MX2008008733A - 2,4,6-trialkylphenyl substituted cyclopentane-1,3-dione - Google Patents
2,4,6-trialkylphenyl substituted cyclopentane-1,3-dioneInfo
- Publication number
- MX2008008733A MX2008008733A MXMX/A/2008/008733A MX2008008733A MX2008008733A MX 2008008733 A MX2008008733 A MX 2008008733A MX 2008008733 A MX2008008733 A MX 2008008733A MX 2008008733 A MX2008008733 A MX 2008008733A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- represent
- optionally
- Prior art date
Links
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical class O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 230000002363 herbicidal Effects 0.000 claims abstract description 41
- 239000004009 herbicide Substances 0.000 claims abstract description 23
- 239000000575 pesticide Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 234
- -1 C-alkoxy -C6 Chemical group 0.000 claims description 207
- 125000003545 alkoxy group Chemical group 0.000 claims description 151
- 229910052739 hydrogen Inorganic materials 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 121
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 105
- 150000002367 halogens Chemical class 0.000 claims description 105
- 239000000460 chlorine Substances 0.000 claims description 102
- 229910052801 chlorine Inorganic materials 0.000 claims description 102
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 90
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 80
- 239000011737 fluorine Substances 0.000 claims description 80
- 229910052731 fluorine Inorganic materials 0.000 claims description 80
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 78
- 150000002431 hydrogen Chemical group 0.000 claims description 77
- 125000001153 fluoro group Chemical group F* 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 229910052799 carbon Inorganic materials 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 63
- 239000001301 oxygen Substances 0.000 claims description 63
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 63
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 59
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 52
- 239000011593 sulfur Substances 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 52
- 239000004480 active ingredient Substances 0.000 claims description 51
- 239000003085 diluting agent Substances 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 239000000956 alloy Substances 0.000 claims description 14
- 229910045601 alloy Inorganic materials 0.000 claims description 14
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical class [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 claims description 14
- 244000045947 parasites Species 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- AOGYCOYQMAVAFD-UHFFFAOYSA-N Chloroformic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000005842 heteroatoms Chemical group 0.000 claims description 11
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 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 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- ICJSJAJWTWPSBD-UHFFFAOYSA-N 2-(5-chloroquinolin-8-yl)oxyacetic acid Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 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
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000004434 sulfur atoms Chemical group 0.000 claims description 6
- 150000007970 thio esters Chemical class 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000002794 2,4-DB Substances 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 5
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims description 5
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 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
- 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 4
- 239000005631 2,4-D Substances 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004429 atoms Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic S-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 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
- JCHMGYRXQDASJE-UHFFFAOYSA-N 2-methoxy-N-[4-(methylcarbamoylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 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 3
- 239000005504 Dicamba Substances 0.000 claims description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N Mecoprop Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical compound SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 3
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl 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
- 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
- AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- JNFSCNHXRUOQJS-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC(Cl)=CC=C1C JNFSCNHXRUOQJS-UHFFFAOYSA-N 0.000 claims description 2
- HCEJOAJCHSLTDV-UHFFFAOYSA-N 2-(8-chloroquinoxalin-5-yl)oxyacetic acid Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=N1 HCEJOAJCHSLTDV-UHFFFAOYSA-N 0.000 claims description 2
- PMBFXWQQWHFBQV-UHFFFAOYSA-N 2-(8-chloroquinoxalin-5-yl)oxypropanedioic acid Chemical compound C1=CN=C2C(OC(C(=O)O)C(O)=O)=CC=C(Cl)C2=N1 PMBFXWQQWHFBQV-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
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 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
- BEWNYGSVADPYKQ-UHFFFAOYSA-M C(C)OC(=O)C(C)C1=C(C(=C(C(=O)[O-])C(=C1)Cl)OC)Cl Chemical compound C(C)OC(=O)C(C)C1=C(C(=C(C(=O)[O-])C(=C1)Cl)OC)Cl BEWNYGSVADPYKQ-UHFFFAOYSA-M 0.000 claims description 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 2
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 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
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims description 2
- NYDKNJDNBUFWRJ-UHFFFAOYSA-N N-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)N(C)C)C=C1 NYDKNJDNBUFWRJ-UHFFFAOYSA-N 0.000 claims description 2
- OMKXSWYZPVQWRO-UHFFFAOYSA-M O1C(C=CC)CN(C([S-])=S)C11CCCCC1 Chemical compound O1C(C=CC)CN(C([S-])=S)C11CCCCC1 OMKXSWYZPVQWRO-UHFFFAOYSA-M 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 2
- 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 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- LPVVTHQFIVXMEZ-UHFFFAOYSA-N diethyl 2-(5-chloroquinolin-8-yl)oxypropanedioate Chemical compound C1=CN=C2C(OC(C(=O)OCC)C(=O)OCC)=CC=C(Cl)C2=C1 LPVVTHQFIVXMEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- VZZVOKHLRXJIEP-UHFFFAOYSA-N ethyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OCC)C1=CC=CC=C1 VZZVOKHLRXJIEP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- LQPRNRFJJUSONA-UHFFFAOYSA-N methyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OC)C1=CC=CC=C1 LQPRNRFJJUSONA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 2
- DVFGVGYKHMQZJC-UHFFFAOYSA-N pent-4-enamide Chemical compound NC(=O)CCC=C DVFGVGYKHMQZJC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- HFGGXBQZQRVOKM-UHFFFAOYSA-N piperidine-1-carbothioic S-acid Chemical compound SC(=O)N1CCCCC1 HFGGXBQZQRVOKM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 244000038559 crop plants Species 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
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- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
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- 238000000053 physical method Methods 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 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
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
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- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-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
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- 210000001519 tissues Anatomy 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
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-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
- 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
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-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
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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 2,4,6-trialkylphenyl substituted cyclopentane-1,3-dione of formula (I), in which X, Y, A, B, Q1, Q2and G are defined as cited in the claims, to several methods and intermediate products for their production and to their use as pesticides and/or herbicides, in addition to selective herbicidal agents containing 2,4,6 trialkylphenyl substituted cyclopentane-1,3-diones of formula (I) and at least one compound that improves their compatibility with cultivated plants.
Description
CICLOPENTAN-1, 3-DIONAS REPLACED WITH 2, 4, 6-TRIALQUILFENILO
DESCRIPTION OF THE INVENTION The present invention relates to new cyclopentan-1,3-diones substituted with 2,4,6-trialkylphenyl, to various processes for their preparation and to their use as pesticides and / or herbicides. The invention also relates to new combinations of selective herbicidal active ingredients containing, on the one hand, cyclopentan-1,3-dione derivatives substituted with 2,4,6-trialkylphenyl and, on the other hand, at least one compound that improves tolerance in crop plants and that can be used with particularly good success for the selective control of weeds in different crops of useful plants. It is known that certain substituted 2-arylcyclopentandiones possess herbicidal, insecticidal and acaricidal properties (cf., for example, US-4 283 348;
338 122; 4,466,666; 4 526 723; 4 551 547; 4,632,698; WO 96/01798; WO 96/03366, WO 97/14667, as well as WO 98/39281, WO
99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770,
WO 03/062244, WO 04/080962, DE-A-10326386. In addition, similarly substituted compounds are known: 3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-en-1-one from the publication by Micklefield et. al, Tetrahedron, (1992), 7519-26, as well as REF. : 194182
natural substance Involution (-) - cis-5- (3,4-dihydroxyphenyl) -3,4-dihydroxy-2- (4-hydroxyphenyl) -cyclopent-2-en-one from Edwards et al., J Chem. Soc. S, (1967), 405-9. An insecticidal or acaricidal action is not described. In addition, 2- (2,4-, 6-trimethylphenyl) -1,3-indandione is known from the publication J. Economic Entomology, 66 (1973); 584 and publication for patent application information DE-A 2 361 084, with indication of herbicidal and acaricidal actions. The efficacy and amplitude of action of these compounds is not, however, always completely satisfactory with application rates and low concentrations. In addition, the tolerance of plants to these compounds is not always sufficient. Now, new compounds of the formula (I) have been found
wherein X represents methyl and Y represents methyl or ethyl, or X and Y represent ethyl, wherein A represents hydrogen, alkyl, alkenyl, alkoxyalkyl,
optionally substituted alkylthioalkyl in each case with halogen, optionally substituted, saturated or unsaturated cycloalkyl, in which optionally at least one ring atom is replaced by a heteroatom, B represents hydrogen, alkyl or alkoxyalkyl, or A and B represent, together with the carbon atom to which they are attached, a saturated or unsaturated unsubstituted or substituted ring, optionally containing at least one heteroatom, A and Q1 represent together optionally substituted alkandiyl or alkenediyl, which may optionally be interrupted by a heteroatom, Q1 and Q2 represent , independently of one another, hydrogen or alkyl, or in which X represents ethyl and Y represents methyl, wherein A and B, together with the carbon atom to which they are attached, represent an unsubstituted or substituted 4-to-4-membered ring 8 saturated or unsaturated members, and Q1 and Q2 represent hydrogen or
- -
A and Q1 together represent alloy C2-C6"diyl or alken C2-C6-diyl in each case optionally substituted, which may optionally be interrupted by heteroatoms and B and Q2 represent, independently of each other, hydrogen or alkyl, G represents hydrogen (a) or one of the groups
(H.H),
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 with halogen or cycloalkyl optionally substituted with halogen, alkyl or alkoxy, which may be interrupted by at least one heteroatom, phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl in each case optionally substituted, R 2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl in each case optionally substituted
with halogen or cycloalkyl, phenyl or benzyl in each case optionally substituted, R3, R4 and R5 represent, independently of each other, alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio optionally substituted in each case with halogen or phenyl, benzyl, phenoxy or phenylthio in each case optionally substituted, R6 and R7 represent, independently of each other, hydrogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl optionally substituted in each case with halogen, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, they represent a cycle eventually interrupted by oxygen or sulfur. The compounds of the formula (I) can be present, also depending on the type of substituents, as isomers or mixtures of geometric and / or optical isomers, in different composition, which can optionally be separated in a conventional manner. Both the pure isomers and the isomeric mixtures, their preparation and use, as well as the agents containing them, are the object of the present invention. In the following, for purposes of simplification, compounds of the formula (I) are always mentioned, although mention is made both of the pure compounds and optionally also of the mixtures with different proportions of isomeric compounds.
The compounds of the formula (I) can be present as a function of the position of the substituents G in the two isomeric forms of the formulas (I-A) and (I-B)
(I-A) (I-B)
which is expressed by means of the dotted line in the formula
(I) - The compounds of the formulas (I-A) and (1-B) can be present both as mixtures as well as in the form of their pure isomers. Mixtures of compounds of formulas
(I-A) and (I-B) can optionally be separated by physical methods, for example, by chromatographic methods. For reasons of better visualization, only one of the possible isomers is explained below. This does not exclude the fact that the compounds may optionally be in the form of the isomeric mixtures or in another isomeric form. Including the different meanings (a), (b), (c), (d),
(e), (f) and (g) of group G, the following main structures (I-a) to (I-g) result:
- - (I-a): < M > ):
(I- (I-O:
«G > :
EU
- -
A, B, Q1, Q2, E, L, M, X, Y, R1, R2, R3, R, R5, R6 and R7 have the meanings indicated above. In addition, it was found that the novel compounds of the formula (I) are obtained according to one of the methods described below: (A) Compounds of the formula (I-a) are obtained
wherein A, B, Q1, Q2, X and Y have the meanings indicated above, when ketocarboxylic acid esters of the formula (II) are intramolecularly cyclized
wherein A, B, Q1, Q2, X and Y have the meanings indicated above, and R8 represents alkyl (especially Ci-Cs alkyl), optionally in the presence of a diluent and in
presence of a base. In addition, it was found that the compounds of the formula (Ib) mentioned above are obtained, in which A, B, Q1, Q2, R1, X and Y have the meanings indicated above, if compounds of the formula (Ia) are reacted ) indicated above, in which A, B, Q1, Q2, X and Y have the meanings indicated above, (a) with acid halides of the formula (III)
wherein R1 has the meaning indicated above and Hal represents halogen (especially chlorine or bromine) or (ß) with carboxylic acid anhydrides of the formula (IV)
RJ-CO-O-CO-R1 (TV)
wherein R1 has the meaning indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor; (C) the compounds of the formula (ic) mentioned above are obtained, in which A, B, Q1, Q2, R2, M, X and Y have the meanings indicated above and L represents oxygen, if compounds of the formula (Ia) indicated above, in which A, B, Q1, Q2, X and Y have the meanings indicated above, in each case with esters of chloroformic acid or thioesters of acid
- - chloroform of the formula (V)
R2- -C0-C1 (V) in which R2 and M have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor; (D) the compounds of the formula (Ic) mentioned above are obtained, in which A, B, Q1, Q2, R2, M, X and Y have the meanings indicated above and L represents sulfur, if the compounds of the formula (Ia), in which A, B, D, Q1, Q2, X and Y have the meanings indicated above, in each case with esters of chloromonothioformic acid or esters of chlorodithioformic acid of the formula (VI)
wherein M and R2 have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor and (E) there are obtained compounds of the formula (1-d) indicated above, in which A, B, Q1, Q2, R3, X and Y have the meanings indicated above, if compounds of the formula (Ia) indicated above are reacted, in which A, B, D, Q1, Q2, X and Y have the
- - meanings indicated above, in each case with sulphonic acid chlorides of the formula (VII
R3-S? 2-Cl (VII)
wherein R3 has the meaning indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor, (F) compounds of the formula (Ie) indicated above are obtained, in which A, B, L, Q1, Q2, R4, R5, X and Y have the meanings indicated above, if compounds of the formula (Ia) indicated above are reacted, in which A, B, Q1, Q2, X and Y have the meanings indicated above , in each case with phosphorus compounds of the formula (VIII)
R4 Hal- P (HIV) L R
wherein L, R 4 and R 5 have the meanings indicated above and Hal represents halogen (especially chlorine or bromine), optionally in the presence of a diluent and optionally in the presence of an acid acceptor, (G) compounds of the formula are obtained (If) mentioned above, in which A, B, E, Q1, Q2, X and Y have the
- - meanings indicated above, if compounds of the formula (la) are reacted, in which A, B, Q1, Q2, x and Y have the meanings indicated above, in each case with metal compounds or amines of the formulas (IX ) or (X)
R10 R11 Me (ORl °), (DQ 12 (X)
wherein Me represents a mono- or divalent metal (preferably an alkaline or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium), t represents the number 1 or 2 and R10, R11, R12 represent, independently from each other, hydrogen or alkyl (preferably Ci-Cs alkyl), optionally in the presence of a diluent, (H) there are obtained compounds of the formula (Ig) indicated above, wherein A, B, L, Q1, Q2 , R6, R7, x and Y have the meanings indicated above, if compounds of the formula (Ia) indicated above are reacted, in which A, B, Q1, Q2, X and Y have the meanings indicated above, in each case () with isocyanates or isothiocyanates of the formula (XI)
R6.N = C = L i)
in which R6 and L have the meanings indicated above, possibly in the presence of a diluent and optionally in
- - presence of a catalyst or (ß) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XII)
wherein L, R6 and R7 have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor. On the other hand, it was found that the new compounds of the formula (I) have a very good as pesticides, preferably as insecticides, acaricides and herbicides. Surprisingly, it was now found that certain substituted cyclic ketoenols prevent very well, with a joint application with the compounds (crop protectors / antidotes) that improve the tolerance in crop plants described below, the damage of crop plants and can be employ, in a particularly advantageous manner, as combined preparations of broad action for the selective control of unwanted plants in crops of useful plants such as, for example, in cereals, but also in corn, soybeans and rice. Also the subject of the invention are selective herbicidal agents having an active content of a combination
- - of active ingredients comprising as components a ') at least one compound of the formula (I), in which A, B, G, Q1, Q2, X and Y have the meanings indicated above and (b') at least one compound that improves the tolerance of the crop plants of the following group of compounds: 4-dichloroacetyl-l-oxa-4-aza-spiro [4, 5] -decane (AD-67, MON4660), l-dichloroacetyl -hexahydro-3, 3, 8a-trimethylpyrrolo [1,2-a] -pyrimidin-6 (2H) -one (dicyclonone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H- l, 4-benzoxazine (benoxacor), 5-chloro-quinoline-8-oxy-acetic acid (1-methylhexyl ester)
(cloquintocet-mexyl - also other related compounds compiled in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3- (2-chloro-benzyl) -l - (l-methyl-l-phenyl-ethyl) -urea (cumylurone), a- (cyanomethoximino) -phenylacetonitrile
(cyometrinyl), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4- (2,4-dichloro-phenoxy) -butyric acid (2,4-DB), 1- (1-methyl-1-methyl) phenyl-ethyl) -3- (4-methylphenyl) -urea (daimurone, dimrona), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl ester of the piperidin-1-thiocarboxylic acid (dimepiperate), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2 , 2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), 4,6-dichloro-2-phenyl-pyrimidine (phenchlorim), 1- (2,4-dichloro-phenyl) ethyl ester -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid (fenclorazol-ethyl-comp.
- - also related compounds in EP-A-174562 and EP-A-346620), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid methyl ester (flurazole), 4-chloro-N- (1 , 3-dioxolan-2-yl-methoxy) -a-trifluoro-acetophenoxy (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2, 2-dimethyl-oxazolidine (furilazole, MON-13900), 4, Ethyl 5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl-comp. Also related compounds in WO-A 95/07897), 1- (ethoxycarbonyl) -ethyl-3,6-dichloro- 2-methoxybenzoate (lactidychlor), (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-diethyl dicarboxylate (mefenpyr-diethyl-comp. Also related compounds in WO-A-91/07874), 2-dichloromethyl-2- methyl-l, 3-dioxolane (MG-191), 2-propenyl-l-oxa-4-azaspiro [4, 5] decan-4-carbodithioate (MG-838), 1,8-naphthalene anhydride, or - (1, 3-dioxolan- 2-yl-methoximino) -phenylacetonitrile (oxabetrinyl), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N (2-propenyl) -acetamide (PPG-1292), 3- dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4- (4-chloro-o-tolyl) -butyric acid, acid 4- (4-chloro-phenoxy) butyric acid, diphenylmethoxyacetic acid, diphenylmethoxyacetic acid methyl ester, diphenylmethoxyacetic acid ethyl ester, 1- (2-chloro-phenyl) -5-phenyl-1H-pyrazole- methyl ester 3-carboxylic acid ethyl ester of l- (2,4-
- - dichloro-phenyl) -5-methyl-1H-pyrazole-3-carboxylic acid 1- (2, -dichloro-phenyl) -5-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester, ethyl ester 1- (2,4-dichloro-phenyl) -5- (1,1-dimethyl-ethyl) -lH-pyrazole-3-carboxylic acid, l- (2,4-dichloro-phenyl) -5-phenyl- ethyl ester 1H-pyrazole-3-carboxylic acid (also including related compounds in EP-A-269806 and EP-A-333131), 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester , 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester, 5- (4-fluoro-phenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (also including related compounds in the WO-A-91/08202), 5-chloro-quinoline-8-oxy-acetic acid (1, 3-dimethyl-but-l-yl) -ester, 5-chloro-butyl 4-allyloxy-5-chloro ester -quinolin-8-oxy-acetic acid, l-allyloxy-prop-2-yl ester of 5-chloro-quinoline-8-oxy-acetic acid, 5-chloro-quinoxalin-8-oxy-acetic acid methyl ester, ester etli 5-chloro-quinoline-8-oxy-acetic acid co, 5-chloro-quinoxalin-8-oxy-acetic acid allyl ester, 5-chloro-quinoline-8-oxy-acetic acid 2-oxo-propyl ester, 5-chloro-quinoline-8-diethyl ester -oxi-malonic acid, 5-chloro-quinoxalin-8-oxy-malonic acid diallyl ester, 5-chloro-quinoline-8-oxy-malonic acid diethyl ester (cf. also related compounds in EP-A-582198) ), 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. EP-A-613618), 4-chloro-phenoxy-acetic acid, 3,3 '-dimethyl-4-methoxy- benzophenone, 1-bromo-4-chloromethylsulfonyl-benzene, 1- [4- (N-2-
- - methoxybenzoylsulfamoyl) -phenyl] -3-methyl-urea (aka N- (2-methoxy-benzoyl) -4- [(methylamino-carbonyl) -amino] -benzenesulfonamide), 1- [4- (N-2- methoxy-benzoylsulfamoyl) -phenyl] -3,3-dimethyl-urea, 1- [4- (N-4,5-dimethylbenzoyl sulphamoyl) -phenyl] -3-methyl-urea, 1- [4- (N-naphthylsulfamoyl ) -phenyl] -3,3-dimethyl-urea, N- (2-methoxy-5-methyl-1-benzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds defined by means of the formulas of the general formula (bundle)
or of the general formula (Ilb)
or of the formula (líe)
where m represents a number 0, 1, 2, 3, 4 or 5, A1 represents one of the divalent heterocyclic groups
- - schematized below
n represents a number 0, 1, 2, 3, 4 or 5, A2 represents alkanediyl optionally substituted with C 1 -C 4 alkyl and / or C 1 -C 4 alkoxycarbonyl and / or C 1 -C 4 alkynyloxycarbonyl with 1 or 2 carbon atoms, R14 represents hydroxy, mercapto, amino, Ci-C alco alkoxy, Ci-Cd alkyl thio, Ci-Ce-amino alkyl or di (C ?C4) alkyl-amino, R15 represents hydroxy, mercapto , amino, C?-C7 alkoxy, C?-C6-oxy alkenyl, C?-C6-oxy-alkoxy Ci-Ce alkoxy, Ci-Cß-thio alkyl, Ci-Ce-amino alkyl or di- (C alkyl? -C4) -amino,
R 16 represents C 1 -C alkyl optionally substituted with fluorine, chlorine and / or bromine, R 17 represents hydrogen, C 1 -C 6 alkyl, C 2 -C 2 alkenyl or C 2 -C 6 alkynyl in each case optionally substituted with fluorine, chlorine and / or bromine , C 1 -C 4 alkoxy C 1 -C 4 alkyl, dioxolanyl C 1 -C 4 alkyl, furyl, furyl C 1 -C alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted with fluorine, chlorine and / or bromine or C? -C alkyl,
R18 represents hydrogen, Ci-Cß alkyl, C2-C6 alkenyl or C2-C6 alkynyl in each case optionally substituted with fluorine, chlorine and / or bromine, C?-C4 alkoxy-C?-C4 alkyl,
- dioxolanyl-C1-C4 alkyl, furyl, furyl-C1-C4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted with fluorine, chlorine and / or bromine or C1-C4 alkyl, R17 and R18 also together represent alean C3 -C6-diylo or oxaalcan-C2-C5-diyl in each case optionally substituted with C1-C4 alkyl, phenyl, furyl, a fused benzene ring or with two substituents which, together with the C atom to which they are attached, form a carbocycle of 5 or 6 members, R19 represents hydrogen, cyano, halogen, or C1-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, R20 represents hydrogen, C? alkyl? C6, C3-C6 cycloalkyl or tri- (C1-C4 alkyl) -silyl in each case optionally substituted with hydroxy, cyano, halogen or C? -C alkoxy,
R21 represents hydrogen, cyano, halogen, or 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, halogenalkyl C? -C, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy,
X2 represents hydrogen, cyano, nitro, halogen, alkyl C?
C4, C?-C 4 halogenalkyl, C 1 -C 4 alkoxy or Ci- C 4 halogenalkoxy, X 3 represents hydrogen, cyano, nitro, halogen, Cι-C 4 alkyl, C halo-C 4 haloalkyl, C 1 -C 4 alkoxy or C halo-haloalkoxy
- -
C4, and / or the following compounds defined by general formulas of the general formula (lid)
or of the general formula (lie)
in which represents a number 0, 1, 2, 3, 4 or 5, represents a number 0, 1, 2, 3, 4 or 5, R 22 represents hydrogen or C? -C4 alkyl, R 23 represents hydrogen or alkyl C? -C4, R 24 represents hydrogen, Ci-Ce alkyl, Ci-Cβ alkoxy, alkoxy
C? -C6, C? -C6 alkylthio, C? -C6alkylamino or di- (Ci- C4alkylamino) in each case optionally substituted with cyano, halogen or C? -C4 alkoxy, or C3 cycloalkyl -C6, C3-C6 cycloalkyl ~ oxy, C3-C6 cycloalkyl-thio or cycloalkyl
C3-C6-amino in each case optionally substituted with cyano, halogen or C? -C4 alkyl,
- -
R 25 represents hydrogen, C 1 -C 6 alkyl optionally substituted with cyano, hydroxy, halogen or C 1 -C 4 alkoxy, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl in each case optionally substituted with cyano or halogenor C3-C6 cycloalkyl optionally substituted with cyano, halogen or C1-C4 alkyl, R26 represents hydrogen, C1-C6 alkyl optionally substituted with cyano, hydroxy, halogen or C1-C4 alkoxy, C3-C6 alkenyl or C3-C6 alkynyl in each case optionally substituted with cyano or halogen, C3-C6 cycloalkyl optionally substituted with cyano, halogen or C1-C4 alkyl, or phenyl optionally substituted with nitro, cyano, halogen, C1-C4 alkyl, C1-C4 halogenalkyl, C1-C4 alkoxy or C1-C4 halogenalkoxy, or together with R25 represents C2-C6-diyl or C2-C5 oxaalcan-diyl in each case optionally substituted with alkyl
C? -C4, X4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C1-C4 alkyl, C? -C4 halogenalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, and X5 represents nitro , cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C3-C4 alkyl, C?-C4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy. The compounds according to the invention are generally defined by the formula (I). Substituents or intervals
Preferred of the formulas mentioned above and subsequently are explained below: X preferably represents methyl and Y preferably represents methyl or ethyl or X and Y both preferably represent ethyl, A preferably represents hydrogen or C? -C? 2 alkyl, C 3 -C 8 alkenyl, C 1 -C 6 alkoxy C 1 -C 8 alkyl, C 1 -C 6 alkyl alkylthio C 6 -C 6 alkyl optionally substituted with halogen, C 3 -C 8 cycloalkyl optionally substituted with halogen, C alkyl -C6 or C6-C6 alkoxy, in which optionally one or two non-directly adjacent ring members are replaced by oxygen and / or sulfur, B preferably represents hydrogen, C? -C? 2 alkyl or C? -C8-alkoxy Ci-Ce alkyl or A, B and the carbon atom to which they are attached represent preferably saturated C3-C10 cycloalkyl or unsaturated C5-C10 cycloalkyl, in which optionally a ring member is replaced by oxygen or sulfur and which are eventually mono - or disubstituted with C? -C8 alkyl, C? -C8 haloalkyl or C? -C8 alkoxy or
A, B and the carbon atom to which they are attached represent preferably C3-C6 cycloalkyl which is substituted with
- - an alkylenediyl group or an alkylenedioxyl group or an alkylenedithioyl group optionally substituted with C1-C4 alkyl optionally containing one or two oxygen and / or sulfur atoms not directly adjacent, which forms with the carbon atom to which it is attached another ring of five to eight members or A, B and the carbon atom to which they are attached represent preferably C3-C8 cycloalkyl or C5-C8 cycloalkenyl, in which two substituents represent together with the carbon atoms to which they are attached alloy C2-C6-diylo, C2-C6 alkenyl or C4-C6 alkanediene-diyl in each case optionally substituted by C? -C6 alkyl, Ci-C? Alkoxy or halogen, in which optionally a methylene group is replaced by oxygen or sulfur, A and Q1 together represent C1-C10 alkyl, Ci-Ce alkoxy, Ci-Ci-thio alkyl, optionally mono- or di-substituted, in the same or different manner, with halogen, hydroxy, in each case optionally mono- to trisubstituted equal mode the different with halogen, C3-C7 cycloalkyl or C2-C6 alean-diyl or C2-C6 alkenyl-diyl substituted with benzyloxy or optionally mono- to trisubstituted phenyl, in the same or different manner, with halogen, Ci-Ce alkyl or Ci-alkoxy -Ce, which also contains one of the following groups
- -
or that is bridged with an alean C? -C2-diyl group or that is interrupted or bridged with an oxygen atom,
Q 1 and Q 2 represent, independently of one another, preferably hydrogen or C 1 -C 4 alkyl, or X represents preferably ethyl and Y represents methyl and a) A, B and the carbon atom to which they are attached represent preferably C 4 -C 8 cycloalkyl. saturated or unsaturated Cs-C8 cycloalkyl, in which optionally a ring member is replaced by oxygen or sulfur and optionally mono- or di-substituted with C?-C8 alkyl, C?-C8 haloalkyl or C?-C8 alkoxy or A , B and the carbon atom to which they are attached represent preferably C3-C6 cycloalkyl which is optionally substituted with an alkylenediyl group, a group
- alkylenedioxyl or an alkylenedithioyl group optionally substituted with C 1 -C 4 alkyl optionally containing one or two oxygen and / or sulfur atoms not directly adjacent, which with the carbon atom to which it is attached forms another ring of five to eight members or TO, B and the carbon atom to which they are attached represent preferably C3-C8 cycloalkyl or Cs-C8 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent alean C2-C6-diyl, alken C2- C6-diylo or alloy C4-C6-diendiyl in each case optionally substituted with Ci-Ce alkyl, C6-C6 alkoxy or halogen, in which optionally a methylene group is replaced by oxygen or sulfur, Q1 and Q2 preferably represent hydrogen, orb) A and Q1 together represent C1-C10 alkyl, Ci-Cß alkoxy, Ci-Cß-thio alkyl, optionally mono- or di-substituted, in the same or different manner, with halogen, hydroxy, in each case optionally mono- to trisubstituted same or different mode with halogen, C3-C7 cycloalkyl or C2-C6-cycloalkyl or C2-C6 alkenyl-diyl substituted with benzyloxy or optionally mono- to trisubstituted phenyl, in the same or different manner, with halogen, Ci-Cß alkyl or Ci-Ce alkoxy, which also contains optionally one of the following groups
- -
or which is bridged with an alloy C? -C2-diyl group or which is interrupted or bridged with an oxygen atom, B and Q2 represent, independently of one another, preferably hydrogen or C? -C2 alkyl, G preferably represents hydrogen (a) or one of the groups
(and)
in particular (a), (b), (c) or (g), in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur,
- - preferably represents C 1 -C 2 alkyl, C 2 -C 2 alkenyl, C 1 -C 8 alkoxy C 1 -C 8 alkyl, C 1 -C 8 alkyl thio C 1 -C 8 alkyl, C 1 -C 8 alkoxy C 1 -C 8 alkyl C8 in each case optionally substituted with halogen, or C3-C8 cycloalkyl optionally substituted with halogen, Ci-Cß alkyl or Ci-Cβ alkoxy, wherein optionally one or more (preferably not more than two) ring members are not directly adjacent are replaced by oxygen and / or sulfur, phenyl optionally substituted with halogen, cyano, nitro, C? -C6 alkyl, C? -C6 alkoxy, C? C6 haloalkyl, Ci-Ce halogenalkoxy, Ci-C? alkyl thio or C alqu-C6-sulfo-nyl alkyl, phenyl-Ci-Cß alkyl optionally substituted with halogen, nitro, cyano, Ci-Cß alkyl, Ci-C alco alkoxy, Ci-Cß haloalkyl or Ci-Cß halogenalkoxy, 5 or 6 hetaryl members optionally substituted by halogen or C? -C6 alkyl (eg, pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl), phenoxy-Ci-C? alkyl optionally substituted halogen or Ci-Cß alkyl or hetaryloxy-C de-C6 alkyl of 5 or 6 members optionally substituted with halogen, amino or C?-C6 alkyl (for example, pyridyloxy-Ci-Cß alkyl, pyrimidyloxy-Ci-C6 alkyl) or thiazolyloxy-C? -C6 alkyl),
- -
R 2 preferably represents C 1 -C 2 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy C 2 -C 8 alkyl, poly C 1 -C 8 alkoxy C 2 -C 8 alkyl optionally substituted with halogen, C 3 -C 8 cycloalkyl optionally substituted with halogen, C?-C6 alkyl or C?-C6 alkoxy or phenyl or benzyl in each case optionally substituted with halogen, cyano, nitro, C?-C6 alkyl, C?-C6 alkoxy, Ci-Cß halogenalkyl or halogenalkoxy Ci -Ce, R 3 preferably represents C 1 -C 8 alkyl optionally substituted with halogen or phenyl or benzyl in each case optionally substituted by halogen, Ci-Ce alkyl, C 1 -C 6 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, cyano or nitro, R.sup.4 and R.sup.5 preferably independently of one another are C? -C8 alkyl, C? -C8 alkoxy, C? -C8 alkyl amino, di- (C? -C8 alkyl) amino, alkyl C? -C8-thio, C2-C8-thio alkenyl, C3-C7 cycloalkyl-thio in each case optionally substituted with halogen or phenyl, phenoxy or phenylthio in each case optionally substituted with halogen, nitro, cyano, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl thio, C 1 -C 4 alkyl or C 2 -C halogenalkyl
C4, R6 and R7 preferably represent, independently of each other, hydrogen, C?-C8 alkyl, C3-C8 cycloalkyl, C?-C8 alkoxy, C3-C8 alkenyl, C?-C8 alkoxy-C?-C8 alkyl in
- - each case optionally substituted with halogen, phenyl optionally substituted by halogen, halogenalkyl C] _ C8, C 1 -C 8 alkyl or C 1 -C 8 alkoxy, benzyl optionally substituted by halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl or Ci-Cβ alkoxy or together represent a C3-C6 alkylene radical optionally substituted by C1-C4 alkyl, in which optionally a carbon atom is replaced by oxygen or sulfur, R13 preferably represents hydrogen, C?-C8 alkyl, C alco alkoxy -Cg or C3-C8 alkenyl-oxy in each case optionally substituted with halogen, C3-C8 cycloalkyl optionally substituted with halogen, C1-C4 alkyl or C1-C4 alkoxy, in which optionally a methylene group is replaced by oxygen or sulfur, or phenyl, hetaryl, phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkoxy or C 1 -C 4 hetarylalkoxy in each case optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 6 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy C4, nitro or cyano, R14a represents preferenteme The hydrogen or C?-C8 alkyl or R13 and R14a together preferably represent C4-C6-diyl alloy, R15a and R16a are the same or different and preferably represent Ci-Ce alkyl or R15a and R16a together preferably represent a C2- C4-say that it is optionally substituted with C? -C6 alkyl, Ci-C? Haloalkyl or phenyl optionally
- - substituted with halogen, Ci-Cß alkyl, halogenalkyl C?
C4, Ci-Cß alkoxy, C?-C 4 halogenalkoxy, nitro or cyano, R 17a and R 18a represent, preferably independently of one another, hydrogen, C?-C8 alkyl optionally substituted with halogen or phenyl optionally substituted with halogen, C 1 -C 4 alkyl -Ce, C6-C6 alkoxy, halogenalkyl
C? -C4, C? -C4 halogenalkoxy, nitro or cyano or R1 and R18a represent, together with the carbon atom to which they are attached, preferably a C5-C7 carbonyl or cycloalkyl group optionally substituted with halogen, C? -C4 alkyl or C? -C4 alkoxy, in which optionally a methylene group is replaced by oxygen or sulfur, R19a and R20a preferably represent, independently of each other, C1-C10 alkyl, C2-C? alkenyl, C1-C10 alkoxy , C 1 -C 0 alkylamino, C 3 -C 20 alkenyl or amino, di- (C 1 -C 10 alkyl) amino or di- (C 3 -C 20 alkenyl) amino. In the definitions of the moieties mentioned as preferred, halogen represents fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine. X represents, with special preference, methyl, Y represents, with special preference, methyl or ethyl, or X and Y both represent with special preference ethyl, A represents, with special preference, hydrogen, Ci-Cß alkyl, C? -C4 alkoxy? -alkyl C? -C2 in each case eventually
- - mono- to trisubstituted with fluorine or chlorine, or C3-C6 cycloalkyl optionally mono- to disubstituted with C? -C2 alkyl or C? -C2 alkoxy, B represents, with special preference, hydrogen, C? -C4 alkyl or alkoxy d-C2-C C-C2 alkyl or A, B and the carbon atom to which they are attached preferably represent especially saturated or unsaturated C5-C7 cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and it is optionally mono- to disubstituted with Ci-Cß alkyl, trifluoromethyl or Ci-Cd alkoxy, A, B and the carbon atom to which they are attached preferably represent, in particular, C 5 -C 6 cycloalkyl, which is substituted by an alkylenediyl or alkylenedioxyl group or alkylenedithiol optionally substituted with methyl or ethyl which optionally contains one or two oxygen or sulfur atoms not directly adjacent, which with the carbon atom to which it is attached form another ring of five or six members, A, B and the carbon atom at q which are attached preferably represent special C3-C6 cycloalkyl or C5-C6 cycloalkenyl, in which two 'substituents together with the carbon atoms to which they are attached represent alloy C2-C4-diyl, C2-C4 alkenyl or butadiene-diol in each case optionally substituted with C? -C2 alkyl or C? -C2 alkoxy,
- -
A and Q1 represent, together with special preference, C3-C4-allyl or C3-C4 alkenyl dial in each case optionally mono- or disubstituted, in the same or different manner, with hydroxy, C?-C2 alkyl or C?-C2 alkoxy , which eventually contains one of the following groups
or which may be interrupted or bridged by an oxygen atom, Q1 and Q2 represent, independently of each other, with special preference hydrogen or C? -C2 alkyl?
X represents, with special preference, ethyl and Y represents, with special preference, methyl and a) A, B and the carbon atom to which they are attached preferably represent especially saturated or unsaturated C5-C7 cycloalkyl, in which optionally a member of the The ring is replaced by oxygen or sulfur and is optionally mono- to disubstituted with Ci-Cß alkyl, trifluoromethyl or Ci-C alco alkoxy, with the proviso that Q 3 then preferably represents hydrogen or methyl, or
- -
A, B and the carbon atom to which they are attached preferably represent special C5-C6 cycloalkyl, which is substituted by an alkylene dicaldeyl or alkylenedioxyl group or alkylene dithiol, optionally substituted by methyl or ethyl optionally containing one or two oxygen or sulfur atoms not directly adjacent, that with the carbon atom to which it is attached forms another ring of five or six memberswith the proviso that then Q3 represents with special preference hydrogen or methyl, A, B and the carbon atom to which they are attached preferably represent special C3-C6 cycloalkyl or C5-C6 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent alloy C2-C4-diyl, C2-C4 alkenyl-diyl or butadye-diyl in each case optionally substituted with C? -C2 alkyl or C? -C2 alkoxy, with the proviso that then Q3 preferably represents hydrogen or methyl, or Q1 and Q2 represent, with particular preference, hydrogen or b) A and Q1 represent, together with particular preference in each case, C3-C4-allyl or C3-C4 alkenyl-diyl optionally mono- or disubstituted , in the same or different manner, with hydroxy, C? -C2 alkyl or C? -C? 2 alkoxy, optionally containing one of the following groups
- -
or is interrupted or bridged by an oxygen atom, B and Q2 represent independently of one another, with special preference, hydrogen or methyl, G represents, with special preference, hydrogen (a) or one of the groups OL AR R? 1 ? < b) .. A. M- * 2 M (c), / S ° r-R * (d), - // R (e),
in particular (a), (b) or (c), in which E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 represents, with special preference, C-alkyl C8, C2-C8 alkenyl, C4-C4 alkoxy-C2-C2 alkyl, C5-C4 alkylthio-C6-C2 alkyl in each case optionally mono- to trisubstituted with fluorine or chlorine or cycloalkyl C3- Cß optionally mono- to disubstituted with fluorine, chlorine, C alquilo-C2 alkyl or C alco-C2 alkoxy, in which optionally one or
- two non-directly adjacent ring members are replaced by oxygen, optionally mono- to disubstituted phenyl with fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl or halogenalkoxy C? -C2, R2 represents, with special preference, C?-C8 alkyl, C2-C8 alkenyl or C alco-C4 alkoxy-C2-C4 alkyl in each case optionally mono- to trisubstituted with fluorine, C-C6 cycloalkyl optionally monosubstituted with alkyl C? -C2 or C? -C2 alkoxy or phenyl or benzyl in each case optionally mono- to disubstituted with fluorine, chlorine, bromine, cyano, nitro, C1-C4 alkyl, C1-C3 alkoxy, trifluoromethyl or trifluoromethoxy, R3 represents, with particular preference, Ci-Ce alkyl optionally mono- to tri-substituted with fluorine or phenyl optionally monosubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R 4 represents, with special preference , C? -C6 alkyl, C? -C6 alkoxy, C? -C6 alkyl amino, di- ( C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl thio, C 3 -C 4 alkenyl thio, C 3 -C 6 cycloalkyl thio in each case optionally mono- to trisubstituted with fluorine or chlorine or phenyl, phenoxy or phenylthio in each case eventually monosubstituted with fluorine, chlorine, bromine,
- - nitro, cyano, C1-C3 alkoxy, C1-C3 halogenalkoxy, Ci- C3 alkyl thio, C?-C3 halogenalkyl thio, C1-C3 alkyl or trifluoromethyl, R5 represents, with special preference, Ci-Cß alkoxy or C 1 -C 6 alkylthio in each case optionally monosubstituted with chlorine, R 6 represents, with special preference, hydrogen, alkyl
Ci-Cd, C3-C6 cycloalkyl, Ci-Cß alkoxy, C3-C6 alkenyl, C?-C6 alkoxy-C1-C4 alkyl, phenyl optionally monosubstituted with fluorine, chlorine, bromine, trifluoromethyl, C?-C4 alkyl or C1-alkoxy -C 4, benzyl optionally monosubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, trifluoromethyl or C 1 -C 4 alkoxy, R 7 represents, with special preference, C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 1 -C 6 alkoxy C 1 -C 6 alkyl -C4, R6 and R7 represent together, with special preference, a C4-C5 alkylene radical optionally substituted with methyl or ethyl, in which optionally a methylene group is replaced by oxygen or sulfur, R13 represents, with special preference, hydrogen, alkyl C? -C8, C? -C8 alkoxy, C3-C6 alkenyl-oxy in each case optionally mono- to trisubstituted with fluorine or chlorine, C3-C8 cycloalkyl optionally substituted with halogen, C1-C4 alkyl or C? -C4 alkoxy, wherein eventually a methylene group is replaced by oxygen or sulfur, or
- phenyl, pyridyl, pyrimidyl, thiazolyl, phenyl-C 1 -C 2 alkyl or pyridyl-C 1 -C 2 alkoxy in each case optionally substituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 halogenalkyl C2, halogenalkoxy C? ~ C2, nitro or cyano, R17a and R18a represent, independently of one another, with particular preference hydrogen, C1-C4 alkyl optionally mono- to tri-substituted with fluorine or chlorine or optionally mono- to disubstituted phenyl with fluorine , chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C?-C 2 haloalkyl, C?-C 2 halogenalkoxy, nitro or cyano or R 17a and R 18a represent, together with the carbon atom to which a group is especially attached carbonyl or C5-C6 cycloalkyl optionally mono- to disubstituted with fluorine, chlorine, C1-C3 alkyl or C1-C4 alkoxy. In the definitions of the residues mentioned with special preference, halogen represents fluorine, chlorine and bromine, especially fluorine and chlorine. X represents, with very special preference, methyl, and represents, with very special preference, methyl or ethyl or X and Y represent both, with very special preference, ethyl,
A represents, with particular preference, hydrogen, C 1 -C 4 alkyl or C 1 -C 2 alkoxy C 2 -C 2 alkyl optionally mono- to tri-substituted with fluorine, or
- - represents cyclopropyl, cyclopentyl or cyclohexyl, B represents, with very special preference, hydrogen, methyl or ethyl or A, B and the carbon atom to which they are attached represent, especially very special saturated C5-C6 cycloalkyl, in the that eventually a ring member is replaced by oxygen and that it is optionally monosubstituted with methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy, A, B and the carbon atom to which they are attached represent, preferably very special, cycloalkyl Ce, which is substituted with an alkylenedioxyl group containing two oxygen atoms not directly adjacent to each other which, with the carbon atom to which it is attached, forms another five or six membered ring, A, B and the The carbon to which they are attached represent, with particular preference, C5-C6 cycloalkyl or C5-C6 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached are present alloy C2-C4-diyl or C2-C4 alkenyl-diyl or butadiene-diol, A and Q1 represent together, with very special preference, alloy
C3-C4-diyl or C3-C4 alkenyl diyl optionally mono- or disubstituted, in the same or different manner, with hydroxy, methyl or methoxy optionally containing one of the
- - following groups
or which may be interrupted or bridged by an oxygen atom, Q1 and Q2 represent, independently of one another, with very special preference hydrogen or methyl or X represents, with very special preference, ethyl and Y represents, with very special preference, methyl, and A) A, B and the carbon atom to which they are attached represent, with very special preference, saturated C5-C6 cycloalkyl in which eventually a ring member is replaced by oxygen or sulfur and which is optionally monosubstituted with methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy, A, B and the carbon atom to which they are attached represent, with particular preference, C6 cycloalkyl, which is substituted with an alkylenedioxyl group containing two carbon atoms. oxygen not directly adjacent, which, with the carbon atom to which it is attached, forms another ring of
- - five or six members, A, B and the carbon atom to which they are attached represent, with very special preference, C5-C6 cycloalkyl or C5-C6 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached they are attached represent alloy C2-C4-diyl or alken C2-C4-diyl or butadiendiyl, Q1 and Q2 represent, with very special preference, hydrogen or b) A and Q1 represent together, with very special preference, alloan C3-C4-diyl or C3-C4 alkenyl diyl optionally mono- or disubstituted with hydroxy, methyl or methoxy which optionally contain one of the following groups
or that is interrupted or bridged by an oxygen atom, B and Q2 represent, with particular preference, independently of each other, hydrogen or methyl, G represents, with special preference, hydrogen (a) or one of the groups
- - in which E represents an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 represents, with very special preference, Ci-Cß alkyl, C2-C6 alkenyl, C alco-C2 alkoxy Ci alkyl, C 1 -C 2 alkyl thioalkyl Ci or C 3 -C 6 cyclopropyl optionally monosubstituted with fluorine, chlorine, methyl or methoxy or C 1 -C 4 alkyl monosubstituted with chlorine, phenyl optionally monosubstituted with fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R2 represents, with particular preference, C?-C8 alkyl, C2-C6 alkenyl or C?-C4 alkoxy-C2-C3 alkyl in each case optionally mono- to tri-substituted with fluorine, phenyl or benzyl, R3 represents, with very special preference, Ci-Ce alkyl, R4 represents, with very special preference, C1-C4 alkyl, C1-C4 alkoxy, C 1 -C 4 alkyl amino, di- (C 1 -C 4 alkyl) amino, alkyl C? -C4-thio, C3-C4-thio alkenyl, C3-C6 cycloalkyl-thio in each case optionally mono- to trisubstituted with fluorine or chlorine or phenyl, phenoxy or phenylthio in each case optionally monosubstituted with fluorine, chlorine, bromine, nitro, cyano, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methyl or trifluoromethyl,
- -
R 5 represents, with very special preference, C 1 -C 4 alkoxy or C 1 -C 4 alkyl thio optionally monosubstituted with chlorine,
R 13 preferably represents very special C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 3 -C 4 alkenyl-oxy in each case optionally mono- to trisubstituted with fluorine or chlorine or represents benzyl or pyridyl in each case optionally substituted with fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R17a and R18a represent, independently of one another, with particular preference C 1 -C 4 alkyl optionally mono- to tri-substituted with fluorine or chlorine or optionally mono- to disubstituted phenyl with fluorine, chlorine, bromine , methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano or
R17a and R18a represent together with the carbon atom to which they are attached, very particularly preferably C5-C6 cycloalkyl optionally mono- or di-substituted with methyl or ethyl, X represents notably methyl, Y represents notably methyl or ethyl, or X and Y represent both notably ethyl, A represents mainly methyl, B represents notably hydrogen or methyl or A, B and the carbon atom to which they are attached, stand out prominently saturated C5-C6 cycloalkyl in which
- optionally one member of the ring is replaced by oxygen and optionally is monosubstituted with methyl, A and Q1 together stand out prominently C3-C5-diyl or C3-C5 alkenyl-diyl in each case possibly monosubstituted with methyl, which optionally contain one of the following groups
Q1 and Q2 represent prominently hydrogen, or X represents notably ethyl and Y represents notably methyl and a) A, B and the carbon atom to which they are attached, stand out prominently saturated C5-C6 cycloalkyl, in which eventually a member of the ring is replaced for oxygen, Q1 and Q2 represent notably hydrogen or b) A and Q1 together stand out prominently C3-C5-diyl or C3-C5 alkenyl-diyl in each case possibly monosubstituted with methyl, which eventually contain one of the following groups
- - or which is interrupted or bridged by an oxygen atom, B and Q2 represent, independently of one another, notably hydrogen, G represents notably hydrogen (a) or one of the following groups
wherein L represents oxygen and M represents oxygen, R1 represents notably Ci-Ce alkyl, C? -C2 alkoxy C? -C2 alkyl, or C? -C4 alkyl monosubstituted with chlorine, R2 represents notably C? -C8 alkyl, R4 represents, in particular, C.sub.1 -C.sub.4 alkoxy which is optionally monosubstituted with chlorine, R.sub.5 represents, in particular, C.sub.4 -C.sub.4 alkoxy, which is optionally monosubstituted with chlorine, R.sub.17a and R.sub.18 represent notably methyl. Especially preferred are isomerically pure compounds of the formula (I ') in which X and Y represent, independently of one another, methyl or ethyl, and
- -
G represents the remains of very special preference,
r-e > s l'-trans where trans compounds stand out in particular. The definitions of the remains or detailed explanations in general or at previously preferred intervals can be combined with each other, ie, in any way between the corresponding intervals and preferred ranges. They are valid for the final products, as well as for the precursors and intermediate products. Preferred according to the invention are compounds of formula (I) in which a combination of the meanings previously explained as preferred (preferably) is present. Particularly preferred according to the invention are the compounds of the formula (I) in which a combination of the previously explained meanings is present as being particularly preferred. Especially preferred according to the invention are compounds of the formula (I) in which a
- - combination of the meanings explained previously as very special preference. According to the invention, the compounds of the formula (I) are particularly preferred in which a combination of the meanings explained above is present. Saturated or unsaturated hydrocarbon residues such as alkyl, alkanediyl or alkenyl can be linear or branched, if possible, also in combination with heteroatoms such as, for example, in alkoxy. The optionally substituted radicals can be mono- or polysubstituted, unless otherwise indicated, where in the case of polymers, the substituents can be the same or different. In particular, in addition to the compounds mentioned in the preparation examples, the following compounds of the formula (I-1-a) can be mentioned:
Table 1: X = CH 3 / Y CH 3 r Q2 = H
- -
- -
- -
- - Table 2: X = C2H5, Y = C2H5, 0 /
- -
- -
Table 3: X = C7H, Y = CH 13,
- -
- -
- -
The preferred meanings of the groups enumerated above in relation to the compounds that improve the tolerance of the crop plants (herbicide crop protectors) of the formulas (Ha), (Hb), (He), (lid) and (He ) are defined below. m preferably represents the numbers 0, 1, 2, 3 or 4.
A1 preferably represents one of the divalent heterocyclic groups schematized below
n preferably represents the numbers 0, 1, 2, 3 or 4. It preferably represents methylene or ethylene in each case optionally substituted with methyl, ethyl, methoxycarbonyl or ethoxycarbonyl, R? preferably represents hydroxy, 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 hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, 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 . R16 preferably represents methyl, ethyl, n- or i-propyl in each case optionally substituted with fluorine, chlorine and / or bromine, R17 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, propenyl, butenyl, propynyl 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, n- or i-propyl, n-, i-, s- or t-butyl, R18 preferably represents hydrogen, methyl, ethyl, n- or 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
- - optionally substituted with fluorine and / or chlorine, or phenyl optionally substituted with fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or R17 and R18 represent also together one of the residues -CH2-0-CH2- CH2- and -CH2-CH2-0-CH2-CH2, which are optionally substituted with methyl, ethyl, furyl, phenyl, a fused benzene ring or with two substituents which, together with the C atom to which they are attached, they form a 5 or 6 member carbocycle. R 19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine. R20 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted with hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. R21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine. X1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
- butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. X2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl , methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. X3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl , methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. t preferably represents the numbers 0, 1, 2, 3 or 4. v preferably represents the numbers 0, 1, 2, 3 or 4.
R22 preferably represents hydrogen, methyl, ethyl, n- or i-propyl. R 23 preferably represents hydrogen, methyl, ethyl, n- or i-propyl. R 24 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, n-, i-, s- or t -butoxy, methylthio, ethylthio, n- oi-
- propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino in each case optionally substituted with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclo- butylamino, cyclopentylamino or cyclohexylamino in each case optionally substituted with cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl. R 25 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl in each case optionally substituted with cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl each optionally substituted by cyano, fluorine, chlorine or bromine, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl. R 26 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl in each case optionally substituted with cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl in each case optionally substituted with cyano,
- - fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or phenyl optionally substituted with nitro, cyano, fluorine , chlorine, bromine, methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, or together with R25 represents butan-1,4-diyl (trimethylene), pentan-1,5-diyl, 1-oxa-butan-l, 4-diyl or 3-oxa-pentan-l, 5-diyl in each case optionally substituted with methyl or ethyl. X4 preferably nitro, cyano, represents carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. X5 preferably nitro, cyano, represents carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. Examples of the compounds of the formula (Ha) which are very preferred as herbicidal culture protectants according to the invention are detailed in the following table.
- -
Table: Examples of the compounds of the formula (Ha)
- -
- -
- -
Examples of the compounds of the formula (Ilb) which are very particularly preferred as herbicidal culture protectants according to the invention are listed in the following Table.
Table: Examples of the compounds of the formula (Hb)
- -
- -
Examples of the compounds of the formula (I) which are very preferred as herbicidal culture protectants according to the invention are detailed in the following Table.
Table: Examples of the compounds of the formula (He)
- -
Examples of the preferred compounds of the formula (Hd) as herbicidal culture protectants according to the invention are detailed in the following Table.
Table: Examples for the compounds of the formula (Hd)
- -
- -
Examples of the compounds of the formula (He) which are very preferred as herbicidal culture protectants according to the invention are detailed in the following Table.
- -
Table: Examples of the compounds of the formula (He)
- -
As a compound that improves the tolerance of crop plants [component (b ')], cloquintocetmexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenchlorim, cumylurone, dimrone, dimethoperate and He-5 compounds are preferred. and He-11, emphasizing in particular cloquintocetmexilo and mefenpir-dietilo. Examples of the selective herbicidal combinations according to the invention of an active ingredient of the formula (1) and one of the crop protectors defined above are detailed in the following Table.
Table: Examples of the combinations according to the invention
- -
15 20 25
- -
15 20 25
- -
15 20 25
- -
The compounds of the general formula (Ha) for use as culture protectants according to the invention are known and / or can be prepared according to the processes known per se (cf. documents OA 91/07874, WO-A-95/07897 ). The compounds of the general formula (Hb) for use as culture protectants according to the invention are known and / or can be prepared according to the processes known per se (EP-A-191736). The compounds of the general formula (He) for use as culture protectants according to the invention are known and / or can be prepared according to the processes known per se (cf. DE-A-2218097, DE-A-2350547) . The compounds of the general formula (lid) for use as culture protectants according to the invention are known and / or can be prepared according to the processes known per se (cf. DE-A 19621522 / US-A-6235680). The compounds of the general formula (He) for use as culture protectants according to the invention are known and / or can be prepared according to the processes
- known per se (document O-A99 / 66795 / US-A-6251827).
It has now surprisingly been found that the above-defined active ingredient combinations of compounds of the general formula (I) and culture protectants (antidotes) of the above-mentioned group (b ') exhibit a particularly high herbicidal efficacy with very good tolerance in useful plants and can be used in various crops, especially in cereals (especially wheat), but also in soybeans, potatoes, corn and rice, for the selective control of weeds.
In this regard, it should be considered surprising that, from a number of known crop protectors or antidotes which are capable of antagonizing the harmful effect of a herbicide on crop plants, just the compounds detailed above in group (b ') are suitable for almost completely canceling out the harmful effect of the compounds of the formula (I) on the crop plants, without substantially impairing the herbicidal efficacy against weeds in this case. In this regard, the particularly advantageous effect of the preferred and highly preferred combination partners of group (b ') is particularly noteworthy, especially as regards the care of cereal plants such as, for example, wheat, barley and rye, but also corn and rice, as crop plants. If it is used, for example, according to the procedure (A) 5- (2-ethyl-4,6-dimethyl-f-enyl) -2,3-tetramethylene-4-oxo-valerianic acid ethyl ester, the The course of the process according to the invention can be reproduced by means of the following
- - reaction scheme:
If it is used, for example, according to the procedure
(B) 2- (2-ethyl-4,6-dimethyl-phenyl) -4,4-dimethylcyclopentan-1,3-dione and pivaloyl chloride as starting substances, the course of the process according to the invention can be reproduced by middle of the following reaction scheme:
If, for example, according to process (B) 2- (2, 6-diethyl-4-methyl-phenyl) -4,4-pentamethylene-1,3-dione and acetanhydride are used as starting compounds, the The course of the process according to the invention can be reproduced by means of the following reaction scheme:
If it is used, for example, according to the procedure C) 2- [(2,6-diethyl-4-methyl) -phenyl] -4,5-tetramethylene-cyclopentan-
- -
1,3-dione and ethyl ester of chloroformic acid as starting compounds, the course of the process according to the invention can be reproduced by means of the following reaction scheme:
if it is used, for example, according to the procedure (D) 2 - [(2,4,6-triethyl-phenyl] -4,5-tetramethylenecyclopentan-1,3-dione and methyl ester of chloromonothioformic acid as compounds of Starting, the course of the process according to the invention can be reproduced by means of the following scheme and reaction:
If it is used, for example, according to the procedure (E) 2- (2,6-diethyl-4-methyl-phenyl) -5,5-pentamethylene-cyclopentane-1,3-dione and methanesulfonic acid chloride as starting product, the course of the procedure can be reproduced
- - means of the following reaction scheme:
If it is used, for example, according to the procedure (F) 2- (2-ethyl-4,6-dimethyl] -phenyl) -4,4-dimethylcyclopentan-1,3-dione and (2, 2, 2) -trifluoroethyl ester) of metanthiophosphonic acid as starting products, the course of the process can be reproduced by means of the following reaction scheme:
If, for example, according to the procedure (G) 2- (2-ethyl-4,6-dimethyl-phenyl] -4,4-dimethylcyclopentan-1,3-dione and NaOH are used as components, the course of the The process according to the invention can be reproduced by means of the following reaction scheme: Na (+)
If it is used, for example, according to the procedure
- -
(H), variant a, 2- (2-ethyl-4,6-dimethyl-phenyl) -4,4-tetramethylene-cyclopentan-1,3-dione and ethyl isocyanate as starting materials, the course of the process can be reproduce by means of the following reaction scheme: O
II H
If used, for example, according to process (H), variant B, 2- (2,6-diethyl-4-methyl-phenyl) -5,5-pentamethylene-cyclopentan-1,3-dione and chloride of dimethylcarbamic acid as starting products, the course of the procedure can be reproduced by means of the following scheme:
The compounds of the formula (II) required in the process (A) according to the invention as starting substances
gave)
- - in which A, B, Q1, Q2, X, Y and R8 have the meanings indicated above, are new. They can be prepared by methods known in principle. The 5-aryl-4-ketocarboxylic acid ester of the formula (II) is obtained, for example, if they are esterified (cf., for example, Organikum, 15th Edition, Berlin, 1977, page 499) or alkylated ( see preparation example) 5-aryl-4-10 ketocarboxylic acids of the formula (XIII)
i r where X, Y, A, B, Q1 and Q2 have the meanings indicated above. The 5-aryl-4-ketocarboxylic acids of the formula (XIII)
where A, B, Q1, Q2, X and Y have the meanings indicated above, are new, but can be prepared according to methods in
- - known principle (WO 96/01798, WO 97/14667, WO 98/39281, WO 01/74770). The 5-aryl-4-ketocarboxylic acids of the formula (XIII) are obtained, for example, if 2-phenyl-3-oxo-adipic acid esters of the formula (XIV) are decarboxylated
wherein A, B, Q1, Q2, X and Y have the meanings indicated above and R8 and R8 'represent alkyl (especially Ci-Cß alkyl) and by using the compound of the formula (XVI), R8 represents hydrogen , optionally in the presence of a diluent and optionally in the presence of a base or acid (cf., for example, Organikum, 15th Edition, Berlin, 1977, pages 519 to 521). The compounds of the formula (XIV)
in which
- -
A, B, Q1, Q2, X, Y, R8, R8 'have the meanings indicated above and when using the compound of the formula (XVI), R8 represents hydrogen, they are new. The compounds of the formula (XIV) are obtained, for example, by acylating dicarboxylic acid half-ester chlorides of the formula (XV)
wherein A, B, Q1, Q2 and R8 have the meanings indicated above and Hal represents chlorine or bromine, or carboxylic acid anhydrides of the formula (XVI)
wherein A, B, Q1 and Q2 have the meanings indicated above, with an ester of phenylacetic acid of the formula (XVII)
- -
wherein X, Y and R8 'have the meanings indicated above, in the presence of a diluent and in the presence of a base (cf., for example, MS Chambers, EJ Thomas, DJ Williams, J. Chem. Soc. Chem Commun., (1987), 1228, also compiles the preparation examples). The compounds of the formulas (XV) and (XVI) are partially known compounds of organic chemistry and / or can be prepared in a simple manner according to methods known in principle. The acid halides of the formula (III), carboxylic acid anhydrides of the formula (IV), esters of chloroformic acid or thioesters of chloroformic acid of the formula (V), esters of chloromonothioformic acid or esters of chlorodithioformic acid of the formula (VI), sulfonic acid chlorides of the formula (VII), phosphorus compounds of the formula (HIV) and metal hydroxides, metal alkoxides or amines of the formulas (IX) and (X) and isocyanates of the formula
(XI) and carbamic acid chlorides of the formula (XII) necessary for carrying out the processes (B), (C), (D), (E), (F), (G) and (H) according to the invention are composed of
- - the organic or inorganic chemistry known in general. The compounds of the formulas (XV), (XVI) and (XVII) are known, beyond this, from the patent applications cited at the beginning and / or can be prepared according to the methods indicated therein. The process (A) is characterized in that the compounds of the formula (II) are subjected, in which A, B, Q1, Q2, X, Y and R8 have the meaning indicated above, in the presence of a base to an intramolecular condensation. . Suitable diluents in the process (A) according to the invention are all organic solvents which are inert with respect to the reaction partners. Preferably, hydrocarbons such as toluene and xylene can be used, also ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol, tert.-butanol may also be used. As bases (deprotonation agents), all customary proton acceptors can be used in the process (A) according to the invention. Preferably alkali metal or alkaline earth metal oxides, hydroxides and carbonates can be used, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, carbonate
- - sodium, potassium carbonate and calcium carbonate, the molar quantities in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride. But it is also possible to use one or another component in a greater excess (up to 3 moles). The process (B-a) is characterized in that compounds of the formula (I-a) are reacted in each case with carboxylic acid halides of the formula (III) optionally in the presence of a diluent and optionally in the presence of an acid acceptor. Suitable diluents for the process (B-a) according to the invention are all solvents which are inert to the acid halides. Preferably, hydrocarbons such as benzine, benzene, toluene, xylene and tetralin can be used, also halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methylisopropyl ketone, also ethers such as as diethyl ether, tetrahydrofuran and dioxane, beyond this, carboxylic acid esters such as ethyl acetate and also strongly polar solvents such as dimethyl sulfoxide and sulfolane. When the hydrolysis stability of the acid halide allows it, the reaction can also be carried out in the presence of water. As acid acceptors are taken into account in the
- reaction according to process (B-a) according to the invention, all customary acid acceptors. Preferably, tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig base and N, N-dimethylaniline, also alkaline earth metal oxides such as magnesium oxide and calcium, also alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide. The reaction temperatures can be varied in the process (B-a) according to the invention within a wide range. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C. In carrying out the process (B-a) according to the invention, the starting substances of the formula (I-a) and the carboxylic acid halide of the formula (III) are used in general in almost equivalent amounts. However, it is also possible to use the carboxylic acid halide in a greater excess (up to 5 moles). The processing is carried out according to usual methods. The process (B-β) is characterized in that compounds of the formula (I-a) are reacted with carboxylic acid anhydrides of the formula (IV) optionally in the presence of a diluent and optionally in the presence of a
- Acid acceptor. Preferred diluents in process (B-ß) according to the invention are those diluents which are also preferably taken into account when using acid halides. In addition, a carboxylic acid anhydride used in excess can also act as a diluent at the same time. Possible added acid acceptors in the process (B-β) are preferably those acid acceptors which are also preferably taken into account when using acid halides. The reaction temperatures can be varied in the process (B-ß) according to the invention within a wide range. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C. In carrying out the process (B-ß) according to the invention, the starting substances of the formula (I-a) and the carboxylic acid anhydride of the formula (IV) are used in general in almost equivalent amounts. However, it is also possible to use the carboxylic acid anhydride in a greater excess (up to 5 moles). The elaboration is carried out according to usual methods. In general, the procedure is carried out in such a way that excess solvent and carboxylic acid anhydride are eliminated, as well as the carboxylic acid produced by
- - distillation or by washing with an organic solvent or water. The process (C) is characterized in that compounds of the formula (Ia) are reacted in each case with esters of chloroformic acid or thioesters of chloroformic acid of the formula (V) optionally in the presence of a diluent and optionally in the presence of an acceptor of acids. As acid acceptors, all the customary acid acceptors are taken into account in the reaction according to process (C) according to the invention. Preferably, tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hünig base and N, N-dimethylaniline can be used, also alkali metal oxides, such as magnesium and calcium oxide, also alkali metal carbonates and alkaline earth metals such as sodium carbonate, potassium carbonate and calcium carbonate, as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide. Suitable diluents for the process (C) according to the invention are all solvents which are inert to the esters of chloroformic acid or thioesters of chloroformic acid. Preferably hydrocarbons such as benzine, benzene, toluene, xylene tetralin, also halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and
- - Methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane, beyond which carboxylic acid esters such as ethyl acetate, and also strongly polar solvents such as dimethyl sulfoxide and sulfolane. The reaction temperatures can be varied by carrying out the process (C) according to the invention within a wide range. If working in the presence of a diluent and an acid acceptor, the reaction temperatures will generally be between 20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C. The process (C) according to the invention is generally carried out at normal pressure. In carrying out the process (C) according to the invention, the starting substances of the formula (I-a) and the corresponding chloroformic acid ester or thioester of chloroformic acid of the formula (III) are used in general in almost equivalent amounts. However, it is also possible to use one or another component in a greater excess (up to 2 moles). The processing is carried out according to usual methods. In general, the procedure is carried out in such a way that the salts produced are eliminated and the residual reaction mixture is concentrated by extraction of the diluent. The process (D) according to the invention is characterized in that compounds of the formula (I-a) are reacted in each case with compounds of the formula (VI) in the presence of a
- - diluent and possibly in the presence of an acid acceptor. In the preparation process (D), about 1 mole of chloromonothioformic acid ester or chlorodithioformic acid ester of the formula (VI) from 0 to 10 is reacted per mole of the starting compound of the formula (I-a).
120 ° C, preferably 20 to 60 ° C. Suitable optionally added diluents are all inert polar organic solvents such as ethers, amides, sulfones, sulfoxides, but also halogenalkanes. Preferably, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are used. If it is obtained in an embodiment by the addition of strong deprotonation agents such as, for example, sodium hydride or potassium tert-butylate the enolate salt of the compounds (Ia), the subsequent addition of acid acceptors can be dispensed with. acids. If acid acceptors are used, then customary inorganic and organic bases are taken into account, by way of example, sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine are enumerated. The reaction can be carried out at normal pressure or at elevated pressure, preferably at normal pressure. The processing is carried out according to usual methods.
- -
The process (E) according to the invention is characterized in that compounds of the formula (Ia) are reacted in each case with sulphonic acid chlorides of the formula (VII) optionally in the presence of a diluent and optionally in the presence of an acid acceptor . In the preparation process (E), about 1 mole of sulphonic acid chloride of the formula (VII) is reacted per mole of the starting compound of the formula (Ia) from -20 to 150 ° C, preferably from 20 to 150 ° C. at 70 ° C. Suitable optionally added diluents are all inert polar organic solvents such as ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride. Preferably, dimethylsulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are used. If it is obtained in the preferred embodiment by the addition of strong deprotonation agents (such as, for example, sodium hydride or potassium tert-butylate) the enolate salt of the compounds (Ia), the subsequent addition can be dispensed with of acid acceptors. If acid acceptors are used, customary inorganic or organic bases are taken into account, by way of example, sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine are enumerated. The reaction can be carried out at normal pressure or at
- - high pressure, preferably working at normal pressure.
The processing is carried out according to usual methods. The process (F) according to the invention is characterized in that compounds of the formula (I-a) are reacted in each case with phosphorus compounds of the formula (HIV) optionally in the presence of a diluent and optionally in the presence of an acid acceptor. In the preparation process (F), the compounds of the formula (Ie) are reacted to obtain 1 mole of the compounds (Ia), 1 to 2, preferably 1 to 1.3 moles of the phosphorus compound of the formula ( HIV) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C. Suitable optionally added diluents are all inert polar organic solvents such as ethers, amides, nitriles, alcohols, sulphides, sulfones, sulfoxides, etc. Preferably, acetonitrile, dimethylsulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are used. Suitable optionally added acid acceptors are the customary inorganic or organic bases such as hydroxides, carbonates or amides. By way of example, sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine are listed. The reaction can be carried out at normal pressure or at
- - high pressure, preferably working at normal pressure. The processing is carried out according to the usual methods of organic chemistry. The purification of the final products produced is preferably carried out by crystallization, chromatographic purification or by so-called distillation, ie separation of the volatile components under vacuum. The process (G) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (IX) or amines of the formula (X), optionally in the presence of a diluent. Diluents which can be used in the process (G) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or also alcohols such as methanol, ethanol, isopropanol, but also water. The process (G) according to the invention is generally carried out at normal pressure. The reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C. The process (H) according to the invention is characterized in that compounds of the formula (Ia) are reacted in each case with compounds (Ha) of the formula (XI) optionally in the presence of a diluent and optionally in the presence of a catalyst or ( H-ß) with compounds of the formula (XII) optionally in the presence of a diluent and
- - possibly in the presence of an acid acceptor. In the process (Ha) according to the invention, about 1 mole of isocyanate of the formula (XI) is reacted per mol of the starting compound of the formula (Ia) from 0 to 100 ° C, preferably from 20 to 50 ° C. C. Suitable optionally added diluents are all inert organic solvents such as ethers, amides, nitriles, sulphones, sulfoxides. Eventually, catalysts can be added to accelerate the reaction. As catalysts, organotin compounds, such as, for example, dibutyltin dilaurate, can be used very advantageously. Preferably working at normal pressure. In the preparation process (H-ß), about 1 mole of carbamidoid acid chloride of the formula (XII) is reacted per mole of the starting compound of the formula (Ia) from -20 to 150 ° C, preferably from 0 to 70 ° C. Suitable optionally added diluents are all inert polar organic solvents such as ethers, amides, sulfones, sulfoxides or halogenated hydrocarbons. Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride. If in a preferred embodiment by adding strong deprotonation agents (such as, for example, hydride
- of sodium or potassium tert-butylate) the enolate salt of the compound (I-a) is obtained, the subsequent addition of acid acceptors can be dispensed with. If acid acceptors are used, then customary inorganic or organic bases are taken into account, for example, sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine are mentioned. The reaction can be carried out at normal pressure or at elevated pressure, preferably at normal pressure. The processing is carried out according to usual methods. The active ingredients according to the invention are suitable with a good phytotolerance, favorable toxicity in warm-blooded animals and good tolerance in the environment, for the protection of plants and plant organs to increase the production of the crop, improve the quality of the harvest and to combat animal parasites, especially insects, arachnids, helminths, nematodes and molluscs, which occur in agriculture, in gardening, in livestock breeding, in logging, in gardens and leisure facilities, in protection of stocks and materials, as well as in the health sector. They can be preferably used as phytosanitary agents. They are active against species of normal and resistant sensitivity, as well as against all or some stages of growth. To the aforementioned parasites, belong:
- -
From the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp. From the Aracnida class, for example, Acarus siro, 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., Ceutho-rhynchus 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, Hypo-thenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, 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 chryso-cephala, 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 helminth class, 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, Enterobius 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.
- -
You can also fight 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, Brachycolus spp., Brevicoryne brassicae, Calli-gypona marginata, Carneocephala fulgida, Ceratovacuna lanígera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis
- - spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Meto-polophium 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, 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 Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
- -
From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asel'lus, 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., Barias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanimous, Hyponomeuta padella, La- phygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossy-piella, Phyllocnistis citrella, Pieris spp. , Plutella xylo-stella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellion she, 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, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of the Thysanura, for example, Lepisma saccharina. Phytoparasitic nematodes belong, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursa-phelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp. The compounds according to the invention can optionally be used in certain concentrations or application amounts also as herbicides, crop protectants, growth regulators or agents to improve the properties of the plants, or as microbiocides, for example.
- - example, such as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLO (organism type mycoplasma) and RLO (organism type Rickettsia). They can also be optionally used as intermediates or precursors for the synthesis of other active ingredients. According to the invention, all plants and parts of the plant can be treated. By plants are meant, in this case, all plants and plant populations as wild or desired and unwanted plants or crop plants (including natural crop plants). Crop plants can be plants that can be obtained through breeding and optimization methods or by biotechnological or genetic technology methods or combinations of these methods, including transgenic plants and plant varieties that can be protected or not by rights of variety protection. By parts of plants are understood all the parts and organs of aerial and subterranean plants, such as bud, leaf, flower and root, enumerating by way of example leaves, needles, stems, trunks, flowers, ascocarps, fruits and seeds, as well as as roots, bulbs and rhizomes. The harvested material, as well as vegetative and generative reproductive material, for example, seedlings, bulbs, rhizomes, layering and seeds, belong to the parts of the plants. The treatment according to the invention of plants and parts
- - of the plants with the active ingredients is carried out directly or by action on their surroundings, habitat or deposit according to the usual treatment methods, for example, by immersion, pouring, spraying, evaporation, fogging, dispersion, spreading, injection and, in the case of reproduction material, especially in seeds, also by coating one or more layers. The active ingredients can be converted into the customary formulations such as solutions, emulsions, spray powders, water and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for dispersion, suspension concentrates. emulsion, natural substances impregnated with active principle, synthetic substances impregnated with active principle, fertilizers, as well as fine encapsulations in polymeric substances. These formulations are prepared in a known manner, for example, by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie, emulsifiers and / or dispersants and / or generators. foam. The preparation of the formulations is carried out either in appropriate facilities or also before or after the application. As adjuvants you can use those substances that
- - are suitable for granting the agent itself and / or preparations derived therefrom (eg spray liquors, seed disinfectants) particular properties, such as certain technical properties and / or also special biological properties. Typical coadjuvants are: extenders, solvents and vehicles. Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, for example, of the aromatic and non-aromatic hydrocarbon varieties (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also optionally be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (also fats and oils) and (poly-) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide). If water is used as an extender, organic solvents can also be used as auxiliary dissolving agents. Suitable liquid solvents are essentially aromatic substances such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic substances and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions. from
- - petroleum, mineral and vegetable oils, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, as well as water. As solid carriers, we take into account: for example, ammonium salts and natural flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic flours such as highly dispersed silicic acid, aluminum oxide and silicates, as solid vehicles for granulates are taken into account: for example, broken and fractionated natural stones such as calcite, marble, pumice stone, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic material such as paper, sawdust, coconut husks, corn cobs and tobacco stems; the following are considered as emulsifying and / or foaming agents: for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ether, for example, alkylaryl-polyglycol ether, alkyl sulfonates , alkyl sulfates, aryl sulfonates, as well as albumin hydrolysates; as dispersants, non-ionic and / or ionic substances are taken into account, for example, of the alcohol ether-POE and / or POP ether, acid ester and / or POP-POE varieties,
- - alkyl-aryl ether and / or POP-POE, fatty adducts and / or POP-POE, POE- and / or POP-polyol derivatives, POE- and / or POP-sorbitan adducts or sugar adducts, alkyl or aryl sulfates, sulphonates and phosphates or the corresponding PO-ether adducts. In addition, suitable oligo- or polymers, for example, starting from vinyl monomers, acrylic acid, EO and / or PO alone or in combination with, for example, (poly-) alcohols or (poly-) amines. Lignin and its sulphonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids, as well as their formaldehyde adducts can also be used. They can be used in adhesive formulations such as carboxymethylcellulose, natural and synthetic polymers, powders, granules or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Dyes can be used as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metallo phthalocyanine dyes and trace elements such as iron, manganese, boron, copper salts, of cobalt, molybdenum and zinc. Other additives may be flavorings, mineral oils or optionally modified oils, waxes and
- - nutrients (also trace elements), such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. Stabilizers such as cold stabilizers, preservatives, oxidizing agents, photoprotective agents or other agents that improve chemical and / or physical stability may also be present. The formulations generally contain between 0.01 and 98% by weight of active principle, preferably between 0.5 and 90%. The active principle according to the invention can exist in its usual commercial formulations, as well as in the forms of application prepared from these formulations in admixture with other active ingredients such as insecticides, baits, sterilizers, bactericides, acaricides, nematicides, fungicides, growth regulating substances, herbicides, crop protectors, fertilizers or semiochemicals. Especially suitable mixing partners are, for example, the following: Fungicides: Nucleic acid synthesis inhibitors: benalaxyl, benalaxyl-M, bupirimate, chirallaxyl, clozilacona, dimethirimol, etirimol, furalaxyl, himexazole, metalaxyl, metalaxyl-M, ofurace , oxadixilo, oxolinic acid
- -
Inhibitors of mitosis and cell division: benomyl, carbendazim, dietofencarb, etaboxam, fuberidazole, pencicuron, thiabendazole, thiophanate-methyl, zoxamide Inhibitors of the respiratory chain complex I diflumetorima Inhibitors of the respiratory chain complex II: boscalide, carboxin, fenfuram, flutolanil, furametpir, mepronil, oxycarboxine, pentiopyrad, tifluzamide Inhibitors of the respiratory chain complex III azoxystrobin, ciazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, cresoxim-methyl, meto-minostrobin, orisastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin Discouplers dinocap, fluazinam Inhibitors of the production of ATP fentin acetate, fentin chloride, fentin hydroxide, siltiofam Inhibitors of amino acid and protein biosynthesis andoprima, blasticidin-S, cyprodinil, casugamicin, hydrated casugamicin hydrochloride, mepanipyrim, pyrimethanyl Inhibitors of signal transduction phenpiclonil, fludioxonil, quinoxifene Inhibitors of lipid and membrane synthesis
- - clozolinate, iprodione, procymidone, vinclozoline ampropilfos, ampropilfos-potasio, edifenfos, iprobenfos (IBP), isoprothiolane, pyrazophos tolclofos-methyl, biphenyl, iodocarb, propamocarb, propamocarb hydrochloride Inhibitors of ergosterol biosynthesis: azaconazole, bitertanol, bromuconazole , cycloconazole, diclobutrazol, diphenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, protioconazole, simeconazole, tebuconazole, tetraconazole, triadimefonone , triadimenol, triticonazole, uniconazole, voriconazole, imazalil, imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pirifenox, triforine, pefurazoate, prochloraz, triflumizole, viniconazole, almimorf, dodemorf, dodemorf acetate, fenpropinomorf, tridemorph, fenpropidine, spiroxamine , naftifina, piributicarb, terbinafina Inhibitors of cell wall synthesis bentiavalicarb, bialafos, dimetomorf, flumorf, iprovalicarb, polioxinas, polioxorima, validamicina A Inhibitors of melanin biosynthesis carpropamide, diclocimet, phenoxanil, phthalide, pyroquilone,
- - triciclazole Induction of acibenzolar-S-methyl resistance, probenazole, thiadinyl Multisite captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxin copper and Bordeaux mixture, diclofluanide, dithianone, dodin, dodin free base, ferbam, folpet, fluorofolpet, guazatin, guazatin acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, copper man, mancozeb, maneb, metiram, zinc metiram , propineb, sulfur and sulfur preparations containing calcium polysulfide, thiram, tolyl fluanide, zineb, ziram Unrecognized mechanism amybromdol, benthiazole, betoxazine, capsymycin, carvone, chlomenethione, chloropicrin, cufraneb, cyflufenamide, cymoxanil, dazomet, debacarb, diclomezine , dichlorophene, dichloro, difenzoquate, methyl diphezolate sulfate, diphenylamine, etaboxam, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, hexachlorobe ncene, 8-hydroxyquinoline sulfate, irumamycin, metasulfocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrotal-isopropyl, octylinone, oxamocarb, oxyfentin, pentachlorophenol and salts,
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2-phenylphenol and salts, piperalin, sodium propanosine, proquinazide, pyrrolnitrine, quintozene, tecloftalam, tecnazene, triazoxide, triclamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylisulfonyl) -pyridine, N- (4- chloro-2-nitrofenyl) -N-ethyl-4-methyl-benzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1, , 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chloro-enyl) -2, 3-dimethylisoxazolidin-3-yl] pyridine, cis-l- (4-chlorophenyl) ) -2- (lH-1,2, 4-triazol-l-yl) -cycloheptanol, 2,4-dihydro-5-metox i-2-methi 1-4 - [[[[l- [3- (trifluoromethyl) -phenyl] -ethyl] -amino] -oxi] -methyl] -phenyl] -3H-l, 2,3-triazol-3-one (185336-79-2), 1- (2, 3 methyl-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- (metoxime ti len) -benzacetate, -chloro-α-a-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] -benzacetamide, (2S) -N- [2- [4- [[3- (4 chlorophenyl) -2-propynyl] oxy] -3-methoxy phenyl] ethyl] -3-methyl-2- [(methylisulfonyl) 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-trif luorofenyl) -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-trif luorofenyl) [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) met i 1-2, 4-dichloronicotinamide, 2-butoxy-6-iodo-3-propyl- benzopiranon-4-
- - ona, N-. { (Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2, 3-difluorophenyl] methyl} -2-benzacetamide, N- (3-ethyl-3,5,5-trimethyl-1-cyclohexyl) -3-formylamino-2-hydroxy-benzamide, 2- [[[[1- [3- (1-fluoro-2 phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha- (methoxyimino) -N-methyl-alpha-E-benzacetamide, N-. { 2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3 ', 4'-dichloro-5-fluorobipheni1-2-yl) -3- (difluoromethyl) -1-methy1-lH-pyrazole-4-carboxamide, N- (6 -methoxy-3-pyridinyl) -cyclopropanecarboxamide, 1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, 0- [1 - [(4-methoxyphenoxy) methyl] -2, 2-dimethylpropyl] -1H-imidazole-1-carbothioic acid, 2- (2 { [6- (3-Chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy}. ) -2- (methoxyimino) -N-methylacetamide Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, casugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: Acetylcholinesterase inhibitors (AChE) carbamates, for example, alanicarb, aldicarb, aldoxicarb, alixicarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxicarboxim, carbaryl, carbofuran, carbosulfan, cloetocarb, dimethylan, etiofencarb, fenobucarb,
- - phenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimetacarb, XMC, xylilcarb, triazamate organophosphate, for example, acetate, azamethiphos, azinphos ( -methyl, -ethyl), bromido-ethyl, bromophenvinphos (-methyl), butathiophos, cadusafos, carbophenothione, chloroethoxyphos, chlorophenvinphos, chloromephos, chlorpyrifos (-methyl / -ethyl), coumaphos, cyanofenphos, cyanophos, chlorophenvinphos, demetone-S- methyl, demetone-S-methylsulfone, dialiphos, diazinone, diclofenthione, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinfos, dioxa-benzofos, disulfotone, EPN, ethion, ethoprofos, etrimfos, famfur, fenamiphos, fenitrothione, fensulfothione, fenthion, flupirazophos, fonofos, formotione, fosmetilano, fostiazato, heptenofos, iodophenfos, iprobenfos, isazofos, isofenfos, 0-isopropil salicilate, isoxationa, malathion, mecarbam, methacryphos, methamidophos, methidathione, mevinfos, monocrotofos, naled, ometoato, Oxydemetone-methyl, parathion (-methyl / -ethyl), phenoate, phorate, phosalone, phosmet, phosphamidone, phosphocarb, foxima, pirimiphos (-methyl / -ethyl), profenofos, propafos, propetanfos, protiofos, protoato, piraclofos, pyridafenthione, pyridathione, quinalfos, sebufos, sulfotep, sulprofos, tebupirimfos, temefos, terbufos, tetrachlorvinfos, thiometone, triazofos, trichlorfona, vamidotiona
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Sodium channel modulators / pyrethroid-dependent sodium channel blockers, eg, acrinatrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, isomer of bio-acetyl-S-cyclopentyl , bioetanometrin, biopermethrin, bioresmethrin, clovaportrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocitrin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, teta-, zeta-), cyphenothrin, deltamethrin, empentrin ( IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpiritrin, fenvalerate, flubrocitrinate, flucitrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprotrin, cadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-) , phenothrin (1R-trans isomer), praletrin, profluthrin, protrifenbute, piresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, teralethrin, tetramethrin (isomer -1R-), tralometrine, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)
DDT oxadiazines, for example, indoxacarb semicarbazone, for example, metaflumizone (BAS3201)
- -
Acetoncholine receptor agonists / antagonists, eg, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitiazine, thiacloprid, thiamethoxam nicotine, bensultap, cartap Acetylcholine receptor modulators spinosyn, for example, spinosad chloride channel antagonists controlled by GABA organochlorines, for example, camphechlor, chlorodane, endosulfan, gamma-HCH,
HCH, heptachlor, lindane, methoxychlor fiproles, eg acetoprol, etiprole, fipronil, pyrafluprol, pyriprole, vaniliprole Chondroitin channel activators mectins, eg, abamectin, emamectin, emamectin benzoate, ivermectin, lepimectin, milbemycin Hormone mimetics juvenile, eg, diofenolane, epofenonane, phenoxycarb, hydroprene, quinoprene, methoprene, pyriproxyfen, triprene Ecdysone agonists / diacylhydrazine disruptors, eg, chromafenozide, halofenozide, methoxyfenozide,
- - tebufenozide Chitin biosynthesis inhibitors benzoylureas, for example, bistriflurone, clofluazurone, diflubenzurone, fluazurone, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron buprofezin, cyromazine Inhibitors of oxidative phosphorylation, ATP disruptors diafentiurone organotin compounds, for example, azocyclotin, cyhexatin, fenbutatin oxide
Decoupling of oxidative phosphorylation by interruption of the proton gradient H pyrrole, for example, chlorophenapyr dinitrophenols, for example, binapacirl, dinobutone, dinocap, DNOC, meptidinocap Inhibitors of electron transport of the I side MET, for example, fenazaquine, fenpyroximate, pyrimidifen , pyridaben, tebufenpirad, tolfenpirad hidrametilnona
- - dicofol Inhibitors of electron transport of the II side rotenones Inhibitors of electron transport of side III acequinocyl, fluacripirim Microbial disruptors of the intestinal membrane of insects strains of Bacillus thuringiensis Inhibitors of the synthesis of tetronic acid fats, for example, spirodiclofen , spiromerase, tetramic acids, for example, cis-3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1-azaspiro [4.5] dec-3-en-2-one carboxamides, eg, flonicamide octopaminergic agonists, eg, amitraz Inhibitors of magnesium-stimulated ATPase, nereistoxine-like propargites, eg, thiocyclic hydrogen oxalate, thiosultap-sodium
Rianodine receptor agonists, benzoic acid dicarboxamides, for example, flubendiamide
- - anthramylamides, for example, rinaxipir (3-bromo-N-. {4-chloro-2-methyl-6- [(methylamino) carbonyl] phenyl} - l- (3-chloropyridin-2-yl) -lH-pyrazole-5-carboxamide) Biological agents, hormones or pheromones azadirachtin, Bacillus spec., Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticillium spec. Active ingredients with unknown or non-specific mechanisms of action gasification agents, for example, aluminum phosphide, methyl bromide, sulfuryl fluoride, anti-nutritive agents, for example, cryolite, flonicamide, pymetrozine Mite growth inhibitors, for example, clofentezine, ethoxazole, hexythiazox amidoflumet, benclotiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlorodimeform, chlorobenzilate, chloropicrin, clotiazobeno, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, phentrifanil, flubenc-imine, flufenner, flutenzian, gosiplure, hydramethylnon, japonilure, methoxadiazone , petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sulfluramide, tetradiphone, tetrasul, triaratene, verbutin.
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A mixture with other known active ingredients such as herbicides, fertilizers, growth regulators, crop protectants, semiochemicals, or even agents to improve the properties of the plants is also possible. The active ingredients according to the invention can also be used as insecticides in their commercially available formulations, as well as in the application forms prepared from these formulations in admixture with synergists. The synergists are compounds through which the action of the active principles increases, without the added synergist having to be active in itself. The active principles according to the invention can also be present, when applied as insecticides, in their commercially available formulations, as well as in the forms of application prepared from these formulations in mixtures with inhibitors which reduce a degradation of the active principle after use. in the surroundings of the plant, on the surface of plant parts or in plant tissues. The content of active principle of the forms of application prepared from the formulations customary in the market can vary in wide ranges. The concentration of active principle of the application forms can vary from 0.00000001 to 95% by weight of active principle, preferably between 0.00001 and 1% by weight. The application is made in a usual way appropriate to
- - the forms of application. As already mentioned above, all the plants and their parts can be treated according to the invention. In a preferred embodiment, species and varieties of wild plants or obtained by conventional biological breeding methods such as cross or fusion of proto-plastids, as well as their parts are treated. In another preferred embodiment, plants and varieties of transgenic plants that were obtained with genetic engineering methods are treated eventually in combination with conventional methods (genetically modified organism) and their parts. The terms "parts" or "parts of plants" were explained previously. With special preference, according to the invention plants of the usual plant varieties are treated in each case in the market or in use. Plant varieties are plants with new properties ("traits"), which were raised either by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be varieties, biotypes or genotypes. Depending on the varieties of plants or plant varieties, their location and growth conditions (soils, climate, vegetative period, food), superaditive effects ("synergists") may also appear due to the treatment according to the invention. In this way, they are possible,
- - for example, smaller amounts of application and / or enlargements of the spectrum of action and / or an increase in the action of the substances and agents useful according to the invention, better growth of the plant, greater tolerance to high or low temperatures, greater tolerance to drought or water content or saline soil, greater flowering capacity, simpler harvest, acceleration of ripening, higher harvest products, higher quality and / or higher nutritional value of harvested products, greater capacity in storage and / or processability of harvested products, which go beyond the effects actually expected. Among the plants or varieties of transgenic plants (obtained by genetic technology) preferred, to be treated according to the invention, are all the plants that received genetic material by modification of genetic technology, which gives these advantageous plants valuable properties ("traits" "). Examples of such properties are better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or water content or saline soil, greater flowering, easier harvest, acceleration of ripening, higher harvest products , higher quality and / or higher nutritional value of harvested products, greater storage capacity and / or processability of harvested products. Other specially highlighted examples of the properties are a greater
defense of plants against animal and microbial parasites, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, as well as a greater tolerance of plants to certain herbicidal active principles. As examples of transgenic plants are mentioned the main crops such as cereals (corn, rice), corn, soybeans, potatoes, beets, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with fruit apples , pears, citrus and grapes), especially corn, soybeans, potatoes, cotton, tobacco and rape. As properties ("traits") special emphasis is placed on the greater defense of plants against insects, arachnids, nematodes and snails because of the toxins that are produced in plants, especially those generated by the genetic material of Bacillus thuringiensis ( example, by the genes Cry? A (a), Cry? A (b), Cry? A (c), CrylIA, CrylIIA, CryIHB2, Cry9c, Cry2Ab, Cry3Bb and CrylF, as well as their combinations) in plants (from now on, "Bt plants"). As properties ("traits") the greater defense of plants against fungi, bacteria and viruses by acquired systemic resistance (SAR), systemin, phytoalexins, triggers, as well as resistance genes and proteins and toxins expressed correspondingly stand out. As properties ("traits"), the greater tolerance of plants against certain
- herbicidal active ingredients, for example, imidazolinones, sulfonylureas, glyphosates or phosphinothricin (for example, "PAT" gene). The genes that give the desired properties in each case ("traits") can also appear in combination with each other in the transgenic plants. Examples of "Bt plants" include corn varieties, cotton varieties, soya varieties and potato varieties, which are marketed under the trade names of YIELD GARD® (for example, corn, cotton, soybeans), KnockOut® (for example, corn), StarLink® (for example, corn), Bollgard® (cotton), Nucotn®
(cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants include corn varieties, cotton varieties and soybean varieties that are marketed under the trade names Roundup Ready® (glyphosate tolerance, eg, corn, cotton, soy), Liberty Link ® (tolerance to phosphinothricin, for example, rapeseed), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, eg corn). As herbicide-resistant plants (conventionally reared with herbicide tolerance), varieties marketed under the name of Clearfield® (eg, corn) must also be mentioned. In fact, these explanations also apply to varieties developed in the future or that are released in the future to the market with these properties or with properties developed in the future ("traits").
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The listed plants can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I or with the mixtures of active principles according to the invention. The preferred ranges indicated above in the case of the active ingredients or mixtures also apply to the treatment of these plants. The treatment of plants with the compounds or mixtures enumerated in particular in the present text should be particularly emphasized. The active ingredients according to the invention not only act on parasites of plants, health and reserves, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as tick-borne ticks, skin ticks, mangy mites, Trombidiidae, flies (choppers and suckers), larvae of parasitic flies, lice, malophagus and fleas. To these parasites belong: From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. From the order of the Mallophagidae and the suborders Amblycerina, as well as 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,
- - as well as 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., 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. From the order of 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 ingredients of the formula (I) according to the invention are also suitable for the control of arthropods, animals useful in agriculture such as, for example, cows, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens , turkeys, ducks, geese, bees, other domestic animals such as, for example, dogs, cats, domesticated birds, aquarium fish, as well as so-called test animals such as, for example, hamsters, guinea pigs, rats and mice. With the combat of these arthropods, they should reduce the deaths and the reduction of the (in meat, milk, wool, skins, eggs, honey, etc.), so that it is possible with the application of the active principles according to the invention more economical and simpler animal handling. The application of the active ingredients according to the invention is carried out in the veterinary field and in the handling of the animals in a known manner by enteral administration in the form of, for example, tablets, capsules, brewajes, potions, granules, pastes, boluses,
- - feed-through procedure, suppositories, by parenteral administration, for example, by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of for example immersion or bathing, spraying, pouring (pour-on and spot-on), washing, dusting, as well as with the help of molded bodies containing active ingredients such as neck bands, ear markers, tail markers, limb bands, halfters, devices of dialing, etc. In the application for livestock, poultry, pets, etc., the active principles of the formula (I) can be used as formulations (for example, powders, emulsions, fluid agents), which contain the active ingredients in an amount of 1. 80% by weight, directly or after a dilution of 100 to 10,000 times, or can be used as a chemical bath. It was further found that the compounds according to the invention show a great insecticidal action against insects that destroy the technical materials. By way of example and preferably -without establishing a limitation-, the following insects should be mentioned: 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 spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicala, Reticulitermes flavipes,
Reticulitermes santonensis, Reticulitermes lucifugus, Masto-termes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Campodeidae as Lepisma saccharina. By technical materials are understood in the present context non-living materials such as preferably plastics, adhesives, glues, papers and boards, leather, wood, wood processing products and paints. The ready-to-use agents can optionally contain other insecticides and optionally one or more fungicides. As for the possible additional mixing partners, remission is made to the aforementioned insecticides and fungicides. At the same time, the compounds according to the invention can be used to protect the vegetation from objects, especially boats, screens, nets, constructions, springs and
- - signal installations related to seawater or brackish water. In addition, the compounds according to the invention can be used alone or in combination with other active ingredients as antifouling agents. The active ingredients are also suitable for combating animal parasites in domestic protection, hygiene and stocks, especially insects, arachnids and mites that appear in closed environments such as, for example, departments, factory rooms, offices, booths drivers, etc. They can be used to combat these parasites alone or in combination with other active ingredients or auxiliary agents in domestic insecticidal products. They are active against sensitive and resistant species, as well as against all stages of development. To these parasites belong: From the order of the Scorpionidea, for example, Buthus occitanus. From the order of the Acariña, for example, Argas persicus, Argas reflexus, Bryobia ssp., 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, Araneidae.
- -
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Ophalis 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, 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, Pemphigus spp., Phylloera vastatrix, Phthirus pubis. From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans. Application in the area of household insecticides
- - is carried out alone or in combination with other appropriate active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neo-nicotinoids, growth regulators or active ingredients of other known varieties of insecticides. The application is made in aerosols, pressure-free spraying media, for example, spray and pump sprays, foggers, foggers, foams, gels, evaporation products with cellulose or plastic vaporizer plates, liquid evaporators, gel and membrane evaporators, evaporators operated with propeller, evaporation systems without energy or passives, papers for moths, sacks for moths and gels for moths, such as granulates or powders, in dispersed baits or stations with baits. The active compounds according to the invention can also be used as defoliants, desiccants, weed killers and especially as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the case of the following plants: dicotyledonous weeds of the species: 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, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xantium. Dicotyledonous crops of the species: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. Monocotyledonous weeds of the species: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Oats, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera , Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Monocotyledonous crops of the species: Allium, Ananas, Asparagus, Oats, Hordeum, Oryza, Panicum, Saccharum, Sécale, Sorghum, Triticale, Triticum, Zea.
- -
However, the use of the active ingredients according to the invention is by no means limited to these species, but also extends to other plants. The active principles are appropriate depending on the concentration for the total control of weeds, for example, in industrial plants and roads, and in roads and squares with and without vegetation. Likewise, the active ingredients according to the invention can be used for the control of weeds in perennial crops, for example, forests, ornamental wood plants, fruit trees, vineyards, citrus fruits, nuts, bananas, coffee, tea, rubber, palm oleifera, cocoa, red fruits and hops, in decorative and sport grass and meadows, as well as for the selective control of weeds in annual crops. The active principles according to the invention show a strong herbicidal efficacy and a broad spectrum of action in the use on the soil and in aerial parts of plants. They are appropriate to a certain degree also for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the preemergence and postemergence procedures. The active ingredients can optionally be used in certain concentrations and amounts of application also for the control of harmful parasites and phyto-fungal or bacterial diseases. Can be used
- - optionally also as intermediates and precursors for the synthesis of other active principles. The active ingredients can be converted into customary formulations such as solutions, emulsions, powders for spraying, suspensions, powders, dedusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic substances impregnated with active principle, as well as fine encapsulations in polymeric substances. These formulations are prepared in a known manner, for example, by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie, emulsifiers and / or dispersants and / or generators. foam. If water is used as an extender, organic solvents can also be used as auxiliary dissolving agents. Suitable liquid solvents are essentially aromatic substances such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic substances and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg fractions. of petroleum, mineral and vegetable oils, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones as
- - acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. As solid carriers, we take into account: for example, ammonium salts and natural flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic flours such as highly dispersed silicic acid, aluminum oxide and silicates, as solid vehicles for granulates are taken into account: for example, broken and fractionated natural stones such as calcite, marble, pumice stone, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic material such as paper, sawdust, coconut husks, corn cobs and tobacco stems; the following are considered as emulsifying and / or foaming agents: for example, non-ionogenic and ananic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ether, for example, alkylaryl-poly-glycol ether ether, sulfonates of alkyl, alkyl sulfates, aryl sulfonates, as well as albumin hydrolysates; as dispersants, account is taken, for example, lignin-sulphite bleach and methylcellulose. They can be used in adhesive formulations such as carboxymethylcellulose, natural and synthetic polymers, powders, granules or in the form of latex, such as rubber.
- - Arabica, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes can be used as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metallo phthalocyanine dyes and trace elements such as iron, manganese, boron, copper salts, of cobalt, molybdenum and zinc. The formulations generally contain between 0.1 and 95% by weight of active principle, preferably between 0.5 and 90%. The active ingredients according to the invention can be used for the control of weeds as such or in their formulations also in mixture with known herbicides and / or with substances that improve tolerance in crop plants ("crop protectors"), being possible Ready-to-use formulations or tank mixes. Mixtures with weed control agents containing one or more known herbicides and a culture protector are also possible. For the mixtures, known herbicides are taken into account, for example, acetochlor, acifluorfen (-sodium), aclonifen, alachlor, aloxydim (-sodium), ametryn, amicarbazone, amidochlor, amidosulfuron, aminopyralide,
- - anilofos, asulam, atrazine, azafenidina, azimsulfurona, beflubutamida, benazolina (-ethyl), benfuresato, bensulfurona (-metilo), bentazone, bencarbazona, benzfendizona, benzobiciclona, benzofenap, benzoilprop (-ethyl), bialafos, bifenox, bispiribac ( -sodium), bromobutide, bromophenoxy, bromoxynil, butachlor, butafenacil (-alyl), butroxydim, butylate, cafenstrol, caloxydim, carbetamide, carfentrazone (-ethyl), clometoxifene, chloramben, chloridazone, chlorimurone (-ethyl), clomitrofen, chlorosulfuron, chlorotholurone, cinidone (-ethyl), cinmetilin, cinosulfuron, clefoxidim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralide, clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine, cibutrin, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2, 4-D, 2,4-DB, desmedipham, dialate, dicamba, dichloroprop (-P), diclofop (-methyl), diclosulam, dietyl (-ethyl), difenzoquat, diflufenican, diflufenzopir, dimefurone, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimexiflam, dinitramine, diphenamide, diquat, dithiopyr, diurone, dimrona, epropodane, EPTC, esprocarb, ethalfluralin, etametsulfuron (-methyl), etofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl), -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazine, flumipropine ,
- - flumetsulam, fluomefurona, fluorochloridone, fluoroglucofen (-ethyl), flupoxam, flupropacil, flurpirsulfuron (-methyl, sodium), flurenol (-butyl), fluridone, fluroxipir (-butoxypropyl, -methyl), flurprimidol, flurtamone, flutiacet (- methyl), flutiamide, fomesafen, foramsulfuron, glufosinate
(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxifop
(-ethoxyethyl, -P-methyl), hexazinone, HOK-201, imazametabenz-methyl), imazametapyr, imazamox, imazapic, imazapyr, imazaquina, imazetapir, imazosulfurona, yodosulfurona (-methyl, -sodium), ioxinilo, isopropalina, isoprofurona, isourone, isoxaben, isoxachlorothol, isoxaflutole, isoxapirifop, lactofen, lenacilo, linurone, MCP A, mecoprop, mefenacet, mesosulfuron, mesotrione, metamifop, metamitrone, metazachlor, methabenzthiazurone, methobenzurone, metobromurone, (alpha-) metolachlor, metosulam, methoxuron, metribuzin , metsulfuron (-methyl), molinate, monolinurone, naproanilide, napropamide, neburone, nicosulfuron, norflurazone, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxasulfuron, oxaziclomephone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxsulam, pentoxazone, fenmedifam, picolinafeno, pinoxadeno, piperofos, pretilacloro, primisulfurona (-methyl), profluazol, prometrina, propacloro, propanil, propaquizafop, propisocloro, propoxic arbazone (-sodium), piroxsulam, propizamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl),
- - pyrasulfotol, pyrazoglyl, pyrazolate, pyrazolulfurone (-ethyl), pyrazoxyphene, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalide, pyriminobac (-methyl), pyrimisulfane, piritiobac (-sodium), piroxasulfone, quinclorac, quinmerac, quinoclamine, quizalofop ( -P-ethyl, -P-tefuril), rimsulfuron, sethoxydim, simazine, symmetry, sulcotrione, sulfentrazone, sulfomefurone (-methyl), sulfosate, sulfosulfuron, tebutam, tebutiurone, tembotrione, tepraloxidim, terbutilazine, terbutrine, tenilchlor, thiafluamide, thiazopyr , thiencarbazone-methyl, thidiazimine, thifensulfuron (-methyl), thiobencarb, thiocarbazil, topramezone, tralcoxydim, trialate, triasulfuron, tribenurone (-methyl), triclopyr, tridifan, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron and
- -
A mixture with other known active ingredients is also possible, such as fungicides, insecticides, acaricides, nematicides, substances protecting the damage caused by birds, plant nutrients and soil structure improving agents. The active ingredients or active compound combinations can be used as such, in the form of their formulations or the forms of application prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is carried out in the usual manner, for example, by pouring, spraying, spraying, dispersing. The active principles or combinations of active principles can be applied both before and after the emergence of the plants. They can also be incorporated into the soil before planting. The amount of active principle applied can vary over a large range. It depends essentially on the type of the desired effect. In general, the application amounts are between 1 g and 10 g of active ingredient per hectare of soil surface, preferably between 5 g and 5 kg per ha. The advantageous effect of tolerance in plants of
The culture of the active compound combinations according to the invention is marked quite strongly in certain concentration ratios. However, the weight ratios of the active ingredients in the active compound combinations can be varied in relatively large ranges. In general, to 1 part by weight of active ingredient of the formula (I) correspond to 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, with particular preference 0.05 to 20 parts by weight of one of the compounds (antidotes / culture protectants) tolerance enhancers in crop plants mentioned above in (b '). The active compound combinations according to the invention are generally applied in the form of ready-to-use formulations. The active principles contained in the active compound combinations can also be mixed in formulations. individual when applied, that is, in the form of tank mixes. For certain application purposes, especially in the post-emergence process, it may also be advantageous to apply mineral or vegetable tolerable oils in the formulations as other additives.
- - plants (for example, the commercial preparation "Rako Binol") or ammonium salts such as, for example, ammonium sulfate or ammonium rodanide. The new active compound combinations can be applied as such, in the form of their formulations or the forms of application prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is carried out in the usual manner, for example, by pouring, spraying, spraying, powdering or dispersing. The application rates of the active compound combinations according to the invention can vary within a certain range; they depend, among other things, on climate and soil factors. In general, the application amounts range between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha, with special preference between 0.01 and 0.5 kg per ha. The active compound combinations according to the invention can be applied before and after the emergence of the plants, that is, in the pre-emergence and post-emergence procedures. The culture protectants to be used according to the invention can be used according to their
- - properties for the pretreatment of the seed of the crop plant (disinfection of the seeds) or can be incorporated before planting in the furrows or applied separately before the herbicide or together with the herbicide before or after the emergence of the plants . As examples of plants, important crop plants such as cereals are mentioned
(wheat, barley, rice), corn, soy, potato, cotton, rapeseed, turnips, sugar cane, as well as fruit plants
(with fruits apples, pears, citrus fruits and grapes), especially cereals, corn, soybeans, potatoes, cotton and rape.
The term "active ingredients" also always includes the active compound combinations mentioned herein. The preparation and use of the active principles according to the invention are apparent from the following examples. Preparation examples Examples I-a-1 and I-a-2
(11-1) (l-a-1) < μa-2)
- -
2.50 g (7.9 mmol) of trans-2- [(2-ethyl-4,6-dimethylphenyl) acetyl] -cyclohexanecarboxylic acid methyl ester and 1.77 g of potassium tert-butylate (15.8 g). mmol) are placed in 20 ml of anhydrous dimethylformamide and heated for 3 h to 50 ° C. After cooling, it is poured into ice water, acidified with 2N hydrochloric acid to pH 2 and extracted with ethyl acetate. The organic phase is washed twice more with water, dried (magnesium sulfate) and evaporated on a rotary evaporator. The residue is chromatographed with hexane / ethyl acetate (v / v = 60:40) on silica gel. Fraction A: Trans-isomeric Ia-1 Yield: 0.94 g (42%) Melting point: 196-197 ° C Fraction B: cis-isomeric Ia-2 Yield: 0.60 g (27%) Melting point : 220-221 ° C
Analogously to Example (I-1-a-1 and I-a-2) and in accordance with the general indications for the preparation, the following compounds of the formula (I-a) are obtained
00
fifteen
CD
fifteen
o
fifteen
- -
E use I-b-l
To 0.300 g (1.0 mmol) of trans-2- [(2-ethyl-4,6-dimethylphenyl) -3-hydroxy-hexahydro-lH-inden-l-one in 5 ml of chloroform and 0.5 ml of triethylamine are poured into 0.13 g (1.2 mmol) of isobutyric acid chloride and after stirring for 1 hour at room temperature it is poured into ice. After suspending in chloroform, wash with water and dilute hydrochloric acid, dry (magnesium sulfate) and evaporate on a rotary evaporator. Subsequent chromatography on silica gel (ethyl acetate / hexane v / v = 70:30) gives 0.31 g (83%) of the desired product as a colorless oil. H-NMR (400 MHz, CDC13): d = 1.10 (d, 6H), 2.42 (me, 2H), 2.62 (me, 2H), 2.98 (e, 1H), 6.82 -6.90 (m, 2H) ppm
Example I-b-2
- -
To a mixture of 0.2 g (0.54 mmol) of the compound according to Example Ib-43 and 2 ml of 0.5 molar solution of sodium hydrogencarbonate in 10 ml of dichloromethane is added 133 mg (0, 6 mmol) of m-chloroperbenzoic acid and stirred for 2 h at room temperature. It is then extracted in 30 ml of dichloromethane, washed with 10% potassium carbonate solution and water, dried (magnesium sulfate) and evaporated on a rotary evaporator. Chromatography on silica gel (ethyl acetate / hexane v / v = 80:20) gives 0.12 g (58%) of the desired product (isomeric mixture) as a colorless oil. NMR-XH (400 MHz, CDC13): d = 2.67 (d, br, 1H), 2.75 (me, 1H), 3.20 (me, 1H), 3.27 (me, 1H), 3.33 (s, 3H), 4.07 (s, 2H) ppm Analogously to Example (Ib-1) and in accordance with the general indications for the preparation, the following compounds of the formula (Ib) are obtained
I heard
fifteen
in
fifteen
n
fifteen
Ü1
fifteen
00
- -
ID
o
fifteen
s >
- -
-)
fifteen
- > v
fifteen
0
- -
Example I-c-1
To 0.200 g (0.7 mmol) of trans-2- [(2-ethyl-4,6-dimethylphenyl) -3-hydroxy-hexahydro-lH-inden-l-one (Example Ia-1) in 5 ml of chloroform and 05 ml of triethylamine is poured in 75 mg (0.7 mmol) of chloroformic acid ethyl ester and stirred for 1 h at room temperature. The mixture is diluted with approximately 30 ml of chloroform, passed to a separating funnel and washed successively with water, 2 N hydrochloric acid and again with water, dried (magnesium sulfate) and after distilling off the solvent, chromatography in silica gel (ethyl acetate / hexane v: v = 90:10). 0.21 g (84%) of the title compound is thus obtained in the form of a colorless oil. NMR-XH (400 MHz, CDC13): d = 1.08 (t, 3H), 1.13 (t, 3H), 2.62 (me, 1H), 3.01 (me, 1H), 4, 18 (q, 2H), 6.90 (me, 2H) ppm
Analogously to Example (I-c-1) and in accordance with the general indications for the preparation, the following compounds of the formula (I-c) are obtained
0 5
00
fifteen
fifteen
^ 1 or
fifteen
- -
Example I-e-1
(Compound Example Ic-1) Analogously (Example 1c-1), 0.30 g (1 mmol) of cis-2- (ethyl-4,6-dimethylphenyl) -3-hydroxy- is obtained. hexahydro-lH-inden-1-one and 0.18 g (1 mmol) of phosphoric acid diethyl ester chloride after column chromatography (ethyl acetate / hexane v: v = 85:15) 0.29 g ( 65%) of the title compound as a colorless oil. RMNAH (300 MHz, CDC13): d = 1.08-1.20 (m, 9H), me = 1.95 (me, 2H), 2.10 and 2.25 (each s, each 3H), 2 , 82 (me, 1H), 3.65-3.92 (m, 4H), 6.85 (me, 2H) ppm Analogously to Example (Ie-1) and in accordance with the general indications for the preparation, obtain the following compounds of the formula (Ie)
0 ^ J
co
fifteen
^ J I
fifteen
^ 1 in
fifteen
in a rotary evaporator, approximately 10 g of solid are obtained
- - the next reaction stage. Reflux 5.0 g (16.5 mmol) of this intermediate product in 30 ml of acetone together with 2 g of potassium carbonate and 5 g (35 mmol) of iodomethane for 4 h, then extract in ethyl acetate. ethyl, stir with water, dry
(magnesium sulfate) and the solvent is distilled. After chromatography on silica gel with ethyl acetate / hexane
(v / v = 80:20), 2.69 g (52%) of the desired methyl 2- [2-ethyl-2,6-dimethylphenyl) acetyl] -cyclohexanecarboxylic acid methyl ester are obtained in the form of colorless crystals. NMR-XH (400 MHz, CDC13): d = 1.17 (t, 3H), 2.17 and 2.26 (each t, each 3H), 2.48 (q, 2H), 2.72 (me) , 1H), 2.88 (me, 1H), 3.60 (s, 3H), 3.93 (AB system, 2H), 6.94 and 6.97 (each s, each 1H) ppm Analogously to Example (II-1) and in accordance with the general indications, the compounds of the formula (II) necessary for the process (A) are obtained. In addition, the compounds of the formula (II) are obtained according to the procedure described below:
< U-3 01-4). (U-5)
1/5 ml of osmium tetroxide solution (2.5 M solution)
- - in ter. -butanol), 860 mg of N-methylmorpholine oxide (NMO) and 2.0 g (6.0 mmol) of methyl 6- (2,6-diethyl-4-methylphenyl) acetyl] cyclohex-3-methyl ester Incarboxylic in 15 ml of acetone are stirred for 12 h at room temperature. 700 mg of sodium dithionite are added, stirred for 30 min at room temperature and then extracted with ethyl acetate. After drying (magnesium sulfate) and evaporating in a rotary evaporator, approximately 1.8 g of viscous oil remain, which is extracted in 5 ml of dimethoxypropane and after adding 20 g of p-toluenesulfonic acid, it is stirred for 8 h at room temperature. Later, the reaction mixture is washed with 10% aqueous potassium carbonate solution, dried (magnesium sulfate) and evaporated on a rotary evaporator. 1.05 g of the compound (II-5) are thus obtained. NMR-XH (300 MHz, CDC13): d = 1.45 (s, 3H), 1.52 (s, 3H),
2.88 (me, 1H), 3.20 (me, 1H), 3.39 (me, 1H) ppm Analogously to Example (II-1) and in accordance with the general preparation procedures, the following compounds are obtained of the formula (II):
- -
OR
CO or
Analogously to Example (XII-1) and according to the general indications of preparation, the following compound of the formula (XIII) is obtained:
- -
> - >
Description of the trials Example A 1. Pre-emergence herbicidal action Seeds of weeds or mono- or dicotyledonous crop plants are placed in wooden fiber pots in sandy clay soil, covered with soil. The test compounds formulated in the form of wettable powders (WP) are then applied as an aqueous suspension with a water application amount of 600 1 / ha with addition of 0, 2% of humectant in different dosages on the surface of the cover soil. After the treatment, the pots are placed in a greenhouse and kept in good growth conditions for the test plants. The visual test on damage in the emergence of the test plants is carried out after a test time of 3 weeks compared to untreated controls (herbicidal action in percentage (%): 100% action = the plants died, 0 % of action = as control plants).
2. Herbicidal action in post-emergence Weed seeds or dicotyledonous crop plants are placed in wooden fiber pots in sandy loamy soil, covered with soil and grown under greenhouse conditions or in good growing conditions. 2-3 weeks after
- - the sowing, the test plants are treated in unifoliate stage. The test compounds formulated as spray powder (WP) are sprayed in different dosages with an application amount of water of 600 1 / ha of water with addition of 0.2% of humectant on the green parts of the plants. After approximately 3 weeks of resting period of the greenhouse test plants under optimal growth conditions, the action of the preparations was visually evaluated compared to the untreated controls (herbicidal action in percentage (%): 100% action) = plants died 0% action = as control plants).
The following compounds show, in the preemergence, with 320 g / ha a. i. against Avena sativa, Lolium multiflorum and Setaria viridis an action of > 80%: Ia-2, Ia-8, Ia-9, Ia-10, Ia-11, Ia-14, Ib-10, Ib-12, Ib-13, Ib-14, Ib-15, Ib-16 , Ib-21, Ib-25, Ib-27, lb-28, Ib-33, Ib-34, Ib-36, Ib-43, Ib-44, Ib-50, Ib-52, Ib-54, Ic -1, Ic-4, Ic-5, Ic-8, Ic-9, Ic-12, Ic-14, Ic-16. The following compounds show in the preemergence with 320 g / ha a. i. against Alopecurus myosuroides, Echinocloa crus-gali, Lolium multiflorum and Setaria viridis an action of > 80%: Ia-18, Ia-20, Ia-21, Ia-24, Ia-25, Ia-26, Ia-27, Ib-55, Ib-56, Ib-57, Ib-59, Ib-60 , Ib-73, Ib-76, Ib-77, Ib-78, Ib-79, Ib-80, Ib-81, Ib-82, Ib-83, Ic-19, Ic-23, Ic-24, Ic -25, Ic-
- -
26, I-e-17, I-e-18 The following compounds show in the postemergence with 320 g / ha a. i. against Avena sativa, Lolium multiflorum and Setaria viridis an action of > 80%: Ia-1, Ia-2, Ia-8, Ia-9, Ia-10, Ia-12, Ia-13, Ia-14, Ia-15, Ia-16, Ib-4, Ib-9 , Ib-10, Ib-11, Ib-12, Ib-14, Ib-15, Ib-16, Ib-17, Ib-18, Ib-19, Ib-21, Ib-22, Ib-24, Ib -25, Ib-26, Ib-27, lb-28, Ib-30, Ib-32, Ib-33, Ib-34, Ib-35, Ib-36, Ib-37, Ib-38, Ib-39 , Ib-40, Ib-42, Ib-43, Ib-44, Ib-45, Ib-46, Ib-47, Ib-50, Ib-51, Ib-52, Ib-53, Ib-54, lc -3, lc-4, Ic-5, lc-7, lc-8, Ic-9, Ic-11, Ic-12, Ic-13, Ic-14, Ic-15, Ic-17, Ic-18 , le-13, le-16. The following compounds show in the postemergence with 320 g / ha a. i. against Lolium -multiflorum, Setaria viridis and Echinocloa crus-gali an action of > 90%: Ia-3, Ia-4, Ia-1, Ib-1, Ib-2, Ib-5, Ib-8, Ib-13, Ib-20, Ib-23, Ib-31, Ic-6 , Ic-16, le-12. The following compounds show in the postemergence with 80 g / ha a. i. against Echinocloa crus-gali, Lolium multiflorum and Setaria viridis an action of > 90%: Ia-18, Ia-19, Ia-22, Ia-24, Ia-25, Ia-26, Ia-27, Ib-56, Ib-57, Ib-59, Ib-62, Ib-63 , Ib-66, Ib-67, Ib-68, Ib-71, Ib-72, Jb-73, Ib-74, Ib-76, Ib-77, Ib-78, Ib-79, Ib-80, Ib -81, Ib-82, Ib-83, Ic-21, Ic-22, Ic-23, Ic-25, Ic-26.
- -
Example B Herbicidal action in post-emergence Weed seeds or mono- or dicotyledonous crop plants are placed in wooden fiber pots or plastic pots in sandy clay soil, covered with soil, and grown in a greenhouse for a period of time. vegetative even outdoors outside the greenhouse under good growth conditions. 2-3 weeks after sowing, the test plants are treated in a one to three leaf stage. The test compounds formulated as spray powder (WP) or liquid (EC) are sprayed in different dosages with a water application amount of 300 1 / ha with addition of humectant (0.2 to 0.3%) on the plants and the surface of the soil. 3 to 4 weeks after the treatment of the test plants, the action of the preparations was evaluated visually, in comparison with the untreated controls (herbicidal action in percentage (%): 100% action = the plants died) , 0% action = as control plants).
In addition, if it is necessary to verify if the crop protectors can improve the tolerance of the plants to test substances in the crop plants, the following possibilities are used for the application of the crop protector: - the seeds of the crops crop plants are disinfected before the
- - plant with the substance of the culture protector (indication of the amount of crop protection in percentage, with respect to the weight of the seeds) - the crop plants are sprayed before the use of the test substances with the protective culture with a certain application amount per hectare (usually 1 day before the use of the test substances) - the culture protector is applied together with the test substance as a tank mixture (indication of the amount of protective of cultivation in g / ha or as a relation with the herbicide). By comparing the action of the test substances on the crop plants that were treated with crop protection and without it, the action of the substance of the culture protector can be evaluated.
Tests in containers with cereals in greenhouse Table
- -
Table
Table
Table
- -
Table
Table
Table
- -
Table
Table
Table
- -
Table
Table
Table
Table
- -
Table
Table
Table
Table
- -
Table
Table
Table
- -
Table
Table
In comparison with the compounds I-6-a-1 and I-6-b-1 known from WO 01/74780 *, the compounds according to the invention show, for example, a clearly better action in the post-emergence process. Example g / ha ALOMY AVEFA LOLMU
I-6-a-l * 200 30 10 30 100 10 0 30
I-a-9 200 9i 100 99 100 9f 100 99
- -
Example g / ha ALOMY AVEFA LOLMU
I-6-l-b * 200 20 20 40 100 0 0 20
I-b-26 200 97 100 100 95 98 70
I-b-24 200 90 95 98 100 80 90 95
Example C Myzus test (spray treatment MYZUPE) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether To obtain a convenient active ingredient preparation, 1 part is mixed by weight of active ingredient with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed, which are infested by all stages of green peach leaf aphid (Myzus persicae), with a preparation of active ingredients of the desired concentration. After the desired time, the action is determined in%.
- -
In this case, 100% means that all aphids on the leaves were killed. 0% means that no aphid leaves died. In this test, the following compounds of the preparation examples show, for example, with 500 g a. i. / has application amount an efficiency of > 90%: Ia-2, Ia-3, Ia-18, Ia-20, Ia-22, Ibl, Ib-14, Ib-15, Ib-16, Ib-17, Ib-18, Ib-21, Ib -22, Ib-25, Ib-51, Ib-52, Ib-55, Jb-56, Ib-57, Ib-58, Jb-59, Jb-60, Ib-61, Ib-63, Ib-67 , Ib-71, Ib-72, Ic-1, Ic-4, Ic-5, Ic-7, Ic-19, Ic-22.
Example D Tetranychus assay; spray treatment / OP-resistant (TETRUR) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether To obtain an appropriate preparation of active substance, 1 part is mixed in Weight of active ingredient with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration. Sprays of bean leaves (Phaseolus vulgaris), which are infested by all stages of Fetranychus, are sprayed
- - urti falls, with an active substance preparation of the desired concentration. After the desired time, the action is determined in%.
In this case, 100% means that all the mites were dead. 0% means no mite died. In this test, the following compounds of the preparation examples show, for example, with 100 g a. i. / has application amount an efficiency of > 90%: Ia-1, Ia-2, Ia-3, Ia-11, Ia-18, Ia-20, Ia-22, Ia-23, Ib-1, Ib-9, Ib-10, Ib-11 , Ib-14, Ib-15, ll-b-17, Ib-18, Ib-19, Ib-21, Ib-23, Ib-25, Ib-26, Ib-29, Ib-30, Ib-31 , Ib-35, Ib-37,
Ib-55, Ib-56, Ib-57, Ib-58, Ib-59, Ib-60, Ib-64, Ib-67, Ib-70, Ib-75, Ib-76, Ib-77, Ib- 78, Ib-79, Ib-80, Ib-83, Ib-42,
I-c-3, I-c-4, I-c-5, I-c-10, I-c-19, I-c-22, I-c-24, I-c-25, I-c-27, I-e-17.
Example E Phaedon test (Phaeco spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether To obtain a convenient active ingredient preparation, 1 part is mixed by weight of active principle with the indicated amounts of solvent and emulsifier and
- - dilute the concentrate with water containing emulsifier to the desired concentration. Discs of leaves of cabbages of China (Brassica pekinensis) are sprayed with a preparation of active principles of the desired concentration and after drying, they are populated with larvae of Phaedon cochleariae. After the desired time, the action is determined in%. In this case, 100% means that all the beetle larvae died. 0% means that no beetle larvae died. In this test, the following compounds of the preparation examples show, for example, with 500 g a. i. / has application amount an efficiency of > 80%: Ia-1, Ia-2, Ia-3, Ia-15, Ia-20, Ia-21, Ia-22, Ib-14, Ib-15, Ib-16, Ib-17, Ib-18 , Ib-19, Ib-21, Ib-22, Ib-55, Ib-61, Ib-67, Ib-71, Ic-1, Ic-4, Ic-5, Ic-19, Ic-22.
Example F Boophilus mieroplus test (BOOPMI injection) Solvent: dimethylsulfoxide To obtain a convenient active ingredient preparation, 1 part by weight of active ingredient is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentration.
- -
The active substance solution is injected into the abdomen (Boophilus microplus), animals are placed in buckets and stored in an air-conditioned environment. After the desired time, the action is determined in%. In this case, 100% means that no tick has laid fertile eggs. In this test, the following compound of the preparation examples shows, for example, 20 μg a. i. / animal an efficacy of > 90%: I-b-10, I-b-55, I-b-70, I-c-10, I-c-22.
Example G Limit 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 In order to obtain an appropriate active ingredient preparation, 1 part by weight of active principle is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and dilute the concentrate with water to the desired concentration. The preparation of active principle is poured into the soil.
In this case, the concentration of the active ingredient in the preparation practically plays no role
- - important, only the amount by weight of active ingredient per unit volume of soil that is indicated in ppm is decisive
(mg / 1). Place the soil in 0.25 1 pots and let them stand at 20 ° C. Immediately after the preparation, 5 pregerminated maize grains of the YIELD GUARD type are placed in a pot.
(registered trademark of Monsanto Comp., United States). After 2 days, the corresponding test insects are placed on the treated soils. After another 7 days, the degree of action of the active ingredient is determined by counting in the emerged corn plants (1 plant = 20% action).
Example H Test of Heliothis virescens - treatment of transgenic plants Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To obtain a convenient active ingredient preparation, 1 part by weight of active ingredient is mixed with the indicated amount of solvent and the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration. Soybean sprouts (Glycine max) of the Roundup Ready variety
(registered trademark of Monsanto Comp., United States) are treated by immersion in the preparation of active principle of the
- - desired concentration and they are populated with the caterpillar of tobacco buds Heliothis virescens, while the leaves are still moist. After the desired time, the extermination of the insects is determined. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (21)
- - - 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 X represents methyl and Y represents methyl or ethyl, X and Y represent ethyl, where A represents hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl optionally substituted in each case with halogen, optionally substituted, saturated or unsaturated cycloalkyl, wherein eventually at least one atom of the ring is replaced by a heteroatom, B represents hydrogen, alkyl or alkoxyalkyl, or A and B represent, together with the carbon atom to which they are attached, an unsubstituted or unsaturated or unsubstituted ring, optionally containing at least one heteroatom, - - A and Q1 represent together optionally substituted alkanediyl or alkeniyl, which may optionally be interrupted by a heteroatom, Q1 and Q2 represent, independently of one another, hydrogen or alkyl, or in which X represents ethyl and Y represents methyl, where A and B, together with the carbon atom to which they are attached, represent an unsubstituted or substituted 4 to 8 membered saturated or unsaturated ring, and Q1 and Q2 represent hydrogen or A and Q1 together represent alean C2-C6-diyl or alken C2 -C6-say it in each case optionally substituted, which may eventually be interrupted by heteroatoms and B and Q2 represent, independently of each other, hydrogen or alkyl, G represents hydrogen (a) or 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 with halogen or cycloalkyl optionally substituted with halogen, alkyl or alkoxy, which may be interrupted by at least one heteroatom, phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl in each case optionally substituted, R 2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl in each case optionally substituted with halogen or optionally substituted cycloalkyl, phenyl or benzyl, R3, R4 and R5 represent, independently of each other, alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio optionally substituted in each case with halogen or phenyl, benzyl, phenoxy or - phenylthio in each case optionally substituted, R6 and R7 represent, independently of each other, hydrogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl optionally substituted in each case with halogen, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached represent a cycle eventually interrupted by oxygen or sulfur.
- 2. Compounds of the formula (I) according to claim 1, characterized in that X represents methyl and Y represents methyl or ethyl or X and Y represent both ethyl, A represents hydrogen or C1-C12 alkyl, C3-C8 alkenyl, alkoxy C? -C? -alkyl? -C8 alkyl, C? -C? Alkyl or thio-C1-C? Alkyl in each case optionally substituted with halogen, C3-C8 cycloalkyl optionally substituted with halogen, C? -C6 alkyl or C6-C6 alkoxy, in which optionally one or two non-directly adjacent ring members are replaced by oxygen and / or sulfur, B represents hydrogen, C1-C12 alkyl or C6-8 alkyl-alkoxy C? -C6 or A, B and the carbon atom to which they are attached represent - saturated C3-C10 cycloalkyl or unsaturated C5-C10 cycloalkyl, in which, optionally, a ring member is replaced by oxygen or sulfur and optionally mono- or di-substituted with C?-C8 alkyl, C?-C8 haloalkyl or alkoxy C? -C8 or A, B and the carbon atom to which they are attached represent C3-C6 cycloalkyl which is substituted with an alkylenediyl group or with an alkylenedioxyl group or with an alkylenedithioyl group optionally substituted with C1-C4 alkyl optionally containing one or two atoms of oxygen and / or sulfur not directly adjacent, which forms with the carbon atom to which another ring of five to eight members is attached or A, B and the carbon atom to which they are attached represent preferably C3-C8 cycloalkyl or C5-C8 cycloalkenyl, in which two substituents represent together with the carbon atoms to which they are attached alloy C2-Cg-diyl, C2-C6 alkenyl diyl or C4-C6 alkadiene-diyl in each case optionally substituted with Ci-Cß alkyl, Ci-Cβ alkoxy or halogen, in that eventually a methylene group is replaced by oxygen or sulfur, A and Q1 together represent C? -C? alkyl, C? -C6 alkoxy, alkyl C? -C6-thio, optionally mono- or di-substituted, in the same or different manner, with halogen, hydroxy, in each case optionally mono- to trisubstituted in the same way or - - different with halogen, C3-C cycloalkyl or C2-C6 alean or diyl or C2-C6 alkenyl substituted with benzyloxy or optionally mono- to trisubstituted phenyl, in the same or different manner, with halogen, C6-C6 alkyl or alkoxy Ci-Cß, which also contains possibly one of the following groups or that is bridged with an alean C? -C2-diyl group or that is interrupted or bridged with an oxygen atom, Q1 and Q2 represent, independently of each other, hydrogen or C? -C4 alkyl, or X represents ethyl and Y represents methyl and a) A, B and the carbon atom to which they are attached - - represent saturated C4-C8 cycloalkyl or unsaturated C5-C8 cycloalkyl, in which, optionally, a ring member is replaced by oxygen or sulfur and optionally mono- or di-substituted with C? -C8 alkyl, C8-C8 haloalkyl or alkoxy Ci-Cg or A, B and the carbon atom to which they are attached represent C3-C6 cycloalkyl which is optionally substituted with an alkylenediyl group, an alkylenedioxyl group or an alkylenedithioyl group optionally substituted with C? -C4 alkyl optionally containing one or two atoms of oxygen and / or sulfur not directly adjacent, which with the carbon atom to which it is attached form another ring of five to eight members or A, B and the carbon atom to which they are attached represent - C3-C8 cycloalkyl or Cs-C8 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent C2-C6-diyl, C2-C6 alkenyl or C4-C6-aldolene alloyl in each case optionally substituted with C?-C6 alkyl, C?-C6 alkoxy or halogen, in which optionally a methylene group is replaced by oxygen or sulfur, Q1 and Q2 represent hydrogen, or b) A and Q1 together represent Ci-Cio alkyl, C-alkoxy -C6, alkyl C? -C6-thio, optionally mono- or disubstituted, in the same or different manner, with halogen, hydroxy, in each - - case optionally mono- to trisubstituted in the same or different manner with halogen, C3-C cycloalkyl or C2-C6-alloyl diyl or C2-C6 alkenyl substituted with benzyloxy or optionally mono- to trisubstituted phenyl, in the same or different way , with halogen, C? -C6 alkyl or C? -C6 alkoxy, which optionally contains one of the following groups or which is bridged with an alean C? -C2-diyl group or which is interrupted or bridged with an oxygen atom, B and Q2 represent, independently of each other, hydrogen or C? -C2 alkyl, G represents hydrogen (a) or one of the groups - - 5 (e) wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, represents C alquilo-C20 alkyl, C2-C20Í alkenyl C alco-C8 alkoxy-C?-C8 alkyl, C 1 -C 8 -thio-C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy-C alquilo-C 8 -alkyl optionally substituted with halogen, or C 3 -C 8 -cycloalkyl optionally substituted with halogen, Ci-Cg alkyl or Ci-Cβ alkoxy, in which optionally one or more non-directly adjacent ring members are replaced by oxygen and / or sulfur, phenyl optionally substituted with halogen, cyano, nitro, C?-C6 alkyl, C?-C6 alkoxy, halogenalkyl C? C6, C? -C6 haloalkoxy, C? -C6 alkylthio or C? -C6 alkyl sulfo-nyl, phenyl-Ci-Ce alkyl optionally substituted with halogen, nitro, cyano, C? -C6 alkyl, alkoxy C? -C6, C1-C6 halogenalkyl or Ci-C? Haloalkoxy, - - 5- or 6-membered heteroaryl optionally substituted by halogen or Ci-Cß alkyl phenoxy-C alquilo alkyl? optionally substituted with halogen or Ci-Ce alkyl or hetaryloxy-Ci-Ce alkyl of 5 or 6 members optionally substituted with halogen, amino or Ci-Ce alkyl, R2 represents C alquilo-C20 alkyl, C2-C2 alkenyl, C alco alkoxy C8- C2-C8 alkyl, poly-C18-C8-alkoxy-C2-C8 alkyl in each case optionally substituted with halogenC3-C8 cycloalkyl optionally substituted with halogen, C6-C6 alkyl or C6-C6 alkoxy or phenyl or benzyl in each case optionally substituted with halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkoxy, C? -C6 halogenalkyl or C? -C6 halogenalkoxy, R3 represents C? -C8 alkyl optionally substituted with halogen or phenyl or benzyl in each case optionally substituted with halogen, Ci-C? alkyl, Ci-C? alkoxy, C? -C4 haloalkyl , halogenalkoxy C? -C, cyano or nitro, R4 and R5 represent, independently of each other, C?-C8 alkyl, C?-C8 alkoxy, C?-C8-amino alkyl, di- (C C-C8 alkyl) amino, C C-C8-thio alkyl, C2-C8-thio alkenyl, C3-C7 cycloalkyl thio in each case optionally substituted with halogen or phenyl, phenoxy or phenylthio in each case optionally substituted by halogen, nitro, cyano, C? -C4 alkoxy, C1-C4 haloalkoxy, alkyl C? -C4-thio, - - C 1 -C 4 halogenalkyl, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl, R 6 and R 7 represent, independently of each other, hydrogen, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C3-C8 alkenyl, C?-C8 alkoxy-C?-C8 alkyl in each case optionally substituted with halogen, phenyl optionally substituted with halogen, C halo-Cg halogenalkyl, C?-C8 alkyl or C?-C8 alkoxy, benzyl optionally substituted with halogen, C? -C8 alkyl, C? -C8 haloalkyl or C? -C8 alkoxy or together represent an alkylene moiety C3-C6 optionally substituted with C?-C4 alkyl, in which optionally a carbon atom is replaced by oxygen or sulfur, R 13 represents hydrogen, C?-C8 alkyl, C?-C8 alkoxy or C 3 -C 8 alkenyl-oxy in each case optionally substituted by halogen, C3-C8 cycloalkyl optionally substituted with halogen, C? -C4 alkyl or C? -C4 alkoxy, wherein optionally a methylene group is replaced by oxygen or sulfur, or phenyl, hetaryl, phenyl-alkyl C 1 -C 4, phenyl-C 1 -C 4 alkoxy or C 1 -C 4 hetarylalkoxy each optionally substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 4 haloalkyl, C 4 -C 4 haloalkoxy, nitro or cyano, R14a represents hydrogen or C? -C8 alkyl or R13 and R14a together represent alloy C4-C6-diyl, - - R15a and R16a are the same or different and represent C? -C6 alkyl? R15a and R16a together represent a C2-C4 alkoxy-diyl residue which is optionally substituted by C?-C6 alkyl, C?-C6 haloalkyl or phenyl optionally substituted by halogen, C?-C6 alkyl, C?-C4 haloalkyl, Ci-alkoxy -Ce, halogenalkoxy C? -C4, nitro or cyano, R17a and R18a represent, independently of each other, hydrogen, C? -C8 alkyl optionally substituted with halogen or phenyl optionally substituted with halogen, C1-Ce alkyl, C13 alkoxy Ce, C?-C 4 halogenalkyl, C?-C 4 halogenalkoxy, nitro or cyano or R 17a and R 18a represent, together with the carbon atom to which they are attached, a carbonyl or C 5 -C 7 cycloalkyl group optionally substituted with halogen, alkyl C? -C4 or C? -C4 alkoxy, in which optionally a methylene group is replaced by oxygen or sulfur, R19a and R20a represent, independently of each other, C1-C10 alkyl, C2-C? Alkenyl, C1 alkoxy -C10, alkyl C? -C? O-amino, C3-C? Alkylamino, di- (C1-C10 alkyl) amino or di- (C3-C? Alkenyl) Not me .
- 3. Compounds of the formula (I) according to claim 1, characterized in that X represents methyl, Y represents methyl or ethyl, - or X and Y represent both ethyl, A represents hydrogen, Ci-Cß alkyl, C?-C 4 alkoxy-C?-C alquilo alkyl in each case optionally mono- to trisubstituted with fluorine or chlorine, or optionally C 3 -C 6 cycloalkyl mono - a disubstituted with C? -C2 alkyl or C? -C2 alkoxy, B represents hydrogen, C? -C4 alkyl or C? -C2 alkoxy C? -C2 alkyl or A, B and the carbon atom to which they are attached they represent saturated or unsaturated Cs-C7 cycloalkyl, in which optionally a ring member is replaced by oxygen or sulfur and which is optionally mono- to disubstituted with Ci-Cß alkyl, trifluoromethyl or alkoxy A, B and the carbon atom to which they are attached represent - C5-C6 cycloalkyl, which is substituted with an alkylenediyl group or alkylenedioxyl or alkylenedithiol optionally substituted with methyl or ethyl which optionally contains one or two oxygen or sulfur atoms not directly adjacent , which with the carbon atom to which it is attached form another ring of five or six members, 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 - - are bonded represent alean C2-C4-diyl, alken C2-C-diyl or butadiendiil in each case optionally substituted with C? -C2 alkyl or C? -C2 alkoxy, A and Q1 together represent C3-C4 alloy-diyl or alken C3-C4-diyl in each case optionally mono- or disubstituted, in the same or different manner, with hydroxy, C? -C2 alkyl or Ci- C2 alkoxy, optionally containing one of the following groups or which may be interrupted or bridged by an oxygen atom, Q1 and Q2 represent, independently of each other, hydrogen or C? -C2 alkyl or X represents ethyl? Y represents methyl and a) A, B and the carbon atom to which they are attached represent saturated or unsaturated Cs-C7 cycloalkyl, wherein optionally a ring member is replaced by oxygen or sulfur and which is optionally mono- to disubstituted with alkyl C? -C6, trifluoromethyl or alkoxy - - C? -C6, with the proviso that then Q3 represents with special preference 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 or alkylenedioxyl group or alkylenedithiol, optionally substituted with methyl or ethyl optionally containing one or two oxygen or sulfur atoms not directly adjacent, which with the carbon atom to which it is attached forms another five or six membered ring, with the proviso that then Q3 represents hydrogen or methyl, 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 represent alean C2-C4-diyl, alken C2-C4- diyl or butadiene-dichloride in each case optionally substituted with C? -C2 alkyl or C? -C2 alkoxy, with the proviso that then Q3 represents hydrogen or methyl, or Q1 and Q2 represent hydrogen or b) A and Q1 together represent C3-C4-diyl or C3-C4-alkenyl diyl in each case optionally mono- or disubstituted, in the same or different manner, with hydroxy, C? -C2 alkyl or C1-C12 alkoxy, which eventually it contains one of the - - following groups or is interrupted or bridged by an oxygen atom, B and Q2 represent independently of each other, hydrogen or methyl, G represents hydrogen (a) or one of the groups ^ < » A "" '(O. -S ° ^ Rl < d,. / (E), wherein E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, R1 represents C?-C8 alkyl, C2-C8 alkenyl, C alco-C4 alkoxy C alquilo-alkyl C 2, C 1 -C 4 alkyl thio-C 1 -C 2 alkyl optionally mono- to trisubstituted with fluorine or chlorine or C 3 -C 6 cycloalkyl optionally mono- to disubstituted with fluorine, chlorine, C 1 -C 2 alkyl or alkoxy C ? -C2, in which eventually one or two ring members not directly adjacent are replaced by oxygen, - - phenyl optionally mono- to disubstituted with fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl or C 2 -C 2 haloalkoxy, R 2 represents Ci-Cg alkyl, alkenyl C2-C8 or C1-C4-alkoxy-C2-C4 alkyl in each case optionally mono- to trisubstituted with fluorine, C3-C6 cycloalkyl optionally monosubstituted with C alquilo-C2 alkyl or C1-C2 alkoxy or phenyl or benzyl in each case optionally mono - a disubstituted with fluorine, chlorine, bromine, cyano, nitro, C? -C4 alkyl, C1-C3 alkoxy, trifluoromethyl or trifluoromethoxy, R3 represents C? -C6 alkyl optionally mono- to trisubstituted with fluorine or phenyl optionally monosubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R 4 represents Ci-Cß alkyl, C?-C6 alkoxy, Ci-Ce-amino alkyl, di- (Ci-Cß alkyl) ) amino, C 1 -C 6 alkyl thio, C 3 -C 4 alkenyl thio, C 3 -C 5 cycloalkyl thio in each case optionally mono- to trisubstituted with fluorine or chlorine or phenyl, phenoxy or phenylthio in each case optionally monosubstituted with fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 alkoxy, C 1 -C 3 halogenalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 halogenalkyl, C 1 -C 3 alkyl or trifluoromethyl, - - R 5 represents C 1 -C 6 alkoxy or C 1 -C 6 alkylthio in each case optionally monosubstituted with chlorine, R 6 represents hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 6 alkoxy, C 3 -C 6 alkenyl, alkoxy Ci-Cd-C 1 -C 4 alkyl, phenyl optionally monosubstituted with fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, benzyl optionally monosubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, trifluoromethyl or C 1 -C 4 alkoxy, R 7 represents C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 1 -C 6 alkoxy C 1 -C 4 alkyl, R 6 and R 7 together represent a C 4 -C 4 alkylene radical optionally substituted with methyl or ethyl in which optionally a methylene group is replaced by oxygen or sulfur, R13 represents hydrogen, C?-C8 alkyl, C?-C8 alkoxy, C3-C6 alkenyl-oxy in each case optionally mono- to trisubstituted with fluorine or chlorine, C3-C8 cycloalkyl optionally substituted by halogen, C? -C4 alkyl or C? -C4 alkoxy, wherein optionally a methylene group is replaced by oxygen no or sulfur, or phenyl, pyridyl, pyrimidyl, thiazolyl, phenyl-C 1 -C 2 alkyl or pyridyl-C 1 -C 2 alkoxy in each case optionally substituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 alkoxy C, halogenalkyl C? -C2, halogenalkoxy C? -C2, nitro or cyano, R17a and R18a represent, independently of each other, - hydrogen, C 1 -C 4 alkyl optionally mono- to trisubstituted with fluorine or chlorine or optionally mono- to phenyl disubstituted with fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkyl, halogenalkoxy C? -C2, nitro or cyano or R17a and R18a together with the carbon atom to which a C5-C6 carbonyl or cycloalkyl group are optionally mono- to disubstituted with fluorine, chlorine, C1-C3 alkyl or C4-C4 alkoxy are attached.
- 4. Compounds of the formula (I) according to claim 1, characterized in that X represents methyl, Y represents methyl or ethyl or X and Y represent both ethyl, A represents hydrogen, C1-C4 alkyl or C6-C2 alkoxy C?-C 2 alkyl in each case optionally mono- to trisubstituted with fluorine, or represents cyclopropyl, cyclopentyl or cyclohexyl, B represents hydrogen, methyl or ethyl or A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 cycloalkyl , in which eventually a ring member is replaced by oxygen and which is optionally monosubstituted with methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, - - propoxy or butoxy, A, B and the carbon atom to which they are attached represent C6 cycloalkyl, which is substituted with an alkylenedioxyl group containing two oxygen atoms not directly adjacent to it, with the carbon atom to which it is attached, it forms another ring of five or six members, 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 represent alloy C2-C4-diyl or C2-C4 alkenyl diyl or butadiene-diol, A and Q1 together represent C3-C4-allyl or C3-C-diyl allyl optionally mono- or disubstituted, in the same or different manner, with hydroxy, methyl or methoxy that eventually contain one of the following groups or that may be interrupted or bridged by an oxygen atom, Q1 and Q2 represent, independently of each other, hydrogen or methyl or X represents ethyl - and Y represents methyl, and a) A, B and the carbon atom to which they are attached represent saturated C5-C6 cycloalkyl in which, optionally, one ring member is replaced by oxygen or sulfur and which is optionally monosubstituted with methyl, ethyl , propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy, A, B and the carbon atom to which they are attached represent cycloalkyl C? , which is substituted with an alkylenedioxyl group containing two oxygen atoms not directly adjacent, which, with the carbon atom to which it is attached, forms another five or six member ring, A, B and the carbon atom to which they are attached. linked represent C5-C6 cycloalkyl or C5-C6 cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent C2-C4 allele-di2 or C2-C-diyl or butadye-diyl alken, Q1 and Q2 represent hydrogen or b) A and Q1 together represent alean C3-C-diyl or C3-C4 alkenyl diyl optionally mono- or disubstituted with hydroxy, methyl or methoxy - - which eventually contain one of the following groups or that is interrupted or bridged by an oxygen atom, B and Q2 represent, independently of each other, hydrogen or methyl, G represents hydrogen (a) or one of the groups wherein E represents an ammonium ion, L represents oxygen or sulfur, and M represents oxygen or sulfur, R 1 represents C 1 -C 2 alkyl, C 2 -C 6 alkenyl, C 1 -C 2 alkoxy C x alkyl, C 1 -C 2 alkyl thio- Ci alkyl or C3-C6 cyclopropyl optionally monosubstituted with fluorine, chlorine, methyl or methoxy or C1-C4 alkyl monosubstituted with chlorine, phenyl optionally monosubstituted with fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R2 represents alkyl C? ~ Cg, C2-C6 alkenyl or C? -C4 alkoxy-C2-C3 alkyl in each case optionally mono- - - trisubstituted with fluorine, phenyl or benzyl, R3 represents C? -C6 alkyl, R4 represents C? -C4 alkyl, C1-C4 alkoxy, C? -C4 alkyl amino, di- (C1-C4 alkyl) amino, alkyl C? -C4-thio, C-C4-thio alkenyl, C3-C6 cycloalkyl-thio in each case optionally mono- to trisubstituted with fluorine or chlorine or represents phenyl, phenoxy or phenylthio in each case optionally monosubstituted with fluorine, chlorine, bromine , nitro, cyano, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methyl or trifluoromethyl, R 5 represents C 1 -C 4 alkoxy or C 1 -C 4 alkyl thio optionally monosubstituted with chlorine, R 13 represents C 1 -C alkyl, C 1 -C 4 alkoxy or alkenyl C3-C4-oxy in each case optionally mono- to trisubstituted with fluorine or chlorine or represents benzyl or pyridyl in each case optionally substituted with fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R17a and R18a represent, independently each other, C1-C4 alkyl optionally mono- to trisubstituted with fluorine or chlorine or phenyl eve Currently mono- to di-substituted with fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano or R17a and R18a represent, together with the carbon atom to which they are attached, C5-C6 cycloalkyl optionally mono- or disubstituted with methyl or ethyl. - - 5. Compounds of the formula (I) according to claim 1, characterized in that X represents methyl, Y represents methyl or ethyl, or X and Y represent both ethyl, A represents methyl, B represents hydrogen or methyl or A, B and the atom carbon to which they are attached, represent saturated C5-C6 cycloalkyl in which eventually one ring member is replaced by oxygen and which is eventually monosubstituted with methyl, A and Q1 together represent C3-C5-diyl or C3-Cs alken- say it in each case possibly monosubstituted with methyl, which eventually contain one of the following groups Q1 and Q2 represent, independently of one another, hydrogen, or X represents ethyl and Y represents methyl and - - a) A, B and the carbon atom to which they are attached represent saturated C5-C6 cycloalkyl, in which eventually a ring member is replaced by oxygen, Q1 and Q2 represent hydrogen or b) A and Q1 represent together alloy C3 -C5-diyl or alken C3-Cs-diyl in each case optionally monosubstituted with methyl, which optionally contain one of the following groups or that is interrupted or bridged by an oxygen atom, B and Q2 represent, independently of each other, hydrogen, G represents hydrogen (a) or one of the groups wherein L represents oxygen and M represents oxygen, R1 represents Ci-Cd alkyl, C? -C2 alkoxy-C1-C2 alkyl, or C? -C4 alkyl monosubstituted with chlorine, - - R represents C? -C8 alkyl, R4 represents C? -C alkoxy optionally monosubstituted with chlorine, R5 represents C? -C4 alkoxy optionally monosubstituted with chlorine, R17a and R18a represent methyl. 6. Process for preparing compounds of the formula (I) according to claim 1, characterized in that it is to obtain (A) compounds of the formula (I-a) wherein A, B, Q1, Q2, X and Y have the meanings indicated above, ketocarboxylic acid esters of the formula (II) are intramolecularly cyclized. in which - - A, B, Q1, Q2, X and Y have the meanings indicated above, and R8 represents alkyl optionally in the presence of a diluent and in the presence of a base, (B) compounds of the formula (1-b) above, wherein A, B, Q1, Q2, R1, X and Y have the meanings indicated above, compounds of the formula (Ia) indicated above are reacted, wherein A, B, Q1, Q2, X and Y have the meanings indicated above, (a) with acid halides of the formula (III) wherein R1 has the meaning indicated above and Hal represents halogen or (ß) with carboxylic acid anhydrides of the formula (IV) Rl-CO-O-CO-R1 (ÍV) wherein R1 has the meaning indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor; (C) compounds of the formula (I-c) above, in which - - A, B, Q1, Q2, R2, M, X and Y have the meanings indicated above and L represents oxygen, compounds of the above-mentioned formula (I-a) are reacted, wherein A, B, Q1, Q2, X and Y have the meanings indicated above, in each case with esters of chloroformic acid or thioesters of chloroformic acid of the formula (V) R2-M-CO-C1 (V) in which R2 and M have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor; (D) compounds of the formula (Ic) indicated above, in which A, B, Q1, Q2, R2, M, X and Y have the meanings indicated above and L represents sulfur, compounds of the formula (Ia) are reacted ), in which A, B, D, Q1, Q2, X and Y have the meanings indicated above, in each case with esters of chloromonothioformic acid or esters of chlorodithioformic acid of the formula (VI) CI ^^ MR Y (VI ) s where M and R2 have the meanings indicated above, possibly in the presence of a diluent and optionally in - - presence of an acid acceptor; (E) compounds of the formula (Id) above, in which A, B, Q1, Q2, R3, X and Y have the meanings indicated above, compounds of the formula (Ia) indicated above are reacted in the that A, B, D, Q1, Q2, X and Y have the meanings indicated above, in each case with sulphonic acid chlorides of the formula (VII) R3-so2-c? (vp) wherein R3 has the meaning indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor, (F) compounds of the formula (Ie) above, wherein A, B, L, Q1, Q2, R4, R5, X and Y have the meanings indicated above, compounds of the formula (Ia) indicated above are reacted, in which A, B, Q1, Q2, X and Y have the meanings indicated above, in each case case with phosphorus compounds of the formula (VIII) R4 Hal P UN s (HIV) L Rs wherein L, R4 and R5 have the meanings indicated above and Hal represents halogen, - - optionally in the presence of a diluent and optionally in the presence of an acid acceptor, (G) compounds of the formula (If) mentioned above, in which A, B, E, Q1, Q2, X and Y have the meanings as indicated above, compounds of the formula (la) are reacted, wherein A, B, Q1, Q2, X and Y have the meanings indicated above, in each case with metal compounds or amines of the formulas (IX) or ( X) R10 R11 Me (OR10) t (IX), 2 (X) wherein Me represents a mono- or divalent metal, t represents the number 1 or 2 and R10, R11, R12 represent, independently of each other, hydrogen or alkyl, optionally in the presence of a diluent, (H) compounds of the formula (Ig) indicated above, in which A, B, L, Q1, Q2, R6, R7, X and Y have the meanings indicated above, compounds of the formula (Ia) indicated above are reacted, in which A , B, Q1, Q2, X and Y have the meanings indicated above, in each case (a) with isocyanates or isothiocyanates of the formula (XI) R6-N = C = L (XI) in which - - R6 and L have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of a catalyst or (ß) with carbamic acid chlorides or thiocarbamic acid chlorides of the formula (XII) wherein L, R6 and R7 have the meanings indicated above, optionally in the presence of a diluent and optionally in the presence of an acid acceptor. 7. Agent characterized in that it has an effective content of a combination of active ingredients comprising as components a ') at least one compound of the formula (I), wherein A, B, G, Q1, Q2, X and Y have the meanings indicated above and (£ > ') at least one compound that improves the tolerance of the crop plants of the following group of compounds: 4-dichloroacetyl-l-oxa-4-aza-spiro [4, 5] - decane (AD-67, MON4660), l-dichloroacetyl-hexahydro-3, 3, 8a-trimethylpyrrolo [1,2-a] -pyrimidin-6 (2H) -one (dicyclonone, BAS-145138), 4-dichloroacetyl- 3, 4-dihydro-3-methyl-2H-l, 4-benzoxazine (benoxacor), (ester 1- - - methylhexyl) of 5-chloro-quinoline-8-oxy-acetic acid (cloquintocet-mexyl - also other related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP -A-492366), 3- (2-chloro-benzyl) -l- (l-methyl-l-phenyl-ethyl) -urea (cumylurone), a- (cyanomethoximino) -phenylacetonitrile (cyometrinyl), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4- (2,4-dichloro-phenoxy) -butyric acid (2,4-DB), 1- (1-methyl-1-methyl) phenyl-ethyl) -3- (4-methylphenyl) -urea (daimurone, dimrona), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl ester of the piperidin-1-thiocarboxylic acid (dimepiperate), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) -acetamide (DKA-24), 2 , 2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), 4,6-dichloro-2-phenyl-pyrimidine (phenchlorim), 1- (2,4-dichloro-phenyl) ethyl ester -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid (fenchlorazole-ethyl-comp. Also related compounds in EP-A-174562 and EP-A-346620), 2-methyl ester Chloro-4-trifluoromethyl-thiazole-5-carboxylic acid (flurazole), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5- ( 2-furanyl) -2, 2-dimethyl-oxazolidine (furilazole, MON-13900), 4,5-dihydro-5,5-diphenium ethyl l-3-isoxazolecarboxylate (isoxadifen-ethyl-comp. also related compounds in WO-A 95/07897), 1- (ethoxycarbonyl) -ethyl-3,6-dichloro-2-methoxybenzoate (lactidychlor), (4-chloro-o-tolyloxy) -acetic acid (MCPA) , 2- (4-chloro-o-tolyloxy) -propionic acid - - (mecoprop), diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl-comp. also related compounds in WO- A-91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro [4, 5] decan-4-carbodithioate (MG- 838), 1,8-naphthalene anhydride, a- (1,3-dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinyl), 2,2-dichloro-N- (1,3-dioxolan-2-) il-methyl) -N (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine ( R-29148), 4- (4-chloro-o-tolyl) -butyric acid, 4- (4-chloro-phenoxy) butyric acid, diphenylmethoxyacetic acid, diphenylmethoxyacetic acid methyl ester, diphenylmethoxyacetic acid ethyl ester, ester 1- (2-chloro-phenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester, l- (2,4-dichloro-phenyl) -5-methyl-1H-pyrazole-3-ethyl ester -carboxylic, ethyl ester of l 1- (2,4-dichloro-phenyl) -5-isopropyl-1H-pyrazole-3-carboxylic acid, ethyl ester 1- (2,4-dichloro-phenyl) -5- (1,1-dimethyl-ethyl) ) -lH-pyrazole-3-carboxylic acid, l- (2,4-dichloro-phenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester (comp. also related compounds in EP-A-269806 and EP-A-333131), 5- (2, -dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester, 5-phenyl-2-ethyl-2-ethyl ester isoxazoline-3-carboxylic acid 5- (4-fluoro-phenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (also including related compounds in - - WO-A-91/08202), (1, 3-dimethyl-but-l-yl) -ester of 5-chloro-quinolin-8-oxy-acetic acid4-allyloxy-butyl ester of 5-chloro-quinolin-8-oxy-acetic acid, l-allyloxy-prop-2-yl ester of 5-chloro-quinolin-8-oxy-acetic acid, methyl ester of acid -chloro-quinoxaline-8-oxy-acetic acid, 5-chloro-quinoline-8-oxy-acetic acid ethyl ester, 5-chloro-quinoxalin-8-oxy-acetic acid ester ester, 2-oxoprop-1-ester 5-chloro-quinoline-8-oxy-acetic acid, 5-chloro-quinoline-8-oxy-malonic acid diethyl ester, 5-chloro-quinoxalin-8-oxy-malonic acid diallyl ester, diethyl ester of 5-Chloro-quinoline-8-oxy-malonic acid (also including related compounds in EP-A-582198), 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. -A-613618), 4-chloro-phenoxy-acetic acid, 3,3 '-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulfonyl-benzene, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methyl-urea (aka N- (2-methoxy-benzoyl) -4- [(methylamino-carbonyl) -amino] -benzenesulfonamide), 1- [4- (N-2 -methoxy-benzoylsulfamoyl) -phenyl] -3,3-dimethyl-urea, 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) -phenyl] -3-methyl-urea, 1- [4- (N-naphthylsulfamoyl ) -phenyl] -3,3-dimethyl-urea, N- (2-methoxy-5-methyl-1-benzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds defined by means of the general formulas of the general formula (lia) - - or of the general formula (Ilb) or of the formula (IIc wherein m represents a number 0, 1, 2, 3, 4 or 5, A1 represents one of the divalent heterocyclic groups schematized below n represents a number 0, 1, 2, 3, 4 or 5, represents alkanediyl optionally substituted with C 1 -C 4 alkyl and / or C 1 -C 4 alkoxycarbonyl and / or C 1 -C 4 alkynyloxycarbonyl with 1 or 2 carbon atoms, R? represents hydroxy, mercapto, amino, Ci-Ce alkoxy, alkyl - - Ci-Cβ-thio, C C-C6-amino alkyl or di (C ?C4) alkyl-amino, R15 represents hydroxy, mercapto, amino, C?-C7 alkoxy, C?-C6 alkenyl-oxy, alkenyl C? -C 6 -oxi-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, Ci-Cd-amino alkyl or di- (C 1 -C 4 alkyl) -amino, R 16 represents C 1 -C 4 alkyl optionally substituted with fluorine, chlorine and / or bromine, R 17 represents hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted with fluorine, chlorine and / or bromine, C 1 -C 4 alkoxy C 1 -C 4 alkyl, dioxolanil -C 4 alkyl, furyl, furyl C 1 -C 4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted with fluorine, chlorine and / or bromine or C 1 -C 4 alkyl, R 18 represents hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted with fluorine, chlorine and / or bromine, C 1 -C 4 alkoxy C 1 -C 4 alkyl, dioxolanyl C 1 -C 4 alkyl , furyl, furyl-C1-C4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted by fluorine, chlorine and / or bromine or C? -C4 alkyl, R17 and R18 also together represent C3-C6-diyl or oxalkane C2-C5-diyl in each case optionally substituted with C1-C4 alkyl, phenyl, furyl, a benzene ring condesized or with two substituents which, together with the C atom to which they are attached, form a carbocycle of 5 or 6 members , R19 represents hydrogen, cyano, halogen, or C1-C4 alkyl, - - C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, R20 represents hydrogen, C? -C6 alkyl, C3-C6 cycloalkyl or tri- (C? -C4 alkyl) -silyl in each case optionally substituted with hydroxy, cyano, halogen or C1-C4 alkoxy, R 21 represents hydrogen, cyano, halogen, or C?-C4 alkyl, C3-C6 cycloalkyl or phenyl in each case optionally substituted with fluorine, chlorine and / or bromine, X represents nitro, cyano, halogen, C1-C4 alkyl, halogenalkyl C? -C4, C1-C4 alkoxy or C1-C4 haloalkoxy, X represents hydrogen, cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 1 -C 4 alkoxy or C 1 -C 4 halogenkoxy, X represents hydrogen, cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy, and / or the following compounds defined by general formulas of the general formula (lid) or of the general formula (l ie) - - in which represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R 22 represents hydrogen or C? -C4 alkyl, R 23 represents hydrogen or C alquilo-C 4 alkyl, R 2 represents hydrogen, C?-C6 alkyl, C?-C6 alkoxy, alkyl C? -C6-thio, alkyl C? -C6-amino or di- (C? -C4 alkyl) -amino in each case optionally substituted with cyano, halogen or C? -C4 alkoxy, or C3-C6 cycloalkyl, C3 cycloalkyl -C6-oxy, C3-C6 cycloalkyl thio or C3-C6 cycloalkyl amino in each case optionally substituted with cyano, halogen or C? -C4 alkyl, R represents hydrogen, Ci-C? Alkyl optionally substituted with cyano, hydroxy, halogen or C 1 -C 4 alkoxy, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl optionally substituted with cyano or halogen, or C 3 -C 6 cycloalkyl optionally substituted with cyano, halogen or C 1 -C 4 alkyl, R 26 represents hydrogen, alkyl C? -C6 eventually - - substituted with cyano, hydroxy, halogen or C1-C4 alkoxy, C3-C6 alkenyl or C3-C6 alkynyl in each case optionally substituted with cyano or halogen, C3-C6 cycloalkyl optionally substituted with cyano, halogen or C1-C4 alkyl, or phenyl optionally substituted with nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy, or together with R 25 represents C 2 -C 6 -alkanyl or C 2 -C 5 -alkyl alkylaryl- diyl each case optionally substituted with C 1 -C 4 alkyl, X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C halogenalkoxy C4, and X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy. Agent according to claim 7, characterized in that the compound that improves tolerance in crop plants is selected from the following group of compounds: cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenchlorim, cumilurone, dimrona or the compounds - - Y 9. Agent according to any of claims 7 or 8, characterized in that the compound that improves tolerance in crop plants is cloquintocetmexyl. 10. Agent according to any of claims 7 or 8, characterized in that the compound that improves tolerance in crop plants is mefenpyr-diethyl. 11. Use of compounds of the formula (I) according to claim 1 for preparing agents for the control of harmful parasites and / or herbicides. 12. Pesticides and / or herbicides, characterized in that they have a content of at least one compound of the formula (I) according to claim 1. 13. Process for controlling animal parasites and / or - undesired plant growth, characterized in that the compounds of the formula (I) are allowed to act in accordance with claim 1 on parasites and / or their habitat. 14. Use of compounds of the formula (I) according to claim 1 for combating animal parasites and / or unwanted plant growth. 15. Process for preparing pesticides and / or herbicides, characterized in that compounds of the formula (I) are mixed according to claim 1 with extenders and / or surfactants. 16. Process for combating the growth of unwanted plants, characterized in that an agent according to claim 7 is allowed to act on the plants or their habitat. 17. Use of an agent according to claim 7 to combat unwanted plant growth. 18. Process for combating the growth of unwanted plants, characterized in that compounds of the formula (I) according to claim 1 and the tolerance-improving compound in culture plants according to claim 7 are allowed to act separately. temporarily close sequence on the plants or their habitat. 19. Compounds of the formula (II) - - characterized in that A, B, Q1, Q2, X, Y and R8 have the meanings indicated above. 20. Compounds of the formula (XIII) characterized because X, Y, A, B, Q1 and Q2 have the meaning indicated above. 21. Compounds of the formula (XIV) characterized because A, B, Q1, Q2, X and Y have the meaning indicated above and R8 and R8 'represent alkyl and when using the compound of the formula (XVI), R8 represents hydrogen.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE102006000971.1 | 2006-01-07 |
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MX2008008733A true MX2008008733A (en) | 2008-09-26 |
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