz, CDC13): displacements d in ppm Example XXXIV-1
Initially 3 g of methyl 4-bromo-2-ethyl-6-methylphenylacetate are charged to 115 ml of toluene and 5.7 ml of water, and the apparatus is washed 3 times with vacuum / argon. Then 1.24 g of cyclopropamboronic acid, 5.27 g of
potassium dihydrogen phosphate, 0.31 g of tricyclohexylphosphine and 0.12 g of palladium acetate, and the mixture is heated to reflux in a preheated oil bath. The mixture is stirred at reflux for 8 h. The mixture is poured into 500 ml of 0.5 N HC1 and extracted 3 times with 150 ml of toluene, the organic phases are combined and washed with 100 ml of sodium chloride solution, after separation of the phases, organic phases are dried over Na2SC > and concentrate using a rotary evaporator. The residue is separated in a Biotage chromatography station using ethyl acetate / n-heptane (5:95 to 100: 0). This provides 2.5 g of an oily residue (98% of theory). * XH NMR (400 Hz, CDC13): d: 1.81 (m, 1H, CH-cycPr),
3.66 (s, 2 + 3H, CH2-COOCH3) ppm. Analogously to Example (XXXIV-1) and in accordance with the general guidelines on the preparation, the following compounds of the formula (XXXIV) are obtained: (J) m (XXXIV)
.0 of m J X Y R 8 n '° c Ex XXXIV-2 1
n. ° of m J X and R8 pf ° C Ex CH3 3, 64 (s, 2H, CH2C02CH3) 3.67 (s, 3H, CH2-C02CH3)
XXXIV-3 1 2? < ^ | 6 ~ 4 ~ CH3 * 1.89 (m 'lH, CH-cyc-Pr) C2H5 CH3 3.89 (s, 2H, CH2C02CH2CH3) 4.13 (s, 3H, C02CH2CH3)
XXXIV-4 1 2? / J 4-CH3 6- CH3 was converted without CH3 further characterization in Example (XXX-4) XXXIV-5 1 ^ 2-C1 4- CH3 * 1.86 (m, 1H, CH- cyc-Pr) CH3 3.69 (s, 3H, C02CH3)
XXX! V-6. ^ 4-C1 6- CH3 .3.88 Ppm «s, 2". C "2- CH3COO), 3.68 ppm (s, 3H, OCH3), 0.93 and 0.62 ppm (in each case m, 2H, CH2 (cyclopropyl)) XXXIV-7 2 CH2-
OCH 3), 0.90 ppm (m, CH 2 (cyclopropyl)),
n. ° of m X pf ° C Ex 0.66 and 0.60 ppm (in each case m, 2H, CH2 (cyclopropyl)) XXXIV-8 2 4-CH3 H CH3 * 4.12 ppm (s, 2H, CH2- > 6] COO), 3, 68 ppm (s, 3H, OCH3), 0.89, and 0.62 ppm (in each case m, 4H, CH2 (cyclopropyl)) XXXIV-9 2
OCH3), 0.89 ppm (m, 4H, CH2 (cyclopropyl)), 0.66 and 0.60 ppm (in each case m, 2H, CH2 (cyclopropyl))
* RN of 1R (400 MHz, CDC13): displacements d in ppm The logP values given in the table were determined according to EEC Directive 79/831 Annex V.A8 by HPLC (High Resolution Liquid Chromatography ) on a reverse phase column (C18). Temperature:
43 ° C. Mobile phases for the determination in the acid interval (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient of 10% acetonitrile to 90% acetonitrile. Calibration was performed using unbranched alcan-2-ones
(having 3 to 16 carbon atoms) with known logP values (the determination of the logP values was carried out according to the retention times using linear interpolation between two successive alkanones). The lambda max values were determined for the maximum of the chromatographic signals using the UV spectra from 200 nm to 400 nm.
Example A Preemergence herbicidal action Seeds of weeds and monocotyledonous and dicotyledonous crop plants are introduced into sandy substrate in wooden fiber pots and covered with soil. The test compounds, formulated in the form of wettable powders (WP) or in the form of emulsion concentrates (EC), are then applied in the form of an aqueous suspension with an application rate in water of 800 1 / ha (converted) , with 0.2% wetting agent added, to the surface the coating earth. After the treatment, the pots are introduced in a
greenhouse and are kept in good growing conditions for the test plants. The visual evaluation of the damage in the emergence of the test plants is done after a trial period of 3 weeks compared to the untreated controls (effect of the herbicide in percentage (%): 100% effect = the plants have died, 0% effect = same as the control plants). Here, the following compounds, for example, controlled Lolium multiflorum and Setaria viridis at an application rate of 320 g / ha with >; 80% efficiency: Example: Ila-5, Ila-6, Ila-7, Ila-8, Ila-10, Ila-11, Ila-12, Ila-14, Ila-15, Ila-17, Ila-18 , Ila-19, Ilb-1, Ilb-2, Ilb-6, Ilb-9, Ilb-10, Ilc-1, Ilc-2, Ilc-7, Ilc-8, Ilc-10, Ilc-12, Ilc -13, Ilc-14, Ilc-15, Ilc-16, Ilc-17 Example B Post-emergence herbicide action Seeds of weeds and monocotyledonous and dicotyledonous cultivation plants are introduced into sandy substrate in wooden fiber pots, covered with and cultivated in a greenhouse under good growing conditions. Two to three weeks after sowing, the test plants are treated when they are in the state of a leaf. The test compounds, formulated in the form of wettable powders (WP) or in the form of emulsion concentrates
(EC), are then sprayed, in the form of an aqueous suspension with an application rate in water of 800 1 / ha
(converted), with 0.2% wetting agent added, on the green parts of the plants. After having maintained the test plants in the greenhouse under optimal culture conditions for approximately 3 weeks, the effect of the preparations is evaluated visually compared to the untreated controls (effect of the herbicide in percentage (%): 100% effect = the plants have died, 0% effect = same as the control plants). Here, the following compounds, for example, controlled Lolium multiflorum and Setaria viridis at an application rate of 320 g / ha with > 90% efficiency: Example: I-l-c-1. Here, the following compounds, for example, controlled Lolium multiflorum and Setaria viridis at an application rate of 80 g / ha with > 80% efficiency: Example: Ila-2, Ila-5, Ila-6, Ila-7, Ila-8, Ila-10, Ila-11, Ila-12, Ila-14, Ila-15, Ila-17 , Ila-18, Ila-19, Ilb-1, Ilb-ß, Ilb-9, Ilb-10, Ilc-3, Ilc-7, Ilc-8, Ilc-10, Ilc-13, Ilc-14, Ilc -15, Example C Post-emergence herbicidal action Seeds of weeds and monocotyledonous and dicotyledonous cultivation plants are introduced into sandy substrate
In wooden fiber pots or in plastic pots, they are covered with earth and grown in a greenhouse, during the period of vegetation also outdoors outside the greenhouse, in good growing conditions. Two to three weeks after sowing, the test plants are treated when they are in the one to three leaf condition. The test compounds, formulated in the form of wettable powders (WP) or liquid (EC), are sprayed, in various doses at an application rate in water of 300 1 / ha (converted), with a wetting agent (0.2 a 0.3%) added, on the plants and the surface of the earth. Three to four weeks after the treatment of the test plants, the effect of the preparations is evaluated visually compared to the untreated controls (effect of the herbicide in percentage (%): 100% effect = the plants have died, 0% of effect = same as the control plants). Use of safeners If you also need to analyze how safeners can improve the compatibility of plants with test substances in the case of crop plants, the following options are used during the application of the safener: the seeds of the crop plants are covered with safener substance, before sowing (the amount of safener is expressed as a percentage, based on the total weight of the seed)
before the application of the test substances, the crop plants are sprayed with the safener at a certain rate of application per hectare (usually 1 day before the application of the test substances) - the safener is applied together with the substance of test in the form of tank mix (the safener is expressed in g / ha or in terms of proportion, based on the herbicide). By comparing the effect of test substances on crop plants without or with safener treatment, the effect of the safener substance can be evaluated. Tests in the greenhouse, treatment with safener 1 day before the application of herbicide
I-l-a-5 + mefenpir 50 + 100 60 15 25 + 100 40 10 12, 5 + 100 20 0
days 28 days after the after
Table 2 application application Proportion of application Summer wheat Summer wheat observation observation g of a. i. / ha (%) (%) Ila-5 50 70 75 25 70 60 12, 5 60 40 6,25 50 10 Ila-5 + mefenpir 50 + 100 40 25 25 + 100 20 20 12,5 + 100 10 5 6 , 25 + 100 3 0
days after the
Table 3 application Proportion application Summer wheat observation g of a. i. / ha I-l-a-12 25 50 12, 5 40 6, 25 10
I-l-a-12 mefenpir 25 + 100 20 12.5 + 100 15 6.25 + 100 0
28 days after the
Table 5 application Proportion of application Summer barley Summer wheat observation observation g of a. i. / ha (%) (%) I-1-a-14 100 85 50 70 75 25 60 50 12, 5 20 20
I-l-a-14 + mefenpir 100 + 100 40 50 + 100 30 30 25 + 100 25 20 12.5 + 100 5 5
days 28 days after the after
Table 6 application application Proportion of application Summer barley Summer barley observation observation g of a. i. / ha (%) (%) I-1-a-18 100 35 20 50 25 10 25 15 12, 5 10
I-l-a-18 + mefenpir 100 + 50 20 5 50 + 50 15 5 25 + 50 10 12,5 + 50 5
days after the
Table 7 application Proportion of application Summer wheat observation g of a. i. / ha I-l-a-18 100 40 50 25 25 15 12, 5 10
I-l-a-18 mefenpir 100 + 50 10 50 + 50 5 25 + 50 5 12.5 + 50 0
days after the
Table 8 application Proportion application Summer barley observation g of a. i. / ha I-l-a-7 50 60 25 50 12, 5 10
I-l-a-7 mefenpir 50 + 100 40 25 + 100 10 12.5 + 100 7
28 days after the
Table 9 application Application rate Summer wheat observation g of a. i. / ha I-l-a-7 100 80 50 70 25 60 12, 5 30
I-l-a-7 mefenpir 100 + 100 50 50 + 100 40 25 + 100 20 12,5 + 100 10
days after the
Table 10 application Application rate Summer wheat observation g of a. i. / ha (%) I-1-a-8 100 30 50 30 25 25
I-l-a-8 mefenpir + 100 + 100 + 100
days 28 days after the after
Table 11 application application Application rate Summer wheat Summer wheat observation observation g of a. i. / ha (%) (%) I-l-a-9 25 65 50 12, 5 60 I-l-a-9 + mefenpir 25 + 100 50 25 12.5 + 100 15
I-l-b-1 + mefen go 50 + 100 30 25 + 100 30 15 12,5 + 100 5 0
days 28 days after the after
Table 13 application application Application rate Summer wheat Summer wheat observation observation g of a. i. / ha (%) (%) I-l-b-1 100 95 50 90 25 60 40 12, 5 50
I-l-b-1 + mefenpir 100 + 100 40 50 + 100 20 25 + 100 25 0 12.5 + 100 15
days 10 days after the after
Table 14 application application Proportion of application Summer barley Summer wheat observation observation g of a. i. / ha (%) (%) I-l-c-13 50 30 40 25 20 30 12, 5 5 20
I-l-c-13 + mefenpir 50 + 50 10 30 25 + 50 5 20 12,5 + 50 0 5
days 28 days after the after
Table 15 application application Proportion of application Summer barley Summer barley observation observation g of a. i. / ha (%) (%) I-l-c-7 100 90 95 50 60 50 25 40 12, 5 10
I-l-c-7 + mefenpir 100 + 100 50 25 50 + 100 10 5 25 + 100 3 12.5 + 100 0
days 28 days after the after
Table 16 application application Application rate Summer wheat Summer wheat observation observation g of a. i. / ha (%) (%) I-l-c-7 50 80 25 60 20 12, 5 20 10
I-l-c-7 + mefenpir 50 + 100 20 25 + 100 30 10 12.5 + 100 10 5
Example D Test in Phaedon (spray treatment) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent and emulsifier indicated, and the concentrate is diluted with water with emulsifier to the desired concentration. Chinese cabbage discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, infected with larvae of the mustard beetle (Phaedon cochleariae). After the desired period of time, the effect is determined as a percentage 100% means that all beetle larvae have died; 0% means that none of the beetle larvae have died. In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g / ha, an efficacy of > 80%: Example: Ila-2, Ila-4, Ila-6, Ila-7, Ila-10, Ila-11, Ila-12, Ila-14, Ila-24, Ila-25, Ilb-5, Ilb -11, Ilb-13, 1-1-c-7, Ilc-12, Ilc-20, Ilc-22, Ilc-23, Ild-1, N. Example E 'Test in Myzus (spray treatment MYZUPE) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether.
To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent and emulsifier indicated, and the concentrate is diluted with water with emulsifier to the desired concentration. Discs of Chinese cabbage. { Brassica pekinensis) that are infested by all phases of the green peach aphid (Myzus persicae) are sprayed with a preparation of the active compound of the desired concentration. After the desired period of time, the effect in percentage is determined. 100% means that all aphids have died; 0% means that none of the aphids has died. In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g / ha, an efficacy of > 90%: Example: 1-1-a-2, I-l-a-4, I-l-a-β, I-l-a-7,
Ila-9, Ila-11, Ila-12, Ila-14, Ila-15, Ila-17, Ila-20, Ila-22, Ilb-3, Ilb-4, Ilb-ß, Ilb-10, Ilb- 13, Ilc-1, Ilc-8, Ilc-9, Ilc-14, Ilc-15, Ilc-19, N. Use of F test in Te ranychus, resistant to OP (TETRUR spray treatment) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide
Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvents and emulsifier indicated, and the concentrate is diluted with water with emulsifier to the desired concentration. Disks of bean leaves (Phaseolus vulgaris) that are infested by all phases of the greenhouse red spider (Tetranychus urticae) are sprayed with a preparation of the active compound of the desired concentration. After the desired period of time, the effect is determined as a percentage 100% means that all the spiders have died; 0% means that none of the spiders has died. In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 g / ha or 20 g / ha *, an efficiency of > 80%: Example: Ila-4, Ila-5, Ila-6, Ila-7, Ila-8, Ila-9, Ila-10, Ila-11, Ila-14, Ila-17, Ila-19, Ila -20, Ila-25 *, Ilb-4, Ilb-8, Ilb-9, Ilb-13, Ilb-15, Ilc-9, Ilc-12, Ilc-13, 1-1-c-14, Ilc- 15, Ilc-16, Ilc-20, Ilc-25, Ild-1,? -8-b-2.
N. ° of Ej. G Test in Myzus persicae, hydroponic treatment (sis.
MYZUPE) Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent and emulsifier indicated, and The concentrate is diluted with water to the desired concentration. The active compound preparation is mixed with water. The concentration reported refers to the amount of active compound per unit volume of water (mg / 1 = ppm). The treated water is loaded into containers containing a pea plant. { Pisum sativum) that later becomes infested with the green peach aphid. { Myzus persicae). After the desired period of time, the effect is determined in percentage 100% means that all the aphids have died; 0% means that none of the aphids has died. In this test, for example, the following compound of the Preparation Examples shows, at a concentration of 20 ppm, an efficacy of > 90%: Ex. I-1-a-4. . ° of Ej. H Meloidogyne test (MELGIN spray treatment) Solvent: 80 parts by weight of acetone
To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amount of solvent and the concentrate is diluted with water to the desired concentration. Fill containers with sand, active compound solution, egg suspension and Meloidogyne larvae incognita lettuce seeds. Lettuce seeds germinate and plants develop. In the roots, galls form. After the desired period of time, the action of the nematicide in% is determined according to the formation of galls. 100% means that no guts were found; 0% means that the number of galls of the treated plants corresponds to that of the untreated control. In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 20 ppm, an efficiency of = 80%: Example: I-1-a-7, I-1-a-12. No. of Ex. I Test in Lucilia cuprina (LUCICU) Solvent: Dimethyl sulfoxide To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amount of solvent and the concentrate is diluted with water to the desired concentration. Containers that contain talking horse meat
been treated with the active compound preparation of the desired concentration are colonized with Lucilia cuprina larvae. After the desired period of time, the effect is determined in percentage 100% means that all the larvae have died; 0% means that none of the larvae has died. In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 ppm, an efficiency of = 80%: Example: I-1-a-4, I-1-b-4, I-1-c-3. N. of E. J Test in Boophilus microplus (BOOPMI injection) Solvent: Dimethyl sulfoxide To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amount of solvent and the concentrate is diluted with solvent to the desired concentration. The active compound solution is injected into the abdomen (Boophilus microplus), the animals are transferred to plates and stored in a heated room. After the desired period of time, the effect is determined in a percentage of 100%, meaning that none of the ticks has laid fertile eggs. In this test, for example, the following compounds of
The Preparation Examples show, at an application rate of 20 g / animal, an effect of = 80%: Example: 1-1-a-1, Ila-2, Ila-4, Ila-6, Ilb-4, Ilc-3. Example K Critical concentration test / soil insects - treatment of transgenic plants Test insect: Diabrotica balteata - larvae in the soil Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce an adequate preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent indicated, the amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. The preparation of active compound is poured on the ground. Here, the concentration of active compound in the preparation is practically irrelevant, only the amount by weight of active compound per unit volume of soil, which is expressed in ppm (mg / 1), matters. The soil is placed in 0.25 1 pots, and these are allowed to stand at 20 ° C. Immediately after the preparation, 5 grains of pregerminated corn of the variety YIELD GUARD (trademark of Monsanto Comp., USA) are introduced in each pot.
After 2 days, the appropriate test insects are introduced into the treated soil. After another 7 days, the effectiveness of the active compound is determined by counting the maize plants that have emerged (1 plant = 20% activity). Example L Test in Heliothis virescens - treatment of transgenic plants Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amount of solvent that is indicated, and the amount of emulsifier indicated and the concentrate is diluted with water to the desired concentration. Soybean sprouts (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp., USA) are treated by immersion in the preparation of the active compound of the desired concentration and are infested with the tobacco budworm Heliothis virescens while the Leaves are still wet. After the desired period of time, dead insects are determined.
Example M; Increased activity by ammonia / phosphonium salts combined with penetrants Test in Myzus persicae Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent and emulsifier indicated, and the concentrate is diluted with water with emulsifier to the desired concentration. For the application with penetrants (methyl ester of rapeseed oil 500 EW), ammonium or salts of phosphonium or salts of ammonium and penetrants (methyl ester of rapeseed oil 500 EW), these are added in each case at a concentration of 1000 ppm to the spray liquid. Pepper plants (Capsicum annuum) which are heavily infested by the green peach aphid (Myzus persicae) are treated by spraying to the point of runoff with the preparation of active compound at the desired concentration. After the desired period of time, the effect is determined as a percentage 100% means that all animals have died; 0% means that none of the animals has died. In this test, for example, the following compounds of the Preparation Examples show good efficacy: see table.
Composite Table Dead Concentration (%) + SA + + SA + active (ppm) after 1000 EMAC EMAC 6 d ppm 1000 in each ppm case 1000 ppm
I-l-a-15 20 95 95 95 98 4 5 15 55 95
SA = ammonium sulfate Example N Test in Aphis gossypii Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the amounts of solvent and emulsifier as indicated, and the concentrate is diluted with water with emulsifier to the desired concentration. For the application with penetrants (rapeseed oil methyl ester 500 EW), ammonium or phosphonium salts or penetrating ammonium salts (methyl ester of rapeseed oil 500 EW), these are added in each case at a concentration of 1000 ppm to the spray liquid. Cotton plants are treated. { Gossypium hirsutum) that are very infested by the cotton aphid. { Aphis gossypii)
by spraying to the point of runoff with the preparation of active compound at the desired concentration. After the desired period of time, the effect is determined in percentage 100% means that all the aphids have died; 0% means that none of the aphids has died. In this test, for example, the following compounds of the Preparation Examples show good efficacy: see the Table Table Concentration Dead (%) + SA + + SA + active (ppm) after 1000 EMAC EMAC 6 d ppm 1000 in each ppm case 1000 ppm
I-l-a-7 20 55 65 75 99
SA = ammonium sulfate Example O Increased penetration into the plant by ammonium or phosphonium salts and synergistic increase in penetration into the plant by ammonium / phosphonium salts combined with penetrants. In this test, the penetration of the active compounds into enzyme-isolated cuticles was measured enzymatically from
apple leaves. Leaves, fully developed, cut from apple trees of the golden delicious variety were used. The cuticles were isolated - initially filling discs with stamped sheets and stained with dye on the underside by vacuum infiltration with a pectinase solution (0.2 to 2% hardness) buffered to a pH between 3 and 4, then azide was added Sodium and - letting discs of leaves treated in this way rest until the original structure of the leaves had dissolved and the acellular cuticles had separated. Then only the cuticles, without hairs or stromas, were used from the leaves. They were repeatedly washed by alternating between water and a buffer solution at pH 7. The clean cuticles obtained afterwards were mounted on Teflon plates and smoothed and dried with a gentle stream of air. In the following stage, the cuticle membranes obtained in this way were introduced in stainless steel diffusion cuvettes (= transport chambers) for transport studies through the membranes. To that end, the cuticles were inserted with tweezers in the center of the edges, covered with silicone grease, from the diffusion cuvettes and closed with a ring, which also
I had been treated with fat. The arrangement was chosen in such a way that the morphological exterior of the cuticles was oriented outwards, ie exposed to the air, while the original interior was oriented towards the interior of the diffusion cuvettes. The diffusion cuvettes were loaded with a 30% solution of ethylene glycol / water. To determine the penetration, in each case 10 μ? of the spray liquid of the composition later on to the outside of the cuticles. The spray liquid was prepared using local tap water of medium hardness. After the spray liquids had been applied, the water was allowed to evaporate and the chambers were inverted and placed in a thermostatically controlled apparatus in which the temperature and atmospheric moisture of the cuticles could be adjusted using a gentle stream of water. air on the cuticles with the spray coating (20 ° C, 60% rh). At regular intervals, an autosampler took aliquots and the content of active compound was determined by HPLC. The results of the test are shown in the following table. The numbers that are included are the average values of 8 to 10 measurements. It is clearly evident that, in addition to the EMAC, there is a synergistic effect.
Table 1 Active compound Penetration after 24 h /% a. i a. i. to . i. + a. i. + + SA EMAC RME (1 (1 g / D + g / D g / D SA (1 g / D Example I-l-a-21 2 1.1 35, 6 56, 9 200 ppm acetone / water
RME = rapeseed oil methyl ester (formulated at 500 EW, the concentration is expressed in g of the active compound (s)) SA = ammonium sulfate
It is noted that with respect to this date, the best method known to the applicant to carry out said invention is that which is clear from the present description of the invention.
Claims (23)
- CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. Compounds of the formula (I) characterized in that J represents optionally substituted cycloalkyl which may optionally be interrupted by heteroatoms, X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy, Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy, m represents a number 1, 2 or 3, with the proviso that at least one of the radicals J, X or Y is located at position 2 of the phenyl radical and is not hydrogen, CKE represents one of the groups wherein A represents hydrogen, in each case alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl optionally substituted by halogen, optionally substituted saturated or unsaturated cycloalkyl wherein optionally at least one ring atom is substituted with one heteroatom, or aryl, arylalkyl or hetaryl in each case optionally substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro. B represents hydrogen, alkyl or alkoxyalkyl, or A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cyclic residue which optionally contains at least one heteroatom, D represents hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring members are substituted by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or A and D together with the atoms to which they are attached represent a saturated or unsaturated cyclic moiety which is unsubstituted or substituted in the rest A, D and optionally contains at least one heteroatom (in the case of CKE = 8 an additional one), or A and Q1 together represent alkanediyl or alkenediyl which is optionally interrupted by a carbonyl group or heteroatoms , which are optionally substituted by halogen, hydroxyl; optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl and in which optionally two not directly adjacent carbon atoms form an additional optionally substituted cyclic moiety that can optionally be interrupted by heteroatoms or D and Q1 together with the atoms to those who are united represent a saturated or unsaturated cyclic moiety that optionally contains at least one heteroatom and is unsubstituted or substituted on the moiety D, Q1, Q1 represents hydrogen, alkyl, alkoxyalkyl, optionally substituted cycloalkyl (wherein optionally a methylene group is replaced by oxygen or sulfur) or optionally substituted phenyl, Q2 r Q Q5 and Q6 independently of one another represent hydrogen or alkyl, Q3 represents hydrogen, represents optionally substituted alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (wherein optionally a methylene group is replaced by oxygen or sulfur) or optionally substituted phenyl, or 'Q1 and Q2 together with the carbon atom to which they are attached represent an unsubstituted or substituted cyclic moiety that optionally contains a heteroatom, or Q3 and Q4 together with the carbon atom at which are together represent a saturated or unsaturated cyclic residue, insus substituted or substituted which optionally contains a heteroatom, G represents hydrogen (a) or represents one of the groups wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl in each case optionally substituted by halogen or cycloalkyl optionally substituted with halogen, alkyl or alkoxy which may be interrupted by at least one heteroatom, phenyloptionally substituted phenyl-alkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R 2 represents optionally substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl in each case optionally substituted by halogen or represents cycloalkyl, phenyl or benzyl in each case, R 3, R 4 and R 5 independently of each other represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio in each case optionally substituted with halogen or represents phenyl, optionally substituted benzyl, phenoxy or phenylthio in each case, R6 and R7 independently of one another represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl each optionally substituted by halogen, represent optionally substituted phenyl, represent benzyl optionally substituted, or together with the N atom to which they are attached represent a cyclic moiety which is optionally interrupted by oxygen or sulfur.
- 2. Compounds of the formula (I) according to claim 1, characterized in that J represents C3-C8 cycloalkyl optionally interrupted by oxygen and optionally substituted by halogen, Ci-C6 alkyl, Ci-C6 alkoxy, haloalkyl Ci-C6 or phenyl or C3-C6 cycloalkyl optionally substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, haloalkoxy C1-C4, X represents hydrogen, halogen, C1-C6 alkyl, C1-C4 haloalkyl , C 1 -C 6 alkoxy or C 1 -C 4 haloalkoxy, Y represents hydrogen, C 1 -C 4 haloalkyl, halogen, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy, m represents a number 1, 2 or 3, with the proviso that at least one of the radicals J, X or Y is located at position 2 of the phenyl radical and is not hydrogen, CKE represents the groups A represents hydrogen or C1-C12 alkyl, C3-C8 alkenyl, (C1-C10 alkoxy) -Ci-C alkyl, (C1-C10 alkylthio) -C1-C6 alkyl optionally substituted with halogen, cyclo- C3-C8 alkyl optionally substituted by halogen, C1-C6 alkyl or Ci-C6 alkoxy in which optionally one or two non-directly adjacent ring members are replaced by oxygen and / or sulfur or represents phenyl, naphthyl, hetaryl having 5 or 6 ring atoms, phenyl-C 1 -C 6 alkyl or naphthyl C 1 -C 6 alkyl each optionally substituted by halogen, C 1 -C 6 alkyl, Ci-C¾ haloalkyl, Ci-C¿ alkoxy haloalkoxy Ci-, cyano or nitro , B represents hydrogen, C1-C12 alkyl or (Ci-Ce alkoxy) -Ci-C6 alkyl or A, B and the carbon atom to which they are attached represent saturated C3-Ci0 cycloalkyl or unsaturated C5-C10 cycloalkyl, wherein optionally a ring member is replaced by oxygen or sulfur and which are optionally monosubstituted or disubstituted by C 1 -C 8 alkyl, C 3 -Cy cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkoxy , Ci-C8 alkylthio, halogen or phenyl or A, B and the carbon atom to which they are attached. esentan C3-C6 cycloalkyl which is substituted with an alkylenediyl group or by an alkylenedioxyl group or by an alkylenedithioyl group optionally containing one or two oxygen and / or sulfur atoms not directly adjacent and which is optionally substituted with C1-C4 alkyl, group which, together with the carbon atom to which it is attached, forms an additional ring of five to eight members, or A, B and the carbon atom to which they are attached represent C3-C8 cycloalkyl or Cs-Cg cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C2-Ce alkanediyl, C2-Ce alkenediyl or alkanediyenyl C4-C6 in each case optionally substituted with C1-C6 alkyl, Ci-C6 alkoxy or halogen in which optionally a methylene group is replaced by oxygen or sulfur, D represents hydrogen, C1-C12 alkyl, C3-C8 alkenyl, C3 alkynyl -C8, (C1-C10 alkoxy) C2-Cs alkyl in each case optionally substituted with halogen, C3-C8 cycloalkyl optionally substituted with halogen, C1-C4 alkyl, C1-C4 alkoxy or C1-C4 haloalkyl or, wherein optionally a ring member is substituted with oxygen or sulfur or phenyl, hetaryl having 5 or 6 ring atoms, phenyl-Ci-C6 alkyl or hetaryl-Ci-C6 alkyl having 5 or 6 ring atoms in each case optionally substituted with halogen, C1-C6 alkyl, haloalkyl or C1-C6, C1-C6 alkoxy, Ci-C6 haloalkoxy, cyano or nitro, or A and D together represent C3-C6 alkanediyl or alkeniyl C3-C6 in each case optionally substituted in which optionally a methylene group is replaced by a carbonyl, oxygen or sulfur group, the substituents being possible in each case: halogen, hydroxyl, mercapto or C1-C10alkyl, C1-6alkoxy C6, Ci-C6 alkylthio, C3-C7 cycloalkyl, phenyl or benzyloxy in each case optionally substituted with halogen, or a C3-C6 alkanediyl group, C3-C6 alkenediyl or an additional butadienyl group which are optionally substituted by C1-C6 alkyl or wherein optionally two adjacent substituents together with the carbon atoms to which they are attached form an additional saturated or unsaturated cyclic moiety having 5 or 6 ring atoms (in the case of the compound of the formula (1-1) A and D in this case together with the atoms to which they are attached represent, for example, the AD-1 to AD-10 groups mentioned below) which may contain oxygen or sulfur or which optionally contain one of the following groups or A and Q1 together represent C3-C6 alkanediyl or C4-C6 alkenediyl, each of which is optionally monosubstituted or disubstituted with identical or different substitutes from the group consisting of halogen, hydroxyl, C 1 -C 10 alkyl, alkoxy C 1 -C 6, C 1 -C 6 alkylthio, C 3 -C 7 cycloalkyl, each of which is optionally monosubstituted to trisustiutated with identical or different halogen substituents, and benzyloxy or phenyl, each of which is optionally monosubstituted trisust ituido with identical or different substituents from the group consisting of halogen, CI-C É alkyl and C 1 -C 6 alkoxy, which C3-C6 alkanediyl or C4-C6 alkenediyl optionally contain one of the following groups or has a bridge of a C 1 -C 2 alkanediyl group or a Oxygen atom or D and Q1 together represent C3-C6 alkanediyl which in each case is optionally monosubstituted or disubstituted with C1-C4 alkyl or C1-C4 alkoxy identical or different and is optionally interrupted by an oxygen atom or Q1 represents hydrogen, alkyl Ci-C6, (C 1-6 alkoxy) C 1 -C 2 alkyl 'C 3 -C 8 cycloalkyl optionally substituted with fluorine, chlorine, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl or C 1 -C 4 alkoxy in which optionally a methylene group is replaced by Oxygen or sulfur or phenyl optionally substituted by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, Ci-C 2 haloalkyl, Ci-C 2 haloalkoxy, cyano or nitro or Q 2, Q 4, Q 5 and Q 6 independently of one another represent hydrogen or C1-C4 alkyl, Q3 represents hydrogen, Ci-C6 alkyl, (Ci-C6 alkoxy) Ci-C2 alkyl, (Ci-C6 alkyl) thioalkyl Ci-C2, C3-C8 cycloalkyl optionally substituted with C1-C4 alkyl or C1 alkoxy -C4 in which optionally a methylene group is replaced by oxygen or sulfur or phenyl optionally substituted by halogen, C1-C4 alkyl, C1-C4 alkoxy, Ci-C2 haloalkyl, Ci-C2 haloalkoxy, cyano or nitro, Q1 and Q2 together with the carbon atom to which they are attached represent C3-C7 cycloalkyl optionally substituted with C1-C6 alkyl, Ci-C6 alkoxy or Ci-C2 haloalkyl in which optionally a ring member is replaced by oxygen or sulfur, or Q3 and Q4 together with the carbon atom to which they are attached represent a C3-C7 ring optionally substituted by C1-C4 alkyl, C1-C4 alkoxy or C1-C2 haloalkyl in which optionally a ring member is replaced by oxygen or sulfur, G represents hydrogen (a) or represents one of the groups (AND), wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 represents C1-C20 alkyl, C2-C2o alkenyl, (Ci-C8 alkoxy) Ci-C8 alkyl, (Ci-C8 alkylthio) Ci-C8 alkyl, (Ci-C8 polyalkoxy) Ci-C8 alkyl in each case optionally substituted with halogen or C3-C8 cycloalkyl optionally substituted with halogen, C1-C6 alkyl or C1-C6 alkoxy in which optionally one or more not directly adjacent ring members are replaced by oxygen and / or sulfur, represents phenyl optionally substituted by halogen, cyano, nitro, Ci-C6 alkyl, Ci-C6 alkoxy, Ci-C6 haloalkyl, Ci-C6 haloalkoxy, Ci-C6 alkylthio or (C1-C6 alkyl) sulfonyl, represents phenyl-C1-C6 alkyl optionally substituted by halogen, nitro, cyano, Ci-C6 alkyl, Ci-C6 alkoxy, Ci-C6 haloalkyl or Ci-C6 haloalkoxy, represents 5 or 6 membered heteroaryl optionally substituted with halogen or alkyl C1-C6, represents phenoxy-C1-C6 alkyl optionally substituted with halogen or Ci-C6 alkyl or represents 5- or 6-membered C 1 -C 6 hetaryloxyalkyl optionally substituted with halogen, amino or C 1 -C 6 alkyl, R 2 represents Ci-C 20 alkyl , C2-C20 alkenyl, (Ci-Cs alkoxy) C2-C8 alkyl, (Ci-Cg polyalkoxy) C2-Ce alkyl, optionally each substituted by halogen, represents C3-C8 cycloalkyl optionally substituted with halogen, C1-C6 alkyl or C1-C6 alkoxy or represents phenyl or benzyl in each case optionally substituted with halogen, cyano, nitro, C1-C6 alkyl, Ci-C6 alkoxy, Ci-C6 haloalkyl or Ci-C6 haloalkoxy, R3 represents optionally substituted Ci-C8 alkyl with halogen or represents phenyl or benzyl in each c optionally substituted with halogen, Ci-C6 alkyl, C1-C6 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano or nitro, R4 and R5 independently of each other they represent Ci-C8 alkyl, Ci-C8 alkoxy, Ci-C8 alkylamino, di- (Ci-C8 alkyl) amino, Ci-C8 alkylthio, C2-C8 alkenylthio, C3-C7 cycloalkylthio in each case optionally substituted with halogen or represent phenyl , phenoxy or phenylthio in each case optionally substituted with halogen, nitro, cyano, Ci-C4 alkoxy C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 6 and R 7 independently they represent hydrogen, represent Ci-C8 alkyl, C3-C8 cycloalkyl, Ci-C8 alkoxy, C3-C8 alkenyl, (Ci-C8 alkoxy) Ci-C8 alkyl optionally substituted with halogen, represent phenyl optionally substituted with halogen, Ci-C8 haloalkyl, Ci-C8 alkyl or Ci-C8 alkoxy, benzyl optionally substituted with halogen, C i ~ C8 alkyl, Ci-C8 haloalkyl or Ci-C8 alkoxy or together represent a C3-C6 alkylene radical optionally substituted with C1-C4 alkyl wherein optionally a carbon atom is substituted With oxygen or sulfur, R13 represents hydrogen, represents Ci-C8 alkyl or Ci-C8 alkoxy in each case optionally substituted with halogen, represents C3-C8 cycloalkyl optionally substituted with halogen, C1-C4 alkyl or C1-C4 alkoxy wherein optionally a methylene group is replaced by oxygen or sulfur, or represents phenyl, phenyl-C1-C4 alkyl or phenyl-C1-C4 alkoxy in each case optionally substituted with halogen, Ci-C6 alkyl, Ci-C6 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, nitro or cyano, R1 a represents hydrogen or Ci-Cs alkyl or R13 and R14a together represent C4-C6 alkanediyl, R15a and R16a are identical or different and represent Ci-C6 alkyl or R15a and R16a together represent a C2-C4 alkanediyl radical which is optionally substituted with Ci-C6 alkyl, Ci-C6 haloalkyl or by phenyl optionally substituted by halogen, Ci-C6 alkyl, haloalkyl C1 -C4, Ci-C6 alkoxy, C1-C4 haloalkoxy, nitro or cyano, R17a and R18a independently represent hydrogen, represent Ci-Cs alkyl optionally substituted with halogen or represent phenyl optionally substituted with halogen, Ci-C6 alkyl , C 1 -C 6 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, nitro or cyano or R 17a and R 18a together with the carbon atom to which they are attached represent a carbonyl group or represent C 5 -C 7 cycloalkyl optionally substituted with halogen, alkyl C1-C4 or al C1-C4 coxy in which optionally a methylene group is replaced by oxygen or sulfur, R19a and R20a independently of one another represent C1-C10 alkyl, C2-Ci0 alkenyl, C1-C10 alkoxy, C1-C10 alkylamino, C3 alkenylamino -C10, di- (Ci-Cio alkyl) amino or di- (C3-C10 alkenyl) amino.
- 3. Compounds of the formula (I) according to claim 1, characterized in that J represents C3-C6 cycloalkyl which is optionally interrupted by an oxygen atom and is optionally monosubstituted or disubstituted with fluorine, chlorine, C1-alkyl. -C4, C3-C6 cycloalkyl, Ci-C4 alkoxy or Ci-C2 haloalkyl, X represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C4 alkyl, trifluoromethyl, C1-C4 alkoxy, di f luoromet oxy or trifluoromethoxy, and represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, di f luoromet oxy or trifluoromethoxy, m represents a number 1 or 2 with the proviso that at least one of the radicals J, X or Y is located at position 2 of the phenyl radical and is not hydrogen, CKE represents one of the groups A represents hydrogen, represents Ci-C6 alkyl, Ci-C4 alkoxy, Ci-C2 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine or chlorine, represents C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with alkyl Ci-C2 or Ci-C2 alkoxy or (but not in the case of the compounds of the formulas (1-3), (1-4), (1-6) and (1-7)) represents phenyl or benzyl, each of which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, C1-C4 alkyl, Ci-C2 haloalkyl, C1-C4 alkoxy, Ci-C2 haloalkoxy, cyano or nitro, B represents hydrogen, C1-C4 alkyl or (Ci-C2 alkoxy) Ci-C2 alkyl or A, B and the carbon atom to which they are attached represent C5-cycloalkyl C7 saturated or unsaturated in which optionally a ring member is replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted with C1-C6 alkyl, trifluoromethyl, C1-C6 alkoxy or (C1-C3 alkoxy) C1-C3 alkoxy, with the condition that in this case Q3 represents hydrogen or methyl or A, B and the carbon atom to which they are attached represent C5-C6 cycloalkyl which is substituted with an alkylenediyl group or by an alkylenedioxyl group or by an alkylenedithiol group which optionally contains one or two atoms of oxygen or sulfur not directly adjacent and · which is optionally substituted with methyl or ethyl, a group that together with the carbon atom to which it is attached, forms an additional five or six member ring, with the proviso that Q3 in this case, it is particularly preferably hydrogen or methyl, or A, B and the carbon atom to which they are attached represent C3-C6 cycloalkyl or C5-C6 cycloalkenyl in which two substituents together with the carbon atoms to which they are attached they are in each case represented by C2-C4 alkanediyl, optionally substituted C2-C4 alkenediyl or butadye-diyl; with C1-C2 alkyl or C1-C2 alkoxy, with the proviso that Q3 in this case represents hydrogen or methyl, D represents hydrogen, represents Ci-C6 alkyl, C3-C6 alkenyl, (C1-C4 alkoxy) C2-C3 alkyl , each of which is optionally monosubstituted to tri-substituted with fluorine, represents 3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with C1-C4 alkyl, C1-C4 alkoxy or C1-C2 haloalkyl in which optionally a methylene group is replaced by oxygen or (but not in the case of the compounds of the formula (1-1)) represents phenyl or pyridyl, each of which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, C1-C4 alkyl, haloalkyl C1 -C4, C1-C4 alkoxy or C1-C4 haloalkoxy, or A and D together represent optionally monosubstituted or disubstituted C3-C5 alkanediyl in which a methylene group may be substituted with a carbonyl group (but not in the case of the the formula (1-1)), oxygen or sulfur , the possible substituents being C1-C2 alkyl or C1-C2 alkoxy, or A and D (in the case of the compounds of the formula (1-1)) together with the atoms to which they are attached represent one of the groups AD-1 to AD-10: AD-1 AD-2 AD-3 AD-4 AD-5 AD-6 AD-7 AD-8 AD-9 AD-10 or A and Q1 together represent C3-C4 alkanediyl which is in each case optionally monosubstituted or disubstituted with identical or different substituents which are selected from the group consisting of Ci-C2 alkyl and Ci-C2 alkoxy or D and Q1 together represent C3-C4 alkanediyl which is optionally interrupted by an oxygen atom, or Q1 represents hydrogen, C1-C4alkyl, (Ci-alkoxy) C4) Ci-C2 alkyl or C3-C6 cycloalkyl optionally substituted with methyl or methoxy in which optionally a methylene group is replaced by oxygen, Q2 represents hydrogen, methyl or ethyl, Q4, Q5 and Q6 independently of one another represent hydrogen or C1-C3 alkyl, Q3 represents hydrogen, C1-C4 alkyl, or C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with methyl or methoxy, Q1 and Q2 together with the carbon to which they are attached represent optionally substituted saturated C5-C6 cycloalkyl with C1-C4 alkyl or C1-C4 alkoxy wherein optionally one ring member is replaced by oxygen, or Q3 and Q4 together with the carbon to which they are attached represent a saturated C5-C6 ring optionally substituted with Ci-C2 alkyl or Ci-C2 alkoxy in which optionally a ring member is replaced by oxygen or sulfur, with the proviso that in this case A represents hydrogen or methyl, G represents hydrogen (a) or represents one of the groups (and), where E represents an equivalent of metal ion or an ammonium ion, L represents oxygen or sulfur M represents oxygen or sulfur, represents C1-C8, C2-C18 alkenyl, (C1-C4 alkoxy) Ci-C2 alkyl, (C1-C4 alkylthio) Ci-C2 alkyl, each of which is optionally monosubstituted trisubstituted with fluorine or chlorine, or C3-C6 cycloalkyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, C1-C2alkyl or C1-C2alkoxy and in which optionally one or two non-directly adjacent ring members are substituted by oxygen. represents phenyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, cyano, nitro, C1-C4 alkyl, C1-C4 alkoxy, C1-C2 haloalkyl or Ci-C2 haloalkoxy, R2 represents Ci-Cg alkyl, C2-C8 alkenyl or (Ci-C4 alkoxy) C2-C4 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, represents C3-C6 cycloalkyl which is optionally monosubstituted with Ci-C2 alkyl or Ci-C2 alkoxy or represents phenyl or benzyl , each of which is optionally monosubstituted or disust with fluoride, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 3 alkoxy, trifluoromethyl or trifluoromethoxy, R 3 represents C 1 -C 6 alkyl which is optionally monosubstituted to trisubstituted with fluorine or represents phenyl which is optionally monosubstituted with fluorine, chlorine, bromine, alkyl C1-C4, C1-C4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R4 represents alkyl i-, Ci-C6 alkoxy, Ci-Ce alkylamino, di- (Ci-C6 alkyl) amino, Ci-C6 alkylthio, alkenylthio C3-C4, C3-C6 cycloalkylthio or represents phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with fluorine, chlorine, bromine, nitro, cyano, C1-C3 alkoxy, Ci-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkyl or tri-fluoromethyl, R5 represents Ci-C6 alkoxy or alkylthio Ci ~ e, R6 represents hydrogen, Ci-C6 alkyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, C3-C6 alkenyl, (C 1 -C 6 alkoxy) C 1 -C 4 alkyl, represents phenyl which is optionally monosubstituted with fluorine, chlorine, bromine, trifluoromethyl or, C1-C alkyl or C1-C4 alkoxy, represents benzyl which is optionally monosubstituted with fluorine, chlorine, bromine, C1-C4 alkyl, trifluoromethyl or C1-C4 alkoxy, R7 represents Ci-C6 alkyl, C3-C6 alkenyl or ( Ci-C6 alkoxy) C 1 -C 4 alkyl, R 6 and R 7 together represent an alkylene radical C4-C5 which is optionally substituted with methyl or ethyl and wherein optionally a methylene group is replaced by oxygen or sulfur.
- 4. Compounds of the formula (I) according to claim 1, characterized in that J represents cyclopropyl 1, cyclopropyl 1, cyclobutyl, cyclopentone, cyclohexyl, oxetanyl, tetrahydrofurfuryl, tetrahydropyranyl. X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy, Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, m represents the number 1 or 2 , with the proviso that at least one of the radicals J, X or Y is located at the 2-position of the phenyl radical and is not hydrogen, where the radicals J, X and Y are arranged in the following phenyl substitution patterns (A) (B) (C) (D) (E) Y † H (F) Y † H (G) (H) Y † H (I) Y † H (J) Y † H (K) Y = H (L) Y = H where only in the substitution patterns of phenyl (B) and (L), X can also represent hydrogen, CKE represents one of the groups A represents hydrogen, represents C 1 -C 4 alkyl or (C 1 -C 2 alkoxy) C 1 -C 2 alkyl, each of which is optionally monosubstituted to trisubstituted with fluorine, represents cyclopropyl, cyclopentyl or cyclohexyl and, only in the case of the compounds of the formula (1-5) represents phenyl which is optionally monosubstituted or disubstituted with fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, B represents hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are attached represent saturated C5-C6 cycloalkyl in the that optionally a ring member is replaced by oxygen or sulfur and that it is optionally monosubstituted with methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy, methoxyethoxy, butoxy, methoxymethyl or ethoxyethoxy, with the proviso that in this case Q3 represents hydrogen, or A, B and the carbon atom to which they are attached represent C6 cycloalkyl which is optionally substituted with an alkylenedioxy group containing two oxygen atoms not directly adjacent, with the proviso that in this case Q3 represents hydrogen, or A, B and the carbon atom to which they are attached represent C5-C6 cycloalkyl or C5-C6 cycloalkenyl in which two substituents together with the carbon atoms to which they are attached n together represent C2-C4 alkanediyl or C2-C4 alkenediyl or butadyenediyl, with the proviso that in this case Q3 represents hydrogen, D represents hydrogen, represents Ci-C4 alkyl, C3-C4 alkenyl, (Cx-C alkoxy) C2 alkyl -C3, each of which is optionally monosubstituted to trisubstituted with fluorine, represents cyclopropyl, cyclopentyl or cyclohexyl or (but not in the case of the compounds of the formula (1-1)) represents phenyl or pyridyl, each of which is optionally monosubstituted with fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or trifluoromethyl, or A and D together represent C3-C5 alkanediyl which is optionally monosubstituted with methyl or methoxy and in which optionally a carbon atom is substituted with oxygen or sulfur or represents the AD group -1, A and Q1 together represent C3-C4 alkanediyl which is optionally monosubstituted or disubstituted with methyl or methoxy or D and Q1 together represent C3-C4 alkanediyl, Q1 represents hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclopentyl or cyclohexyl , Q2 represents hydrogen or methyl, Q4, Q5 and Q6 independently of one another represent hydrogen or methyl, Q3 represents hydrogen, methyl, ethyl or propyl, or Q1 and Q2 together with the carbon or to which they are attached represent saturated C5-C6 cycloalkyl which is optionally substituted by methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or butoxy and in which optionally a ring member is replaced by oxygen, or Q3 and Q4 together with the carbon to which they are attached represent a saturated C5-C6 ring which is optionally monosubstituted with methyl or methoxy, with the proviso that in this case A represents hydrogen, G represents hydrogen (a) or represents one of the groups -SO2-R3 (d) or E (f), in which L represents oxygen or sulfur, represents oxygen or sulfur and E represents an ammonium ion R1 represents Ci-C6 alkyl, C2-C17 alkenyl, (Ci-C2 alkoxy) -alkyl Cx, (Ci-C2 alkylthio) Ci alkyl, each of which is optionally monosubstituted with chlorine, or represents cyclopropyl or cyclohexyl, each of which is optionally monosubstituted with fluorine, chlorine, methyl or methoxy, represents phenyl which it is optionally monosubstituted with fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R2 represents Ci-C8 alkyl, C2-C6 alkenyl or (Ci-C4 alkoxy) C2-C3 alkyl, each of which it is optionally monosubstituted with fluorine, or represents phenyl or benzyl, R3 represents Ci-Cs-5 alkyl. Compounds of the formula (I) according to claim 1, characterized in that J represents cyclopropyl, X represents chloro, methyl or ethyl, Y represents chloro, methyl, ethyl or hydrogen, m represents the number 1 or 2, with the proviso that at least one of the radicals J, X or Y is located at the 2-position of the phenyl radical and is not hydrogen, where the radicals J, X and Y are arranged in the following patterns. phenyl substitution (E) Y † H (H) Y † H (K) Y = H (L) Y = H CKE represents one of the groups A represents C1-C4 alkyl or cyclopropyl, B represents hydrogen or methyl or A, B and the carbon atom to which they are attached represent saturated C5-C6 cycloalkyl in which optionally a ring member is replaced by oxygen and which is optionally monosubstituted with methoxy, ethoxy, butoxy or methoxymethyl, A, B and the carbon atom to which they are attached represent C6 cycloalkyl which is optionally substituted with a C2-C3 alkylenedioxy group having two non-directly adjacent oxygen atoms, D represents hydrogen or A and D together represent C3-C5 alkanediyl, A and Q1 together represent C3-C4 alkanediyl, Q2 represents hydrogen, G represents hydrogen (a) or represents one of the groups or S02-R3 (d) R1 represents Ci-C6 alkyl or represents phenyl which is monosubstituted with chlorine, R3 represents Ci-C8 alkyl R3 represents Ci-C8 alkyl 6. Process for preparing compounds of the formula (I) according to claim 1, characterized in that to obtain (A) compounds of the formula (I-1-a) wherein A, B, D, J, m, X and Y are as defined above, compounds of the formula (II) wherein A, B, D, J, m, X and Y are as defined above R represents alkyl (preferably Ci-Cg alkyl), they are condensed intramolecularly in the presence of a diluent and in the presence of a base, (B) compounds of the formula (α -2-a) wherein A, B, J, m, X and Y are as defined above, compounds of the formula (III) wherein A, B, J, m, X, Y and R8 are as defined above are condensed intramolecularly in the presence of a diluent and in the presence of a base, (C) compounds of the formula (? -3-a) ) ? -3-a: wherein A, B, J, m, X and Y are as defined above, compounds of the formula (IV) wherein A, B, J, m, X, Y and R8 are as defined above and V represents hydrogen, halogen, alkyl or alkoxy are cyclized intramolecularly, if appropriate in the presence of a diluent and if appropriate in the presence of an acid, (D) compounds of the formula (? -4-a) wherein A, D, J, m, X and Y are as defined above, compounds of the formula (V) D-C-CH2-A (V) wherein A and D are as defined above or their silylene ethers of the formula (Va) CHA D - C - OS (R8) 3 (Va) wherein A, D and R8 are as defined above are reacted with halides of ketonic acids of the formula (VI) wherein J, m, X and Y are as defined above and Hal represents halogen, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, (F) compounds of the formula (? -5-a) in which A, J, m, X and Y are as defined above compounds of the formula (VII) (VII) H2N-C-A wherein A is as defined above are reacted with compounds of the formula (VI) wherein Hal, J, m, X and Y are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, (F) compounds of the formula (? -6) -to) wherein A, B, Q1, Q2, J, m, X and Y are as defined above, compounds of the formula (VIII) wherein A, B, Q1, Q2, J, m, X and Y are as defined above and R8 represents alkyl are cyclized intramolecularly, if appropriate in the presence of a diluent and in the presence of a base, (G) compounds of the formula (? -7-a) wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above, compounds of the formula (IX) wherein A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above and R8 represents alkyl are condensed intramolecularly in the presence of a diluent and in the presence of a base, (I) compounds of the formula (? -8-a) wherein A, D, J, m, X and Y are as defined above, compounds of the formula (X) N (X) D H wherein A and D are as defined above a) are reacted with compounds of the formula (SAW) (SAW) wherein Hal, m, X, Y and J are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, or ß) are reacted with compounds of the formula (XI) wherein J, m, X and Y are as defined above and U represents NH2 or O-R8, where R8 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or?) are reacted with compounds of the formula (XII) wherein A, D, J, m, X, Y and R8 are as defined above, if appropriate in the presence of a diluent is appropriate in the presence of a base, (I) compounds of the formula (? -9-a) wherein A, B, D, J, m, Q1, Q2, X and Y are as defined above, compounds of the formula (XIII) wherein A, B, D, J, m, Q1, Q2, X and Y are as defined above R represents alkyl are condensed intramolecularly in the presence of a diluent and in the presence of a base, (J) compounds of the formula (I wherein A, B, J, m, Q1, Q2, X and Y are as defined above, and compounds of the formula (XIV) wherein A, B, J, m, Q1, Q2, X and Y are as defined above and R8 represents alkyl are condensed intramolecularly in the presence of a diluent and in the presence of a base, (K) compounds of the formulas (Ilb) to (? -10-b) shown above wherein A, B, D, J, m, Q1, Q2, Q3, Q4f Q5, Q6 R1, X and Y are as defined above, compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q2 , Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted (a) with acid halides of the formula (XV) wherein R1 is as defined above and Hal represents halogen or (ß) with carboxylic anhydrides of the formula (XVI) R ^ CO-O-CO-R1 (XVI) wherein R1 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger; (L) Compounds of the formulas (Ilc) to (? -10-c) shown above wherein A, B, D, J, m, Q1, Q2, Q3, Q4 / Q5 Q6, R2, M, X and Y are as defined above and L represents oxygen, compounds of the formulas (Ila) to (α-10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted with chloroform esters or chloroform thioesters of the formula (XVII) R2-M-C0-C1 (XVII) wherein R2 and M are as defined above, if was suitable in the presence of a diluent and if appropriate in the presence of an acid scavenger; () compounds of formulas (Ilc) to (? -10-c) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4 Q5 r Q6 r R2 ^ M, X and Y are as defined above and L represents sulfur, compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3 , Q4, Q5, Q6, X and Y are as defined above in each case are reacted with chloromonothioformic esters or chlorodithioformic esters of the formula (XVIII) (XVIII) wherein M and R2 are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger; and (N) compounds of the formulas (Ild) to (? -10-d) shown above wherein A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, R3 / X and Y are as defined above, compounds of the formulas (Ila) to (? -10-a) shown above in which A, B, D, J, m, Q1, Q2, Q3, Q4, Q5, Q6, X and Y are as defined above in each case are reacted with sulfonyl chlorides of the formula (XIX) R3 -S02-C1 (XIX) wherein R3 is as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger, (O) compounds of the formulas (Ile) a ( ? -10-e) shown above in which A, B, D, J, m, L, Q1, Q2, Q3, Q4, Q5, Q6 / 4 R5 / X and Y are as defined above, compounds of the formulas (Ila) to (? -10-a) shown above in which A , B, D, J, m, Q1, Q2, Q3, Q4, Q51 Q6 / X and Y are as defined above in each case are reacted with phosphorus compounds of the formula (XX) Hal - P (XX) LR where L, R 4 and R 5 are as defined above Hal represents halogen, if appropriate in the presence of a diluent and if appropriate in the presence of an acid scavenger, (P) the formulas (Ilf) to (? -10-f) shown above in which A, B, D, E, J, m, Q1, Q2, Q3, £ > Q5, Q6f X and Y are as defined above, composed of the formulas (Ila) a (? -10-a) wherein A, B, D, J, m, Q1, Q2, Q3, Q4, Q5 , Q6, X and Y are as defined above in each case they are reacted with metal compounds or amines of the formula (XXI) or (XXII) 10 RRN 'Me (OR10) t (XXI) (XXII) in which Me represents a divalent monovalent metal represents an ammonium ion 10 10 R N R11 / 2 t represents the number 1 or 2 and R10, R11, R12 independently of each other represent hydrogen or alkyl, if appropriate in the presence of a diluent, (Q) compounds of the formulas (Ilg) to (γ-10-g) shown above wherein A, B, D, J, m, L , Q1, Q2, Q3, Q4, Q5, Q6, R6, R7, X and Y are as defined above, composed of the formulas (Ila) to (? -10-a) shown above in which A , B, D, J, m, Q1, Q2, Q3, Q4 Q
- 5, Q6, X and Y are as defined above in each case (a) are reacted with isocyanates or isothiocyanates of the formula (XXIII) R6-N = C = L (XXIII) wherein R6 and L are as defined above, if appropriate in the presence of a diluent and if suitable in the presence of a catalyst, or (ß) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XXIV) L (XXIV) R7 'wherein L, R6 and R7 are as defined above, if was suitable in the presence of a diluent and if appropriate in the presence of an acid scavenger, (R) compounds of the formulas (Ila) to (? -10-g) shown above in which A, B, D, G, J, m, Q1, Q2, Q3, Q, Q5 / Q6 X and Y are as defined above, compounds of the formulas (? -1 ') to (I-lO'-g) wherein A, B, D, G, m, Q1, Q2, Q3, Q4, Q5 , Q
- 6, X and Y are as defined above and J 'preferably represents bromine or iodine they are coupled with cycloalkylboronic acid derivatives capable of coupling, for example with cycloalkylboronic acids of the formula (XXV) / OH J-ß (XXV) OH or their esters, in the presence of a solvent, in the presence of a catalyst and in the presence of one base.
- 7. Compositions characterized in that they comprise an effective amount of a combination of active compounds comprising, as components (a ') at least one substituted cyclic ketoenol of the formula (I) in which CKE, J, m, X and Y are such as defined above and (b ') at least one compound for improving the compatibility of crop plants from the following group of compounds: 4-dichloroacetyl-l-oxa-4-azaspiro [4, 5] decane (AD-67, MON-4660 ), l-dichloroacetylhexahydro-3, 3, 8a-trimethylpyrrolo [1,2- a] pyrimidin-6 (2H) -one (dicyclonon, BAS-145138), 4-Dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (benoxacor), 5-chloroquinolin-8-oxyacetate of 1-methylhexyl (cloquintocet-mexyl - see also related compounds in documents EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3- (2-chlorobenzyl) -1- (1-methyl-1-phenylethyl) urea (cumyluron), a- (cyanomethoximino) phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), (2,4-DB), 1- (1-methyl-1-phenylethyl) -3- (4-methylphenyl) urea of 4-acid (2,4-dichlorophenoxy) butyric acid (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), Sl-methyl-1-phenylethyl piperidin-1-thiocarboxylate (dimepiperate), 2,2-dichloro -N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2,2-dichloro-N, N-di-2-propenylacetamide (diclormid ), 6-dichloro-2-phenylpyrimidine (phenchlorim), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1, 2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl - see also the related compounds in EP-A-174562 and EP-A-346620), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N- (1,3-dioxolan oxime) -2-ylmethoxy) -a-trifluoroacetophenone (fluxofenim), 3-dichloro-acetyl-5- (2-furanyl) -2, 2-dimethyloxazolidine (furilazole, MON-13900), 4,5-dihydro-5, 5- ethyl diphenyl-3-isoxazolecarboxylate (is oxadifen-ethyl - see also the related compounds in WO-A-95/07897), 3,6-dichloro-2-methoxybenzoate of 1- (ethoxycarbonyl) ethyl (lactidiclor), (4-chloro-o-tolyloxy) acetic acid (MCPA), 2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate diethyl ester ( mefenpyr-diethyl - see also the related compounds in OA-91/07874), 2-dichloromethyl-2-methyl-l, 3-dioxolane (MG-191), 2-propenyl-1-oxa-azaspiro [4 , 5] decane-4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a- (1,3-dioxolan-2-ylmethoximino) phenylacetonitrile (oxabetrinyl), 2,2-dichloro-N- (l, 3-dioxolan-2-ylmethyl) -N- (2-propeni1) acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine ( R-29148), 4- (4-chloro-o-tolyl) butyric acid, 4- (4-chlorophenoxy) butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, 1- (2-chlorophenyl) -5- ethyl phenyl-lH-pyrazole-3-carboxylate, ethyl 1- (2, -dichlorophenyl) -5-methyl-lH-pyrazole-3-carboxylate, 1- (2,4-dichlorophenyl) -5-isopropyl-1H -pi ethyl 3-carboxylic acid-3-carboxylate, 1- (2, -dichloro-phenyl) -5- (1, 1-dimethylethyl) -lH-pyrazole-3-carboxylic acid ethyl ester, 1- (2,4-dichlorophenyl) -5 ethyl-phenyl-lH-pyrazole-3-carboxylate (see also the related compounds in EP-A-269806 and EP-A-333131), 5- (2,4-dichlorobenzyl) -2-isoxazolin-3- ethyl carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylate (see also compounds related in WO-A-91/08202), 1,3-chloroquinolin-8-oxyacetate 1,3-dimethylbut-1-yl, 5-chloroquinolin-8-oxyacetate 4-allyloxybutyl, 5-chloroquinolin-8-oxyacetate from 1-allyloxyprop-2-yl, methyl 5-chloroquinoxalin-8-oxyacetate, ethyl 5-chloroquinolin-8-oxyacetate, allyl 5-chloroquinoxalin-8-oxyacetate, 5-chloroquinolin-8-oxyacetate 2-oxoprop-1-yl, diethyl 5-chloroquinoline-8-oxylamonate, diallyl-5-chloroquinoxalin-8-oxylamonate, diethyl 5-chloroquinoline-8-oxylamonate (see also the related compounds in EP-A- 582198), 4-carboxy chroman-4-ylacetic acid (AC-304415, see EP-A-613618), 4-chlorophenoxyacetic acid, 3,3-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulfonylbenzene , l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (also known as N- (2-methoxybenzoyl) -4- [(methylaminocarbonyl) amino] benzenesulfonamide), 1- [4- ( ? -2-methoxybenzoylsulfamoyl) phenyl] -3,3-di-methylurea, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthylsulfamoyl) phenyl] 3, 3-dimethylurea, N- (2-methoxy-5-methylbenzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds, defined by the general formulas, of the general formula (lia) or of the formula (He) where m represents a number 0, 1, 2, 3, 4 or 5, A1 represents one of the divalent heterocyclic groups shown below n represents a number 0, 1, 2, 3, 4 or 5, A2 optionally represents alkanediyl substituted with C1-C4 alkyl and / or Ci-C4 alkoxycarbonyl and / or (Ci-C4 alkenyloxy) carbonyl having 1 or 2 carbon atoms. carbon, R14 represents hydroxyl, mercapto, amino, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino or di (C1-C4 alkyl) amino, R15 represents hydroxyl, mercapto, amino, Ci-C7 alkoxy, Ci-C6 alkenyloxy, (Ci-C6 alkenyloxy) Ci-C6 alkoxy, alkylthio Ci ~ C6, Ci-C6 alkylamino or di (C1-C4 alkyl) amino, R16 represents C1-C4 alkyl in each case optionally substituted with fluorine, chlorine and / or bromine, R17 represents hydrogen, Ci-C6 alkyl, C2 alkenyl C6 or C2-C6 alkynyl, (C1-C4 alkoxy) C1-C4 alkyl, dioxolanylalkyl C1-C4, furyl, furyl C1-C4 alkyl, thienyl, thiazolyl, piperidinyl each optionally substituted with fluorine, chlorine and / or bromine, or phenyl optionally substituted with fluorine, chlorine and / or bromine or C1-C4 alkyl, R18 represents hydrogen, Ci-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, (C1-C4 alkoxy) C1-C4 alkyl, dioxolanylalkyl C1- C4, furyl, C 1 -C 4 -alkylalkyl, thienyl, thiazolyl, piperidinyl each optionally substituted by fluorine, chlorine and / or bromine, or phenyl optionally substituted by fluorine, chlorine and / or bromine or C1-C4 alkyl, R17 and R18 also together represent C3-C6 alkanediyl or C2-C5 oxaalkanediyl, each of which is optionally substituted by C1-C4 alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, they form a 5 or 6 membered carbocycle, R19 represents hydrogen, cyano, halogen, or represents C1-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, R20 represents hydrogen, Ci-C6 alkyl, C3-C6 cycloalkyl or tri- (C1-C4 alkyloxy) optionally substituted with hydroxyl, cyano, halogen or C1-C4 alkoxy, R21 represents hydrogen, cyano, halogen, or represents C1-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, X1 represents nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, alkoxy C1-C4 or C1-C4 haloalkoxy, X2 represents hydrogen, cyano, nitro, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, X3 represents hydrogen, cyano, nitro, halogen, alkyl C1-C4, haloalkyl C1-C4, alkoxy C1-C4 or haloalkoxy C1-C4, and / or the following compounds, defined by the general formulas, of the general formula (lid) or of the general formula (lie) (He) where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R22 represents hydrogen or C1-C4 alkyl, R23 represents hydrogen or C1-C4 alkyl , R24 represents hydrogen, Ci-C6 alkyl, C1-C6 alkoxy, Ci-C6 alkylthio, Ci-C6 alkylamino or di (Ci-C4 alkyl) amino in each case optionally substituted with cyano, halogen or C1-C4 alkoxy, or cycloalkyl C3-C6, C3-C6 cycloalkyloxy, C3-C6 cycloalkylthio or C3-C6 cycloalkylamino in each case optionally substituted with cyano, halogen or C1-C4 alkyl, R25 represents hydrogen, Ci-C6 alkyl optionally substituted with cyano, hydroxyl, halogen or C1-C4 alkoxy, C3-C6 alkenyl or C3-C6 alkynyl in each case optionally substituted with cyano or halogen, or C3-C6 cycloalkyl optionally substituted with cyano, halogen or C1-C4 alkyl, or C3-C6 cycloalkyl substituted with C1-6 alkyl C4, or phenyl optionally substituted with nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, or together with R represents C2-C6 alkanoidyl or C2-C5 oxalkanoidyl in each case optionally substituted with C1-C4 alkyl, X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C1-C4 alkyl, haloalkyl C1 -C4, C1-C4 alkoxy or C1-C4 haloalkoxy, and X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or haloalkoxy C1-C4.
- Composition according to claim 7, characterized in that the compound for improving the compatibility of crop plants is selected from the following group of compounds: cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron or the compounds Y
- 9. Composition according to one of claims 7 and 8, characterized in that the compound for improving the compatibility of crop plants is cloquintocet-mexyl.
- Composition according to one of claims 7 and 8, characterized in that the compound for improving the compatibility of crop plants is mefenpyr-diethyl.
- 11. Compositions for controlling pests and / or unwanted vegetation, characterized in that they comprise at least one compound of the formula (I) according to claim 1.
- 12. Process for controlling animal pests and / or unwanted vegetation, characterized in that the compounds of the formula (I) according to claim 1 are allowed to act on the pests, unwanted vegetation and / or their habitat.
- 13. Use of compounds of the formula (I) according to claim 1 for controlling animal pests and / or unwanted vegetation.
- 14. Process for preparing compositions for controlling pests and / or unwanted vegetation, characterized in that the compounds of the formula (I) according to claim 1 are mixed with fillers and / or surfactants.
- 15. Use of compounds of the formula (I) according to claim 1 for preparing compositions for control pests and / or unwanted vegetation.
- 16. Procedure for controlling unwanted vegetation, characterized in that a composition according to claim 7 is allowed to act on the plants or their habitat.
- 17. Use of a composition according to claim 7 for controlling unwanted vegetation.
- 18. Process for controlling unwanted vegetation, characterized in that a compound of the formula (I) according to claim 1 and the compound for improving the compatibility of crop plants according to claim 7 are allowed to act, separately and in a temporary succession, on the plants or their habitat.
- 19. Compounds of the formula (II) characterized in that A, B, D, J, m, X and Y are as defined above and R8 represents alkyl.
- 20. Compounds of the formula (III characterized in that A, B, J, m, X and Y and R8 are as defined above.
- 21. Compounds of the formula (IV) characterized in that A, B, J, m, X, Y and R8 are as defined above and V represents hydrogen, halogen, alkyl or alkoxy.
- 22. Compounds of the formula (VI) characterized because J, m, X and Y are as defined above and Hal represents halogen.
- 23. Compounds of the formula (VIII) characterized in that A, B, Q1, Q2, R8, J, m, X and Y are as defined above. characterized in that A, B, J, m, Q3, Q4, Q5, Q6, X, Y and R8 are as defined above. 25. Compounds of the formula (XII) characterized in that A, D, J, m, X, Y and R8 are as defined above. Compounds of the formula (XIII) characterized in that A, B, D, J, m, Q1, Q2, X, Y and R8 are as defined above. 27. Compounds of the formula (XIV) characterized in that A, B, J, m, Q1, Q2, X, Y and R8 are as defined above. 28. Compounds of the formula (XXVIII) (XXVIII) characterized in that A, B, D, J, m, X, and Y are as defined above. 29. Compounds of the formula (XXVII) (XXVII) characterized in that J, m, X, Y and Z are as defined above 30. Compounds of the formula (XXXII) (XXXII) characterized in that A, B, D, J, m, X and Y are as defined above. 31. Compounds of the formula (XXXIV) (XXXIV) characterized in that J, m, X, Y and R8 are as defined above. Compounds of the formula (XXXVI) (XXXVI) characterized in that J, m, X, and Y are as defined above 33. Compounds of the formula (XI) characterized in that J, m, X, and Y are as defined above, U represents OR8 and R8 is as defined above. 34. Compounds of the formula (XXXVII) (XXXVII) characterized in that J, m, X, Y, A, B, Q1 and Q2 are as defined above. 35. Compounds of the formula (XXXVIII) (XXXVIII) characterized in that A, B, J, m, Q1, Q2, X, Y, R8 and R8 'are as defined above. 36. Compounds of the formula (XLI) characterized in that A, B, J, m, Q3, Q4, Q5, Q6, X and Y are as defined above. 37. Compounds of the formula (XLII) characterized in that A, B, J, m, Q3, Q4, Q5, Q6, X, Y, R8 and R8 'are as defined above. 38. Compounds of the formula (LXVI) characterized in that A, B, J, m, D, Q1, Q2, X and Y are as defined above. 39. Compounds of the formula (XI) characterized in that J, m, X, Y and U are as defined above 40. Compounds of the formula (XXX) characterized in that J, X, Y and m are as defined above. 41. Composition, characterized in that it comprises at least one compound of the formula (I) according to claim 1 or a composition according to claim 7 and at least one salt of the formula (III ') wherein D represents nitrogen or phosphorus, R26, R27, R28 and R29 independently from each other represent hydrogen or optionally substituted Ci-Cg alkyl or optionally substituted monounsaturated or polyunsaturated Ci-Cg alkylene, wherein the substituents may selected from the group consisting of halogen, nitro and cyano, n represents 1, 2, 3 or 4, R30 represents an inorganic or organic anion. 42. Composition according to claim 41, characterized in that it comprises at least one penetrant. 43. Process for improving the activity of pesticides and / or herbicides comprising an active compound of the formula (I) according to claim 1 or a composition according to claim 7, characterized in that the ready-to-use composition (liquid in spray) is prepared using a salt of the formula (III ') according to claim 42. 44. Process according to the claim 43, characterized in that the spray liquid is prepared using a penetrant.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE102006007882.9 | 2006-02-21 |
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MX2008010702A true MX2008010702A (en) | 2008-10-03 |
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