MXPA06015186A - 3'-alkoxy spirocyclic tetramic and tetronic acids - Google Patents
3'-alkoxy spirocyclic tetramic and tetronic acidsInfo
- Publication number
- MXPA06015186A MXPA06015186A MXPA/A/2006/015186A MXPA06015186A MXPA06015186A MX PA06015186 A MXPA06015186 A MX PA06015186A MX PA06015186 A MXPA06015186 A MX PA06015186A MX PA06015186 A MXPA06015186 A MX PA06015186A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- methyl
- chlorine
- alkoxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 12
- 229920002359 Tetronic® Polymers 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 230000002363 herbicidal Effects 0.000 claims abstract description 9
- 239000004009 herbicide Substances 0.000 claims abstract description 9
- 239000000575 pesticide Substances 0.000 claims abstract description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 998
- 239000000460 chlorine Substances 0.000 claims description 383
- 229910052801 chlorine Inorganic materials 0.000 claims description 352
- 239000001257 hydrogen Substances 0.000 claims description 346
- 229910052739 hydrogen Inorganic materials 0.000 claims description 346
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 341
- 125000000217 alkyl group Chemical group 0.000 claims description 340
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 339
- 125000003545 alkoxy group Chemical group 0.000 claims description 258
- 150000002431 hydrogen Chemical class 0.000 claims description 237
- 239000011737 fluorine Substances 0.000 claims description 222
- 229910052731 fluorine Inorganic materials 0.000 claims description 222
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 213
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 204
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 204
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 185
- 229910052736 halogen Inorganic materials 0.000 claims description 167
- 150000002367 halogens Chemical class 0.000 claims description 167
- 229910052799 carbon Inorganic materials 0.000 claims description 156
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 155
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 142
- -1 alkylene radical Chemical class 0.000 claims description 141
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 140
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 137
- 125000003342 alkenyl group Chemical group 0.000 claims description 127
- 229910052760 oxygen Inorganic materials 0.000 claims description 120
- 239000001301 oxygen Substances 0.000 claims description 120
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 119
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 119
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 112
- 125000001188 haloalkyl group Chemical group 0.000 claims description 109
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 107
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 105
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 95
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 91
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 62
- 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 61
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 239000011593 sulfur Substances 0.000 claims description 56
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 55
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 52
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 51
- 125000004414 alkyl thio group Chemical group 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 125000001544 thienyl group Chemical group 0.000 claims description 34
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 125000002541 furyl group Chemical group 0.000 claims description 32
- 125000004076 pyridyl group Chemical group 0.000 claims description 32
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 20
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004429 atoms Chemical group 0.000 claims description 19
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 18
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
- 125000005842 heteroatoms Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 244000038559 crop plants Species 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 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 7
- 238000000034 method Methods 0.000 claims description 7
- 125000005108 alkenylthio group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- 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 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- MWKVXOJATACCCH-UHFFFAOYSA-N ethyl 5,5-diphenyl-4H-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 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 4
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 claims description 4
- 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
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002794 2,4-DB Substances 0.000 claims description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N Chloroformic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 4
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 230000000855 fungicidal Effects 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 4
- ICJSJAJWTWPSBD-UHFFFAOYSA-M 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)[O-])=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-M 0.000 claims description 3
- 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 3
- 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 3
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4H-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UKSLKNUCVPZQCQ-GZTJUZNOSA-N (E)-1-(4-chlorophenyl)-N-(1,3-dioxolan-2-ylmethoxy)-2,2,2-trifluoroethanimine Chemical compound C=1C=C(Cl)C=CC=1/C(C(F)(F)F)=N\OCC1OCCO1 UKSLKNUCVPZQCQ-GZTJUZNOSA-N 0.000 claims description 2
- PYKLUAIDKVVEOS-JLHYYAGUSA-N (Z)-N-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(/C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-JLHYYAGUSA-N 0.000 claims description 2
- VXJKYWLPNZBSMY-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(naphthalen-1-ylsulfamoyl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC=C12 VXJKYWLPNZBSMY-UHFFFAOYSA-N 0.000 claims description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 claims description 2
- OISQRMLHYOLTJL-UHFFFAOYSA-N 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC1OCCO1 OISQRMLHYOLTJL-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
- 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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
- 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
- SSMLSVTZGLPNBL-UHFFFAOYSA-N C(C)(=O)OCCOC=1C=CC(=C2C=CC=NC=12)Cl Chemical compound C(C)(=O)OCCOC=1C=CC(=C2C=CC=NC=12)Cl SSMLSVTZGLPNBL-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
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N Mecoprop Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 2
- CMCJQHLLWDPWPK-UHFFFAOYSA-N N-[4-(cyclopropylcarbamoyl)phenyl]sulfonyl-2-methoxy-5-methylbenzamide Chemical compound COC1=CC=C(C)C=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 CMCJQHLLWDPWPK-UHFFFAOYSA-N 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 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
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical compound SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 2
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic S-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 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
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 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
- YNZGZAJXHXGDBF-UHFFFAOYSA-N ethyl 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1C1=CC=CC=C1 YNZGZAJXHXGDBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- DLCGDGOEOISSHF-UHFFFAOYSA-N methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate Chemical compound C=1C=CC=C(Cl)C=1N1N=C(C(=O)OC)C=C1C1=CC=CC=C1 DLCGDGOEOISSHF-UHFFFAOYSA-N 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
- 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
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 2
- HFGGXBQZQRVOKM-UHFFFAOYSA-M piperidine-1-carbothioate Chemical compound [O-]C(=S)N1CCCCC1 HFGGXBQZQRVOKM-UHFFFAOYSA-M 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical compound 0.000 claims description 2
- 150000007970 thio esters Chemical class 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 150000001804 chlorine Chemical compound 0.000 claims 9
- 150000002221 fluorine Chemical compound 0.000 claims 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 125000003277 amino group Chemical compound 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical compound 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical compound 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 claims 1
- YCSCQSNFOLNMAV-UHFFFAOYSA-M 5-ethyl-1H-1,2,4-triazole-3-carboxylate Chemical compound CCC1=NC(C([O-])=O)=NN1 YCSCQSNFOLNMAV-UHFFFAOYSA-M 0.000 claims 1
- QKNUWLIMRLCBIJ-UHFFFAOYSA-M ClC1=C(CC2CC(N(O2)CC)C(=O)[O-])C=CC(=C1)Cl Chemical compound ClC1=C(CC2CC(N(O2)CC)C(=O)[O-])C=CC(=C1)Cl QKNUWLIMRLCBIJ-UHFFFAOYSA-M 0.000 claims 1
- 125000002947 alkylene group Chemical compound 0.000 claims 1
- SQFPMCDRPGJOQH-UHFFFAOYSA-N ethyl 5-(4-fluorophenyl)-5-phenyl-4H-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC(F)=CC=1)C1=CC=CC=C1 SQFPMCDRPGJOQH-UHFFFAOYSA-N 0.000 claims 1
- 150000002926 oxygen Chemical compound 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 150000003463 sulfur Chemical compound 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 230000003641 microbiacidal Effects 0.000 abstract description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical group CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- UJTMLNARSPORHR-UHFFFAOYSA-N OC2H5 Chemical group C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 6
- CPPKAGUPTKIMNP-UHFFFAOYSA-N Cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 230000000895 acaricidal Effects 0.000 description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 230000000749 insecticidal Effects 0.000 description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 4
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 239000002585 base Substances 0.000 description 2
- QRVPHJIVUWTJSU-UHFFFAOYSA-N but-1-en-2-ylazanide Chemical compound [CH2+]CC([NH-])=C QRVPHJIVUWTJSU-UHFFFAOYSA-N 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 229940075522 Antidotes Drugs 0.000 description 1
- 229960005069 Calcium Drugs 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007842 Glycine max Species 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 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 description 1
- VBYIVPZYCNKFFD-UHFFFAOYSA-N N-fluorohydroxylamine Chemical compound ONF VBYIVPZYCNKFFD-UHFFFAOYSA-N 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 230000002605 anti-dotal Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005824 corn Nutrition 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- XORSBWXSVBDCCX-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1N=C(C(=O)OCC)C=C1C1=CC=CC=C1 XORSBWXSVBDCCX-UHFFFAOYSA-N 0.000 description 1
- XQTFGOSTLPHBRA-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-propan-2-ylpyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C(C)C)N1C1=CC=C(Cl)C=C1Cl XQTFGOSTLPHBRA-UHFFFAOYSA-N 0.000 description 1
- MHIKKABFNRIARW-UHFFFAOYSA-N fluoro cyanate Chemical compound FOC#N MHIKKABFNRIARW-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The invention relates to novel 3'-alkoxy spirocyclic tetramic and tetronicacids of formula (I), wherein A, B, D, Q1, Q2, G, W, X, Y and Z are as defined in the description, to several methods and intermediate products for the production and the use thereof in the form of pesticides and/or herbicides and/or microbicides, to selective herbicide agents, 3'-alkoxy spirocyclic tetramic and tetronicacids and to at least one compound which improves cultivated plants compatibility.
Description
TETRAMIC AND TETRONIC ACIDS 3 '-ALCOXI ESPIROCICLICOS
FIELD OF THE INVENTION The present invention relates to new 3'-alkoxy substituted ketoenols, spirocyclics, to various processes for their preparation and to their use as pesticides, microbicides and / or herbicides. The object of the invention is also constituted by herbicidal agents, which contain the 3'-substituted alkoxy ketoenols, spirocyclics, on the one hand, and a better compound of compatibility with the crop plants, on the other hand. BACKGROUND OF THE INVENTION Derivatives of 1-H-arylpyrrolidinedione with herbicidal, insecticidal or acaricidal activity are known: EP-A-456 063, EP-A-521 334, EP-A-613 884, EP-A-613 885, WO 95/01 358,
WO 98/06 721, WO 98/25 928, WO 99/16 748, WO 99/24 437 or WO
01/17 972. In addition, derivatives of the 1-H-arylpyrrolidine-dione substituted by alkoxy, spirocyclics are known: EP-A-596 298, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 99/43 649, WO 99/48 869, WO 99/55 673, WO 01/23 354, WO 01/74 770, WO 01/17 972, WO 03/013 249, WO 2004/02 4688, WO 2004/065 366, WO 2004/08 0962, WO 2004 / 00 7448, WO 2004/111042, DE-A-1035 1646, DE-A-1035 4628, DE-A-
REF: 178419
1035 4629, DE-A-1035 1647. It is known that certain 3-dihydrofuran-2-one derivatives have herbicidal, insecticidal or acaricidal properties: EP-A-528 156, EP-A-647 637, WO 95 / 26 954, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 98/06 721 , WO 99/16 748, WO 98/25 928, WO 99/43 649, WO 99/48 869, WO 99/55 673, WO 01/23354, WO 01/74 770, WO 01/17 972, WO 2004 / 024 688, WO 2004/080 962. However, the herbicidal and / or acaricidal and / or insecticidal activity and / or the spectrum of activity and / or the compatibility with the plants of the known compounds are not always sufficient, especially against to the crop plants. DETAILED DESCRIPTION OF THE INVENTION New compounds of the formula (I) have now been found
which means hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or
cyano, X means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, haloalkyl, haloalkoxy or cyano, and in the 4-position means hydrogen, halogen, alkoxy, cyano, haloalkyl or haloalkoxy, Z means hydrogen. W also means hydrogen, halogen or alkyl, X also means halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano, and in the 4-position also means substituted phenyl or hetaryl, optionally Z means, , hydrogen. W also means hydrogen, halogen or alkyl, X also means halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, and also in the 5-position means substituted phenyl or hetaryl, if appropriate, Z in the 4-position means , likewise, hydrogen, alkyl or halogen. W further denotes hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, cyano or trifluoromethyl,
X also means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, haloalkyl, halogenoalkoxy or cyano,
in the 4-position means, furthermore, alkyl, means, furthermore, hydrogen. means, in addition, hydrogen, halogen, alkyl or alkoxy, means, furthermore, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano, in the 4-position further means hydrogen, halogen, alkyl, haloalkyl or haloalkoxy, in the 3-position or 5 also means halogen, alkyl, haloalkyl, cyano, alkoxy or halogenoalkoxy. means an alkanediyl group, optionally substituted or optionally substituted cycloalkyl and / or optionally interrupted by a heteroatom, means hydrogen or alkyl, alkenyl, alkoxy, alkoxy-alkoxy, phenyl, hetaryl respectively substituted, if appropriate, or means substituted cycloalkyl, optionally and / or interrupted if appropriate by heteroatoms and / or by C = 0, means NH or oxygen, means hydrogen, means alkyl, alkoxy, alkoxyalkyl or substituted alkylthioalkyl respectively, optionally, means cycloalkyl If appropriate, a substituted methylene group by heteroatoms or, if appropriate, substituted phenyl, hetaryl, phenylalkyl or hetarylalkyl, if any, is substituted.
Q2 means hydrogen or alkyl, Q! and Q2 signify, together with the carbon, with which they are bonded, a ring with 3 to 6 carbon atoms, optionally substituted, which may be interrupted, if appropriate, by a heteroatom, G means hydrogen (a) or one of the groups
(and),
wherein E means a metal ion or an ammonium ion, L means oxygen or sulfur, M means oxygen or sulfur, R1 means alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or by cyano or means cycloalkyl or heterocyclyl substituted, where appropriate, by halogen, by alkyl or by alkoxy or means phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl respectively substituted, where appropriate, R2 means alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl respectively substituted, case
given, by halogen or by cyano or means cycloalkyl, phenyl or benzyl substituted respectively, where appropriate, R 4 and R 5 mean, independently of each other alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio respectively substituted, by Halogen or phenyl, benzyl, phenoxy or phenylthio substituted respectively, where appropriate, R and R7 stand for, independently from each other, hydrogen, meaning alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl respectively substituted, if appropriate, by halogen or by cyano means phenyl or benzyl substituted, respectively, or, together with the N atom, to which they are bonded, form a cycle, which optionally contains oxygen or sulfur and which is optionally substituted. The compounds of the formula (I) can also be present as a function of the type of the substituents in the form of optical isomers or mixtures of isomers, in a variable composition, which can be separated, if appropriate, in a customary manner. Both the pure isomers and also the mixtures of the isomers, their preparation and use, as well as the agents containing them, constitute an object of the present invention. However, the following will be discussed
always the compounds of the formula (I) to simplify, even when they want to indicate both the pure compounds and, if necessary, also mixtures with variable proportions of isomeric compounds. Taking into consideration when D means NH (1) and when D means 0 (2), the following main structures (1-1) and (1-2) are presented:
where A, B, G, Q !, Q2, W, X, Y and Z have the meanings indicated above. Considering the different meanings
(a), (b), (c), (d), (e), (f) and (g) of group G, the main structures (Ila) to (Ilg) below are presented, when D means NH ( 1),
(I-l-a)
(I-l-e)
wherein A, B, E, L,, Q1, Q2, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated above. Taking into account the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the main structures (? -2-a) are presented (? -2-g) following, when D means 0 (2), B
(?-2 g)
wherein A, B, E, L, M, Q1, Q2, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated above. In addition, it has been found that the novel compounds of the formula (I) are obtained according to the procedures described below: (A) the compounds of the formula (I-1-a) are obtained
wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, if the compounds of the formula (II) are condensed intramolecularly
where A, B, Q1, Q2, W, X, Y and Z have the meanings
above, and R8 means alkyl (preferably alkyl having 1 to 6 carbon atoms), in the presence of a diluent and in the presence of a base. (B) In addition it has been found that the compounds of the formula are obtained, (? -2-a)
wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, if compounds of the formula (III) are condensed intramolecularly
wherein A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base.
In addition, it has been found (C) that the compounds of the formulas (Ilb) to (-2 -2-b) shown above are obtained, in which R ^, A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, if compounds of the formulas shown above (1-1-a) are made to react (? -2-a), in which A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, respectively a) with compounds of the formula (IV)
AND (I) OR where
R! has the meaning indicated above and
Hal means halogen (especially chlorine or bromine) or
ß) with anhydrides of carboxylic acids of the formula (V) R 1 -CO-0-CO-R 1 (V) in which
R1 has the meaning indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent;
that the compounds of the formulas (Ilc) to (? -2-c), shown above, are obtained, in which R2, A, B, Q !, Q2, W, M, X, Y and Z have the meanings above indicated and L means oxygen, if compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A, B, Q !, Q2, X, Y and Z have the meanings above indicated, respectively, with esters of chloroformic acid or with thioesters of chloroformic acid of formula (VI) M-C0-C1 (VI)
in which
R2 and M have the meanings indicated above,
if appropriate in the presence of a diluent and, if necessary, in the presence of an acid-accepting agent;
that the compounds of the formulas (Ilc) to (? -2-c) shown above are obtained, in which R2, A, B, Q1, Q2, W, M, X, Y and Z have the meanings indicated above and L means sulfur, if the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A, B, Q !, Q2, W, X, Y and Z have the meanings above indicated, respectively, with esters of chloromonothioformic acid or with esters
of the chlorodithioformic acid of the formula (VII) CI ^ M-R2 Y (VII) s
in which
and R2 have the meanings indicated above,
if appropriate, in the presence of a diluent and, if necessary, in the presence of an acid-binding agent,
(F) that the compounds of the formulas (Ild) to (? -2-d) shown above are obtained, in which R-3, A, B, W, Q !, Q2, X, Y and Z have the above-indicated meanings, if the compounds of the formulas (Ila) to (a-2-a) shown above are reacted, in which A, B, Q !, Q2, X, Y and Z have the meanings indicated above , respectively with sulfonyl chlorides of the formula (VIII) R3-S02 ~ C1 (VIII)
in which
R3 has the abovementioned meaning, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, (G) that the compounds of the formulas (Ile) are obtained up to (? -2- e) previously shown, in which L, R ^,
R5, A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, if the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A , B, Q ^, Q2, W, X, Y and Z have the meanings indicated above, respectively with phosphorus compounds of the formula (IX)
in which
L, R4 and Retain the meanings indicated above
Hal means halogen (especially chlorine or bromine), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, whereby the compounds of the formulas (Ilf) are obtained up to (? -2- f) previously shown, in which E, A,
B, QL, Q2, W, X, Y and Z have the meanings indicated above, if the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A, B, Q !, Q ^,, X, Y and Z have the meanings indicated above, respectively with metal compounds or with amines of the formulas (X)
or (XI) 10 11 R R Me (OR10) t (X) N (??) R in which
Me means a monovalent or divalent metal (preferably an alkaline or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium), t means the number 1 or 2 and RIO, Rll, R12 signify, independently of each other, hydrogen or alkyl ( preferably alkyl having 1 to 8 carbon atoms), if appropriate in the presence of a diluent, (I) to obtain the compounds of the formulas (Ilg) to (? -2-g) shown above, in which L, R6, R7, A, B, Q1, Q2, X, Y and Z have the meanings indicated above, if the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, respectively a) with isocyanates or with isothiocyanates of the formula
(XII) R6-N = C = L (XII) in which
and L have the meanings indicated above,
if necessary in the presence of a diluent and, if necessary, in the presence of a catalyst or
ß) with carbamic acid chlorides or with thiocarbamic acid chlorides of the formula (XIII)
in which
L, R6 and R7 have the meanings given above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent.
It has also been found that the novel compounds of the formula (I) have a very good activity as agents for the control of pests, preferably as insecticides, acaricides and / or fungicides and / or herbicides and, in addition, are frequently , very compatible with plants, especially in front of crop plants. Surprisingly it has now been discovered that certain substituted cyclic ketoenols prevent deterioration of the crop plants, in a particularly good way, when used together with the
compounds (protectants / antidotes) described below, improve the compatibility with the crop plants and which can be used, in a particularly advantageous manner, as preparations in combination of broad activity, for the selective fight against unwanted plants in plant crops useful, such as, for example, cereals as well as corn, soybeans and rice. The object of the invention is constituted by selective herbicidal agents, comprising an active content of a combination of active compounds comprising, as components (a '), at least one substituted cyclic ketoenol of the formula (I), wherein A, B, D, G, Q1, Q2, W, X, Y and Z have the above-indicated meaning and (b ') at least one compound improving compatibility with the crop plants of the following group of compounds : 4-dichloroacetyl-l-oxa-4-aza-spiro [.5] -decane (AD-67, ON-4660), l-dichloroacetyl-hexahydro-3, 3, 8a-trimethylpyrrole [1,2-a] -pyrimidine-6 (2H) -one (Dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine (Benoxacor), 5-chloroquinolin-8-oxy -acetic- (1-methyl-hexyl ester)
(Cloquintocet-mexyl - see also related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3- (2-chloro-benzyl) -1- ( 1-methyl-l-phenyl-ethyl) -urea
(Cumyluron), - (cyanomethoxyimino) -phenylacetonitrile
(Cyometrinil), 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-methyl-phenyl) -urea (Daimuron, Dymron), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), piperidin-1-thiocarboxylate of Sl-methyl-l -phenyl-ethyl (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 (Dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (Fenchlorim), 1- (2,4-dichloro-phenyl) -5-trichloromethyl-1H Ethyl-l, 2,4-triazole-3-carboxylate (Fenchlorazole-ethyl - see also related compounds in EP-A-174562 and EP-A-346620), 2-chloro-4-trifluoromethyl-thiazole-5 -phenylmethyl carboxylate (Flurazole), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -a-trifluoro-acetophenoxy (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2 , 2-dimethyl-oxazolidin (Furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate
(Isoxadifen-ethyl - see also related compounds in the publication OA-95/07897), 1- (ethoxycarbonyl) -ethyl-3,6-dichloro-2-methoxybenzoate (Lactidichlor), acid (4-chloro-o-tolyloxy) -acetic (MCPA), 2- (4-chloro-o-tolyloxy) -propionic acid (Mecoprop), 1- (2,4-dichloro-phenyl) -4,5-dihydro-5-methyl-1H-pyrazole- 3, 5-diethyl dicarboxylate (Mefenpyr-diethyl - see also related compounds in the publication OA-91/07874), 2-dichloromethyl-2-methyl-l, 3-dioxolane (MG-191), 2-
propenyl-l-oxa-4-azaspiro [4.5] decane-4-carbodithioate (MG-838), 1,8-naphthalic acid anhydride, a- (1,3-dioxolan-2-yl-methoxyimino) -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, 4- (4-chloro-phenoxy) ) -butyric, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, 1- (2-chloro-phenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester, 1- (2,4-dichloro-phenyl) Ethyl-5-methyl-lH-pyrazole-3-carboxylate, ethyl 1- (2,4-dichloro-phenyl) -5-isopropyl-lH-pyrazole-3-carboxylate, 1- (2,4-dichloro- ethyl phenyl) -5- (1, 1-dimethyl-ethyl) -lH-pyrazole-3-carboxylate, ethyl 1- (2,4-dichloro-phenyl) -5-phenyl-lH-pyrazole-3-carboxylate (see also related compounds in EP-A-269806 and EP-A-333131) Ethyl 5- (2-dichloro-benzyl) -2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, 5- (4-fluorophenyl) -5-phenyl- Ethyl 2-isoxazoline-3-carboxylate (see also related compounds in the publication OA-91/08202), 5-chloro-quinoline-8-oxy-acetate (1,3-dimethyl-but-1-yl) acid , 5-chloro-quinolin-8-oxy-4-allyloxy-butyl ester, 5-chloro-quinolin-8-oxy-1-allyloxy-prop-2-yl acetate, 5-chloro-quinoxalin-8-oxy -methyl acetate, 5-chloro-quinolin-8-oxy-ethyl acetate, 5-chloro-quinoxalin-8-oxy-allyl acetate,
-chloro-quinolin-8-oxy-2-oxo-prop-1-yl, 5-chloro-quinolin-8-oxy-malonate-diethyl, 5-chloro-quinoxalin-8-oxy-malonate-diallyl, Diethyl 5-chloro-quinolin-8-oxy-malonate (see also related compounds in EP-A-582198), 4-carboxy-chroman-4-yl-acetic acid
(AC-304415, see EP-A-613618), 4-chloro-phenoxy-acetic acid, 3, 3 * -dimethyl-4-methoxy-benzophenone, l-bromo-4-chloromethylsulfonyl-benzene, 1- [ 4- (? -2-methoxybenzoylsulfamoyl) -phenyl] -3-methyl-urea (aka N- (2-methoxy-benzoyl) -4- [(methylamino-carbonyl) -amino] -benzenesulfon-amide), 1- [ 4- (N-2-methoxybenzoylsulfamoyl) -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-benzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds defined by general formulas, of the general formula (lia)
or of the general formula (Hb)
or of the formula (lie)
where m means a number 0,1, 2, 3, 4 or 5, A1 means one of the divalent groupings schematized below
n means a number 0, 1, 2, 3, 4 or 5, A2 means alkanediyl having 1 or 2 carbon atoms substituted, if appropriate, by alkyl having 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms and / or by alkenyloxycarbonyl having 1 to 4 carbon atoms, R 14 means hydroxy, mercapto, amino, alkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or di- (C 1 -C 4) alkyl-amino, R 15 means hydroxy, mercapto, amino, alkoxy with 1 to 7 carbon atoms, alkenyloxy with 1 to 6 carbon atoms, alkenyloxy with 1 to 6 carbon atoms-alkoxy
with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino, means alkyl having 1 to 4 carbon atoms substituted, if appropriate, by fluorine, chlorine and / or bromine, means hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, dioxolanyl-alkyl with 1 to 4 carbon atoms, furyl, furyl-alkyl with 1 to 4 carbon atoms, thienyl , thiazolyl, piperidinyl, substituted, where appropriate, by fluorine, chlorine and / or bromine, or phenyl, substituted, if appropriate, by fluorine, by chlorine and / or by bromine or by alkyl with 1 to 4 atoms of carbon, means hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms , dioxolanyl-alkyl with 1 to 4 carbon atoms, furyl, furyl-alkyl with 1 to 4 carbon atoms, thienyl, thia zolyl, piperidinyl, respectively substituted, by fluorine, by chlorine and / or bromine, or by phenyl, substituted, if appropriate, by fluorine, by chlorine and / or by bromine or by
alkyl having 1 to 4 carbon atoms, R and R1 together also means alkanediyl having 3 to 6 carbon atoms or oxaalkanediyl having 2 to 5 carbon atoms substituted, if appropriate, by alkyl having 1 to 4 carbon atoms , by phenyl, by furyl, by a ringed benzene ring or by two substituents, which form, together with the carbon atom, to which they are bonded, a carboxyl having 5 or 6 members, means hydrogen, cyano, halogen, or alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl substituted, if appropriate, by fluorine, chlorine and / or bromine, means hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or tri- (C1-C4 alkyl) -silylyl substituted respectively, by hydroxy, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, respectively, means hydrogen , cyano, halogen, or means alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl substituted, respectively, by fluorine, chlorine and / or bromine, means nitro, cyano, halogen, alkyl with 1 to 4 atoms carbon, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms,
X means hydrogen, cyano, nitro, halogen, alkyl having 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, X3 means hydrogen, cyano, nitro, halogen, alkyl having 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, and / or the compounds defined below by means of the general formulas, of the general formula (lid)
or of the general formula (lie)
where t means a number 0, 1, 2, 3, 4 or 5, v means a number 0, 1, 2, 3, 4 or 5, R 22 means hydrogen or alkyl with 1 to
carbon, R23 means hydrogen or alkyl having 1 to 4 carbon atoms, R24 means hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, alkylamino having 1 to 6 carbon atoms or di- (C 1 -C 4 -alkyl) -amino substituted, if appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl with 3 to 6 atoms carbon, cycloalkyloxy with 3 to 6 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms or cycloalkylamino with 3 to 6 carbon atoms, respectively substituted, by cyano, halogen or alkyl with 1 to 4 carbon atoms carbon, R 25 is hydrogen, alkyl having 1 to 6 carbon atoms, optionally substituted by cyano, hydroxy, halogen or alkoxy with 1 to 4 carbon atoms, means alkenyl having 3 to 6 carbon atoms or alkynyl with 3 to 6 carbon atoms, substitute respectively, if appropriate, by cyano or by halogen, or means cycloalkyl with 3 to 6 carbon atoms substituted, if appropriate, by cyano or by halogen or by alkyl with 1 to 4 carbon atoms, R26 means hydrogen, alkyl with 1 to 6 carbon atoms
substituted, if appropriate, by cyano, by hydroxy, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl having 3 to 6 carbon atoms or alkynyl with 3 to 6 carbon atoms respectively substituted, if appropriate, by cyano or by halogen means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, or by phenyl, substituted, if appropriate, by nitro, cyano, by halogen, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms, or together with R25 means alkanediyl with 2 to 6 carbon atoms or oxaalkanediyl with 2 to 5 carbon atoms substituted respectivelyoptionally, by alkyl having 1 to 4 carbon atoms, means nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, carbon, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, and means nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or
haloalkoxy with 1 to 4 carbon atoms. The compounds according to the invention are defined, in general, by means of formula (I). The substituents or the preferred ranges of the radicals mentioned in the formulas indicated above and which will be indicated below are explained below: W preferably denotes hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms , alkynyl with 2 to 6 carbon atoms, halogen, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, X means preferably halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms - alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, Y preferably means, in the 4-position, hydrogen, halogen, alkoxy with 1 to 6 carbon atoms, cyano, haloalkyl with 1 to 4 carbon atoms or halogenalkoxy 1 to 4 carbon atoms, Z preferably means hydrogen. W also preferably denotes hydrogen, halogen or
C 1 -C 6 alkyl also preferably means halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenoalkoxy with 1 to 4 carbon atoms or cyano, also preferably means phenyl or pyridyl substituted in the 4-position by V ^ - and by V ^, also preferably means hydrogen, also preferably means halogen, alkyl having 1 to 12 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, also preferably means hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms carbon, v2 mean, together, also preferably alkanediyl having 3 to 4 carbon atoms, which may be substituted, if appropriate, by halogen and / or by alkyl with 1 to 2 carbons and it can be interrupted by one or two oxygen atoms, it also means, preferably, hydrogen, halogen or alkyl with 1 to 6 carbon atoms, means likewise, preferably, halogen, alkyl, with 1 to 6 atoms carbon, alkoxy with 1 to 6
carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, and Y means in the same way, preferably in the 5-position, phenyl or pyridyl substituted by V ^ - and v2, Z means in the same way, preferably, in the position
4, hydrogen, alkyl having 1 to 6 carbon atoms or halogen, V1 also means, preferably, halogen, alkyl having 1 to 12 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, carbon or halogenalkoxy having 1 to 4 carbon atoms, V2 likewise preferably means hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, and v2 mean, together, in the same way, preferably, alkanediyl having 3 to 4 carbon atoms, which may be substituted, if appropriate, by halogen and / or by alkyl having 1 to 2 carbon atoms and which may be interrupted , if necessary, by one or two oxygen atoms. W further preferably denotes hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy
with 1 to 6 carbon atoms, halogen, trifluoromethyl or cyano, furthermore preferably means halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atomsC 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, haloalkyl with 1 to 4 C atoms, haloalkoxy with 1 to 4 C atoms or cyano, further preferably means, in the 4-position, alkyl with 1 to 6 carbon atoms, preferably also means hydrogen, preferably also means hydrogen, halogen, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms, preferably also halogen, alkyl having 1 to 6 carbon atoms C 1 -C 6 -alkoxy, halogen-C 1 -C 4 -alkyl, halogen-C 1 -C 4 -alkoxy or cyano-preferably also means, in the 4-position, hydrogen, halogen or alkyl with 1 to 6 carbon atoms. carbon, halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, also means, preferably in the 3 or 5 position, halogen, alkyl with 1 to 6 carbon atoms,
halogenalkyl with 1 to 4 carbon atoms, cyano, alkoxy with 1 to 6 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms. is preferably an alkanediyl group with 1 to 4 carbon atoms, optionally substituted by alkyl having 1 to 4 carbon atoms or cycloalkyl with 5 to 8 carbon atoms, optionally substituted by alkyl with 1 to 4 carbon atoms of carbon, in which, if appropriate, a methylene group is replaced by oxygen, preferably it means hydrogen or means alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 8 carbon atoms, alkoxy with 1 to 6 carbon atoms C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-bis-C 1 -C 4 -alkoxy, substituted, if appropriate, by halogen, mean phenyl substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by cyano or by nitro, means pyridyl, p irimidyl, thiazolyl or thienyl substituted, if appropriate, by halogen, by alkyl with 1 to 4 carbon atoms or by halogenalkyl with 1 to 2 carbon atoms or means cycloalkyl with 3 to 8 carbon atoms
substituted, if appropriate, by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkyl with 1 to 2 carbon atoms, in which one or two methylene groups, not directly contiguous, they are replaced, if necessary, by oxygen, two methylene groups are replaced by the rest -0-C0- or three methylene groups are replaced by the rest -0-CO-O-. preferably denotes NH or oxygen, preferably hydrogen or means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, if appropriate, by halogen or means cycloalkyl having 3 to 6 carbon atoms substituted, if appropriate, by halogen, by alkyl having 1 to 4 carbon atoms carbon or by alkoxy having 1 to 4 carbon atoms, where appropriate, a methylene group is replaced by oxygen or is phenyl, phenyl-alkyl with 1 to 2 carbon atoms or substituted hetaryl, respectively, optionally, one or two sometimes by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms,
Q2 preferably means hydrogen or alkyl having 1 to 6 carbon atoms, or Q! and Q2 signify, together with the carbon atom, to which a 3 to 6-membered ring is attached, optionally substituted one to two times by fluorine, by chlorine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by trifluoromethyl, the methylene group being replaced by oxygen. G preferably means hydrogen (a) or means one of the groups
in which
E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur. R! preferably it means alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms, alkylthio with 1 to 8 carbon atoms-alkyl with 1 at 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms
substituted respectively, by halogen, if appropriate
0 per cyano or means cycloalkyl with 3 to 8 carbon atoms substituted, if appropriate by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms, in which, if appropriate, one or two methylene groups, not directly contiguous, are replaced by oxygen and / or by sulfur, means phenyl substituted, if appropriate, by halogen, by cyano, by nitro, by alkyl by 1 to 6 carbon atoms, by alkoxy by 1; to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, alkylthio with
1 to 6 carbon atoms or alkylsulfonyl with 1 to 6 carbon atoms, means phenyl-alkyl with 1 to 6 carbon atoms substituted, if appropriate, by halogen, by nitro, by cyano, by alkyl with 1 to 6 carbon atoms carbon, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms or by haloalkoxy with 1 to 6 carbon atoms, means hetaryl with 5 or 6 members substituted, if appropriate by halogen or by alkyl with 1 to 6 carbon atoms, with one or two heteroatoms of the series consisting of oxygen, sulfur and nitrogen, means phenoxy-alkyl with 1 to 6 carbon atoms
substituted, if appropriate, by halogen or by alkyl having 1 to 6 carbon atoms or means hetaryloxy with 5 or 6 members-alkyl having 1 to 6 carbon atoms substituted, if appropriate, by halogen, by amino or by alkyl with 1 to 6 carbon atoms, with one or two heteroatoms of the series consisting of oxygen, sulfur and nitrogen. preferably it means alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl having 2 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl with 2 to 8 carbon atoms substituted, if appropriate, by halogen or cyano, means cycloalkyl with 3 to 8 carbon atoms, optionally substituted by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms or means phenyl or benzyl substituted, if appropriate, by halogen, by cyano, by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by haloalkyl with 1 to 6 carbon atoms or by haloalkoxy with 1 to 6 carbon atoms. preferably it means alkyl having 1 to 8 carbon atoms, substituted, if appropriate, by halogen or
means phenyl or benzyl substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms, by cyano or by nitro. and R5 signify, independently of each other, preferably alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms or alkenylthio with 3 to 8 carbon atoms substituted, if appropriate, by halogen or means phenyl, phenoxy or phenylthio substituted, if appropriate, by halogen, by nitro, by cyano, by alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkyl with 1 to 4 carbon atoms or for haloalkyl with 1 to 4 carbon atoms. and they mean, independently of each other, preferably hydrogen, they mean alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkenyl with 3 to 8 carbon atoms or alkoxy with 1 to 8 atoms of
carbon-alkyl with 2 to 8 carbon atoms substituted, if appropriate, by halogen or by cyano, means phenyl or benzyl substituted, if appropriate, by halogen, by alkyl with 1 to 8 carbon atoms, by haloalkyl with 1 to 8 carbon atoms or alkoxy with 1 to 8 carbon atoms or together they mean an alkylene radical having 3 to 6 carbon atoms substituted, optionally with alkyl having 1 to 6 carbon atoms, in which it is replaced, if necessary, a methylene group by oxygen or by sulfur. In the definitions of the moieties, referred to as referents, halogen means fluorine, chlorine, bromine and iodine, especially means fluorine, chlorine and bromine. particularly preferably hydrogen, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, especially preferably chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, halogenalkyl with 1 to 2 carbon atoms,
halogenoalkoxy having 1 to 2 carbon atoms or cyano, especially preferably in the 4-position, means hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy, especially preferably hydrogen. also particularly preferably hydrogen, chlorine, bromine or alkyl having 1 to 4 carbon atoms, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkyl is also particularly preferred. with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or cyano, also means, particularly preferably, position 4, the rest
Z is also particularly preferably hydrogen, V1 also particularly preferably means fluorine, chlorine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms.
carbon atoms or halogenalkoxy having 1 to 2 carbon atoms, V2 also particularly preferably means hydrogen, fluorine, chlorine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms of carbon, v and V ^ mean, together, also particularly preferably -0-CH2-0- and -0-CF2-0-. W in the same way is particularly preferably hydrogen, chlorine, bromine or alkyl having 1 to 4 carbon atoms, X in the same way, particularly preferably chlorine, bromine, alkyl having 1 to 4 carbon atoms or halogenalkyl with 1 to 2 carbon atoms,
And in the same way, in the fifth position, the rest is particularly preferred.
In the same way, particularly preferably, in the 4-position, hydrogen, alkyl having 1 to 4 carbon atoms or chlorine, means in a particularly preferred way fluorine, chlorine, alethyl with 1 to 4 carbon atoms.
carbon, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, means in the same way, particularly preferably hydrogen, fluorine, chlorine, alkyl with 1 to 4 carbon atoms. carbon, alkoxy with 1 to 4 carbon atoms or halogenalkyl with 1 to 2 carbon atoms, and v2 mean, on the whole, in the same way with particular preference -O-CH2-O- and -O-CF2-O-. furthermore, it is particularly preferably hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, chlorine, bromine or trifluoromethyl, furthermore, it is particularly preferably chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or cyano, means also, with particular preference, in the 4-position, alkyl with 1 to 4 carbon atoms, also means especially preferably
Irogen
W is also particularly preferably hydrogen, chlorine, bromine, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, X is also particularly preferably chlorine, bromine, alkyl with 1 to 4 carbon atoms C 1 -C 4 -alkoxy, halogen-alkyl with 1 to 2 carbon atoms, halogen-alkoxy with 1 to 2 carbon atoms or cyano-means also, particularly preferably, in the 4-position, hydrogen, chlorine, bromine, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, also particularly preferably in the 3 or 5 position, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, especially preferably an alkanediyl group with 1 to 3 carbon atoms optionally substituted by alkyl having 1 to 2 carbon atoms or cycloalkyl with 5 to 6 carbon atoms, in which, if appropriate, a methylene group is replaced by oxygen. particularly preferably hydrogen or alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6
carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, alkoxy with 1 to 4 carbon atoms- bis-alkoxy with 1 to 3 carbon atoms each substituted, if appropriate, one to three times by fluorine or by chlorine, means phenyl substituted, optionally one to three times by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, for halogenalkyl with 1 to 2 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms, for cyano or for nitro, means pyridyl, pyrimidyl, thiazolyl or thienyl substituted, optionally twice with fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl or cycloalkyl with 3 to 6 carbon atoms, optionally one to two times fluorine, chlorine, methyl, methoxy or trifluoromethyl, in which two groups are replaced, if necessary tile, not directly contiguous, by oxygen. particularly preferably NH or igene. particularly preferably hydrogen, means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms substituted,
If appropriate, one to three times fluorine, or cycloalkyl with 3 to 6 carbon atoms, optionally one to two times fluorine, chlorine, methyl, ethyl or methoxy; In this case, a methylene group by oxygen means, in a particularly preferred manner, hydrogen or alkyl with 1 to 4 carbon atoms. Q2 mean, together, with the carbon atom, with which they are bonded, particularly preferably a ring with 3 to 6 members monosubstituted, if appropriate, by fluorine, by methyl, by methoxy or by trifluoromethyl, and can be replaced if necessary, a methylene group by oxygen. particularly preferably hydrogen (a) or means one of the groups
in which
E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur. especially preferably alkyl with 1
to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms or poly-alkoxy having 1 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or means cycloalkyl having 3 to 7 carbon atoms substituted, given one to two times by fluorine, by chlorine, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, where one or two methylene groups, not directly adjacent, are optionally replaced , by oxygen and / or by sulfur, means phenyl substituted, optionally one to three times by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl by 1 to 4 carbon atoms, by alkoxy by 1; to 4 carbon atoms, for halogen alkyl with 1 to 3 carbon atoms, for halogenalkoxy with 1 to 3 carbon atoms carbon, by alkylthio with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, means phenyl-alkyl with 1 to 4 carbon atoms substituted, optionally one to two times by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by
halogenalkyl having 1 to 3 carbon atoms or halogenalkoxy having 1 to 3 carbon atoms means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl substituted respectively, optionally one to two times fluorine, chlorine, bromine or by alkyl having 1 to 4 carbon atoms, means phenoxy-alkyl having 1 to 5 carbon atoms, optionally substituted one to two times by fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms. carbon or means pyridyloxy-alkyl with 1 to 5 carbon atoms, pyrimidyloxy-C 1 -C 5 -alkyl or thiazolyloxy-C 1 -C 5 -alkyl respectively substituted, optionally, one to two times by fluorine, by chlorine, by bromine, by amino or by alkyl with 1 to 4 carbon atoms. particularly preferably, alkyl having 1 to 16 carbon atoms, alkenyl having 2 to 16 carbon atoms, alkoxy having 1 to 6 carbon atoms-alkyl having 2 to 6 carbon atoms or poly-alkoxy having 1 to 6 carbon atoms carbon-alkyl with 2 to 6 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine, means cycloalkyl having 3 to 7 carbon atoms, optionally substituted one to two times by fluorine ,
for chlorine, for alkyl with 1 to 4 carbon atoms or for alkoxy with 1 to 4 carbon atoms or means phenyl or benzyl respectively substituted, if appropriate, one to three times by fluorine, by chlorine, by bromine, by cyano , by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, is particularly preferably alkyl with 1 to 6 carbon atoms, optionally substituted one to three times by fluorine or by chlorine or by phenyl or benzyl respectively, optionally one to two times by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 2 carbon atoms, for halogenalkyl with 1 to 2 carbon atoms, for cyano or for nitro. they mean, independently of each other, particularly preferably alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms, di- (alkyl with 1 to 6 carbon atoms) amino , alkylthio having from 1 to 6 carbon atoms or alkenylthio having from 3 to 4 carbon atoms substituted, if appropriate, from one to three times by fluorine or by chlorine or by phenyl, phenoxy or phenylthio
respectively substituted, optionally one to two times by fluorine, by chlorine, by bromine, by nitro, by cyano, by alkoxy with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 3 carbon atoms, halogenalkylthio with 1 to 3 carbon atoms, alkyl with 1 to 3 carbon atoms or halogenalkyl with 1 to 3 carbon atoms. they mean, independently of each other, particularly preferably hydrogen, they mean alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyl with 3 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms-alkyl having 2 to 6 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine, means phenyl or benzyl substituted respectively, optionally, one to three times by fluorine, chlorine, bromine, halogenalkyl with 1 to 5 carbon atoms, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, or together they mean an alkylene radical with 3 to 6 atoms of carbon substituted, if appropriate, by alkyl having 1 to 4 carbon atoms, in which, if appropriate, a methylene group is replaced by oxygen or by sulfur. In the definitions of the remains, cited in a way
especially preferred, halogen means fluorine, chlorine and bromine, especially fluorine and chlorine. W very particularly preferably means hydrogen, methyl, chlorine, bromine, ethyl, methoxy, ethoxy or trifluoromethyl, X very particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Y means very particularly preferably, in the 4-position, hydrogen, chlorine, bromine, trifluoromethyl or trifluoromethoxy, Z very particularly preferably means hydrogen. W also very particularly preferably means hydrogen, chlorine, bromine, methyl or ethyl, X also very particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano, and also very highly. particularly preferred, in position 4, the rest
Z also means very specially
Preferred hydrogen, V1 also very particularly preferably means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 also very particularly preferably means hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl. W in the same way very particularly preferably hydrogen, chlorine or methyl, X in the same way, very particularly preferably chlorine, methyl or trifluoromethyl, Y means in a very particularly preferred way, in the 5-position, the rest
in the same way, very particularly preferably, in the 4-position, hydrogen or methyl, means in a very particularly preferred way fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, in the same way very particularly preferably hydrogen means , fluorine, chlorine, methyl, methoxy or trifluoromethyl. it also very particularly preferably means hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine,
X also very particularly preferably means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, and Y means in a very particularly preferred manner, position 4, methyl or ethyl, Z also very particularly preferably means hydrogen. W also very particularly preferably means hydrogen, chlorine, bromine, methyl or ethyl, X also very particularly preferably chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy, and Y means also very particularly preferably , in the 4-position, hydrogen, chlorine, bromine, methyl or ethyl, Z also very particularly preferably means, in the 3 or 5 position, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or trifluoromethoxy. A very particularly preferably means -CH2-, -CHCH3-, -CH2-CH2-, -CH2-CHCH3-, -CH2-CH2-CH2-. B very particularly preferably means hydrogen, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, alkenyl having 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy,
Methoxy-ethoxy, ethoxy-ethoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy ,. by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, means cyclopentyl or cyclohexyl, in which, if appropriate, a mutylene group is replaced by oxygen. D very particularly preferably means NH or oxygen. it very particularly preferably means hydrogen, methyl, ethyl, propyl, iso-propyl, cyclopropyl, cyclopentyl or cyclohexyl. Q2 very particularly preferably means hydrogen, methyl or ethyl. Q! and Q2 mean very particularly preferably together with the carbon atom, with which cyclopropyl, cyclopentyl or cyclohexyl are linked. G very particularly preferably means hydrogen
(a) or means one of the groups
O L R4 ^ R1 i (bb)), -r2 -SO ^ R3 - P M '(c),
those who
E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur. it very particularly preferably means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 4 carbon atoms -alkyl with 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or means cycloalkyl with 3 to 6 carbon atoms monosubstituted, if appropriate, by fluorine, by chlorine, by methyl , by ethyl or methoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by ethyl, by n-propyl, by i-propyl , by methoxy, by ethoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, where appropriate by chlorine, by bromine or by methyl. it very particularly preferably means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl having 2 to 4 carbon atoms, respectively substituted, if appropriate, to three times fluorine or chlorine,
means cyclopentyl or cyclohexyl or means phenyl or benzyl respectively substituted, if appropriate, one to two times by fluorine, by chlorine, by cyano, by nitro, by methyl, by ethyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. R3 very particularly preferably means methyl, ethyl, propyl or isopropyl substituted, where appropriate, one to three times by fluorine or chlorine, or phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine , by methyl, by ethyl, by isopropyl, by tere. -butyl, by methoxy, by ethoxy, by iso-propoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro. and R5 mean, independently of each other, very particularly preferably alkoxy having 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms or meaning phenyl, phenoxy or phenylthio monosubstituted respectively, optionally fluorine, chlorine, bromine, by nitro, by cyano, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. R6 and R7 signify, independently of each other, very particularly preferably hydrogen, meaning alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms,
alkenyl with 3 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms-alkyl with 2 to 4 carbon atoms, means substituted phenyl, optionally one to two times for fluorine, for chlorine, for bromine, for methyl , by methoxy or by trifluoromethyl, or together they mean an alkylene radical having 5 to 6 carbon atoms, in which, if appropriate, a methylene group is replaced by oxygen or by sulfur. W is particularly preferably hydrogen, methyl, ethyl, chlorine or bromine (meaning hydrogen, methyl, ethyl or chlorine), X is particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy. -ethoxy, cyclopropyl-methyloxy, trifluoromethyl or difluoromethoxy (meaning chlorine, bromine, ethyl, methoxy or ethoxy), Y means particularly preferably in the 4-position, hydrogen, chlorine, bromine, trifluoromethyl or trifluoromethoxy (meaning chlorine or chlorine). bromine), Z is particularly preferably hydrogen, A is particularly preferably -CH2-, CHCH3- or -CH2-CH2- (denoted by -CH2- or -CH2- CH2-), B is particularly preferably hydrogen. ,
methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, cyclopentyl or cyclohexyl (markedly means hydrogen, methyl, ethyl, propyl or methoxy), D means particularly preferably NH, Q ! particularly particularly preferably hydrogen or methyl (meaning hydrogen), Q2 particularly particularly preferably hydrogen or methyl (in particular hydrogen), G is particularly particularly preferably hydrogen (a) or means one of the groups L ^ 1 (b), M '(c), (d), in which
L means oxygen and
means oxygen or sulfur (markedly means oxygen), R! particularly preferably, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkoxy having 1 to 2 carbon atoms-alkyl with 1
at 2 carbon atoms, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl
Cyclohexyl, means monosubstituted phenyl, optionally fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, optionally , by chlorine or by methyl (notably means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, cyclopropyl, means phenyl or thienyl substituted by chlorine), means in a particularly preferred alkyl with
1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with
2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, respectively, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (notably means alkyl with 1 to 8 carbon atoms, alkenyl
with 2 to 6 carbon atoms or benzyl). R 3 is particularly preferably phenyl substituted by methyl. W is also particularly preferably hydrogen, chlorine, bromine, methyl or ethyl, X is also particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano, and Y is also particularly preferably in position 4, the rest
Z is also particularly preferably hydrogen, V1 also particularly preferably means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 is also particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
A is also particularly preferably -CH2-, -CHCH3- or -CH2-CH2-, B also particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl having 2 to 4 carbon atoms, methoxy , ethoxy, propoxy,
isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, also means especially preferred
H, 1 is also particularly preferably hydrogen or methyl, 2 also very particularly preferably hydrogen or methyl, hydrogen (a) is also particularly preferred or represents one of the groups
in which
L means oxygen and M means oxygen or sulfur, also very particularly preferably alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms - alkyl with 1 to 2 carbon atoms. carbon, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, respectively, from one to three
sometimes by fluorine or by chlorine or means cyclopropyl, cyclopentyl or cyclohexyl, means monosubstituted phenyl, optionally fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl , thienyl or pyridyl monosubstituted, respectively, by chlorine or methyl, is also particularly preferably alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, optionally fluorine, chlorine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy. means in the same particularly preferred way hydrogen or methyl (in particular hydrogen), means in the same way chloro or methyl (in the same way meaning methyl), it means in a particularly preferred way, in position 5, the rest
Z in the same way, particularly preferably, in the 4-position, hydrogen or methyl (meaning hydrogen), V1 also means particularly preferably fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 in the same way particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl (Y signifi- cantly means phenyl substituted by chlorine), A also signifies in a particularly preferred way -CH2-, -CHCH3- or -CH2-CH2- (notably means -CH2-), B also means particularly preferably hydrogen, methyl, ethyl, propyl, isopropyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means substituted phenyl , if appropriate, one to two times fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro
(meaning propyl), D means, in the same way, particularly preferably NH, in the same way, particularly preferably hydrogen or methyl (notably means
hydrogen), Q2 in the same way, particularly preferably hydrogen or methyl (in particular hydrogen), G is likewise particularly preferably hydrogen (a) or means one of the groups
(markedly means hydrogen),
in which
L means oxygen and M means oxygen or sulfur, R! in the same way, particularly preferably, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkoxy having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms, alkylthio having 1 to 2 atoms carbon-alkyl with 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or by chlorine or means cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy,
means furanyl, thienyl or pyridyl respectively substituted, if appropriate, by chlorine or by methyl, R 2 means in a particularly preferred way alkyl having 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-C2-C3-alkyl, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted, respectively, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or trifluoromethoxy. W furthermore particularly preferably means hydrogen, methyl, ethyl, chlorine or bromine (notably methyl, ethyl, chlorine or bromine), X furthermore particularly preferably means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy , H 3 CO- (CH 2) 2 ~ 0 'cyclopropylmethoxy, trifluoromethyl or difluoromethoxy (meaning chlorine, bromine, methyl, ethyl, methoxy or H 3 CO- (CH 2) 2 °)) > In addition, particularly particularly preferably, in the 4-position, methyl, Z furthermore particularly preferably means hydrogen, A furthermore particularly particularly signifies -CH2-, -CHCH3- or
-CH2-CH2- (notably means -CH2- or -CH2-CH2-), B furthermore particularly particularly means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy , propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, means cyclopentyl or cyclohexyl, in which, if appropriate, a methylene group is replaced by oxygen (notably hydrogen, methyl, ethyl, propyl, iso-propyl, methoxy or cyclopropyl), Q! also particularly preferably hydrogen or methyl, Q2 furthermore particularly preferably means hydrogen or methyl, D also means particularly preferably
NH, G furthermore signifies particularly preferably hydrogen (a) or means one of the groups
in which
E means an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, means also particularly preferably alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms. carbon-alkyl having 1 to 2 carbon atoms, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means monosubstituted phenyl, optionally fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy;
means furanyl, thienyl or pyridyl monosubstituted, respectively, by chlorine or by methyl (markedly means alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 2 carbon atoms - alkyl having 1 to 2 carbon atoms, cyclopropyl monosubstituted , if appropriate by chlorine, means phenyl, pyridyl thienyl or
substituted by chlorine) also means particularly preferably alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 4 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl respectively substituted, if appropriate, by fluorine, by chlorine , by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (meaning alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or benzyl), means also particularly preferably methyl or means phenyl substituted by methyl, together they mean, in a particularly preferred way an alkylene radical having 5 to 6 carbon atoms, in which a methylene group means oxygen. also particularly preferably hydrogen, methyl, chlorine or bromine (meaning hydrogen or methyl), also particularly preferably chlorine, bromine, methyl, methoxy or trifluoromethyl (in particular methyl), also means particularly preferably in
position 4, hydrogen, chlorine, bromine or methyl (meaning hydrogen or methyl), Z also means particularly preferably in position 3 or 5, chlorine, bromine, methyl, ethyl, trifluoromethyl or trifluoromethoxy (notably methyl) , A also means particularly preferably - CH2-, -CHCH3- or
-CH2-CH2- (notably means -CH2-), B also means particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy , isobutoxy, cyclopropyl, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro (markedly - means hydrogen , methyl, ethyl or cyclopropyl), D also very particularly preferably NH, Q1 also particularly preferably hydrogen or methyl (in particular hydrogen), Q2 also particularly preferably hydrogen or methyl (meaning hydrogen), G it also means particularly preferably
hydrogen (a) or means one of the groups O L ^ R1 (b), / ^ M'R (C), (markedly means hydrogen or group (c)),
in which
L means oxygen and means oxygen or sulfur (meaning oxygen), it also means particularly preferably alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms - alkyl with 1 at 2 carbon atoms, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms, respectively substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, where appropriate by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted, respectively, by chlorine or by methyl , R <2> is also particularly preferably alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkoxy having 1 to 2 carbon atoms-
alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (respectively) notably, it means alkyl with 1 to 8 carbon atoms). W furthermore means, particularly preferably hydrogen, methyl, ethyl, chlorine or bromine (in particular hydrogen, chlorine, methyl or ethyl), X furthermore, particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy. , propoxy, trifluoromethyl, difluoromethoxy or cyano (markedly means chlorine, bromine, methyl, ethyl or trifluoromethyl), Y furthermore, particularly preferably, in the 4-position, hydrogen, chlorine, bromine, methoxy, trifluoromethyl or trifluoromethoxy (notably means hydrogen, chlorine, bromine or methoxy), Z furthermore signifies, particularly preferably hydrogen, A furthermore particularly particularly signifies -CH2-, B furthermore, particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl , alkenyl
with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl , by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, cyclopentyl or cyclohexyl (markedly means hydrogen or propyl), D also means, particularly preferably oxygen, Q! furthermore, particularly preferably hydrogen or methyl (markedly means hydrogen),?) 2 also means, particularly preferably hydrogen or methyl (in particular hydrogen), G means particularly preferably hydrogen
(a) or means one of the groups O L - ^ R1 (b), M'R2 (C), (markedly means hydrogen or group (b)),
in which
L means oxygen and M means oxygen or sulfur, R1 also means, particularly preferably alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-
alkyl having 1 to 2 carbon atoms, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl is phenyl, monosubstituted phenyl, optionally fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted, respectively, by chlorine or methyl (meaning alkyl with 1 to 6 carbon atoms), furthermore, particularly preferably alkyl having 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms -alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by t rifluormethyl or trifluoromethoxy. furthermore, it also means particularly preferably hydrogen, chlorine, bromine, methyl or ethyl (notably methyl),
X furthermore, also particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano (markedly means methyl or ethyl), Y furthermore, particularly preferably, in the 4-position, rest
Z furthermore, and particularly preferably hydrogen, is also V1, especially preferably fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 furthermore, particularly preferably also hydrogen, fluorine, chlorine, methyl, methoxy. or trifluoromethyl, and means in addition, also particularly preferably
I A furthermore means, also particularly preferably -CH2-, B furthermore, also particularly preferably hydrogen, methyl, ethyl, propyl, iso-
propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy , by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro (markedly means hydrogen or methyl), means also, especially in a particularly oxygen-related manner, also means, also particularly preferably hydrogen or methyl (markedly means hydrogen), means in addition, also particularly preferably hydrogen or methyl (in particular hydrogen), means also, particularly preferably, hydrogen (a) or means one of the groups OL ^ R1 (b), / ^ M 'R (C), (notably means hydrogen),
in which
L means oxygen and M means oxygen or sulfur,! also means, especially preferably alkyl having 1 to 6 carbon atoms, alkenyl
with 2 to 6 carbon atoms, alkoxy having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms, alkylthio having 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, respectively, optionally one to three times by fluorine or by chlorine or means cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, if appropriate, by chlorine or by methyl, means also, particularly preferably, alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate, by fluorine, by chlorine , by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (notably means alkyl with 1 to 8 carbon atoms). means in the same way, particularly preferably hydrogen or methyl, also means, in the same way, in the same way particularly preferably chlorine or methyl, also means, in the same way, particularly preferably, in position 5, the rest
Z furthermore means, in the same way, particularly preferably in the 4-position, hydrogen or methyl, V1 furthermore, particularly, particularly preferably fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 furthermore means likewise, particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, Y furthermore, in the same way, particularly preferably
A furthermore means, in the same particularly preferred manner -CH2-, B furthermore, particularly particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl having 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy,
isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro (markedly means hydrogen), also means, in the same way, particularly preferably oxygen, means in the same way, particularly preferably methyl hydrogen
(denoted by hydrogen), it also means, in the same way, particularly preferably methyl hydrogen
(meaning hydrogen), means, in the same way, particularly preferably hydrogen (a) or means one of the groups
wherein L means oxygen and M means oxygen or sulfur (specifically meaning xylene), 1 also means, in the same way, particularly preferably alkyl having 1 to 6 carbon atoms.
carbon, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms substituted respectively, in given case, from one to three times by fluorine or by chlorine or means cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, by chlorine or by methyl (markedly means alkyl having 1 to 6 carbon atoms), furthermore means, particularly preferably alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl having 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means monosubstituted phenyl or benzyl ectively, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (notably means alkyl with 1 to 8 carbon atoms).
W also, more particularly, particularly preferably hydrogen, methyl, chlorine or bromine, X also means, particularly preferably, chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, trifluoromethyl, difluoromethoxy or cyano
(in particular it means chlorine, bromine, methyl or methoxy), Y means, in addition, particularly preferably, in the 4-position, methyl or ethyl, Z also signifies, in addition, particularly preferred hydrogen, A also means, in particular, particularly preferably -CH2-, B also means, particularly preferably hydrogen, methyl, ethyl, propyl, isopropyl, alkenyl having 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, phenyl. It may be substituted, if appropriate, one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, cyclopropyl, cyclopentyl or cyclohexyl, in which replaced, if necessary, a methylene group by oxygen (markedly means hydrogen or propyl), Q! furthermore, particularly preferably hydrogen or methyl (notably means
hydrogen), Q2 also, more particularly, particularly preferably hydrogen or methyl (in particular hydrogen), D also means particularly preferably oxygen, G also means, particularly preferably hydrogen (a) or one of the groups
in which
L means oxygen and M means oxygen or sulfur (markedly means oxygen), R! more particularly, it also means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon-alkyl atoms having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or by chlorine or means cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine , by bromine, by cyano, by nitro, by
methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, if appropriate, by chlorine or methyl (in particular by alkyl having 1 to 6 carbon atoms), also means, in particular, in particular preferably alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms or alkoxy having 1 to 2 carbon atoms-alkyl having 2 to 4 carbon atoms, means cyclopentyl or cyclohexyl, or means monosubstituted phenyl or benzyl respectively, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy (notably means alkyl with 1 to 10 carbon atoms). furthermore, it is particularly preferably hydrogen, methyl, chlorine or bromine (in particular hydrogen, chlorine or methyl), and more particularly chlorine, bromine, methyl, methoxy or trifluoromethyl (meaning chlorine, bromine or methyl), furthermore, particularly preferably, in the 4-position, hydrogen, chlorine, bromine or methyl, also means, in a particularly preferred manner, in
position 3 or 5, chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl or trifluoromethoxy (notably means fluorine, chlorine, bromine or methyl), also means, particularly preferably
furthermore, particularly preferably hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl having 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, represents substituted phenyl, optionally two times fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, means cyclopropyl, cyclopentyl or cyclohexyl, where, if necessary, a methylene group by oxygen (markedly means hydrogen or propyl), Q! furthermore it means, particularly preferably hydrogen or methyl (markedly hydrogen), Q2 furthermore, particularly preferably hydrogen or methyl (meaning hydrogen),
D furthermore means, particularly preferably oxygen, G furthermore, particularly preferably hydrogen (a) or means one of the groups
(denoted by hydrogen), wherein L means oxygen and M means oxygen or sulfur, means also, more preferably, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 atoms carbon-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means monosubstituted furanyl, thienyl or pyridyl, respectively, given, by chlorine or by methyl, also means, particularly preferably alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms or alkoxy having 1 to 2 carbon atoms-alkyl having 2 to 4 carbon atoms,
means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. The definitions of the remains or the explanations mentioned above in a general manner or indicated in the preferred ranges can be combined arbitrarily with each other, that is to say even between the intervals and between the corresponding preferred ranges. These are valid for the final products as well as, correspondingly, for the starting products and for the intermediate products. According to the invention, the compounds of the formula (I) are preferred, in which a combination of the meanings indicated above is preferred (preferably). According to the invention, the compounds of the formula (I) are particularly preferred, in which a combination of the meanings given above is especially preferred. According to the invention, very particularly preferred are the compounds of the formula (I), in which a combination of the meanings indicated above is present as very particularly preferred.
According to the invention, the compounds of the formula (I), in which a combination of the meanings indicated above are particularly preferred, are particularly preferred. The saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl can be, even in combination with heteroatoms, such as, for example, alkoxy, as far as possible, respectively straight-chain or branched chain. The residues, substituted, if necessary, may be monosubstituted or polysubstituted, insofar as it is not otherwise stated, the substituents being the same or different in the case of polysubstitutions. In particular, the following compounds of the formula (I-1-a) can be mentioned in addition to the compounds indicated in the preparation examples: Table 1
Table 2: A,, X, Y and Z as indicated in table 1 B = CH3 Table 3: A, W, X, Y and Z as indicated in table 1 B = C2H5 Table 4 A, W , X, Y and Z as indicated in table 1 B = C3H7 Table 5: A, W, X, Y and Z as indicated in table 1 B = i-C3H7 Table 6: A, W, X , Y and Z as indicated in table 1
B
Table 7: A, W, X, Y and Z as indicated in table 1
Table 8: A, W, X, Y and Z as indicated in table 1 A = -CH2-CH2-; B = OCH3 Table 9: A, W, X, Y and Z as indicated in table 1 A = -CH2-CH2-; B = OC2H5 In particular, the following null compounds (? -2-a), mentioned in the preparation examples can be mentioned:
ABX w YZ CH2 H CH3 HHH CH2 H Br HHH CH2 H Cl HHH CH2 H CF3 HHH CH2 H OCH3 HHH CH2 H Br H 4-Cl H CH2 H Cl H 4-Br H CH2 H Cl H 4-Cl H CH2 H Cl H 4-CH 3 H CH 2 H CH 3 H 4-Cl H
A B X Y Z
CH2 H CH3 H 4-CH3 H
CH2 H Cl Cl H H
CH2 H Cl OCH3 H H
CH2 H Cl CH3 H H
CH2 H Cl OC2H5 H H
CH2 H OCH3 OCH3 H H
CH2 H CH3 CH3 H H
CH2 H C2H5 CH3 H H
CH2 H C2H5 C2H5 H H
CH2 H Br CH3 4-Br H
CH2 H Cl Cl 4-CH3 H
CH2 H CH3 Br 4-CH3 H
CH2 H CH3 Cl 4 -CH3 H
CH2 H OCH3 CH3 4-CH3 H
CH2 H OCH3 C2H5 4-CH3 H
CH2 H OC2H5 CH3 4-CH3 H
CH2 H OC3H7 CH3 4-CH3 H
CH2 H CH3 CH3 4-CH3 H
CH2 H Br Br 4-CH3 H
CH2 H Cl Cl 4-CH3 H
CH2 H CH3 CH3 4-Br H
CH2 H CH3 CH3 4-OCH3 H
CH2 H Br Cl 4 -CH3 H
CH2 H Br CH3 4-C1 H
CH2 H Cl CH3 4-Br H
CH2 H CH3 CH3 4-C1 H
CH2 H C2H5 CH3 4-CH3 H
CH2 H C2H5 C2H5 4-CH3 H
CH2 H C2H5 CH3 4-C2H5 H
? B X w Y Z CH2 H C2H5 C2H5 4-C2H5 H
CH2 H C2H5 CH3 4-C1 H
CH2 H C2H5 C2H5 4-C1 H
CH2 H C2H5 CH3 4-Br H
CH2 H C2H5 C2H5 4-Br H
CH2 H C2H5 Cl 4 -CH3 H
CH2 H C2H5 Br 4-CH3 H
CH2 H 2H5 Cl 4-C1 H
CH2 H C2H5 Br 4-Br H
CH2 H C2H5 Cl 4-Br H
CH2 H C2H5 Br 4-C1 H
CH2 H OCH3 CH3 4-C1 H
CH2 H OCH3 C2H5 4-C1 H
CH2 H OC2H5 CH3 4-C1 H
CH2 H OC2H5 C2H5 4-C1 H
CH2 H Cl OCH3 4-CH3 H
CH2 H Cl OC2H5 4-CH3 H
CH2 H CH3 CH3 4-C1 H
CH2 H Cl H 4-C1 5-C1
CH2 H CH3 H 4-CH3 5-CH3
CH2 H CH3 H 4-C1 5-CH3
CH2 H Br H 4-C1 5-CH3
CH2 H Br H 4-CH3 5-CH3
CH2 H Cl H 4-Br 5-CH3
CH2 H Cl H 4-C1 5-CH3
CH2 H CH3 H 4-Br 5-CH3
CH2 H Cl H 4-CH3 5-C1
CH2 H CH3 H H 5-CH3
CH2 H Cl H H 5-CH3
A B X W Y Z
CH H Br H H 5-CH3
CH2 H CH3 H H 5-C1
CH2 H CH3 H H '5-Br
CH2 H CH3 CH3 4-CH3 5-CH3
CH2 H CH3 CH3 4-CH3 5-C1
CH2 H CH3 CH3 -CH3 5-Br
CH2 H CH3 CH3 H 3-C1
CH2 H CH3 CH3 H 3-Br
CH H Cl Cl H 3-Br
CH2 H CH3 CH3 4- (4-Cl- H C6H4) CH2 H C2H5 CH3 4- (4-Cl- H C6H4) CH2 H C2H5 C2H5 4- (4-Cl- H C6H4) CH2 H Cl CH3 4- (4 -Cl- H C6H4) CH2 H Cl C2H5 4- (4-Cl- H C6H4) CH2 H CH3 H 5- (4-Cl- H C6H4) CH2 H CH3 CH3 5- (4-Cl- H C6H4) CH2 H CH3 H 5- (4-Cl- 4-CH3 C6H4) CH2 H CH3 CH3 5- (4-Cl- 4-CH3 C6H4) CH2 H Cl H 5- (4-Cl- H C6H4)
Table 11: A, W, X, Y and Z as indicated in Table 10 B = CH3 Table 12: A, W, X, Y and Z as indicated in Table 10 B = C2H5 Table 13: A , W, X, Y and Z as indicated in Table 10 B = C3H7 Table 14: A, W, X, Y and Z as indicated in Table 10 B = Í-C3H7 Table 15: A, W , X, Y and Z as indicated in table 10
B =
Table 16: A, W, X, Y and Z as indicated in table 10 or - »B -" O Table 17: W, X, Y and Z as indicated in table 10 A = -CH2- CH2-; B = OCH3 Table 18:, X, Y and Z as indicated in Table 10 A = -CH2-CH2-; B = OC2H5 The preferred meanings of the groups indicated above in relation to the compounds improving the compatibility with the crop plants ("herbicides-protectors") of the formulas (lia), (Ilb), (lie), (lid) and (lie) are defined below, preferably m means the numbers 0, 1, 2, 3 or 4. Preferably,
means one of the heterocyclic, divalent groupings, schematized below
Preferably, it means the numbers 0, 1, 2, 3 or 4. Preferably, it means methylene or ethylene, respectively substituted, if appropriate, by methyl, by ethyl, by methoxycarbonyl, by ethoxycarbonyl or by alkyloxycarbonyl. Preferably, it means 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 diethyl-amino. Preferably, it means 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. Preferably, it means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine, by chlorine and / or by bromine. Preferably, it means 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, respectively substituted, respectively, by fluorine and / or by chlorine, or means substituted phenyl, optionally by fluorine, by chlorine, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl. Preferably, it means hydrogen, means 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, respectively substituted, by fluorine and / or chlorine, or phenyl, substituted, if appropriate, by fluorine, by chlorine, by methyl, by ethyl, by n- or i- propyl, by n-, i-, s- or t-butyl, or together with R17
means one of the residues -CH2-O-CH2-CH2- and -CH2-CH2-O-CH2-CH2-which are substituted, if appropriate, by methyl, ethyl, furyl, phenyl, a benzene ring, or by two substituents which form, together with the carbon atom, with which they are bonded, a carbocycle with or 6 members. Preferably, it means hydrogen, cyano, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, respectively substituted, by fluorine, by chlorine and / or by bromine. Preferably, it means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, respectively substituted, if appropriate by hydroxy, by cyano, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy. Preferably, it means hydrogen, cyano, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, substituted respectively, where appropriate, fluorine, chlorine and / or bromine. Preferably, it means nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl,
n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluoride-chloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. Preferably, X2 means hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, Fluorichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. Preferably, X3 means hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, Fluorichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. Preferably, t means a number 0, 1, 2, 3 or 4. Preferably, v means a number 0, 1, 2, 3 or 4. Preferably, R22 means hydrogen, methyl, ethyl, n- or i-propyl. Preferably,
R23 means hydrogen, methyl, ethyl, n- or i-propyl. Preferably, R24 means 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- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i- propylamino, n-, i-, s- or t- butylamino, dimethylamino or diethylamino, respectively substituted, if appropriate, by cyano, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy, or by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino, each substituted, where appropriate, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or by -propyl. Preferably, R 25 denotes hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, or s-butyl, respectively substituted, if appropriate, by cyano, hydroxy, fluorine, chlorine, methoxy, by ethoxy, by n- or i-propoxy, means propenyl, butenyl, propynyl or butynyl, respectively substituted, by cyano, by fluorine, by chlorine or by bromine, or by cyclopropyl, cyclobutyl,
cyclopentyl or cyclohexyl, respectively substituted, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl. Preferably, it means hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted, respectively, by cyano, by hydroxy, by fluorine, by chlorine, by methoxy, by ethoxy, by n- or i-propoxy, means propenyl, butenyl, propynyl or butynyl, respectively substituted, by cyano, by fluorine, by chlorine or by bromine, means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, respectively substituted, given, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl or by substituted phenyl, if appropriate, by nitro, by cyano, by fluorine, by chlorine, by bromine , by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by difluoromethoxy or by trifluoromethoxy, or together with R25 means butane-1,4-diyl (trimethylene), pentane-1,5-diyl, 1-oxa-butane-1, -diyl or 3-oxa-pentane-1, 5-diyl, substituted respectively if necessary, by methyl or ethyl. Preferably, it means nitro, cyano, 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. Preferably, X5 means nitro, cyano, 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. In the table 19, following, examples of very particularly preferred compounds have been given as protective agents against the herbicides, according to the invention, of the formula (lia). Table 19: Examples of compounds of the formula (lia)
Examples of compounds of the formula (Ilb) which are very particularly preferred for the herbicide protectants according to the invention have been indicated in Table 20 below.
Table 20: Examples of compounds of the formula (Ilb)
Examples of compounds of formula (I) which are very particularly preferred for the herbicide protectants according to the invention have been indicated in Table 21 below. OR
° R "< II = &Rt; R18
Table 21: Examples of compounds of the formula (lie)
Examples of compounds of the formula (lid) which are very particularly preferred for the herbicide protectants according to the invention have been indicated in Table 22 below.
Table 22: Examples of compounds of the formula (lid)
In the following table 23, examples of compounds of the formula (I) which are very particularly preferred for the herbicide protection according to
the invention.
Table 23: Examples of compounds of the formula (He)
Compounds of compatibility with the crop plants [component (b ')] are most preferred, Cloquintocet-mexyl, Fenchlorazol-ethyl, Isoxadifen-ethyl, Mefenpyr-diethyl, Furilazole, Fenchlorim, Cumyluron, Dymron, Dimepiperate and compounds IIe-5 and IIe-11, especially Cloquintocet-mexyl and Mefenpyr-diethyl, and also particularly preferably Isoxadifen-ethyl. The compounds to be used as protectants of the general formula (lia) are known and / or can be prepared according to known processes (see publications WO-A-91/07874, WO-A-95 / 07897). The compounds, to be used as protectants, of the general formula (Ilb) are known and / or can be prepared according to known processes (cf. EP-A-191736). The compounds to be used as protectants of the general formula (Lie) are known and / or can be prepared according to known processes (see DE-A-2218097, DE-A-2350547). The compounds, to be used as protectants, of the general formula (lid) are known and / or can be prepared according to known processes (see publications DE-A-19621522 / US-A-6235680). The compounds, to be used as protectors, of
the general formula (He) are known and / or can be prepared according to known processes (see publications WO-A-99/66795 / US-A-6 251827). Examples of selective herbicidal combinations according to the invention, constituted respectively by an active product of the formula (I) and, respectively, one of the protectors defined above, have been given in Table 24 below. Table 24: Examples of combinations according to the invention
It has now been found, surprisingly, that the combinations of active products, defined above, constituted by substituted cyclic ketoenols of the general formula (I) and by protectors (antidotes) constituted by the group (b '), indicated above, present an activity Especially good herbicide with a very good compatibility for the crop plants and that can be used diverse crops, especially in cereals, (especially in wheat) as well as in soybeans, potatoes, corn and rice for the selective fight against weeds. In this case it should be considered as surprising that, between a plurality of protectors or known antidotes, which are capable of antagonizing the harmful effect of a herbicide on the crop plants, precisely those
The abovementioned compounds of group (b ') are suitable for almost completely eliminating the damaging effect of substituted cyclic ketoenols on crop plants., without appreciably affecting the herbicidal activity against weeds in this case. In this case, the particularly advantageous effect of the preferred and more preferred combination components of the group (b ') must be pointed out, especially as regards their harmlessness to cereal plants, such as, for example, wheat, barley and rye, as well as corn and rice, as a crop plant. If, for example, according to process (A), ethyl N- [(4-chloro-2,6-dimethyl) -phenylacetyl] -1-amino-3-methoxy-cyclohexanecarboxylate is used as starting material, the development of the method according to the invention can be represented by means of the following reaction scheme:
If, for example, in accordance with process (B), ethyl 0 - [(2-chloro-6-methyl) -phenylacetyl] -1-hydroxy-3-ethoxy-cyclohexanecarboxylate is used as the starting material, the development of
process according to the invention by means of the following reaction scheme:
If, for example, according to the procedure (Ca), 7-butoxy-3- [(4-chloro-2,6-dimethyl) -phenyl] -1-azaspiro [4, 5] decan-2 is used, 4-dione and pivaloyl chloride as starting materials, the development of the process according to the invention can be represented by means of the following reaction scheme:
If it is used, for example, in accordance with process (C) (variant ß), 7-ethoxy-3- [(2,4-dichloro) -phenyl] -1-oxaspiro- [4,5] -decan- 2,4-dione and acetic anhydride as starting materials, the development of the process according to the invention can be represented by means of the following reaction scheme:
If, for example, according to process (D), 7-methoxy-3- [(2,4-dichloro-6-methyl) -phenyl] -1-azaspiro [4, 5] decan-2 is used, -dione and ethyl chloroformate as starting materials, the development of the process according to the invention can be represented by means of the following reaction scheme:
If, for example, 7-ethoxy-3- [(2,4,6-trimethyl) -phenyl] -1-oxaspiro [4, 5] decan-2, 4- is used in accordance with process (E) dione and the methyl chloromonothioformate as starting materials, the development of the reaction may be represented as follows:
If, for example, according to process (F), 7-butoxy-3- [(2,4,6-trimethyl) -phenyl] -azaspiro [4,5] decan-2,4-dione and the methanesulfonium chloride as starting products, the reaction development can be represented by means of the following reaction scheme:
If, for example, according to process (G), 7-methoxy-3- [(2,4-dichloro-6-methyl) -phenyl] -1-oxaspiro [4,5] decan-2 is used, 4-dione and (2, 2, 2-trifluoroethyl) methanedio-phosphonate chloride as starting products, the reaction sequence can be represented by the following reaction scheme:
If, for example, 7-methoxy-3- [(2, 3, 4, 6-tetramethyl) phenyl] -1-azaspiro [4, 5] decan-2, 4 is used according to process (H). -dione and NaOH as components, the development of the process according to the invention can be represented by means of the following reaction scheme:
If, for example, according to process (I) (variant a), 7-ethoxy-3- [(2, 4, 5-trimethyl) -phenyl] -1-oxaspiro [4, 5] decan- 2,4-dione and ethylisocyanate as starting materials, the reaction can be represented by the following reaction scheme:
If, for example, 7-butoxy-3- [(2, 4, 6-trimethyl) -phenyl] -1-azaspiro [4, 5] decan- is used according to process (I) (variant β) 2, 4-dione and the dimethylcarbamic acid chloride as starting products, the development of the reaction can be represented by means of the following scheme: CH,
The compounds of the formula (II), which are necessary as starting materials for the process (A) according to the invention, are new.
wherein A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above. The acylamino acid esters of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XIV) are acylated
wherein A, B, Q1 and Q2 and R8 have the meaning indicated above, with substituted phenylacetic acid derivatives of the formula (XV)
wherein W, X, Y and Z have the meanings indicated above and
U means a dissociable group, introduced by reagents for the activation of carboxylic acids such as carbonyldiimidazole, carbonyldiimides (such as for example dicyclohexylcarbondiimide), reagents for phosphorylation (such as for example P0C13, BOP-C1), agents for the halogenation, such as for example thionyl chloride, oxalyl chloride, phosgene or chloroformic acid esters, (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J.
Chem. 6, 341-5, 1968) or if acylamino acids of the formula (XVI) are esterified
wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above,
(Chem. Ind. (London) 1568 (1968)). The compounds of the formula (XVI)
where A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, are new. The compounds of the formula (XVI) are obtained, for example, if they are acylated according to Schotten-Baumann (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, page 505), 1-amino-cyclohexane-carboxylic acids of the formula (XVII)
where A, B, Q! and Q2 have the meanings indicated above with substituted phenylacetic acid derivatives of the formula (XV)
wherein U, W, X, Y and Z have the meanings indicated above. The compounds of the formula (XV) are partially known and / or can be prepared according to the methods known from the publications cited at the beginning. The compounds of the formula (XIV) and (XVII) are new and can be prepared according to known procedures (see, for example, the publications Compagnon, Ann. Chim. (Paris) [14] 5, pages 11-22, 23-27 (1970), L. Munday, J. Chem. Soc. 4372 (1961), JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975)). The new 1-amino-cyclohexane carboxylic acids (XVII) can be obtained, in general, in accordance with the synthesis of Bucherer-Bergs or according to the Strecker synthesis and in this case are obtained, respectively, in the isomeric forms more diverse. As a consequence, they will be referred to, to simplify, as β-isomers, those in which the substituent 3 (O-A-B) and the amino group are in equatorial / axial position or in position
axial / equatorial. The following are referred to, for simplicity, as isomers to those in which the amino group and the substituent 3 (O-A-B) are in the equatorial / equatorial or axial / axial position.
Example: β isomer Example: isomer a (L. unday, J. Chem. Soc. 4372 (1961).) In addition, the starting materials of the formula (II), used in the procedure (A) above
wherein A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above, if nitriles of 1-amino-cyclohexane-carboxylic acid of the formula (XVIII) are reacted
(XVIII)
where A, B, Q! and Q2 have the meanings indicated above, with substituted phenylacetic acid derivatives of the formula (XV)
wherein U, W, X, Y and Z have the meanings indicated above, to give the compounds of the formula (XIX)
wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, and these are then subjected to acidic alcoholysis. The compounds of the formula (XIX) are also new. The compounds of the formula (XVIII) are also novel and can be prepared, for example, as described in EP 595 130.
The compounds of the formula (III) required as starting materials in the process (D) according to the invention
wherein A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above, are new. These can be prepared, in a simple manner, in accordance with procedures known in principle. The compounds of the formula (III) are obtained, for example, if they are acylated (Chem. Reviews 52, 237-416 (1953)) esters of 1-hydroxy-cyclohexanecarboxylic acid of the formula (XX)
where A, B, Q !, Q2 and R8 have the meanings previously
indicated, with substituted phenylacetic acid derivatives of the formula (XV)
wherein U, W, X, Y and Z have the meanings indicated above. The l-hydroxy-3-alkoxy-cyclohexylcarboxylic acid esters of the formula (XX) are new. These are obtained, for example, if 1-hydroxy-3-alkoxy-cyclohexanecarboxylic acid nitriles are reacted in the presence of acids, for example in accordance with Pinner with alcohols.
The cyanohydrin is obtained, for example, by reaction of substituted 3-alkoxy-cyclohexanolones with cyanuric acid. The acid halides of the formula (IV), the anhydrides of the carboxylic acids of the formula (V), the chloroformic acid esters or the thioesters of the chloroformic acid of the formula (VI), the esters of the chloromonothioformic acid or the esters of the chlorodithioformic acid of the formula (VIII), the sulfonyl chlorides of the formula (VIII), the phosphorus compounds of the formula (IX) and the metal hydroxides, the metal oxides or the amines of the
formula (X) and (XI) and the isocyanates of the formula (XII) and the carbamic acid chlorides of the formula (XIII) furthermore necessary as starting materials for carrying out the processes (C), (D) , (E), (F), (G), (H) and (I) according to the invention, are known compounds in general organic chemistry or inorganic chemistry. The compounds of the formula (XV) are also known from the patent applications mentioned at the beginning and / or can be prepared according to the methods indicated therein. The process (A) is characterized in that they are subjected to an intramolecular condensation to the compounds of the formula (II), in which A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base. Suitable diluents in the process (A) according to the invention are all organic solvents which are inert to the reaction partners. Preferably hydrocarbons, such as toluene and xylene, can be used, as well as ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition to polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide. and N-methyl-pyrrolidone, as well as alcohols such as methanol, ethanol, propanol,
iso-propanol, butanol, iso-butanol and tert-butanol. As bases (agents for deprotonation), all the usual proton acceptors can be used in carrying out the process (A) according to the invention. Preferably, the oxides, hydroxides and carbonates of the alkali metals and alkaline earth metals can be used, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, carbonate. of potassium and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl chloride (with 8 to 10 carbon atoms ) ammonium) or TDA 1 (= tris- (methoxyethoxyethyl) -amine). In addition, alkali metals such as sodium or potassium can be used. Furthermore, the amides and hydrides of the alkali metals and alkaline earth metals, such as sodium amide, sodium hydride and calcium hydride, and also, also, the alkali metal alcoholates, such as sodium methylate, sodium ethylate and tere. -butyrate of potassium. The temperature of the reaction in carrying out the process (A) according to the invention can vary
within broad limits. In general, work is carried out at temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C. The process (A) is carried out, in general, under normal pressure. In carrying out the process (A), according to the invention, the reaction components of the formula (II) and the deprotonating bases are used, in general, in equimolar amounts up to approximately twice equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles). Process (B) is characterized in that the compounds of the formula (III) are condensed intramolecularly, wherein A, B, Q1, Q2,, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base. Suitable diluents for use in process (B) according to the invention are all organic solvents, inert, against the reaction partners. Preferably hydrocarbons, such as toluene and xylene, can be used, in addition, ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, in addition polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
In addition, alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tere can be used. -butanol. As bases (agents for deprotonation), all the usual proton acceptors can be used in carrying out the process (B) according to the invention. Preference is given to using oxides, hydroxides and carbonates of the alkali metals and alkaline earth metals, such as "sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate. and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltrialkyl chloride (with 8 to 10 carbon atoms) Ammonium) or TDA 1 (= tris- (methoxyethoxyethyl) -amine) In addition, alkali metals such as sodium or potassium can be used, and amides and hydrides of alkali metals and alkaline earth metals, such as the amide of sodium, sodium hydride and calcium hydride, and in addition, also, alkali metal alcoholates, such as sodium methylate, sodium ethylate and tere.-potassium butyrate The temperature of the reaction in carrying out the process (B), according to the invention, can be
vary within wide limits. In general, work is carried out at temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C. The process (B) is carried out, in general, under normal pressure. In carrying out the process (B) according to the invention, the reaction components of the formula (III) and the deprotonating bases are used, in general, in equimolar amounts up to approximately twice equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles). The process (Ca) is characterized in that compounds of the formulas (Ila) to (? -2-a) are reacted, respectively, with carbonyl halides of the formula (IV), if appropriate in the presence of a diluent and, in case given, in the presence of an acid-accepting agent. Suitable diluents in the process (Ca) according to the invention are all solvents which are inert towards the acid halides. Preferably, hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, can be used, in addition halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and
o-dichlorobenzene, furthermore ketones, such as acetone and methylisopropyl ketone, in addition ethers, such as diethyl ether, tetrahydrofuran and dioxane, in addition to carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents such as dimethylformamide, dimethylsulfoxide and sulfolane. When the stability to the hydrolysis of the acid halide allows it, the reaction can be carried out, also, in the presence of water. Suitable acid-binding agents in the reaction according to the process (Ca) of the invention are all customary acid acceptors. Preference is given to tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig bases and N, N-dimethyl-aniline, as well as metal oxides. alkaline earth metals, such as magnesium oxide and calcium oxide, further 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 temperature of the reaction in the process (Ca) according to the invention can vary within wide
limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C. When carrying out the process (Ca) according to the invention, the starting materials of the formulas (Ila) to (α -2-a) and the carbonyl halide of the formula (IV) are used in general, respectively, in approximately equivalent amounts. However, it is also possible to use the carbonyl halide in a larger excess (up to 5 moles). The processing is carried out according to usual methods. The process (? ß) is characterized in that the compounds of the formulas (Ila) to (1-2-a) respectively are reacted with carboxylic acid anhydrides of the formula (V), if appropriate, in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. Diluents which can be used in the process (ß ß) according to the invention are preferably those diluents which also come into consideration when the acid halides are used. Otherwise, an excess of the carboxylic acid anhydride can act simultaneously as a diluent. As acid-binding agents, optionally added, preferably in the process (Cfl) are those acid-binding agents which
they also come into consideration preferably when the acid halides are used. The temperature of the reaction in the process (ß) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C. When carrying out the process (ß) according to the invention, the starting materials of the formulas (Ila) up to (α -2-a) and the carboxylic acid anhydride of the formula (V) are used, in general, in approximately equivalent amounts. However, it is possible to use the carboxylic acid anhydride in a larger excess (up to 5 moles). The processing is carried out according to usual methods. In general, the diluents and the carboxylic acid anhydride present in the excess, as well as the carboxylic acids formed, are removed by distillation or by washing with an organic solvent or with water. Process (D) is characterized in that the compounds of formulas (Ila) to (1-2-a) are reacted, respectively, with esters of chloroformic acid or with thioesters of chloroformic acid of formula (VI), in case given, in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent.
Suitable acid-binding agents in process (D) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig and N, -dimethyl-aniline bases, as well as alkaline earth metal oxides, such as magnesium oxide and calcium oxide, furthermore 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. Suitable diluents in the process (D) according to the invention are all solvents which are inert to the esters of chloroformic acid or to thiolesters of chloroformic acid. Preferably, hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, can be used, in addition halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene; ketones, such as acetone and methylisopropyl ketone, in addition ethers, such as diethyl ether, tetrahydrofuran and dioxane, further esters of carboxylic acids, such as ethyl acetate, in addition nitriles such as acetonitrile and also strongly polar solvents, such as dimethylformamide, the
dimethyl sulfoxide and sulfolane. The temperature of the reaction in carrying out the process (D) according to the invention can vary within wide limits. The reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C. The process (D) according to the invention is carried out, in general, under normal pressure. When carrying out the process (D) according to the invention, the starting compounds of the formulas (Ila) to (? -2-a) and the corresponding ester of the chloroformic acid or the thiolester of the chloroformic acid of the formula are used (VI), in general, respectively in approximately equivalent quantities. However, it is also possible to use one or other of the components in a larger excess (up to 2 moles). The processing is carried out according to usual methods. In general, the process is carried out in such a way that the precipitated salts are eliminated and the remaining reaction mixture is concentrated by evaporation by eliminating the diluent. The process (E) according to the invention is characterized in that the compounds of the formulas (Ila) are reacted to (? -2-a) respectively with compounds of the formula (VII) in the presence of a diluent and, if given, in the presence of an acid-accepting agent.
In the preparation process (E), one mole of the starting compound of the formulas (Ila) to (? -2-a) is reacted with about 1 mole of the chloromonothioformic acid ester or the chlorodithioformic acid ester of the formula (VII) at 0 to 120 ° C, preferably at 20 to 60 ° C. Suitable diluents, optionally added, are all polar, inert organic solvents, such as ethers, amides, sulfones, sulfoxides, as well as haloalkanes. Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate or methylene chloride. If, in a preferred embodiment, the enolate salt of the compounds (Ila) is prepared up to (? -2-a) by the addition of strong deprotonating agents, for example sodium hydride or tertiary butylate of potassium, the addition of acid-binding agents may be abandoned. In process (E), all customary proton acceptors can be used as bases. Preferably, the hydrides of the alkali metals, the alkali metal alcoholates, the carbonates or the bicarbonates of alkali metals or alkaline earth metals or nitrogenous bases can be used. By way of
exemplifying examples are sodium hydride, sodium methanolate, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane. (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU). The reaction can be carried out at normal pressure or under high pressure, preferably it will be worked at normal pressure. The processing is carried out according to usual methods. The process (F) according to the invention is characterized in that the compounds of the formulas (Ila) are reacted to (? -2-a) respectively with sulfonyl chlorides of the formula (VIII), if appropriate, in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent. In the preparation process (F), about 1 mole of sulfonyl chloride of the formula (VIII) is reacted, per mole of the starting compound of the formula (Ila) to (? -2-a), to -20 to 150 ° C, preferably at 0 to 70 ° C. The process (F) is preferably carried out in the presence of a diluent. Suitable diluents are all polar, inert, organic solvents, such as
ethers, amides, ketones, esters of carboxylic acid, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride. Preference is given to using dimethylsulfoxide, tetrahydrofuran, dimethylformamide, methyl acetate, methylene chloride. If, in a preferred embodiment, the enolate salt of the compounds (Ila) is reacted to (? -2-a) by the addition of strong deprotonating agents (such as, for example, sodium hydride or potassium tertiary butylate) can be desisted from the addition of acid-binding agents When acid-binding agents are used, the usual inorganic or organic bases will be considered, and sodium hydroxide, carbonate of sodium carbonate, can be indicated in an exemplary manner. Sodium, potassium carbonate, pyridine and triethylamine The reaction can be carried out at normal pressure or under high pressure, preferably at normal pressure.The preparation is carried out according to usual methods. ) according to the invention is characterized in that compounds of the formulas (Ila) to (? -2-a) are reacted respectively with phosphorus compounds of the formula (IX), if necessary, in the presence of
a diluent and, if appropriate, in the presence of an acid-accepting agent. In the preparation process (G), for the preparation of the compounds of the formulas (Ile) to (? -2-e), they are reacted by 1 mole of the compounds (Ila) up to (1-2-a) , with 1 to 2, preferably with 1 to 1.3 moles of the phosphorus compound of the formula (IX) at temperatures between -40 ° C and 150 ° C, preferably between -10 and 110 ° C. The process (G) is preferably carried out in the presence of a diluent. Suitable diluents are all polar, inert organic solvents, such as ethers, esters of carboxylic acids, halogenated hydrocarbons, ketones, amides, nitriles, sulphones, sulfoxides, etc. Preference is given to using acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methyl chloride. Suitable acid-binding agents, optionally added if appropriate are inorganic or organic bases such as hydroxides, carbonates or amines. Exemplary, for example, are sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine. The reaction can be carried out at normal pressure or at
high pressure, preferably work at normal pressure. The elaboration is carried out in accordance with usual methods of organic chemistry. The final products are preferably purified by crystallization, chromatographic purification or by means of so-called "initial distillation", ie removal of the volatile components under vacuum. The process (H) is characterized in that compounds of the formulas (Ila) to (? -2-a) are reacted respectively with metal hydroxides or with metal alkoxides of the formula (X) or with amines of the formula (XI) , if necessary in the presence of a diluent. Suitable diluents in process (H) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol as well as water. The process (H) according to the invention is carried out, generally, at normal pressure. The temperature of the reaction is, in general, between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C. The process (I), according to the invention, is characterized in that the compounds of the formulas (Ila) are reacted to (? -2-a) respectively with (the) compounds of the formula (XII), if appropriate , in the presence of
a diluent and, if appropriate, in the presence of a catalyst or with (ß ß) compounds of the formula (XIII), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent. In the preparation process (a), about 1 mole of isocyanate of the formula (XII) is reacted at 0 to 100 ° C per mole of the starting compound of the formulas (Ila) to (? -2-a). , preferably at 20 to 50 ° C. The process (a) is preferably carried out in the presence of a diluent. Suitable diluents are all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulphones or sulfoxides. If necessary, catalysts can be added to accelerate the reaction. As organic catalysts, tin organic compounds, such as, for example, dibutyltin dilaurate, can be used very advantageously. Preferably work at normal pressure. In the preparation process ([beta]), per mole of the starting compound of the formulas (Ila) to (1-2-a), about 1 mole of carbamic acid chloride of the formula (XIII) is used at 0 to 150 ° C, preferably at 20 to 70 ° C.
Suitable diluents, optionally added, are all polar, inert organic solvents, such as ethers, esters of carboxylic acids, nitriles, ketones, amides, sulfones, sulfoxides or halogenated hydrocarbons. Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride. If, in a preferred embodiment, the enolate salt of the compounds (Ila) is prepared up to (? -2-a) by the addition of strong deprotonating agents (such as, for example, sodium hydride or potassium tertiary butylate) may be desisted from the complementary addition of acid-binding agents. When using acid acceptors, the usual inorganic or organic bases will be used, for example, sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
The reaction can be carried out at normal pressure or elevated pressure, preferably it will be worked at normal pressure. The processing is carried out according to usual methods. The active products are suitable, with a good compatibility with the plants and a favorable toxicity for warm-blooded animals, for the fight against
animal pests, preferably against insects, arachnids and nematodes, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the hygiene sector. Preferably they can be used as plant protection agents. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The pests mentioned above belong to the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp. From the order of the Symphyla, for example, Scutigerella immaculata. From the order of the Thysanura, for example, Lepisma saccharina. From the order of the Collembola, for example, Onychiurus armatus. From the order of Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria. From the order of the Blattaria, for example, Blatta
orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica. From the order of the Dermaptera, for example, Forfícula auricularia. From the order of the Isoptera, for example, Reticulitermes spp. From the order of Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp. From the order of Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis. From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp. From the order of the Lepidoptera, for example,
Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana , Choristoneura fumiferana, Clysia ambiguella, Homona magnanimous, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae. From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon
solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus. From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Typula paludosa, Hylemyia spp. , Liriomyza spp. From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp. From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. ., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp. Plant parasitic nematodes include, for example, Pratylenchus spp., Radopholus
similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp. , Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp. The compounds or combinations of active compounds according to the invention can be used, if appropriate, in certain concentrations or application amounts, also as herbicides. If appropriate, they can also be used as intermediates or as starting materials for the synthesis of other active products. In accordance with the invention, all plants and parts of plants can be treated. By plants, all plants and plant populations, such as desired and unwanted wild plants (including crop plants of natural origin), will be understood in this case. The crop plants can be plants that can be obtained by conventional methods of cultivation and optimization or by means of biotechnological and genetic engineering methods, including transgenic plants and including plant varieties that can be protected or not through the right of protection of plant varieties. By parts of the plants should be understood all the parts and aerial and underground organs of the plants, such as buds, leaves, flowers and roots, being able to indicate in an exemplary way leaves, needles,
stems, trunks, flowers, fruit bodies, fruits and seeds as well as roots, tubers and rhizomes. The crops as well as vegetative and generative reproductive material, for example seedlings, tubers, 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 products or the combinations of the active products is carried out directly or by action on the environment, the biotope or the storage enclosure according to the usual treatment methods, for example by dipping, spraying, evaporating, spraying, spreading, brushing and, in the case of the reproduction material, especially in the case of seeds, in addition by coating with one or more layers. The active compounds or combinations of the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, injectable powders, suspensions, powders, dusts, pastes, soluble powders, granules, concentrates. in suspension-emulsion, natural and synthetic materials impregnated with the active product, as well as microencapsulated in polymer materials. These formulations are prepared in known manner, for example by mixing the active ingredients or the
combinations of the active ingredients with extenders, that is to say with liquid solvents, ie liquid solvents and / or solid excipients, optionally with the use of surfactants, that is, emulsifiers and / or dispersants and / or foam generating means. When water is used as an extender, organic solvents may also be used as auxiliary solvents, for example. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as water. Suitable solid excipients are, for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or
diatomaceous earth and molten synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates; Examples of solid excipients for granules are broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as wood sawdust, coconut shells, corn husks and tobacco stems; suitable emulsifiers and / or foamers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, the arylsulfonates, as well as the egg albumin hydrolysates; Dispersants are suitable as dispersants: for example, sulphite lignin liquors and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins can be used. lecithin, and synthetic phospholipids. Other additives can be mineral oils and
vegetables. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes as well as nutrients, may be employed. in traces, such as the salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations contain, in general, between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds, according to the invention, can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order to extend, for example, the spectrum of activity or eliminate the developments. of resistance. In many cases synergistic effects are obtained, that is to say that the activity of the mixture is greater than the activity of the individual components. Examples of suitable mixing components are the following compounds: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampropylfs; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benodanil; Benomyl; Benthiavalicarb-isopropyl;
Benzamacril; Benzamacril-isobutyl; Bilanafos Binapacryl
Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole
Bupirimate; Buthiobate; Butylamine; calcium polysulfide
Capsimycin; Captafol; Captan; Carbendazim; Carboxin
Carpropamid; Carvone; Chinomethionat; Chlobenthiazone
Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate
Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil
Cyproconazole; Cyprodinil; Cyprofuram; Dagger G; Debacarb
Dichlofluanid; Dichlone; Dichlorophen; Diclocymet
Diclomezine; They diclored; Diethofencarb; Difenoconazole
Diflumetorim; Dimethirimol; Dimethomorph; Dimoxystrobin
Diniconazole; Diniconazole-M; Dinocap; Diphenylamine
Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon
Edifenphos; Epoxiconazole; Ethaboxam; Ethyrimol; Etridiazole
Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole
Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil
Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine
Fludioxonil; Flumetover; Flumorph; Fluoromide; Fluoxastrobin
Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide
Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium
Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox
Guazatine; hexachlorobenzene; Hexaconazole; Hymexazole
Imazalil; Imibenconazole; Iminoctadine triacetate
Iminoctadine tris (albesilate); Iodocarb; Ipconazole
Iprobenfos Iprodione; Iprovalicarb; Irumamycin
Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl;
Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil;
Metalaxyl; Metalaxyl-M; Metconazole; Methasulfocarb;
Methfuroxam; Metiram; Methominostrobin; Metsulfovax; ildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen;
Nitothal-isopropyl; Noviflumuron; Nuarimol; Ofurace;
Orysastrobin; Oxadixyl; oxolinic acid; Oxpoconazole;
Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate;
Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; Polyoxorim; Probenazole; Prochloraz;
Procymidone; Propamocarb; Propanosine-sodium; Propiconazole;
Propineb; Proquinazid; Prothioconazole; Pyraclostrobin;
Pyrazophos; Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur;
Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam;
Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole;
Thicyofen; Thifluzamide; Thiophanate-methyl; Thiram; Thioxymid;
Tolclofós-methyl; Tolylfluanid; Triadimefon; Triadimenol;
Triazbutyl; Triazoxide; Tricyclamide; Tricyclazole; Tridemorph; Trifloxystrobin; Triflumizole; Triforine;
Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb;
Ziram; Zoxamide; (2S) -N- [2- [4- [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methyl-sulfonyl) amino] -butanoamide; 1- (1-naphthalenyl) -lH-pyrrole-2, 5-dione; 2, 3, 5, 6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-
4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-l- (4-chlorophenyl) -2- (1 H-1,2, -triazol-1-yl) -cycloheptanol; 1- (2,3-dihydro-2, 2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylic acid methyl ester; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate; Copper oxychloride; copper sulphate; Cufraneb; Cuprous oxide; Mancopper; copper oxine. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, Furancarbonsáure,
Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, sulfate, copper and other copper preparations. Insecticides / acaricides / nematicides: Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, AKD-1022, AKD-3059, AKD-3088,
Alanycarb, Aldicarb, Aldoxycarb, Allethrin, Alpha-Cypermethrin (Alphamethrin), Amidoflumet, aminocarb, Amitraz, Avermectin,
AZ-60541, Azadirachtin, Azamethiphos, Azinphos-methyl,
Azinphos-ethyl, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,
Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculovirus, Beauveria bassiana, Beauveria tenella, Benclothiaz, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin,
Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl, Bromopropylate, Bromfenvinfos (-methyl), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathiophos, Butocarboxim, Butoxycarboxim, Butylpyridaben, Cadusafos, Camphechlor, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA-50439, Chinomethionat, Chlordane, Chlordimeform, Cloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobenzilate, Chloropicrin, Chlorproxyfen, Chlorpyrifos-methyl, Chlorpyrifos (-ethyl), Chlovaporthrin, Chromafenozide, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidin, Clothiazoben, Codlemone, Coumaphos, Cyanofenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyphenothrin (lR-trans isomer), Cyromazine , DDT, Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulfone, Diafenthiuron, Dialiphos, Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dic Rotophos, Dicyclanil, Diflubenzuron, Dimefluthrin,
Dimethoate, Dimethylvinphos, Dinobuton, Dinocap, Dinotefuran, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emamectin, Emamectin-benzoate, Empenthrin (IR isomer), Endosulfan, Entomopthora spp., EPN, Esfenvalerate, Ethiophencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Famphur, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb,
Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil,
Fenvalerate, Fipronil, Flonicamid, Fluacrypyrim, Fluazuron, Flubenzimine, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenerim, Flufenoxuron, Flufenprox, Flumethrin,
Flupyrazophos, Flutenzin (Flufenzine), Fluvalinate, Fonofos, Formetanate, Formothion, Fosmethilan, Fosthiazate, Fubfenprox (Fluproxyfen), Furathiocarb, Gamma-Cyhalothrin, Gamma-HCH, Gossyplure, Grandlure, granulovirus, Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Japonilure, Kadethrin, nuclear polyhedrovirus, Kinoprene,
Lambda-Cyhalothrin, Lindane, Lufenuron, Malathion, Mecarbam, Mesulfenfos, etaldehyd, Metam-sodium, Methacrifos, Methamidophos, Metharhizium anisopliae, etharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metofluthrin, Metolcarb, Methoxyadiazone, Mevinphos, Milbemectin, Milbemycin, KI-245, MON-45700, Monocrotophos, Moxidectin, MTI-800, Naled, NC-104, NC-170, NC-184, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton- methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (cis-, trans-), Petroleum, PH-6045, Phenothrin (IR isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propa phos, Propargite, Propetamphos, Propoxur, Prothiophos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl,
Pyridaphenthion, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Resmethrin, RH-5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen,
Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetrachlorvinphos, Tetradifon, Tetramethrin, Tetramethrin (IR isomer), Tetrasul, Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringiensis, Tolfenpyrad, Tralocythrin, Tralomethrin, Transfluthrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Trichoderma atroviride, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, L-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, the 3-methyl-phenyl propylcarbamate compound (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2, 2, 2-trifluoroethyl) -8-azabicyclo [3.2. 1] octane-3-carbonitrile (CAS-Re g. -Nr. 185982-80-3) and the corresponding 3-endo isomer (CAS-Reg. -Nr 185984-60-5) (see publications WO-96/37494, WO-98/25923), as well as preparations, containing plant extracts with insecticidal activity, nematodes, fungi or viruses. A mixture with other active products is also possible
known, such as herbicides or fertilizers and growth regulators. The active compounds or the active compound combinations according to the invention can also be present, when used as insecticides, in their customary formulations in the trade as well as in the application forms prepared from these formulations in admixture with synergists. The synergists are the compounds by which the effect of active products or combinations of active products is increased, without the added synergist having to be active in itself. The active compound content of the application forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the application forms can be between 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. The application is carried out in a manner adapted to the forms of application. In use against hygiene pests and stored products, the active ingredients or combinations of the active ingredients are characterized by an excellent residual effect on wood and clay as well as good alkali stability on whitewashed substrates.
As already indicated above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plants and plant varieties as well as parts thereof of wild origin or that are obtained by conventional methods of biological cultivation, such as crossing or fusion of protoplasts, are treated. In another preferred embodiment, plants and varieties of transgenic plants, which have been obtained in accordance with genetic engineering methods, are treated in combination with conventional methods (Genetically Modified Organisms) and their parts. The expression "parts" or "parts of plants" or "components of plants" has been previously explained. In accordance with the invention, plants of the plant varieties customary in the market or which are in use are treated with particular preference. Plant varieties are understood as plants with new properties ("characteristics"), which have been cultivated either by conventional culture, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes or genotypes. In accordance with the types of plants or the varieties of the plants, their location and the growth conditions (terrain, climate, period of
vegetation, food) can also be presented by means of the treatment, according to the invention, additive effects ("synergists"). In this way, for example, smaller amounts of application and / or enlargements of the activity spectrum and / or a strengthening of the effect of the products employable according to the invention, a better growth of the plants, greater tolerance to temperatures are possible. high or low, greater tolerance against drought or against the salt content of water or soil, greater floral yield, easier harvesting, acceleration of maturation, higher crop yields, higher quality and / or higher nutritive value of the products collected, greater storage capacity and / or transformation of the products collected, which go beyond the expected effect itself. The plants or varieties of transgenic plants (obtained by genetic engineering) to be treated, preferably in accordance with the invention, belong to all the plants, which have acquired genetic material through modification by genetic engineering, which provide these plants with valuable properties. especially advantageous ("characteristics"). Examples of such properties are better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or salt content of the crop.
water or soil, greater floral yield, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the products harvested, greater storage capacity and / or transformation of the products collected. Other examples, especially noteworthy for such properties are the greater resistance of plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as a greater tolerance of plants against certain active herbicide products. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed, sugar beet, as well as fruit tree plantations (with the fruits apple, pear, citrus fruits and grapes), especially corn, soybeans, potatoes, cotton and rapeseed. As properties ("characteristics"), the greater resistance of plants to insects will be pointed out by means of the toxins generated in plants, especially those generated in plants by the genetic material from Bacillus Thuringiensis (for example by medium of the Cry1A (a), Cry1A (b), Cry1A (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF genes as well as their combinations), (hereinafter referred to as "Bt plants"). As properties ("characteristics"), it should also be noted,
especially, the greater resistance of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexin, elicitors as well as resistance genes and proteins and corresponding expressed toxins. As properties ("characteristics"), in particular, the greater tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, Glyphosate or Phosphinotricin (for example "PAT" gene) must be pointed out. The genes that provide the respective desired properties ("characteristics") may also be present in combinations 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 trademarks YIELD GARD® (for example corn, cotton, soybean), KnockOut® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) and Ne Leaf® (potato). Examples of herbicide tolerant plants include corn varieties, cotton varieties and soybean varieties, which are marketed under the trademarks Roundup Ready® (tolerance against Glyphosate, for example corn, cotton, soybean), Liberty Link® ( tolerance against Phosphinothricin, for example rapeseed), II® (tolerance against imidazolinones) and STS® (tolerance against
sulfonylureas for example corn). As herbicide-resistant plants (conventionally grown in relation to herbicide tolerance), the varieties marketed for the name Clearfield® (eg corn) can also be cited. Obviously these statements are valid also for varieties of plants developed in the future or that are marketed or developed in the future with these genetic properties ("characteristics").
The indicated plants can be treated in a particularly advantageous manner, according to the invention, with the compounds or mixtures of the active compounds according to the invention. The preferred ranges, mentioned above, in the case of active products or mixtures, are also valid for the treatment of these plants. It should be noted in a special way the treatment of the plants with the compounds or with the mixtures indicated especially in the present text. The active compounds or the combinations of the active compounds according to the invention are not only active against plant pests, hygiene and stored products, but also in the field of veterinary medicine against parasites. animals (ectoparasites) such as hard ticks, soft ticks, scabies mites, migratory mites,
flies (suckers and mincers), fly parasitic larvae, lice, hair nits, feathered nits 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 Mallophagida and the suborders of the Amblycerina as well as from the Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .. from the order Diptera and the suborders of Nematocerina and the 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., H ippobosca 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. Of the subclasses of the Acaria (Acarida) and the orders der Metastigmata also the 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 the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., spp Trombicula., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemid ocoptes spp., Cytodites spp., Laminosioptes spp. The active compounds or combinations of the active compounds according to the invention are also suitable for the control of arthropods, which attack animals useful in agriculture such as, for example, example, cows, lambs, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese,
bees, other domestic animals such as, for example, dogs, cats, game birds, aquarium fish as well as so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. Through the fight against these arthropods, cases of death and reductions in productivity (in milk, meat, wool, skins, eggs, honey, etc.) will be avoided, so that by using the active products according to the invention , a more economical and simpler maintenance of the animals is possible. The application of the active compounds or combinations of the active compounds according to the invention is carried out in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, beverages, dragees, granules, pastes, bolis, by means of the procedure through the "feed-through" food, of suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal application in the form, for example of immersion or bathing (Dippen), spray (Spray), surface watering (Pour-on and Spot-on), washing, dusting as well as with the help of Molded bodies containing the active product such as collars, ear tags, markings
for the tail, bands for limbs, halters, marking devices, etc. When they are used for domestic livestock, coral birds, domestic animals etc. the active ingredients or the active compound combinations can be used as formulations (for example powders, emulsions, agents capable of spreading), containing the active ingredients or combinations of the active compounds in amounts of 1 to 80% by weight , directly or after dilution of 100 to 10,000 times or can be used as a chemical bath. Furthermore, it has been found that the active compounds or combinations of the active compounds according to the invention show a high insecticidal effect against insects, which destroy industrial materials. In an implicit and preferable manner - however without limitation - the following insects can be mentioned: beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpine, 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 minutes.
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, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Thysanides, such as Lepisma saccarina. Industrial materials will be understood in the present context as non-living materials, such as, preferably, synthetic materials, glues, glues, paper and cardboard, leather, wood and wood processing products and paints. In a very special way, the materials to be protected against attack by insects are made of wood and wood products. By wood and wood processing products, which can be protected by means of the agents according to the invention or of the mixtures containing them, it should be understood, for example: construction wood, wooden beams, railway sleepers , parts for bridges, ribs for boats, wooden vehicles, boxes, pallets, containers, telephone poles, wooden coverings, wooden windows and doors, wooden plywood, plywood plates, carpentry works or wooden products, which meet
application, in a very general way, at home or in the construction industry. The active compounds or the active compound combinations can be used as such, in the form of concentrates or customary formulations in general, such as powders, granules, solutions, suspensions, emulsions or pastes. Said formulations can be prepared in a manner known per se, for example by mixing the active ingredients or combinations of the active compounds with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixing agent, repellent Water, if appropriate drying and stabilizers against UV and, if necessary, dyes and pigments as well as other processing aids. The insecticidal agents or concentrates to be used for the protection of wood and wood materials contain the active product, according to the invention, in a concentration of 0.0001 to 95% by weight, especially 0.001 to 60. % in weigh. The amounts of the agents or concentrates used depend on the type and origin of the insects and the environment. The optimum application quantities can be determined respectively by means of series of tests prior to the application. In general, however, it is sufficient to employ from 0.0001 to 20% by weight,
preferably from 0.001 to 10% by weight of the active compound, based on the material to be protected. A solvent or a mixture of organochemical solvents and / or a solvent or mixture of organo-chemical, oleaginous or oil-like solvents, which are difficult to volate and / or a solvent or mixture of polar organochemical solvents, is used as solvent and / or diluent. and / or water and, if appropriate, an emulsifier and / or humectant. The organochemical solvents used are preferably oleaginous or oleaginous solvents, with an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C. By way of such water-insoluble, oil-soluble or oleaginous-type solvents which are difficult to volatile, corresponding mineral oils or their aromatic fractions or mixtures of solvents containing mineral oils, preferably benzine for tests, petroleum and / or alkylbenzene, will be used. Advantageously, mineral oils with a boiling range of 170 to 220 ° C, benzine for tests with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatic hydrocarbons with a boiling range of 160 to 280 ° C, terpene oil and the like.
In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C or a high-boiling mixture of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C and / or oil for use are used. spindles and / or monochloronaphthalene, preferably ot-monochloronaphthalene. Organic solvents, which are difficult to volatile, oleaginous or oil-based, with an evaporation index above 35 and with a flame point above 30 ° C, preferably above 45 ° C, can be partially replaced by solvents light or medium volatile organochemicals, with the proviso that the solvent mixture has an evaporation index above 35 and a flame point above 30 ° C, preferably above 45 ° C, and that the insecticidal-fungicidal mixture is soluble or emulsifiable in this mixture of solvents. According to a preferred embodiment, a part of the solvent or mixture of organochemical solvents or a solvent or mixture of aliphatic, polar organochemical solvents will be replaced.
Preferably, aliphatic organochemical solvents containing hydroxyl groups and / or ester groups will be used
and / or ether groups, such as, for example, glycol ethers, esters or the like. As organic-chemical binders, synthetic resins and / or setting drying oils, known per se, dilutable with water and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used, will be used within the scope of the present invention. especially binders consisting of or containing acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indeno-coumaron resin, silicone resin, vegetable drying and / or drying oils and / or physical drying binders based on a natural and / or synthetic resin. The synthetic resin, used as a binder, can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In a complementary manner, colorants, pigments, water-repelling agents, odor correctors and inhibitors or anti-corrosion agents known per se and the like can be used. It is preferred to employ at least one alkyd resin or alkyd resin in the medium or concentrate according to the invention as an organochemical binder.
modified and / or a drying vegetable oil. Preferably, according to the invention, alkyd resins having an oil content greater than 45% by weight, preferably from 50 to 68% by weight, are used. The aforementioned binder can be partially or totally replaced by a fixing agent (mixture) or by a plasticizer (mixture). These additives should avoid volatilization of active products or combinations of active products as well as crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used). The plasticizers are of the chemical class of the esters of phthalic acid such as dibutyl phthalate, dioctyl phthalate or benzyl butyl, phosphoric acid esters, such as tributyl phosphate, adipic acid esters, such as di- ( 2-ethylhexyl), stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerin ethers or high molecular weight glycol ethers, glycerin esters as well as p-toluenesulfonic acid esters. Fixative agents are chemically based on polyvinylalkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone, ethylenebenzophenone. As a solvent or diluent it comes into consideration
especially water, optionally mixed with one or more of the aforementioned solvents or diluents, emulsifier and organochemical dispersants. Especially effective protection of the wood is achieved by impregnation processes on an industrial scale, for example vacuum, double-vacuum or pressure processes. The agents ready for application can optionally contain other insecticides and, if appropriate, one or more fungicides. The insecticides and fungicides mentioned in WO 94/29 268 are preferably used as additional components of the mixture. The compounds mentioned in this document are expressly an integral part of the present application. Particularly preferred mixing components are insecticides, such as Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transyluthrin, Thiacloprid, Methoxyphenoxid and Triflumuron, and fungicides such as Epoxiconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil,
Dichlorfluanid, Tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-
octylisothiazolin-3-one. At the same time, the active compounds or combinations of the active compounds according to the invention can be used for protection against the proliferation of organisms on objects, especially on ship bodies, sieves, networks, constructions, port facilities. and signaling installations, which come into contact with seawater or brackish water. The proliferation of organisms due to sessile Oligochaeten, such as calcareous tubicides as well as due to the bivalves and species of the lepadomorphs group (sea acorns), such as various types of Lepas and Scalpellum or due to types of the group of the balanomorphs ( barnacles), such as Balanus species, or Pollicipes, increase the resistance to friction of ships and leads, as a result of increased energy consumption and also due to frequent dry dock stays, to a clear increase in the costs of exploitation. In addition to the proliferation of organisms due to algae, for example Ectocarpus sp. and Ceramium sp., has a special significance in particular the proliferation of organisms due to sessile groups of entomostráceos, which are grouped under the name of Cirripedia (crustáceos cirrípedos).
It has now been found, surprisingly, that the compounds, according to the invention alone or in
combination with other active products, have an excellent anti-fouling effect (antiproliferation of organisms). By using the compounds, according to the invention alone or in combination with other active products, the use of heavy metals such as, for example, in the sulfides of bis (trialkyltin), tri-n-butyltin laurate, tri-n-butyltin chloride, cuprous oxide (I), triethyltin chloride, tri-n-butyl- (2-phenyl-4-chlorophenoxy) -tin, tributyltin oxide, molybdenum disulfide, antimony oxide, butyl- polymer titanate, phenyl- (bispyridine) -bismuth chloride, tri-n-butyltin fluoride, manganese ethylenebistiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebistiocarbamate, zinc and copper salts of 2-pyridinium-l-oxide, ethylenebistiocarbamate Bisdimethyldithiocarbamoyl zinc, zinc oxide, cuprous ethylene-bisdithiocarbamate (I), copper thiocyanate, copper naphthenate and tributyltin halides or the concetion of these compounds can be decisively reduced. Furthermore, antifouling paints ready for application contain, if necessary, other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active agents. As components of the combination for the agents
antifoulants, according to the invention, are preferably, preferably: algicides such as 2- ere. -butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, Dichlorophen, Diuron, Endothal, Fentinacetat, Isoproturon, Methabenzthiazuron, Oxyfluorfen, Quinoclamine and Terbutryn; fungicides such as S, S-dioxide of benzo [b] thiophenecarboxylic acid cyclohexylamide, Dichlofluanid, Fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, Tolylfluanid and azoles such as Azaconazole, Cyproconazole, Epoxyconazole, Hexaconazole, Metconazole, Propioconazole and Tebuconazole; molluscicides such as Fentinacetat, Metaldehyd, Methiocarb, Niclosamid, Thiodicarb and Trimethacarb; or traditional anti-fouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethyl paratrysulfone, 2- (N, -dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc of 2-pyridinium-l-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachlorophthalonitrile, tetramethylthiouram disulfide and 2, 4,6-trichlorophenyl-maleinimide. The antifouling agents used contain the
active compounds or combinations of the active compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight. Antifouling agents, in accordance with the invention, also usually contain the frequent components, but are not limited thereto, such as, for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973. The antifouling paints contain, in addition to the active ingredients or combinations of the active ingredients, algaecides, fungicides, molluscicides and insecticides, in accordance with the invention, especially binders. Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or form of systems in organic solvents, butadiene / styrene / acrylonitrile rubbers, desiccant oils such as linseed oil, resin esters or resin esters modified in combination with tars or bitumens, asphalt as well as epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and resins vinyl.
If appropriate, the paints also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. In addition, the paints may contain materials such as colophonium to enable controlled release of active products or combinations of active products. The paints may also contain plasticizers, modifying agents that influence the rheological properties as well as other traditional components. Also in self-polishing anti-fouling systems, the compounds according to the invention or the aforementioned mixtures can be incorporated. The active compounds or combinations of the active compounds according to the invention are suitable for combating animal pests, especially insects, arachnids and mites, which occur in enclosed areas, such as, for example, dwellings, manufacturing facilities, offices, cabins of motor vehicles and the like. These can be used to combat these pests in insecticide products for the home. These are active against sensitive and resistant types as well as against all stages of development. These pests belong: of 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, Opiliones phalangium. From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp. From the order of the Chilopoda, for example, Geophilus spp. From the order of the Zygentoma, for example,
Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus. From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa. From the order of the Saltatoria, for example, Acheta domesticus. From the order of the Dermaptera, for example, Forfícula auricularia. From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.
From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp. From the order of the Coleptera, 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, Phthirus pubis. From the order of the Heteroptera, for example, Ciraex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans. The application in the field of domestic insecticides is carried out individually or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active products of other kinds of known insecticides. it is carried out in aerosols, non-pressurized spraying agents, for example sprays by pumping and spraying, automatic fogging devices, foggers, foam generators, gels, products for platelet evaporators for cellulose or plastic evaporators, liquid evaporators, gel and membrane evaporators, fan-driven evaporators, evaporative systems without energy consumption or passive, papers against moths, bags against moths and gels against moths, in the form of granules or powder, in scattable baits or bait stations. The active compounds or combinations of the active compounds according to the invention can also be used as defoliants, desiccants, herbicidal agents and especially as agents for eliminating
weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds or the combinations of the active compounds according to the invention can be used, for example, in the next plants: Dicotyledonous weeds of the following classes: 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, Yosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicotyledonous crops of the classes: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. Weeds monocotyledonous of the kinds: 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 classes: Allium, Ananas, Asparagus, Oats, Hordeum, Oryza, Panicum, Saccharum, Sécale, Sorghum, Triticale, Triticum, Zea. The use of the active compounds or the combinations of the active compounds according to the invention is not, however, limited in any way to these classes, but extends in the same way also to other plants. The active products or the combinations of the active compounds according to the invention are suitable, depending on the concentration, for combating the weeds completely, for example, in industrial and road installations and on roads and squares, with and without tree growth. In the same way, compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee. tea, rubber oil palm, cocoa, berries and hops
on ornamental and sport meadows and on meadows and to selectively control weeds in mono-annual crops. The active compounds or combinations of the active compounds according to the invention show a strong herbicidal activity and a broad spectrum of activity on the ground and on the aerial parts of the plants. They are also suitable to some extent to selectively control monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the pre-emergence procedure and in the post-emergence process. The active compounds or combinations of the active compounds according to the invention can be used in certain concentrations or amounts of application, also for the control of animal pests and against fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates and as starting materials for the synthesis of other active products. The active compounds or the active compound combinations can be converted into the customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, concentrates in
suspension-emulsion, natural and synthetic materials impregnated with the active product, as well as microencapsulated in polymer materials. These formulations are prepared in a known manner, for example by mixing the active compounds or combinations of the active compounds with spreading materials, that is, with liquid solvents and / or solid excipients, if appropriate, using surfactants, is, emulsifiers and / or dispersants and / or foam generating means. When water is used as the sensing material, organic solvents may also be used, for example, as auxiliary solvents. Particularly suitable liquid solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide and
dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and minerals. Synthetics, such as silicic acid, highly dispersed, aluminum oxide and silicates, as solid excipients for granules are considered: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as wood sawdust, coconut shells, corn husks and tobacco stems; suitable emulsifiers and / or foam generators are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates , the arylsulfonates, as well as the egg albumin hydrolysates; Suitable dispersants are: for example, the sulfitic leaching of lignin and methylcellulose. In the formulations, adhesives such as
such as carboxymethylcellulose, natural and synthetic powdered polymers, 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. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes and nutrients in traces, such as the salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95 weight percent of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations also in admixture with known herbicides and / or with products, which improve the compatibility with the crop plants ("protectors") for the control against weeds, ready-to-use preparations or tank mixes being possible. Mixtures are also possible with weed control agents, which contain one or more herbicides and a
protector Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, aminopyralid, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benzcarbazone, Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil (-alyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben,
Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl) ), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron,
Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin,
Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen,
Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl),
Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam , Fluometuron,
Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam,
Flupropacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-butoxypropyl, -methyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium, Glyphosate (-isopropylammonium, Halosafen, Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone, HOK-201, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium ), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, KIH 485, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesosulfurone, Mesotrione, Metamifop, Metamitron, Metazachlor,
Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron,
Oxaziclomefone, Oxyfluorfen, Paraquat, pelargonic acid, Pendimethalin, Pendralin, Penoxsulam, Pentoxazone,
Phenmedipham, Picolinafen, Pinoxaden, Piperophos,
Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor,
Propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, Pyraflufen (-ethyl), Pyrazogyl, Pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, Pyribenzoxim,
Pyributicarb, Pyridate, Pyridatol, Pyriftalid, Pyriminobac (-methyl), pyrithiobac (-sodium), Pyrimisulfan, Quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, simetryn, sulcotrione , Sulfentrazone, Sulfometuron (-methyl), Sulfosate,
Sulfosulfuron, tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, Topramezone, tralkoxydim, triallate,
Triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin, Trifloxysulfuron, triflusulfuron (-methyl), Tritosulfuron and
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, plant nutrients and agents which improve soil structure, is also possible. The active compounds or combinations of the active compounds can be used as such, as their formulations or the use forms prepared therefrom by further, such as ready-to-use solutions, suspensions, emulsions, powders dilutions , pastes and granulates. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active compounds or the combinations of the active compounds according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated into the soil before sowing.
The amount of active product used can vary within a wide range. This depends fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The advantageous effect of the compatibility with the crop plants of the combinations of the active ingredients,
In accordance with the invention, it is marked in a particularly powerful manner with certain concentration ratios. However, the proportions by weight of the active products or can vary, in the combinations of the active products, in a relatively wide range. In general, they correspond to 1 part by weight of the active compound of the formula (I) or its salts, from 0.001 to 1,000 parts by weight, preferably from 0.01 to 100 parts by weight, particularly preferably from 0.05. up to 20 parts by weight of one of the compounds (antidotes / protectants) improved the compatibility with the plants mentioned above in (b '). The combinations of the active compounds, according to the invention, will generally be applied in the form of finished formulations. However, the active products contained in the combinations of the active products can also be applied in individual formulations, that is to say in the form of tank mixtures. For certain purposes of application, especially in the case of the post-emergence procedure, it may be advantageous, furthermore, to include in the formulations, as other additives, mineral or vegetable oils, compatible with the 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 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 watering, spraying, injecting, sprinkling or spreading. The application rates of the combinations of active products, according to the invention, can vary within certain limits; These depend, among other things, on meteorology and terrain factors. In general, the application amounts are between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha, particularly preferably between 0.01 and 0.5 kg per ha. The combinations of active products, according to the invention, can be applied before and after the outbreak of the plants, ie in accordance with the pre-emergence and post-emergence procedure. The protectors, to be used according to the invention, can be used, in accordance with their properties, for the pre-treatment of the seeds of the crop plants (disinfected from the seeds) or applied to the seeds as a step prior to planting or apply
separately, before the herbicide, or applied together with the herbicide before or after the outbreak of the plants. As examples of plants, important crop plants, such as cereals (wheat, barley, rice), corn, soybeans, potatoes, cotton, rapeseed, beet, sugar cane as well as fruit plants (with apple fruits, pear, citrus and grapes), with cereals, maize, soya, potatoes, cotton and rapeseed being particularly noted. Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. Bactericides can be used to protect plants against Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be cited by way of example, but without any limiting character: types of Xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; types of Erwinia, such as, for example, Er inia amylovora;
Pythium types, such as, for example, Pythium ultimum; Phytophthora types, such as, for example, Phytophthora infestans; Pseudoperonospora types, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; types of Plasmopara, such as, for example, Plasmopara viticola; Bremia types, such as, for example, Bremia lactucae; Peronospora types, such as, for example, Peronospora pisi or P. brassicae; Erysiphe types, such as, for example, Erysiphe graminis; Sphaerotheca types, such as, for example, Sphaerotheca fuliginea; Podosphaera types, such as, for example, Podosphaera leucotricha; Venturia types, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, synonym: Helminthosporium); Cochliobolus types, such as, for example, Cochliobolus sativus (conidia form: Drechslera, synonym: Helminthosporium); types of Uromyces, such as, for example, Uromyces
appendiculatus; Puccinia types, such as, for example, Puccinia recondita; Sclerotinia types, such as, for example, Sclerotinia sclerotiorum; Tilletia types, such as, for example, Tilletia caries; Ustilago types, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia types, such as, for example, Pellicularia sasakii; Pyricularia types, such as, for example, Pyricularia oryzae; Fusarium types, such as, for example, Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of Leptosphaeria, such as, for example, Leptosphaeria nodorum; Cercospora types, such as, for example, Cercospora canescens; Alternaria types, such as, for example, Alternaria brassicae; Pseudocercosporella types, such as, for example, Pseudocercosporella herpotrichoides. The active compounds according to the invention also have a potent reinforcing effect on the plants.
These are suitable, therefore, to mobilize the resistance forces of plants against the attack of undesirable microorganisms. In the present context, plant reinforcing products (resistance inducers) will be understood to be those substances which are capable of stimulating the immune system of plants in such a way that, the treated plants develop a broad resistance against microorganisms when a further inoculation with these undesirable microorganisms. It should be understood by undesirable microorganisms, in the present case, phytopathogenic fungi, bacteria and viruses. The products according to the invention can be used, therefore, to generate resistance in the plants, within a certain period of time from the treatment, against the attack due to the aforementioned pathogens. The time lapse, within which resistance is caused, extends, in general, from 1 to 10 days, preferably from 1 to 7 days from the treatment of the plants with the active products. The good compatibility with the plants and the active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil.
The active compounds according to the invention are also suitable for increasing the yield of crops. It also has a low toxicity and have good compatibility with plants. The active compounds according to the invention can be used, if appropriate, in certain concentrations and amounts of application, also as herbicides, to influence the growth of the plants, as well as for the control of animal pests. These can also be used, if appropriate, as intermediates and as starting materials for the synthesis of other active products. The products according to the invention can be used in the protection of industrial materials against attack and destruction due to undesirable microorganisms. Industrial materials in the present context will be understood as non-living materials, which have been prepared for use in the art. By way of example, the technical materials, which would be protected against microbial modifications or destructions by means of the active products according to the invention, are glues, glues, paper and cardboard, textiles, leather, wood, paints and articles of synthetic material. , cold lubricants and other materials. In the field of materials to be protected, mention may be made of
also parts of production facilities, for example closed cooling water circuits, which may be adversely affected by the multiplication of microorganisms. Within the scope of the present invention, it is preferable to mention adhesives, glues, paper and paperboard, leather, wood, paints, cold lubricants and heat transfer liquids, especially wood. As microorganisms, which can cause the decomposition or modification of technical materials, examples of bacteria, fungi, yeasts, algae and mucilaginous organisms can be cited. Preferably, the active compounds according to the invention act against fungi, especially against molds, fungi coloring and destroying the wood (Basidiomycetes) as well as against mucilaginous organisms and algae. By way of example, microorganisms of the following types may be cited: Alternate, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus. The active products can be transformed, depending on their respective physical and / or chemical properties, into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. seeds, as well as formulations of cold fogging and hot in ultra-low volume (ULV).
These formulations are prepared in a known manner, for example by mixing the active ingredients with spreading agents, that is to say liquid solvents, liquefied gases, which are under pressure and / or solid support materials, optionally with the use of surfactants, that is, emulsifiers and / or dispersants and / or foam generating agents. When the water is used as a sensing agent, organic solvents may also be used, for example, as auxiliary solvents. Suitable liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or
chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, as well as ethers and the asters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as water. By "spreading agents" or liquefied gaseous support materials are meant those which are gaseous at normal temperature and under normal pressure, for example propellant gases for aerosol, such as halogenated hydrocarbons as well as butane, propane, nitrogen and dioxide of carbon. Suitable solid support materials are, for example, natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic mineral flours, such as highly dispersed silicic acid, aluminum oxide and silicates. Suitable solid support materials for granules are, for example, broken minerals and fractions such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules, formed from flours.
inorganic and organic as well as granules made from organic material such as wood sawdust, coconut shell shells, corn ears and tobacco stems. Suitable emulsifying and / or foam generating agents are, for example, nonionic and anionic emulsifiers, such as esters of polyoxyethylenated fatty acids, ethers of polyoxyethylenated fatty alcohols, for example alkylaryl polyglycol ether, alkylsulfonates, the alkyl sulphates, the arylsulfonates, as well as the egg albumin hydrolysates. Suitable dispersants are, for example, sulphite lignin bleach and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers that are powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids, such as cephalins and lecithin and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and materials can be used.
Trace nutrients, such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. The formulations generally contain between 0.1 and 95 weight percent active product, preferably between 0.5 and 90%. The active compounds according to the invention can be present as such or in their formulations also in a mixture of known fungicides, bactericides, acaricides, nematicides or insecticides, in order to extend, for example, the spectrum of activity or the development of the resistance . In many cases synergistic effects are obtained, that is to say that the activity of the mixture is greater than the activity of the individual components. Examples of suitable mixing components are the following compounds: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampropylfs; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin;
Benalaxyl; Benodanil; Benomyl; Benthiavalicarb-isopropyl;
Benzamacril; Benzamacril-isobutyl; Bilanafos; Binapacryl;
Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole;
Bupirimate; Buthiobate; Butylamine; calcium polysulfide; Capsimycin; Captafol; Captan; Carbendazim; Carboxin;
Carpropamid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil;
Cyproconazole; Cyprodinil; Cyprofuram; Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet;
Diclomezine; They diclored; Diethofencarb; Difenoconazole; Diflumetorim; Dimethirimol; Dimethomorph; Dimoxystrobin; Diniconazole; Diniconazole-M; Dinocap; Diphenylamine;
Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon; Edifenphos; Epoxiconazole; Ethaboxam; Ethyrimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole; Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumorph; Fluoromide; Fluoxastrobin; Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide; Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazole; Imazalil; Imibenconazole; Iminoctadine triacetate;
Iminoctadine tris (albesyl); Iodocarb; Ipconazole; Iprobenfos; Iprodione; Iprovalicarb; Irumamycin; Isoprothiolane;
Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb; Maneb; eferimzone; Mepanipyrim; epronil; Metalaxyl; Metalaxyl-M; Metconazole; Methasulfocarb; Methfuroxam; Metiram;
Methominostrobin; Metsulfovax; Mildiomycin; Myclobutanil;
Myclozolin; Natamycin; Nicobifen; Nitothal-isopropyl;
Noviflumuron; Nuarimol; Ofurace; Orysastrobin; Oxadixyl; oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin;
Paclobutrazol; Pefurazoate; Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins;
Polyoxorim; Probenazole; Prochloraz; Procymidone; Propamocarb;
Propanosine-sodium; Propiconazole; Propineb; Proquinazid;
Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox;
Pyrimethanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole;
Spiroxamine; Sulfur; Tebuconazole; Tecloftalam; Tecnazene;
Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen;
Thifluzamide; Thiophanate-methyl; Thiram; Thioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutyl; Triazoxide; Tricyclamide; Tricyclazole; Tridemorph;
Trifloxystrobin; Triflumizole; Triforine; Triticonazole;
Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram;
Zoxamide; (2S) -N- [2- [4- [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methylsulfonyl) amino] -butanoamide; 1- (1-naphthalenyl) -lH-pyrrole-2, 5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl) -2- (1 H-1,2,4-triazol-1-yl) -cycloheptanol; 1- (2, 3-dihydro-2, 2-
methyl dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylate; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and preparations, such as the Bordeaux mixture; copper hydroxide; copper naphthenate; Copper oxychloride; copper sulphate; Cufraneb; cuprous oxide; Mancopper; copper oxine. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, AKD-1022, AKD-3059, AKD-3088, Alanycarb, Aldicarb, Aldoxycarb, Allethrin, Allethrin IR isomer, Alpha-Cypermethrin ( Alphamethrin), Amidoflumet, aminocarb, Amitraz, Avermectin, AZ-60541, Azadirachtin, Azamethiphos, Azinphos-methyl, Azinphos-ethyl, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculoviren, Beauveria bassiana, Beauveria tenella, Benclothiaz, Bendiocarb, Benfuracarb, Bensultap,
Benzoximate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Bioperraethrin,
Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl, Bromopropylate, Bromfenvinfos (-methyl), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathiophos, Butocarboxim, Butoxycarboxim, Butylpyridaben, Cadusafos, Camphechlor, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA-50439, Chinomethionat, Chlordane, Chlordimeform, Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobenzilate, Chloropicrin, Chlorproxyfen, Chlorpyrifos-methyl, Chlorpyrifos (-ethyl), Chlovaporthrin, Chromafenozide, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidin, Clothiazoben, Codlemone,
Coumaphos, Cyanofenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyphenothrin (lR-trans isomer), Cyromazine, DDT, Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulfone, Diafenthiuron, Dialiphos , Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimeflurhrin, Dimethoate, Dimethylvinphos, Dinobuton, Dinocap, Dinotefuran, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emamectin, Emamectin-benzoate, Empenthrin (IR isomer), Endosulfan, Entomopthora spp., EPN,
Esfenvalerate, Ethiophencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Famphur, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxacr, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil ,
Fenvalerate, fipronil, Flonicamid, Fluacrypyrim, Fluazuron, flubenzimine, Flubrocythrinate, flucycloxuron, flucythrinate, Flufenerim, flufenoxuron, flufenprox, flumethrin, Flupyrazofos, Flutenzin (Flufenzine), Fluvalinate, fonofos, Formetanate, Formothion, Fosmethilan, fosthiazate, fubfenprox (Fluproxyfen), Furathiocarb, Gamma-cyhalothrin, Gamma-HCH, Gossyplure, Grandlure, granulovirus, Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Japonilure, Kadethrin, Nuclear polyhedrovirus, Kinoprene, Lambda-Cyhalothrin, Lindane, Lufenuron, Malathion, Mecarbam, Mesulfenfos, Metaldehyd, Metam-sodium, Methacrifos, Methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, Methidathion , Methiocarb, Methomyl,
Methoprene, Methoxychlor, Methoxyfenozide, Metofluthrin, Metolcarb, Methoxyadiazone, evinphos, Milbemectin, Milbemycin, MKI-245, MON-45700, Monocrotophos, Moxidectin, MTI-800, Naled, NC-104, NC-170, NC-184, NC- 194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton-methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (cis-, trans-), Petroleum, PH-6045, Phenothrin (lR-trans isomer) ), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pyrimiphos-ethyl, potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiophos , Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl,
Pyridaphenthion, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Resmethrin, RH-5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam,
Terbufos, Tetrachlorvinphos, Tetradifon, Tetramethrin, Tetramethrin (IR isomer), Tetrasul, Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringiensin, Tolfenpyrad, Tralocythrin, Tralomethrin, Transfluthrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Trichoderma atroviride, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2 , 2, 2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS-Reg. -Nr 185982-80-3) and the corresponding 3-endo isomer (CAS-Reg. -Nr. 185984-60-5) (see publication WO-96/37494, WO-98/25923), as well as preparations, containing plant extracts of insecticidal ion, nematodes, fungi or virus. A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators is also possible. In addition, the compounds according to the invention of the formula (I) also exhibit very high antifungal effects.
good ones. They have a very broad spectrum of antifungal activity, especially against dermatophytes and blastomycetes, molds and against diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigae, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species, such as Microsporon canis and Audouinii. The enumeration of these fungi does not represent in any way a limitation of the fungal spectrum to be considered but it has only an orientative character. The active compounds can be used in the form of their formulations or in the application forms prepared therefrom, such as solutions, suspensions, sprayable powders, pastes, soluble powders, powders and granules ready for use. The application is carried out in the usual manner, for example by watering, spraying, dusting, spreading, sprinkling, foaming, brush application, etc. It is also possible to apply the active products according to the ultra-low volume process or to inject the preparation of the active product or the active product itself into the soil. The seeds of the plants can also be treated. When the active compounds according to the invention are used as fungicides, the amounts of application
They can vary within wide limits according to the type of the application. When the parts of the plants are treated, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the application amounts of the active compound are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. In the case of the treatment of the land, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. The production and use of the active ingredients or combinations of the active compounds according to the invention are illustrated by means of the following examples. Examples Example I-1-a-1
** isomer 11: isomer at about 18: 1
They are placed in a three-necked flask, 100 ml, with thermometer and reflux condenser, under argon, 2.2 eq = 1.33 g of tere. 95% potassium butylate (11.3 mmol) in 5 ml of dimethylacetamide. Add, dropwise, at 80 ° C, 2 g of the compound according to Example II-l (5.13 mmol) in 5 ml of dimethylacetamide. Stir for 1 hour at 80 ° C. The reaction mixture is introduced, under stirring, in 100 ml of ice water, it is adjusted to pH 2 with concentrated HC1 and the precipitate is separated by suction filtration. Purification is carried out by column chromatography on silica gel (dichloromethane: ethyl acetate, 5: 3). Yield: 1.8 g (94% of theory) 72 ° C. ** Enriched isomer after purification by column chromatography on silica gel. Analogously to the example (I-1-a-1) and in accordance with the general indications for the preparation, the following compounds of the formula (I-1-a) are prepared
-NMR (400 MHz, dg-DMSO): displacement d in ppm
** Enriched isomer after purification by column chromatography on silica gel. 1)! H-NMR (400 MHz, d6-DMSO): d = 3.55 (m, 1H, CHO), 7.00 (s, 1H, Ar-H).
Example I-1-b-1
isomer ii **
They are placed in a three-neck flask, 100 ml, with thermometer and reflux condenser, under argon, 0.25 g of the compound according to the example Ila-1 in 30 ml of anhydrous ethyl acetate and 0.1 ml. of triethylamine (0.7 mmol). It is catalyzed with 10 mg of Steglich's base and combined, under reflux, with 0.08 ml of isobutyryl chloride in 2 ml of anhydrous ethyl acetate. Stir for 1 hour. The reaction is monitored by thin layer chromatography. The reaction mixture is concentrated by evaporation in vacuo. A purification is then carried out by column chromatography of the residue on silica gel (n-hexane: ethyl acetate 8: 2). Yield: 0.2 g (62.2% of theory) P.f. 153 ° C. ** Enriched isomer after purification by column chromatography on silica gel. Analogously to the example (I-1-b-1) and
In accordance with the general indications for the preparation, the following compounds of the formula (I-1-b) are prepared
*! H-NMR (300 MHz, CDCl 3): displacement d in ppm. ** Isomer enriched after purification by column chromatography or recrystallization.
Example I-1-c-1
A 100 ml three-necked flask with a thermometer and reflux condenser under argon, 0.715 g of the compound according to example Ila-1 in 30 ml of anhydrous dichloromethane and 0.28 ml of triethylamine and combine, at 20 ° C, with 0.22 g (0.002 mole) of ethyl chloroformate in 2 ml of anhydrous dichloromethane. Stir for 1 hour. The reaction mixture is concentrated by evaporation under vacuum. Subsequently, a purification is carried out by column chromatography of the residue on silica gel (n-hexane: ethyl acetate 8: 2). Yield: 0.38 g (44% of theory), P.f. 181 ° C. ** Enriched isomer after purification by column chromatography on silica gel. Analogously to that of the example (I-1-c-1) and in accordance with the general indications for obtaining it,
prepare the compounds of the following formula (I-1-c)
*! H-NMR (400 ???, CD3CN): displacement d in ppm. ** Enriched isomer after purification by means of
column chromatography or by recrystallization. Example I-1-c-46
0.214 g of the compound according to Example I-l-to-43 (0.6 mmol) are placed in 10 ml of dichloromethane and combined with 0.10 ml of triethylamine (0.72 mmol, 1.2 eq). 0.09 ml of O-phenyl chloroformate (0.66 mmol, 1.1 eq) are added and stirred over the weekend at room temperature. It is combined with 2.5% sodium carbonate solution, then extracted, dried over sodium sulfate and purified by column chromatography with ethyl acetate / n-heptane (3: 7 then 100: 0). 0.084 g (28.4%) of a solid product are obtained (mp .: 192-94 ° C). Analogous to Example I-1-c-46, Example I-1-c-47 with a melting point of 166-168 ° C is obtained.
Example I-1-d-1
0.063 g (0.176 mmol) of the compound according to Example I-l-to-43 are placed in 10 ml of dichloromethane and combined with 0.03 ml of triethylamine. Add 0.02 ml of methanesulfonyl chloride in portions and stir for 24 hours at room temperature. It is combined with a 5% solution of NaHCC > 3, the organic phase is separated and the aqueous phase is extracted with dichloromethane. After drying the combined organic phases with sodium sulphate, the mixture is evaporated to dryness in vacuo and the residue obtained is chromatographed with ethyl acetate / n-heptane (gradient 1/4 then 2/1). Yield: 0.05 g (68% of theory), P.f. 183-184 ° C. Analogously to that of the example (I-1-d-1) and in accordance with the general indications for obtaining it,
prepare the compounds of the following formula (I-1-d)
** Isomer enriched after purification by column chromatography or by recrystallization. Example I-1-f-1
Dissolve 0.143 g of the compound in accordance
with example I-l-to-43 (0.4 mmol) in 8 ml of methanol and combine with 0.39 ml of a 40% methanolic solution of tetrabutylammonium hydroxide (1 eq). After 4 hours at room temperature, the mixture is concentrated by evaporation and the residue formed is discharged three times with methanol. 0.3 g of a highly viscous oil is thus obtained as a product with a quantitative yield. H-NMR (CDCl 3): 3.44 ppm (q, 2H, OCH 2), 2.88 ppm (pseudo-t, 8H, NCH 2) Example I-1-g-1
Dissolve 0.179 g (0.5 mmol) of the compound according to Example Ila-43 in 5 ml of chloroform and combine, at room temperature, with 0.09 g (1.2 eq) of the morpholino-N-carbonyl chloride. as well as with 0.1 ml of triethylamine. Heat for 24 hours under reflux to boiling, then pour over saturated sodium chloride solution. The organic phase is separated and then dried with sodium sulfate. After purification by chromatography on silica gel with a gradient of n-
heptane / ethyl acetate (4: 1 then 1: 4), 140 mg of a solid product are obtained (yield 59%). P.f. ° C: 189-196 ° C Example II-1
(enriched)
They are placed in a three-necked flask, 100 ml, with thermometer and reflux condenser, under argon, 3.8 g of the compound according to example XIV-1 (0.015 mol) in 50 ml of anhydrous tetrahydrofuran and 4, 6 ml of triethylamine and combine, at 0-10 ° C, with 2.95 g (0.01 mole) of mesityleacetic acid chloride in 5 ml of anhydrous tetrahydrofuran. Stir for 1 hour. The reaction mixture is concentrated by evaporation in vacuo. The purification is then carried out by column chromatography of the residue on silica gel (hexane: ethyl acetate 8: 2). Yield: 2.1 g (35% of theory) P.f. 98 ° C. Analogously to the example (II-1) and in accordance with the general indications for obtaining it,
prepare the following compounds of the formula (II)
*! H-NMR (400 MHz, CD3CN): displacement d in ppm. ** Enriched isomer after purification by column chromatography on silica gel. Example XIV-1
They are placed in a three-necked flask, 3,000 ml, with thermometer and reflux condenser, under argon, 120 g (1 eq) of the compound according to example XVII-1 (containing potassium salt) in 1,200 ml of methanol, at 0-5 ° C, and 50 ml of thionyl chloride are added dropwise. It is stirred for 30 minutes at 0 ° C and then for 1 day at 40 ° C. It is refrigerated at 5 ° C, the salt is separated by
filtration by suction and the filtrate is concentrated in vacuum. Yield: 108 g (72% of the theory) viscous syrup passing through two steps from the hydantoin of the formula (XXI). H-NMR (400 MHz, dg-DMSO): d = 0.85-0.90 (m, 3H, CH2CH3), 3.73, 3.76 (2s, 3H, OCH3) ppm. Analogously to the example (XIV-1) and in accordance with the general indications for the preparation, the following compounds of the formula (XIV) are prepared in the form of their hydrochlorides
xHCI
Example XVI1-1
They are placed in a three-necked flask, 3,000 ml, with thermometer and reflux condenser, under argon, 135 g of the compound according to example XXI-1 in 600 ml of 20% KOH. Stir under reflux, under nitrogen atmosphere. Controls are carried out by thin layer chromatography. It is concentrated in the rotary evaporator to approximately 25% of the volume and adjusted, at 0-10 ° C, with concentrated HCl, at pH 4-5. The remaining solution is concentrated by evaporation in vacuo and the residue dried. The total amount was used without characterization
additional, in the synthesis of example XIV-1. The hydantoins of the formula (XXI) are new and can be prepared according to the procedure (J) below. In a manner analogous to that of the example (XVII-1) and in accordance with the general indications for the preparation, the compounds of the formula (XVII) are prepared
Example (? -2-a-l)
0.48 g (2 mmol) of mesityl acid chloride and 0.39 g (2 mmol) of ethyl l-hydroxy-3-n-butoxy-cyclohexyl-carboxylate are heated for 10 hours at 140 ° C. After cooling, 5 ml of DMF are added and 2.4 ml of 1M potassium t-butylate solution (2.4 mmoles) are added dropwise. Stir for 10 hours at room temperature. The solvent is then removed in the rotary evaporator. The residue is partitioned between water and ethyl acetate, the aqueous phase is acidified with 2 N HC1 and the product is extracted with ethyl acetate. The organic phase is dried and concentrated in the rotary evaporator. Yield: 0.10 g (13% of theory) logP 3.57. Analogously to the example (? -2-a-1) and in accordance with the general indications for the preparation, the following compounds of the formula (? -2-a) are prepared
The compounds of the formula (? -2-a) were obtained, as a rule
generally, in the form of a mixture of isomers and separated in the cases marked with) 1 by column chromatography on the cis or trans diastereomers.
Example (? -2-b-l)
0.20 g (0.48 mmol) of the compound according to example I-2-a-32 (cis isomer) and 0.06 g (0.58 mmol) of triethylamine in 20 ml of dichloromethane are placed. Combine, dropwise, with 0.58 ml (0.58 mmol) of a 1M solution of isobutyryl chloride in tetrahydrofuran and stir for 12 hours at room temperature. For the preparation, it is washed with 10% citric acid, 10% sodium hydroxide solution, water, dried and concentrated in a rotary evaporator. The purification is carried out by means of column chromatography (silica gel, dichloromethane / acetone
95: 5). Yield: 0.23 g (98% of theory). logP 5.37
TH-NMR (400 MHz, CD3CN): d = 1.02 (d, 6H, CH (CH3) 2), 3.31 (s, QQ | _ | 3H, OCH3), 3.50 (m, 1H, / \ - ppm.
Analogously to the example (? -2-b-1) and in accordance with the general indications for the preparation, the following compounds of the formula (? -2-b) are prepared
Example (? -2-c-l)
0.20 g (0.48 mmol) of the compound according to Example I-2-a-32 (trans isomer) and 0.06 g (0.58 mmol) of triethylamine are placed in 20 ml of dichloromethane, combine, drop by drop, with 0.58 ml (0.58 mmol) of a 1M solution of isobutyryl chloride in tetrahydrofuran and stir for 12 hours at room temperature. For the preparation, it is washed with 10% citric acid, 10% sodium hydroxide solution, water, dried and concentrated in a rotary evaporator. The additional purification is carried out by means of column chromatography (silica gel, dichloromethane / acetone 95: 5). Yield: 0.20 g (75% of theory). logP 5.21! H-NMR (400 MHz, CD3CN): d = 1.04 (d, 6H, CH (CH3) 2), 3.28 (s, OQ l_ | 3H, OCH3), 3.51 ( m, 1H, / \ -) ppm.
Analogously to that of the example (? -2-c-1) and in accordance with the general indications for the preparation, the following compounds of the formula (? -2-c) are prepared
Process (J) Synthesis of the 7-alkoxy-1,3-diazaspiro- [, 5] -decan-2,4-diones of the formula (XXI) as a starting material of the 1-amino-3-alkoxycyclohexanecarboxylic acids of the formula (XVII)
(XXIV) (XXIII) (XXII) (XXI)
Obtaining 3-methoxycyclohex-2-enone (XXIII-1) variant a)
One 100-liter (0.89 mol) of cyclohexanol, 3-dione, dissolved in 300 ml of methanol, 1,000 ml of toluene and 97.6 ml (0.89 mols) are placed in a three-necked flask of 2 liters. ) of trimethyl orthoformate are combined with 5 g of p-toluenesulfonic acid dihydrate and heated for 2 hours under reflux. After cooling, it is washed at 4 × with 200 ml, each time, of 10% NaOH and the organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. 73.4 g of a light brown oil are obtained, which is used without further purification in the next step. Obtaining 3-propoxycyclohex-2-enone (XXIII-2) variant b)
Two 100-liter (0.89 mol) cyclohexanol, 3-dione, dissolved in 166.6 ml (2.23 mol) of n-propanol and 600 ml of toluene are placed in a 2-liter, three-necked flask. and 97.6 ml (892 mol) of trimethyl orthoformate,
they are combined with 5 g of p-toluenesulfonic acid dihydrate and stirred for 5 hours under reflux in the water separator, until water is no longer separated. The solution is then concentrated under reduced pressure in the rotary evaporator, the residue is taken up in 400 ml of TBE and washed three times with 100 ml of 10% NaOH and with saturated NaCl solution. The organic phase is dried over sodium sulfate and concentrated in the rotary evaporator. A yield of 124.8 g of a yellow oil is obtained, which is used in the next step without further purification. Analogously to that of the examples (XXIII-1) and (XXIII-2) and according to the other procedures described in the literature, the following compounds of the formula (XXIII) are obtained.
(XXIII)
Example XXII-1
122 g (0.791 mole) of 3-propoxycyclohex-2-enone (XXIII-2) are dissolved in 1200 ml of ethyl acetate, combined with 12.2 g of Rh / Al2O3 (5% Rh) and hydrogenated in the autoclave under a hydrogen pressure of 6.5 bar, for 9 hours, at room temperature. The catalyst is filtered off and washed with ethyl acetate and the solution is concentrated on the rotary evaporator. The brown oil, obtained in this way, is distilled in high vacuum. 2 fractions of 47 g (purity 99%) or 47.7 g (purity 78%, containing 21% 3-propoxycyclohexanol-ol as the only impurity) are obtained, which corresponds to a total yield of 68% . Analogously to the example (XXII-1) and in accordance with the indications given in the literature for the hydrogenation of the compounds of the formula (XXIII), the following compounds of the formula (XXII) are obtained.
Example XXI-1
18.4 g (1.1 eq) of NaCN and 154.2 g (4.7 eq) of ammonium carbonate are placed in 612 ml of water. 61.2 g (1 eq) of the compound according to example (XXII-4), dissolved in 612 ml of ethanol, are slowly added dropwise at room temperature. After 16 hours at 55-60 ° C, it is cooled to room temperature and concentrated in the rotary evaporator to dryness. The solid product is stirred in 300 ml of ethanol for 30 minutes. The solution is separated by decantation and the stirring is repeated. The combined ethanolic phases are dried over MgSC > 4, are separated by filtration in a nutcha, concentrated by evaporation in the rotary evaporator.
Yield: 61.4 g (88% of theory). 1 H-NMR (400 MHz, DMSO): 7.70 (bs, 1H); 6.66 (bs, 1H); 3.70-3.76 (m, 0.5H); 3.31-3.43 (m, 2.5H); 1.91-1.99 (m, 0.5H); 1.82-1.88 (m, 0.5H); 1.26-1.75 (bm, 11H); 0.86-0.92 (m, 3H) analogously to the example (XXI-1) and according to the procedures described in the literature for the preparation (for example L. Munday, J.Chem. Soc. 4372 (1961)), the following compounds of the formula (XXI) are obtained.
* The determination of the logP values, indicated in the preceding tables and in the procurement examples, was carried out in accordance with EEC directive 79/831 annex V.A8 by means of HPLC (high resolution liquid chromatography) on a column with inversion of phases (C 18). Temperature:
43 ° C. The determination was carried out in the acid range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents, the linear gradient from 10% acetonitrile to 90% acetonitrile. The determination with the LC-MS in the acid range was carried out at pH 2.7 with 0.1% aqueous formic acid and with acetonityl (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. The determination with the LC-MS in the neutral range was carried out at pH 7.8 with 0.001 molar aqueous solution of ammonium bicarbonate and with acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. The calibration was carried out with unbranched alcan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two alkanones successive). The maximum lambda values were determined by means of the UV spectra from 200 nm to 400 nm at the maximums of the chromatographic signals.
Example A Test with Myzus (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 suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water, containing emulsifier, to the desired concentration. Disc of cabbage leaves of China (Brassica pekinensis), which are strongly attacked by the green leaf louse of the peach tree (Myzus persicae), are sprayed with a preparation of the active product of the desired concentration. After the desired time the destruction is determined in%. In this case 100% means that all the lice on the leaf were destroyed; 0% means that no leaf louse was destroyed. In this trial they show a destruction against Myzus persicae with a value of > 90%, with active compound concentrations of 500 g / ha, the compounds of the preparation examples Ila-1, Ila-2, Ila-6, Ila-7, Ila-8, Ila-9, Ila-10, Ila -12, Ila-14, Ila-15, Ila-16, Ila-17, Ila-18, Ila-19, Ila-20, Ila-21, Ila-22, Ila-24, Ila-25, Ila-26 , Ila-27, Ila-28, Ila-29, Ila-30, 1-1-
a-32, Ila-35, Ila-36, Ila-40, Ila-51, Ila-52,? -2-a-1, I-2-a-2, I-2-a-4, I- 2-a-5, I-2-a-6, I-2-a-7, I-2-a-8, 1-2-a-9, I-2-a-10,? -2- a-ll, I-2-a-12, I-2-a-13, I-2-a-14,? -2-a-15, I-2-a-16, I-2-a- 18, I-2-a-20, I-2-a-21, I-2-a-22,? -2-a-26, I-2-a-27, I-2-a-28, I-2-a-29, I-2-a-31, I-2-a-32,? -2-a-33, I-2-a-34, I-2-a-35, I- 2-a-36, I-2-a-37, I-2-a-39,? -2-a-42, I-2-a-45, I-2-a-46, I-2- a-47, I-2-a-49, I-2-a-50,? -2-a-52, I-2-a-54,? -2-bl, I-2-b-2, I-2-b-3, I-2-b-4, I-2-b-5, I-2-b-6, Ilc-2, Ilc-3,? -2-cl, I-2- C-2, I-2-C-3, I-2-C-4, I-2-C-5 and I-2-C-6. Example B Phaedon Assay (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 suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water, containing emulsifier, to the desired concentration. Leaf discs of Chinese cabbage (Brassica pekinensis) are sprayed with a preparation of the active compound of the desired concentration and, after drying, they are covered with larvae of the horseradish leaf beetle. { Phaedon cochleariae).
After the desired time the destruction is determined in%. In this case 100% means that all the lice on the leaf were destroyed; 0% means that no leaf louse was destroyed. In this trial they show a destruction against Phaedon cochleariae with a value of > 90%, with active compound concentrations of 500 g / ha, the compounds of the preparation examples Ila-1, Ila-2, Ilb-1, Ila-5, Ila-6, Ila-8, Ila-14, Ila -15, Ila-17, Ila-19, Ila-20, Ila-21, Ila-22, Ila-24, Ila-26, Ila-28, Ila-29, Ila-30, Ila-31, Ila-36 , Ila-38, Ila-44, Ila-46, Ila-51, 1-2-a-1, I-2-a-2, I-2-a-12, I-2-a-14, I -2-a-16, I-2-a-17,? -2-a-31, I-2-a-33, I-2-a-42 and? -2-bl. Example C Assay with Spodoptera frugiperda (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 suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water, containing emulsifier, to the desired concentration. Corn leaf discs (Zea mays) are sprayed with a
preparation of the active product of the desired concentration and, after drying, they are covered with larvae of the corn cogollero (Spodoptera frugiperda). After the desired time the destruction is determined in%. In this case 100% means that all the lice on the leaf were destroyed; 0% means that no leaf louse was destroyed. In this trial they show a destruction against Spodoptera frugiperda with a value of > 80%, with active compound concentrations of 500 g / ha, the compounds of the preparation examples Ilc-3, Ila-β, Ila-36, I-2-a-8, α -2-a-ll, 1 -2-a-14, I-2-a-31, I-2-a-32, I-2-b-3 and I-2- C-4. Example D Test with Tetranychus (OP-resistant / 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 suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water, containing emulsifier, to the desired concentration. Bean leaf disks (Phaseolus vulgaris) are sprayed, which are strongly attacked by all
Mite development stages of the common red spider mite. { Tetranychus urticae), with a preparation of the active compound of the desired concentration. After the desired time, the effect in% is determined. In this case they mean 100% that all the spider mites were killed; 0% means that no spider mite was killed. In this test they show a destruction against Tetranychus urticae with a value of > 70%, with active compound concentrations of 100 g / ha, the compounds of the preparation examples Ila-1, Ila-6, Ila-7, Ila-10, Ila-14, Ila-15, Ila-18, Ila -26, Ila-28, Ila-29, Ila-30, 1-1-a-32, Ila-33, Ila-35, Ila-36, Ila-40, Ila-42, Ila-45, Ila-46 , Ila-51, Ila-52,? -2-al, I-2-a-2, I-2-a-16, I-2-a-42,? -2-bl, I-2-b -3, I-2-b-4, I-2-b-5, I-2-b-6,? -2-c-1, I-2-C-2, I-2-C-3 , I-2-C-4, I-2-C-5, I-2-C-6, Ilc-2, 1-1-c-1, Ilc-3, Ila-5 and Ila-4. Example E Limit concentration test / soil insects - treatment of transgenic plants Test insect: Diabrotica bal eata - Larvae on the ground
Solvent: 7 parts by weight acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.
To obtain a convenient preparation of active compound, 1 part by weight of active compound is mixed
with the indicated amount of solvent, add the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration. The preparation of the active product is irrigated on the
terrain. In this case practically no role plays the concentration of the active product in the preparation, what is decisive is only the amount of active product per unit of soil volume, which is indicated in ppm (mg / 1). The soil is loaded in pots of 0.25 liters and these are left
] _Q stand at 20 ° C. Immediately after loading, 5 maize grains of the variety YIELD GUARD (registered trademark of Monsanto Comp., USA) are arranged in each pot. After 2 days, the 5 corresponding test insects are placed in the treated areas. After another 7 days the degree of activity of the active product is determined by counting the developed corn plants (1 plant = 20% activity). Example F 20 Assay with 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 preparation of active compound, 1 part by weight of active compound is mixed
with the indicated amount of solvent and with the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration. Soya bean sprouts (Glycine max) of the Roundup Ready variety (registered trademark of Monsanto Comp.
USA) by immersion in the preparation of the active product of the desired concentration and are covered with the caterpillar of the tobacco bud Heliothis virescens, as long as the leaves are still wet. After the desired time the destruction of the insects is determined. EXAMPLE 6 Herbicidal effect in pre-emergence Weed seeds are sown from either monocotyledonous or dicotyledonous cultivation plants in wood fiber sherds, in sandy mud and covered with soil. The test compounds, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied as an aqueous suspension with an application amount of water of approximately 800 1 / ha with the addition of a 0.2% wetting agent on the surface of the cover soil. After the treatment, the pots are placed in the greenhouse and maintained under good growth conditions for the test plants. The evaluation to simple
View of the growth damage in the test plants is carried out after a test time of 3 weeks compared to untreated controls (herbicidal effect in percentage (%): 100% effect = the plants are destroyed, 0% effect = like the control plants). Post-emergence herbicidal effect Seeds of weeds are grown either from monocotyledonous or dicotyledonous cultivation plants in wood fiber sherds, in sandy mud and covered with soil and cultivated in the greenhouse under good conditions for growth. After 2 to 3 weeks from sowing, the test plants are treated in the one-leaf stage. The test compounds, formulated in the form of wettable powders (WP) or of emulsion concentrates (EC), are sprayed as an aqueous suspension with an application amount of water of approximately 800 1 / ha with the addition of a 0, 2% wetting agent on the green parts of the plants. Approximately after 3 weeks of life time of the test plants in the greenhouse under optimum growth conditions, the effect of the preparations is evaluated with the naked eye compared to the untreated controls (herbicidal effect in percentage (%): 100% effect = the plants are destroyed, 0% effect = like the control plants). The following compounds show in pre-bud with 320
g / ha a. i. against Avena sativa, Lolium multiflorum and Setraia viridis an action with a value of > 80%: I-1-a-12, I-1-a-17, I-1-a-36, I-1-a-63, I-1-a-71. The following compounds show in post-emergence with 320 g / ha a. i. against Avena sativa, Lolium multiflorum and Setaria viridis and Echinochloa an action with a value of > 70%: Ila-1, Ila-12, Ila-14, Ila-17, Ila-18, Ila-36, Ila-40, Ila-47, Ila-66, Ila-67, Ila-63, Ila-71 , 1-1-a-49, Ila-64, Ila-79, Ilb-1, Ilb-26, Ilc-1, Ilc-2, Ilc-3, Ilc-18, I-2-a-3, I -2-a-13. EXAMPLE H Post-emergence herbicidal effect Seeds of weeds are sown either from monocotyledonous or dicotyledonous cultivation plants in wood fiber pots or plastic pots, in sandy mud and covered with soil and cultivated in the greenhouse , during the loss of vegetation also outside, outside the greenhouse, under good conditions of development. After 2 to 3 weeks from sowing, the test plants are treated in the two- to three-leaf stage. The test compounds, formulated as sprayable powders (WP) or as a liquid (EC), are sprayed, in various doses, with an application amount of water of approximately 300 1 / ha with the addition of wetting agent (0.2 bis). , 3%) on the plants and on the surface of the land. The effect of the preparations
it is evaluated, at a glance, after 3 to 4 weeks from the treatment of the test plants compared to the untreated controls (herbicidal effect in percentage (%): effect of 100% = the plants are destroyed, effect of the 0% = like the control plants). Use of protectors When additional testing is necessary, if the protectors can improve the compatibility with the plants of the test substances in the crop plants, the following possibilities will be used for the application of the protector: the seeds of the cultivation plants are disinfected , before sowing, with the protective substance (indications of the amount of protector in percentage with respect to the weight of the seeds), the crop plants are sprayed, before the application of the test substances, with the protector with a amount determined per hectare (usually 1 day before the application of the test substances), the protector is applied, together with the test substance, in the form of a tank mixture (indications of the amount of protector in g / ha or as a relation with respect to the herbicide). By comparing the effect of the test substances on the crop plants, which have
been treated with and without the protector, it can be evaluated in effect of the protective substance. Potted trials with cereals in the greenhouse
Mefenpyr 1 day before the application of the herbicide
Potted trials with corn in the greenhouse Isoxadifen 1 day before the application of the herbicide
Test in pots with cereals in open field Mefenpyr 1 day before the application of the herbicide
Potted trials with cereals in the open field
Mefenpyr in tank mix 50 g / ha
Method: post-emergence tank mix
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 (1)
- 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 W means hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano, X means halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, haloalkyl, haloalkoxy or cyano, and in the 4-position means hydrogen, halogen, alkoxy, cyano, haloalkyl or haloalkoxy, Z means hydrogen, W also means hydrogen, halogen or alkyl, X also means halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, and in the 4-position means , also, phenyl or hetaril If appropriate, Z is hydrogen, W is hydrogen, halogen or alkyl, X is halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, and also in the 5-position means phenyl or substituted hetaryl, if appropriate, Z in the 4-position also means hydrogen, alkyl or halogen, W further denotes hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, cyano or trifluoromethyl, X means, in addition, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, haloalkyl, haloalkoxy or cyano, and in the 4-position means, furthermore, alkyl, Z means, furthermore, hydrogen, W further means hydrogen, halogen, alkyl or alkoxy, X means, in addition, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, and in the 4-position means, furthermore, hydrogen, halogen, alkyl, haloalkyl or haloalkoxy, Z in the 3 or 5 position means in addition, halogen, alkyl, haloalkyl, cyano, alkoxy or halogenoalkoxy, A means an alkanediyl group, optionally substituted or optionally substituted cycloalkyl and / or If the given case is interrupted by a heteroatom, it means hydrogen or alkyl, alkenyl, alkoxy, alkoxy-alkoxy, phenyl, hetaryl respectively substituted, or optionally substituted cycloalkyl, optionally and / or interrupted, if appropriate, by heteroatoms and / or by C = 0, D means NH or oxygen, Q1 means hydrogen, means alkyl, alkoxy, alkoxyalkyl or substituted alkylthioalkyl respectively, optionally, means substituted cycloalkyl, optionally, where appropriate, a methylene group being replaced by heteroatoms or means phenyl, hetaryl, phenylalkyl or hetarylalkyl, optionally substituted, means hydrogen or alkyl, and Q2 signify, together with the carbon, with which they are bonded, a ring with 3 to 6 carbon atoms, optionally substituted, which may be interrupted, if appropriate, by a heteroatom, G means hydrogen (a) or one of the groups wherein E means a metal ion or an ammonium ion, L means oxygen or sulfur, M means oxygen or sulfur, means alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl respectively substituted, if appropriate, by halogen or by cyano or means cycloalkyl or heterocyclyl substituted, where appropriate, by halogen, by alkyl or by alkoxy or means phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, respectively substituted, if appropriate, means alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl substituted respectively, given, by halogen or by cyano or means cycloalkyl, substituted phenyl or benzyl, respectively, and R 5 signify, independently of each other alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio respectively substituted, by halogen or they mean substituted phenyl, benzyl, phenoxy or phenylthio Where appropriate, R7 is independently hydrogen, meaning alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl respectively substituted, if appropriate, by halogen or by cyano, means phenyl or benzyl substituted respectively, if appropriate, or together with the N atom, to which they are bonded, form a cycle, which, if appropriate, contains Oxygen or sulfur and which is substituted, if appropriate, 2. Compounds of the formula (I), according to claim 1, characterized in that W means hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, halogen, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms or cyano, X means halogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkoxy with 1 to 4 carbon atoms carbon, halogen alkyl with 1 to 4 carbons ono, halogenalkoxy with 1 to 4 carbon atoms or cyano, Y means, in the 4-position, hydrogen, halogen, alkoxy with 1 to 6 carbon atoms, cyano, haloalkyl with 1 to 4 carbon atoms or halogenalkoxy 1 to 4 atoms of carbon, Z means hydrogen, also means hydrogen, halogen or alkyl having 1 to 6 carbon atoms, also means halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, also means phenyl or pyridyl substituted in the 4 position by \? and V ^, also denotes hydrogen, also means halogen, alkyl having 1 to 12 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, also means hydrogen, halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, v2 mean, together, also alkanediyl with 3 to 4 carbon atoms, which may be substituted, if appropriate, by halogen and / or by alkyl having 1 to 2 carbon atoms and which may be interrupted by one or two oxygen atoms, means in the same way, hydrogen, halogen or alkyl having 1 to 6 carbon atoms , means in the same way, halogen, alkyl, with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, chalogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, means in the same way, in position 5, phenyl or pyridyl substituted by and V ^, also means, in position 4, hydrogen , alkyl having 1 to 6 carbon atoms or halogen, means in the same way, halogen, alkyl having 1 to 12 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogen with 1 to 4 carbon atoms or halogenoalkoxy with 1 to 4 carbon atoms, means in the same way, hydrogen, halogen, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, v2 mean, together, in the same way , alkanediyl having 3 to 4 carbon atoms, which may be substituted, if appropriate, by halogen and / or by alkyl having 1 to 2 carbon atoms and which may be interrupted, if appropriate, by one or two oxygen atoms , also means hydrogen, alkyl having 1 to 6 carbon atoms arbono, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogen, trifluoromethyl or cyano, furthermore means halogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms carbon, alkoxy with 1 to 6 carbon atoms-alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, means in addition, in the 4-position, alkyl with 1 to 6 carbon atoms, furthermore means hydrogen, also means hydrogen, halogen, alkyl having 1 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms, also means halogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or cyano, also means, in position 4, hydrogen, halogen 0 C 1 -C 6 -alkyl, haloalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, also means, in the 3 or 5 position, halogen, alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, cyano, alkoxy with 1 to 6 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, means an alkanediyl group with 1 to 4 carbon atoms substituted, if appropriate, by alkyl with 1 to 4 carbon atoms or means cycloalkyl with 5 to 8 carbon atoms substituted, if appropriate, by alkyl with 1 to 4 carbon atoms, in which, if appropriate, a methylene group is replaced by oxygen, means hydrogen or means alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 8 carbon atoms, alkoxy with 1 to 6 carbon atoms, · C 1-6 alkoxy-alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-bis-alkoxy with 1 to 4 carbon atoms, respectively substituted, if appropriate , by halogen, means phenyl substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by cyano or by nitro, means pyridyl, pyrimidyl, thiazolyl or thienyl substituted, if appropriate, by halogen, by alkyl with 1 to 4 carbon atoms or by halogenalkyl with 1 to 2 carbon atoms or means cycloalkyl with 3 to 8 carbon atoms substituted, if appropriate, by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkyl with 1 to 2 carbon atoms, in which one or two methylene groups, not directly adjacent, are replaced, in given case, by oxygen, two methylene groups are replaced by the remainder -0-C0- or three methylene groups are replaced by the remainder -0-CO-O-, means NH or oxygen, means hydrogen or means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon-alkyl atoms having 1 to 4 carbon atoms substituted, if appropriate, by halogen or means cycloalkyl having 3 to 6 carbon atoms substituted, if appropriate, by halogen, by alkyl having 1 to 4 carbon atoms or by alkoxy having from 1 to 4 carbon atoms, optionally being replaced by a methylene group by oxygen or by phenyl, phenyl-alkyl having 1 to 2 carbon atoms or hetaryl substituted, respectively, optionally, once or twice by halogen, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms, means hydrogen or alkyl with 1 to 6 Carbon atoms, o and Q2 mean, together with the carbon atom, to which a 3 to 6-membered ring is bonded, optionally substituted one to two times by fluorine, by chlorine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by trifluoromethyl, the methylene group being replaced by oxygen, G means hydrogen (a) or means one of the groups in which E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, R! means alkyl with 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms, alkylthio with 1 to 8 carbon atoms-alkyl with 1 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl having 1 to 8 carbon atoms substituted, if appropriate, by halogen or by cyano or means cycloalkyl with 3 to 8 carbon atoms substituted, given by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms, in which, if appropriate, one or two methylene groups, not directly adjacent, are replaced by oxygen and / or sulfur, means phenyl substituted, if appropriate, by halogen, by cyano, by nitro, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms or alkylsulfonyl having 1 to 6 carbon atoms means phenyl-alkyl having 1 to 6 carbon atoms, substituted, if appropriate, by halogen, by nitro, by cyano, by alkyl having 1 to 6 carbon atoms, C 1 -C 6 alkoxy, halogen alkyl with 1 to 6 carbon atoms or halogenalkoxy with 1 to 6 carbon atoms means 5 or 6-membered heteroaryl substituted, if appropriate by halogen or by alkyl with 1 to 6 carbon atoms, with one or two heteroatoms of the series consisting of oxygen, sulfur and nitrogen, means phenoxy-alkyl having 1 to 6 carbon atoms, optionally substituted by halogen or by alkyl having 1 to 6 carbon atoms or means hetaryloxy with 5 or 6 members-alkyl with 1 to 6 atoms of carbon substituted, if appropriate, by halogen, by amino or by alkyl with 1 to 6 carbon atoms, with one or two heteroatoms of the series consisting of oxygen, sulfur and nitrogen, means alkyl having 1 to 20 carbon atoms, alkenyl with 2 to 20 carbon atoms, alkoxy with 1 to 8 carbon atoms-alkyl having 2 to 8 carbon atoms or poly-alkoxy with 1 to 8 carbon atoms-alkyl having 2 to 8 carbon atoms substituted respectively, given, by halogen or by cyano, means cycloalkyl with 3 to 8 carbon atoms substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms or by alkoxy with 1 to 6 carbon atoms or means phenyl or benzyl replace them, if appropriate, by halogen, cyano, nitro, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms or halogenalkoxy with 1 to 6 carbon atoms, R3 means alkyl with 1 to 8 carbon atoms, substituted, if appropriate, by halogen or means phenyl Or benzyl substituted, if appropriate, by halogen, by alkyl with 1 to 6 carbon atoms, by alkoxy with 1 to 6 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by haloalkoxy with 1 to 4 carbon atoms; carbon, by cyano or by nitro, R4 and R5 mean, independently of each other, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkylamino with 1 to 8 carbon atoms, di- (alkyl with 1 to 8 carbon atoms) amino, alkylthio with 1 to 8 carbon atoms or alkenylthio with 3 to 8 carbon atoms substituted, if appropriate, by halogen or means phenyl, phenoxy or phenylthio substituted, respectively, by halogen, by nitro, by cyano, by alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkyl with 1 to 4 carbon atoms or for halogenalkyl with 1 to 4 carbon atoms, meaning independently of one another, hydrogen, mean alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkenyl with 3 to 8 carbon atoms, carbon or alkoxy with 1 to 8 carbon atoms-alkyl with 2 to 8 carbon atoms substituted, if appropriate, by halogen or by cyano, means phenyl or benzyl substituted, if appropriate, by halogen, by alkyl with 1 to 8 carbon atoms, by halogenoalkyl with 1 to 8 atoms of carbon or by alkoxy with 1 to 8 carbon atoms or together they mean an alkylene radical having 3 to 6 carbon atoms substituted, optionally by alkyl having 1 to 6 carbon atoms, where it is replaced, if appropriate, a methylene group by oxygen or by sulfur. 3. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, means chlorine, bromine , alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or cyano, means, in position 4, hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy, means hydrogen, also means hydrogen, chlorine, bromine or alkyl with 1 to 4 carbon atoms, also means chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms, haloalkoxy with 1 to 2 atom s carbon or cyano, means also, in position 4, the rest also means hydrogen, also means fluorine, chlorine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, also means hydrogen, fluorine, chlorine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkyl with 1 to 2 carbon atoms, v2 mean, together, also -0-CH2-0- or -0-CF2 -0-, means in the same way hydrogen, chlorine, bromine or alkyl with 1 to 4 carbon atoms, means in the same way chlorine, bromine, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 2 carbon atoms, means similarly, in position 5, the rest means in the same way, in the 4-position, hydrogen, alkyl with 1 to 4 carbon atoms or chlorine, means in the same way fluorine, chlorine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, means in the same way hydrogen, fluorine, chlorine, alkyl with 1 to 4 carbon atoms, C 1 -C 4 alkoxy or C 1 -C 2 haloalkyl, v 2 together, mean in the same way -CH 2-0- or -0-CF 2-0-, also means hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, chlorine, bromine or trifluoromethyl, also means chlorine, bromine, alkyl with 1 to 4 carbon atoms, carbon, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, haloalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or cyano, means, in addition, 4, alkyl having 1 to 4 carbon atoms, furthermore means hydrogen, also means hydrogen, chlorine, bromine, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, X also means chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms or cyano, and also means, in position 4, hydrogen, chlorine, bromine, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, Z also means, in position 3 or 5, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms, A means an alkanediyl group with 1 to 3 carbon atoms of carbon substituted, if appropriate, by alkyl having 1 to 2 carbon atoms or means cycloalkyl with 5 to 6 carbon atoms, in which, if appropriate, a methylene group is replaced by oxygen, B means hydrogen or alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms carbon, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkoxy with 1 to 3 carbon atoms, alkoxy with 1 to 4 carbon atoms-bis-alkoxy with 1 to 3 carbon atoms substituted respectively , if appropriate, one to three times fluorine or chlorine, means phenyl substituted, optionally one to three times by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 2 carbon atoms, halogenalkoxy having 1 to 2 carbon atoms, per cyano or per nitro, means pyridyl, pyrimidyl, thiazolyl or thienyl substituted, if appropriate, one to two times by fluorine, chlorine, bromine, methyl, ethyl or by trifluoromethyl or means cycloalkyl with 3 to 6 carbon atoms substituted, optionally one to two times by fluorine, by chlorine, by methyl, by methoxy or by trifluoromethyl, in which they are replaced, if necessary, two methylene groups, not directly adjacent, by oxygen, means NH or oxygen, means hydrogen, means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 2 carbon atoms, carbon-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine, or means cycloalkyl with 3 to 6 carbon atoms, optionally one to two times fluorine, chlorine , by methyl, by ethyl or by methoxy, where a methylene group may be replenished by oxygen, means hydrogen or alkyl with 1 to 4 carbon atoms. carbon, Q2 mean, together with the carbon atom, with which they are bonded, a ring with 3 to 6 members monosubstituted, if necessary, by fluorine, by methyl, by methoxy or by trifluoromethyl, and may be replaced if necessary given a methylene group by oxygen, means hydrogen (a) or means one of the groups HE), in which E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, means alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms -alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms or poly-alkoxy with 1 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms substituted respectively, if appropriate, one to three times fluorine or chlorine or cycloalkyl with 3 to 7 carbon atoms, optionally substituted one to two times by fluorine, by chlorine, by alkyl with 1 to 5 carbon atoms or by alkoxy with 1 to 5 carbon atoms, where appropriate, one or two methylene groups, not directly adjacent, being replaced, if appropriate, by oxygen and / or by sulfur, means phenyl substituted, optionally one to three times by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by haloalkyl with 1 to 3 carbon atoms, by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, means phenyl-alkyl with 1 to 4 carbon atoms substituted, in case given one to two times by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by haloalkoxy with 1 to 3 carbon atoms, means pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thieni The substituted one, optionally one to two times by fluorine, by chlorine, by bromine or by alkyl with 1 to 4 carbon atoms, means phenoxy-alkyl having 1 to 5 carbon atoms, substituted, if appropriate, by one to twice fluorine, chlorine, bromine or alkyl with 1 to 4 atoms carbon or means pyridyloxy-alkyl with 1 to 5 carbon atoms, pyrimidyloxy-alkyl with 1 to 5 carbon atoms or thiazolyloxy-alkyl with 1 to 5 carbon atoms substituted, respectively, one to two times by fluorine, by chlorine, by bromine, by amino or by alkyl with 1 to 4 carbon atoms, means alkyl with 1 to 16 carbon atoms, alkenyl with 2 to 16 carbon atoms, alkoxy with 1 to 6 carbon atoms-alkyl with 2 carbon atoms; with 6 carbon atoms or poly-alkoxy with 1 to 6 carbon atoms-alkyl having 2 to 6 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine, means cycloalkyl with 3 to 7 atoms of carbon substituted, if appropriate, one to two times by fluorine, by chlorine, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms or by phenyl or benzyl respectively substituted, if appropriate, one to three times fluorine, chlorine, bromine, cyano, ni by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 3 carbon atoms, by halogenalkyl with 1 to 3 carbon atoms or by halogenalkoxy with 1 to 3 carbon atoms, means alkyl with 1 to 6 carbon atoms. carbon replaced, if appropriate, one to three times by fluorine 0 per chlorine or means phenyl or benzyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 2 carbon atoms, for halogenalkyl with 1 to 2 carbon atoms, for cyano or for nitro, and R5 mean, independently of each other, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, C 1 -C 6 alkylamino, di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylthio or alkenylthio with 3 to 4 carbon atoms, respectively substituted, if appropriate, three times by fluorine or chlorine or by phenyl, phenoxy or phenylthio respectively substituted, optionally one to two times by fluorine, chlorine, bromine, nitro, cyano, alkoxy with 1 to 3 carbon atoms , by halogenalkoxy with 1 to 3 carbon atoms, by alkylthio with 1 to 3 carbon atoms, halogenalkylthio with 1 to 3 carbon atoms, alkyl with 1 to 3 carbon atoms or halogenalkyl with 1 to 3 carbon atoms, and R7 they mean, independently of each other, hydrogen, they mean alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkenyl with 3 to 6 carbon atoms or alkoxy with 1 to 6 carbon atoms-alkyl having 2 to 6 carbon atoms, respectively substituted, if appropriate, one to three times by fluorine or chlorine, means phenyl or benzyl substituted respectively, one to three times by fluorine, by chlorine, by bromine, by halogenalkyl with 1 to 5 carbon atoms, by alkyl with 1 to 5 carbon atoms or by alkoxy by 1 to 5. carbon atoms, or together they mean an alkylene radical having 3 to 6 carbon atoms substituted, if appropriate, by alkyl having 1 to 4 carbon atoms, where, if appropriate, a methylene group is replaced by oxygen or sulfur. 4. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen, methyl, chloro, bromo, ethyl, methoxy, ethoxy or trifluoromethyl, means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy , propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, means, in the 4-position, hydrogen, chlorine, bromine, trifluoromethyl or trifluoromethoxy, means hydrogen, also means hydrogen, chlorine, bromine, methyl or ethyl , X also means chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano, and also means, in position 4, the rest Z also means hydrogen, V1 also means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 also means hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, W also means hydrogen, chlorine or methyl, X means the same chlorine mode, methyl or trifluoromethyl, And it means the same way, in position 5, the rest Z means in the same way, in the 4-position, hydrogen or methyl, V1 means in the same way fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 means in the same way hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, W it also means hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine, furthermore it means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy-ethoxy, ethoxy-ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, furthermore means, in the 4-position, methyl or ethyl, also means hydrogen, also means hydrogen, chlorine, bromine, methyl or ethyl, means also chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy, also means, in the 4-position, hydrogen, chlorine, bromine, methyl or ethyl, means also , in position 3 or 5, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or trifluoromethoxy, means -CH2-, -CHCH3-, -CH2-CH2-, -CH2-CHCH3-, -CH2-CH2-CH2- , means hydrogen, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, methoxy-ethoxy, ethoxy-ethoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy , by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, means cyclopentyl or cyclohexyl, in which, if appropriate, a mutilen group is replaced by oxygen, means H or oxygen, means hydrogen, methyl, ethyl, propyl, iso-propyl, cyclopropyl, cyclopentyl or cyclohexyl, means hydrogen, methyl or ethyl, and Q2 signify together with the carbon atom, with which cyclopropyl, cyclopentyl or cyclohexyl, means hydrogen (a) or means one of the groups in which E means a metal ion or an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, alkoxy with 1 to 4 carbon atoms -alkyl with 1 to 2 carbon atoms, alkylthio having 1 to 4 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or means cycloalkyl with 3 a 6 carbon atoms monosubstituted, if appropriate, by fluorine, by chlorine, by methyl, by ethyl or by methoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by ethyl, by n-propyl, by i-propyl, by methoxy, by ethoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, optionally by chlorine, by bromine or by methyl, means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or alkoxy with 1 to 4 carbon atoms-C2-C4-alkyl substituted, if appropriate, one to three times by fluorine or chlorine, means cyclopentyl or cyclohexyl or phenyl or benzyl respectively substituted, if appropriate, by one twice by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy, means methyl, ethyl, propyl or iso-propyl, respectively, optionally substituted by one to three times by fluorine or chlorine, or phenyl monosubstituted, where appropriate, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by isopropyl, by tere, -butyl, by methoxy, by ethoxy, by iso-propoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, and R5 mean, independently of each other, alkoxy with 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms or means phenyl, phenoxy or phenylthio substituted respectively, optionally fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy, and R signify, independently of one another, hydrogen, mean alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 3 to 4 carbon atoms, carbon or alkoxy with 1 to 4 carbon atoms-alkyl with 2 to 4 carbon atoms, meaning substituted phenyl, optionally one to two times fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, or together they mean an alkylene radical having 5 to 6 carbon atoms , in which, if appropriate, a methylene group is replaced by oxygen or by sulfur. 5. Compounds of the formula (I), accog to claim 1, characterized in that it means hydrogen, methyl, ethyl, chlorine or bromine, means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxy-ethoxy , cyclopropyl-methyloxy, trifluoromethyl or difluoromethoxy, means, in position 4, hydrogen, chlorine, bromine, trifluoromethyl or trifluoromethoxy, means hydrogen, means -CH2-, -CHCH3- or -CH2-CH2-, means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, cyclopentyl or cyclohexyl, means NH, means hydrogen or methyl, means hydrogen or methyl, means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms Carbon-alkyl with 1 to 2 atoms carbon, substituted, if appropriate, one to three times by fluorine or by chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, methoxy, trifluoromethyl or trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, if appropriate, by chlorine or methyl, means alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexylor denotes phenyl or benzyl monosubstituted respectively, optionally by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means phenyl substituted by methyl. 6. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen, chlorine, bromine, methyl or ethyl, means chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano, means , in position 4, the rest means hydrogen, means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, means -CH2-, -CHCH3- or -CH2-CH2-, means hydrogen, methyl, ethyl , propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means NH, means hydrogen or methyl, means hydrogen or methyl, means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, R! means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means monosubstituted phenyl, optionally fluorine, chlorine, bromine, cyano, nitro , by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, if appropriate, by chlorine or by methyl, R2 means alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms, carbon or alkoxy having 1 to 2 carbon atoms-alkyl having 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, optionally fluorine, chlorine, cyano, nitro, methyl , by methoxy, by trifluoromethyl or by trifluoromethoxy. 7. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen or methyl, X means chlorine or methyl, Gnifica, in position 5, the rest means, in the 4-position, hydrogen or methyl, means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, means hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, means -CH2-, -CHCH3- or -CH2-CH2 - means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means substituted phenyl, optionally, from one to two times per fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, means NH, means hydrogen or methyl, means hydrogen or methyl, means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 at 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl respectively substituted, if appropriate, by chlorine or by methyl, means alkyl with 1 to 8 atoms of carbon, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl having 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl respectively substituted, if appropriate, by fluorine , by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 8. Compounds of the formula (I), in accordance with claim 1, characterized in that W means hydrogen, methyl, ethyl, chlorine or bromine, X means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, H3CO- (CH2) 2 ~ 0, cyclopropylmethoxy, trifluoromethyl or difluoromethoxy, Y means, in the 4-position, methyl, Z means hydrogen, A means -CH2-, -CHCH3- or -CH2-CH2 -, B means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means substituted phenyl, optionally, from one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, means cyclopropyl, cyclopentyl or cyclohexyl, in which case a methylene group is replaced by oxygen , Q! means hydrogen or methyl, Q2 means hydrogen or methyl, D means NH, G means hydrogen (a) or means one of the groups in which E means an ammonium ion, L means oxygen or sulfur and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means monosubstituted phenyl, optionally fluorine , by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means means furanyl, thienyl or pyridyl monosubstituted respectively, where appropriate, by chlorine or by methyl, means alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms or alkoxy having 1 to 2 carbon atoms-alkyl having 2 to 10 carbon atoms; to 4 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or trifluoromethoxy, means methyl or means phenyl substituted by methyl, and together they mean an alkylene radical having 5 to 6 carbon atoms, in which a methylene group means oxygen. 9. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen, methyl, chlorine or bromine, means chlorine, bromine, methyl, methoxy or trifluoromethyl, means, in position 4, hydrogen, chlorine, bromine or methyl, means, in the 3 or 5 position, chloro, bromo, methyl, ethyl, trifluoromethyl or trifluoromethoxy, means -CH2-, -CHCH3- or -CH2-CH2-, means hydrogen, methyl, ethyl, propyl, iso -propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, cyclopropyl, means phenyl substituted, optionally, one to two times by fluorine, by chlorine, by bromine, by methyl , by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means NH, means hydrogen or methyl, means hydrogen or methyl, means hydrogen (a) or means one of the groups in which L means oxygen and means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means monosubstituted phenyl, optionally fluorine, chlorine , by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, where appropriate, by chlorine or by methyl, means alkyl with 1 to 8 carbon atoms , alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl having 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, where appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 10. Compounds of the formula (I), according to claim 1, characterized in that W means hydrogen, methyl, ethyl, chlorine or bromine, X means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, trifluoromethyl, difluoromethoxy or cyano, Y means, in the 4-position, hydrogen, chloro, bromo, methoxy, trifluoromethyl or trifluoromethoxy, Z means hydrogen, A means -CH2-, B means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, cyclopentyl or cyclohexyl, D means oxygen, Q! means hydrogen or methyl, Q2 means hydrogen or methyl, G means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 at 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, if appropriate, by chlorine or by methyl, means alkyl with 1 to 8 atoms of carbon, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate, by fluorine r, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 11. Compounds of the formula (I), according to claim 1, characterized in that W means hydrogen, chlorine, bromine, methyl or ethyl, X means chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano, And it means, in position 4, the rest Z means hydrogen, V1 means fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, V2 means hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl, And means A means -CH2-, B means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl having 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, D means oxygen, means hydrogen or methyl, means hydrogen or methyl, also means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, R 1 means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine , by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, by chlorine or by methyl, respectively, R2 means alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms carbon-alkyl having 2 to 3 carbon atoms means cyclopentyl or cyclohexyl, or is phenyl or benzyl monosubstituted, respectively, by fluorine, chlorine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy. 12. Compounds of formula (I), according to claim 1, characterized in that it means hydrogen or methyl, means chlorine or methyl, means, in position 5, the rest means, in position 4, hydrogen or methyl, means fluorine, chlorine, methyl, methoxy, trifluoromethyl trifluoromethoxy, means hydrogen, fluorine, chlorine, methyl, methoxy trifluoromethyl, means means -CH2-, means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro,) oxygen, l 1 means hydrogen or methyl,) 2 means hydrogen or methyl,; means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 at 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, by chlorine or by methyl, respectively, means alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 3 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 13. Compounds of the formula (I), according to claim 1, characterized in that it means hydrogen, methyl, chlorine or bromine, means chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, trifluoromethyl, difluoromethoxy or cyano , means, in position 4, methyl or ethyl, means hydrogen, means -CH2-, means hydrogen, methyl, ethyl, propyl, iso-propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy, by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, means cyclopentyl or cyclohexyl, in which, if appropriate, a methylene group is replaced by oxygen, Q! means hydrogen or methyl, Q2 means hydrogen or methyl, D means oxygen, G means hydrogen (a) or means one of the groups in which L means oxygen and M means oxygen or sulfur, means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 at 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means monosubstituted furanyl, thienyl or pyridyl respectively, where appropriate, by chlorine or methyl, R2 means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl with 2 to 4 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, if appropriate, by fluorine, by chlorine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 14. Compounds of the formula (I), according to claim 1, characterized in that W means hydrogen, methyl, chlorine or bromine, X means chlorine, bromine, methyl, methoxy or trifluoromethyl, Y means, in position 4, hydrogen, chlorine, bromine or methyl, Z means, in the 3 or 5 position, chloro, fluoro, bromo, methyl, ethyl, trifluoromethyl or trifluoromethoxy, A means -CH2-, B means hydrogen, methyl, ethyl, propyl, iso- propyl, alkenyl with 2 to 4 carbon atoms, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, means phenyl substituted, if appropriate, one to two times by fluorine, by chlorine, by bromine, by methyl, by methoxy , by trifluoromethyl, by trifluoromethoxy, by cyano or by nitro, means cyclopropyl, means cyclopentyl or cyclohexyl, in which, if appropriate, a methylene group is replaced by oxygen, Ql means hydrogen or methyl, Q2 means hydrogen or methyl, D means oxygen, G means hydrogen (a) or means one of the groups O L ^ R1 (b), / ^ M'R (C), in which L means oxygen and M means oxygen or sulfur, R! means alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms substituted, if appropriate, one to three times by fluorine or chlorine or cyclopropyl, cyclopentyl or cyclohexyl, means phenyl monosubstituted, if appropriate, by fluorine , by chlorine, by bromine, by cyano, by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy, means furanyl, thienyl or pyridyl monosubstituted respectively, by chlorine or by methyl, respectively, R2 means alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms or alkoxy with 1 to 2 carbon atoms-alkyl having 2 to 4 carbon atoms, means cyclopentyl or cyclohexyl, or means phenyl or benzyl monosubstituted respectively, optionally fluorine, chlorine, cyano , by nitro, by methyl, by methoxy, by trifluoromethyl or by trifluoromethoxy. 15. Process for obtaining the compounds of the formula (I), according to claim 1, characterized in that, (A) for the preparation of the compounds of the formula (I-1-a) wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, the compounds of the formula (II) are condensed intramolecularly wherein A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, and means alkyl, in the presence of a diluent and in the presence of a base, (B) for obtaining the compounds of the formula, (? -2-a) wherein A, B, Q1, Q2, X, Y and Z have the meanings indicated above, compounds of the formula (III) are condensed intramolecularly wherein A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a base, (C) for obtaining the compounds of the formulas (1-1-b) to (-2 -2-b) shown above, in which R1, A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, compounds of the formulas shown above (Ila) are reacted to (I-2-a), wherein A, B, Q1, Q2, W, X, Y and Z have the meanings above indicated, respectively a) with compounds of the formula (IV) in which has the meaning indicated above and Hal means halogen or ß) with anhydrides of carboxylic acids of the formula (V) R! -CO-O-CO-R1 (V) in which R1 has the meaning indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-accepting agent; (D) for obtaining the compounds of the formulas (I-1-c) to (? -2-c), shown above, in which R2, A, B, Q1, Q2, W, M, X, Y and Z have the meanings indicated above and L means oxygen, they are made reacting compounds of the formulas (Ila) to (I-2-a) shown above, in which A, B, Q !, Q2, W, X, Y and Z have the meanings given above, respectively with esters of chloroformic acid or with thioesters of chloroformic acid of the formula (VI) -C0-C1 (VI) in which R2 and M have the meanings indicated above, if appropriate in the presence of a diluent and, if necessary, in the presence of an acid-accepting agent; (E) for the preparation of the compounds of the formulas (I-1-c) to (? -2-c) shown above, wherein R2, A, B, Q1, Q2, W, M, X, Y and Z have the meanings indicated above and L means sulfur, the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, wherein A, B, Q ^, Q2,, X, Y and Z have the meanings indicated above, respectively with esters of chloromonothioformic acid or with esters of chlorodithioformic acid of the formula (VII) in which M and R2 have the meanings indicated above, if appropriate, in the presence of a diluent and, if necessary, in the presence of an acid-binding agent, (F) for obtaining the compounds of formulas (1-1-d) to (-2 -2-d) shown above, in which R3, A, B, W, Q1, Q2, X, Y and Z they have the meanings indicated above, the compounds of the formulas (Ila) to (a-2-a) shown above are reacted, wherein A, B, Q !, Q2, W, X, Y and Z have the meanings previously indicated, respectively with sulfonyl chlorides of the formula (VIII) R3-S02-C1 (VIII) in which R 3 has the meaning indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, (G) for the preparation of the compounds of the formulas (I-1-e) up to (? -2-e) shown above, in which L, R4, R5, A, B, Q1, Q2, X, Y and Z have the meanings indicated above, the compounds of the formulas (Ila) are reacted until (? -2-a) previously shown, in which A, B, Q! Q2, W, X, Y and Z have the meanings indicated above, respectively with phosphorus compounds of the formula (IX) R4 Hal - P / (IX) L R in which L, R4 and Retain the meanings indicated above and Hal is halogen, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent, (H) for the preparation of the compounds of the formulas (I-1-f) up to (? -2-f) previously shown, in which E, A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, if the compounds of the formulas (Ila) to (? -2-a) shown above are reacted, in which A, B, Q !, Q2,, X, Y and Z have the meanings indicated above, respectively with metal compounds or with amines of the formulas (X) or (XI) Me (OR10) t (X) R in which Me means a monovalent or divalent metal, t means the number 1 or 2 and RIO, RH, signify, independently of each other, hydrogen or alkyl, if appropriate in the presence of a diluent, to obtain the compounds of the formulas (1 -1- g) to (? -2-g) previously shown, in which L, R6, R7, A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above, the compounds of the formulas (Ila) to (α -2-a) shown above, in which A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above, respectively a) with isocyanates or with isothiocyanates of the formula I) N = C = L (XII) in which R ^ and L have the meanings indicated above, if necessary in the presence of a diluent and, if necessary, in the presence of a catalyst or ß) with carbamic acid chlorides or with thiocarbamic acid chlorides of the formula (XIII) wherein L, R6 and R7 have the meanings indicated above, if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid-binding agent. 16. Agent, characterized in that it comprises an active content of a combination of active products comprising, as components (a ') at least one cyclic ketoenol, substituted, of the formula (I), according to claim 1 and (b ') at least one compound improving the compatibility for the crop plants of the following group of compounds: 4-dichloroacetyl-l-oxa-4-aza-spiro [4.5] -decano (AD-67, MON-4660), l-dichloroacetyl-hexahydro-3, 3, 8a-trimethylpyrrole [1,2-a] -pyrimidin-6 (2H) -one (Dicyclonon, BAS-145138), 4-dichloroacetyl-3, 4- dihydro-3-methyl-2H-1, 4-benzoxazine (Benoxacor), 5-chloroquinoline-8-oxy-acetic acid (1-methyl-hexyl ester) (Cloquintocet-mexyl - see also related compounds in EP publications) -A-86750, EP-A-94349, EP-A-191736, EP 492366), 3- (2-chloro-benzyl) -1- (1-methyl-1-phenyl-ethyl) -urea (Cumyluron), a- (cyanomethoxyimino) -phenylacetonitrile (Cyometrinil), 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-methyl-phenyl) -urea (Daimuron, Dymron), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), piperidin-1-thiocarboxylate of Sl-methyl-1 -phenyl-ethyl (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 (Dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (Fenchlorim), 1- (2,4-dichloro-phenyl) -5-trichloromethyl-1H Ethyl-1, 2, 4-triazole-3-carboxylate (Fenchlorazole-ethyl - see also related compounds in EP-A-174562 and EP-A-346620), 2-chloro-4-trifluoromethyl-thiazole-5 -phenylmethyl carboxylate (Flurazole), 4-chloro-N- (1,3-dioxolan-2-yl-methoxy) -a-trifluoro-acetophenoxy (fluxofenim), 3-dichloroacetyl-5- (2-furanyl) -2 , 2-dimethyl-oxazolidin (Furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate ( Isoxadifen-ethyl - see also related compounds in WO-A-95/07897), 1- (ethoxycarbonyl) -ethyl-3,6-dichloro-2-methoxybenzoate (Lactidichlor), (4-chloro-o-tolyloxy) ) -acetic (CPA), 2- (4-chloro-o-tolyloxy) -propionic acid (Mecoprop), 1- (2, -dichloro-phenyl) -4,5-dihydro- Diethyl 5-methyl-lH-pyrazole-3,5-dicarboxylate (Mefenpyr-diethyl - also see related compounds in the publication OA-91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro [ 4.5] decane-4-carbodithioate (MG-838), 1,8-naphthalic acid anhydride, OI- (1,3-dioxolan-2-yl-methoxyimino) -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, 4- (4-chloro-phenoxy) -butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate , ethyl diphenylmethoxyacetate, methyl 1- (2-chloro-phenyl) -5-phenyl-lH-pyrazole-3-carboxylate, 1- (2,4-dichloro-phenyl) -5-methyl-1H-pyrazole-3 ethyl carboxylate, ethyl l- (2,4-dichloro-phenyl) -5-isopropyl-lH-pyrazole-3-carboxylate, 1- (2,4-dichloro-phenyl) -5- (1-, 1-) ethyl dimethyl-ethyl) -1H-pyrazole-3-carboxylate, 1- (2,4-dichloro- ethyl phenyl) -5-phenyl-lH-pyrazole-3-carboxylate (see also related compounds in EP-A-269806 and EP-A-333131), 5- (2,4-dichloro-benzyl) -2 ethyl-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5- (4-fluoro-phenyl) -5-phenyl-2-isoxazoline-3-carboxylate (see also compounds related to WO-A-91/08202), 5-chloro-quinolin-8-oxy-acetate (1,3-dimethyl-but-1-yl), 5-chloro-quinoline-8-oxy- 4-allyloxy-butyl acetate, 5-chloro-quinolin-8-oxy-acetate of l-allyloxy-prop-2-yl, 5-chloro-quinoxalin-8-oxy-methyl acetate, 5-chloro-quinoline- 8-oxy-ethyl acetate, allyl 5-chloro-quinoxalin-8-oxy-acetate, 5-chloro-quinolin-8-oxy-2-oxo-propyl-1-yl, 5-chloro-quinoline- Diethyl 8-oxy-malonate, diallyl-5-chloro-quinoxalin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate (see also related compounds in EP-A-582198), 4-carboxy-chroman-4-yl-acetic acid (AC-304415, see EP-A-613618), 4-chloro-phenoxy-acetic acid, 3, 3, -dimethyl-4-methoxy-benzophenone, -bromo-4-chloromethylsulfonyl-benzene, 1- [4- (? -2-methoxybenzoyl-sulfamoyl) -phenyl] -3-methyl-urea (aka N- (2-methoxy-benzoyl) -4- [(methylamino- carbonyl) -amino] -benzenesulfonamide), 1- [4- (? -2-methoxybenzoylsulfamoyl) -pheni l] -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-benzoyl) -4- (cyclopropylaminocarbonyl) -benzenesulfonamide, and / or one of the following compounds defined by the general formulas, of the general formula (lia) or of the general formula (Ilb) or of the formula (lie) where m means a number 0,1, 2, 3, 4 or 5, A means one of the divalent heterocyclic groups outlined below, n means a number 0, 1, 2, 3, 4 or 5, means alkanediyl having 1 or 2 carbon atoms substituted, if appropriate, by alkyl having 1 to 4 carbon atoms and / or by alkoxycarbonyl with 1 to 4 carbon atoms and / or alkenyloxycarbonyl with 1 to 4 carbon atoms carbon, means hydroxy, mercapto, amino, alkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino , means hydroxy, mercapto, amino, alkoxy with 1 to 7 carbon atoms, alkenyloxy with 1 to 6 carbon atoms, alkenyloxy with 1 to 6 carbon atoms-alkoxy with 1 to 6 carbon atoms, alkylthio with 1 to 6 atoms of carbon, alkylamino with 1 to 6 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino, means alkyl with 1 to 4 carbon atoms substituted, if appropriate, by fluorine, by chlorine and / or by bromine, it means hydrogen, alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms , dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidine it, substituted, respectively, where appropriate by fluorine, by chlorine and / or by bromine, or means phenyl substituted, if appropriate, by fluorine, by chlorine and / or by bromine or by alkyl with 1 to 4 carbon atoms, means hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, dioxolanyl-alkyl with 1 to 4 carbon atoms, furyl, furyl -alkyl with 1 to 4 carbon atoms, thienyl, thiazolyl, piperidinyl, respectively substituted, by fluorine, chlorine and / or bromine, or phenyl, substituted, if appropriate, by fluorine, by chlorine and / or or by bromine or by alkyl with 1 to 4 carbon atoms, R17 and Rl8 together also means alkanediyl having 3 to 6 carbon atoms or oxaalkanediyl having 2 to 5 carbon atoms substituted, if appropriate, by alkyl having 1 to 4 carbon atoms. to 4 carbon atoms, by phenyl, by furyl, by a ringed benzene ring or by two substituents, which form, together with the carbon atom, with which they are bonded, a carboxy with 5 or 6 members, means hydrogen, cyano , halogen, or means alkyl with 1 to 4 carbon atoms, C3-C6-alkyl or phenyl substituted, respectively, by fluorine, chlorine and / or bromine, if appropriate, means hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or tri - (alkyl having 1 to 4 carbon atoms) -silyl substituted, if appropriate, by hydroxy, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means hydrogen, cyano, halogen, or means alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl, respectively substituted, if appropriate, by fluorine, by chlorine and / or by bromine, means nitro, cyano , halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, means hydrogen, cyano, nitro, halogen, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, means hydrogen, cyano, nitro, halogen, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, and / or the compounds defined below by means of the general formulas, the general formula (lid) or of the general formula (lie) where t means a number 0, 1, 2, 3, 4 or 5, v means a number 0, 1, 2, 3, 4 or 5, R22 means hydrogen or alkyl with 1 to 4 carbon atoms, R23 means hydrogen or alkyl having 1 to 4 carbon atoms, R24 means hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, alkylamino having 1 to 6 carbon atoms or di - (alkyl having 1 to 4 carbon atoms) -amino substituted, if appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl with 3 to 6 carbon atoms, cycloalkyloxy with 3 to 6 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms or cycloalkylamino with 3 to 6 carbon atoms substituted, if appropriate, by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, R25 means hydrogen, alkyl with 1 to 6 carbon atoms substituted, if appropriate, by cyano, by hydroxy, by halogen or alkoxy with 1 to 4 carbon atoms, means alkenyl having 3 to 6 carbon atoms or alkynyl with 3 to 6 carbon atoms, respectively substituted, if appropriate, by cyano or halogen, or means cycloalkyl with 3 a 6 carbon atoms substituted, if appropriate, by cyano or by halogen or by alkyl with 1 to 4 carbon atoms, means hydrogen, alkyl having 1 to 6 carbon atoms substituted, if appropriate, by cyano, by hydroxy, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 3 to 6 carbon atoms or alkynyl with 3 to 6 carbon atoms substituted, respectively, by cyano or by halogen, means cycloalkyl with 3 to 6 atoms of carbon substituted, if appropriate, by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, or means phenyl substituted, if appropriate, by nitro, by cyano, by halogen, by alkyl with 1 to 4 carbon atoms; carbon, by halogenoalkyl with 1 to 4 át carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms, or together with R25 means alkanediyl with 2 to 6 carbon atoms or oxaalkanediyl with 2 to 5 carbon atoms substituted respectively, optionally, by alkyl having 1 to 4 carbon atoms, means nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, and X5 means nitro, cyano , carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms . 17.- Compounds of the formula (II) characterized in that A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above. 18.- Compounds of the formula (XVI) characterized because A, B, Q !, Q2, W, X, Y and Z have the meanings indicated above. 19.- Compounds of the formula (XIV) characterized in that A, B, Q !, and R8 have the meanings indicated above. 20.- Compounds of the formula (XVII) characterized because A, B, Q! and Q2 have the meanings indicated above. 21.- Compounds of the formula (XIX) characterized because A, B, Q1, Q2, W, X, Y and Z have the meanings indicated above. 22.- Compounds of the formula (XVIII) (XVIII) characterized because A, B, Q! and Q2 have the meanings indicated above. 23.- Compounds of the formula (III) characterized in that A, B, Q1, Q2, W, X, Y, Z and R8 have the meanings indicated above. 24.- Compounds of the formula (XX) characterized because A, B, QI, Q2 and R.8 have the meanings indicated above. 25. - Pesticide agents and / or herbicides and / or fungicides, characterized in that they have a content of at least one compound of the formula (I) according to claim 1. 26. - Procedure for the control against animal pests and / or the undesirable growth of plants and / or plants. fungi, characterized in that compounds of the formula (I) according to claim 1 are allowed to act on the pests and / or on their environment. 27. Use of the compounds of the formula (I) according to claim 1 for the control against animal pests and / or against the undesirable growth of plants and / or against fungi. 28. - Process for obtaining pesticides and / or herbicides and / or fungicides, characterized in that the compounds of the formula (I) are mixed according to claim 1 with spreaders and / or surfactants. 29. Use of the compounds of the formula (I) according to claim 1 for the preparation of pesticides and / or herbicides and / or fungicides. 30. Agent according to claim 16, characterized in that it is chosen that the compound improving the the compatibility with the crop plants among the following group of compounds: Cloquintocet-mexyl, Fenchlorazole-ethyl, Isoxadifen-ethyl, Mefenpyr-diethyl, Furilazole, Fenclorim, Cumyluron, Dymron oder compounds IIe-5 or IIe-11. 31.- Procedure for combating the undesirable growth of plants, characterized in that agents are allowed to act on the plants or on their environment in accordance with claim 16. 32.- Use of an agent according to claim 16 for the fight against the undesirable growth of plants. 33.- Procedure for combating the undesirable growth of plants, characterized in that a compound of the formula (I) is allowed to act on the plants or on its environment, in accordance with claim 1, and an improving compound of the compatibility with the crop plants, according to claim 16, separately, in a close order in time, or in mixture.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004030753.9 | 2004-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06015186A true MXPA06015186A (en) | 2008-10-03 |
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