EP0809632A1 - Substituted heterocyclic compounds and their use as fungicides - Google Patents
Substituted heterocyclic compounds and their use as fungicidesInfo
- Publication number
- EP0809632A1 EP0809632A1 EP96902952A EP96902952A EP0809632A1 EP 0809632 A1 EP0809632 A1 EP 0809632A1 EP 96902952 A EP96902952 A EP 96902952A EP 96902952 A EP96902952 A EP 96902952A EP 0809632 A1 EP0809632 A1 EP 0809632A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- ethyl
- optionally substituted
- cyano
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000417 fungicide Substances 0.000 title abstract description 14
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 80
- 230000008569 process Effects 0.000 claims abstract description 54
- -1 3-aza-l-propene-2,3-diyl Chemical group 0.000 claims description 554
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 79
- 239000000460 chlorine Substances 0.000 claims description 68
- 229910052801 chlorine Inorganic materials 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 68
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 66
- 229910052731 fluorine Inorganic materials 0.000 claims description 65
- 239000011737 fluorine Substances 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- 150000002367 halogens Chemical class 0.000 claims description 62
- 229910052760 oxygen Inorganic materials 0.000 claims description 59
- 239000001301 oxygen Substances 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
- 239000011593 sulfur Substances 0.000 claims description 54
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 36
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 35
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 150000003254 radicals Chemical class 0.000 claims description 30
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000002576 ketones Chemical class 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 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 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 13
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
- 125000005412 pyrazyl group Chemical group 0.000 claims description 13
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 11
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 11
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
- 125000005495 pyridazyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 8
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 8
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 7
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000004175 fluorobenzyl group Chemical group 0.000 claims description 7
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 7
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 7
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 6
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 4
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000003556 thioamides Chemical class 0.000 claims description 4
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 4
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical group C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 26
- 241000607479 Yersinia pestis Species 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 2
- 239000000575 pesticide Substances 0.000 claims 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- XMDSATDCLNTLRP-UHFFFAOYSA-N C1=CC=C(C=C1)C=CC(=O)C=CC(=O)C2=CC=CC=C2 Chemical group C1=CC=C(C=C1)C=CC(=O)C=CC(=O)C2=CC=CC=C2 XMDSATDCLNTLRP-UHFFFAOYSA-N 0.000 claims 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 claims 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000013067 intermediate product Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- 239000000203 mixture Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000007858 starting material Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
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- 238000000338 in vitro Methods 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 1
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- 238000002386 leaching Methods 0.000 description 1
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- 239000011572 manganese Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
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- XUPLRQAOWMPRMN-UHFFFAOYSA-N methyl-(2-methylphenyl)cyanamide Chemical compound N#CN(C)C1=CC=CC=C1C XUPLRQAOWMPRMN-UHFFFAOYSA-N 0.000 description 1
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- 125000003566 oxetanyl group Chemical group 0.000 description 1
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- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
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- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
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- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/62—Carboxylic acid nitriles containing cyano groups and oxygen atoms being part of oxyimino groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07C2601/14—The ring being saturated
Definitions
- the invention relates to new substituted heterocyclic compounds, several processes for their preparation and their use as fungicides, and new intermediates, several processes for their production and their use as fungicides
- Ar represents optionally substituted arylene or heteroarylene.
- E stands for a 1 -alkylene-1.1 -d ⁇ yl grouping, in 2-position a residue
- R 1 contains, or stands for a 2-aza-l-alkene-l, l-diyl grouping which contains a radical R : in 2-position, or for an optionally substituted imino grouping ("Azamethylene", NR) stands, or for a 3-aza-l - propen-2,3-diyl grouping, which contains a radical R 1 in the 1 position and a radical R "in the 3 position, or for a 3-oza-l -propen-2,3-d ⁇ vl- grouping which contains a radical R in the 1 position, or for a 3- Thia-l-propen-2,3-diyl grouping which contains a radical R 1 in the 1-position, or represents an l-aza-l-propene-2,3-diyl grouping which is in 1-position, or represents an l-aza-l-propene-2,3-diyl grouping which is in 1-
- Position contains a radical R ⁇ and in the 3-position a radical R j , or stands for an l-aza-l-propene-2,3-diyl grouping, the radical R 1 in the 1 position and the 3 position contains a radical R 3 , or represents a 1,3-diaza-l-propene-2,3-diyl grouping which contains a radical R 2 in the 1 position and a radical R 3 in the 3 position, or for an l-aza-3-oxa-l-propene-2,3-diyl group which contains a radical R 2 in the 1-position, or for an l-aza-3-thia-l-propene-2, 3-d ⁇ yl grouping, which contains a radical R ⁇ in the 1 position, where
- R 1 represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
- R 2 represents hydrogen, amino, hydroxy, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
- R 3 represents hydrogen, cyano, hydroxy or optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
- G for a single bond, for oxygen, sulfur or, if appropriate, in each case by halogen, 1, haloalkyl or cycloalkyl substituted alkanediylalkenediyl.
- Alkindn I or one of the following groups -Q-CQ-, -CQ-0-, -CH : -O- -Q-CH ; -CQ-Q-CH : -, -CH ; -Q-CQ-, ⁇ -Q-CQ-CH : - -Q-CQ-O-CH ; - -N N-, -S (O) favour- -CH : -S (O) ⁇ -
- Ar 1 for optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene ie a doubly linked aliphatic a ring in which one or more carbon atoms is replaced by heteroatoms, ie atoms other than carbon
- n the numbers 0, 1 or 2
- Q oxygen or sulfur
- R 4 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
- R 3 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl and
- T represents a single bond, oxygen, sulfur, -CH 2 -O-, CH -.- S- or optionally substituted alkanediyl and
- Z represents] optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl
- Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl
- heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member contains a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these may be the same or different. Heteroatoms are preferred Oxygen, nitrogen or sulfur If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic, aromatic ring systems
- R has the meaning given above,
- A represents optionally substituted alkylene
- R 6 represents amino or -SH
- R stands for Al vl or hydrogen
- R 1 has the meaning given above and
- R 10 represents aryl or alkyl
- R 1 1 represents alkyl
- R 12 represents hydrogen or alkyl
- X 1 represents halogen
- Y ! represents cyano, alkylcarbonyl, arylcarbonyl, formyl, dialkoxyalkyl or alkoxycarbonyl,
- Y represents hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl, or alkoxycarbonyl
- the new substituted carboxamides of the general formula (I) show very strong fungicidal activity
- the compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z isomers, but optionally also of tautomers. Both the E and the Z isomers, any mixtures of these Isomers and the possible tautomeric forms are claimed
- the invention preferably relates to compounds of the formula (I) in which
- Ar stands for optionally substituted phenylene or naphthylene, for mono- or bicyclic heteroarylene with 5 or 6 ring members each or for benzo-fused heteroarylene with 5 or 6 ring members, at least one of which represents oxygen, sulfur or nitrogen and optionally one or two more Are nitrogen, where the possible substituents are preferably selected from the list below
- Thiocarbamoyl in each case straight-chain or branched alkylene, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkene i Alkenvlow or alkionylox ⁇ each having 2 to 6 carbon atoms, each straight-chain or branched halogenalkvl, halogenoalkow.
- R 1 represents hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C ] -C 4 -alkoxy,
- R is hydrogen, amino, hydroxy, cyano or for alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C r C 4 alkoxy,
- R stands for hydrogen, cyano, hydroxy or for alkyl, alkoxy, alkoxyalkyl, alkenyl or alkynyl, each optionally substituted by halogen or cyano, each having up to 6 carbon atoms or for each optionally halogen, cyano, C, -C 4 alkyl or C 1 -C 4 alkoxy-substituted cycloalkylene or cycloalkylene with 3 to 6 carbon atoms in the cycloalkylene and optionally 1 to 4 carbon atoms in the alkylene.
- n the numbers 0, 1 or 2
- Q oxygen or sulfur
- R 4 for hydrogen, cyano, for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C ] -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or for each optionally by halogen, Cyano, carboxy, C ] -C 4 alkyl or C ] -C 4 alkoxycarbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
- R 5 is hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C j - alkoxy or is optionally substituted by halogen, cyano, carboxy, C ] -C 4 alkyl or C l -C4 -Alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms and
- haloalkyl straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- T stands for a single bond, for oxygen, sulfur, -CH -, - 0-, CH -, - S- or for alkanediyl with 1 to 3 carbon atoms,
- alkylidene for optionally by alkylidene, arylalkyls.
- alkenyl or alkynyl each optionally substituted by halogen, each having up to 8 carbon atoms,
- C 4 haloalkoxy is substituted), C ⁇ C. j -alkyl or C 1 -C 4 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
- phenyl which is optionally mono- or polysubstituted by identical or different substituents.
- alkyl each straight-chain or branched alkyl.
- Alkoxy Alkylthio.
- Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms,
- alkylamino straight-chain or branched alkylamino, dialkvlamino, alkylcarbonyl, alkylcarbonylox), alkoxycarbonyl or alkylsulfonyloxy, each having 1 to 6 carbon atoms in the individual alkyl parts,
- Heterocyclyl or Heterocvcivl-meth ⁇ l each with " up to 7 ring members, each of which has 1 to 3 identical or different heteroatoms - especially nitrogen, oxygen and / or sulfur! -
- a 2 for optionally by Cvano, C, -C 4 -alkoxy C, -C 4 -Alkylth ⁇ o, C r C 4 -alkylam ⁇ no, C, -C 2 -D ⁇ alkvlam ⁇ no, phenyl, halophenyl methylphenyl triformeth ⁇ lphenyl, or C, -C 2 alkoxyphenyl substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl each having 2 to 4 carbon atoms.
- the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
- Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine
- the invention relates in particular to compounds of the formula (I) in which
- Methoxy Ethoxy, methylthio, methylsulfinyl or methylsulfonyl.
- R 1 for hydrogen, fluorine, chlorine, bromine. Cyano or for methyl, ethyl, propyl, methoxy which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy. Ethoxy, methylthio, Ethvlthio, methylamino, ethylamino or dimethylamino.
- R 2 stands for hydrogen, amino, hydroxy, cyano or for methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
- R 1 represents hydrogen, cyano or, in each case optionally by fluorine,
- Chlorine or cyano substituted methyl, ethyl n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy or methoxymethyl, for allyl or propargyl or for each optionally by fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, methoxy or ethoxy-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.
- n the numbers 0, 1 or 2
- Q represents oxygen or sulfur
- R 4 for hydrogen, cyano, each optionally by fluorine.
- R 5 represents hydrogen, hydroxyl, cyano or methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethox, or each optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl,
- T ⁇ fluoreth ⁇ 1 Difluormethoxv T ⁇ fluormethow Difluorchlor- T ⁇ fluorethow D ⁇ fluormeth ⁇ lth ⁇ o Difluorchlormethv lthio T ⁇ fluormethvlthio T ⁇ fluormethv lsulfinl 1,, T ⁇ fluor ethv 1- sulfonl lm, methacl ⁇ methion ⁇ meth carbon ⁇ l methox ⁇ m ⁇ noeth ⁇ l ethox ⁇ m ⁇ noeth ⁇ l or cyclopropyl and T for a single bond, for oxygen, sulfur, -CH -, - 0-, CH -, - S-
- Cyclopropyl Cyclobutyl, cyclopentyl or cyclohexyl, or a group in which
- a 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
- Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
- R stands for hydrogen, cyano, methyl. Ethyl n- or i-propyl, methoxy. Ethoxy or methoxymethyl.
- n the numbers 0, 1 or 2
- Q oxygen or sulfur
- R 4 represents hydrogen, cyano, methyl, Eth 1 or cyclopropyl
- R 5 represents hydrogen, methyl, ethyl or cyclopropyl
- Ar for in each case monosubstituted to trisubstituted, identically or differently, substituted phenylene or py ⁇ dinediyl, for in each case optionally monosubstituted py ⁇ midindiyl, py ⁇ dazindiyl, pyrazinediyl, 1,2,3-triazidndyl, 1, 2,4-triazidndyl or 1, 3,5-T ⁇ a- zindiyl or stands for 1, 2,4-Th ⁇ ad ⁇ azold ⁇ vl, 1, 3,4-Th ⁇ ad ⁇ azold ⁇ yl, 1,2,4-oxadiazole diyl, 1,3,4-Oxad ⁇ azold ⁇ yl, the possible substituents preferably from of the following payment are selected
- Methylene, ethylene or propylene stands and R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
- Fluorine Chlorine. Bromine, cyano, methyl, ethyl. n- or i-propyl, n-, i-, s- or t-butyl. Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio.
- a particularly preferred group of compounds according to the invention are the viable compounds of the formula (I)
- Ar represents ortho-phenylene, pyrid-2,3-dimyl or thiophen-2,3-dimyl,
- R 1 and R 2 each represent methoxy
- R ' represents hydrogen, methylene or ethylene
- G stands for -O-CH
- ring members for saturated heterocyclyl with 3 to 8 ring members optionally substituted one or more times by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
- Z represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below
- Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
- Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
- R 1 and R 2 each represent methoxy
- R 3 represents hydrogen, methyl or Ethvl.
- R 4 represents hydrogen, cyano, methyl, ethyl or cyclopropyl
- 1,2,5-oxadiazolyl furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1, 2,3-thiadiazolyl, 1 each bonded via a carbon atom and in each case optionally substituted by methyl, methoxy or hydroxy , 2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1, 3,4-thiadiazolyl, pyridyl, pyrimidyl. Pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1,3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
- Z represents phenyl, pyridyl or pyrimidyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below
- Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
- Ar represents ortho-phenylene
- R and R each represent methoxy
- R ⁇ represents hydrogen, methyl or ethyl
- G represents -T-Ar '-Q-,
- Q oxygen or sulfur
- 1,2,5-oxadiazolyl furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1, 2,3-thiad ⁇ azolyl, 1, each bonded via a carbon atom and optionally substituted by methyl, methoxy or hydroxy, 2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1, 3, 5-t ⁇ azyl, partially or fully hydrogenated thiazolyl or thiazinyl,
- Formula (II) provides a general definition of the ketones required as starting materials for carrying out process a) according to the invention.
- Ar, G, R and Z preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Ar, G, R and Z were specified.
- ketones of the formula (II) are not yet known; as new substances, they are the subject of the present application.
- ketones of the formula (II) are obtained (process a-al)) if carboxamides of the general formula (X),
- R 1 - "1 and R 14 are the same or different and are for alkyl. Or together with the
- Nitrogen atom to which they are attached represent an optionally substituted ring in which one or two further ring members are heteroatoms,
- M represents lithium or -Mg-X 2 , where X 2 represents chlorine, bromine, iodine or R,
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example
- Petroleum ether hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; or an ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, at temperatures from -80 to +50, preferably -80 and + 25 ° C, implemented
- the amides required as starting materials for carrying out the process a-al) according to the invention are generally defined by the formula (X)
- Ar, G and Z preferably or in particular have those meanings which have already been associated with the description of the invention
- Compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, G and Z.
- R 13 and R 14 are the same or different and stand for alkyl, preferably methyl, ethyl, n- or i-propyl, or together with the nitrogen atom to which they are attached, for an alkyl, optionally one or more times, by alkyl, preferably methyl or ethyl, substituted, three, four, five, six or seven-membered ring, in which one or two more, if appropriate
- Ring members are heteroatoms, preferably nitrogen, oxygen or sulfur
- carboxamides of the formula (X) are known and / or can be prepared by known methods (compare, for example, DE-A 2806562 or WO-A 9422844)
- T 1 represents a single bond, oxygen, sulfur, -CH 2 -O-, CH : -S- or optionally substituted alkanediyl and
- Z 4 represents optionally substituted phenyl
- R 1 ⁇ represents hydrogen or alkyl
- R u> for optionally by cycloalkyl.
- R ,: v and R ⁇ ' together with the nitrogen atom to which they are attached represent a heterocyclic ring which may be substituted by alkyl and which still contain an oxygen or nitrogen atom
- X 3 represents halogen, hydroxy, alkoxy, alkylthio or -O-CO-Ar-GZ,
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon such as petroleum ether or toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as tetrahydrofuran, a nitrile such as acetonitrile or an amide . such as N, N-dimethylformamide. an ester such as ethyl acetate, a sulfoxide such as dimethyl sulfoxide, a Sufone such as sulfolane.
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon such as petroleum ether or toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as tetrahydrofuran, a nitrile such as acetonitrile or an amide . such as N, N-dimethylformamide. an ester such as ethyl acetate
- Ar stands for 1,2,4-oxadiazole diyl, 1,3,4-oxadiazoldionyl, 1,2,4-thioadazoleionyl, 1,3,4-thioadazoleionyl or for pyrimidinediyl or 1,3,5-triazide diyl which is optionally monosubstituted by halogen ,
- T 1 stands for a single bond, for oxygen, sulfur, -CH ---, -CH -, - CH, -, -CH 2 -O- or -CH 2 -S- and
- a 3 represents methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, cyclopropyl or cyclobutyl and
- R 1 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butylene,
- R 16 for methyl, cyclopropylmethyl, hydroxy, methoxy, ethoxy or for ethyl which is optionally substituted by carboxy, hydroxy or methoxy, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2 - or 3-pentyl, 1-, 2- or 3-
- the acid derivatives used to carry out process a-a2) according to the invention for the preparation of the carboxamides of the formula (Xa) as starting materials are generally defined by the formula (XII).
- G 1 and Z 4 preferably or in particular have the relevant meanings X ⁇ stands for halogen, preferably chlorine Hvdroxv, which have already been given in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for G 1 and Z 4 .
- the acid derivatives of the formula (XII) are known and / or can be prepared by processes known per se (cf., for example, EP-A 493711)
- Formula (XIII) provides a general definition of the amines required as starting materials for carrying out process a-a2) for the preparation of the carboxamides of the formula (Xa).
- R 15 and R 16 preferably or in particular have those Meanings which have already been given in connection with the description of the carboxamides of the formula (Xa) as preferred or as particularly preferred for R 15 and R 16
- Formula (XI) provides a general definition of the organometallic compounds which are further required as starting materials for carrying out process a-al) according to the invention for the preparation of the ketones of the formula (II).
- R preferably or in particular has the meaning which has already been associated with the description of the compounds of the invention
- R M stands for lithium or -Mg-X 2 , where X 2 stands for chlorine, bromine, iodine or R.
- organometallic compounds of the formula (XI) are known and / or can be prepared by processes known per se (see, for example, BJ Org Chem, 1962, 27, 1216, Synth Comm., 1982, 12, 23 1, J Org Chem 1971, 36,
- R stands for pyrrolyl, imidazolyl, pyrazolyl, t ⁇ azolyl or tetrazolyl
- the ketones of the formula (II) are also obtained (process a-bl)) if carbonsaurenit ⁇ le of the general formula (XIV),
- a diluent preferably an ahphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decahn, or an ether, such as, for example, diethyl ether, dnsopropyl ether, methyl -t -butyl ether, methyl-t-amvl ether, dioxane, tetrahvdrofuran, 1, 2-dimethoxvethane, 1, 2-d ⁇ ethoxvethane or anisole at temperatures from -80 to
- the formula (XIV) provides a general definition of the carboxylic acid nitrogens required as starting materials for carrying out the process according to the invention from l).
- Ar, G and Z preferably or in particular have the meanings already given in connection with the description of the compounds according to the invention of the formula (I) have been indicated as preferred or as particularly preferred for Ar G and Z.
- the carboxylic acid nitriles of the formula (XIV) are known and / or can be prepared by processes known per se (cf., for example, EP-A 278 595 or J. Org Chem. (1982), 47 (8), 1546-55)
- ketones of the formula (II) are also obtained (process a-cl)) if halogen compounds of the general formula (XV)
- X 4 represents halogen
- magnesium shavings or butyllithium in a generally customary manner and
- R has the meaning given above and R and R are identical or different and stand for alkyl, or together with the nitrogen atom to which they are attached, for an optionally substituted ring in which one or two further ring members are optionally heteroatoms,
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; or an ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, at temperatures from -80 to + 50, preferably -80 and + 25 ° C, implemented
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohex
- halogen compounds required as starting materials for carrying out the process a-cl) according to the invention are generally defined by the formula (XV).
- Ar, G and Z preferably or in particular have those meanings which have already been associated with the description of the invention Compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, G and Z.
- halogen compounds of the formula (XV) are known and / or can be prepared by processes known per se (see, for example, Synthesis 1981, (2), 1 17, EP-A 525 516, EP-A 585 751, Bull Korean Chem Soc (1989), 10 (4), 397-400.
- the formulas (XVI) and (XVII) which are generally required as starting materials for carrying out the process a-cl) according to the invention for the preparation of the ketones of the formula (II) are generally defined by the formulas (XVI) and (XVII) in these formulas (XVI) and (XVII) R preferably or in particular the meaning which has already been given as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention.
- R 1 and R 1 K are identical or different and stand for alkyl, preferably methyl, ethyl, n- or i-propyl, or together with the nitrogen atom to which they are attached, for an optionally single or multiple alkyl, preferably methyl or ethyl. substituted, three, four, five, six or seven-membered ring in which optionally one or two further ring members are heteroatoms, preferably nitrogen, oxygen or sulfur.
- ketones of the formula (II) can also be obtained if aromatic
- the nitriles required as starting materials for carrying out process b) according to the invention are generally defined by the formula (IV).
- Ar, E, G and Z preferably or in particular have those meanings which have already been described in connection with the description of the invention ⁇ According to compounds of formula (I) as preferred or as particularly preferred for Ar, E, G and Z have been given
- nitriles of the formula (IV) are known and / or can be prepared by processes known per se (cf. for example EP-A 528 68 1. also compare the preparation examples).
- X "" 1 represents halogen
- R 4 and Z have the meanings given above,
- a diluent preferably an ether, such as tetrahydrofuran. of a ketone. like acetone. a nitrile such as acetonitrile. an amide such as N, N-dimethylformamide or a sulfoxide such as
- an acid acceptor preferably an alkali metal hydride, hydroxide or carbonate, such as sodium hydride, sodium hydroxide or potassium carbonate at temperatures from -20 to 120 ° C.
- Formula (XXII) generalizes the halomethyl compounds required as starting materials for carrying out process b-1) according to the invention
- Ar and R 3 preferably or in particular have those meanings which have already been given as preferred or as particularly preferred for Ar and R 3 in connection with the description of the compounds of the formula (I) according to the invention
- a conventional halogenating agent such as bromine, chlorine, N-bromosuccinimide or N-iodosuccinimide
- a diluent preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, hexane or benzene, or a halogenated hydrocarbon, such as, for example, carbon tetrachloride, and, if appropriate, the presence of a radical, such as benzoyl peroxide or azodiisobutyronitol, optionally under irradiation with UV light, at a temperature of from -20 to 120 ° C.
- a radical such as benzoyl peroxide or azodiisobutyronitol
- MethvlMISen are represented by the formula (XX ⁇ T) provides a general definition In this formula (XXVI), Ar and R "is preferably or in particular the j enigen meanings that already in connection with Description of the compounds of formula (I) according to the invention as preferred or as ms-particularly preferred for Ar and R 1
- the methyl compounds of the formula (XXVI) are known and / or can be prepared by processes known per se (see Org Synth Coll Vol 1955, 608)
- R 4 and Z preferably or in particular have those meanings which are already in connection with the description of the compounds according to the invention of the formula (I) as being preferred or as being particularly preferred for R 4 and Z.
- hydroxy compounds of the formulas (XXIII), (XXIV) or (XXV) are known synthetic chemicals and / or can be prepared by processes known per se
- bifunctional alkylene compounds which are also required as starting materials for carrying out process b) according to the invention are represented by the formula
- R 9 is alkyl preferably methyl or ethyl
- A represents optionally substituted, straight-chain or branched alkylene If R 6 and R 7 simultaneously represent amino, A preferably represents straight-chain or branched alkylene having 2 to 10 carbon atoms, in particular ethane which is optionally mono-, di- or trisubstituted by methylene or ethylene l l, 2-d ⁇ yl, propane l, 3-d ⁇ yl or butane 1, 4-d ⁇ yl R stands for
- A preferably represents straight-chain or branched alkylene having 1 to 8 carbon atoms, in particular in each case methylene substituted once, twice or three times by methyl or ethyl.
- the bifunctional alkylene compounds of the formula (V) are known synthetic chemicals
- R 1 preferably or in particular has the meaning which is already in connection with the description of the compounds according to the invention of the formula (I) was given as preferred or as particularly preferred for R 1 , is -P (R 10 ) 3 + X _ or -PO (OR n ) 2 , where R 10 is aryl, preferably phenyl or C 1 -C 4 alkyl, preferably butyl, and R n is alkyl, preferably methyl or ethyl, and X is halogen, preferably chlorine, bromine or iodine
- the phosphorus compounds of the formula (VI) are known organic synthesis chemicals
- Formula (VII) provides a general definition of the thioamides required as starting materials for carrying out process d) according to the invention.
- Ar, E, G and Z preferably or in particular have those meanings which have already been described in connection with the description of the invention ⁇ compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, E, G and Z.
- haloalkyl compounds also required as starting materials for carrying out process d) according to the invention.
- or acetylene compounds are generally defined by the formulas (VIII) or (IX)
- R 1 is hydrogen or alkyl.
- Preferably hydrogen or methyl Y 1 is cyano, alkylcarbonyl. arylcarbonyl, formyl. dialkoxyalkyl or Al koxy carb ony l, preferably for cy ano, form yl, di eth oxym ethv.
- X 1 represents halogen, preferably chlorine or bromine
- Y 1 is hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl, or Alkoxycarbonyl, preferably for hydrogen, methyl, ethyl, phenyl, acetyl, benzoyl,
- Methoxvcarbonvl or Ethoxvcarbonvl The haloalkyl compounds of the formula (VIII) are known synthetic chemicals.
- Suitable diluents for carrying out processes a), b), c) and d) are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane , Dichloroethane or trichloroethane, ethers, such as diethyl ether.
- aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin
- Processes a) and b) according to the invention are optionally carried out in the presence of an acid or a base
- Processes c) and d) according to the invention are optionally carried out in the presence of a suitable acid acceptor
- Suitable acids for carrying out processes a) and b) according to the invention are all inorganic and organic, and also all polymeric acids. These include, for example, hydrogen chloride, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid. Toluene sulfonic acid, acidic ion exchangers, acidic clays and acidic silica gel Suitable bases or acid acceptors for carrying out processes a), b), c) and d) are all customary inorganic or organic bases.
- alkaline earth metal or alkali metal hydrides such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate,
- Potassium tert-butoxide sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylanil , N, N-dimethylbenzylamine, pyridine, N-methylpiperidine,
- N-methylmorpholine N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU)
- reaction temperatures can be varied within a substantial range. In general, temperatures between -20 ° C. and + 200 ° C., preferably at
- reaction temperatures can also be varied within a substantial range when carrying out process c) according to the invention.
- temperatures between -50 ° C. and -H 00 ° C. preferably at temperatures between -20 ° C and + 50 ° C
- reaction temperatures can also be varied over a wide range in carrying out process d) according to the invention. In general, temperatures from 0 ° C. to 150 ° C., preferably at temperatures
- haloalkylene compound of the formula (VIII.) are generally employed per mol of the thioamide of the formula (VII) ) or acetylene compound of the formula (IX)
- Processes a), b), c) and d) according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar
- reaction, processing and isolation of the reaction products of the processes according to the invention is carried out by known methods (cf. also the preparation examples).
- the active compounds according to the invention have a strong microbicidal action and are used practically to combat unwanted microorganisms.
- the active compounds are particularly suitable for use as crop protection agents as fungicides
- Fungicidal agents in crop protection are used to combat plasmodiophoromvcetes, oomvcetes chyt ⁇ diomvcetes, and gomvcetes ascomvcetes
- Pvthium species such as, for example, Pvthium ultimum Phvtophthora species, such as, for example, Phytophthora infestans,
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
- Plasmopara species such as, for example, Plasmopara viticola
- Peronospora species such as Peronospora pisi or Peronospora brassicae Erysiphe species, such as, for example, Erysiphe graminis,
- Sphaerotheca species such as, for example, Sphaerotheca fuliginea
- Podosphaera species such as, for example, Podosphaera leucotricha
- Venturia species such as, for example, Venturia inaequalis
- Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym Helminthosporium)
- Cochliobolus species such as Cochliobolus sativus (conidia form
- Drechslera synonym: Helminthosporium
- Uromyces species such as, for example, Uromyces appendiculatus
- Puccinia species such as, for example, Puccinia recondita
- Tilletia species such as, for example, Tilletia caries,
- Ustilago species such as, for example, Ustilago nuda or Ustilago avenae
- Pellicularia species such as, for example, Pellicularia sasakii
- Pyricularia species such as, for example, Pyricularia oryzae
- Fusarium species such as, for example, Fusarium culmorum
- Botrytis species such as, for example, Botrytis cinerea
- Septoria species such as, for example, Septoria nodorum
- Leptosphaeria species such as, for example, Leptosphaeria nodorum
- Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae,
- Pseudocercosporella species such as, for example, Pseudocercosporella herpot ⁇ choides
- the active compounds according to the invention are particularly successful in combating cereal diseases, for example against Erysiphe species. or of diseases in wine, fruit and vegetable growing, such as for example against Plasmopara species, or of rice diseases, such as against
- the active compounds are converted into conventional formulations, such as, for. B. solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm fog formulations
- formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
- extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
- organic solvents can, for example, also be used as auxiliary solvents.
- Aromatic compounds such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene, or methylene chloride, aliphatic hydrocarbons, are essentially suitable as liquid solvents.
- Cyclohexane or paraffins e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water, with liquefied gaseous extenders or carriers are meant as liquids which are used for are gaseous at normal temperature and pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane.
- solvents such as butanol or glycol
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
- strongly polar solvents such as dimethylformamide or dimethyl sulfoxide
- gaseous extenders or carriers are meant as liquids which are used for are gaseous at normal
- Propane, nitrogen and carbon dioxide, as solid carrier materials come into consideration, for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse
- Silicic acid, aluminum oxide and silicates for example broken and fractionated natural rocks such as calcite are suitable as solid carriers for granules.
- emulsifiers and / or foam-producing agents are nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, are suitable as dispersants. e.g. lignin sulfite leaching and methyl cellulose
- adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers are used in the formulations, such as, for. B. gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
- Other possible additives are mineral and vegetable oils.
- dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are added
- the formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds according to the invention are used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of action or to prevent the development of resistance.
- Benalaxyl Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S.
- Calcium polysulfide Captafol, Captan, Carbendazim. Carboxin, quinomethionate
- Kasugamycin copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux
- Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicvofen, thiophanate-methyl, thiram, tolclophos-methyl, tolv fluanid, t ⁇ adilamon, t ⁇ demolum, t ⁇ flumol, t ⁇ flumcinol
- Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
- Clocyth ⁇ n Clofentezin, Cyanophos, Cycloproth ⁇ n, Cyfluth ⁇ n, Cvhaloth ⁇ n,
- Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
- Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucyth ⁇ nat, Flufenoxuron, Flufenprox, Fluv- ahnate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
- Lamda-cyhalothnn Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd Methac ⁇ fos,
- Tebufenozid Tebufenpyrad
- Tebupirimphos Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhrononium, Trionomoshrononium, Triomenethriazonium, Tri
- the active compounds according to the invention are also mixed with other known active compounds, such as herbicides or else with fertilizers and growth regulators
- the active ingredients are used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules. They are used in the customary manner, for example by pouring, spraying, spraying, scattering, Dusting, foaming, brushing, etc. If necessary, the active ingredients are applied using the ultra-low-volume method or the active ingredient preparation or the active ingredient itself is injected into the soil. If appropriate, the seeds of the plants are also treated
- the active compound concentrations in the use forms can be varied within a substantial range and are generally between 1 and 0.0001% by weight, preferably between 0.5 and
- active substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action
- the active compounds according to the invention have a strong microbicidal action and are used in practice to combat unwanted microorganisms.
- the active compounds are for use as crop protection agents. particularly suitable as fungicides
- Fungicidal agents in crop protection are used to combat plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
- Pythium species such as Pythium ultimum
- Phytophthora species such as, for example, Phytophthora infestans
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
- Plasmopara species such as, for example, Plasmopara viücola
- Peronospora species such as, for example, Peronospora pisi or Peronospora brassicae
- Erysiphe species such as, for example, Erysiphe graminis
- Sphaerotheca species such as, for example, Sphaerotheca fuliginea
- Podosphaera species such as, for example, Podosphaera leucotricha
- Venturia species such as, for example, Venturia inaequalis
- Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea (conidia form Drechslera, synonym Helminthosporium),
- Cochliobolus species such as, for example, Cochliobolus sativus (conidia form Drechslera, synonym Helminthosporium),
- Uromvces species such as, for example, Uromyces appendiculatus
- Puccinia species such as Puccinia recondita.
- Tilletia species such as, for example, Tilletia ca ⁇ es,
- Ustilago species such as, for example, Ustilago nuda or Ustilago avenae
- Pellicula ⁇ a species such as, for example, Pelhcula ⁇ a sasakii
- Pv ⁇ cula ⁇ a species such as Pyricularia oryzae
- Fusa ⁇ um species such as Fusa ⁇ um culmorum.
- Botrytis species such as, for example, Botrvtis cinerea.
- Septo ⁇ a species such as Septoria nodorum
- Leptosphae ⁇ a species such as Leptosphae ⁇ a nodorum
- Cercospora species such as, for example, Cercospora canescens,
- the active compounds according to the invention are used with particularly good success for combating diseases in wine, fruit and vegetable cultivation, such as, for example, against Plasmopara and Podosphaera species
- the active compounds according to the invention are also used with good success for combating cereal diseases, for example against Septoria, Pyricularia, Pyrenophora and Cochliobolus species.
- the active compounds according to the invention have a particularly good in vitro effect
- the active ingredients may be converted into customary formulations, such as, for example, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also ULV cold and warm fog formulations
- Auxiliary solvents are used as liquid solvents are essentially aromatics such as xvol toluene alkanol naphthane chlorinated aromatics or chlorinated ahphatic hydrocarbons such as chlorobenzenes, chlorethethane or methylene chloride or methane carbon dioxide and cvclohexane or paraffins, e.g. petroleum fractions Alcohols such as butanol or
- Glv kol and their ethers and ester ketones such as acetone, methylene chloride, methylene isobutyl ketone or Cv clohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide. as well as water, with liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and pressure, e.g.
- Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide
- solid carrier materials e.g. natural rock powder such as kaolins, alumina talc, chalk, quartz attapulgite mont- Morillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules organic material such as sawdust,
- natural rock powder such as kaolins, alumina talc, chalk, quartz attapulgite mont- Morillonite or diatomaceous earth
- synthetic rock flour such as highly disperse silica, aluminum oxide and silicates
- coconut shells, corn cobs and tobacco stalks are suitable as emulsifying and / or foaming agents, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein dispersants in question, for example, lignin sulfite liquor and methyl cellulose
- nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein dispersants in question, for example, lignin sulfite liquor and methyl cellulose
- Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as, for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, are further possible additives in the formulations mineral and vegetable oils.
- dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese
- the formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%
- the active substances according to the invention are also mixed with known fungicides, bactericides,
- Akarizi nematicides or insecticides are used to broaden the spectrum of activity or to prevent resistance
- Fungicides for the mixtures, for example Fungicides:
- Fenpropi-morph Fenünacetate, Fenünhydroxyd, Ferbam, Fe ⁇ mzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolaml,
- Kasugamycin copper preparations such as copper hydroxide, copper naphthenate
- Mancopper Mancozeb, Maneb, Mepanipy ⁇ m
- Mepronil Metalaxyl
- Metconazol Methasulfocarb Methfuroxam, Meüram, Metsulfovax, Myclobutanil,
- Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
- Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap.
- Chlorfluazuron Chlormephos, Chlorpyrifos, Chlo ⁇ yrifos M, Cis-Resmethrin.
- Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb.
- Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
- Methamidophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
- Parathion A Parathion M, Permeth ⁇ n, Phenthoat, Phorat, Phosalon, Phosmet,
- Tebufenozid Tebufenpyrad
- Tebupirimphos Teflubenzuron, Tefluth ⁇ n, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thu ⁇ ngiensin, Talarophathos, Tralomethosen, Tralomethosen.
- the active compounds according to the invention are also used with other known active compounds, such as herbicides or with fertilizers and
- the active ingredients as such in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders. Dusting agents and granules applied The application takes place in the usual way, e.g. by pouring, spraying,
- the active ingredients are applied using the ultra-low-volume process or the active ingredient preparation or the material itself is injected into the soil. If necessary, the seeds of the plants are also treated In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
- active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.2% by weight, are required
- E-isomeric retention index 2285, M 322, 321, 290, 214, 199, 183,
- Tetrahydrofuran 2.8 g (0.01 mol) of 23% n-butyllithium are added dropwise at ⁇ 20 ° C. After 15 minutes of stirring at ⁇ 20 ° C., 1.48 g (0.005 mol) of N- [2- (2-Methylphenoxymethyl) benzoyl] pyrrolidine, dissolved in 10 ml of tetrahydrofuran, and stirred again for 30 minutes at -20 ° C. 2 g of ammonium chloride and 10 ml of methanol are added and the mixture is boiled under reflux for 15 minutes volatile constituents, the residue is mixed with water and extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo.
- Page 113 are dissolved in 40 ml of tetrahydrofuran. 3 g of this solution are added to 0.88 g (0.036 mol) of magnesium shavings. After adding a drop of bromine, the mixture is boiled up boils under reflux for an hour. Then 3.76 g (0.036 mol) of 2-cyanopyridine, dissolved in, are added at -20.degree
- Emulsifier 0.3 parts by weight of alkylaryl polyglycol ether
- Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether
- the plants are sprinkled with Erys ⁇ he gra ims f.sp.hordei spores
- the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative air humidity of approx. 80% in order to promote the development of mildew pustules
- Emulsifier 0.3 parts by weight of alkylaryl polyglycol ether
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Abstract
The invention relates to novel substituted heterocyclic compounds, several processes for their production and their use as fungicides, and novel intermediate products, several processes for their production and their use as fungicides.
Description
SUBSTITUIERTE HETEROCYCLISCHE VERBINDUNGEN UND IHRE VERWENDUNG ALS FUNGIZIDESUBSTITUTED HETEROCYCLIC COMPOUNDS AND THEIR USE AS FUNGICIDES
Die Erfindung betrifft neue substituierte heterocyclische Verbindungen, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide, sowie neue Zwischenprodukte, mehrere Verfahren zu deren Herstellung und deren Verwendung als FungizideThe invention relates to new substituted heterocyclic compounds, several processes for their preparation and their use as fungicides, and new intermediates, several processes for their production and their use as fungicides
Es ist bekannt, daß bestimmte substituierte heterocyclische Verbindungen fungizide Eigenschaften aufweisen (vgl. EP-A 633252 und WO-A 9422844) Die Wirkung dieser Verbindungen ist jedoch insbesondere bei niedrigen Aufwand¬ mengen nicht in allen Anwendungsgebieten völlig zufriedenstellendIt is known that certain substituted heterocyclic compounds have fungicidal properties (cf. EP-A 633252 and WO-A 9422844). However, the action of these compounds is not entirely satisfactory in all fields of application, in particular at low application rates
Es wurden nun die neuen substituierten heterocyclischen Verbindungen der all¬ gemeinen Formel (I) gefunden,The new substituted heterocyclic compounds of the general formula (I) have now been found
G ~ EG ~ E
(I) in welcher(I) in which
Ar für gegebenenfalls substituiertes Arylen oder Heteroarylen steht.Ar represents optionally substituted arylene or heteroarylene.
E für eine 1 -Alken- 1.1 -dιyl-Gruppιerung steht, die in 2-Posιtιon einen RestE stands for a 1 -alkylene-1.1 -dιyl grouping, in 2-position a residue
R1 enthalt, oder für eine 2-Aza-l-alken-l,l-diyl-Gruppιerung steht, die in 2-Positιon einen Rest R: enthalt, oder für eine gegebenenfalls substituierte Imino-Gruppierung ("Azamethylen", N-R ) steht, oder für eine 3-Aza-l - propen-2,3-diyl-Gruppιerung steht, die in 1 -Position einen Rest R1 und in 3-Position einen Rest R" enthalt, oder für eine 3-Oza-l -propen-2,3-dιvl- Gruppierung steht, die in 1 -Position einen Rest R enthalt, oder für eine 3-
Thia-l-propen-2,3-diyl-Gruppierung steht, die in 1 -Position einen Rest R1 enthalt, oder für eine l-Aza-l-propen-2,3-diyl-Gruppierung steht, die in 1-R 1 contains, or stands for a 2-aza-l-alkene-l, l-diyl grouping which contains a radical R : in 2-position, or for an optionally substituted imino grouping ("Azamethylene", NR) stands, or for a 3-aza-l - propen-2,3-diyl grouping, which contains a radical R 1 in the 1 position and a radical R "in the 3 position, or for a 3-oza-l -propen-2,3-dιvl- grouping which contains a radical R in the 1 position, or for a 3- Thia-l-propen-2,3-diyl grouping which contains a radical R 1 in the 1-position, or represents an l-aza-l-propene-2,3-diyl grouping which is in 1-
.->.->
Position einen Rest R~ und in 3-Position einen Rest Rj enthalt, oder für eine l-Aza-l-propen-2,3-diyl-Gruppιerung steht, die in 1 -Position einen Rest R1 und in 3-Position einen Rest R3 enthalt, oder für eine 1,3-Dιaza-l- propen-2,3-diyl-Gruppierung steht, die in 1 -Position einen Rest R2 und in 3-Position einen Rest R3 enthalt, oder für eine l -Aza-3-oxa-l-propen-2,3- diyl -Gruppierung steht, die in 1 -Position einen Rest R2 enthalt, oder für eine l-Aza-3-thia-l-propen-2,3-dιyl-Gruppιerung steht, die in 1 -Position einen Rest R~ enthalt, wobeiPosition contains a radical R ~ and in the 3-position a radical R j , or stands for an l-aza-l-propene-2,3-diyl grouping, the radical R 1 in the 1 position and the 3 position contains a radical R 3 , or represents a 1,3-diaza-l-propene-2,3-diyl grouping which contains a radical R 2 in the 1 position and a radical R 3 in the 3 position, or for an l-aza-3-oxa-l-propene-2,3-diyl group which contains a radical R 2 in the 1-position, or for an l-aza-3-thia-l-propene-2, 3-dιyl grouping, which contains a radical R ~ in the 1 position, where
R1 für Wasserstoff, Halogen, Cyano oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkyl- amino steht,R 1 represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R2 für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils gegebe- nenfalls substituiertes Alkyl, Alkoxy, Alkylamino oder Dialkyl- amino steht, undR 2 represents hydrogen, amino, hydroxy, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R3 für Wasserstoff, Cyano, Hydroxy oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkenyl, Alkinyl, Cyclo- alkyl oder Cycloalkylalkyl steht,R 3 represents hydrogen, cyano, hydroxy or optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
G für eine Einfachbindung, für Sauerstoff Schwefel oder für j eweils gegebenenfalls durch Halogen,
1 , Halogenalkyl oder Cycloalkyl substituiertes Alkandiyl Alkendiyl. Alkindn l oder eine der nachstehenden Gruppierungen -Q-CQ-, -CQ-0-, -CH:-O- -Q-CH;- -CQ-Q-CH:-, -CH;-Q-CQ-, ^ -Q-CQ-CH:- -Q-CQ-O-CH;- -N=N-, -S(O)„- -CH:-S(O)π-G for a single bond, for oxygen, sulfur or, if appropriate, in each case by halogen, 1, haloalkyl or cycloalkyl substituted alkanediylalkenediyl. Alkindn I or one of the following groups -Q-CQ-, -CQ-0-, -CH : -O- -Q-CH ; -CQ-Q-CH : -, -CH ; -Q-CQ-, ^ -Q-CQ-CH : - -Q-CQ-O-CH ; - -N = N-, -S (O) „- -CH : -S (O) π -
-CQ-. -S(O)n-CH:-, -C(R )=\-O-, -C(R )=N-O-CH,-, -N(R , -CQ-N(R , -N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH2-, -CH2-O-N=C(R4)-, -N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH2-, -Q-C(R4)=N-O-CH2-, -N(R5)-C(R4)=N-O-CH2-, -O-CH:-C(R4)=N-O-CH2-, 0 -N=N-C(R4)=N-O-CH2-, -T-Ar1- oder -T-Ar!-Q- steht, wobei-CQ-. -S (O) n -CH : -, -C (R) = \ - O-, -C (R) = NO-CH, -, -N (R, -CQ-N (R, -N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH 2 -, -CH 2 -ON = C (R 4 ) -, -N (R 5 ) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH 2 -, -QC (R 4 ) = NO-CH 2 -, -N (R 5 ) -C (R 4 ) = NO-CH 2 -, -O-CH : -C (R 4 ) = NO-CH 2 -, 0 -N = NC (R 4 ) = NO-CH 2 -, -T-Ar 1 - or -T-Ar ! -Q-, where
Ar1 für gegebenenfalls substituiertes Arylen, Heteroarylen, Cycloalkylen oder Heterocycloalkylen (d h ein zweifach verknüpfter aliphati-
scher Ring, in dem ein oder mehrere Kohlenstoffatome durch Heteroatome, d.h. von Kohlenstoff verschiedene Atome ersetzt sind) steht,Ar 1 for optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene (ie a doubly linked aliphatic a ring in which one or more carbon atoms is replaced by heteroatoms, ie atoms other than carbon),
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
Q für Sauerstoff oder Schwefel steht,Q represents oxygen or sulfur,
R4 furWasserstoff, Cyano oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino oder Cyclo- alkyl steht, undR 4 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R3 für Wasserstoff, Hydroxy, Cyano oder jeweils gegebenenfalls sub- stituiertes Alkyl, Alkoxy oder Cycloalkyl steht undR 3 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH2-O-, CH-.-S- oder für gegebenenfalls substituiertes Alkandiyl steht undT represents a single bond, oxygen, sulfur, -CH 2 -O-, CH -.- S- or optionally substituted alkanediyl and
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Stickstoffatom alkylsubstituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1 ,2,3-Triazolyl, 1 ,2,4-Triazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and optionally alkyl-substituted on a nitrogen atom,
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls substituiertes 1 ,2,5-Oxadiazolyl, Furyl , Thienyl , 1 ,2-Thιazolyl . 1 ,3 - Thiazolyl, 4-Oxo-l ,3-thiazol-2-yl, 1 ,2,3-Thιadιazolyl, 1 ,2,4-Thιadιazolyl, 1 ,2,5-Thιadiazolyl, 1 ,3 ,4-Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyπdazyl , 1 ,2.3-Triazyl, 1 ,2,4-TπazyI, 1 ,3,5-Triazyl , partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,for 1, 2,5-oxadiazolyl, furyl, thienyl, 1, 2-thιazolyl each bonded via a carbon atom and optionally substituted. 1, 3 - thiazolyl, 4-oxo-l, 3-thiazol-2-yl, 1, 2,3-thιadιazolyl, 1, 2,4-thιadιazolyl, 1, 2,5-thιadiazolyl, 1, 3, 4- Thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyπdazyl, 1, 2,3-triazyl, 1, 2,4-tπazyI, 1, 3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für jeweils gegebenenfalls substituiertes, gesättigtes Heterocyclyl mit mindestens einem Sauerstoff und/oder mindestens einem Schwefelatom,for in each case optionally substituted, saturated heterocyclyl with at least one oxygen and / or at least one sulfur atom,
oder für gegebenenfalls substituiertes l,3-Dιazacycloalk- l-en-2-yl steht,or represents optionally substituted 1,3-dazacycloalk-l-en-2-yl,
Z für ]eweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cyclo¬ alkyl, Aryl oder Heterocyclyl steht
Aryl steht für aromatische, mono oder polycyclische Kohlenwasserstoffringe, wie z.B. Phenyl, Naphthyl, Anthranyl, Phenanthryl, vorzugsweise Phenyl oder Naphthyl, insbesondere PhenylZ represents] optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl
Heterocyclyl steht, wenn nicht anders definiert, für gesattigte oder ungesättigte, sowie aromatische, ringförmige Verbindungen, in denen mindestens ein Ringglied ein Heteroatom, d h ein von Kohlenstoff verschiedenes Atom, ist Enthalt der Ring mehrere Heteroatome, können diese gleich oder verschieden sein Heteroatome sind bevorzugt Sauerstoff, Stickstoff oder Schwefel Gegebenenfalls bilden die ringförmigen Verbindungen mit weiteren carbocychschen oder hetero- cyclischen, ankondensierten oder überbrückten Ringen gemeinsam ein polycyc- lisches Ringsystem Bevorzugt sind mono- oder bicychsche Ringsysteme, insbesondere mono- oder bicyclische, aromatische RingsystemeUnless otherwise defined, heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member contains a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these may be the same or different. Heteroatoms are preferred Oxygen, nitrogen or sulfur If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic, aromatic ring systems
Weiterhin wurde gefunden, daß man die neuen substituierten heterocyclischen Verbindungen der allgemeinen Formel (I) erhält, wenn manFurthermore, it was found that the new substituted heterocyclic compounds of the general formula (I) can be obtained if
a) Ketone der allgemeinen Formel (II)a) ketones of the general formula (II)
in welcher in which
Ar, G. R und Z die oben angegebenen Bedeutungen habenAr, G. R and Z have the meanings given above
mit einem A in der Formel (III),with an A in formula (III),
R:-NH2 (III)R : -NH2 (III)
in welcherin which
R: die oben angegebene Bedeutung hat,R : has the meaning given above,
oder einem Saureadditionskomplex davon, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reak- tionshüfsmittels. umsetzt.
oder wenn manor an acid addition complex thereof, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary. implements. or if you
b) Nitrile der allgemeinen Formel (IV)b) nitriles of the general formula (IV)
Zs „Ar .CN G ΕZ s "Ar .CN G Ε
(IV) in welcher(IV) in which
> Ar, E, G und Z die oben angegebenen Bedeutungen haben,> Ar, E, G and Z have the meanings given above,
mit einer bifunktionellen Alkylenverbindung der allgemeinen Formel (V),with a bifunctional alkylene compound of the general formula (V),
R -A-R7 (V)R -AR 7 (V)
in welcherin which
A für gegebenenfalls substituiertes Alkylen steht,A represents optionally substituted alkylene,
) R6 für Amino oder -SH steht,) R 6 represents amino or -SH,
R7 für Amino. -COOR oder -CH(OR9): steht, wobeiR 7 for amino. -COOR or -CH (OR 9 ) : stands, where
R für Al vl oder Wasserstoff steht undR stands for Al vl or hydrogen and
R" für Alkvl steht,R "stands for Alkvl,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reaktionshilfsmittels. umsetzt,if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary. implements
oder wenn manor if you
c) Ketone der allgemeinen Formel (II)c) ketones of the general formula (II)
O (II)
in welcher O (II) in which
Ar, G, R und Z die oben angegebenen Bedeutungen habenAr, G, R and Z have the meanings given above
mit Phosphorverbindungen der allgemeinen Formel (VI)with phosphorus compounds of the general formula (VI)
@— R1 (VI)@ - R 1 (VI)
in welcherin which
R1 die oben angegebene Bedeutung hat undR 1 has the meaning given above and
(g) für -P(R10)X X" oder für -PO(ORn ): steht,(g) stands for -P (R 10 ) XX " or for -PO (OR n ) :
wobeiin which
R10 für Aryl oder Alkyl steht,R 10 represents aryl or alkyl,
R1 1 für Alkyl steht undR 1 1 represents alkyl and
X für Halogen steht,X represents halogen,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reaktionshilfsmittels, umsetztif appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary
oder wenn manor if you
d) Thioamide der allgemeinen Formel (VII)d) thioamides of the general formula (VII)
SS
G E NH2 GE NH 2
(VII)(VII)
in welcherin which
Ar, G, E und Z die oben angegebenen Bedeutungen haben
mit Halogenalkylverbindungen der allgemeinen Formel (VIII)Ar, G, E and Z have the meanings given above with haloalkyl compounds of the general formula (VIII)
in welcherin which
R12 für Wasserstoff oder Alkyl steht,R 12 represents hydrogen or alkyl,
X1 für Halogen steht,X 1 represents halogen,
Y! für Cyano, Alkylcarbonyl, Arylcarbonyl, Formyl, Dialkoxyalkyl oder Alkoxycarbonyl steht,Y ! represents cyano, alkylcarbonyl, arylcarbonyl, formyl, dialkoxyalkyl or alkoxycarbonyl,
oder mit Acetylenverbindungen der Formel (IX)or with acetylene compounds of the formula (IX)
Y2 Z= Y3 (I ) in welcherY 2 Z = Y 3 (I) in which
Y" für Alkoxycarbonyl steht undY "stands for alkoxycarbonyl and
Y für Wasserstoff, Alkyl, Aryl, Alkylcarbonyl, Arylcarbonyl, oder Alkoxycarbonyl steht,Y represents hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl, or alkoxycarbonyl,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reaktionshilfsmittels, umsetzt.if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
Steht R" für Alkoxy. erweist es sich in manchen Fällen als vorteilhaft, zunächst die entsprechenden Hydroxyverbindungen (R~ = OH) nach Verfahren a) herzu¬ stellen, und diese dann nach üblichen Methoden zu alky HerenIf R "stands for alkoxy. In some cases it proves advantageous to first prepare the corresponding hydroxy compounds (R ~ = OH) by process a), and then to prepare them according to customary methods
Schließlich wurde gefunden, daß die neuen substituierten Carbonsäureamide der allgemeinen Formel (I) sehr starke fungizide Wirkung zeigen
Die erfindungsgemaßen Verbindungen können gegebenenfalls als Mischungen ver¬ schiedener möglicher isomerer Formen, insbesondere von Stereoisomeren, wie z B E- und Z-Isomeren, gegebenenfalls aber auch von Tautomeren vorliegen Es werden sowohl die E- als auch die Z-Isomeren, beliebige Mischungen dieser Iso- meren, sowie die möglichen tautomeren Formen beanspruchtFinally, it was found that the new substituted carboxamides of the general formula (I) show very strong fungicidal activity The compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z isomers, but optionally also of tautomers. Both the E and the Z isomers, any mixtures of these Isomers and the possible tautomeric forms are claimed
Gegenstand der Erfindung sind vorzugsweise Verbindungen der Formel (I), in welcherThe invention preferably relates to compounds of the formula (I) in which
Ar für jeweils gegebenenfalls substituiertes Phenylen oder Naphthylen, für mono- oder bicyclisches Heteroarylen mit jeweils 5 oder 6 Ringgliedern oder für benzokondensiertes Heteroarylen mit 5 oder 6 Ringgliedern, von denen jeweils mindestens eines für Sauerstoff, Schwefel oder Stickstoff steht und gegebenenfalls ein oder zwei weitere für Stickstoff stehen, steht, wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindAr stands for optionally substituted phenylene or naphthylene, for mono- or bicyclic heteroarylene with 5 or 6 ring members each or for benzo-fused heteroarylene with 5 or 6 ring members, at least one of which represents oxygen, sulfur or nitrogen and optionally one or two more Are nitrogen, where the possible substituents are preferably selected from the list below
Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl,Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl,
Thiocarbamoyl, jeweils geradkettiges oder verzweigtes Alkvl, Alkoxy, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoff¬ atomen, jeweils geradkettiges oder verzweigtes Alkem i Alkenvlow oder Alkιnylox\ mit jeweils 2 bis 6 Kohlenstoffatomen, jeweils geradkettiges oder verzweigtes Halogenalkvl, Halogenalkow . Halogenalk\ lthio Halogen-
lsulfin\ 1 oder Halogenalkvlsulfonv l mit jeweils 1 bi s b Kohlenstoff¬ atomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen, jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenvlow mit leweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiede- nen Halogenatomen, jeweils geradkettiges oder verzweigtes AlkvlaminoThiocarbamoyl, in each case straight-chain or branched alkylene, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkene i Alkenvlow or alkionylox \ each having 2 to 6 carbon atoms, each straight-chain or branched halogenalkvl, halogenoalkow. Halogenalk \ lthio halogen Isulfin \ 1 or Halogenalkvlsulfonv l each with 1 bi sb carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or halogenalkenvlow with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alklamino
Dialkylamino, Alkylcarbonyl, Alkvlcarbonvlox) , Alkoxycarbonyl, Alkyl- sulfonvlox\ , Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen, leweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen und/oder geradkettiges oder verzweigtes Halogenalkyl mit 1 bis 4 Kohlen¬ stoffatomen und 1 bis 9 gleichen oder verschiedenen Halogenatomen sub¬ stituiertes, leweils zweifach verknüpftes Alkylen oder Dioxyalkvlen mit jeweils 1 bis 6 Kohlenstoffatomen,
für eine der nachstehenden Gruppierungen stehtDialkylamino, alkylcarbonyl, alkvlcarbonvlox), alkoxycarbonyl, alkylsulfonvlox \ , hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 Carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, represents one of the groupings below
RJ R J
II.
" N . N, " N. N,
'C ' C
CH IICH II
^R2 CH N^ R 2 CH N
R1 R2 worinR 1 R 2 wherein
R1 für Wasserstoff, Halogen, Cyano oder für jeweils gegebenenfalls durch Halogen, Cyano oder C]-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino mit jeweils 1 bis 6 Kohlen stoff atomen in den Alkylresten steht,R 1 represents hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C ] -C 4 -alkoxy,
R- für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils gege¬ benenfalls durch Halogen, Cyano oder CrC4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylamino oder Dialkylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den Alkylresten steht,R is hydrogen, amino, hydroxy, cyano or for alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C r C 4 alkoxy,
R für Wasserstoff, Cyano, Hydroxy oder für jeweils gegebenenfalls durch Halogen oder Cyano substituiertes Alkyl, Alkoxy, Alkoxy- alkyl, Alkenyl oder Alkinyl mit jeweils bis zu 6 Kohlenstoff atomen oder für jeweils gegebenenfalls durch Halogen, Cyano, C,-C4-Alkyl oder C1-C4-Alkoxy- substituiertes Cycloalkvl oder Cycloalkvlalkvl mit 3 bis 6 Kohlenstoffatomen in den Cvcloalkvlteilen und ge¬ gebenenfalls 1 bis 4 Kohi enstoffatomen im Alk\ lteιl steht.R stands for hydrogen, cyano, hydroxy or for alkyl, alkoxy, alkoxyalkyl, alkenyl or alkynyl, each optionally substituted by halogen or cyano, each having up to 6 carbon atoms or for each optionally halogen, cyano, C, -C 4 alkyl or C 1 -C 4 alkoxy-substituted cycloalkylene or cycloalkylene with 3 to 6 carbon atoms in the cycloalkylene and optionally 1 to 4 carbon atoms in the alkylene.
für eine Einfachbindung, für Sauerstoff, Schwefel oder für jeweils gegebenenfalls durch Halogen, Hydroxy, Cj-Cj-Alkyl, C.-C -Halogenalkyl oder C^-C -Cycloalkyl substituiertes Alkandiyl, Alkendiyl, Alkindiyl mit leweils bis zu 4 Kohlenstoffatomen oder eine der nachstehenden Gruppie¬ rungenrepresents a single bond, represents oxygen, sulfur or represents in each case optionally substituted by halogen, hydroxyl, C j -C j -alkyl, C.-C haloalkyl, or C ^ -C cycloalkyl alkanediyl, alkenediyl, alkinediyl having leweils up to 4 carbon atoms or one of the groups below
-Q-CQ-, -CQ-Q-, -CH;-Q-, -Q-CH:-, -CQ-Q-CH2-, -CH.-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2-, -C(R )=N-O-. -C(R4)=N-O-CH2-, -N(R5)-, -CQ-N(R5)- -N(R5)-CQ-, -Q-CQ-N(R , -N=C(R4)-Q-CH;-, -CH2-0-N=C(R4)-, -N(R5)-CQ-Q-, -CQ-N(R CQ-Q-, -N(R5)-CQ-Q-CH.-.
-Q-C(R4)=N-O-CH2-, -N(R5)-C(R4)=N-O-CH2-, -O-CH2-C(R4)=N-O-CH2-,-Q-CQ-, -CQ-Q-, -CH ; -Q-, -Q-CH : -, -CQ-Q-CH 2 -, -CH.-Q-CQ-, -Q-CQ-CH 2 -, -Q-CQ-Q-CH 2 -, - N = N-, -S (O) n -, -CH 2 -S (O) n -, -CQ-, -S (O) n -CH 2 -, -C (R) = NO-. -C (R 4 ) = NO-CH 2 -, -N (R 5 ) -, -CQ-N (R 5 ) - -N (R 5 ) -CQ-, -Q-CQ-N (R, - N = C (R 4 ) -Q-CH ; -, -CH 2 -0-N = C (R 4 ) -, -N (R 5 ) -CQ-Q-, -CQ-N (R CQ-Q -, -N (R 5 ) -CQ-Q-CH.-. -QC (R 4 ) = NO-CH 2 -, -N (R 5 ) -C (R 4 ) = NO-CH 2 -, -O-CH 2 -C (R 4 ) = NO-CH 2 -,
-N=N-C(R4)=N-O-CH2-, -T-Ar1- oder -T-Ar'-Q- steht, wobei-N = NC (R 4 ) = NO-CH 2 -, -T-Ar 1 - or -T-Ar'-Q-, where
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
Q für Sauerstoff oder Schwefel steht,Q represents oxygen or sulfur,
R4 für Wasserstoff, Cyano, für jeweils gegebenenfalls durch Halogen, Cyano oder C]-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino mit jeweils 1 bis 6 Kohlenstoff¬ atomen in den AJkylgruppen oder für jeweils gegebenenfalls durch Halogen, Cyano, Carboxy, C] -C4-Alkyl oder C] -C4-Alkoxy- carbonyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht, undR 4 for hydrogen, cyano, for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C ] -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or for each optionally by halogen, Cyano, carboxy, C ] -C 4 alkyl or C ] -C 4 alkoxycarbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
R5 für Wasserstoff, Hydroxy, Cyano oder für gegebenenfalls durch Halogen, Cyano oder Cj- -Alkoxy substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen oder für gegebenenfalls durch Halogen, Cyano, Carboxy, C]-C4-Alkyl oder C l -C4-Alkoxy-carbonyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen steht undR 5 is hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C j - alkoxy or is optionally substituted by halogen, cyano, carboxy, C ] -C 4 alkyl or C l -C4 -Alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms and
Ar1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenvlen, Naphthylen Cvcloalkvlen oder für Heteroarvlen oder Heterocvcloalkvlen mit 3 bis 7 Ringgliedern von denen mindestens eines für Sauerstoff, Schwefel oder Stickstoff und gegebenenfalls ein oder zwei weitere für Stickstoff stehen steht, wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindAr 1 for each optionally mono- or polysubstituted, identically or differently substituted phenylene, naphthylene, Cvcloalkvlen or for heteroarvlen or heterocvcloalkvlen with 3 to 7 ring members, of which at least one is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, where the possible substituents are preferably selected from the following list
Halogen, C\ ano Nitro Amino. Hvdrox\ Formyl Carbow Carb- amovl ThiocarbamovlHalogen, C \ ano Nitro Amino. Hvdrox \ Formyl Carbow Carbamovl Thiocarbamovl
jeweils geradkettiges oder verzweigtes Alkyl, Alkox\ , lkvlthio Alkvlsulfinvl oder Alk\ lsulfonvl mit jeweils 1 bis 6 Kohlenstoff¬ atomen,
jeweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxy mit jeweils 2 bis 6 Kohlenstoff atomen;in each case straight-chain or branched alkyl, alkoxyl, alkylene sulfonyl or alk sulfonyl, each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogen- alkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkyl- sulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
jeweils geradkettiges oder verzweigtes Alkylamino, Dialkylamino,each straight-chain or branched alkylamino, dialkylamino,
Alkylcarbonyl, Alkylcarbonyloxy, Alkoxycarbonyl, Alkylsulfonyl- oxy, Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen, sowie;Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, and;
Cycloalkyl mit 3 bis 6 Kohlenstoffatomen undCycloalkyl with 3 to 6 carbon atoms and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH-,-0-, CH-,-S- oder für Alkandiyl mit 1 bis 3 Kohlenstoffatomen steht,T stands for a single bond, for oxygen, sulfur, -CH -, - 0-, CH -, - S- or for alkanediyl with 1 to 3 carbon atoms,
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Stickstoffatom durch C l-C4-Alkyl substituiertes Pyrrolyl, Imida- zolyl, Pyrazolyl, 1 ,2,3-Triazolyl, 1 ,2,4-Triazolyl, Tetrazolyl.R for pyrrolyl, imidazolyl, pyrazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, tetrazolyl each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by C 1 -C 4 -alkyl.
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls durch Alkyl, Alkoxy oder Hydroxy substituiertes 1 ,2.5-Oxadiazolyl, Furyl, Thienyl, 1 ,2-Thiazolyl, 1 ,3-Thiazolyl, 1.2.3-Thiadiazolyl, 1 ,2.4-Thia- diazolyl, 1 ,2,5-Thiadiazolyl, 1 ,3.4-Thiadiazolyl. Pyridyl. Pyrimidy . Pyrazyl. Pyridazyl, 1 ,2.3-Triazyl, 1 ,2,4-Triazyl . 1 ,3 ,5-Triazyl . partiel l oder vollständig hydriertes Thiazolyl oder Thiazinyl.for 1, 2.5-oxadiazolyl, furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1,2,3-thiadiazolyl, 1, 2,4-thia, each bonded via a carbon atom and optionally substituted by alkyl, alkoxy or hydroxy diazolyl, 1, 2,5-thiadiazolyl, 1, 3,4-thiadiazolyl. Pyridyl. Pyrimidy. Pyrazyl. Pyridazyl, 1, 2,3-triazyl, 1, 2,4-triazyl. 1, 3, 5-triazyl. partial l or fully hydrogenated thiazolyl or thiazinyl.
für gegebenenfalls durch Alkyliden, Arylalkyhden. Alkylcarbonylalkiden, Arylcarbonylalkyhden oder Alkoxycarbonylalkyliden substituiertes 4-Oxo- 1.3-thiazol-2-yl,
für jeweils gegebenenfalls durch Cl-C4-Alkyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei mindestens ein Ringglied für Sauerstoff und/oder Schwefel steht,for optionally by alkylidene, arylalkyls. Alkylcarbonylalkides, arylcarbonylalkyls or alkoxycarbonylalkylidene-substituted 4-oxo-1,3-thiazol-2-yl, for saturated heterocyclyl with 3 to 8 ring members optionally substituted by C1-C4-alkyl, at least one ring member representing oxygen and / or sulfur,
oder für gegebenenfall s durch C l -C4-Alkyl substituiertes 1 , 3 - Diazacycloalk-l -en-2-yl mit 4 bis 7 Ringgliedern steht,or for optionally 1, 3-diazacycloalk-1-en-2-yl with 4 to 7 ring members substituted by C 1 -C 4 -alkyl,
Z für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durchZ for optionally single or multiple, the same or different
Halogen, Cyano, Hydroxy, Amino, C,-C4-Alkoxy, C,-C4-Alkylthio, CrC4-Halogen, cyano, hydroxy, amino, C, -C 4 -alkoxy, C, -C 4 -alkylthio, C r C 4 -
Alkylsulfinyl oder C1-C4-Alkylsulfonyl (welche jeweils gegebenenfalls durch Halogen substituiert sein können) substituiertes Alkyl mit 1 bis 8 Kohlenstoff atomen,Alkylsulfinyl or C 1 -C 4 -alkylsulfonyl (which may in each case optionally be substituted by halogen) substituted alkyl having 1 to 8 carbon atoms,
für jeweils gegebenenfalls durch Halogen substituiertes Alkenvl oder Alkinyl mit jeweils bis zu 8 Kohlenstoffatomen,for alkenyl or alkynyl, each optionally substituted by halogen, each having up to 8 carbon atoms,
für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Carboxy, Phenyl (welches gegebenenfalls durch Halogen, Cyano, C,-C4-Alkyl, C,-C4-Halogenalkyl, C,-C4- Alkoxy oder Cr for each optionally one or more times, identically or differently, by halogen, cyano, carboxy, phenyl (which optionally by halogen, cyano, C, -C 4 alkyl, C, -C 4 haloalkyl, C, -C 4 alkoxy or C r
C4-Halogenalkoxy substituiert ist), C^C.j-Alkyl oder C1 -C4-Alkoxy- carbonyl substiuiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,C 4 haloalkoxy is substituted), C ^ C. j -alkyl or C 1 -C 4 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl. Naphthyl oder für Heterocyclyl mit 3 bis 7 Ring- gliedern, von denen mindestens eines für Sauerstoff. Schwefel oder Stick¬ stoff und gegebenenfalls ein oder zwei weitere für Stickstoff stehen, steht. wobei die möglichen Substituenten vorzugsw eise aus der nachstehenden Aufzahlung ausgewählt sindfor phenyl which is optionally mono- or polysubstituted by identical or different substituents. Naphthyl or for heterocyclyl with 3 to 7 ring members, at least one of which for oxygen. Sulfur or nitrogen and optionally one or two more are nitrogen. the possible substituents are preferably selected from the list below
Halogen. Cyano. Nitro. Λmmo Hydroxy, Formyl, Carbow .
l Thiocarbamoyl.Halogen. Cyano. Nitro. Λmmo hydroxy, formyl, carbow. l thiocarbamoyl.
jeweils geradkettiges oder verzweigtes Alkyl. Alkoxy. Alkylthio. Alkyl- sulfinvl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen,each straight-chain or branched alkyl. Alkoxy. Alkylthio. Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms,
leweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxv mit leweils 2 bis 6 Kohlen Stoff atomen.
jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogenalkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiede¬ nen Halogenatomen,each straight-chain or branched alkenyl or alkenyloxv with 1 to 6 carbon atoms each. in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogen- alkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen,each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
jeweils geradkettiges oder verzweigtes Alkylamino, Dialkvlamino, Alkyl¬ carbonyl, Alkylcarbonylox) , Alkoxycarbonyl oder Alkylsulfonvloxy, mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen,in each case straight-chain or branched alkylamino, dialkvlamino, alkylcarbonyl, alkylcarbonylox), alkoxycarbonyl or alkylsulfonyloxy, each having 1 to 6 carbon atoms in the individual alkyl parts,
jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen und/oder geradkettiges oder verzweigtes Halogenalkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 9 gleichen oder verschiedenen Halogenatomen substituiertes, jeweils zweifach verknüpftes Alkylen odereach optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case double-linked alkylene or
Dioxyalkylen mit jeweils 1 bis 6 Kohlenstoffatomen,Dioxyalkylene with 1 to 6 carbon atoms each,
Cvcloalkyl mit 3 bis 6 Kohlenstoffatomen,Cvcloalkyl with 3 to 6 carbon atoms,
Heterocyclyl oder Heterocvcivl-meth\ l mit leweils " bis 7 Ringgliedern v on denen jeweils 1 bis 3 gleiche oder v erschiedene Heteroatome sind - insbesondere Stickstoff Sauerstoff und/oder Schwele! -Heterocyclyl or Heterocvcivl-meth \ l each with " up to 7 ring members, each of which has 1 to 3 identical or different heteroatoms - especially nitrogen, oxygen and / or sulfur! -
oder eine Gruppierung , worin
or a group in which
für Alkvl mit 1 bis 4 Kohlenstoffatomen oder Cvcloalkyl mit 1 bis 6 Kohlenstoffatomen steht undstands for Alkvl with 1 to 4 carbon atoms or Cvcloalkyl with 1 to 6 carbon atoms and
A2 für gegebenenfalls durch Cvano, C,-C4-Alkoxy C,-C4-Alkylthιo, CrC4-Alkylamιno, C,-C2-Dιalkvlamιno, Phenyl, Halogenphenvl Methylphenyl Tπfuormeth\ lphenyl, oder C,-C2-Alkoxyphenyl
substituiertes Alkyl mit 1 bis 4 Kohlenstoff atomen, Alkenyl oder Alkinyl mit jeweils 2 bis 4 Kohlenstoff atomen steht.A 2 for optionally by Cvano, C, -C 4 -alkoxy C, -C 4 -Alkylthιo, C r C 4 -alkylamιno, C, -C 2 -Dιalkvlamιno, phenyl, halophenyl methylphenyl triformeth \ lphenyl, or C, -C 2 alkoxyphenyl substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl each having 2 to 4 carbon atoms.
In den Definitionen sind die gesättigten oder ungesättigten Kohlenwasserstoff¬ ketten, wie Alkyl, Alkandiyl, Alkenyl oder Alkinyl, auch in Verknüpfung mit Heteroatomen, wie in Alkoxy, Alkylthio oder Alkylamino, jeweils geradkettig oder verzweigt.In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
Halogen steht im allgemeinen für Fluor, Chlor, Brom oder lod, vorzugsweise für Fluor, Chlor oder Brom, insbesondere für Fluor oder ChlorHalogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine
Die Erfindung betrifft insbesondere Verbindungen der Formel (I), in welcherThe invention relates in particular to compounds of the formula (I) in which
Ar für jeweils gegebenenfalls substituiertes ortho-, meta- oder para-Phenylen, für Furandiyl, Thiophendiyl, Pyrroldiyl, Pyrazoldiyl, Triazoldiyl, Oxazol- diyl, Isoxazoldiyl, Thiazoldiyl, Isothiazoldiyl, Oxadiazoldiyl, Thiadiazol- diyl, Pyridindiyl (insbesondere Pyridin-2,3-diyl), Pyrimidindiyl, Pyridazin- diyl, Pyrazindiyl, 1,3,4-Triazindiyl oder 1,2,3-Triazindiyl steht, wobei die möglichen Substituenten insbesondere aus der nachstehenden Aufzählung ausgewählt sind:Ar for each optionally substituted ortho-, meta- or para-phenylene, for furandiyl, thiophenediyl, pyrroldiyl, pyrazole diyl, triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, especially pyridinediyl ( -diyl), pyrimidinediyl, pyridazine-diyl, pyrazinediyl, 1,3,4-triazinediyl or 1,2,3-triazinediyl, the possible substituents being selected in particular from the list below:
Fluor, Chlor, Cyano, Methyl, Ethyl, Cyclopropyl, Trifluormethyl. Methoxy. Ethoxy, Methylthio, Methylsulfinyl oder Methylsulfonyl.Fluorine, chlorine, cyano, methyl, ethyl, cyclopropyl, trifluoromethyl. Methoxy. Ethoxy, methylthio, methylsulfinyl or methylsulfonyl.
E für eine der nachstehenden Gruppierungen stehtE represents one of the groupings below
worinwherein
R1 für Wasserstoff, Fluor, Chlor, Brom. Cyano oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, Propyl, Methoxy. Ethoxy, Methylthio, Ethvlthio, Methylamino, Ethylamino oder Dimethylamino steht.
R2 für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils ge¬ gebenenfalls durch Fluor, Chlor, Cyano, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, Methoxy, Ethoxy, Methylamino, Ethyl- amino oder Dimethylamino steht,R 1 for hydrogen, fluorine, chlorine, bromine. Cyano or for methyl, ethyl, propyl, methoxy which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy. Ethoxy, methylthio, Ethvlthio, methylamino, ethylamino or dimethylamino. R 2 stands for hydrogen, amino, hydroxy, cyano or for methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
R1 für Wasserstoff, Cyano oder für jeweils gegebenenfalls durch Fluor,R 1 represents hydrogen, cyano or, in each case optionally by fluorine,
Chlor oder Cyano, substituiertes Methyl, Ethyl n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy, Ethoxy oder Methoxymethyl, für Allyl oder Propargyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methyl, Ethyl, n- oder i-Propyl, Methoxy- oder Ethoxy- sub- stituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl.Chlorine or cyano, substituted methyl, ethyl n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy or methoxymethyl, for allyl or propargyl or for each optionally by fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, methoxy or ethoxy-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.
Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl oder Cyclohexylmethyl steht,Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
für eine Einfachbindung, für Sauerstoff, Schwefel oder für jeweils gege¬ benenfalls durch Fluor, Chlor, Brom, Hydroxy, Methyl, Ethyl, n- oder i- Propyl, Trifluormethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclo¬ hexyl substituiertes Methylen, Dimethylen (Ethan-l ,2-diyl), Ethen-l ,2-diyl, Ethin-l,2-diyl oder eine der nachstehenden Gruppierungenfor a single bond, for oxygen, sulfur or for methylene, dimethylene (optionally substituted by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl) Ethane-1,2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the groupings below
-O-CQ-, -CQ-Q-, -CH2-Q-, -Q-CH2-, -CQ-Q-CH-,-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH:-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2-, -C(R4)=N-O-, -C(R4)=N-O-CH2-, -N(R5)-, -CQ-N(R5)-.-O-CQ-, -CQ-Q-, -CH 2 -Q-, -Q-CH 2 -, -CQ-Q-CH -, -, -CH 2 -Q-CQ-, -Q-CQ- CH 2 -, -Q-CQ-Q-CH : -, -N = N-, -S (O) n -, -CH 2 -S (O) n -, -CQ-, -S (O) n -CH 2 -, -C (R 4 ) = NO-, -C (R 4 ) = NO-CH 2 -, -N (R 5 ) -, -CQ-N (R 5 ) -.
-N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH2-, -CH2-O-N=C(R4)-. -N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH2-, -Q-C(R4)=N-O-CH2-, -N(R5)-C(R )=N-O-CH2-, -O-CH2-C(R4)=N-O-CH:-, -N=N-C(R4)=N-O-CH2-, -T-Ar! - oder -T-Ar' -Q- steht, wobei-N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH 2 -, -CH 2 -ON = C (R 4 ) -. -N (R 5 ) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH 2 -, -QC (R 4 ) = NO- CH 2 -, -N (R 5 ) -C (R) = NO-CH 2 -, -O-CH 2 -C (R 4 ) = NO-CH : -, -N = NC (R 4 ) = NO -CH 2 -, -T-Ar ! - or -T-Ar '-Q-, where
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
Q für Sauerstoff oder Schwefel steht.Q represents oxygen or sulfur.
R4 für Wasserstoff, Cyano, für jeweils gegebenenfalls durch Fluor.R 4 for hydrogen, cyano, each optionally by fluorine.
Chlor, Cyano, Methoxy oder Ethoxy substituiertes Methyl. Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy, Ethoxy, Propoxy. Butoxy, Methylthio. Ethylthio, Propylthio, Butvlthio, Methylamino.Chlorine, cyano, methoxy or ethoxy substituted methyl. Ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy. Butoxy, methylthio. Ethylthio, propylthio, butvlthio, methylamino.
Ethylamino, Propylamino, Dimethylamino oder Diethylamino oder
für jeweils gegebenenfalls durch Fluor, Chlor, Cyano Carbox , Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxy- carbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht, undEthylamino, propylamino, dimethylamino or diethylamino or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine, cyano carbox, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, and
R5 für Wasserstoff, Hydroxy, Cyano oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methoxy oder Ethox substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, 1-, s- oder t-Butyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxy-carbonyl oder Ethoxy-carbonvl substituiertes Cyclopropyl, Cyclobutyl Cvclopentvl oder Cyclohexyl steht,R 5 represents hydrogen, hydroxyl, cyano or methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethox, or each optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl,
Ar' für jeweils gegebenenfalls einfach bis dreifach substituiertes Phenylen, Naphthylen, Furandiyl, Thiophendiyl Oxazoldivl Isoxazoldiyl, Thiazoldiyl, Isothiazoldiyl, 1,2 4-Oxadιazoldιyl, 1 ,3 4- Oxadiazoldiyl, 1,2,4-Thιadιazoldιyl, 1 ,3,4-Thιadιazoldιyl, Pvπ- dindiyl, Pyπmidindiyl, Pyπdazindiyl, Pyrazindiyl, 1 ,2,3-Tπazιndιyl 1,2,4-Tπazιndιyl, 1,3,5-Tπazιndιyl, Oxirandiyl Oxetandiyl Tetra- hydrofurandiyl Perhydropyrandiyl oder Pvrrolidindivl steht wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindAr 'for in each case monosubstituted to trisubstituted phenylene, naphthylene, furandiyl, thiophene diyl oxazole divl isoxazole diyl, thiazole diyl, isothiazole diyl, 1,2 4-oxadiazole diyl, 1, 3 4- oxadiazole diyl, 1,2,4-thiodadazole diyl, 1, 3.4 -Thιadιazoldιyl, Pvπ- dindiyl, Pyπmidindiyl, Pyπdazindiyl, Pyrazindiyl, 1, 2,3-Tπazιndιyl 1,2,4-Tπazιndιyl, 1,3,5-Tπazιndιyl, Oxirandiyl Oxetandiyl Tetrahydrofurandrolidiyl is preferably perhydropyridrolidiyl perhydropyridrodiolid are selected from the following list
Fluor Chlor Brom Cvano Nitro A.mιno Hv drow Formv l Carboxy Carbamo\ l Thiocarbamov l Methv l Eth\ l n- oder i- Propv l, n-, i- s- oder t-Butyl, Methow Ethox\ , n- oder l-Propow Methvlthio Ethylthio n- oder l-Propvlthio Methylsulfinyl Eth\ l- sulfiny 1 Methvlsulfonv 1 oder Eth\ lsulfonvl Tπfluormethv IFluorine Chlorine Bromine Cvano Nitro A.mιno Hv drow Formv l Carboxy Carbamo \ l Thiocarbamov l Methv l Eth \ l n- or i- Propv l, n-, i- s- or t-butyl, Methow Ethox \, n- or l-Propow Methvlthio Ethylthio n- or l-Propvlthio Methylsulfinyl Eth \ l-sulfiny 1 Methvlsulfonv 1 or Eth \ lsulfonvl Tπfluormethv I
Tπfluoreth\ 1 Difluormethoxv Tπfluormethow Difluorchlor-
Tπfluorethow Dιfluormeth\ lthιo Difluorchlormethv lthio Tπfluormethvlthio Tπfluormethv lsulfinv 1 oder Tπfluor ethv 1- sulfon l, , Acet\ l Propionv l Acetvlow Metho\\ carbon l Ethoxv - carbonvl, Meth\ lsulfonylox , Ethvlsulfonvlox Hv droximino- ethvl Hvdroximinoethv l, Methoximinomethv l Ethoxιmιnometh\ l Methoxιmιnoeth\ l Ethoxιmιnoeth\ l oder Cyclopropyl und
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH-,-0-, CH-,-S-Tπfluoreth \ 1 Difluormethoxv Tπfluormethow Difluorchlor- Tπfluorethow Dιfluormeth \ lthιo Difluorchlormethv lthio Tπfluormethvlthio Tπfluormethv lsulfinl 1,, Tπfluor ethv 1- sulfonl lm, methacl \ methion \ meth carbon \ l methoxιmιnoeth \ l ethoxιmιnoeth \ l or cyclopropyl and T for a single bond, for oxygen, sulfur, -CH -, - 0-, CH -, - S-
Methylen, Ethyl en oder Propyl en steht undMethylene, ethylene or propylene stands and
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Stickstoff atom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Tπazolyl, 1,2,4-Tπazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1,2,5-Oxadιazolyl Furyl, Thienyl, 1 ,2-Thιazolyl, 1 ,3-Thιazolyl 1 ,2,3-Thιadιazolyl 1,2,4- Thiadiazolyl, 1,2,5-Thιadιazolyl, 1,3 4-Thιadιazolyl Pyπdyl, Pvπmidyl Pyrazyl, Pyπdazyl, 1,2,3-Tπazyl, 1 ,2,4-Tπazvl 1 ,3,5-Tπazvl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinylfor 1,2,5-oxadiazolyl furyl, thienyl, 1,2-thiazolyl, 1,3-thazazolyl 1,2,3-thizadazolyl 1,2,4 each bonded via a carbon atom and optionally substituted by methyl, methoxy or hydroxy - Thiadiazolyl, 1,2,5-Thιadιazolyl, 1,3 4-Thιadιazolyl Pyπdyl, Pvπmidyl Pyrazyl, Pyπdazyl, 1,2,3-Tπazyl, 1, 2,4-Tπazvl 1, 3,5-Tπazvl, partially or completely hydrogenated thiazolyl or thiazinyl
für gegebenenfalls durch Methyliden, Ethyliden Benzvliden, Acetyl- methyliden, Benzoylmethyliden, Ethoxycarbonvl methyliden oder Methoxy- carbonylmethyliden substituiertes 4-Oxo-l ,3-thιazol-2-ylfor 4-oxo-l, 3-thιazol-2-yl optionally substituted by methylidene, ethylidene, benzvlidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonvl methylidene or methoxycarbonylmethylidene
für jeweils gegebenenfalls durch Methyl oder Ethyl substituiertes gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,for saturated heterocyclyl with 3 to 8 ring members optionally substituted by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach zweifach oder dreifach durch Methvl oder Ethvl substituiertes Imιdazolιdιn-2-\ l Tetrahvdrop πmιdιn-2- yl oder 4,5,6 7-Tetrahydro-l H- l 3-dιazepιn-2-\ l stehtor for Imιdazolιdιn-2- \ l tetrahvdrop πmιdιn-2- yl or 4,5,6 7-tetrahydro-l H- l 3-dιazepιn-2- \ l, which is optionally substituted once or twice by methvl or ethvl
Z für gegebenenfalls einfach bis tunflach durch Tluor C hlor Brom C\ anoZ for optionally simple to flat by Tluor C hlor Brom C \ ano
Hv drow Amino Methow Ethow Metin lthio Eth\ lthιo Methv lsulfinv l Ethv Isulfinv I Meti Isulfonv l Ethv Isulionv 1 (welche leweils gegebenenfalls durch Fluor und'oder Chlor substituiert sind) substituieπes Methv l Ethv l n- oder l-Prop l, n-, I- s- oder t-ButylHv drow Amino Methow Ethow Metin lthio Eth \ lthιo Methv lsulfinv l Ethv Isulfinv I Meti Isulfonv l Ethv Isulionv 1 (which may or may not be substituted by fluorine and / or chlorine) Substituted Methv l Ethv l n- or l-Prop l, n- , I- s- or t-butyl
für jeweils gegebenenfalls einfach bis dreifach durch Fluor, Chlor oder Brom substituiertes Allyl, Crotonyl, 1-Methv l-allvl Propargvl oder 1 - Methyl-propargyl,
für jeweils gegebenenfalls einfach bis sechsfach durch Fluor, Chlor, Brom, Cyano, Carboxy, Phenyl (welches gegebenenfalls durch Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy oder Trifiuormethoxy substituiert ist), Methyl, Ethyl, n- oder i-Propyl, Methoxy- carbonyl oder Ethoxy-carbonyl substiuiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl,for allyl, crotonyl, 1-methvl-allvl propargvl or 1-methyl-propargyl, each optionally monosubstituted to trisubstituted by fluorine, chlorine or bromine, for each optionally one to six times by fluorine, chlorine, bromine, cyano, carboxy, phenyl (which optionally by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ,
für jeweils gegebenenfalls einfach bis dreifach substituiertes Phenyl, Naphthyl, Furyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1 ,2,4-Oxadιazolyl, 1,3,4-Oxadiazolyl, 1 ,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl,for in each case monosubstituted to trisubstituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1,3 , 4-thiadiazolyl,
Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1 ,2,3-Triazinyl. 1 ,2,4- Triazinyl, 1 ,3,5-Triazinyl, Oxiranyl, Oxetanyl, Tetrahydrofuryl, Perhydro- pyranyl, Pyrrolidinyl, Piperidinyl oder Morpholinyl steht, wobei die mög¬ lichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung aus- gewählt sindPyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,3-triazinyl. 1,2,4-triazinyl, 1,3,5-triazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, the possible substituents preferably being selected from the following list
Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl, Thiocarbamoyl, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethyl- sulfonyl , Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifiuormethoxy.Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy.
Difluorchlormethoxy, Trifluorethoxy, Difluormethylthio, Difluorchlor- methylthio, Trifluormethylthio, Trifluormethylsulfinyl oder Trifluormethvl- sulfonvl. Methylamino, Ethylamino, n- oder l-Propylamino, Dimethyl¬ amino, Diethylamino. Acetyl, Propionyl, Acetyloxv , Methoxycarbonyl. Ethoxycarbonyl, Methyl sulfonyloxy oder Ethylsulfonvloxy,Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethyl sulfonvl. Methylamino, ethylamino, n- or l-propylamino, dimethyl¬ amino, diethylamino. Acetyl, propionyl, acetyloxv, methoxycarbonyl. Ethoxycarbonyl, methyl sulfonyloxy or ethylsulfonyloxy,
jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor. Chlor, Methyl, Trifluormethyl, Ethyl, n- oder 1 -Propyl sub¬ stituiertes, |eweιls zweifach verknüpftes Tπmethylen (Propan- l ,3-dιyl). Methylendioxy oder Ethylendioxy,each one or more times, if appropriate, the same or different by fluorine. Chlorine, methyl, trifluoromethyl, ethyl, n- or 1-propyl substituted, two-linked tπmethylene (propane-l, 3-dimyl). Methylenedioxy or ethylenedioxy,
Cyclopropyl. Cyclobutyl, Cyclopentyl oder Cyclohexyl,
oder eine Gruppierung , worin
Cyclopropyl. Cyclobutyl, cyclopentyl or cyclohexyl, or a group in which
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Cyclopropyl oder Cyclobutyl steht undA 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
A2 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Allyl, Propargyl, But-2-en- l -yl, 2-Methyl-prop-l -en-3-yl, Cyanmethyl,A 2 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l -yl, 2-methyl-prop-l -en -3-yl, cyanomethyl,
Methoxymethyl , Ethoxymethyl, Methoxyethyl , Ethoxyethyl , Methylthiomethyl, Ethylthiomethyl, Methylthioethyl, Ethylthioethyl, Dimethylaminomethyl, Dimethylaminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl , Methylbenzyl , Chlorbenzyl . Fluorbenzyl, Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl oder stehtMethoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl. Fluorobenzyl, Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl or stands
Ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I),Compounds of the general formula (I) are very particularly preferred,
in welcherin which
Ar für ortho-Phenylen, Pyridin-2,3-diyl oder Thiophen-2,3-diyl steht,Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
E für eine der nachstehenden Gruppierungen stehtE represents one of the groupings below
^ C ^ ^ C ^ ^ N ^ II II I ,^ C ^ ^ C ^ ^ N ^ II II I,
CH . ι\l , RCH. ι \ l, R
•R ^ FT • R ^ FT
worinwherein
R1 und R" jeweils für Methoxy stehen undR 1 and R "each represent methoxy and
R" für Wasserstoff, Cyano, Methyl. Ethyl n- oder i-Propyl, Methoxy. Ethoxy oder Methoxymethyl steht.R "stands for hydrogen, cyano, methyl. Ethyl n- or i-propyl, methoxy. Ethoxy or methoxymethyl.
G für Sauerstoff oder für jeweils gegebenenfalls durch Fluor, Chlor oderG for oxygen or for each optionally by fluorine, chlorine or
Brom substituiertes Dimethylen (Ethan- 1.2-diyl), Ethen-l,2-diyl oder eine der nachstehenden Gruppierungen
-Q-CQ-, -CQ-Q-, -CH2-Q-, -Q-CH2-, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2-, -C(R4)=N-O-, -C(R4)=N-O-CH2-, -N(R5)-, -CQ-N(R5)-, -N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH2-, -CH2-O-N=C(R4)-, -N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH2-,Bromine-substituted dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or one of the groupings below -Q-CQ-, -CQ-Q-, -CH 2 -Q-, -Q-CH 2 -, -CQ-Q-CH 2 -, -CH 2 -Q-CQ-, -Q-CQ-CH 2 -, -Q-CQ-Q-CH 2 -, -N = N-, -S (O) n -, -CH 2 -S (O) n -, -CQ-, -S (O) n - CH 2 -, -C (R 4 ) = NO-, -C (R 4 ) = NO-CH 2 -, -N (R 5 ) -, -CQ-N (R 5 ) -, -N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH 2 -, -CH 2 -ON = C (R 4 ) -, -N (R 5 ) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH 2 -,
-Q-C(R4)=N-O-CH2-, -N(R5)-C(R4)=N-O-CH2-, -O-CH2-C(R4)=N-O-CH2-, -N=N-C(R4)=N-O-CH2-, -T-Ar1- oder -T-Ar'-Q- steht, wobei-QC (R 4 ) = NO-CH 2 -, -N (R 5 ) -C (R 4 ) = NO-CH 2 -, -O-CH 2 -C (R 4 ) = NO-CH 2 -, -N = NC (R 4 ) = NO-CH 2 -, -T-Ar 1 - or -T-Ar'-Q-, where
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
Q für Sauerstoff oder Schwefel steht,Q represents oxygen or sulfur,
R4 für Wasserstoff, Cyano, Methyl, Eth l oder Cyclopropyl steht undR 4 represents hydrogen, cyano, methyl, Eth 1 or cyclopropyl and
R5 für Wasserstoff, Methyl, Ethyl oder Cyclopropyl steht,R 5 represents hydrogen, methyl, ethyl or cyclopropyl,
Ar' für jeweils gegebenenfalls einfach bis dreifach, gleich oder ver¬ schieden substituiertes Phenylen oder Pyπdindiyl, für jeweils ge¬ gebenenfalls einfach substituiertes Pyπmidindiyl, Pyπdazindiyl, Pyrazindiyl, 1,2,3-Tπazιndιyl, 1 ,2,4-Tπazιndιyl oder 1 ,3,5-Tπa- zindiyl oder für 1 ,2,4-Thιadιazoldιvl, 1 ,3,4-Thιadιazoldιyl, 1,2,4- Oxadiazoldiyl, 1,3,4-Oxadιazoldιyl steht, wobei die möglichen Sub- stituenten vorzugsweise aus der nachstehenden Aufzahlung ausge¬ wählt sindAr 'for in each case monosubstituted to trisubstituted, identically or differently, substituted phenylene or pyπdinediyl, for in each case optionally monosubstituted pyπmidindiyl, pyπdazindiyl, pyrazinediyl, 1,2,3-triazidndyl, 1, 2,4-triazidndyl or 1, 3,5-Tπa- zindiyl or stands for 1, 2,4-Thιadιazoldιvl, 1, 3,4-Thιadιazoldιyl, 1,2,4-oxadiazole diyl, 1,3,4-Oxadιazoldιyl, the possible substituents preferably from of the following payment are selected
Fluor, Chlor, Brom, Cyano, Methv l. Ethyl, n- oder l-Propv l, Cvclo- propyl, Methoxy, Ethoxy, n- oder ι-Propox Methvlthio Ethvlthio n- oder i-Propylthio, Methylsulfinv l Ethylsulfinyl Methvlsulfonv l oder Ethylsulfonyl, Tπfluorm ethv l, Tπfluoreth l, Difluormethoxv Trifiuormethoxy , Difluorchlormethoxv Tπfluorethoxv Difluor- methylthio, Trifluormethvlthio, Difluorchlormethv thio Tπfluor- methylsulfinvl oder Trifluormethyl sulfonvl undFluorine, chlorine, bromine, cyano, methv l. Ethyl, n- or l-Propv l, Cvclopropyl, methoxy, ethoxy, n- or ι-Propox Methvlthio Ethvlthio n- or i-Propylthio, Methylsulfinv l Ethylsulfinylvl Ethylsulfonv l or Ethylsulfonyl, Tπfluormethv l, Trifluoromethox l, Trifluoromethox l , Difluorchlormethoxv Tπfluorethoxv Difluor- methylthio, Trifluormethvlthio, Difluorchlormethvvio Tπfluoromethylsulfinvl or Trifluormethyl sulfonvl and
T für eine Einfachbindung, für Sauerstoff, Schwefel -CH2-0- CH2-S-T for a single bond, for oxygen, sulfur -CH 2 -0- CH 2 -S-
Methylen, Ethylen oder Propylen steht und
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Stickstoff atom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Tetrazolyl,Methylene, ethylene or propylene stands and R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
für jeweils über ein Kohlenstoff atom gebundenes, jeweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1,2,5-Oxadiazolyl,for 1,2,5-oxadiazolyl each bonded via a carbon atom and optionally substituted by methyl, methoxy or hydroxy,
Furyl, Thienyl, 1 ,2-Thiazolyl, 1,3-Thiazolyl, 1 ,2,3-Thiadiazolyl, 1 ,2,4- Thiadiazolyl, 1,2,5-ThiadiazolyI, 1,3,4-Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1,2,4-Triazyl, 1,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,Furyl, thienyl, 1, 2-thiazolyl, 1,3-thiazolyl, 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,2,5-thiadiazolyI, 1,3,4-thiadiazolyl, pyridyl, Pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1,3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyliden, Acetyl- methyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxy- carbonylmethyliden substituiertes 4-Oxo-l ,3-thiazol-2-yl,for 4-oxo-l, 3-thiazol-2-yl optionally substituted by methylidene, ethylidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene,
für jeweils gegebenenfalls durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,for saturated heterocyclyl with 3 to 8 ring members optionally substituted by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imidazolidin-2-yl, Tetrahydropyrimidin-2- yl oder 4,5,6,7-Tetrahydro-lH-l ,3-diazepin-2-yl steht,or represents in each case optionally, mono- or trisubstituted or trisubstituted imidazolidin-2-yl, tetrahydropyrimidin-2-yl or 4,5,6,7-tetrahydro-1H-l, 3-diazepin-2-yl,
Z für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, 1 ,2,4-Thiadiazolyl. 1.3.4-Thιadιazolyl, 1 ,2.4-Oxa- diazolyl, 1 ,3,4-Oxadiazolyl. Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinv . 1 ,2,3-Triazinyl. 1.2,4-TriazinyI oder 1 ,3,5-Triazinyl steht, wobei die mög¬ lichen Substituenten vorzugsweise aus der nachstehenden Aufzählung aus¬ gewählt sindZ for phenyl, 1, 2,4-thiadiazolyl which is optionally monosubstituted to trisubstituted by identical or different substituents. 1.3.4-Thιadιazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl. Pyridinyl, pyrimidinyl, pyridazinyl, pyrazine. 1, 2,3-triazinyl. 1,2,4-triazinyl or 1,3,5-triazinyl, the possible substituents preferably being selected from the list below
Fluor. Chlor. Brom, Cyano, Methyl, Ethyl. n- oder i-Propyl, n-, i-, s- oder t-Butyl. Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propvlthio. Methylsulfinv l, Ethylsulfinyl, Methvlsulfonvl oder Ethyl- sulfonyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifiuormethoxy, Difluorchlormethoxy, Trifluorethoxy, Difluormethylthio, Trifluormethylthio, Difluorchlormethylthio, Trifluormethylsulfinv oder TrifluormethylsulfonyKFluorine. Chlorine. Bromine, cyano, methyl, ethyl. n- or i-propyl, n-, i-, s- or t-butyl. Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio. Methylsulfinv l, ethylsulfinyl, methvlsulfonvl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromethylsifluoromethylsifluoromethylsifluoromethylsulfonyl or trifluoromethyl
Methoxvcarbonyl, Ethoxvcarbonyl,
jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Methylendioxy oder Ethylendioxy,Methoxvcarbonyl, ethoxvcarbonyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case double-linked methylenedioxy or ethylenedioxy,
oder eine Gruppierung , worin
or a group in which
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl,A 1 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
Cyclopropyl oder Cyclobutyl steht undCyclopropyl or cyclobutyl stands and
A" für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Allyl.A "for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl.
Propargyl, But-2-en-l -yl, 2-Methyl-prop- l -en-3-yl, Cyanmethyl,Propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl,
Methoxymethyl , Ethoxymethyl, Methoxyethyl, Ethoxyethyl , Methylthiomethyl, Ethylthiomethyl, Methyl thioethyl, Ethylthioethyl,Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl,
Dimethylaminomethyl, Dimethylaminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl, Chlorbenzyl, Fluorbenzyl, Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl oder stehtDimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl, trifluoromethylbenzyl, benzoyl, chlorobenzoyl or
Eine besonders bevorzugte Gruppe erfindungsgemaßer Verbindungen sind dieienigen Verbindungen der Formel (I),A particularly preferred group of compounds according to the invention are the viable compounds of the formula (I)
in welcherin which
Ar für ortho-Phenylen, Pyridιn-2,3-dιyl oder Thιophen-2,3-dιyl steht,Ar represents ortho-phenylene, pyrid-2,3-dimyl or thiophen-2,3-dimyl,
E für eine der nachstehenden Gruppierungen steht,E represents one of the groupings below,
^ C ^ ^ C ^ ^ N ^ II II I ,^ C ^ ^ C ^ ^ N ^ II II I,
CH . N , RCH. NO
'R HR' 'R H R '
worinwherein
R1 und R2 jeweils für Methoxy stehen,R 1 and R 2 each represent methoxy,
R' für Wasserstoff, Methvl oder Ethvl steht,
G für -O-CH, steht undR 'represents hydrogen, methylene or ethylene, G stands for -O-CH, and
R für jeweils über ein Kohlenstoff atom gebundenes, jeweils gegebenenfalls an einem Stickstoff atom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1,2,5-Oxadiazolyl, Furyl, Thienyl, 1,2-Thiazolyl, 1,3-Thiazolyl, 1 ,2,3-Thiadιazolyl, 1 ,2,4- Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1,2,4-Triazyl, 1,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,for 1,2,5-oxadiazolyl, furyl, thienyl, 1,2-thiazolyl, 1,3-thiazolyl, 1, 2,3-thiadιazolyl, 1 each bonded via a carbon atom and optionally substituted by methyl, methoxy or hydroxy, 2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1,3, 5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyliden, Acetyl- methyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxy- carbonylmethyliden substituiertes 4-Oxo-l,3-thiazol-2-yl,for 4-oxo-l, 3-thiazol-2-yl optionally substituted by methylidene, ethylidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene,
für jeweils gegebenenfalls einfach oder mehrfach durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,for saturated heterocyclyl with 3 to 8 ring members optionally substituted one or more times by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imidazolidin-2-yl. Tetrahvdropyrimidin-2- yl oder 4,5,6,7-Tetrahydro-lH-l ,3-diazepin-2-yl steht,or for imidazolidin-2-yl which is optionally substituted once, twice or three times by methyl or ethyl. Tetrahvdropyrimidin-2-yl or 4,5,6,7-tetrahydro-lH-1,3-diazepin-2-yl,
Z für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl steht, wobei die möglichen Substituenten vorzugs¬ weise aus der nachstehenden Aufzählung ausgewählt sindZ represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below
Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butvl, Methoxy, Ethoxy, n- oder i-Propoxy. Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinvl. Ethylsulfinyl, Methvlsulfonvl oder Ethyl- sulfonyl, Trifluormethyl, Difluormethoxy, Trifiuormethoxy, Difluorchlor- methoxy, Trifluorethoxy, Difluormethylthio, Trifluormethylthio, Difluor- chlormethylthio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl, Methoxy carbonyl, Ethoxycarbonyl,
jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Methylendioxy oder Ethylendioxy,Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butvl, methoxy, ethoxy, n- or i-propoxy. Methylthio, ethylthio, n- or i-propylthio, methylsulfine. Ethylsulfinyl, methvlsulfonvl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, trifluoromethylthio, difluoromethylchloromethyl, trifluoromethylsulfyloxy, trifluoromethylsulfoxy, trifluoromethyl each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case double-linked methylenedioxy or ethylenedioxy,
oder eine Gruppierung , worin
or a group in which
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl,A 1 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
Cyclopropyl oder Cyclobutyl steht undCyclopropyl or cyclobutyl stands and
A" für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Allvl.A "for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Allvl.
Propargyl, But-2-en-l -yl, 2-Methyl-prop- l -en-3-yl, Cyanmethyl,Propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl,
Methoxymethyl , Ethoxymethyl, Methoxyethyl , Ethoxyethyl. Methylthiomethyl, Ethylthiomethyl, Methylthioethyl, Ethylthioethyl,Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl. Methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl,
Dimethylaminomethyl, Dimethylaminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl , Chl orbenzyl , Fluorbenzyl, Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl oder steht.Dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl, trifluoromethylbenzyl, benzoyl, chlorobenzoyl or is.
Eine ebenfalls besonders bevorzugte Gruppe erfindungsgemäßer Verbindungen sind diejenigen Verbindungen der Formel (I),Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
in welcherin which
Ar für ortho-Phenylen, Pyridin-2,3-diyl oder Thiophen-2,3-diyl steht,Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
E für eine der nachstehenden Gruppierungen steht,E represents one of the groupings below,
^ C^ ^ C " ^ N^ II II I ,^ C ^ ^ C "^ N ^ II II I,
CH . iNk - RCH. iNk - R
•R1 ^ R' • R 1 ^ R '
worinwherein
R1 und R2 jeweils für Methoxy stehen,R 1 and R 2 each represent methoxy,
R3 für Wasserstoff, Methyl oder Ethvl steht.
G für -C(R4)=N-O-CH2- steht, wobeiR 3 represents hydrogen, methyl or Ethvl. G represents -C (R 4 ) = NO-CH 2 -, where
R4 für Wasserstoff, Cyano, Methyl, Ethyl oder Cyclopropyl steht,R 4 represents hydrogen, cyano, methyl, ethyl or cyclopropyl,
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Stickstoff atom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
für jeweils über ein Kohlenstoff atom gebundenes, jeweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1,2,5-Oxadiazolyl, Furyl, Thienyl, 1 ,2-Thiazolyl, 1 ,3-Thiazolyl, 1 ,2,3-Thiadiazolyl, 1 ,2,4- Thiadiazolyl, 1,2,5-Thiadiazolyl, 1 ,3,4-Thiadiazolyl, Pyridyl, Pyrimidyl. Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1,2,4-Triazyl, 1,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,for 1,2,5-oxadiazolyl, furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1, 2,3-thiadiazolyl, 1 each bonded via a carbon atom and in each case optionally substituted by methyl, methoxy or hydroxy , 2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1, 3,4-thiadiazolyl, pyridyl, pyrimidyl. Pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1,3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyliden, Acetyl- methyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxy- carbonylmethyliden substituiertes 4-Oxo-l,3-thiazol-2-yl,for 4-oxo-l, 3-thiazol-2-yl optionally substituted by methylidene, ethylidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene,
für jeweils gegebenenfalls durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen.for saturated or optionally substituted methyl or ethyl heterocyclyl with 3 to 8 ring members, one, two or three ring members representing oxygen and / or sulfur.
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imidazolidin-2-yl, Tetrahydropyrimidin-2- yl oder 4,5, 6,7-Tetrahydro- lH- l,3-diazepin-2-yl steht,or stands for imidazolidin-2-yl, tetrahydropyrimidin-2-yl or 4,5,6,7-tetrahydro-1H-l, 3-diazepin-2-yl which is optionally mono-, di- or trisubstituted by methyl or ethyl
Z für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Pyridyl oder Pyrimidyl steht, wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzählung ausgewählt sindZ represents phenyl, pyridyl or pyrimidyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below
Fluor, Chlor, Brom. Cyano. Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinvl, Ethylsulfinyl, Methylsulfonyl oder Ethyl- sulfonvl, Trifluormethyl, Trifluor ethyl, Difluormethoxy, Trifiuormethoxy. Difluorchlormethoxy, Trifluorethoxy, Difiuormethylthio, Trifluormethylthio,
Difluorchlormethylthio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl, Methoxycarbonyl, Ethoxycarbonyl, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl, Ethoximinoethyl, jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluor- methyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Methylen- dioxy oder Ethyl endioxy.Fluorine, chlorine, bromine. Cyano. Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfine, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy. Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, Difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, each optionally one to four times, identically or differently substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl or ethylened, each two-linked .
Eine weiterhin besonders bevorzugte Gruppe erfindungsgemäßer Verbindungen sind diejenigen Verbindungen der Formel (I),Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
in welcherin which
Ar für ortho-Phenylen steht,Ar represents ortho-phenylene,
E für eine der nachstehenden Gruppierungen steht,E represents one of the groupings below,
C C NC C N
II II I ,II II I,
CH . N , RCH. NO
*R1 ^ R * R 1 ^ R
worinwherein
R und R" jeweils für Methoxy stehen,R and R "each represent methoxy,
RΛ für Wasserstoff, Methyl oder Ethyl steht,R Λ represents hydrogen, methyl or ethyl,
G für -T-Ar' -Q- steht, wobeiG represents -T-Ar '-Q-, where
Q für Sauerstoff oder Schwefel steht,Q represents oxygen or sulfur,
Ar1 für 1 ,2,4-Thiadiazoldiyl, 1 ,3,4-ThiadiazoldiyI, 1 ,2,4-Oxadiazoldiyl,Ar 1 for 1, 2,4-thiadiazole diyl, 1, 3,4-thiadiazole diI, 1, 2,4-oxadiazole diyl,
1 ,3.4-Oxadiazoldiyl oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor. Cyano.1, 3,4-oxadiazole diyl or for each optionally single or double, identical or different by fluorine, chlorine. Cyano.
Methyl, Cyclopropyl. Methoxy, Methylthio, Trifluormethyl. Difluor¬ methoxy, Trifiuormethoxy, Difluorchlormethoxy substituiertes. Pyridindiyl, Pyrimidindiyl oder 1 ,3,5-Triazindiyl steht,
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH2-O-, CH-.-S-,Methyl, cyclopropyl. Methoxy, methylthio, trifluoromethyl. Difluor¬ methoxy, Trifiuormethoxy, Difluorchlormethoxy substituted. Pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, T for a single bond, for oxygen, sulfur, -CH 2 -O-, CH -.- S-,
Methylen, Ethyl en oder Propyl en steht undMethylene, ethylene or propylene stands and
R für jeweils über ein Kohlenstoff atom gebundenes, jeweils gegebenenfalls an einem Stickstoff atom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethyl,
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1,2,5-Oxadiazolyl, Furyl, Thienyl, 1 ,2-Thiazolyl, 1 ,3-Thiazolyl, 1 ,2,3-Thiadιazolyl, 1 ,2,4- Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1,2,4-Triazyl, 1 ,3,5-Tπazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,for 1,2,5-oxadiazolyl, furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, 1, 2,3-thiadιazolyl, 1, each bonded via a carbon atom and optionally substituted by methyl, methoxy or hydroxy, 2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1, 3, 5-tπazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyliden, Acetyl- methyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxy- carbonylmethyliden substituiertes 4-Oxo-l ,3-thiazol-2-yl,for 4-oxo-l, 3-thiazol-2-yl optionally substituted by methylidene, ethylidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene,
für jeweils gegebenenfalls durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,for saturated heterocyclyl with 3 to 8 ring members optionally substituted by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imιdazolidιn-2-yl, Tetrahvdropynmιdιn-2- yl oder 4,5,6, 7-Tetrahydro-l H- l ,3-dιazepιn-2- l steht.or for in each case optionally monosubstituted or trisubstituted by methyl or ethyl Imιdazolidιn-2-yl, Tetrahvdropynmιdιn-2- yl or 4,5,6,7-Tetrahydro-l H-l, 3-dιazepιn-2- l.
Z für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor. Chlor. Brom. Cyano, Methyl. Ethyl. n- oder i-Propyl. n-, ι-. s- oder t-Butyl, Trifluormethyl. Methoxv . Ethoxv , n- oder ι-Propo\v . Difluor¬ methoxy, Difluorchlormethoxv , Tπfluorethoxy, Tπfluormethoxv oder jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Methylendioxy oder Ethylendioxy, substituier¬ tes Phenyl, Pyridyl oder Thienyl stehtZ for each optionally single to triple, identical or different by fluorine. Chlorine. Bromine. Cyano, methyl. Ethyl. n- or i-propyl. n-, ι-. s- or t-butyl, trifluoromethyl. Methoxv. Ethoxv, n- or ι-Propo \ v. Difluor¬ methoxy, Difluorchlormethoxv, Tπfluorethoxy, Tπfluormethoxv or each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl or thienyl
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen angegebenen Reste- definitionen gelten sowohl für die Endprodukte der Formel (I) als auch entspre-
chend für die jeweils zur Herstellung benötigten Ausgangsstoffe bzw Zwischen¬ produkteThe general or preferred radical definitions given above apply both to the end products of the formula (I) and to corresponding to the starting materials or intermediate products required for the production
Diese Restedefinitionen können untereinander, also auch zwischen den ange¬ gebenen Bereichen bevorzugter Verbindungen, beliebig kombiniert werdenThese radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds
Beispiele für die erfindungsgemäßen Verbindungen sind in den Tabellen 1 bis 36 aufgeführtExamples of the compounds according to the invention are listed in Tables 1 to 36
Tabelle 1Table 1
( IA - 1 )(IA - 1)
wobei Z1 für die folgenden Substituenten steht
where Z 1 represents the following substituents
Tabelle 2Table 2
( 1A - 2 )
wobei Z für die in Tabelle 1 genannten Substituenten steht.(1A - 2) where Z stands for the substituents mentioned in Table 1.
Tabelle 3Table 3
( IA - 3 )(IA - 3)
wobei Z für die in Tabelle 1 genannten Substituenten stehtwhere Z stands for the substituents mentioned in Table 1
Tabelle 4Table 4
( IA - 4 )(IA - 4)
wobei Z für die in Tabelle 1 genannten Substituenten steht
where Z stands for the substituents mentioned in Table 1
Tabelle 5Table 5
( IA - 5 )(IA - 5)
wobei Z für die in Tabelle 1 genannten Substituenten stehtwhere Z stands for the substituents mentioned in Table 1
Tabelle 6Table 6
( IA - 6 )(IA - 6)
wobei Z für die in Tabelle 1 genannten Substituenten steht
where Z stands for the substituents mentioned in Table 1
Tabelle 7Table 7
( IA - 7 )(IA - 7)
wobei Z für die in Tabelle 1 genannten Substituenten stehtwhere Z stands for the substituents mentioned in Table 1
Tabelletable
( IA - 8 )(IA - 8)
wobei Z für die in Tabelle 1 genannten Substituenten steht
where Z stands for the substituents mentioned in Table 1
Tabelle 9Table 9
( IA - 9 )(IA - 9)
wobei Z für die in Tabelle 1 genannten Substituenten stehtwhere Z stands for the substituents mentioned in Table 1
Tabelle 10Table 10
H3CH 3 C
( IA - 10 )(IA - 10)
wobei Z für die in Tabelle 1 genannten Substituenten stehtwhere Z stands for the substituents mentioned in Table 1
Tabelle 1 1Table 1 1
wobei Z~ für die folgenden Substituenten steht.
where Z ~ stands for the following substituents.
Tabelle 11: FortsetzungTable 11: Continuation
Tabelle 1 1 : Fortsetzung Table 1 1: continued
Tabelle 12Table 12
wobei Zr für die in Tabelle 1 1 genannten Substituenten stehtwhere Zr stands for the substituents listed in Table 1 1
Tabelle 1Table 1
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 14where Z "stands for the substituents mentioned in Table 1 1 Table 14
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht.where Z "stands for the substituents mentioned in Table 1 1.
Tabelle 15Table 15
wobei Z~ für die in Tabelle 1 1 genannten Substituenten stehtwhere Z ~ stands for the substituents mentioned in Table 1 1
Tabelle 16Table 16
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 17where Z "stands for the substituents mentioned in Table 1 1 Table 17
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht. where Z "stands for the substituents mentioned in Table 1 1.
Tabelle 18Table 18
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht.where Z "stands for the substituents mentioned in Table 1 1.
Tabelle 19Table 19
wobei Z~ für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 20where Z ~ stands for the substituents mentioned in Table 1 1 Table 20
wobei Z" für die in Tabelle 1 1 genannten Substituenten stehtwhere Z "stands for the substituents mentioned in Table 1 1
Tabelle 21Table 21
wobei Z" für die in Tabelle 1 1 genannten Substituenten stehtwhere Z "stands for the substituents mentioned in Table 1 1
Tabelle 22Table 22
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 23where Z "stands for the substituents mentioned in Table 1 1 Table 23
wobei Z" für die in Tabelle 1 1 genannten Substituenten stehtwhere Z "stands for the substituents mentioned in Table 1 1
Tabelle 24Table 24
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht where Z "stands for the substituents mentioned in Table 1 1
Tabelle 25Table 25
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 26where Z "stands for the substituents mentioned in Table 1 1 Table 26
wobei Z~ für die in Tabelle 1 1 genannten Substituenten stehtwhere Z ~ stands for the substituents mentioned in Table 1 1
Tabelle 27Table 27
wobei Z" für die in Tabelle 1 1 genannten Substituenten stehtwhere Z "stands for the substituents mentioned in Table 1 1
Tabelle 28Table 28
wobei Z" für die in Tabelle 1 1 genannten Substituenten steht
Tabelle 29where Z "stands for the substituents mentioned in Table 1 1 Table 29
wobei Z~ für die in Tabelle 1 1 genannten Substituenten stehtwhere Z ~ stands for the substituents mentioned in Table 1 1
Tabelle 30Table 30
wobei Z" für die in Tabelle 1 1 genannten Substituenten stehtwhere Z "stands for the substituents mentioned in Table 1 1
Tabelle 31Table 31
wobei Z' für die folgenden Substituenten steht
where Z 'represents the following substituents
Tabelle 32Table 32
wobei Z' für die in Tabelle 31 genannten Substituenten stehtwhere Z 'represents the substituents listed in Table 31
Tabelle 33Table 33
wobei Z " für die in Tabelle 31 genannten Substituenten steht where Z "stands for the substituents mentioned in Table 31
Tabelle 3Table 3
( ID - 4(ID - 4
wobei Z "1 für die in Tabelle 3 1 genannten Substituenten steht
Tabelle 35where Z "1 stands for the substituents mentioned in Table 3 1 Table 35
wobei Z"1 für die in Tabelle 31 genannten Substituenten steht.where Z "1 stands for the substituents mentioned in Table 31.
Tabelle 36Table 36
wobei ZΛ für die in Tabelle 31 genannten Substituenten stehtwhere Z Λ stands for the substituents mentioned in Table 31
Tabelle 37Table 37
( ID - 7 )(ID - 7)
wobei 7S für die in Tabelle 31 genannten Substituenten steht
Tabelle 38where 7S stands for the substituents listed in Table 31 Table 38
(ID- 8 )(ID- 8)
wobei Z für die in Tabelle 31 genannten Substituenten stehtwhere Z stands for the substituents listed in Table 31
Tabelle 39Table 39
(ID- 9 )(ID- 9)
wobei 2 für die in Tabelle 31 genannten Substituenten stehtwhere 2 stands for the substituents mentioned in Table 31
Tabelle 40Table 40
( ID - 10 ) wobei X für die in Tabelle 31 genannten Substituenten steht
Die zur Durchführung des erfindungsgemäßen Verfahrens a) als Ausgangsstoffe benötigten Ketone sind durch die Formel (II) allgemein definiert. In dieser Formel (II) haben Ar, G, R und Z vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungs- gemäßen Verbindungen der Formel (I) als bevorzugt bzw. als insbesondere be¬ vorzugt für Ar, G, R und Z angegeben wurden.(ID - 10) where X represents the substituents listed in Table 31 Formula (II) provides a general definition of the ketones required as starting materials for carrying out process a) according to the invention. In this formula (II), Ar, G, R and Z preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Ar, G, R and Z were specified.
Die Ketone der Formel (II) sind noch nicht bekannt; sie sind als neue Stoffe Gegenstand der vorliegenden Anmeldung.The ketones of the formula (II) are not yet known; as new substances, they are the subject of the present application.
Die Ketone der Formel (II) werden erhalten (Verfahren a-al )), wenn man Carbonsäureamide der allgemeinen Formel (X),The ketones of the formula (II) are obtained (process a-al)) if carboxamides of the general formula (X),
1313
RR
Z Ar . N .Z Ar. N.
G 14 G 1 4
RR
OO
(X)(X)
in welcherin which
Ar, G und Z die oben angegebenen Bedeutungen haben undAr, G and Z have the meanings given above and
R1-"1 und R14 gleich oder verschieden sind und für Alkyl. oder gemeinsam mit demR 1 - "1 and R 14 are the same or different and are for alkyl. Or together with the
Stickstoffatom, an das sie gebunden sind, für einen gegebenenfalls substi¬ tuierten Ring, in dem gegebenenfalls ein oder zwei weitere Ringglieder Heteroatome sind, stehen,Nitrogen atom to which they are attached represent an optionally substituted ring in which one or two further ring members are heteroatoms,
mit einer metall organischen Verbindung der Formel der Formel (XI),with a metal organic compound of the formula of the formula (XI),
R-MR-M
(XI)(XI)
in welcher
R die oben angegebene Bedeutung hat undin which R has the meaning given above and
M für Lithium oder -Mg-X2 steht, wobei X2 für Chlor, Brom, lod oder R steht,M represents lithium or -Mg-X 2 , where X 2 represents chlorine, bromine, iodine or R,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines alipha- tischen, alicyclischen oder aromatischen Kohlenwasserstoffes, wie beispielsweiseoptionally in the presence of a diluent, preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example
Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; oder eines Ethers, wie beispielsweise Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-Amylether, Dioxan, Tetrahydrofuran, 1 ,2- Dimethoxyethan, 1,2-Diethoxyethan oder Anisol, bei Temperaturen von -80 bis +50, vorzugsweise -80 und +25°C, umsetztPetroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; or an ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, at temperatures from -80 to +50, preferably -80 and + 25 ° C, implemented
Die zur Durchfuhrung der erfindungsgemäßen Verfahrens a-al) als Ausgangsstoffe benotigten Amide sind durch die Formel (X) allgemein definiert In dieser Formel (X) haben Ar, G und Z vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Ver- bindungen der Formel (I) als bevorzugt bzw als insbesondere bevorzugt für Ar, G und Z angegeben wurden. R13 und R14 sind gleich oder verschieden und stehen für Alkyl, bevorzugt Methyl, Ethyl, n- oder i-Propyl, oder gemeinsam mit dem S ick stoff atom, an das sie gebunden sind, für einen gegebenenfalls einfach oder mehrfach durch Alkyl, bevorzugt Methyl oder Ethyl, substituierten, drei, vier, fünf, sechs oder siebengliedrigen Ring, in dem gegebenenfalls ein oder zwei weitereThe amides required as starting materials for carrying out the process a-al) according to the invention are generally defined by the formula (X) In this formula (X) Ar, G and Z preferably or in particular have those meanings which have already been associated with the description of the invention Compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, G and Z. R 13 and R 14 are the same or different and stand for alkyl, preferably methyl, ethyl, n- or i-propyl, or together with the nitrogen atom to which they are attached, for an alkyl, optionally one or more times, by alkyl, preferably methyl or ethyl, substituted, three, four, five, six or seven-membered ring, in which one or two more, if appropriate
Ringglieder Heteroatome, vorzugsweise Stickstoff, Sauerstoff oder Schwefel, sindRing members are heteroatoms, preferably nitrogen, oxygen or sulfur
Weiterhin wurde gefunden, daß die Carbonsäureamide der Formel (X) ebenfalls sehr starke fungizide Wirkung zeigenIt has also been found that the carboxamides of the formula (X) likewise have very strong fungicidal activity
Die Carbonsäureamide der Formel (X) sind zum Teil bekannt und/oder können nach bekannten Methoden hergestellt werden (vergleiche z B DE-A 2806562 oder WO-A 9422844)Some of the carboxamides of the formula (X) are known and / or can be prepared by known methods (compare, for example, DE-A 2806562 or WO-A 9422844)
Neu, und auch Gegenstand der vorliegenden Anmeldung sind Carbonsäureamide der Formel (Xa),
New and also the subject of the present application are carboxamides of the formula (Xa),
(Xa)(Xa)
in welcherin which
G' für -O-CH:-, -C(CH,)=N-O- oder -T'-Ar-O- steht, wobeiG 'is -O-CH : -, -C (CH,) = NO- or -T'-Ar-O-, where
Ar für gegebenenfal l s einfach durch Hal ogen substitui ertesAr, if necessary, simply substituted by halogens
Heteroarylen steht,Heteroarylene stands,
T1 für eine Einfachbindung, für Sauerstoff, Schwefel, -CH2-O-, CH:-S- oder für gegebenenfalls substituiertes Alkandiyl steht undT 1 represents a single bond, oxygen, sulfur, -CH 2 -O-, CH : -S- or optionally substituted alkanediyl and
Z4 für gegebenenfalls substituiertes Phenyl steht,Z 4 represents optionally substituted phenyl,
R1 ^ für Wasserstoff oder Alkyl steht,R 1 ^ represents hydrogen or alkyl,
Ru> für gegebenenfalls durch Cycloalkyl. Hvdroxv oder Alkoxy substituiertes Alkyl oder Alkenyl, oder für gegebenenfalls durch Alkvl substituiertes Cvcloalkyl oder für Hydroxy oder Alkoxy steht, oderR u> for optionally by cycloalkyl. Hvdroxv or alkoxy substituted alkyl or alkenyl, or for Cvcloalkyl optionally substituted by Alkvl or for hydroxy or alkoxy, or
R, :v und Rκ' gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für einen gegebenenfalls durch Alkyl substituierten heterocychschen Ring stehen, der noch ein Sauerstoff- oder Stickstoffatom enthaltenR ,: v and R κ 'together with the nitrogen atom to which they are attached represent a heterocyclic ring which may be substituted by alkyl and which still contain an oxygen or nitrogen atom
Die Carbonsäureamide der Formel (Xa) werden erhalten (Verfahren a-a2), wenn man Saurederivate der Formel (XII),
The carboxamides of the formula (Xa) are obtained (process a-a2) if acid derivatives of the formula (XII),
(XII)(XII)
in welcherin which
G und Z4 die oben angegebenen Bedeutungen haben undG and Z 4 have the meanings given above and
X3 für Halogen, Hydroxy, Alkoxy, Alkylthio oder -O-CO-Ar-G-Z steht,X 3 represents halogen, hydroxy, alkoxy, alkylthio or -O-CO-Ar-GZ,
mit einem Amin der allgemeinen Formel (XIII),with an amine of the general formula (XIII),
1616
R HN 15R HN 15
R XIIIR XIII
in welcherin which
R 15 und R 16 ' die oben angegebenen Bedeutungen haben,R 15 and R 16 'have the meanings given above,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines alipha- tischen, alicyclischen oder aromatischen Kohlenwasserstoffes, wie beispielsweise Petrolether oder Toluol, eines halogenierten Kohlenwasserstoffes, wie beispiels¬ weise Dichlormethan, eines Ethers, wie beispielsweise Tetrahydrofuran, eines Ni- triles, wie Acetonitril, eines Amides. wie N,N-Dimethylformamid. eines Esters, wie Essigsäureethylester, eines Sulfoxides, wie Dimethylsulfoxid, eines Sufones, wie Sulfolan. oder eines Amines, wie Pyridin, deren Gemischen mit Wasser oder reinem Wasser bei Temperaturen zwischen -20°C und +200°C, vorzugsweise bei Temperaturen zwischen 0°C und 150°C und gegebenenfalls in Gegenwart eines Saureakzeptors, vorzugsweise einer üblichen anorganischen oder organischen Base wie beispielsweise Natriumhydroxid. Tπethylamin oder Pyridin, umsetzt.
Auch Gegenstand der vorliegenden Anmeldung sind vorzugsweise Carbonsäure¬ amide der Formel (Xa), in welcheroptionally in the presence of a diluent, preferably an aliphatic, alicyclic or aromatic hydrocarbon such as petroleum ether or toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as tetrahydrofuran, a nitrile such as acetonitrile or an amide . such as N, N-dimethylformamide. an ester such as ethyl acetate, a sulfoxide such as dimethyl sulfoxide, a Sufone such as sulfolane. or an amine such as pyridine, their mixtures with water or pure water at temperatures between -20 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 150 ° C and optionally in the presence of an acid acceptor, preferably a conventional inorganic or organic base such as sodium hydroxide. Tπethylamin or pyridine, implemented. The present application also preferably relates to carboxylic acid amides of the formula (Xa) in which
G1 für -O-CH2-, -C(CH3)=N-O- oder -T'-Ai^-O- steht, wobeiG 1 represents -O-CH 2 -, -C (CH 3 ) = NO- or -T'-Ai ^ -O-, where
Ar für 1,2,4-Oxadiazoldiyl, 1,3,4-Oxadιazoldιyl, 1,2,4-Thιadιazoldιyl, 1,3,4-Thιadιazoldιyl oder für gegebenenfalls einfach durch Halogen substituiertes Pyrimidindiyl oder 1,3,5-Triazιndiyl steht,Ar stands for 1,2,4-oxadiazole diyl, 1,3,4-oxadiazoldionyl, 1,2,4-thioadazoleionyl, 1,3,4-thioadazoleionyl or for pyrimidinediyl or 1,3,5-triazide diyl which is optionally monosubstituted by halogen ,
T1 für eine Einfachbindung, für Sauerstoff, Schwefel, -CH---, -CH-,- CH,-, -CH2-O- oder -CH2-S- steht undT 1 stands for a single bond, for oxygen, sulfur, -CH ---, -CH -, - CH, -, -CH 2 -O- or -CH 2 -S- and
Z4 für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindZ 4 for phenyl which is monosubstituted to trisubstituted identically or differently in each case, the possible substituents preferably being selected from the following list
Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, I-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methvlsulfonvl oder Ethyl- sulfonyl, Trifluormethyl, Tπfluorethyl, Difluormethoxy, Trifiuormethoxy.Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methvlsulfonvl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy.
Difluorchlormethoxy, Trifluorethoxy, Difiuormethvlthio Tnf.uormethvl.hio Difluorchlormethylthio, Tπfluormethylsulfinv l oder Tπfluormethvlsulfonvl Methoxycarbonyl, Ethoxycarbonyl,Difluorochlormethoxy, Trifluorethoxy, Difiuormethvlthio Tnf.uormethvl.hio Difluorchlormethylthio, Tπfluormethylsulfinv l or Tπfluormethvlsulfonvl methoxycarbonyl, ethoxycarbonyl,
leweils gegebenenfalls einfach bis vierfach, gleich oder v erschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethvl substituiertes, teweils zweifach verknüpftes Methylendioxy oder Ethylendioxy,in each case optionally up to four times, identical or different, substituted by fluorine, chlorine, methyl, trifluoromethyl or Ethvl, in some cases doubly linked methylenedioxy or ethylenedioxy,
oder eine Gruppierung . worin
A3 für Methyl, Ethyl, n- oder i-Propyl, n-, 1-, s- oder t-Butyl, Cyclopropyl oder Cyclobutyl steht undor a grouping. wherein A 3 represents methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, cyclopropyl or cyclobutyl and
A4 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Allyl, Propargyl, But-2-en-l-yl, 2-Methyl-prop-l -en-3-yl, Cyanmethyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Ethoxyethyl ,A 4 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-ene -3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,
Methylthiom ethyl, Ethylthiomethyl, Methylthioethyl, Ethylthioethyl, Dimethylaminomethyl, Dimethylaminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl, Chlorbenzyl , Fluorbenzyl, Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl oder Fluorbenzoyl stehtMethylthiom ethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl, trifluoromethylbenzyl, benzoyl, chlorobenzoyl or fluorobenzoyl
R1 " für Wasserstoff oder Methyl, Ethyl, n- oder i-Propyl, n-, 1-, s- oder t-Butvl steht,R 1 "represents hydrogen or methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butylene,
R16 für Methyl, Cyclopropylmethyl, Hydroxy, Methoxy, Ethoxy oder für gege¬ benenfalls durch Carboxy, Hydroxy oder Methoxy substituiertes Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, 1-, 2- oder 3-Pentyl, 1-, 2- oder 3-R 16 for methyl, cyclopropylmethyl, hydroxy, methoxy, ethoxy or for ethyl which is optionally substituted by carboxy, hydroxy or methoxy, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2 - or 3-pentyl, 1-, 2- or 3-
Hexyl, 1-, 2-, 3- oder 4-Heptyl, Allyl, oder für gegebenenfalls durch Methyl substituiertes Cyclopropyl, Cyclobutyl , Cyclopentyl oder Cyclohexyl steht, oderHexyl, 1-, 2-, 3- or 4-heptyl, allyl, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by methyl, or
R! und R16 gemeinsam mit dem Stickstoff atom, an das sie gebunden sind, einen Pvrrohdin-, Pipeπdin-, N"-Methvlpιperazιn- oder Morpholinπng bildenR ! and R 16 together with the nitrogen atom to which they are bound form a Pvrrohdin-, Pipeπdin-, N "-Methvlpιperazιn- or Morpholinπng
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens a-a2) zur Herstellung der Carbonsäureamide der Formel (Xa) al s Ausgangsstoffe benotigten Sauredeπvate sind durch die Formel (XII) allgemein definiert In dieser Formel (XII) haben G1 und Z4 vorzugsweise bzw insbesondere dieienigen Bedeutungen die bereits im Zusammenhang mit der Beschreibung der erfindungsgemaßen Ver¬ bindungen der Formel (I) als bevorzugt bzw als insbesondere bevorzugt für G1 und Z4 angegeben wurden XΛ steht für Halogen, vorzugsweise Chlor Hvdroxv. Alkoxy, vorzugsweise Methoxv oder Ethoxy, Alkylthio. vorzugsweise Methylthio. Ethvlthio oder Benzylthio oder für -O-CO-(o-C H )-G!-Z4
Die Säurederivate der Formel (XII) sind bekannt und/oder können nach an sich be¬ kannten Verfahren hergestellt werden (vgl. z. B. EP-A 493711)The acid derivatives used to carry out process a-a2) according to the invention for the preparation of the carboxamides of the formula (Xa) as starting materials are generally defined by the formula (XII). In this formula (XII), G 1 and Z 4 preferably or in particular have the relevant meanings X Λ stands for halogen, preferably chlorine Hvdroxv, which have already been given in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for G 1 and Z 4 . Alkoxy, preferably methoxv or ethoxy, alkylthio. preferably methylthio. Ethvlthio or Benzylthio or for -O-CO- (oC H) -G ! -Z 4 The acid derivatives of the formula (XII) are known and / or can be prepared by processes known per se (cf., for example, EP-A 493711)
Die zur Durchführung des erfindungsgemäßen Verfahrens a-a2) zur Herstellung der Carbonsäureamide der Formel (Xa) weiterhin als Ausgangsstoffe benötigten Amine sind durch die Formel (XIII) allgemein definiert In dieser Formel (XIII) haben R15 und R16 vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der Carbonsäureamide der Formel (Xa) als bevorzugt bzw als insbesondere bevorzugt für R15und R16 angegeben wurdenFormula (XIII) provides a general definition of the amines required as starting materials for carrying out process a-a2) for the preparation of the carboxamides of the formula (Xa). In this formula (XIII) R 15 and R 16 preferably or in particular have those Meanings which have already been given in connection with the description of the carboxamides of the formula (Xa) as preferred or as particularly preferred for R 15 and R 16
Die Amine der Formel (XIII) sind bekannte SynthesechemikalienThe amines of the formula (XIII) are known synthetic chemicals
Die zur Durchfuhrung der erfindungsgemaßen Verfahrens a-al) zur Herstellung der Ketone der Formel (II) weiterhin als Ausgangsstoffe benotigten metallorganischen Verbindungen sind durch die Formel (XI) allgemein definiert. In dieser Formel (XI) hat R vorzugsweise bzw. insbesondere diejenige Bedeutung, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen derFormula (XI) provides a general definition of the organometallic compounds which are further required as starting materials for carrying out process a-al) according to the invention for the preparation of the ketones of the formula (II). In this formula (XI), R preferably or in particular has the meaning which has already been associated with the description of the compounds of the invention
Formel (I) als bevorzugt bzw. als insbesondere bevorzugt für R angegeben wurde M steht für Lithium oder -Mg-X2, wobei X2 für Chlor, Brom, lod oder R stehtFormula (I) was given as preferred or as particularly preferred for R M stands for lithium or -Mg-X 2 , where X 2 stands for chlorine, bromine, iodine or R.
Die metallorganischen Verbindungen der Formel (XI) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl z B J Org Chem , 1962, 27, 1216, Synth Comm., 1982, 12, 23 1 , J Org Chem 1971 , 36,The organometallic compounds of the formula (XI) are known and / or can be prepared by processes known per se (see, for example, BJ Org Chem, 1962, 27, 1216, Synth Comm., 1982, 12, 23 1, J Org Chem 1971, 36,
1053, J Org Chem Vol 45, No 20, 1980, Seite 4040, J C S Chem Commun , 1983, 49, J Org Chem., 50, 1985, 662, Angew Chem , Int Ed 1965, 4, 1077, Chem Ber , 1974, 107, 367, Chem Ber , 125, 7, 1992, 1641 , Chem Pharm Bull , 34, 1986, 4916, j am Chem Soc. ( 1989), 1 1 1 (4), 1381 -1392)1053, J Org Chem Vol 45, No 20, 1980, page 4040, JCS Chem Commun, 1983, 49, J Org Chem., 50, 1985, 662, Angew Chem, Int Ed 1965, 4, 1077, Chem Ber, 1974 , 107, 367, Chem Ber, 125, 7, 1992, 1641, Chem Pharm Bull, 34, 1986, 4916, j am Chem Soc. (1989), 1 1 1 (4), 1381 -1392)
Steht R für Pyrrolyl, Imidazolyl, Pyrazolyl, Tπazolyl oder Tetrazolyl, ist es zweckmäßig, die NH-Gruppierung durch Umsetzung mit einem ortho- Ameisensaureester zu schützen, und nach der oben beschriebenen Umsetzung, die Schutzgruppe nach üblichen Methoden wieder abzuspalten (Vergleiche auch die Herstellungsbeispiele )
Die Ketone der Formel (II) werden auch erhalten (Verfahren a-bl)), wenn man Carbonsaurenitπle der allgemeinen Formel (XIV),If R stands for pyrrolyl, imidazolyl, pyrazolyl, tπazolyl or tetrazolyl, it is expedient to protect the NH group by reaction with an ortho-formic acid ester and, after the reaction described above, to split off the protective group again using customary methods (also compare the preparation examples ) The ketones of the formula (II) are also obtained (process a-bl)) if carbonsaurenitπle of the general formula (XIV),
Z .Ar, G CNZ .Ar , G CN
XIVXIV
in welcherin which
Ar, G und Z die oben angegebenen Bedeutungen haben,Ar, G and Z have the meanings given above,
mit einer oben bereits im Zusammenhang mit dem erfindungsgemaßen Verfahren a-al ) zur Herstellung der Ketone der Formel (II) beschriebenen, metallorganischen Verbindung der Formel (XI),with an organometallic compound of the formula (XI) already described above in connection with the process a-al) according to the invention for the preparation of the ketones of the formula (II),
gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines ahpha- tischen, alicyclischen oder aromatischen Kohlenwasserstoffes, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decahn, oder eines Ethers, wie beispielsweise Diethylether, Dnsopropylether, Methyl -t-butyl ether, Methyl-t-Amvl ether, Dioxan, Tetrahvdrofuran, 1 ,2- Dimethoxvethan, 1 ,2-Dιethoxvethan oder Anisol bei Temperaturen von -80 bisoptionally in the presence of a diluent, preferably an ahphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decahn, or an ether, such as, for example, diethyl ether, dnsopropyl ether, methyl -t -butyl ether, methyl-t-amvl ether, dioxane, tetrahvdrofuran, 1, 2-dimethoxvethane, 1, 2-dιethoxvethane or anisole at temperatures from -80 to
-"- 0 vorzugsweise -80 und +25°C umsetzt- "- 0 preferably -80 and + 25 ° C implemented
Die zur Durchfuhrung der erfindungsgemaßen \ erfahrens a-b l ) als usgangsstofte benotigten Carbonsaurenitπle sind durch die Formel (XIV) allgemein definiert In dieser Formel (XIV) haben Ar, G und Z vorzugsweise bzw insbesondere dieienigen Bedeutungen die bereits im Zusammenhang mit der Beschreibung der erfindungsgemaßen Verbindungen der Formel (I) als bevorzugt bzw als ins¬ besondere bev orzugt für Ar G und Z angegeben wurden
Die Carbonsaurenitrile der Formel (XIV) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. z B. EP-A 278 595 oder J. Org Chem. (1982), 47(8), 1546-55)The formula (XIV) provides a general definition of the carboxylic acid nitrogens required as starting materials for carrying out the process according to the invention from l). In this formula (XIV), Ar, G and Z preferably or in particular have the meanings already given in connection with the description of the compounds according to the invention of the formula (I) have been indicated as preferred or as particularly preferred for Ar G and Z. The carboxylic acid nitriles of the formula (XIV) are known and / or can be prepared by processes known per se (cf., for example, EP-A 278 595 or J. Org Chem. (1982), 47 (8), 1546-55)
Die Ketone der Formel (II) werden auch erhalten (Verfahren a-cl)), wenn mann Halogenverbindungen der allgemeinen Formel (XV),The ketones of the formula (II) are also obtained (process a-cl)) if halogen compounds of the general formula (XV)
z-G ^Ar-χ4 (XV) z - G ^ Ar -χ 4 (XV)
in welcherin which
Ar, G und Z die oben angegebenen Bedeutungen haben undAr, G and Z have the meanings given above and
X4 für Halogen steht,X 4 represents halogen,
mit z B Magnesiumspänen oder Butyllithium in allgemein üblicher Art undwith eg magnesium shavings or butyllithium in a generally customary manner and
Weise in die entsprechenden metallorganischen Derivate überfuhrt und diese dann mit einem Nitril der Formel (XVI),Converted into the corresponding organometallic derivatives and then with a nitrile of the formula (XVI),
R-CN (XVI)R-CN (XVI)
in welcherin which
R die oben angegebene Bedeutung hat,R has the meaning given above,
oder einem A id der Formel (XVII),or an A id of the formula (XVII),
RR
R-N ( XVII )R-N (XVII)
\\
R'R '
in welcherin which
R die oben angegebene Bedeutung hat und
R und R gleich oder verschieden sind und für Alkyl, oder gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für einen gegebenenfalls substituierten Ring, in dem gegebenenfalls ein oder zwei weitere Ringglieder Heteroatome sind, stehen,R has the meaning given above and R and R are identical or different and stand for alkyl, or together with the nitrogen atom to which they are attached, for an optionally substituted ring in which one or two further ring members are optionally heteroatoms,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines alipha- tischen, alicyclischen oder aromatischen Kohlenwasserstoffes, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; oder eines Ethers, wie beispielsweise Diethylether, Diisopropylether, Methyl -t-buty lether, Methyl-t-Amylether, Dioxan, Tetrahydrofuran, 1,2- Dimeth- oxyethan, 1,2-Diethoxyethan oder Anisol, bei Temperaturen von -80 bis +50, vorzugsweise -80 und +25°C, umsetztoptionally in the presence of a diluent, preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; or an ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, at temperatures from -80 to + 50, preferably -80 and + 25 ° C, implemented
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens a-cl ) als Ausgangsstoffe benötigten Halogenverbindungen sind durch die Formel (XV) allgemein definiert In dieser Formel (XV) haben Ar, G und Z vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt bzw als ins¬ besondere bevorzugt für Ar, G und Z angegeben wurdenThe halogen compounds required as starting materials for carrying out the process a-cl) according to the invention are generally defined by the formula (XV). In this formula (XV) Ar, G and Z preferably or in particular have those meanings which have already been associated with the description of the invention Compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, G and Z.
Die Halogenverbindungen der Formel (XV) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl z B Synthesis 1981 , (2), 1 17, EP-A 525 516, EP-A 585 751 , Bull Korean Chem Soc ( 1989), 10(4), 397-400.The halogen compounds of the formula (XV) are known and / or can be prepared by processes known per se (see, for example, Synthesis 1981, (2), 1 17, EP-A 525 516, EP-A 585 751, Bull Korean Chem Soc (1989), 10 (4), 397-400.
Synthesis ( 1987), ( 10), 951-3)Synthesis (1987), (10), 951-3)
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens a-cl ) zur Herstellung der Ketone der Formel (II) weiterhin als Ausgangsstoffe benotigten Nitπle oder Amide sind durch die Formeln (XVI) bzw (XVII) allgemein definiert In diesen Formeln (XVI) bzw (XVII) hat R vorzugsweise bz insbesondere diejenige Be¬ deutung, die bereits im Zusammenhang mit der Beschreibung der erfindungsgema¬ ßen Verbindungen der Formel (I) als bevorzugt bzw als insbesondere bevorzugt für R angegeben wurde In Formel (XVII) sind R1 und R1 K gleich oder verschieden und stehen für Alkyl, bevorzugt Methyl, Ethyl, n- oder i-Propyl, oder gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für einen gegebenenfalls einfach oder mehrfach durch Alkyl, bevorzugt Methyl oder Ethyl. substituierten, drei, vier, fünf, sechs oder siebengliedrigen Ring, in dem
gegebenenfalls ein oder zwei weitere Ringglieder Heteroatome, vorzugsweise Stickstoff, Sauerstoff oder Schwefel, sind.The formulas (XVI) and (XVII) which are generally required as starting materials for carrying out the process a-cl) according to the invention for the preparation of the ketones of the formula (II) are generally defined by the formulas (XVI) and (XVII) in these formulas (XVI) and (XVII) R preferably or in particular the meaning which has already been given as preferred or as particularly preferred for R in connection with the description of the compounds of the formula (I) according to the invention. In formula (XVII), R 1 and R 1 K are identical or different and stand for alkyl, preferably methyl, ethyl, n- or i-propyl, or together with the nitrogen atom to which they are attached, for an optionally single or multiple alkyl, preferably methyl or ethyl. substituted, three, four, five, six or seven-membered ring in which optionally one or two further ring members are heteroatoms, preferably nitrogen, oxygen or sulfur.
Die Nitrile der Formel (XVI) und die Amide der Formel (XVTI) sind bekannte organische SynthesechemikalienThe nitriles of the formula (XVI) and the amides of the formula (XVTI) are known organic synthetic chemicals
Die Ketone der Formel (II) können auch erhalten werden, wenn man aromatischeThe ketones of the formula (II) can also be obtained if aromatic
Verbindungen der allgemeinen Formel (XVIII),Compounds of the general formula (XVIII),
\ /Ar (XVIII)\ / Ar (XVIII)
GG
in welcherin which
Ar, G und Z die oben angegebenen Bedeutungen haben,Ar, G and Z have the meanings given above,
mit einem Säurechlorid der Formel (XIX),with an acid chloride of the formula (XIX),
R-COC1 (XIX)R-COC1 (XIX)
in welcherin which
R die oben angegebene Bedeutung hat,R has the meaning given above,
nach üblichen Methoden (Friedel-Crafts-Reaktion). vergleiche z B DE-A 25557956, umsetzt,using conventional methods (Friedel-Crafts reaction). compare e.g. DE-A 25557956, implemented,
oderor
wenn man die weiter oben beschriebenen Halogenverbindungen der allgemeinen Formel (XV), mit z. B. Magnesiumspänen oder Butyllithium in allgemein üblicher Art und Weise in die entsprechenden metallorganischen Derivate überfuhrt, und diese dann mit einem Aldehyd der Formel (XX),if the halogen compounds of the general formula (XV) described above, with z. B. magnesium shavings or butyllithium are converted into the corresponding organometallic derivatives in a generally customary manner, and these are then converted with an aldehyde of the formula (XX),
R-CHO (XX)
in welcherR-CHO (XX) in which
R die oben angegebene Bedeutung hat,R has the meaning given above,
in allgemein üblicher Art und Weise (z B "Grignard-Reaktion") zu den Alkoholen der Formel (XXI),in a generally customary manner (for example "Grignard reaction") to the alcohols of the formula (XXI),
-Ar ^ R-Ar ^ R
(XXI)(XXI)
HOHO
in welcherin which
Ar, G, R und Z die oben angegebenen Bedeutungen haben,Ar, G, R and Z have the meanings given above,
umsetzt (vergleiche auch z. B. DE-A 2 557 956), und diese dann nach allgemein üblichen Methoden oxidiertimplemented (see also, for example, DE-A 2 557 956), and these were then oxidized using generally customary methods
Die zur Durchführung des erfindungsgemäßen Verfahrens b) als Ausgangsstoffe benötigten Nitrile sind durch die Formel (IV) allgemein definiert In dieser Formel (IV) haben Ar, E, G und Z vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungs¬ gemaßen Verbindungen der Formel (I) als bevorzugt bzw als insbesondere be- vorzugt für Ar, E, G und Z angegeben wurdenThe nitriles required as starting materials for carrying out process b) according to the invention are generally defined by the formula (IV). In this formula (IV) Ar, E, G and Z preferably or in particular have those meanings which have already been described in connection with the description of the invention ¬ According to compounds of formula (I) as preferred or as particularly preferred for Ar, E, G and Z have been given
Die Nitrile der Formel (IV) sind teilweise bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl z B EP-A 528 68 1. vergleiche auch die Herstellungsbeispiele)Some of the nitriles of the formula (IV) are known and / or can be prepared by processes known per se (cf. for example EP-A 528 68 1. also compare the preparation examples).
Neu, und auch Gegenstand der vorliegenden Anmeldung sind die Nitrile dei allgemeinen Formel (IVa),New, and also the subject of the present application are the nitriles of the general formula (IVa),
G N (IVa) G N (IVa)
RR
in welcher
Ar, G, RJ und Z die oben angegebenen Bedeutungen haben.in which Ar, G, R J and Z have the meanings given above.
Die Nitrile der allgemeinen Formel (IVa) werden erhalten (Verfahren b-1), wenn man Halogenmethylverbindungen der Formel (XXII),The nitriles of the general formula (IVa) are obtained (process b-1) if halomethyl compounds of the formula (XXII),
in welcherin which
Ar und R" die oben angegebenen Bedeutungen haben undAr and R "have the meanings given above and
X""1 für Halogen steht,X "" 1 represents halogen,
mit einer Hydroxyverbindung der allgemeinen Formel (XXIII), (XXIV) oderwith a hydroxy compound of the general formula (XXIII), (XXIV) or
(XXV),(XXV),
(XXIII) (XXIV) (XXV)(XXIII) (XXIV) (XXV)
in welchenin which
R4 und Z die oben angegebenen Bedeutungen haben,R 4 and Z have the meanings given above,
gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines Ethers, wie Tetrahydrofuran. eines Ketons. wie Aceton. eines Nitrils, wie Acetonitril. eines Amids, wie N,N-Dimethvlformamid oder eines Sulfoxids, wieoptionally in the presence of a diluent, preferably an ether, such as tetrahydrofuran. of a ketone. like acetone. a nitrile such as acetonitrile. an amide such as N, N-dimethylformamide or a sulfoxide such as
Dimethylsulfoxid und gegebenenfalls in Gegenwart eines Saureakzeptors, vorzugsweise eines Alkalimetallhydrides, -hydroxides oder -carbonates, wie beispielsweise Natriumhydrid, Natriumhydroxid oder Kaliumcarbonat bei Temperaturen von -20 bis 120°C umsetzt.Dimethyl sulfoxide and optionally in the presence of an acid acceptor, preferably an alkali metal hydride, hydroxide or carbonate, such as sodium hydride, sodium hydroxide or potassium carbonate at temperatures from -20 to 120 ° C.
Die zur Durchführung des erfindungsgemäßen Verfahrens b-1) als Ausgangsstoffe benotigten Halogenmethylverbindungen sind durch die Formel (XXII) allgemein
definiert In dieser Formel (XXII) haben Ar und R3 vorzugsweise bzw insbe¬ sondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschrei¬ bung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt bzw als insbesondere bevorzugt für Ar und R3 angegeben wurdenFormula (XXII) generalizes the halomethyl compounds required as starting materials for carrying out process b-1) according to the invention In this formula (XXII), Ar and R 3 preferably or in particular have those meanings which have already been given as preferred or as particularly preferred for Ar and R 3 in connection with the description of the compounds of the formula (I) according to the invention
Die Halogenmethylverbindungen der Formel (XXII) sind noch nicht bekannt, sie sind als neue Stoffe Gegenstand der vorliegenden AnmeldungThe halomethyl compounds of the formula (XXII) are not yet known; they are the subject of the present application as new substances
Die Halogenmethylverbindungen der Formel (XXII) werden erhalten (Verfahren b- 2), wenn man Methylverbindungen der allgemeinen Formel (XXVI),The halomethyl compounds of the formula (XXII) are obtained (process b-2) if methyl compounds of the general formula (XXVI),
/Ar CN / Ar CN
H3C N (XXVI) H 3 CN (XXVI)
R3 R 3
in welcherin which
Ar und RJ die oben angegebenen Bedeutungen haben,Ar and R J have the meanings given above,
mit einem üblichen Halogenierungsmittel , wi e z B Brom, Chlor, N- Bromsuccinimid oder N-Iodsuccinimid, gegebenenfalls in Gegenwart eines Verdünnungsmittels, vorzugsweise eines aliphatischen, alicyclischen oder aromatischen Kohlenwasserstoffes, wie beispielsweise Hexan oder Benzol, oder eines halogenierten Kohlenwasserstoffes, wie beispielsweise Tetrachlormethan, und gegebenenfall s i n Gegenwart ei nes Radikal bi l dners w i e bei spi el swei se Benzoylperoxid oder Azodiisobutyronitπl, gegebenenfalls unter Bestrahlung mit UV-Licht, bei einer Temperatur von -20 bis 120°C, umsetztwith a conventional halogenating agent, such as bromine, chlorine, N-bromosuccinimide or N-iodosuccinimide, optionally in the presence of a diluent, preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as, for example, hexane or benzene, or a halogenated hydrocarbon, such as, for example, carbon tetrachloride, and, if appropriate, the presence of a radical, such as benzoyl peroxide or azodiisobutyronitol, optionally under irradiation with UV light, at a temperature of from -20 to 120 ° C.
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens b-2 ) als Ausgangsstoffe benotigten Methvlverbindungen sind durch die Formel (XX\T ) allgemein definiert In dieser Formel (XXVI) haben Ar und R" vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemaßen Verbindungen der Formel (I ) als bevorzugt bzw als ms- besondere bevorzugt für Ar und R1 angegeben wurden
Die Methylverbindungen der Formel (XXVI) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vergleiche Org Synth Coll Vol 1955, 608)That of the inventive method for carrying out b-2) required as starting materials Methvlverbindungen are represented by the formula (XX \ T) provides a general definition In this formula (XXVI), Ar and R "is preferably or in particular the j enigen meanings that already in connection with Description of the compounds of formula (I) according to the invention as preferred or as ms-particularly preferred for Ar and R 1 The methyl compounds of the formula (XXVI) are known and / or can be prepared by processes known per se (see Org Synth Coll Vol 1955, 608)
Die zur Durchfuhrung des erfindungsgemäßen Verfahrens b-1) weiterhin als Aus- gangsstoffe benötigten Hydroxyverbindungen sind jeweils durch die FormelnThe hydroxy compounds required as starting materials for carrying out process b-1) according to the invention are in each case represented by the formulas
(XXIII), (XXIV) oder (XXV) allgemein definiert In diesen Formeln (XXIII), (XXIV) oder (XXV) haben R4 und Z vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungs¬ gemaßen Verbindungen der Formel (I) als bevorzugt bzw als insbesondere be- vorzugt für R4 und Z angegeben wurden(XXIII), (XXIV) or (XXV) generally defined In these formulas (XXIII), (XXIV) or (XXV) R 4 and Z preferably or in particular have those meanings which are already in connection with the description of the compounds according to the invention of the formula (I) as being preferred or as being particularly preferred for R 4 and Z.
Die Hydroxyverbindungen der Formeln (XXIII), (XXIV) oder (XXV) sind bekannte Synthesechemikalien und/oder können nach an sich bekannten Verfahren hergestellt werdenThe hydroxy compounds of the formulas (XXIII), (XXIV) or (XXV) are known synthetic chemicals and / or can be prepared by processes known per se
Die weiterhin zur Durchfuhrung des erfindungsgemaßen Verfahrens b) als Aus- gangsstoffe benotigten bifunktionellen Alkylenverbindungen sind durch die FormelThe bifunctional alkylene compounds which are also required as starting materials for carrying out process b) according to the invention are represented by the formula
(V) allgemein definiert In dieser Formel (V) steht R6 für Amino oder -SH, R7 für(V) generally defined In this formula (V) R 6 stands for amino or -SH, R 7 stands for
Amino, -COOR8 oder -CH(OR9)2, wobei R8 für Wasserstoff oder Alkyl, bevorzugtAmino, -COOR 8 or -CH (OR 9 ) 2 , where R 8 is preferably hydrogen or alkyl
Methyl oder Ethyl steht und R9 für Alkyl bevorzugt Methyl oder Ethyl steht, undIs methyl or ethyl and R 9 is alkyl preferably methyl or ethyl, and
A für gegebenenfalls substituiertes, geradkettiges oder verzweigtes Alkylen steht Stehen R6 und R7 gleichzeitig für Amino, steht A bevorzugt für geradkettiges oder verzweigtes Alkylen mit 2 bis 10 Kohlenstoffatomen, insbesondere jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methvl oder Ethv l substituiertes Ethan- l,2-dιyl, Propan- l ,3-dιyl oder Butan- 1 ,4-dιyl Steht R fürA represents optionally substituted, straight-chain or branched alkylene If R 6 and R 7 simultaneously represent amino, A preferably represents straight-chain or branched alkylene having 2 to 10 carbon atoms, in particular ethane which is optionally mono-, di- or trisubstituted by methylene or ethylene l l, 2-dιyl, propane l, 3-dιyl or butane 1, 4-dιyl R stands for
-COOR8 oder -CH(OR9)2, steht A bevorzugt für geradkettiges oder verzweigtes Alkylen mit 1 bis 8 Kohlenstoffatomen, insbesondere jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Methvlen.-COOR 8 or -CH (OR 9 ) 2 , A preferably represents straight-chain or branched alkylene having 1 to 8 carbon atoms, in particular in each case methylene substituted once, twice or three times by methyl or ethyl.
Ethan- l ,2-dιyl oder Propan-l ,3-dιylEthane-l, 2-dιyl or propane-l, 3-dιyl
Die bifunktionellen Alkylenverbindungen der Formel (V) sind bekannte Synthese¬ chemikalienThe bifunctional alkylene compounds of the formula (V) are known synthetic chemicals
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens c) als Ausgangsstoffe benotigten Ketone der Formel (II) sind bereits weiter oben, bei der Beschreibung des erfindungsgemaßen Verfahrens a), beschrieben
Die zur Durchführung des erfindungsgemäßen Verfahrens c) als Ausgangsstoffe benotigten Phosphorverbindungen sind durch die Formel (VI) allgemein definiert In dieser Formel (VI) hat R1 vorzugsweise bzw insbesondere diejenige Be¬ deutung, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemä- ßen Verbindungen der Formel (I) als bevorzugt bzw. als insbesondere bevorzugt für R1 angegeben wurde, steht für -P(R10)3 +X_oder -PO(ORn)2, wobei R10 für Aryl, bevorzugt Phenyl oder C1-C4-Alkyl, bevorzugt Butyl steht, und Rn für Alkyl, bevorzugt Methyl oder Ethyl steht, und X für Halogen, bevorzugt Chlor, Brom oder lod stehtThe ketones of the formula (II) required as starting materials for carrying out process c) according to the invention have already been described above in the description of process a) according to the invention Formula (VI) provides a general definition of the phosphorus compounds required as starting materials for carrying out process c) according to the invention. In this formula (VI), R 1 preferably or in particular has the meaning which is already in connection with the description of the compounds according to the invention of the formula (I) was given as preferred or as particularly preferred for R 1 , is -P (R 10 ) 3 + X _ or -PO (OR n ) 2 , where R 10 is aryl, preferably phenyl or C 1 -C 4 alkyl, preferably butyl, and R n is alkyl, preferably methyl or ethyl, and X is halogen, preferably chlorine, bromine or iodine
Die Phosphorverbindungen der Formel (VI) sind bekannte organische Synthese¬ chemikalienThe phosphorus compounds of the formula (VI) are known organic synthesis chemicals
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens d) als Ausgangsstoffe benotigten Thioamide sind durch die Formel (VII) allgemein definiert In dieser Formel (VII) haben Ar, E, G und Z vorzugsweise bzw insbesondere diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungs¬ gemäßen Verbindungen der Formel (I) als bevorzugt bzw als insbesondere be¬ vorzugt für Ar, E, G und Z angegeben wurdenFormula (VII) provides a general definition of the thioamides required as starting materials for carrying out process d) according to the invention. In this formula (VII) Ar, E, G and Z preferably or in particular have those meanings which have already been described in connection with the description of the invention ¬ compounds of the formula (I) have been indicated as preferred or as particularly preferred for Ar, E, G and Z.
Die Thioamide der Formel (VII) sind teilweise bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl z B EP-A 528 681 )Some of the thioamides of the formula (VII) are known and / or can be prepared by processes known per se (cf. for example EP-A 528 681)
Die zur Durchfuhrung des erfindungsgemaßen Verfahrens d ) weiterhin als Aus¬ gangsstoffe benotigten Halogenalkylverbindungen. bzw Acetylenverbindungen sind durch die Formeln (VIII), bzw (IX) allgemein definiert In Formel (VIII) steht R1" für Wasserstoff oder Alkyl. vorzugsweise für Wasserstoff oder Methyl Y1 steht für Cyano, Alkylcarbonyl. Arylcarbonyl, Formyl. Dialkoxyalkyl oder Al koxy carb ony l , vorzugswei se für Cy ano , Form y l , Di eth oxym ethv .The haloalkyl compounds also required as starting materials for carrying out process d) according to the invention. or acetylene compounds are generally defined by the formulas (VIII) or (IX) In formula (VIII) R 1 "is hydrogen or alkyl. Preferably hydrogen or methyl Y 1 is cyano, alkylcarbonyl. arylcarbonyl, formyl. dialkoxyalkyl or Al koxy carb ony l, preferably for cy ano, form yl, di eth oxym ethv.
Dimethoxvmethyl, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl oder Acetyl X1 steht für Halogen, vorzugsweise für Chlor oder Brom In Formel (IX) steht Y: für Alkoxycarbonyl, vorzugsweise Methoxycarbonyl oder Ethoxycarbonyl Y1 steht für Wasserstoff, Alkyl, Aryl, Alkylcarbonyl, Arylcarbonyl, oder Alkoxycarbonyl, vorzugsweise für Wasserstoff, Methyl , Ethyl, Phenyl, Acetyl , Benzoyl ,Dimethoxvmethyl, methoxycarbonyl, ethoxycarbonyl, benzoyl or acetyl, X 1 represents halogen, preferably chlorine or bromine In the formula (IX), Y: alkoxycarbonyl, preferably methoxycarbonyl or ethoxycarbonyl Y 1 is hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl, or Alkoxycarbonyl, preferably for hydrogen, methyl, ethyl, phenyl, acetyl, benzoyl,
Methoxvcarbonvl oder Ethoxvcarbonvl
Die Halogenalkylverbindungen der Formel (VIII) sind bekannte Synthesechemi¬ kalien.Methoxvcarbonvl or Ethoxvcarbonvl The haloalkyl compounds of the formula (VIII) are known synthetic chemicals.
Als Verdünnungsmittel zur Durchführung der erfindungsgemaßen Verfahren a), b), c) und d) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicyclische oder aromatische Kohlenwasser¬ stoffe, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methyl- cyclohexan, Benzol, Toluol, Xylol oder Decalin, halogenierte Kohlenwasserstoffe, wie beispielsweise Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetra¬ chlormethan, Dichlorethan oder Trichlorethan, Ether, wie Diethylether. Diisopropylether, Methyl-t-butylether, Methyl-t-Amylether, Dioxan, Tetrahydro- furan, 1,2- Dimethoxyethan, 1,2-Diethoxyethan oder Anisol; Ketone, wie Aceton, Butanon, Methyl-isobutylketon oder Cyclohexanon, Nitrile, wie Acetonitril, Propionitril, n- oder i-Butyronitril oder Benzonitril, Amide, wie N,N-Dimethyl- formamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsauretriamid; Ester wie Essigsäuremethylester oder Essigsau- reethylester, Sulfoxide, wie Dimethylsulfoxid; Sulfone, wie Sulfolan; Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, n-, i-, sek- oder tert-Butanol, Ethandiol, Propan-l,2-diol, Ethoxyethanol, Methoxy ethanol, Diethylenglykolmono- methylether, Diethylenglykolmonoethylether.Suitable diluents for carrying out processes a), b), c) and d) are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane , Dichloroethane or trichloroethane, ethers, such as diethyl ether. Diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone, nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxy ethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.
Die erfindungsgemäßen Verfahren a), b) und d) können auch in Gemischen der oben genannten Losungsmittel mit Wasser oder in reinem Wasser durchgeführt werdenThe processes a), b) and d) according to the invention can also be carried out in mixtures of the abovementioned solvents with water or in pure water
Die erfindungsgemaßen Verfahren a) und b) werden gegebenenfalls in Gegenwart einer Saure oder einer Base durchgeführtProcesses a) and b) according to the invention are optionally carried out in the presence of an acid or a base
Die erfindungsgemaßen Verfahren c) und d) werden gegebenenfalls in Gegenwart eines geeigneten Saureakzeptors durchgeführtProcesses c) and d) according to the invention are optionally carried out in the presence of a suitable acid acceptor
Als Sauren zur Durchfuhrung der erfindungsgemaßen Verfahren a) und b) kommen alle anorganischen und organischen, sowie auch alle polymeren Säuren infrage Hierzu gehören beispielsweise Chlorwasserstoff, Schwefelsaure, Phosphorsaure, Ameisensaure, Essigsaure, Trifluoressigsaure, Methansulfonsaure, Trifluormethan- sulfonsaure. Toluol sulfonsaure, saure Ionenaustauscher, saure Tonerden und saures Kieseigel
Als Base, bzw. Säureakzeptor zur Durchführung der erfindungsgemaßen Verfahren a), b), c) und d) kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie beispielsweise Natriumhydrid, Natriumamid, Natrium-methylat, Natrium-ethylat,Suitable acids for carrying out processes a) and b) according to the invention are all inorganic and organic, and also all polymeric acids. These include, for example, hydrogen chloride, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid. Toluene sulfonic acid, acidic ion exchangers, acidic clays and acidic silica gel Suitable bases or acid acceptors for carrying out processes a), b), c) and d) are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate,
Kalium-tert -butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, Kaliumacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbonat, Natriumhydrogencarbonat oder Ammo- niumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Triethylamin, Tributyl- amin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpiperidin,Potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylanil , N, N-dimethylbenzylamine, pyridine, N-methylpiperidine,
N-Methylmorpholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU)N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU)
Die Reaktionstemperaturen können bei der Durchfuhrung der erfindungsgemaßen Verfahren a) und b) in einem größeren Bereich variiert werden Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +200°C, vorzugsweise beiWhen carrying out processes a) and b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between -20 ° C. and + 200 ° C., preferably at
Temperaturen zwischen 20°C und 150°CTemperatures between 20 ° C and 150 ° C
Die Reaktionstemperaturen können auch bei der Durchfuhrung des erfindungs¬ gemaßen Verfahrens c) in einem größeren Bereich variiert werden Im allgemeinen arbeitet man bei Temperaturen zwischen -50°C und -H 00°C. vorzugsweise bei Temperaturen zwischen -20°C und +50°CThe reaction temperatures can also be varied within a substantial range when carrying out process c) according to the invention. In general, temperatures between -50 ° C. and -H 00 ° C. preferably at temperatures between -20 ° C and + 50 ° C
Die Reaktionstemperaturen können auch bei der Durchfuhrunü des erfindungs¬ gemaßen Verfahrens d) in einem größeren Bereich variiert w erden Im allgemeinen arbeitet man bei Temperaturen von 0°C bis 150°C, vorzugsweise bei Temperaturen
The reaction temperatures can also be varied over a wide range in carrying out process d) according to the invention. In general, temperatures from 0 ° C. to 150 ° C., preferably at temperatures
Zur Durchfuhrung des erfindungsgemaßen Verfahrens a) zur Herstellung der Ver¬ bindungen der Formel (I) setzt man pro Mol des Ketons der Formel (II) im all¬ gemeinen 1 bis 15 Mol. vorzugsweise 1 bis 8 Mol Amin ser Formel (III) einTo carry out process a) according to the invention for the preparation of the compounds of the formula (I), 1 to 15 mol, preferably 1 to 8 mol, of amine formula (III) are generally employed per mole of the ketone of the formula (II)
Zur Durchfuhrung des erfindungsgemaßen Verfahrens b) zur Herstellung der Ver¬ bindungen der Formel (I) setzt man pro Mol des Nitπls der Formel (IV) im all- gemeinen 0,5 bis 15 Mol, vorzugsweise 0,5 bis 2 Mol des Diamins der Formel (V) ein
Zur Durchfuhrung des erfindungsgemaßen Verfahrens c) zur Herstellung der Ver¬ bindungen der Formel (I) setzt man pro Mol Phosphorverbindungen der Formel (VI) im allgemeinen 0,5 bis 15 Mol, vorzugsweise 0,8 bis 5 Mol Ketoverbindung der Formel (II) einIn order to carry out process b) according to the invention for the preparation of the compounds of the formula (I), 0.5 to 15 mol, preferably 0.5 to 2 mol, of the diamine are generally employed per mol of the nitrogen of the formula (IV) Formula (V) To carry out process c) according to the invention for the preparation of the compounds of the formula (I), generally 0.5 to 15 mol, preferably 0.8 to 5 mol, of keto compound of the formula (II) are used per mole of phosphorus compound of the formula (VI) on
Zur Durchfuhrung des erfindungsgemaßen Verfahrens d) zur Herstellung der Ver¬ bindungen der Formel (I) setzt man pro Mol des Thioamids der Formel (VII) im allgemeinen 0,5 bis 15 Mol, vorzugsweise 0,8 bis 5 Mol Halogenalkvlverbindung der Formel (VIII) oder Acetylenverbindung der Formel (IX) einTo carry out process d) according to the invention for the preparation of the compounds of the formula (I), 0.5 to 15 mol, preferably 0.8 to 5 mol, of haloalkylene compound of the formula (VIII.) Are generally employed per mol of the thioamide of the formula (VII) ) or acetylene compound of the formula (IX)
Das erfindungsgemaße Verfahren a), b), c) und d) werden im allgemeinen unter Normaldruck durchgeführt Es ist jedoch auch möglich, unter erhöhtem oder ver¬ mindertem Druck - im allgemeinen zwischen 0,1 bar und 10 bar - zu arbeitenProcesses a), b), c) and d) according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar
Die Reaktionsdurchfuhrung, Aufarbeitung und Isolierung der Reaküonsprodukte der erfindungsgemaßen Verfahren erfolgt nach bekannten Methoden (vgl auch die Herstellungsbeispiele)The reaction, processing and isolation of the reaction products of the processes according to the invention is carried out by known methods (cf. also the preparation examples).
Die erfindungsgemaßen Wirkstoffe weisen eine starke mikrobizide Wirkung auf und werden zur Bekämpfung von unerwünschten Mikroorganismen praktisch eingesetzt Die Wirkstoffe sind für den Gebrauch als Pflanzenschutzmittel insbesondere als Fungizide geeignetThe active compounds according to the invention have a strong microbicidal action and are used practically to combat unwanted microorganisms. The active compounds are particularly suitable for use as crop protection agents as fungicides
Fungizide Mittel im Pflanzenschutz werden eingesetzt zur Bekämpfung von Plas- modiophoromvcetes, Oomvcetes Chytπdiomvcetes Zv gomvcetes AscomvcetesFungicidal agents in crop protection are used to combat plasmodiophoromvcetes, oomvcetes chytπdiomvcetes, and gomvcetes ascomvcetes
Basidiomycetes, DeuteromvcetesBasidiomycetes, Deuteromvcetes
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzhchen Krank¬ heiten die unter die oben aufgezahlten Oberbegriffe fallen, genanntSome pathogens of fungal diseases which fall under the generic terms listed above may be mentioned as examples, but not by way of limitation
Pvthium-Arten, wie beispielsweise Pvthium ultimum Phvtophthora-Arten, wie beispielsweise Phytophthora infestans,Pvthium species, such as, for example, Pvthium ultimum Phvtophthora species, such as, for example, Phytophthora infestans,
Pseudoperonospora- Arten, wie beispielsweise Pseudoperonospora humuli oderPseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubense,Pseudoperonospora cubense,
Plasmopara-Arten, wie beispielsweise Plasmopara viticolaPlasmopara species, such as, for example, Plasmopara viticola
Peronospora-Arten wie beispielsweise Peronospora pisi oder Peronospora brassicae
Erysiphe-Arten, wie beispielsweise Erysiphe graminis,Peronospora species such as Peronospora pisi or Peronospora brassicae Erysiphe species, such as, for example, Erysiphe graminis,
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea;Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha,Podosphaera species, such as, for example, Podosphaera leucotricha,
Venturia- Arten, wie beispielsweise Venturia inaequalis, Pyrenophora-Arten, wie beispielweise Pyrenophora teres oder Pyrenophora graminea (Konidienform: Drechslera, Synonym Helminthosporium),Venturia species, such as, for example, Venturia inaequalis, Pyrenophora species, such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym Helminthosporium),
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativus (KonidienformCochliobolus species, such as Cochliobolus sativus (conidia form
Drechslera, Synonym: Helminthosporium),Drechslera, synonym: Helminthosporium),
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus, Puccinia- Arten, wie beispielsweise Puccinia recondita,Uromyces species, such as, for example, Uromyces appendiculatus, Puccinia species, such as, for example, Puccinia recondita,
Tilletia- Arten, wie beispielsweise Tilletia caries,Tilletia species, such as, for example, Tilletia caries,
Ustilago-Arten, wie beispielsweise Ustilago nuda oder Ustilago avenae,Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae,
Pellicularia-Arten, wie beispielsweise Pellicularia sasakii,Pellicularia species, such as, for example, Pellicularia sasakii,
Pyricularia- Arten, wie beispielsweise Pyricularia oryzae, Fusarium-Arten, wie beispielsweise Fusarium culmorum,Pyricularia species, such as, for example, Pyricularia oryzae, Fusarium species, such as, for example, Fusarium culmorum,
Botrytis-Arten, wie beispielsweise Botrytis cinerea,Botrytis species, such as, for example, Botrytis cinerea,
Septoria- Arten, wie beispielsweise Septoria nodorum,Septoria species, such as, for example, Septoria nodorum,
Leptosphaeria-Arten, wie beispielsweise Leptosphaeria nodorum,Leptosphaeria species, such as, for example, Leptosphaeria nodorum,
Cercospora-Arten, wie beispielsweise Cercospora canescens; Alternaria-Arten, wie beispielsweise Alternaria brassicae,Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae,
Pseudocercosporella-Arten, wie beispielsweise Pseudocercosporella herpotπchoi- desPseudocercosporella species, such as, for example, Pseudocercosporella herpotπchoides
Die gute Pflanzenvertraglichkeit der Wirkstoffe in den zur Bekämpfung von Pflan¬ zenkrankheiten notwendigen Konzentrationen, erlaubt eine Behandlung von obeπr- dischen Pflanzenteilen, sowie auch eine Behandlung von Pflanz- und Saatgut und des BodensThe fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of parts of the plant which are at the root, and also treatment of planting material and seeds and of the soil
Dabei werden die erfindungsgemaßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Getreidekrankheiten, wie beispielsweise gegen Erysiphe-Arten. oder von Krankheiten im Wein-, Obst- und Gemüseanbau, wie beispielsweise gegen Plasmopara-Arten, oder von Reiskrankheiten, wie beispielsweise gegenThe active compounds according to the invention are particularly successful in combating cereal diseases, for example against Erysiphe species. or of diseases in wine, fruit and vegetable growing, such as for example against Plasmopara species, or of rice diseases, such as against
Pyricularia- Arten eingesetzt Mit gutem Erfolg werden mit den erfindungsgemaßen Werkstoffen auch weitere Pflanzenkrankheiten, wie beispielsweise Podospherea- Arten und Venturia- Arten bekämpft
Die Wirkstoffe werden in Abhängigkeit von ihren jeweiligen physikalischen und/oder chemischen Eigenschaften gegebenenfalls in übliche Formulierungen übergeführt, wie z. B. Lösungen, Emulsionen, Suspensionen, Pulver, Schaume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-Kalt- und -Warmnebel-FormulierungenPyricularia species used Other plant diseases, such as, for example, Podospherea species and Venturia species, are also successfully combated with the materials according to the invention Depending on their respective physical and / or chemical properties, the active compounds are converted into conventional formulations, such as, for. B. solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm fog formulations
Diese Formulierungen werden in bekannter Weise hergestellt, z.B durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln Im Falle der Benutzung von Wasser als Streckmittel können z.B auch organische Losungsmittel als Hilfslosungsmittel verwendet werden Als flussige Losungsmittel kommen im wesentlichen infrage Aromaten, wie Xylol, Toluol, Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene, oder Methylenchlorid, aliphatsche Kohlenwasserstoffe, wieThese formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Aromatic compounds, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene, or methylene chloride, aliphatic hydrocarbons, are essentially suitable as liquid solvents. how
Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Losungsmittel , wie Dimethylformamid oder Dimethylsulfoxid, sowie Wasser, mit verflüssigten gasformigen Streckmitteln oder Tragerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasformig sind, z B Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan. Propan, Stickstoff und Kohlendioxid, als feste Tragerstoffe kommen infrage z B natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quartz, Attapulgit, Mont- morillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperseCyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water, with liquefied gaseous extenders or carriers are meant as liquids which are used for are gaseous at normal temperature and pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane. Propane, nitrogen and carbon dioxide, as solid carrier materials come into consideration, for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse
Kieselsaure, Aluminiumoxid und Silikate, als feste Tragerstoffe für Granulate kommen infrage z B gebrochene und fraktionierte naturliche Gesteine wie Calcit. Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sagemehl, Kokosnußschalen, Maiskolben und Tabakstengel, als Emulgier- und/oder schaum¬ erzeugende Mittel kommen infrage z B nicht ionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsaureester, Polyoxyethylen-Fettalkohol-Ether, z B Alkylarylpolyglykolether, Alkyl sulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate, als Dispergiermittel kommen infrage. z B. Ligninsulfitablaugen und Methvlcellulose
Es werden in den Formulierungen gegebenenfalls Haftmittel wie Carboxymethyl- cellulose, natürliche und synthetische, pulverige, körnige oder latexförmige Polymere verwendet, wie z. B. Gummiarabicum, Polyvinylalkohol, Polyvinyl- acetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere mögliche Additive sind mineralische und vegetabile Öle.Silicic acid, aluminum oxide and silicates, for example broken and fractionated natural rocks such as calcite are suitable as solid carriers for granules. Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Examples of suitable emulsifiers and / or foam-producing agents are nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, are suitable as dispersants. e.g. lignin sulfite leaching and methyl cellulose If appropriate, adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers are used in the formulations, such as, for. B. gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other possible additives are mineral and vegetable oils.
Gegebenenfalls werden Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink zugesetztIf necessary, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are added
Die Formulierungen enthalten im allgemeinenzwischen 0, 1 und 95 Gewichtspro¬ zent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
Die erfindungsgemaßen Wirkstoffe werden als solche oder in ihren Formulie¬ rungen auch in Mischung mit bekannten Fungiziden, Bakteriziden, Akariziden, Nematiziden oder Insektiziden verwendet, um so z.B das Wirkungsspektrum zu verbreitern oder Resistenzentwicklungen vorzubeugen.The active compounds according to the invention are used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of action or to prevent the development of resistance.
In vielen Fällen werden dabei synergistische Wirkungen beobachtet.In many cases, synergistic effects are observed.
Für die Mischungen kommen beispielsweise infrageFor the mixtures, for example
Fungizide:Fungicides:
2-Aminobutan, 2-Anilino-4-methyl-6-cyclopropvl-pyrιmidιn. 2'.6'-Dibromo-2- n.ethvl-4'-trifluoromethoxv -4'-trifluoro-methvl- l X-thιzole-5-carboxanilιd, 2.0-2-aminobutane, 2-anilino-4-methyl-6-cyclopropvl-pyrιmidιn. 2'.6'-dibromo-2-n.ethvl-4'-trifluoromethoxv -4'-trifluoro-methvl- l X-thιzole-5-carboxanilιd, 2.0-
Dιchloro-N-(4-trifluoromethylbenzyl )benzamιd. (E )-2-Methoxyimιno-N-methyl-2-Dιchloro-N- (4-trifluoromethylbenzyl) benzamιd. (E) -2-methoxyimino-N-methyl-2-
(2-phenoxvphenyl ) acetamid, 8-Hydroxyquιnolιnsulfat; Methyl-(E)-2- ! 2-[6-( 2- cy an o-phenoxy )pyri midi n-4-yloxy] phenyl } -3 -m ethoxy acrylat; Methyl -(E )- methoximino [alpha-(o-tolyloxy)-o-tolyl] acetat, 2-Phenylphenol (OPP ).(2-phenoxvphenyl) acetamide, 8-hydroxyquinol sulfate; Methyl- (E) -2-! 2- [6- (2-cy an o-phenoxy) pyrimidine-4-yloxy] phenyl} -3 -m ethoxy acrylate; Methyl - (E) - methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP).
Aldimorph, Ampropylfos, Anilazin, Azaconazol,Aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S.Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S.
Bromuconazole, Bupirimate, Buthiobate,Bromuconazole, Bupirimate, Buthiobate,
Calciumpolvsulfid. Captafol, Captan, Carbendazim. Carboxin, ChinomethionatCalcium polysulfide. Captafol, Captan, Carbendazim. Carboxin, quinomethionate
(Quinomethionat), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Cufraneb.
Cymoxanil, Cyproconazole, Cyprofuram,(Quinomethionate), Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinate, Cufraneb. Cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethiπmol, Dimethomorph, Diniconazol, Dinocap, Diphe- nylamin, Dipyrithion, Ditahmfos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethiπmol, Etridiazol,Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethiπmol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditahmfos, dithianon, dodin, drazazololidol, ethoxazole tri
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropi-morph, Fenünacetate, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolaml, Flutriafol, Folpet, Fosetyl-Aluminium, Fthahde, Fubeπdazol, Furalaxyl, Furmecyclox,Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropi-morph, Fenünacetate, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolamyl, Folut, Futolaml, Folut, Futolaml, Futolaml, Futolaml, Folut, Futolaml, Folut, Futolaml, Folut, Futolaml, Folut, Futolaml, Futolaml, Futolaml, Folut Furalaxyl, furmecyclox,
Guazatine,Guazatine,
Hexachlorobenzol, Hexaconazol, Hymexazol,Hexachlorobenzene, hexaconazole, hymexazole,
Imazahl, Imibenconazol, Iminoctadin, Iprobenfos (IBP), Iprodion, Isoprothiolan. Kasugamycin, Kupfer-Zubereitungen, wie Kupferhydroxid, Kupfernaphthenat Kupferoxychloπd, Kupfersulfat, Kupferoxid, Oxin-Kupfer and Bordeaux-Imazahl, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan. Kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux
Mischung,Mixture,
Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Me hfuroxam, Metiram, Metsulfovax, Myclobutanil, Nickel dimethyldithiocarbamat, Nitrothal-isopropyl, Nuaπmol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Me hfuroxam, Metiram, Metsulfovax, Myclobutanil, Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuaπmol, Ofurace, Oxadoxoxylxylxylxylxylxylxixyl
Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaπαn Piperalm Polvoxin Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole Propineb Pyrazophos, Pvπfenox Pvπmethanil, Pyroquilon Quintozen (PCNB) Schwefel und Schwefel-Zubereitungen,Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaπαn Piperalm Polvoxin Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole Propineb Pyrazophos, Pvπfenox Pvπmethanil, Pyroquilon Quintozen (PCNB) preparations, sulfur and sulfur
Tebuconazol, Tecloftalam, Tecnazen, Tetraconazol, Thiabendazol Thicvofen Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolv fluanid, Tπadi efon, Tπadi- menol, Tπazoxid Tπchlamid Tπcyclazol, Tπdemorph, Tπflumizol, Tπfoπn Tπüconazol, Vahdamycin A, Vinclozolm,Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicvofen, thiophanate-methyl, thiram, tolclophos-methyl, tolv fluanid, tπadilamon, tπdemolum, tπflumol, tπflumcinol
Zineb. ZiramZineb. Ziram
Bakterizide:Bactericides:
Bronopol , Di chlorophen, Nitrapvπn, Ni ckel Dim ethvl dithi ocarbamat Kasugamycin, Octhihnon, Furancarbonsaure, Oxytetracvchn, Probenazol Streptomvcin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen
Insektizide / Akarizide / Nematizide:Bronopol, Di chlorophene, Nitrapvπn, Nickel dim Ethvl dithi ocarbamat Kasugamycin, Octhihnon, Furancarbonsaure, Oxytetracvchn, Probenazol Streptomvcin, Tecloftalam, copper sulfate and other copper preparations Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha- methπn, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M,Abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alpha-methπn, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M,
Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin,Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin,
Bifenthπn, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin,Bifenthπn, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin,
Butocarboxin, Butylpyπdaben,Butocarboxin, Butylpyπdaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyπfos, Chlorpyπfos M, Cis-Resmethπn,419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyπfos, Chlorpyπfos M, Cis-Resmethπn,
Clocythπn, Clofentezin, Cyanophos, Cycloprothπn, Cyfluthπn, Cvhalothπn,Clocythπn, Clofentezin, Cyanophos, Cycloprothπn, Cyfluthπn, Cvhalothπn,
Cyhexatin, Cypermethπn, Cyromazin,Cyhexatin, cypermethπn, cyromazine,
Deltamethπn, Demeton M, Demeton S, Demeton-S-methyl, DiafenthiuronDeltamethπn, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron
Diazinon, Dichlofenthion, Dichlorvos, Dichphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,Diazinon, dichlofenthion, dichlorvos, dichphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathione, disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethopro- phos, Etofenprox, Etrimphos,Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etofenprox, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb,Fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Flufenprox, Fluv- ahnate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Flufenprox, Fluv- ahnate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
HCH, Heptenophos, Hexaflumuron, Hexvthiazox. lmidaclopπd, Iprobenfos, Isazophos, Isofenphos Isoprocarb lsoxathion, IvemectinHCH, heptenophos, hexaflumuron, hexvthiazox. Imidaclopπd, Iprobefos, Isazophos, Isofenphos Isoprocarb lsoxathion, Ivemectin
Lamda-cyhalothnn, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd Methacπfos,Lamda-cyhalothnn, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd Methacπfos,
Methamidophos, Methidathion, Methiocarb, Methomvl, Metolcarb, Milbemecün,Methamidophos, Methidathion, Methiocarb, Methomvl, Metolcarb, Milbemecün,
Monocrotophos, Moxidecün,Monocrotophos, Moxidecün,
Naled, NC 184, NI 25, NitenpyramNaled, NC 184, NI 25, Nitenpyram
Omethoat, Oxamyl, Oxydemethon M, Oxvdeprofos, Parathion A, Parathion M. Permethnn, Phenthoat Phorat, Phosalon, Phosmet,Omethoat, Oxamyl, Oxydemethon M, Oxvdeprofos, Parathion A, Parathion M. Permethnn, Phenthoat Phorat, Phosalon, Phosmet,
Phosphamdon, Phoxim, Piπmicarb, Piπmiphos M, .Pπmiphos \. Profenofos,Phosphamdon, Phoxim, Piπmicarb, Piπmiphos M, .Pπmiphos \. Profenofos,
Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos Prothoat,Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos Prothoat,
Pymetrozin, Pyrachlophos, Pyracl ofos, Pyraclophos. Pvradaphenthi onPymetrozine, Pyrachlophos, Pyracl ofos, Pyraclophos. Pvradaphenthi on
Pyresmethπn, Pyrethrum, Pyπdaben, Pvπmidifen, Pyπproxifen. Quinalphos,Pyresmethπn, Pyrethrum, Pyπdaben, Pvπmidifen, Pyπproxifen. Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio- methon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb,Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhrononium, Trionomoshrononium, Triomenethriazonium, Tri
Vamidothion, XMC, Xylylcarb, YI 5301 / 5302, ZetamethrinVamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin
Gegebenenfalls werden die erfindungsgemaßen Wirkstoffe auch mit anderen bekannten Wirkstoffen, wie Herbiziden oder auch mit Düngemitteln und Wachstumsregulatoren gemischtIf appropriate, the active compounds according to the invention are also mixed with other known active compounds, such as herbicides or else with fertilizers and growth regulators
Die Wirkstoffe werden als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Losungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Staubemittel und Granulate angewendet Die Anwendung geschieht in üblicher Weise, z.B durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstauben, Verschaumen, Bestreichen usw Gegebenenfalls werden die Wirkstoffe nach dem Ultra-Low- Volume- Verfahren ausgebracht oder die Wirkstoffzubereitung oder der Wirkstoff selbst wird in den Boden injiziert Gegebenenfalls wird auch das Saatgut der Pflanzen behandeltThe active ingredients are used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules. They are used in the customary manner, for example by pouring, spraying, spraying, scattering, Dusting, foaming, brushing, etc. If necessary, the active ingredients are applied using the ultra-low-volume method or the active ingredient preparation or the active ingredient itself is injected into the soil. If appropriate, the seeds of the plants are also treated
Bei der Behandlung von Pflanzenteilen können die Wirkstoffkonzentrationen in den Anwendungsformen in einem größeren Bereich variiert werden Sie liegen im allgemeinen zwischen 1 und 0,0001 Gew -%, vorzugsweise zwischen 0,5 undIn the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range and are generally between 1 and 0.0001% by weight, preferably between 0.5 and
0,001 Gew -°/0 0.001% w / o
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoff mengen von 0,001 bis 50 g je Kilogramm Saatgut, vorzugsweise 0,01 bis 10 g benotigtIn the case of seed treatment, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required
Bei der Behandlung des Bodens sind Wirkstoffkonzentrationen von 0,00001 bis 0, 1 Gew -%, vorzugsweise von 0,0001 bis 0,02 Gew -% am Wirkungsort erforderlichWhen treating the soil, active substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action
Die erfindungsgemaßen Wirkstoffe weisen eine starke mikrobizide Wirkung auf und werden zur Bekämpfung von unerwünschten Mikroorganismen praktisch eingesetzt Die Wirkstoffe sind für den Gebrauch als Pflanzenschutzmittel. insbesondere als Fungizide geeignet
Fungizide Mittel im Pflanzenschutz werden eingesetzt zur Bekämpfung von Plas- modiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.The active compounds according to the invention have a strong microbicidal action and are used in practice to combat unwanted microorganisms. The active compounds are for use as crop protection agents. particularly suitable as fungicides Fungicidal agents in crop protection are used to combat plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen Krank- heiten, die unter die oben aufgezahlten Oberbegriffe fallen, genanntSome pathogens of fungal diseases which fall under the generic names listed above may be mentioned as examples, but not by way of limitation
Pythium-Arten, wie beispielsweise Pythium ultimum,Pythium species, such as Pythium ultimum,
Phytophthora- Arten, wie beispielsweise Phytophthora infestans,Phytophthora species, such as, for example, Phytophthora infestans,
Pseudoperonospora-Arten, wie beispielsweise Pseudoperonospora humuli oderPseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubense, Plasmopara-Arten, wie beispielsweise Plasmopara viücola,Pseudoperonospora cubense, Plasmopara species, such as, for example, Plasmopara viücola,
Peronospora-Arten, wie beispielsweise Peronospora pisi oder Peronospora brassicae,Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae,
Erysiphe-Arten, wie beispielsweise Erysiphe graminis,Erysiphe species, such as, for example, Erysiphe graminis,
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea, Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha,Sphaerotheca species, such as, for example, Sphaerotheca fuliginea, Podosphaera species, such as, for example, Podosphaera leucotricha,
Venturia-Arten, wie beispielsweise Venturia inaequalis,Venturia species, such as, for example, Venturia inaequalis,
Pyrenophora-Arten, wie beispielweise Pyrenophora teres oder Pyrenophora graminea (Konidienform Drechslera, Synonym Helminthosporium),Pyrenophora species, such as, for example, Pyrenophora teres or Pyrenophora graminea (conidia form Drechslera, synonym Helminthosporium),
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativus (Konidienform Drechslera, Synonym Helminthosporium),Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form Drechslera, synonym Helminthosporium),
Uromvces-Arten, wie beispielsweise Uromyces appendiculatus,Uromvces species, such as, for example, Uromyces appendiculatus,
Puccinia-Arten. wie beispielsweise Puccinia recondita.Puccinia species. such as Puccinia recondita.
Tilletia- Arten, wie beispielsweise Tilletia caπes,Tilletia species, such as, for example, Tilletia caπes,
Ustilago-Arten, wie beispielsweise Ustilago nuda oder Ustilago avenae, Pelliculaπa-Arten, wie beispielsweise Pelhculaπa sasakii,Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae, Pelliculaπa species, such as, for example, Pelhculaπa sasakii,
Pvπculaπa-Arten. wie beispielsweise Pyricularia oryzae,Pvπculaπa species. such as Pyricularia oryzae,
Fusaπum-Arten. wie beispielsweise Fusaπum culmorum.Fusaπum species. such as Fusaπum culmorum.
Botrytis-Arten, wie beispielsweise Botrvtis cinerea.Botrytis species, such as, for example, Botrvtis cinerea.
Septoπa-Arten. wie beispielsweise Septoria nodorum, Leptosphaeπa-Arten. wie beispielsweise Leptosphaeπa nodorum,Septoπa species. such as Septoria nodorum, Leptosphaeπa species. such as Leptosphaeπa nodorum,
Cercospora-Arten, wie beispielsweise Cercospora canescens,Cercospora species, such as, for example, Cercospora canescens,
Die gute Pflanzenvertraghchkeit der Wirkstoffe in den zur Bekämpfung von Pflan¬ zenkrankheiten notwendigen Konzentrationen, erlaubt eine Behandlung von oberir-
dischen Pflanzenteilen, sowie auch eine Behandlung von Pflanz- und Saatgut und des BodensThe good plant tolerance of the active ingredients in the concentrations necessary to combat plant diseases allows treatment of top plant parts, as well as a treatment of plant and seed and the soil
Dabei werden die erfindungsgemaßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Krankheiten im Wein-, Obst- und Gemüseanbau, wie beispiels- weise gegen Plasmopara- und Podosphaera-Arten eingesetztThe active compounds according to the invention are used with particularly good success for combating diseases in wine, fruit and vegetable cultivation, such as, for example, against Plasmopara and Podosphaera species
Die erfindungsgemaßen Wirkstoffe werden auch mit gutem Erfolg zur Be¬ kämpfung von Getreidekrankheiten, wie beispielsweise gegen Septoria-, Pyricularia-, Pyrenophora- sowie Cochliobolus-Arten eingesetzt Außerdem zeigen die erfindungsgemaßen Wirkstoffe eine besonders gute in vitro WirkungThe active compounds according to the invention are also used with good success for combating cereal diseases, for example against Septoria, Pyricularia, Pyrenophora and Cochliobolus species. In addition, the active compounds according to the invention have a particularly good in vitro effect
Die Wirkstoffe werden in Abhängigkeit von ihren jeweiligen physikalischen und/oder chemischen Eigenschaften gegebenenfalls in übliche Formulierungen übergeführt, wie z B Losungen, Emulsionen, Suspensionen, Pulver, Schaume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hullmassen für Saatgut, sowie ULV-Kalt- und -Warmnebel-FormulierungenDepending on their respective physical and / or chemical properties, the active ingredients may be converted into customary formulations, such as, for example, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also ULV cold and warm fog formulations
Diese Formulierungen werden in bekannter Weise hergestellt, z B durchThese formulations are prepared in a known manner, for example by
Vermischen der Wirkstoffe mit Streckmitteln, also flussigen Losungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Tragerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln Im Falle der Benutzung von Wasser als Streckmittel können z B auch organische Lösungsmittel alsMixing the active ingredients with extenders, i.e. liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents also organic solvents as
Hilfslosungsmittel verwendet werden Als flussige Lösungsmittel kommen im wesentlichen infrage Aromaten wie Xv lol Toluol Alkvlnaphthahne chlorierte Aromaten oder chlorierte ahphatische Kohlenwasserstoffe wie Chlorbenzole Chl orethv l ene oder Methv lenchl oπ d al i phatsche Kohl enw asserstoff e w ie C v clohexan oder Paraffine, z B Erdollraktionen Alkohole w ie Butanol oderAuxiliary solvents are used as liquid solvents are essentially aromatics such as xvol toluene alkanol naphthane chlorinated aromatics or chlorinated ahphatic hydrocarbons such as chlorobenzenes, chlorethethane or methylene chloride or methane carbon dioxide and cvclohexane or paraffins, e.g. petroleum fractions Alcohols such as butanol or
Glv kol sowie deren Ether und Ester ketone wie Aceton Methvlethv lketon Methvlisobutylketon oder Cv clohexanon, stark polare Losungsmittel , wie Dimethylformamid oder Dimethvlsulfoxid. sowie Wasser, mit verflüssigten gasformigen Streckmitteln oder Tragerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasformig sind, z BGlv kol and their ethers and ester ketones such as acetone, methylene chloride, methylene isobutyl ketone or Cv clohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide. as well as water, with liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and pressure, e.g.
Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan Propan Stickstoff und Kohlendioxid, als feste Tragerstoffe kommen infrage z B natürliche Gesteinsmehle wie Kaoline, Tonerden Talkum, Kreide, Quartz Attapulgit Mont-
morillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl,Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide, can be used as solid carrier materials, e.g. natural rock powder such as kaolins, alumina talc, chalk, quartz attapulgite mont- Morillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules organic material such as sawdust,
Kokosnußschalen, Maiskolben und Tabakstengel, als Emulgier- und/oder schaum¬ erzeugende Mittel kommen infrage z.B nicht ionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsaureester, Polyoxyethylen-Fettalkohol-Ether, z.B Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate, als Dispergiermittel kommen infrage z.B Ligninsulfitablaugen und MethylcelluloseCoconut shells, corn cobs and tobacco stalks are suitable as emulsifying and / or foaming agents, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein dispersants in question, for example, lignin sulfite liquor and methyl cellulose
Es werden in den Formulierungen gegebenenfalls Haftmittel wie Carboxymethyl- cellulose, naturliche und synthetische, pulverige, kornige oder latexförmige Polymere verwendet, wie z B Gummiarabicum, Polyvinylalkohol, Polyvinyl- acetat, sowie naturliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide Weitere mögliche Additive sind mineralische und vegetabile Ole.Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as, for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, are further possible additives in the formulations mineral and vegetable oils.
Gegebenenfalls werden Farbstoffe wie anorganische Pigmente, z B Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennahrstoffe wie Salze von Eisen, ManganOptionally, dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese
Bor, Kupfer, Kobalt, Molybdän und Zink zugesetztBoron, copper, cobalt, molybdenum and zinc added
Die Formulierungen enthalten im allgemeinenzvvischen 0, 1 und 95 Gewichts¬ prozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %The formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%
Di e erfi ndungsgemaßen Wi rkstoffe werden al s sol che oder i n i hren Formulierungen auch in Mischung mit bekannten Fungiziden, Bakteriziden,The active substances according to the invention, as such or in their formulations, are also mixed with known fungicides, bactericides,
Akarizi den, Nematiziden oder Insektiziden verwendet, um so z B das Wirkungsspektrum zu verbreitern oder Resistenzen .Wicklungen vorzubeugenAkarizi, nematicides or insecticides are used to broaden the spectrum of activity or to prevent resistance
In vielen Fallen werden dabei synergistische Wirkungen beobachtetIn many cases, synergistic effects are observed
Für die Mischungen kommen beispielsweise infrage
Fungizide:For the mixtures, for example Fungicides:
2-Amιnobutan, 2-Anιlιno-4-methyl-6-cyclopropyl-pyπmιdιn, 2',6'-Dιbromo-2- methyl-4'-tπfluoromethoxy-4'-tπfluoro-methyl-l ,3-thιzole-5-carboxanιlιd, 2,6-2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-pyπmιdιn, 2 ', 6'-dιbromo-2-methyl-4'-tπfluoromethoxy-4'-tπfluoromethyl-l, 3-thιzole-5- carboxanιlιd, 2.6-
Dιchloro-N-(4-tπfluoromethylbenzyl)benzamιd, (E)-2-Methoxyιmιno-N-methyl-2- (2-phenoxyphenyl) acetamid, 8-Hydroxyquιnolιnsulfat, Methyl-(E)-2-{2-[6-(2- cyano-phenoxy)pyπmιdιn-4-yloxy]phenyl } -3 -methoxy acrylat, Methyl -(E)- methoximino [alpha-(o-tolyloxy)-o-tolyl] acetat, 2-Phenylphenol (OPP),Dιchloro-N- (4-tπfluoromethylbenzyl) benzamιd, (E) -2-methoxyιmιno-N-methyl-2- (2-phenoxyphenyl) acetamide, 8-Hydroxyquιnolιnsulfat, methyl- (E) -2- {2- [6- (2-cyano-phenoxy) pyπmιdιn-4-yloxy] phenyl} -3-methoxy acrylate, methyl - (E) - methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate, 2-phenylphenol (OPP),
Aldimorph, Ampropylfos, Anilazin, Azaconazol,Aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S Bromuconazole, Bupiπmate, Buthiobate,Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S Bromuconazole, Bupiπmate, Buthiobate,
Calciumpolysulfid, Captafol, Captan, Carbendazim, Carboxin, ChinomethionatCalcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate
(Quinomethionat), Chloroneb, Chloropicπn, Chlorothalonil, Chlozohnat, Cufraneb,(Quinomethionate), Chloroneb, Chloropicπn, Chlorothalonil, Chlozohnat, Cufraneb,
Cymoxanil, Cyproconazole, Cyprofuram,Cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethinmol, Dimethomorph, Diniconazol, Dinocap, Diphe- nylamin, Dipyπthion, Ditahmfos, Dithianon, Dodin, Drazoxolon,Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethinmol, dimethomorph, diniconazole, dinocap, diphenylamine, dipythion, ditahmfos, dithianon, dodin, drazoxolon
Edifenphos, Epoxyconazole, Ethiπmol, Etπdiazol,Edifenphos, Epoxyconazole, Ethiπmol, Etπdiazol,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin,Fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin,
Fenpropi-morph, Fenünacetate, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolaml,Fenpropi-morph, Fenünacetate, Fenünhydroxyd, Ferbam, Feπmzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolaml,
Flutπafol, Folpet, Fosetyl-Aluminium, Fthalide, Fubeπdazol , Furalaxyl,Flutπafol, Folpet, Fosetyl-Aluminum, Fthalide, Fubeπdazol, Furalaxyl,
Furmecvclox,Furmecvclox,
GuazatineGuazatine
Hexachlorobenzol, Hexaconazol Hymexazol, Imazahl, Imibenconazol, Iminoctadin, Iprobenfos (EBP), Iprodion, Isoprothiolan,Hexachlorobenzene, hexaconazole, hymexazole, ima number, imibenconazole, iminoctadine, iprobefos (EBP), iprodione, isoprothiolan,
Kasugamycin Kupfer-Zubereitungen, wie Kupferhydroxid KupfernaphthenatKasugamycin copper preparations, such as copper hydroxide, copper naphthenate
Kupferoxychloπd Kupfersulfat, Kupferoxid, Oxin-Kupfer and Bordeaux- Mischung,Copper oxychloride copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol, Methasulfocarb Methfuroxam, Meüram, Metsulfovax, Myclobutanil,Mancopper, Mancozeb, Maneb, Mepanipyπm, Mepronil, Metalaxyl, Metconazol, Methasulfocarb Methfuroxam, Meüram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamat, Nitrothal-isopropyl, NuaπmolNickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuaπmol
Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoat, Penconazol Pencvcuron, Phosdiphen, Pimaπcin Piperahn, PolyoxinPefurazoat, Penconazol Pencvcuron, Phosdiphen, Pimaπcin Piperahn, Polyoxin
Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb Pvrazophos, Pyπfenox, Pyπmethanil, Pvroquilon,Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazole, Propineb Pvrazophos, Pyπfenox, Pyπmethanil, Pvroquilon,
Quintozen (PCNB),
Schwefel und Schwefel-Zubereitungen,Quintozen (PCNB), Sulfur and sulfur preparations,
Tebuconazol, Tecloftalam, Tecnazen, Tetraconazol, Thiabendazol, Thicyofen,Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadi- menol, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin.Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin.
Triticonazol,Triticonazole,
Validamycin A, Vinclozolin,Validamycin A, vinclozolin,
Zineb, ZiramZineb, ziram
Bakterizide:Bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel Dimethyldithiocarbamat, Kasugamy¬ cin, Octhilinon, Furancarbonsäure, Oxytetracyclin. Probenazol, Streptomvcin, Tecloftalam, Kupfersulfat und andere Kupfer-ZubereitungenBronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy¬ cin, octhilinone, furan carboxylic acid, oxytetracycline. Probenazole, streptomvcin, tecloftalam, copper sulfate and other copper preparations
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha- methrin, Amitraz, Avermectin, AZ 60541 , Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,Abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alpha-methrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin,Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin,
Bifenthrin, BPMC, Brofenprox. Bromophos A, Bufencarb, Buprofezin.Bifenthrin, BPMC, Brofenprox. Bromophos A, Bufencarb, Buprofezin.
Butocarboxin, Butylpyridaben,Butocarboxin, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap. CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos.Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap. CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chloretoxyfos, chlorfenvinphos.
Chlorfluazuron, Chlormephos, Chlorpyrifos, Chloφyrifos M, Cis-Resmethrin.Chlorfluazuron, Chlormephos, Chlorpyrifos, Chloφyrifos M, Cis-Resmethrin.
Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin.Clocythrin, clofentezin, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin.
Cyhexatin, Cypermethrin, Cyromazin,Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron. Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion.Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron. Diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion.
Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,Diflubenzuron, dimethoate, dimethylvinphos, dioxathione, disulfoton,
Edifenphos, Emamectin. Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox. Ethopro- phos, Etofenprox, Etrimphos,Edifenphos, Emamectin. Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox. Ethoprophos, Etofenprox, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb. Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
Fipronil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Flufenprox, Fluv- alinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb. Fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythπnat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
HCH, Heptenophos, Hexaflumuron, Hexythiazox,HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos,Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin,Methamidophos, methidathione, methiocarb, methomyl, metolcarb, milbemectin,
Monocrotophos, Moxidectin,Monocrotophos, moxidectin,
Naled, NC 184, NI 25, Nitenpyram Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,Naled, NC 184, NI 25, Nitenpyram Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethπn, Phenthoat, Phorat, Phosalon, Phosmet,Parathion A, Parathion M, Permethπn, Phenthoat, Phorat, Phosalon, Phosmet,
Phosphamdon, Phoxim, Piπmicarb, Piπmiphos M, ,Pπmιphos A, Profenofos,Phosphamdon, Phoxim, Piπmicarb, Piπmiphos M,, Pπmιphos A, Profenofos,
Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoat,Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoat,
Pymetrozin, Pyrachlophos, Pyraclofos, Pyraclophos, Pyradaphenthi on, Pyresmethrin, Pyrethrum, Pyridaben, Pyπmidifen, Pyπproxifen,Pymetrozin, Pyrachlophos, Pyraclofos, Pyraclophos, Pyradaphenthi on, Pyresmethrin, Pyrethrum, Pyridaben, Pyπmidifen, Pyπproxifen,
Quinalphos,Quinalphos,
RH 5992,RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthπn, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio- methon, Thionazin, Thuπngiensin, Tralomethπn, Tπarathen, Tπazophos.Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthπn, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuπngiensin, Talarophathos, Tralomethosen, Tralomethosen.
Tnazuron, Trichlorfon, Tπflumuron, Tπmethacarb.Tnazuron, Trichlorfon, Tπflumuron, Tπmethacarb.
Vamidothion, XMC, Xylylcarb, Yl 5301 / 5302, ZetamethπnVamidothion, XMC, Xylylcarb, Yl 5301/5302, Zetamethπn
Gegebenenfalls werden die erfindungsgemaßen Wirkstoffe auch mit anderen bekannten Wirkstoffen, wie Herbiziden oder auch mit Düngemitteln undIf appropriate, the active compounds according to the invention are also used with other known active compounds, such as herbicides or with fertilizers and
Wachstumsregulatoren gemischtGrowth regulators mixed
Die Wirkstoffe werden als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Losungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver. Staubemittel und Granulate angewendet Die Anwendung geschieht in üblicher Weise, z B durch Gießen, Verspritzen,The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders. Dusting agents and granules applied The application takes place in the usual way, e.g. by pouring, spraying,
Versprühen, Verstreuen, Verstauben, Verschaumen, Bestrei chen u sw Gegebenenfalls werden die Wirkstoffe nach dem Ultra-Low-Volume-Verfahren ausgebracht oder die Wirkstoffzubereitung oder der Werkstoff selbst wird in den Boden injiziert Gegebenenfalls wird auch das Saatgut der Pflanzen behandelt
Bei der Behandlung von Pflanzenteilen können die Wirkstoffkonzentrationen in den Anwendungsformen in einem größeren Bereich variiert werden: Sie liegen im allgemeinen zwischen 1 und 0,0001 Gew.-%, vorzugsweise zwischen 0,5 und 0,001 Gew.-%.Spraying, scattering, dusting, foaming, brushing etc. If necessary, the active ingredients are applied using the ultra-low-volume process or the active ingredient preparation or the material itself is injected into the soil. If necessary, the seeds of the plants are also treated In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 59g je Kilogramm Saatgut, vorzugsweise 0,01 bis 10 g benötigtIn the case of seed treatment, amounts of active compound of 0.001 to 59 g per kilogram of seed, preferably 0.01 to 10 g, are generally required
Bei der Behandlung des Bodens sind Wirkstoffkonzentrationen von 0,00001 bis 0, 1 Gew -%, vorzugsweise von 0,0001 bis 0,2 Gew. -% erforderlich
When treating the soil, active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.2% by weight, are required
HerstellunesbeispieleManufacturing examples
Beispiel 1-1:Example 1-1:
(Verfahren a)(Method a)
1 g (0,01197 Mol) Methoxyaminhydrochlorid wird mit 2 g (0,00684 Mol) 2-[2-(2- Methylphenoxymethyl)-benzoyl]-imidazol in 10 ml Ethvlenglykol 1 Stunde auf 150°C erhitzt. Danach versetzt man die Reaktionsmischung mit einer Lösung von 1,3 g Natriumcarbonat in 25 ml Wasser. Man extrahiert mit Essigsäureethylester, trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein wobei das Produkt auskristallisiert. Man erhält 550 mg (25 % der Theorie) 2-{l-[2-(2- Methylphenoxymethyl)-phenyl]-l-(methoximino)-methyl}-imidazol als Stereoiso- merengemisch (E.Z = 8218)1 g (0.01197 mol) of methoxyamine hydrochloride is heated to 150 ° C. with 2 g (0.00684 mol) of 2- [2- (2-methylphenoxymethyl) benzoyl] imidazole in 10 ml of ethylene glycol. A solution of 1.3 g of sodium carbonate in 25 ml of water is then added to the reaction mixture. The mixture is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo, the product crystallizing out. 550 mg (25% of theory) of 2- {l- [2- (2-methylphenoxymethyl) phenyl] -1- (methoximino) methyl} imidazole are obtained as a mixture of stereoisomers (E.Z = 8218)
Η-NMR-Spektrum (CDC1/TMS) δ = 2,146 (3H). 3.932 (3H). 4.977( 2H). 6,724-6,841 (2H), 6.983-7,158 (4H), 7,293-7,322 (1H). 7.371-7.583 (2H). 7,583- 7,630 (1H), 9,917 (1H) ppmΗ NMR spectrum (CDC1 / TMS) δ = 2.146 (3H). 3,932 (3H). 4,977 (2H). 6.724-6.841 (2H), 6.983-7.158 (4H), 7.293-7.322 (1H). 7,371-7,583 (2H). 7.583-7.630 (1H), 9.917 (1H) ppm
Die Mutterlauge wird eingeengt und der Ruckstand mit Diethylether an Kieselgel chromatografiert Man erhalt nach dem AbdesüUieren des Losungsmittels 520 mg (23,7 % der Theorie) isomerenreines Z-2-{ l-[2-(2-Methylphenoxymethyl)-phenyl]- l-(methoximino)-methyl XimidazolThe mother liquor is concentrated and the residue is chromatographed on silica gel using diethyl ether. 520 mg (23.7% of theory) of isomerically pure Z-2- {l- [2- (2-methylphenoxymethyl) phenyl] -1 are obtained after the solvent has been removed - (methoximino) methyl ximidazole
Η-NMR- Spektrum (CDC1 TMS) δ = 2,158 (3H). 4,115 (3H), 5.061 (2H).Η NMR spectrum (CDC1 TMS) δ = 2.158 (3H). 4.115 (3H), 5.061 (2H).
6,697/6,725 (1H), 6.805/6.827 (1H), 7,027-7.3 (4H), 7,3-7,8 (4H). 11,0 (1H) ppm
Herstellung der Ausgangsverbindung.6.697 / 6.725 (1H), 6.805 / 6.827 (1H), 7.027-7.3 (4H), 7.3-7.8 (4H). 11.0 (1H) ppm Preparation of the starting compound.
Beispiel (D-l):Example (D-l):
(Verfahren a-al )(Procedure a-al)
6,9 g (0,0405 Mol) N-Diethoxymethylimidazol (J Org Chem Vol 45, No 20,6.9 g (0.0405 mol) of N-diethoxymethylimidazole (J Org Chem Vol 45, No 20,
1980, Seite 4040) werden in 40 ml Tetrahydrofuran mit 1 1 ,3 g (0,0405 Mol) 23 %igem n-Butyllithium bei - 40°C versetzt und eine Stunde bei - 60°C gerührt Man gibt 6 g (0,0203 Mol) N-[2-(2-Methylphenoxymethyl)-benzoyl]-pyrrolidin bei - 40°C zu und rührt 30 Minuten ohne weitere Kühlung, wobei sich das Reaktionsgemisch auf 20°C erwärmt. Man gibt5 g Ammoniumchlorid und 50 ml1980, page 4040) in 40 ml of tetrahydrofuran with 1 1, 3 g (0.0405 mol) of 23% n-butyllithium at - 40 ° C and stirred for one hour at - 60 ° C. 6 g (0, 0203 mol) of N- [2- (2-methylphenoxymethyl) benzoyl] pyrrolidine at - 40 ° C. and stirred for 30 minutes without further cooling, the reaction mixture heating to 20 ° C. 5 g of ammonium chloride and 50 ml are added
Methanol zu und kocht 15 Minuten unter Rückfluß. Man destilliert die flüchtigen Bestandteile im Vakuum ab, versetzt den Rückstand mit Wasser und extrahiert mit Essigsäureethylester Nach dem Trocknen der organischen Phase engt man im Vakuum ein Der Rückstand wird aus Essigsäureethylester umkristallisiert Man erhält 3,79 g (63,8 % der Theorie) 2-[2-(2-Methylphenoxymethyl )-benzoyl]- imidazolAdd methanol and reflux for 15 minutes. The volatile constituents are distilled off in vacuo, the residue is mixed with water and extracted with ethyl acetate. After the organic phase has been dried, the mixture is concentrated in vacuo. The residue is recrystallized from ethyl acetate. 3.79 g (63.8% of theory) 2 are obtained - [2- (2-methylphenoxymethyl) benzoyl] imidazole
Η-NMR-Spektrum (CDC1XTMS) δ = 2.1 18 (3H). 5,357 (2H), 6,792-6.85 1 (2H). 7,059-7,2(3H), 7,343 ( 1 H), 7.425/7,450/7,476 ( 1 H), 7,537-7.592 ( 1 H), 7.712/7,737 ( 1 H), 8,200-8.230 ( 1H). 1 1.25 ( 1 H) ppm
Η NMR spectrum (CDC1XTMS) δ = 2.1 18 (3H). 5.357 (2H), 6.792-6.85 1 (2H). 7.059-7.2 (3H), 7.343 (1H), 7.425 / 7.450 / 7.476 (1H), 7.537-7.592 (1H), 7.712 / 7.737 (1H), 8.200-8.230 (1H). 1 1.25 (1H) ppm
Herstellung des VorproduktesProduction of the preliminary product
Beispiel (Xa-1)Example (Xa-1)
(Verfahren a-a2)(Procedure a-a2)
15,6 g (0,06 Mol) 2-(2-Methylphenoxymethyl)benzoylchloπd (EP-A 493 71 1 , Seite 22) tropft man bei 20 bis 30°C zu einer Losung von 8,53 g (0, 12 Mol) Pyrrolidin in 40 ml t-Butyl-methylether Man versetzt mit Wasser, trennt die organische Phase ab, trocknet über Natriumsulfat und engt im Vakuum ein Der Rückstand kristallisiert beim Verrühren mit Diisopropylether. Man erhalt 15 g (84,6 % der Theorie) N-[2-(2-Methylphenoxymethyl)-benzoyl]-pyrrolidin15.6 g (0.06 mol) of 2- (2-methylphenoxymethyl) benzoylchloride (EP-A 493 71 1, page 22) are added dropwise at 20 to 30 ° C. to a solution of 8.53 g (0.12 mol ) Pyrrolidine in 40 ml of t-butyl methyl ether. Water is added, the organic phase is separated off, dried over sodium sulfate and concentrated in vacuo. The residue crystallizes when stirred with diisopropyl ether. 15 g (84.6% of theory) of N- [2- (2-methylphenoxymethyl) benzoyl] pyrrolidine are obtained
Η-NMR-Spektrum (CDC13/TMS) δ = 1 ,746- 1 ,952 (4H), 2,236 (3H), 3,205/3,227/3250 (2H), 3,597/3,621/3,643 (2H), 5,126 (2H), 6,842-6,925 (2H), 7, 1 14-7,7, 160 (2H), 7,257-7,441 (3H), 7,593-7,618 (1H) ppm
Η NMR spectrum (CDC1 3 / TMS) δ = 1, 746-1, 952 (4H), 2.236 (3H), 3.205 / 3.227 / 3250 (2H), 3.597 / 3.621 / 3.643 (2H), 5.126 (2H ), 6.842-6.925 (2H), 7.1, 14-7.7, 160 (2H), 7.257-7.441 (3H), 7.593-7.618 (1H) ppm
Beispiel (Xa-2)Example (Xa-2)
(Verfahren a-a2)(Procedure a-a2)
2,6 g (0,01 Mol) 2-(2-Methylphenoxymethyl)benzoylchloπd (EP-A 493 71 1 , Seite 22) tropft man bei 20 bis 30°C zu einer Losung von 1,8 g (0,02 Mol) Morpholin in 40 ml tert -Butyl-methylether Man versetzt mit Wasser, trennt die organische Phase ab, trocknet über Natπumsulfat, engt im Vakuum ein und kristallisiert den Ruckstand aus 5 ml Methanol um Man erhalt 1 ,6 g (51 ,4 % der Theorie) N-[2-(2- Methylphenoxymethyl)-benzoyl]-morpholιn2.6 g (0.01 mol) of 2- (2-methylphenoxymethyl) benzoylchloride (EP-A 493 71 1, page 22) are added dropwise at 20 to 30 ° C. to a solution of 1.8 g (0.02 mol ) Morpholine in 40 ml of tert-butyl methyl ether. Water is added, the organic phase is separated off, dried over sodium sulfate, concentrated in vacuo and the residue is crystallized from 5 ml of methanol. 1.6 g (51.4% of the Theory) N- [2- (2-methylphenoxymethyl) benzoyl] morphol
Η-NMR-Spektrum (CDC13/TMS) δ = 2,245 (3H), 3,32-3,42 (2H), 3,42-3,62Η NMR spectrum (CDC1 3 / TMS) δ = 2.245 (3H), 3.32-3.42 (2H), 3.42-3.62
(2H), 3,62-3,85 (4H), 5,093 (2H), 6,866-6,916 (2H), 7,125-7,171 (2H), 7,235- 7,264 ( 1H), 7,348-7,470 (2H), 7,599-7,624 ( 1H) ppm(2H), 3.62-3.85 (4H), 5.093 (2H), 6.866-6.916 (2H), 7.125-7.171 (2H), 7.235- 7.264 (1H), 7.348-7.470 (2H), 7.599- 7.624 (1H) ppm
Analog den Beispielen (Xa-1 ) und (Xa-2), sowie entsprechend der allgemeinen Verfahrensbeschreibung werden die in Tabelle 32 genannten \ erbindungen der Formel (Xa) hergestellt
Analogously to Examples (Xa-1) and (Xa-2), and in accordance with the general process description, the compounds of the formula (Xa) mentioned in Table 32 are prepared
Tabelle 41:Table 41:
(Xa)(Xa)
Tabelle 41: (Fortsetzung) Table 41: (continued)
Tabelle 41: (Fortsetzung) Table 41: (continued)
Bsp Nr | Z4 G1 R 15 R 16 phys DatenExample no Z 4 G 1 R 15 R 16 phys data
Xa-15 -O-CH,- -H -CH, .vT = 354Xa-15 -O-CH, - -H -CH, .vT = 354
Xa-16 -O-CH,- -H -CH, Ivf = 368Xa-16 -O-CH, - -H -CH, Ivf = 368
Xa-17 -O-CH,- -H -CH, M* = 340Xa-17 -O-CH, - -H -CH, M * = 340
Xa-18 -O-CH,- -H -CH, M* = 366Xa-18 -O-CH, - -H -CH, M * = 366
Xa-19 -O-CH, -H -CH3 M^ = 351Xa-19 -O-CH, -H -CH 3 M ^ = 351
Xa-20 -O-CH,- -H -CH, M = 470Xa-20 -O-CH, - -H -CH, M = 470
L //L //
Xa-2: -O-CH,- -H -CH, M = 434Xa-2: -O-CH, - -H -CH, M = 434
abelle 41: (Fortsetzung) table 41: (continued)
Tabelle 41: (Fortsetzung) Table 41: (continued)
Tabelle 41: (Fortsetzung) Table 41: (continued)
Tabelle 41: (Fortsetzung) Table 41: (continued)
Beispiel (1-3): Example (1-3):
(Verfahren a)(Method a)
1,67 g (0,02 Mol) O-Methylhydroxylammoniumchlorid werden in 10 ml Ethylenglykol mit 2,76 g (0,01 Mol) 2-[2-(2-Methylphenoxymethyl)-benzoyl]-furan eine Stunde auf 140°C erhitzt Man gießt auf Wasser, extrahiert das Produkt mit Essigsäureethylester, trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein Der Ruckstand wird mit tert -Butylmethylether/Petrolether (1 1) an Kieselgel chromatografiert Man erhält 1 g (31,2 % der Theorie) 2-{l-[2-(2- Methylphenoxymethyl)-phenyl ]- l-(methoximino)-methyl}-furan als Stereoisomerengemisch (E.Z = 4452 (HPLC))1.67 g (0.02 mol) of O-methylhydroxylammonium chloride are dissolved in 10 ml of ethylene glycol with 2.76 g (0.01 mol) of 2- [2- (2-methylphenoxymethyl) benzoyl] furan at 140 ° C. for one hour The mixture is poured onto water, the product is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel using tert-butyl methyl ether / petroleum ether (11). 1 g (31.2% of theory) is obtained ) 2- {l- [2- (2-methylphenoxymethyl) phenyl] - l- (methoximino) methyl} furan as a mixture of stereoisomers (EZ = 4452 (HPLC))
Η-NMR-Spektrum (CDC1/TMS) δ = 2,192-2,205, 3,978, 4,087, 5,012, 6.1-7.8 ppmΗ NMR spectrum (CDC1 / TMS) δ = 2.192-2.205, 3.978, 4.087, 5.012, 6.1-7.8 ppm
GC/MS-AnalyseGC / MS analysis
E-lsomeres Retentionsindex 2285, M = 322, 321. 290, 214, 199. 183,E-isomeric retention index 2285, M = 322, 321, 290, 214, 199, 183,
154, 127, 89, 77, 39154, 127, 89, 77, 39
Z-Isomeres Retentionsindex = 2320, M = 321, 290, 246. 214, 199, 183, 154, 127, 89, 7739
Z-isomeric retention index = 2320, M = 321, 290, 246, 214, 199, 183, 154, 127, 89, 7739
Herstellung der Ausgangsverbindung,Preparation of the starting compound,
Beispiel (11-2):Example (11-2):
(Verfahren a-al )(Procedure a-al)
Zu einer auf -20°C gekühlten Losung von 6,8 g (0, 1 Mol) Furan in 100 ml Diethylether tropft man 27,8 g (0,1 Mol) 23%iges n-Butyllithium innerhalb von 15 Minuten zu, rührt 2 Stunden bei 20°C, kühlt wieder auf - 20°C ab und tropft 14,8 g (0,05 Mol) N-[2-(2-Methylphenoxymethyl)-benzoyl]-pyrrolidin gelöst in 100 ml Diethylether innerhalb von 15 Minuten zu Nach vollständigem Umsatz (DC-Kontrolle) gießt man auf 300 ml eiskalte Ammonium chlorid-Losung und extrahiert mit Essigsäureethylester Man trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein Man erhalt 13,1 g (89,7 % der Theorie) 2-[2-(2-Methylphenoxymethyl)-benzoyl]-furan27.8 g (0.1 mol) of 23% n-butyllithium are added dropwise to a solution of 6.8 g (0.1 mol) furan in 100 ml diethyl ether cooled to -20 ° C. over the course of 15 minutes, and the mixture is stirred 2 hours at 20 ° C., cools again to −20 ° C. and 14.8 g (0.05 mol) of N- [2- (2-methylphenoxymethyl) benzoyl] pyrrolidine dissolved in 100 ml of diethyl ether are added dropwise within 15 Minutes after complete conversion (TLC control), pour onto 300 ml of ice-cold ammonium chloride solution and extract with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated in vacuo. 13.1 g (89.7% of theory) are obtained. 2- [2- (2-methylphenoxymethyl) benzoyl] furan
Η-NMR-Spektrum (CDC1 TMS) δ = 2,129 (3H), 5.266 (2H), 6,536-6,554 ( 1 H), 6,803-6.849 (2H), 7,0-7,763 (8H) ppm
Η NMR spectrum (CDC1 TMS) δ = 2.129 (3H), 5.266 (2H), 6.536-6.554 (1H), 6.803-6.849 (2H), 7.0-7.763 (8H) ppm
Beispiel fl-4.:Example fl-4 .:
(Verfahren a)(Method a)
1 ,45 g (0,005 Mol) 3-[2-(2-Methylphenoxymethyl)-benzoyl]-trιazol werden mit 1,25 g (0,015 Mol) O-Methylhydroxyl-ammoniumchlorid in 5 ml Ethylenglykol 2 Stunden auf 1 80°C erhitzt Man vesetzt mit wäßriger Natπumhvdrogen- carbonatlosung, extrahiert mit Essigsäureethylester, trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein Der Ruckstand wird mit Diethylether Petrolether (3 1 ) an Kieselgel chromatografiert Man erhalt 0.7 g (43 % der Theorie) 3-{ l-[2-(2-Methylphenoxymethyl)-phenyl]- l -(methoximino)- methyl }-triazol als Stereoisomerengemisch (E.Z = 59 24 (HPLC))1.45 g (0.005 mol) of 3- [2- (2-methylphenoxymethyl) benzoyl] trιazol are heated at 1.25 g (0.015 mol) of O-methylhydroxylammonium chloride in 5 ml of ethylene glycol at 180 ° C. for 2 hours It is mixed with aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with diethyl ether, petroleum ether (3 l). 0.7 g (43% of theory) of 3- {l - [2- (2-methylphenoxymethyl) phenyl] - l - (methoximino) - methyl} -triazole as a mixture of stereoisomers (EZ = 59 24 (HPLC))
Η-NMR-Spektrum (CDC1 TMS) δ = 2 077, 2,1 12, 4,010, 4.167, 4.974, 5.072, 6,6-8, 1 ppm
Η NMR spectrum (CDC1 TMS) δ = 2 077, 2.1 12, 4.010, 4,167, 4,974, 5,072, 6.6-8, 1 ppm
Herstellung der Ausgangsverbindung.Preparation of the starting compound.
Beispiel (II-3):Example (II-3):
(Verfahren a-al )(Procedure a-al)
In eine Losung von 1 ,7 g (0,01 Mol ) N-Diethoxymethyltriazol 1 0 mlIn a solution of 1.7 g (0.01 mol) of N-diethoxymethyltriazole 10 ml
Tetrahydrofuran werden bei - 20°C 2,8 g (0,01 Mol) 23 %iges n-Butyllithium innerhalb von 15 Minuten zugetropft Nach weiteren 15 Minuten Ruhren bei -20°C gibt man 1 ,48 g (0,005 Mol) N-[2-(2-Methylphenoxymethyl)-benzoyl]-pyrrolidin, gelost in 10 ml Tetrahydrofuran, zu und rührt nochmals 30 Minuten bei - 20°C Man gibt 2 g Ammoniumchlorid und 10 ml Methanol zu und kocht 15 Minuten unter Rückfluß Man zieht die fluchtigen Bestandteile ab, versetzt den Ruckstand mit Wasser und extrahiert mit Essigsäureethylester, trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein Der Ruckstand kristallisiert beim Versetzen mit einer Mischung aus Diethylether und Petrolether im Verhältnis 1 1 Man erhalt 0,5 g (17 % der Theorie) 3-[2-(2-Methylphenoxvmethvl)-benzovl]- tπazol vom Schmelzpunkt 179°CTetrahydrofuran 2.8 g (0.01 mol) of 23% n-butyllithium are added dropwise at −20 ° C. After 15 minutes of stirring at −20 ° C., 1.48 g (0.005 mol) of N- [2- (2-Methylphenoxymethyl) benzoyl] pyrrolidine, dissolved in 10 ml of tetrahydrofuran, and stirred again for 30 minutes at -20 ° C. 2 g of ammonium chloride and 10 ml of methanol are added and the mixture is boiled under reflux for 15 minutes volatile constituents, the residue is mixed with water and extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo. The residue crystallizes when mixed with a mixture of diethyl ether and petroleum ether in a ratio of 1 1. 0.5 g (17% of theory) 3- [2- (2-Methylphenoxvmethvl) -benzovl] - tπazol with a melting point of 179 ° C.
Η-NMR-Spektrum (CDC1./TMS) δ = 1 ,884 (3H), 5.224 (2H). 6,769-6,866 (2H ) 7,047-7, 104 (2H), 7,379-7.505 (1H), 7,502-7,688 (2H), 7,688-7,85 ( 1 H), 8.65: ( 1 H), 14,742 ( 1H) ppm
Herstellung des VorproduktesΗ NMR spectrum (CDC1./TMS) δ = 1.884 (3H), 5.224 (2H). 6.769-6.866 (2H) 7.047-7, 104 (2H), 7.379-7.505 (1H), 7.502-7.688 (2H), 7.688-7.85 (1H), 8.65: (1H), 14.742 (1H) ppm Production of the preliminary product
(analog zur Herstellung des N-Diethoxymethylimidazols nach J Org Chem Voi 45, No 20, 1980, Seite 4040)(analogous to the preparation of N-diethoxymethylimidazole according to J Org Chem Voi 45, No 20, 1980, page 4040)
34,5 g (0,5 Mol) Triazol werden in 222 g (1,5 Mol) Orthoameisensäuretriethylester nach Zugabe von 2,5 g p-Toluolsulfonsaure-Hydrat unter AbdesüUieren von34.5 g (0.5 mol) of triazole are dissolved in 222 g (1.5 mol) of triethyl orthoformate after the addition of 2.5 g of hydrate of p-toluenesulfonate with removal of
Ethanol erhitzt, bis die Innentemperatur 1 50°C erreicht Man gibt 2 g Natriumcarbonat zu, und destilliert das Gemisch im Hochvakuum Man erhalt 48,6 g (56,8 % der Theorie) N-Di ethoxy methyltriazolEthanol heated until the internal temperature reaches 1 50 ° C. 2 g of sodium carbonate are added, and the mixture is distilled under high vacuum. 48.6 g (56.8% of theory) of N-di ethoxy methyltriazole are obtained
Η-NMR-Spektrum (CDC13/TMS) δ = 1 ,247/1 ,270/1 ,294 (6H), 3,647/3,671/3,694/3,718 (4H), 6,262 (1H), 7,994 OH), 8,443 (1H) ppm
Η NMR spectrum (CDC1 3 / TMS) δ = 1, 247/1, 270/1, 294 (6H), 3.647 / 3.671 / 3.694 / 3.718 (4H), 6.262 (1H), 7.994 OH), 8.443 ( 1H) ppm
Beispiel (1-5):Example (1-5):
(Verfahren b)(Method b)
5,6 g (0,015 Mol) 2-(Methoximino)-2-{2-[ l -(3-tπfluormethylphenyl)-ethyliden- aminooxymethyl]-phenyl }-acetonitril (vgl WO-A 94/26700) werden mit 1 ,6 g (0,015 Mol) Aminoacetaldehyddimethylacetal 2 Stunden unter Ruckfluß erhitzt Man versetzt mit wäßriger Salzsaure, neutralisiert mit wäßriger Natriumcarbonat- Losung, extrahiert mit Essigsäureethylester, trocknet die organische Phase über Natriumsulfat und engt im Vakuum ein Der Ruckstand wird mit tert - Butylmethylether/Petrolether (3.1) an Kieselgel chromatografiert Man erhalt 2-{ l- (Methoximino)-l -[2-(3-trifluormethylphenyl>-ethyliden-aminooxymethyl)-phenyl]- methyl }-imidazoI5.6 g (0.015 mol) of 2- (methoximino) -2- {2- [l - (3-tπfluoromethylphenyl) ethylidene aminooxymethyl] phenyl} acetonitrile (cf. WO-A 94/26700) are mixed with 1, 6 g (0.015 mol) of aminoacetaldehyde dimethyl acetal are heated under reflux for 2 hours. Aqueous hydrochloric acid is added, the mixture is neutralized with aqueous sodium carbonate solution, extracted with ethyl acetate, the organic phase is dried over sodium sulfate and concentrated in vacuo. 3.1) Chromatographed on silica gel. 2- {l- (Methoximino) -1 - [2- (3-trifluoromethylphenyl> ethylidene aminooxymethyl) phenyl] methyl} imidazole is obtained
Beispiel (1-6):Example (1-6):
(Verfahren a)(Method a)
Zu 1 ,65 g (0,0198 Mol) O-Methylhydroxylammoniumchlorid in 10 ml Methanol gibt man 1 ,07g (0,0198 Mol) Natπummethylat und dann 3 g (0,00988 Mol) 2-[2- (2-Methylphenoxymethyl)-benzoyl]-pyridin Man kocht 2 Stunden unter Ruckfluß Dann gibt man nochmals 0,82 g O-Methyl-hydroxylammoniumchlorid und 0,53 g Natriummethvlat zu und kocht nochmals 2 Stunden unter Ruckfluß Man gießt auf
Wasser, extrahiert mit Diethylether, trocknet über Natriumsulfat und engt die Losing im Vakuum ein. Man erhält 2,3 g (69,9 % der Theorie) an 2-{ l-[2-(2- Methylphenoxymethyl)-phenyl]-l-(methoximino)-methyl }-pyridin Stereoisomeren- gemisch (E:Z = 75.25 (GC/MS))1.07 g (0.0198 mol) of sodium methylate and then 3 g (0.00988 mol) of 2- [2- (2-methylphenoxymethyl) are added to 1.65 g (0.0198 mol) of O-methylhydroxylammonium chloride in 10 ml of methanol. -benzoyl] -pyridine. The mixture is boiled under reflux for 2 hours. Then another 0.82 g of O-methyl-hydroxylammonium chloride and 0.53 g of sodium methoxide are added and the mixture is boiled under reflux for another 2 hours Water, extracted with diethyl ether, dried over sodium sulfate and concentrated the Losing in vacuo. 2.3 g (69.9% of theory) of 2- {l- [2- (2-methylphenoxymethyl) phenyl] -1- (methoximino) methyl} pyridine stereoisomer mixture (E: Z = 75.25 (GC / MS))
Η-NMR-Spektrum (CDC13/TMS) δ = 2,172 (3H, E), 2,246 (3H, Z), 3,999 (3H,Η NMR spectrum (CDC1 3 / TMS) δ = 2.172 (3H, E), 2.246 (3H, Z), 3.999 (3H,
Z), 4,040 (3H, E), 4,956 (2H, E), 5,008 (2H, Z), 6,6-6,9 (2H, E+Z), 7,0-7,15 (2H, E+Z), 7,125-7,3 (2H, E+Z), 7,38-7,5 (2H, E+Z), 7,55-7,75 (3H, E+Z), 8,6-8,7 ( 1 H, E+Z) ppmZ), 4.040 (3H, E), 4.956 (2H, E), 5.008 (2H, Z), 6.6-6.9 (2H, E + Z), 7.0-7.15 (2H, E + Z), 7.125-7.3 (2H, E + Z), 7.38-7.5 (2H, E + Z), 7.55-7.75 (3H, E + Z), 8.6 -8.7 (1H, E + Z) ppm
GC/MS-AnalyseGC / MS analysis
E-Isomeres Retentionsindex = 2463E-isomeric retention index = 2463
M = 333, 332, 301 , 186, 241 , 225, 193, 168, 152, 1 16, 89, 78, 51M = 333, 332, 301, 186, 241, 225, 193, 168, 152, 1 16, 89, 78, 51
Z-Isomeres Retentionsindex = 2509Z-isomeric retention index = 2509
M = 303, 301 , 283, 257, 225, 193, 168, 152, 1 16, 89, 78, 51
M = 303, 301, 283, 257, 225, 193, 168, 152, 1 16, 89, 78, 51
Herstellung der AusgangsverbindungPreparation of the starting compound
Beispiel (IΪ-4):Example (IΪ-4):
(Verfahren a-cl)(Procedure a-cl)
10 g (0,036 Mol) 2-[(2-Methylphenoxy)-methyl]-l-brom-benzoI (EP-A 525 516.10 g (0.036 mol) of 2 - [(2-methylphenoxy) methyl] -1-bromo-benzoI (EP-A 525 516.
Seite 113) werden in 40 ml Tetrahydrofuran gelöst Man gibt 3 g dieser Losung zu 0,88 g (0,036 Mol) Magnesiumspänen Nach Zugabe von einem Tropfen Brom kocht man auf Nach Anspringen der Reaktion, gibt man den Rest der in Tetrahydrofuran gelösten Bromverbindung zu und kocht eine Stunde unter Rückfluß. Dann gibt man bei -20°C 3,76 g (0,036 Mol) 2-Cyanpyridin, gelöst inPage 113) are dissolved in 40 ml of tetrahydrofuran. 3 g of this solution are added to 0.88 g (0.036 mol) of magnesium shavings. After adding a drop of bromine, the mixture is boiled up boils under reflux for an hour. Then 3.76 g (0.036 mol) of 2-cyanopyridine, dissolved in, are added at -20.degree
10 ml Tetrahydrofuran, zum Reaktionsgemisch zu und rührt 1 Stunde bei -20°C. Man versetzt mit einer Lösung von 10 g Ammoniumchlorid in 100 ml Wasser und extrahiert das rohe Zwischenprodukt (das Ketimin des Endproduktes) mit Diethylether Nach dem Einengen der Lösung versetzt man den Ruckstand mit einer Mischung aus 15 ml 36 %iger wäßriger Salzsaure.50 ml Wasser und 100 ml10 ml of tetrahydrofuran, to the reaction mixture and stirred at -20 ° C for 1 hour. A solution of 10 g of ammonium chloride in 100 ml of water is added and the crude intermediate (the ketimine of the end product) is extracted with diethyl ether. After the solution has been concentrated, the residue is mixed with a mixture of 15 ml of 36% aqueous hydrochloric acid. 50 ml of water and 100 ml
Dimethylformamid Nach einstundigem Ruhren bei 25°C gibt man Eis zu, stellt mit 50 %iger Natronlauge alkalisch und extrahiert mit Diethylether. Die organische Phase wird über Natriumsulfat getrocknet und im Vakuum eingeengt Der Rückstand wird mit Diethylether/Petrolether (1 1) an Kieselgel chromatografiert. Man erhält 3,94 g (36Xo der Theorie) 2-[2-(2-Methyl- phenoxymethyl)-benzoyl]-pyridinDimethylformamide After stirring for 1 hour at 25 ° C, ice is added, made alkaline with 50% sodium hydroxide solution and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel using diethyl ether / petroleum ether (11). 3.94 g (36Xo of theory) of 2- [2- (2-methylphenoxymethyl) benzoyl] pyridine are obtained
Η-NMR-Spektrum (CDC1./TMS): δ = 2,127 (3H).5.211 (2H).6,698/6.725 (1H). 6.777-6,829 ( 1H); • 7,015-7,088 (2H), 7,397-7,442 (2H). 7.528-7.638 (2H). 7.683/7,685 (1H), 7,709-7,835 (1H); 8.019-8.052 (1H), 8,656-8,680 (1H) ppm
GC MS-Analyse:Η NMR spectrum (CDC1./TMS): δ = 2.127 (3H) .5.211 (2H) .6.698 / 6.725 (1H). 6,777-6,829 (1H); • 7.015-7.088 (2H), 7.397-7.442 (2H). 7.528-7.638 (2H). 7,683 / 7,685 (1H), 7,709-7,835 (1H); 8,019-8,052 (1H), 8,656-8,680 (1H) ppm GC MS analysis:
Retentionsindex = 2479Retention index = 2479
M = 305, 303, 285, 257, 225, 196, 167, 139, 1 15, 89, 78, 51M = 305, 303, 285, 257, 225, 196, 167, 139, 1 15, 89, 78, 51
Beispiel (1-7):Example (1-7):
HH
(Verfahren b)(Method b)
1 g (0,0034 Mol) 2-Methoximino-2-[2-(2,4-dimethylphenoxymethyl)-phenyl]- acetonitril werden mit 0,2 g (0,0332 Mol) Ethylendiamin vermischt und 1 Stunde bis zum Ende der Gasentwicklung auf 100°C erwärmt Man kristallsiert aus wenig Ethanol um und erhält 0,65 g (56,7 % der Theorie) 2-{ l-Methoximino-l-[2-(2,4- dimethylphenoxymethyl)-phenyl]-methyl }-4,5-dihydro- lH-imidazol1 g (0.0034 mol) of 2-methoximino-2- [2- (2,4-dimethylphenoxymethyl) phenyl] acetonitrile are mixed with 0.2 g (0.0332 mol) of ethylenediamine and 1 hour until the end of Gas evolution heated to 100 ° C. One crystallizes from a little ethanol and 0.65 g (56.7% of theory) of 2- {l-methoximino-l- [2- (2,4-dimethylphenoxymethyl) phenyl] methyl is obtained } -4,5-dihydro-lH-imidazole
Η-NMR-Spektrum (CDC1/TMS) δ = 2.212 (3H). 2.276 (3H). 3.682 (4H), 3,947 (3H), 4.956 (2H), 6,616-6,669 (2H). 6.996-7,020 ( 1H). 7,210-7.243 ( 1 H), 7.3.37- 7,425 (2H), 7,556/7,579 ( 1H) ppm
Η NMR spectrum (CDC1 / TMS) δ = 2.212 (3H). 2.276 (3H). 3,682 (4H), 3,947 (3H), 4,956 (2H), 6,616-6,669 (2H). 6,996-7,020 (1H). 7.210-7.243 (1H), 7.3.37- 7.425 (2H), 7.556 / 7.579 (1H) ppm
Herstellung der Ausgangsverbindung.Preparation of the starting compound.
3,2 g (0.0404 Mol) Pyridin werden mit 6,2 g (0,0198 Mol) 2-Methoximino-2-[2- (2,4-dimethylphenoxymethyl)-phenyl]-acetamid (Beispiel Nr. 2 aus EP-A 596 692) in 50 ml Dichlormethan vorgelegt. Man gibt unter Kühlen 4,6 g (0,0219 Mol) Trifluoressigsäureanhydrid zu und läßt die Mischung eine Stunde bei Raum¬ temperatur stehen. Man wäscht mit Wasser und mit Natriumhydrogencarbonat- Lösung. Nach dem Abziehen des Lösungsmittels erhält man 5,7 g (97,6 % der Theorie) 2-Methoximino-2-[2-(2,4-dimethylphenoxymethyl)-phenyl]-acetonitril.3.2 g (0.0404 mol) of pyridine are mixed with 6.2 g (0.0198 mol) of 2-methoximino-2- [2- (2,4-dimethylphenoxymethyl) phenyl] acetamide (Example No. 2 from EP- A 596 692) in 50 ml dichloromethane. 4.6 g (0.0219 mol) of trifluoroacetic anhydride are added with cooling and the mixture is left to stand at room temperature for one hour. It is washed with water and with sodium hydrogen carbonate solution. After the solvent has been stripped off, 5.7 g (97.6% of theory) of 2-methoximino-2- [2- (2,4-dimethylphenoxymethyl) phenyl] acetonitrile are obtained.
Η-NMR-Spektrum (CDC1/TMS): δ = 2,230 (3H), 2,31 1 (3H), 4,036 (3H); 5,01 1Η NMR spectrum (CDC1 / TMS): δ = 2.230 (3H), 2.31 1 (3H), 4.036 (3H); 5.01 1
(2H); 6,628 ( 1H); 6,687/6,712 (1H); 7,021/7,046 ( 1 H). 7,361 -7,529 (3H); 7,594/7,596 ( 1H) ppm.
(2H); 6.628 (1H); 6.687 / 6.712 (1H); 7.021 / 7.046 (1H). 7.361 -7.529 (3H); 7.594 / 7.596 (1H) ppm.
Beispiel 1-8:Example 1-8:
(Verfahren b)(Method b)
l g (0,0034 Mol) 2-Methoximino-2-[2-(2,4-dimethylphenoxymethyl)-phenyl]- acetonitril werden mit 250 mg (0,00337 Mol) 1.3-Diaminopropan vermischt und 1 Stunde auf 100°C erwärmt. Man kristallisiert aus 5 ml Ethanol um und erhält 630 mg 2-{ l -Methoximino-l -[2-(2,4-dimethylphenoxymethyl)-phenyl]-methyl } - 1 ,4,5,6-tetrahydro-pyrimidin vom Schmelzpunkt 144-145°C1 g (0.0034 mol) of 2-methoximino-2- [2- (2,4-dimethylphenoxymethyl) phenyl] acetonitrile are mixed with 250 mg (0.00337 mol) of 1,3-diaminopropane and heated to 100 ° C. for 1 hour . It is recrystallized from 5 ml of ethanol and 630 mg of 2- {l-methoximino-l - [2- (2,4-dimethylphenoxymethyl) -phenyl] -methyl} - 1, 4,5,6-tetrahydro-pyrimidine are obtained from the melting point 144-145 ° C
Η-NMR-Spektrum (CDC1 TMS): δ = 1,716-1 ,793 (2H); 2,225 (3H); 2,278 (3H), 3,39-3,417 (4H), 3,905 (3H); 4,958 (2H); 6,629-6,669 (2H), 7,0-7,025 ( 1H), 7, 158- 7, 187 (1H), 7,305-7,399 (2H), 7,518-7,547 (1H) ppm.
Η NMR spectrum (CDC1 TMS): δ = 1.716-1, 793 (2H); 2.225 (3H); 2.278 (3H), 3.39-3.417 (4H), 3.905 (3H); 4.958 (2H); 6.629-6.669 (2H), 7.0-7.025 (1H), 7, 158-7, 187 (1H), 7.305-7.399 (2H), 7.518-7.547 (1H) ppm.
Beispiel (1-9):Example (1-9):
(Verfahren b)(Method b)
5,6 g (0,015 Mol) 2-(Methoximino)-2-{2-[ l -(3-trifluormethylphenyl)-ethyliden- aminooxymethyl]-phenyl}-acetonitril (vgl. WO-A 94/26700) werden mit 1 , 1 1 g (0,015 Mol) 1.3-Diaminopropan 1 Stunde lang auf 100°C erwärmt. Man erhält 2- { l-(Methoximino)-l -{2-[ l-(3-trifluormethylphenyl)-ethyliden-aminooxymethyl]- phenyl}-methyl}-l ,4,5,6-tetrahydro-pyrimidin.5.6 g (0.015 mol) of 2- (methoximino) -2- {2- [l - (3-trifluoromethylphenyl) ethylidene aminooxymethyl] phenyl} acetonitrile (cf. WO-A 94/26700) are mixed with 1 , 1 1 g (0.015 mol) of 1,3-diaminopropane heated to 100 ° C for 1 hour. 2- {l- (Methoximino) -l - {2- [l- (3-trifluoromethylphenyl) -ethylidene-aminooxymethyl] -phenyl} -methyl} -l, 4,5,6-tetrahydro-pyrimidine are obtained.
GC/MS-Analyse:GC / MS analysis:
Retentionsindex = 2672Retention index = 2672
M = 431 , 401, 393, 246, 216, 198, 186. 145, 1 16, 84. 55, 30
M = 431, 401, 393, 246, 216, 198, 186, 145, 1 16, 84, 55, 30
Beispiel ( 1-10):Example (1-10):
(Verfahren b)(Method b)
5,6 g (0,015 Mol) 2-(Methoximino)-2-{2-[ l-(3-trifluormethylphenyl)-ethyliden- aminooxymethyl]-phenyl }-acetonitril (vgl WO-A 94/26700) werden mit 0,9 g (0,015 Mol) Ethylendiamin 2 Stunden auf 100°C erhitzt Nach Chromatographie in Petrolether/tert -Butylmethylether (1.1) erhält man 3,5 g (55,7 % der Theorie) 2- { 1 -(Methoximino)- 1 -{2-[ 1 -(3-trifluormethylphenyl)-ethyliden-aminooxymethyl]- phenyl}-methyl }-4,5-dihydro-lH-imidazol5.6 g (0.015 mol) of 2- (methoximino) -2- {2- [1- (3-trifluoromethylphenyl) ethylidene aminooxymethyl] phenyl} acetonitrile (cf. WO-A 94/26700) are 9 g (0.015 mol) of ethylenediamine heated to 100 ° C. for 2 hours. Chromatography in petroleum ether / tert-butyl methyl ether (1.1) gives 3.5 g (55.7% of theory) 2- {1 - (methoximino) - 1 - {2- [1 - (3-trifluoromethylphenyl) ethylidene aminooxymethyl] phenyl} methyl} -4,5-dihydro-1H-imidazole
GC MS-AnalyseGC MS analysis
Retentionsindex = 2595Retention index = 2595
M = 419, 379. 359, 232. 201. 184. 145, 1 16, 89, 70. 44M = 419, 379, 359, 232, 201, 184, 145, 1 16, 89, 70, 44
Η-NMR-Spektrum (CDC1 TMS)NMR NMR spectrum (CDC1 TMS)
δ = 2,235 (3H), 3.3-3.9 (4H), 3.936 (3H), 7, 1 -8,0 (8H) ppm
δ = 2.235 (3H), 3.3-3.9 (4H), 3.936 (3H), 7.1, -8.0 (8H) ppm
Beispiel (1-11):Example (1-11):
(Verfahren c)(Method c)
13,7 g (0,04 Mol) Methoxymethyltriphenylphosphoniumchlorid werden in 40 ml Tetrahydrofuran mit 4,5 g (0,04 Mol) Kalium-tert -butylat 30 Minuten bei 20°C gerührt. Dann gibt man 2,9 g (0,01 Mol) 2-[2-(2-Methylphenoxymethyl)-benzoyl]- furan zu, kocht 2 Stunden unter Rückfluß, gibt Wasser und Essigsäureethylester zu, engt die organische Phase ein und chromatographiert den Rückstand mit Petrolether/Diethylether (3.1) an Kieselgel Man erhält 1 ,4 g (43,7 % der Theorie) 2-{ l-[2-(2-Methylphenoxymethyl)-phenyl]-2-(methoxy)-ethenyl }-furan als Stereo- isomerengemisch (E ' Z = 70 30 )13.7 g (0.04 mol) of methoxymethyltriphenylphosphonium chloride are stirred in 40 ml of tetrahydrofuran with 4.5 g (0.04 mol) of potassium tert-butoxide at 20 ° C. for 30 minutes. Then 2.9 g (0.01 mol) of 2- [2- (2-methylphenoxymethyl) benzoyl] furan are added, the mixture is boiled under reflux for 2 hours, water and ethyl acetate are added, the organic phase is concentrated and the residue is chromatographed Residue with petroleum ether / diethyl ether (3.1) on silica gel. 1.4 g (43.7% of theory) of 2- {l- [2- (2-methylphenoxymethyl) phenyl] -2- (methoxy) ethenyl} - are obtained. furan as a stereo isomer mixture (E 'Z = 70 30)
]H-NMR-Spektrum (CDC13/TMS), E-Isomeres δ = 2.264 (3H), 3,715 (3H), 5,046 (2H), 5,681/5,692 ( 1H), 6,273-6,290 ( 1 H), 6,6-7.8 (9 H) ppm
] H NMR spectrum (CDC1 3 / TMS), E isomer δ = 2,264 (3H), 3.715 (3H), 5.046 (2H), 5.681 / 5.622 (1H), 6.273-6.290 (1H), 6. 6-7.8 (9H) ppm
Beispiel (1-12):Example (1-12):
(Verfahren b)(Method b)
Eine Losung von 6,3 g (0,01 Mol) 40%iges N-[2-(2-Methylphenoxymethyl)- phenyl]-N-methyl-cyanamid, 1, 1 g (0,01 Mol) Thioglykolsaurmethylester und 0, 15 g Triethylamin in 100 ml Ethanol werden 18 Stunden unter Rückfluß erhitzt Die Mischung wird eingeengt und der Rückstand wird mit Cyclohexan/Essigester (1 3) an Kieselgel chromatografiert Man erhält 1,4 g (43 % der Theorie) an 2- {Methyl-[2-(2-methylphenoxymethyl)-phenyl]-amino}-thiazol-4-onA solution of 6.3 g (0.01 mol) of 40% N- [2- (2-methylphenoxymethyl) phenyl] -N-methyl-cyanamide, 1.1 g (0.01 mol) of thioglycolic acid methyl ester and 0.1 15 g of triethylamine in 100 ml of ethanol are refluxed for 18 hours. The mixture is concentrated and the residue is chromatographed on silica gel using cyclohexane / ethyl acetate (1 3). 1.4 g (43% of theory) of 2- {methyl- [2- (2-methylphenoxymethyl) phenyl] amino} thiazol-4-one
Η-NMR (CDCl/EvlS) δ = 2,26 (s, 3H), 3,62 (s, 3H), 3,90 (s, 3H), 5,015 (q, 2H)Η NMR (CDCl / EvlS) δ = 2.26 (s, 3H), 3.62 (s, 3H), 3.90 (s, 3H), 5.015 (q, 2H)
Analog erhalt man 2-J Methyl-[2-(2-methylphenoxymethvl)-phenyl]-amιno thιazol-4-on. Beispiel (1-13) vom Schmelzpunkt 155°C
Analogously, 2-J methyl- [2- (2-methylphenoxymethvl) phenyl] amino thiazol-4-one is obtained. Example (1-13) with melting point 155 ° C
Herstellung der Ausgangsverbindung für Beispiel 1-12.Preparation of the starting compound for Example 1-12.
Beispiel (IVa-l):Example (IVa-l):
1 g (0,024 Mol) 60% Natriumhydrid-Suspension wird in 10 ml Dimethylformamid suspendiert, mit einer Lösung von 2,2 g (0,02 Mol) ortho-Kresol in 10 ml Dimethylformamid versetzt und die Mischung 40 Minuten bei 20°C gerührt Hierzu gibt man eine Lösung von 1 1 ,3 g (0,02 Mol) 40%iges N-(2-Brommethyl- phenyl)-N-methyl-cyanamid in 10 ml Dimethylformamid und rührt 18 Stunden bei 20°C. Die Mischung wird auf 200 ml Eis/Kochsalzlösung gegossen und mit Ether extrahiert. Die vereinigten organischen Phasen werden über Na,SO4 getrocknet und im Vakuum eingeengt. Der Rückstand wird mit Cyclohexan/Essigester (3 : 1 ) an Kieselgel chromatografiert. Man erhält 6,3 g N-[2-(2-Methylphenoxymethyl)- phenyl]-N-methyl-cyanamid mit einem Gehalt von 40 % (HPLC)1 g (0.024 mol) of 60% sodium hydride suspension is suspended in 10 ml of dimethylformamide, a solution of 2.2 g (0.02 mol) of ortho-cresol in 10 ml of dimethylformamide is added and the mixture is stirred at 20 ° C. for 40 minutes A solution of 11.3 g (0.02 mol) of 40% N- (2-bromomethylphenyl) -N-methyl-cyanamide in 10 ml of dimethylformamide is added and the mixture is stirred at 20 ° C. for 18 hours. The mixture is poured onto 200 ml of ice / saline and extracted with ether. The combined organic phases are dried over Na, SO 4 and concentrated in vacuo. The residue is chromatographed on silica gel using cyclohexane / ethyl acetate (3: 1). 6.3 g of N- [2- (2-methylphenoxymethyl) phenyl] -N-methyl-cyanamide are obtained with a content of 40% (HPLC)
Η-NMR (CDC1/TMS). δ = 2.41 (s, 3H), 5,20 (s, 2H) ppmΗ NMR (CDC1 / TMS). δ = 2.41 (s, 3H), 5.20 (s, 2H) ppm
Analog erhält man N-[2-(2.4-Dimethylphenoxymethyl )-phenyl]-Vmethvl-cvanarnιd Beispiel (IVa-2) (Ausgangsverbindung für Beispiel 1- 13 )Analogously, N- [2- (2,4-dimethylphenoxymethyl) phenyl] -Vmethvl-cvanarnιd Example (IVa-2) (starting compound for Example 1-13)
Η-NMR (CDCL/TMS) δ = 2.22 (s, 3H), 2.38 (s, 3H). 5, 16 (s, 2H) ppm
Η NMR (CDCL / TMS) δ = 2.22 (s, 3H), 2.38 (s, 3H). 5, 16 (s, 2H) ppm
Herstellung des Vorproduktes:Production of the preliminary product:
Beispiel (XXII-1)Example (XXII-1)
22,6 g (0,155 Mol) N-(2-Methylphenyl)-N-methyl-cyanamid werden in 300 ml Tetrachl ormethan gel öst, mi t ca . 5 g N-B rom succi ni m i d und 0, 1 g22.6 g (0.155 mol) of N- (2-methylphenyl) -N-methyl-cyanamide are dissolved in 300 ml of tetrachloromethane, with approx. 5 g N-B rom succi ni m i d and 0.1 g
Azodiisobutyronitril versetzt, und unter Rühren 5 Stunden lang mit einer UV- Lampe (250 W) bestrahlt. Während dieser Zeit wird portionsweise weiteres N- Bromsuccinimid zugegeben, insgesamt 32,9 g (0,185 Mol). Die Temperatur steigt während der Reaktion an, bis die Lösung unter Rückfluß siedet Die Reaktionsmischung wird abgekühlt, filtriert und das Filtrat im Vakuum eingeengtAzodiisobutyronitrile added, and irradiated with stirring for 5 hours with a UV lamp (250 W). During this time, further N-bromosuccinimide is added in portions, a total of 32.9 g (0.185 mol). The temperature rises during the reaction until the solution boils under reflux. The reaction mixture is cooled, filtered and the filtrate is concentrated in vacuo
Man erhält 30 g N-(2-Brommethyl-phenyl)-N-methyl-cyanamid mit einem Gehalt von 40 % (HPLC).30 g of N- (2-bromomethyl-phenyl) -N-methyl-cyanamide with a content of 40% (HPLC) are obtained.
1H-NMR (CDC1 TMS) δ = 3,37 (s, 3H); 4,66 (s. 2H) ppm
1H NMR (CDC1 TMS) δ = 3.37 (s, 3H); 4.66 (see 2H) ppm
Beispiel (1-14):Example (1-14):
(Verfahren d)(Method d)
Eine Losung von 1 ,6 g (0,0051 Mol) 2-Methoximιno-2-[2-(2-methylphenoxy- methyl)-phenyl]-thioacetamid und 1 ,5 g (0,0076 Mol ) Bromacetaldehyd¬ diethylacetal in 50 ml Ethanol werden unter Ruckfluß erhitzt Nach 18 Stunden wird ein weiteres Gramm Bromacetaldehyddiethylacetal, sowie 1 ml Eisessig zugegeben und weitere 5 Stunden unter Ruckfluß erhitzt Die Mischung wird eingeengt und der Rückstand wird mit Dichlormethan aufgenommen, zuerst mit Natriumhydrogencarbonatlosung, dann mit Wasser gewaschen Die organische Phase wird abgetrennt, über Natriumsulfat getrocknet und eingeengt Der Ruckstand wi rd mit Cycl ohexan/Essigester (3 1 ) an 1 00 g Ki eselgel chromatografiert Man erhalt 1 ,01 g (59 % der Theorie) 2-{ methoxιmιno-[2-(2- methylphenoxymethyl)-phenyl]-methyl }-thiazolA solution of 1.6 g (0.0051 mol) of 2-methoximιno-2- [2- (2-methylphenoxymethyl) phenyl] thioacetamide and 1.5 g (0.0076 mol) of bromoacetaldehyde diethylacetal in 50 ml of ethanol are heated under reflux. After 18 hours a further gram of bromoacetaldehyde diethylacetal and 1 ml of glacial acetic acid are added and the mixture is heated under reflux for a further 5 hours. The mixture is concentrated and the residue is taken up in dichloromethane, first with sodium bicarbonate solution, then with water. The organic phase is separated off, dried over sodium sulfate and concentrated. The residue is chromatographed on 100 g of silica gel using cyclohexane / ethyl acetate (3 l). 1.01 g (59% of theory) of 2- {methoxιmιno- [2- (2 - methylphenoxymethyl) phenyl] methyl} thiazole
'H-NMR (CDC1 ,/TMS) δ = 2.16 (s 3H), 4,01 (s. 3H ). 4.9S ( s 2H ) ppm'H NMR (CDC1, / TMS) δ = 2.16 (s 3H), 4.01 (s. 3H). 4.9S (s 2H) ppm
Analog Beispi el (1- 14). sowie gemäß der allgemeinen Beschreibung des Verfahrens d) erhalt manAnalogous to example (1-14). and according to the general description of method d), one obtains
Beispiel (1-15): 4.5-Dihydro-2- { methoximino-[2-(2-methylphenoxymethyl)- phenyl]-methyl }-thιazol. vom Schmelzpunkt 82°C,Example (1-15): 4.5-Dihydro-2- {methoximino- [2- (2-methylphenoxymethyl) phenyl] methyl} thιazole. melting point 82 ° C,
Beispiel (1-16): 4-Ethoxy-2-{ methoxιmιno-[2-(2-methylphenoxymethyl)-phe-nyl]- methyl Xthiazol, vom Schmelzpunkt 65°C,Example (1-16): 4-ethoxy-2- {methoxιmιno- [2- (2-methylphenoxymethyl) -phenyl] methyl xthiazole, melting point 65 ° C.,
Beispiel (1-17): 4-Ethoxy-5-methyl-2-{methoximιno-[2-(2-methylphenoxymethyl)- phen\ ]-methyl }-thιazol. vom Schmelzpunkt 71 °C,
Beispiel (1-18): 4-Methyl-2-{methoximino-[2-(2-methylphenoxymethyl)-phenyl]- methyl j-thiazol, vom Schmelzpunkt 99°C,Example (1-17): 4-ethoxy-5-methyl-2- {methoximιno- [2- (2-methylphenoxymethyl) phen \] methyl} thιazole. melting point 71 ° C, Example (1-18): 4-methyl-2- {methoximino- [2- (2-methylphenoxymethyl) phenyl] methyl j-thiazole, melting point 99 ° C.,
Beispiel (1-19): 5-Ethoxycarbonylmethyliden-4-oxo-2-{methoximino-[2-(2-methyl- phenoxymethyl)-phenyl]-methyl }-thiazol, 1H-NMR (CDC1-./TMS) δ = 2,24, 2,25, 3,82, 3,86, 6,53, 6,58 ppm
Example (1-19): 5-ethoxycarbonylmethylidene-4-oxo-2- {methoximino- [2- (2-methylphenoxymethyl) phenyl] methyl} thiazole, 1H-NMR (CDC1-./TMS) δ = 2.24, 2.25, 3.82, 3.86, 6.53, 6.58 ppm
Beispiel AExample A
Plas opara-Test (Reben) / protektivPlas opara test (vines) / protective
Losungsmittel 4,7 Gewichtsteile AcetonSolvent 4.7 parts by weight of acetone
Emulgator. 0,3 Gewichtsteile AlkylarylpolyglykoletherEmulsifier. 0.3 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Ge¬ wichtsteil Wirkstoff mit den angegebenen Mengen Losungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte KonzentrationTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoff¬ zubereitung besprüht Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wäßrigen Sporensuspension von Plasmopara viticola inokuliert und verblei¬ ben dann 1 Tag in einer Feuchtkammer bei 20 bis 22°C und 100% relativer Luft¬ feuchtigkeit Anschließend werden die Pflanzen 5 Tage im Gewachshaus bei 21°C und ca 90% Luftfeuchtigkeit aufgestellt Die Pflanzen werden dann angefeuchtet und 1 Tag in eine Feuchtkammer gestelltTo test for protective activity, young plants are sprayed with the active compound preparation. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a moist chamber at 20 to 22 ° C. and 100% relative air for 1 day ¬ moisture Then the plants are placed in a greenhouse at 21 ° C and approx. 90% humidity for 5 days. The plants are then moistened and placed in a humid chamber for 1 day
6 Tage nach der Inokulation erfolgt die AuswertungEvaluation is carried out 6 days after the inoculation
Bei diesem Test zeigen z B die folgenden Verbindungen (1-7) und (1-8) bei einer Wirkstoffkonzentration von 100 ppm einen Wirkungsgrad von 71 bis 88 %
In this test, for example, the following compounds (1-7) and (1-8) show an efficiency of 71 to 88% at an active substance concentration of 100 ppm
109a109a
Tabelle ATable A
Plasmopara-Test (Rebe) / Protektiv Wirkstoff Wirkungsgrad in % der unbehandelten Kontrolle bei einer Wirkstoffkonzentration von 100 ppmPlasmopara test (vine) / protective active ingredient Efficiency in% of the untreated control at an active ingredient concentration of 100 ppm
(erfindungsgemaß) (1-7)(according to the invention) (1-7)
(erfindungsgemaß) (1-8)
(according to the invention) (1-8)
- 1 10 -- 1 10 -
Beispiel BExample B
Erysiphe-Test (Gerste) / protektivErysiphe test (barley) / protective
Losungsmittel 10 Gewichtsteile N-Methyl-pyrrolidonSolvent 10 parts by weight of N-methyl-pyrrolidone
Emulgator 0,6 Gewichtsteile AlkylarylpolyglykoletherEmulsifier 0.6 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1To produce a suitable preparation of active compound, mix 1
Gewichtsteil Wirkstoff mit den angegebenen Mengen Losungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte KonzentrationPart by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration
Zur Prüfung auf protektive Wirksamkeit besprüht man junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge Nach Antrocknen desTo test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate after the
Spritzbelages werden die Pflanzen mit Sporen von Erysψhe gra ims f.sp.hordei bestaubtThe plants are sprinkled with Erysψhe gra ims f.sp.hordei spores
Die Pflanzen werden in einem Gewachshaus bei einer Temperatur von ca 20°C und einer relativen Luftfeuchtigkeit von ca 80 % aufgestellt, um die Entwicklung von Mehltaupusteln zu begünstigenThe plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative air humidity of approx. 80% in order to promote the development of mildew pustules
7 Tage nach der Inokulation erfolgt die AuswertungEvaluation is carried out 7 days after the inoculation
Bei diesem Test zeigt z B die folgende Verbindunge (1-6) bei einer Wirkstoff¬ aufwandmenge von 125 g/ha einen Wirkungsgrad von 88 %
In this test, the following compounds (1-6), for example, show an efficiency of 88% with an active ingredient application rate of 125 g / ha
10a10a
Tabelle :BTable: B
Erysiphe-Test (Gerste) / protektiv Wirkstoff Wirkungsgrad in % der unbehandelten Kontrolle bei einer Wirkstoffaufwand¬ menge von 125 g/haErysiphe test (barley) / protective active ingredient Efficiency in% of the untreated control with an active ingredient application rate of 125 g / ha
(erfindungsgemäß) (1-6)
(according to the invention) (1-6)
- 1 1 1 -- 1 1 1 -
Beispiel CExample C
Pyricularia-Test (Reis) / protektivPyricularia test (rice) / protective
Lösungsmittel 12,5 Gewichtsteile AcetonSolvent 12.5 parts by weight of acetone
Emulgator 0,3 Gewichtsteile AlkylarylpolyglykoletherEmulsifier 0.3 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1To produce a suitable preparation of active compound, mix 1
Gewichtsteil Wirkstoff mit den angegebenen Mengen Losungsmittel und verdünnt das Konzentrat mit Wasser und der angegebenen Menge Emulgator auf die gewünschte KonzentrationPart by weight of active ingredient with the stated amounts of solvent and dilutes the concentrate to the desired concentration with water and the stated amount of emulsifier
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Reispflanzen mit der Wirkstoffzubereitung bis zur Tropfnasse 4 Tage nach dem Abtrocknen desTo test for protective activity, young rice plants are sprayed with the preparation of active compound until dripping wet 4 days after the
Spritzbelages werden die Pflanzen mit einer wäßrigen Sporensuspension von Pyricularia oryzae inokuliert Anschließend werden die Pflanzen in einem Gewachshaus bei 100% rel Luftfeuchtigkeit und 25°C aufgestelltThe plants are sprayed with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative atmospheric humidity and 25 ° C.
4 Tage nach der Inokulation erfolgt die Auswertung des KrankheitsbefallsThe disease infestation is evaluated 4 days after the inoculation
Bei diesem Test zeigt z.B die folgende Verbindung (1-3) bei einer Wirkstoff¬ konzentration von 0,05 % einen Wirkungsgrad von 100 %
In this test, for example, the following compound (1-3) shows an efficiency of 100% at an active ingredient concentration of 0.05%
- l i l a- l i l a
Tabelle :CTable: C
Pyricularia-Test (Reis) / protektiv Wirkstoff Wirkstoff- Wirkungsgrad in % konzentration der unbehandelten in % KontrollePyricularia test (rice) / protective agent Active ingredient Efficiency in% concentration of the untreated in% control
(erfindungsgemaß) (1-3)
(according to the invention) (1-3)
Claims
- 1 12 -- 1 12 -
PatentansprücheClaims
1 Verbindungen der allgemeinen Formel (I),1 compounds of the general formula (I),
Z-G-Ar- E- R Z -G- Ar - E- R
(l) in welcher(l) in which
Ar für gegebenenfalls substituiertes Arylen oder Heteroarylen steht,Ar represents optionally substituted arylene or heteroarylene,
E für eine 1 -Alken- 1, 1-dιyl-Gruppιerung steht, die in 2-Position einenE stands for a 1-alkene-1, 1-dιyl grouping in the 2-position
Rest R1 enthalt, oder für eine 2-Aza-l-alken-l , l -diyl-Gruppιerung steht, die in 2-Position einen Rest R" enthalt, oder für eine gegebenenfalls substituierte Imino-Gruppierung ("AzamethylenX N- R ) steht, oder für eine 3-Aza-l-propen-2,3-diyl-Gruppierung steht, die in 1 -Position einen Rest R1 und in 3-Position einen Rest R enthält, oder für eine 3-Oza-l -propen-2,3-diyl-Gruppierung steht, die in 1 -Position einen Rest R enthält, oder für eine 3-Thia- l -propen- 2,3-diyl-Gruppierung steht, die in 1 -Position einen Rest R1 enthalt, oder für eine l-Aza-l-propen-2,3-dιyl-Gruppierung steht, die in 1-Radical R 1 contains, or stands for a 2-aza-l-alkene-l, l -diyl grouping which contains a radical R "in the 2-position, or for an optionally substituted imino grouping (" AzamethylenX N-R ) stands for, or stands for a 3-aza-l-propene-2,3-diyl grouping which contains a radical R 1 in the 1 position and a radical R in the 3 position, or for a 3-oza-l -propene-2,3-diyl grouping which contains a radical R in the 1 position, or a 3-thiol-propene-2,3-diyl grouping which has a radical R in the 1 position 1 contains, or stands for an l-aza-l-propene-2,3-dimyl grouping, which in 1-
Position einen Rest R~ und in 3-Positιon einen Rest RΛ enthalt, oder für eine l -Aza-l -propen-2,3-dιyl-Gruppιerung steht, die in 1 - Position einen Rest R1 und in 3-Posιtιon einen Rest R' enthalt, oder für eine l ,3-Dιaza-l -propen-2,3-dιyl-Gruppιerung steht, die in 1 - Position einen Rest R" und in 3-Posιtιon einen Rest R" enthalt, oder für eine l -Aza-3-oxa-l -propen-2,3-diyl-Gruppierung steht, die in 1 - Position einen Rest R~ enthalt, oder für eine l -Aza-3-thia- l-propen- 2.3-dιyl-Gruppιerung steht, die in 1 -Position einen Rest R" enthalt, wobeiPosition contains a radical R ~ and in 3-position a radical R Λ , or stands for an l -aza-l-propene-2,3-dimyl grouping which in position 1 contains a radical R 1 and in 3-position contains a radical R ', or stands for a 1,3-daza-l-propene-2,3-dimyl grouping which contains a radical R "in the 1 position and a radical R" in the 3 position, or for there is an 1-aza-3-oxa-1-propene-2,3-diyl group which contains a radical R ~ in the 1-position, or for an 1-aza-3-thia-1-propene 2.3- stands for dιyl grouping, which contains a radical R "in the 1 position, where
R1 für Wasserstoff. Hal ogen, Cyano oder für j ewei l s gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio. Alkylamino oder Dialkylamino steht,
R2 für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylamino oder Dialkylamino steht, undR 1 for hydrogen. Hal ogen, cyano or optionally substituted alkyl, alkoxy, alkylthio. Alkylamino or dialkylamino, R 2 represents hydrogen, amino, hydroxy, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R3 für Wasserstoff, Cyano, Hydroxy oder für j eweil s gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl,R 3 represents hydrogen, cyano, hydroxyl or optionally substituted alkyl, alkoxy, alkoxyalkyl,
Alkenyl, Alkinyl, Cycloalkyl oder Cycloalkylalkyl steht,Alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
für eine Einfachbindung, für Sauerstoff, Schwefel oder für jeweils gegebenenfalls durch Halogen, Hydroxy, Alkyl, Halogenalkyl oder Cycloalkyl substituiertes Alkandiyl, Alkendiyl, Alkindiyl oder eine der nachstehenden Gruppierungenfor a single bond, for oxygen, sulfur or for alkanediyl, alkenediyl, alkynediyl or one of the following groups, each optionally substituted by halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl
-Q-CQ-, -CQ-Q-, -CH,-Q-, -Q-CH,-, -CQ-Q-CH,-, -CH,-Q-CQ-, -Q-CQ-CH,-, -Q-CQ-Q-CH,-, -N=N-, -S(O) -, -CH,-S(O), , -CQ-, -S(O)n-CH,-, -C(R4)=N-O-, -C(R )=N-O-CH,-, -N(R5)-. -C-N(R5)-, -N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH,-, -CH,-O-N=C(R4)-,-Q-CQ-, -CQ-Q-, -CH, -Q-, -Q-CH, -, -CQ-Q-CH, -, -CH, -Q-CQ-, -Q-CQ-CH , -, -Q-CQ-Q-CH, -, -N = N-, -S (O) -, -CH, -S (O),, -CQ-, -S (O) n -CH, -, -C (R 4 ) = NO-, -C (R) = NO-CH, -, -N (R 5 ) -. -CN (R 5 ) -, -N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH, -, -CH, -ON = C (R 4 ) -,
-N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH,-, -Q-C(R4)=N-O-CH,-, -N(R5)-C(R4)=N-O-CH,-, -O-CH,-C(R4)=N- O-CH,-, -N=N-C(R4)=N-O-CH,-, -T-ArX oder -T-Ar'-Q- steht, wobei-N (R 5 ) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH, -, -QC (R 4 ) = NO- CH, -, -N (R 5 ) -C (R 4 ) = NO-CH, -, -O-CH, -C (R 4 ) = N- O-CH, -, -N = NC (R 4 ) = NO-CH, -, -T-ArX or -T-Ar'-Q-, where
Ar' für gegebenenfalls substituiertes Arvlen. Heteroaryl en.Ar 'for optionally substituted arvlen. Heteroaryls.
Cycloalkylen oder Heterocycloalkylen ( d h ein zweifach verknüpfter aliphatischer Ring, in dem ein oder mehrere Kohlenstoffatome durch Heteroatome, d h von Kohlenstoff verschiedene Atome ersetzt sind ) steht.Cycloalkylene or heterocycloalkylene (that is a doubly linked aliphatic ring in which one or more carbon atoms are replaced by heteroatoms, that is to say atoms other than carbon).
n für die Zahlen 0. 1 oder 2 steht.n stands for the numbers 0. 1 or 2.
Q für Sauerstoff oder Schwefel steht.Q represents oxygen or sulfur.
R4 fürWasserstoff, Cyano oder jeweils gegebenenfalls substitu¬ iertes Alkyl, Alkoxy. Alkylthio, Alkylamino, Dialkylamino oder Cvcloalkvl steht, und
- 1 14 -R 4 for hydrogen, cyano or in each case optionally substituted alkyl, alkoxy. Alkylthio, alkylamino, dialkylamino or Cvcloalkvl stands, and - 1 14 -
R5 für Wasserstoff, Hydroxy, Cyano oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy oder Cycloalkyl steht undR 5 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH,-O-,T for a single bond, for oxygen, sulfur, -CH, -O-,
CH2-S- oder für gegebenenfalls substituiertes Alkandiyl steht undCH 2 -S- or represents optionally substituted alkanediyl and
R für jeweil s über ein Kohlenstoffatom gebundenes, jeweil s gegebenenfalls an einem Stickstoffatom alkylsubstituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom,
für j eweils über ein Kohlenstoffatom gebundenes, j ewei l s gegebenenfalls substituiertes 1,2,5-Oxadιazolyl, Furyl. Thienyl, 1 ,2-for 1,2,5-oxadiazolyl, furyl, which is bonded in each case via a carbon atom and is optionally substituted. Thienyl, 1, 2-
Thiazolyl, 1 ,3-Thiazolyl, 4-Oxo-l ,3-thiazol-2-yl, 1 ,2,3-Thiadιazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1 ,3,4-Thιadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1,2,4-Triazyl, 1 ,3,5- Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,Thiazolyl, 1, 3-thiazolyl, 4-oxo-l, 3-thiazol-2-yl, 1, 2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1, 3, 4-thιadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1,2,4-triazyl, 1, 3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für jeweils gegebenenfalls substituiertes, gesättigtes Heterocyclyl mit mindestens einem Sauerstoff und/oder mindestens einem Schwefelatom,for in each case optionally substituted, saturated heterocyclyl with at least one oxygen and / or at least one sulfur atom,
oder für gegebenenfalls substituiertes l ,3-Dιazacvcloal - l -en-2-vl steht,or represents optionally substituted 1,3-dazacvcloal-1-en-2-vl,
Z für jeweils gegebenenfalls substituiertes Alkyl. Alken\ l Λlkinvl.Z for each optionally substituted alkyl. Alken \ l Λlkinvl.
Cycloalkyl, Aryl oder Heterocyclyl stehtCycloalkyl, aryl or heterocyclyl
Verbindungen der Formel (I) gemäß Anspruch 1 , in welcherCompounds of formula (I) according to claim 1, in which
Ar für jeweils gegebenenfalls substituiertes Phenylen oder Naphthylen. für mono- oder bicyclisches Heteroarylen mit jeweils 5 oder 6 Ring¬ gliedern oder für benzokondensiertes Heteroarvlen mit 5 oder 6 Ringgliedern, von denen jeweils mindestens eines für Sauerstoff, Schwefel oder Stickstoff steht und gegebenenfalls ein oder zwei weitere für Stickstoff stehen, steht, wobei die möglichen Substituen-
- 1 15 -Ar for each optionally substituted phenylene or naphthylene. represents mono- or bicyclic heteroarylene, each with 5 or 6 ring members, or for benzo-fused heteroarlene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substitutes - 1 15 -
ten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindten are preferably selected from the following list
Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carb¬ amoyl, Thiocarbamoyl, jeweils geradkettiges oder verzweigtes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoff atomen, jeweils geradkettiges oder ver¬ zweigtes Alkenyl, Alkenyloxy oder Alkinyloxy mit jeweils 2 bis 6 Kohlenstoff atomen, jeweils geradkettiges oder verzweigtes Halogen¬ alkyl, Halogenalkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen, jeweils gerad¬ kettiges oder verzweigtes Halogenalkenyl oder Halogenalkenvlow mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen, jeweils geradkettiges oder verzweig- tes Alkylamino, Dialkylamino, Alkylcarbonyl, Alkylcarbonyloxy,Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkylene flow in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy,
Alkoxycarbonyl, Alkylsulfonyloxy, Hydroximinoalkyl oder Alkox- iminoalkyl mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen, jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen und/oder geradkettiges oder ver- zweigtes Alkyl mit 1 bis 4 Kohlen Stoff atomen und/oder gerad¬ kettiges oder verzweigtes Halogenalkyl mit 1 bis 4 Kohlenstoff¬ atomen und 1 bis 9 gleichen oder verschiedenen Halogenatomen substituiertes, jeweils zweifach verknüpftes Alkvlen oder Dioxval- kvlen mit leweils 1 bis 6 Kohlenstoffatomen,Alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case double-linked alkylene or dioxvalve with each 1 to 6 carbon atoms,
E für eine der nachstehenden Gruppierungen stehtE represents one of the groupings below
R ' R:" R ' R : "
^C^ ^C^ ^N^ ι\ / X ^ / ιι ιι ι , c c^ C ^ ^ C ^ ^ N ^ ι \ / X ^ / ιι ιι ι, cc
CH . N , . R I I I ICH. N,. R I I I I
•R ^ R- CH . N ^ , • R ^ R- CH. N ^,
•R ^ K • R ^ K
worinwherein
R1 für W asserstoff. Hal ogen, Cyano oder für j ewei l s gegebenenfalls durch Halogen, Cyano oder Cj-Cj-Al o N substituiertes Alkvl,
Alkvlthio Alkvlamino oder
- 1 16 -R 1 for hydrogen. Halogens, cyano or, in each case, alkylene which is optionally substituted by halogen, cyano or C j -C j -Al o N, Alkvlthio Alkvlamino or - 1 16 -
Dialkylamino mit jeweils 1 bis 6 Kohlenstoff atomen in den Alkylresten steht,Dialkylamino each having 1 to 6 carbon atoms in the alkyl radicals,
. ->. ->
R~ für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils gegebenenfalls durch Halogen, Cyano oder C1-C4-Alkoxy substituiertes Alkyl, Alkoxy, Alkylamino oder Dialkylamino mit jeweils 1 bis 6 Kohlen Stoff atomen in den Alkylresten steht,R ~ stands for hydrogen, amino, hydroxy, cyano or for alkyl, alkoxy, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C 1 -C 4 alkoxy, each having 1 to 6 carbon atoms in the alkyl radicals,
R3 für Wasserstoff, Cyano, Hydroxy oder für j eweil s gegebenenfalls durch Halogen oder Cyano substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkenyl oder Alkinyl mit jeweils bis zu 6 Kohlenstoffatomen oder für jeweils gegebenenfalls durch Halogen, Cyano, C]-C4-Alkyl oder C C4-Alkoxy- substituiertes Cycloalkyl oder Cycloalkylalkyl mit 3 bis 6 Kohlenstoffatomen in den Cycloalkylteilen und gegebenenfalls 1 bis 4 Kohlenstoff atomen im Alkylteil steht,R 3 for hydrogen, cyano, hydroxy or for each s optionally substituted by halogen or cyano alkyl, alkoxy, alkoxyalkyl, alkenyl or alkynyl each having up to 6 carbon atoms or for each optionally by halogen, cyano, C ] -C 4 alkyl or CC 4 -alkoxy-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part,
G für eine Einfachbindung, für Sauerstoff, Schwefel oder für jeweils gegebenenfalls durch Halogen, Hydroxy, C, -C4-Alkyl, C,-C4- Halogenalkyl oder C3-C6-Cycloalkyl substituiertes Alkandiyl, Al¬ kendiyl, Alkindiyl mit jeweils bis zu 4 Kohlenstoffatomen oder eine der nachstehenden GruppierungenG for a single bond, for oxygen, sulfur or for alkanediyl, alkylenediyl, alkynediyl optionally substituted by halogen, hydroxy, C, -C 4 alkyl, C, -C 4 haloalkyl or C 3 -C 6 cycloalkyl each up to 4 carbon atoms or one of the groupings below
-Q-CQ-, -CQ-Q-, -CH,-Q-; -Q-CH,-, -CQ-Q-CH,-, -CH,-Q-CQ-, -Q-CQ-CH,-, -Q-CQ-Q-CH,-, -N=N-, -S(O)n-, -CH,-S(O) -, -CQ-, -S(O)n-CH,-, -C(R4)=N-O-, -C(R4)=N-O-CH,-. -N(R . -CQ- N(R5)-, -N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH,-, -CH,-O-N=C(R4)-,-Q-CQ-, -CQ-Q-, -CH, -Q-; -Q-CH, -, -CQ-Q-CH, -, -CH, -Q-CQ-, -Q-CQ-CH, -, -Q-CQ-Q-CH, -, -N = N- , -S (O) n -, -CH, -S (O) -, -CQ-, -S (O) n -CH, -, -C (R 4 ) = NO-, -C (R 4 ) = NO-CH, -. -N (R. -CQ- N (R 5 ) -, -N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH, -, -CH, -ON = C (R 4 ) -,
-N(R5)-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH,-. -Q-C(R4)=N-O-CH,-, -N(R5)-C(R4)=N-O-CH,-. -O-CH,-C(R4)=N- O-CH,-, -N=N-C(R4)=N-O-CH2-, -T-Ar1- oder -T-Ar' -Q- steht, wobei-N (R 5 ) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH, -. -QC (R 4 ) = NO-CH, -, -N (R 5 ) -C (R 4 ) = NO-CH, -. -O-CH, -C (R 4 ) = N- O-CH, -, -N = NC (R 4 ) = NO-CH 2 -, -T-Ar 1 - or -T-Ar '-Q- stands, where
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
Q für Sauerstoff oder Schwefel steht.
- 1 17 -Q represents oxygen or sulfur. - 1 17 -
R4 für Wasserstoff, Cyano, für jeweils gegebenenfalls durchR 4 for hydrogen, cyano, each for optionally by
Halogen, Cyano oder CrC4-Alkoxy substituiertes Alkyl,Halogen, cyano or C r C 4 alkoxy-substituted alkyl,
Alkoxy, Alkylthio, Alkylamino oder Dialkylamino mit jeweils 1 bis 6 Kohlenstoffatomen in den AJkylgruppen oder für jeweils gegebenenfalls durch Halogen, Cyano, Carboxy,Alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for each optionally by halogen, cyano, carboxy,
CrC4-Alkyl oder C1-C4-Alkoxy-carbonyl substituiertes Cycloalkyl mit 3 bis 6 Kohlenstoff atomen steht, undC r C 4 alkyl or C 1 -C 4 alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
R5 für Wasserstoff, Hydroxy, Cyano oder für gegebenenfalls durch Halogen, Cyano oder C^-C4-Alkoxy substituiertes Alkyl mit 1 bis 6 Kohlenstoffatomen oder für gegebenenfalls durch Halogen, Cyano, Carboxy, CrC4-Alky oder C 1 -C4- Alkoxy-carbonyl substituiertes Cycloalkyl mit 3 bis 6 Koh¬ len Stoff atomen steht undR 5 represents hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C 1 -C 4 -alkoxy or represents optionally substituted by halogen, cyano, carboxy, C r C 4 -alky or C 1 - C4-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms and
Ar1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenylen. Naphthylen,Ar 1 for phenylene which is optionally mono- or polysubstituted by identical or different substituents. Naphthylene,
Cycloalkylen oder für Heteroarylen oder Heterocycloalkylen mit 3 bis 7 Ringgliedern, von denen mindestens eines für Sauerstoff, Schwefel oder Stickstoff und gegebenenfalls ein oder zwei weitere für Stickstoff stehen, steht, wobei die möglichen Substituenten vorzugswei se aus der nach¬ stehenden Aufzählung ausgewählt sindCycloalkylene or for heteroarylene or heterocycloalkylene with 3 to 7 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being selected from the list below
Halogen, Cyano, Nitro, Amino. Hydroxv. l ormvl. Carboxy. Carbamoyl, Thiocarbamoyl,Halogen, cyano, nitro, amino. Hydroxv. l ormvl. Carboxy. Carbamoyl, thiocarbamoyl,
jeweils geradkettiges oder verzweigtes Alkyl, Alkoxy, Alkyl- thio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to 6
Kohlenstoffatomen;Carbon atoms;
j eweil s geradkettiges oder verzweigtes Alkenyl oder ' Alkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen,each straight-chain or branched alkenyl or 'alkenyloxy each having 2 to 6 carbon atoms,
j eweil s geradkettiges oder verzweigtes Hal ogenal kyl . Halogenalkoxv, Halogenalkylthio, Halogenalkylsulfinyl oder
- 1 18 -each straight or branched Hal ogenal kyl. Halogenalkoxv, haloalkylthio, haloalkylsulfinyl or - 1 18 -
Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;Haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
jeweils geradkettiges oder verzweigtes Alkylamino, Dialkyl¬ amino, Alkylcarbonyl, Alkylcarbonyloxy, Alkoxycarbonyl, Alkylsulfonyloxy, Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen, sowie;straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, and;
Cycloalkyl mit 3 bis 6 Kohlenstoffatomen undCycloalkyl with 3 to 6 carbon atoms and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH,-O-,T for a single bond, for oxygen, sulfur, -CH, -O-,
CH2-S- oder für Alkandiyl mit 1 bis 3 Kohlenstoffatomen steht,CH 2 -S- or represents alkanediyl having 1 to 3 carbon atoms,
für j eweils über ein Kohlenstoffatom gebundenes, j eweils gegebenenfalls an einem Stickstoffatom durch C l -C4-Alkyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1.2.3-Triazolyl, 1.2.4- Triazolyl, Tetrazolyl,for pyrrolyl, imidazolyl, pyrazolyl, 1.2.3-triazolyl, 1.2.4-triazolyl, tetrazolyl, each of which is bonded via a carbon atom and is optionally substituted on a nitrogen atom by C 1 -C 4 -alkyl,
für j ewei l s über ein Kohlenstoffatom gebundenes, j ewei l s gegebenenfalls durch Alkyl, Alkoxy oder Hydroxy substituiertesfor each one bonded via a carbon atom, each one optionally substituted by alkyl, alkoxy or hydroxy
1 ,2,5-Oxadiazolyl. Furyl, Thienyl, 1,2-Thiazolyl, 1.3-Thiazolyl.1, 2,5-oxadiazolyl. Furyl, thienyl, 1,2-thiazolyl, 1,3-thiazolyl.
1 ,2.3-Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1 ,2,5-Thiadiazolyl. 1 .3,4-1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2,5-thiadiazolyl. 1 .3.4-
Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazy . 1 ,2,3-Triazyl.Thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazy. 1, 2,3-triazyl.
1 ,2,4-Triazyl, 1 ,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,1, 2,4-triazyl, 1, 3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Alkyliden, Arylalkyliden, Alkylcarbonyl¬ alkiden, Arylcarbonylalkyliden oder Alkoxycarbonylalkyliden substituiertes 4-Oxo-l ,3-thiazol-2-yl,
- 1 19 -for 4-oxo-1,3-thiazol-2-yl which is optionally substituted by alkylidene, arylalkylidene, alkylcarbonylalkide, arylcarbonylalkylidene or alkoxycarbonylalkylidene, - 1 19 -
für jeweils gegebenenfalls durch C l -C4-Alkyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei mindestens ein Ringglied für Sauerstoff und/oder Schwefel steht,for saturated heterocyclyl with 3 to 8 ring members optionally substituted by C 1 -C 4 -alkyl, at least one ring member representing oxygen and / or sulfur,
oder für gegebenenfalls durch Cl-C4-Alkyl substituiertes 1 ,3- Diazacycloalk-l -en-2-yl mit 4 bis 7 Ringgliedern steht,or represents 1,3-diazacycloalk-1-en-2-yl with 4 to 7 ring members which is optionally substituted by C 1 -C 4 -alkyl,
für gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Hydroxy, Amino, C,-C4- Alkoxy, Cj-C4-for optionally single or multiple, identical or different by halogen, cyano, hydroxy, amino, C, -C 4 - alkoxy, C j -C 4 -
Alkylthio, C]-C4-Alkylsulfιnyl oder C]-C4-Alkylsulfonyl (welche jeweils gegebenenfalls durch Halogen substituiert sein können) sub- stituiertes Alkyl mit 1 bis 8 Kohlenstoffatomen,Alkylthio, C ] -C 4 -alkylsulfonyl or C ] -C 4 -alkylsulfonyl (which may in each case optionally be substituted by halogen) substituted alkyl having 1 to 8 carbon atoms,
für jeweils gegebenenfalls durch Halogen substituiertes Alkenyl oder Alkinyl mit jeweils bis zu 8 Kohlenstoffatomen,for alkenyl or alkynyl, each optionally substituted by halogen, each having up to 8 carbon atoms,
für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Carboxy, Phenyl (welches ge- gebenenfalls durch Halogen, Cyano, C1-C4-Alkyl, C, -^-Halogen¬ alkyl, C,-C4-Alkoxy oder C,-C -Halogenalkoxy substituiert ist), Cr C4-Alkyl oder C,-C4-Alkoxy-carbonyl substiuiertes Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,for each optionally one or more times, identically or differently, by halogen, cyano, carboxy, phenyl (which, if appropriate, by halogen, cyano, C 1 -C 4 -alkyl, C, - ^ - haloalkyl, C, -C 4 -Alkoxy or C, -C -haloalkoxy is substituted), C r C 4 -alkyl or C, -C 4 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
für leweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl. Naphthyl oder für Heterocyclyl mit 3 bis 7 Ringgliedern, von denen mindestens eines für Sauer¬ stoff, Schwefel oder Stickstoff und gegebenenfalls ein oder zwei weitere für Stickstoff stehen, steht, wobei die möglichen Substituen¬ ten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindfor phenyl which is optionally mono- or polysubstituted by identical or different substituents. Naphthyl or for heterocyclyl with 3 to 7 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being selected from the list below
Halogen. Cvano. Nitro. Amino, Hydroxy, Formvl. Carboxy, Carb¬ amoyl. Thiocarbamoyl,Halogen. Cvano. Nitro. Amino, hydroxy, formvl. Carboxy, carbamoyl. Thiocarbamoyl,
jeweils geradkettiges oder verzweigtes Alkyl. Alkoxy, Alkylthio Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 6 Kohlenstoff- atomen.
- 120 -each straight-chain or branched alkyl. Alkoxy, alkylthio alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon atoms. - 120 -
jeweils geradkettiges oder verzweigtes Alkenyl oder Alkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen;each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogen- alkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkyl - sulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen,each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
jeweils geradkettiges oder verzweigtes Alkylamino, Dialkylamino.each straight-chain or branched alkylamino, dialkylamino.
Alkylcarbonyl, Alkylcarbonyloxy, Alkoxycarbonyl oder Alkyl- sulfonyloxy, mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen;Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy, each having 1 to 6 carbon atoms in the individual alkyl parts;
jeweils gegebenenfalls einfach oder mehrfach, gleich oder ver- schieden durch Halogen und/oder geradkettiges oder verzweigtesin each case optionally single or multiple, identical or different by halogen and / or straight-chain or branched
Alkyl mit 1 bis 4 Kohlenstoffatomen und/oder geradkettiges oder verzweigtes Halogenalkyl mit 1 bis 4 Kohlenstoffatomen und 1 bis 9 gleichen oder verschiedenen Halogenatomen substituiertes, jeweils zweifach verknüpftes Alkylen oder Dioxvalkylen mit leweils 1 bis b Kohlenstoffatomen,Alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted and in each case doubly linked alkylene or dioxvalkylene each having 1 to b carbon atoms,
Cycloalkyl mit 3 bis 6 Kohlenstoffatomen,Cycloalkyl with 3 to 6 carbon atoms,
Heterocyclyl oder Heterocyclyl-methyl mit jeweils 3 bis 7 Ring¬ gliedern, von denen jeweils 1 bis 3 gleiche oder verschiedene Heteroatome sind - insbesondere Stickstoff, Sauerstoff und/oder Schwefel -,Heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -,
oder eine Gruppierung , worin
- 121 -or a group in which - 121 -
A1 für Alkyl mit 1 bis 4 Kohlenstoff atomen oder Cycloalkyl mit 1 bis 6 Kohlenstoffatomen steht undA 1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A2 für gegebenenfalls durch Cyano, C]-C4-Alkoxy, C j -C4-A 2 for optionally by cyano, C ] -C 4 alkoxy, C j -C 4 -
Alkylthio, C1-C4-Alkylamino, C^C^-Dialkylamino, Phenyl,Alkylthio, C 1 -C 4 alkylamino, C ^ C ^ dialkylamino, phenyl,
5 Halogenphenyl, Methylphenyl, Trifuormethylphenvl. oder5 halophenyl, methylphenyl, trifuormethylphenvl. or
Cj-CT-Alkoxyphenyl substituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen, Alkenyl oder Alkinyl mit jeweils 2 bis 4 Kohlen stoff atomen steht.C j -CT-alkoxyphenyl substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl each having 2 to 4 carbon atoms.
3. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher3. Compounds of formula (I) according to claim 1, in which
0 Ar für jeweils gegebenenfalls substituiertes ortho-, meta- oder para-0 Ar for each optionally substituted ortho-, meta- or para-
Phenylen, für Furandiyl, Thiophendiyl, Pyrroldivl, Pvrazoldiyl. Triazoldiyl, Oxazoldiyl, Isoxazoldiyl, Thiazoldiyl, Isothiazoldiyl, Oxadiazoldiyl, Thiadiazoldiyl, Pyridindiyl (insbesondere Pyridin- 2,3-diyl), Pyrimidindiyl, Pyridazindiyl, Pyrazindiyl, 1 ,3,4-Triazindiyl 5 oder 1,2,3-Triazindiyl steht, wobei die möglichen Substituenten ins¬ besondere aus der nachstehenden Aufzählung ausgewählt sindPhenylene, for furandiyl, thiophendiyl, pyrrole divl, pvrazole diyl. Triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, pyridinediyl (especially pyridine-2,3-diyl), pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1, 3,4-triazinediyl, 5 or 1,2,3-diyl, 5 or 1,2,3-diyl the possible substituents being selected in particular from the list below
Fluor, Chlor, Cyano, Methyl, Ethyl. Cyclopropyl, Trifluormethyl. Methoxy, Ethoxy, Methylthio, Methylsulfinvl oder Methylsulfonyl.Fluorine, chlorine, cyano, methyl, ethyl. Cyclopropyl, trifluoromethyl. Methoxy, ethoxy, methylthio, methylsulfine or methylsulfonyl.
E für eine der nachstehenden Gruppierungen stehtE represents one of the groupings below
R ' R ' R ' R '
- -f0. ^ C ιι ^ ^ C || ^ ^ ^ l / N - ^ C / N - C ^- -f0. ^ C ιι ^ ^ C || ^ ^ ^ l / N - ^ C / N - C ^
CH . N , R i : HCH. N, R i: H
•R R- CH . N . • R R- CH. N.
•R ^ R' • R ^ R '
worinwherein
R1 für Wasserstoff. Fluor, Chlor. Brom. Cyano oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methoxy oderR 1 for hydrogen. Fluorine, chlorine. Bromine. Cyano or for each optionally by fluorine, chlorine, cyano, methoxy or
Ethoxy substituiertes Methyl, Ethyl, Propyl, Methoxy.Ethoxy substituted methyl, ethyl, propyl, methoxy.
25 Ethoxy, Methylthio. Ethylthio, Methylamino, Ethylamino oder Dimethylamino steht.
- 122 -25 ethoxy, methylthio. Ethylthio, methylamino, ethylamino or dimethylamino. - 122 -
R2 für Wasserstoff, Amino, Hydroxy, Cyano oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, Methoxy, Ethoxy, Methylamino, Ethylamino oder Dimethylamino steht,R 2 represents hydrogen, amino, hydroxy, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
R3 für Wasserstoff, Cyano oder für jeweils gegebenenfalls durchR 3 for hydrogen, cyano or for each optionally by
Fluor, Chlor oder Cyano, substituiertes Methyl, Ethyl n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy, Ethoxy oder Methoxymethyl, für Allyl oder Propargyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Methyl, Ethyl, n- oder i-Propyl, Methoxy- oder Ethoxy- substituiertes Cyclo¬ propyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropyl- methyl, Cyclobutylmethyl, Cyclopentylmethyl oder Cyclo- hexylmethyl steht,Fluorine, chlorine or cyano, substituted methyl, ethyl n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy or methoxymethyl, for allyl or propargyl or for each optionally by fluorine, chlorine, cyano, methyl, Ethyl, n- or i-propyl, methoxy- or ethoxy-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
G für eine Einfachbindung, für Sauerstoff. Schwefel oder für jeweils gegebenenfalls durch Fluor, Chlor, Brom, Hydroxy. Methyl, Ethyl, n- oder i-Propyl, Trifluormethyl , Cyclopropyl , Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Methylen, Dimethylen (Ethan-l ,2-diyl), Ethen-l,2-diyl, Ethin- 1.2-diyl oder eine der nach¬ stehenden GruppierungenG for a single bond, for oxygen. Sulfur or for each optionally by fluorine, chlorine, bromine, hydroxy. Methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted methylene, dimethylene (ethane-l, 2-diyl), ethene-l, 2-diyl, ethyne-1,2-diyl or one of the following groups
-Q-CQ-, -CQ-Q-, -CH,-Q-, -Q-CH,-. -CQ-Q-CH,- -C1L-Q-CQ--Q-CQ-, -CQ-Q-, -CH, -Q-, -Q-CH, -. -CQ-Q-CH, - -C1L-Q-CQ-
-Q-CQ-CH,-. -O-CQ-0-CH,-, -N=NX -S( O ), -. -Cl X-Sf O ), -. -CQ-.-Q-CQ-CH, -. -O-CQ-0-CH, -, -N = NX -S (O), -. -Cl X-Sf O), -. -CQ-.
-S(O)π-CH,-, -C(R )=N-O-, -C(R4)=N-0-CH:-. -\( R , -CQ--S (O) π -CH, -, -C (R) = NO-, -C (R 4 ) = N-0-CH : -. - \ (R, -CQ-
N(R5)-,N (R 5 ) -,
-N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R4)-Q-CH,-. -CH:-0-N=C(R4)-. -N(R5)-CQ-Q-. -CQ-N(R5)-CQ-Q-, -N(R )-CQ-Q-CH,-,-N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R 4 ) -Q-CH, -. -CH : -0-N = C (R 4 ) -. -N (R 5 ) -CQ-Q-. -CQ-N (R 5 ) -CQ-Q-, -N (R) -CQ-Q-CH, -,
-Q-C(R )=N-O-CH,-. -N(R5)-C(R4)=N-0-CH,-. -0-CH,-C(R4)=N--QC (R) = NO-CH, -. -N (R 5 ) -C (R 4 ) = N-0-CH, -. -0-CH, -C (R 4 ) = N-
O-CH,-,O-CH, -,
-N=N-C(R4)=N-O-CH;-, -T-Ar1- oder -T-Ar'-Q- steht, wobei-N = NC (R 4 ) = NO-CH ; -, -T-Ar 1 - or -T-Ar'-Q-, where
n • für die Zahlen 0, 1 oder 2 steht, • n represents the numbers 0, 1 or 2;
O für Sauerstoff oder Schwefel steht.
- 123 -O stands for oxygen or sulfur. - 123 -
R4 für Wasserstoff, Cyano, für jeweils gegebenenfalls durchR 4 for hydrogen, cyano, each for optionally by
Fluor, Chlor, Cyano, Methoxy oder Ethoxy substituiertesFluorine, chlorine, cyano, methoxy or ethoxy substituted
Methyl, Ethyl, n- oder i-Propyl, n-, i- oder s-Butyl, Methoxy,Methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy,
Ethoxy, Propoxy, Butoxy, Methylthio, Ethylthio, Propylthio. Butylthio, Methylamino, Ethylamino, Propyl ami no,Ethoxy, propoxy, butoxy, methylthio, ethylthio, propylthio. Butylthio, methylamino, ethylamino, propyl ami no,
Dimethylamino oder Diethylamino oder für jeweils ge¬ gebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethyl, n- oder i-Propyl, Methoxycarbonyl oder Ethoxy¬ carbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht, undDimethylamino or diethylamino or for each case optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R3 für Wasserstoff, Hydroxy, Cvano oder für jeweils ge¬ gebenenfalls durch Fluor, Chlor Cyano Methox\ oder Ethoxy substituiertes Methyl, Ethyl, n- oder ι-Prop\ , n-, I- s- oder t-Butyl oder für jeweils gegebenenfalls durch Fluor, Chlor, Cyano, Carboxy, Methyl, Ethvl, n- oder i-Propyl,R 3 for hydrogen, hydroxyl, Cvano or for methyl, ethyl, n- or ι-prop \, n-, I- or t-butyl, or for each, optionally substituted by fluorine, chlorine, cyano methox \ or ethoxy optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl,
Methoxy-carbonyl oder Ethoxv-carbonyl substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht.Methoxy-carbonyl or ethoxv-carbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Ar1 für jeweils gegebenenfalls einfach bis dreifach substituiertes Phenylen, Naphthylen, Furandiyl. Thiophendiyl, Oxazoldι\ l. Isoxazoldiyl, Thiazoldiyl. Isothiazoldiyl 1.2 4-Oxadιazoldι\ lAr 1 for phenylene, naphthylene, furandiyl which is optionally monosubstituted to trisubstituted. Thiophendiyl, Oxazoldι \ l. Isoxazole diyl, thiazole diyl. Isothiazole diyl 1.2 4-Oxadιazoldι \ l
1 ,3 ,4-Ovadιazoldιyl , 1 ,2,4-Thι adι azol dιvl 1 ,3 4-Thι a- di azoldivl , Pvπdindiyl . P\ π m ι dι ndι \ I Pvπ dazι ndι \ 1 Pvrazindiyl 1 ,2,3-Tπazιndι\ 1 1 ,2 4-Tπazιndιy 1. 1 .3.5- Tπazindivl, Oxirandiyl. Oxetandι\ l Tetrahvdrofurandι\ 1 Perhvdropvrandivl oder Pvrrohdindiyl steht wobei die mög¬ lichen Substituenten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sind1, 3, 4-Ovadιazoldιyl, 1, 2,4-Thι adι azol dιvl 1, 3 4-Thι a- di azoldivl, Pvπdindiyl. P \ π m ι dι ndι \ I Pvπ dazι ndι \ 1 Pvrazindiyl 1, 2,3-Tπazιndι \ 1 1, 2 4-Tπazιndιy 1. 1 .3.5- Tπazindivl, Oxirandiyl. Oxetandι \ l Tetrahvdrofurandι \ 1 Perhvdropvrandivl or Pvrrohdindiyl stands where the possible substituents are preferably selected from the following list
Fluor. Chlor Brom, Cyano Nitro A.mιno. Hvdroxv Formvl Carboxy , Carbamovl, Thιocarbamo\ 1, Methyl. Eth\ l n- oder ι-Propvl, n-. i-, s- oder t-Butyl. Methox\ , Ethox\ . n- oder I -Fluorine. Chlorine bromine, cyano nitro A.mιno. Hvdroxv Formvl carboxy, Carbamovl, Thιocarbamo \ 1, methyl. Eth \ l n- or ι-Propvl, n-. i-, s- or t-butyl. Methox \, Ethox \. n- or I -
Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio Meth\ l- sulfinyl, Ethylsulfinyl, Methyl sulfony l oder Ethvlsulfon\ l Trifluormethyl Tπfluorethyl Difluormethoxy, Tπfluor- methoxv, Dιfluorchlormethox\ Tπfluorethoxv, Difluor-
- 124 -Propoxy, methylthio, ethylthio, n- or i-propylthio meth \ l-sulfinyl, ethylsulfinyl, methyl sulfony l or ethvlsulfon \ l trifluoromethyl trifluoromethyl difluoromethoxy, trifluoromethoxv, difluorochloromethox \ trifluoroethoxv, difluoro- - 124 -
methylthio, Difluorchlormethylthio, Tπfluormethylthio Tπfluormethylsulfinyl oder Tπfluormethylsulfonyl, , Acetyl, Propionyl, Acetyloxy, Methoxycarbonyl, Ethoxycarbonyl, Methylsulfonyloxy, Ethyl sulfonyloxy, Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximinomethylmethylthio, difluorochloromethylthio, trifluoromethylthio trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethox
Methoximinoethyl, Ethoximinoethyl oder Cyclopropyl undMethoximinoethyl, ethoximinoethyl or cyclopropyl and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH,-O-, CH,-S-, Methylen, Ethylen oder Propylen steht undT stands for a single bond, for oxygen, sulfur, -CH, -O-, CH, -S-, methylene, ethylene or propylene and
für jeweils über ein Kohlenstoffatom gebundenes j eweils gegebenenfalls an einem Stickstoff atom durch Methvl oder Ethvl substituiertes Pyrrolyl, Imidazolyl, Pvrazoly l 1,2 3-Tπazolyl 1 ,2 4- Tπazolyl, Tetrazolyl,for pyrrolyl, imidazolyl, Pvrazoly l 1,2 3-tπazolyl 1, 2 4-tπazolyl, tetrazolyl, each substituted via a carbon atom and optionally substituted on a nitrogen atom by methvl or ethvl,
für j eweils über ein Kohlenstoffatom gebundenes, j eweils gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1 ,2,5-Oxadιazolyl, Furyl, Thienyl, 1 ,2-Thιazolyl, 1 3-ThιazolyI,for 1, 2,5-oxadιazolyl, furyl, thienyl, 1, 2-thιazolyl, 1 3-thιazolyI, each bonded via a carbon atom and in each case optionally substituted by methyl, methoxy or hydroxyl,
1 ,2,3-Thιadιazolyl, 1 ,2,4-Thιadιazolvl 1 ,2,5-Thιadιazolyl 1 ,3,4- Thiadiazolyl, Pyridyl, Pyrimidyl, Pvrazyl, Pyπdazyl, 1,2,3-Tπazyl 1,2,4-Tπazyl, 1 ,3,5-Tπazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,1, 2,3-thιadιazolyl, 1, 2,4-thιadιazolvl 1, 2,5-thιadιazolyl 1, 3,4-thiadiazolyl, pyridyl, pyrimidyl, pvrazyl, pyπdazyl, 1,2,3-tπazyl 1,2,4 -Tπazyl, 1, 3,5-Tπazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methvliden Ethvliden Benzvhdenfor if necessary by Methvliden Ethvliden Benzvhden
Acet\lmethvlιden Benzoylmethyhden Ethθλycarbonvlmeth\ lιden oder Methoxycarbonvlmethyhden substituiertes 4-Oxo- l 3-thιazol-2- yiAcet \ lmethvlιden benzoylmethyhden Ethθλycarbonvlmeth \ lιden or methoxycarbonvlmethyhden substituted 4-oxol 3-thιazol-2-yi
für )e\veιls gegebenenfalls durch Meth\ l oder Eth\ l substituiertes gesättigtes Heterocvclvl mit 3 bis 8 Ringgliedern wobei ein zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehenfor) saturated heterocyclic compounds with 3 to 8 ring members, optionally substituted by meth or eth, with one or two or three ring members representing oxygen and / or sulfur
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methv l oder Ethy l substitui ertes Imιdazohdι n-2-\ 1 Tetrahydropyπmιdιn-2-\l oder 4 5 6 7-Tetrahvdro-lH-l 3-dιazepιn- 2-\ l steht
- 125 -or for in each case optionally single, double or triple Imιdazohdι n-2- \ 1 Tetrahydropyπmιdιn-2- \ l or 4 5 6 7-Tetrahvdro-lH-l 3-dιazepιn- 2- \ l is substituted by Methv l or Ethyl l - 125 -
Z für gegebenenfalls einfach bis fünffach durch Fluor, Chlor, Brom,Z for optionally up to five times by fluorine, chlorine, bromine,
Cyano, Hydroxy, Amino, Methoxy, Ethoxy, Methylthio, Ethylthio,Cyano, hydroxy, amino, methoxy, ethoxy, methylthio, ethylthio,
Methylsulfinyl, Ethylsulfinyl, Methyl sulfonyl, Ethylsulfonyl (welche jeweils gegebenenfalls durch Fluor und/oder Chlor substituiert sind) substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, I -, s- oder t-Butyl,Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl,
für jeweils gegebenenfalls einfach bis dreifach durch Fluor, Chlor oder Brom substituiertes Allyl, Crotonyl, 1 -Methyl-allyl, Propargyl oder 1 -Methyl-propargyl,for allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methyl-propargyl which are optionally mono- to trisubstituted by fluorine, chlorine or bromine,
für jeweils gegebenenfalls einfach bis sechsfach durch Fluor. Chlor. Brom, Cyano, Carboxy, Phenyl (welches gegebenenfalls durchfor each, if necessary, up to six times by fluorine. Chlorine. Bromine, cyano, carboxy, phenyl (which may be replaced by
Fluor, Chlor, Brom, Cyano, Methyl, Ethvl, n- oder i-Propyl, n-, ι-. s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i - Propoxy, Difluormethoxy oder Trifiuormethoxy substituiert ist), Methyl, Ethyl, n- oder i-Propyl, Methoxy-carbonyl oder Ethoxy- carbonyl substiuiertes Cyclopropyl, Cyclobutyl, Cyclopentyl oderFluorine, chlorine, bromine, cyano, methyl, Ethvl, n- or i-propyl, n-, ι-. s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifiuormethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, Cyclopentyl or
Cyclohexyl,Cyclohexyl,
für jeweils gegebenenfalls einfach bis dreifach substituiertes Phenyl. Naphthyl, Furyl, Thienyl, Oxazolyl . lsoxazoh l , Thiazolyl , Iso- thiazolyl, 1 ,2,4-Oxadιazolyl, 1 ,3,4-Oxadιazolyl 1 .2.4-ThιadιazoK 1 1 ,3.4-Thιadιazolyl, Pyπdinyl, Pvπmidi l Pvπdazinvl. Pvrazinx lfor phenyl which is optionally monosubstituted to trisubstituted. Naphthyl, furyl, thienyl, oxazolyl. lsoxazoh l, thiazolyl, isothiazolyl, 1, 2,4-oxadιazolyl, 1, 3,4-oxadιazolyl 1 .2.4-thιadιazoK 1 1, 3.4-thιadιazolyl, pyπdinyl, Pvπmidi l Pvπdazinvl. Pvrazinx l
1.2,3-Tπazιnyl, 1 ,2,4-Triazιnyl. 1 ,3.5-Tπazιn\ 1 Oxiranyl.
l Tetrahydrofuryl, Perhydropvranvl
l Pi peπdinx l odei Morpholinyl steht, wobei die möglichen Substituenten vorzugsw eise aus der nachstehenden Aufzahlung ausgewählt sind1,2,3-Tπazιnyl, 1, 2,4-triazιnyl. 1, 3.5-Tπazιn \ 1 oxiranyl. l tetrahydrofuryl, perhydropvranvl l Pi peπdinx l odei morpholinyl, the possible substituents preferably being selected from the list below
^ Fluor. Chlor, Brom, Cvano Nitro. λmino, Hvdrox\ , Formyl^ Fluorine. Chlorine, bromine, Cvano Nitro. λmino, Hvdrox \, Formyl
Carboxy , Carbamoyl, Thιocarbamo\ 1 Methy l, Ethy l. n- oder i- Propvl. n-, I-, s- oder t-Buty l. Methow . Ethoxy . n- oder i-Propoxy Methylthio, Ethylthio. n- oder i-Propylthio. Methylsulfinyl. Ethyl¬ sulfinyl , Methy sulfonyl oder Ethylsulfonyl . Trifluormethyl . 0 Tri fluorethyl , Difluormethoxy , Tri fiuormethoxy , Di fluorchl or- methoxy. Trifluorethoxy. Difluormethvlthio. Difluorchlormethylthio. Trifluormethylthio, Trifluormethvl sulfinyl oder Tπfluormethyl- sulfonyl . Methylamino, Ethylami no, n- oder i -Propylami no.
- 126 -Carboxy, carbamoyl, thιocarbamo \ 1 methyl, ethyl l. n- or i- Propvl. n-, I-, s- or t-buty l. Methow. Ethoxy. n- or i-propoxy methylthio, ethylthio. n- or i-propylthio. Methylsulfinyl. Ethyl sulfinyl, methyl sulfonyl or ethyl sulfonyl. Trifluoromethyl. 0 tri fluoroethyl, difluoromethoxy, trifluoromethoxy, di fluorochloromethoxy. Trifluoroethoxy. Difluormethvlthio. Difluorochloromethylthio. Trifluoromethylthio, Trifluormethvl sulfinyl or Tπfluormethylsulfonyl. Methylamino, Ethylami no, n- or i-Propylami no. - 126 -
Dimethylamino, Diethylamino, Acetyl, Propionyl, Acetyloxy, Methoxycarbonyl, Ethoxycarbonyl, Methylsulfonyloxy oder Ethyl¬ sulfonyl oxy,Dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy or ethylsulfonyloxy,
jeweils gegebenenfalls einfach oder mehrfach, gleich oder ver¬ schieden durch Fluor, Chlor, Methyl, Trifluormethyl, Ethyl, n- oder i-Propyl substituiertes, jeweils zweifach verknüpftes Tπmethylen (Propan-l ,3-diyl), Methylendioxy oder Ethylendioxy,each optionally singly or multiply, identically or differently by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case double-linked tπmethylene (propane-l, 3-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl,Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
oder eine Gruppierung
, worinor a grouping , in which
OO
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, I-, s- oder t-Butyl,A 1 for methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl,
Cyclopropyl oder Cyclobutyl steht undCyclopropyl or cyclobutyl stands and
A* für Methyl, Ethyl, n- oder i-Propyl, n-, ι-, s- oder t-Butyl,A * for methyl, ethyl, n- or i-propyl, n-, ι-, s- or t-butyl,
Allyl, Propargyl, But-2-en-l -yl, 2-Methyl-prop- l -en-3-y ,Allyl, propargyl, but-2-en-l -yl, 2-methyl-prop-l -en-3-y,
Cyanmethyl, Methoxymethyl, Ethoxymethyl, Methoxvethyl, Ethoxyethyl, Methylthiomethyl. Ethylthiomethyl, Methvlthio- ethyl, Ethylthioethyl, Dimethylaminomethyl. Dimethylamino- ethyl, Methylaminomethyl. Methvlaminoethy 1 oder Benzy 1 Methvlbenzyl, Chlorbenzyl. Fluorbenzy l Trifluormetln I- benzyl. Benzoy l. Chlorbenzo\ l oder stehtCyanomethyl, methoxymethyl, ethoxymethyl, methoxvethyl, ethoxyethyl, methylthiomethyl. Ethylthiomethyl, methvthioethyl, ethylthioethyl, dimethylaminomethyl. Dimethylaminoethyl, methylaminomethyl. Methvlaminoethy 1 or Benzy 1 Methvlbenzyl, Chlorbenzyl. Fluorobenzyl trifluoromethyl I-benzyl. Benzoy l. Chlorbenzo \ l or stands
Verbindungen der allgemeinen Formel (1 ) gemäß Anspruch 1Compounds of the general formula (1) according to Claim 1
in welcherin which
Ar für ortho-Phenylen. Pyπdιn-2,3-dιyl oder Thιophen-2.3-dιyl steht.Ar for ortho-phenylene. Pyπdιn-2,3-dιyl or Thιophen-2.3-dιyl is.
E für eine der nachstehenden Gruppierungen steht
- 127 -E represents one of the groupings below - 127 -
' C N ' CN
I I II II I II I
CH NCH N
'R ^R2 'R ^ R 2
worinwherein
R und R" jeweils für Methoxy stehen undR and R "each represent methoxy and
R für Wasserstoff, Cyano, Methyl, Ethyl n- oder i-Propyl, Methoxy, Ethoxy oder Methoxymethyl steht,R represents hydrogen, cyano, methyl, ethyl n- or i-propyl, methoxy, ethoxy or methoxymethyl,
für Sauerstoff oder für jeweils gegebenenfalls durch Fluor, Chlor oder Brom substituiertes Dimethylen (Ethan-l ,2-diyl), Ethen- 1 ,2- diyl oder eine der nachstehenden Gruppierungenfor oxygen or for in each case optionally substituted by fluorine, chlorine or bromine, dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or one of the following groups
-Q-CQ-. -CQ-Q-, -CH,-Q-, -Q-CH,-, -CQ-Q-CH,-, -CH,-Q-CQ-, -Q-CQ-CH,-, -Q-CQ-Q-CH,-, -N=N-, -S(O)n-, -CH,-S(O)n-, -CQ-,-Q-CQ-. -CQ-Q-, -CH, -Q-, -Q-CH, -, -CQ-Q-CH, -, -CH, -Q-CQ-, -Q-CQ-CH, -, -Q- CQ-Q-CH, -, -N = N-, -S (O) n -, -CH, -S (O) n -, -CQ-,
-S(O)n-CH,-, -C(R4)=N-O-, -C(R4)=N-O-CH,-, -N(R5)-, -CQ--S (O) n -CH, -, -C (R 4 ) = NO-, -C (R 4 ) = NO-CH, -, -N (R 5 ) -, -CQ-
N(R5)-,N (R 5 ) -,
-N(R5)-CQ-, -Q-CQ-N(R5)-, -N=C(R )-Q-CH,-, -CH,-O-N=C(R4)-,-N (R 5 ) -CQ-, -Q-CQ-N (R 5 ) -, -N = C (R) -Q-CH, -, -CH, -ON = C (R 4 ) -,
-N(R )-CQ-Q-, -CQ-N(R5)-CQ-Q-, -N(R5)-CQ-Q-CH,-, -Q-C(R )=N-O-CH,-, -N(R5)-C(R4)=N-O-CH,-, -O-CH,-C(R )=N--N (R) -CQ-Q-, -CQ-N (R 5 ) -CQ-Q-, -N (R 5 ) -CQ-Q-CH, -, -QC (R) = NO-CH, -, -N (R 5 ) -C (R 4 ) = NO-CH, -, -O-CH, -C (R) = N-
O-CH,-,O-CH, -,
-N=N-C(R4)=N-O-CH;-, -T-Ar1 - oder -T-Ar'-Q- steht, wobei-N = NC (R 4 ) = NO-CH ; -, -T-Ar 1 - or -T-Ar'-Q-, where
n für die Zahlen 0, 1 oder 2 steht.n stands for the numbers 0, 1 or 2.
O für Sauerstoff oder Schwefel steht,O represents oxygen or sulfur,
R4 für Wasserstoff, Cyano. Methyl. Ethyl oder Cyclopropyl steht undR 4 for hydrogen, cyano. Methyl. Stands for ethyl or cyclopropyl and
R^ für Wasserstoff. Methyl. Ethyl oder Cyclopropyl steht.R ^ for hydrogen. Methyl. Ethyl or cyclopropyl is available.
Ar1 für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenylen oder Pyridindiy , für leyveils gegebenenfalls einfach substituiertes Pvrimidindivl.
- 128 -Ar 1 for phenylene or pyridinediye which are optionally monosubstituted to trisubstituted in the same or different ways, for peyrimidinedivl which are optionally monosubstituted. - 128 -
Pyridazindiyl, Pyrazindiyl, 1,2,3-Triazindiyl, 1,2,4-Triazin- diyl oder 1,3,5-Triazindiyl oder für 1,2,4-Thiadiazoldiyl, 1,3,4-Thiadiazoldiyl, 1,2,4-Oxadiazoldiyl, 1,3,4-Oxadiazol- diyl steht, wobei die möglichen Substituenten vorzugsweise aus der nachstehenden Aufzählung ausgewählt sind:Pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or for 1,2,4-thiadiazole diyl, 1,3,4-thiadiazole diyl, 1,2 , 4-oxadiazole diyl, 1,3,4-oxadiazole diyl, where the possible substituents are preferably selected from the list below:
Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl. Cyclopropyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methyl¬ thio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethyl¬ sulfinyl, Methyl sulfonyl oder Ethylsulfonyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifiuormethoxy, Difluor- chlormethoxy, Trifluorethoxy, Difluormethylthio, Trifluor- methylthio, Difluorchlormethylthio, Trifluormethylsulfinyl oder Trifluormethyl sulfonyl undFluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl. Cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoro-chloromethoxy , Difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethyl sulfonyl and
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH,-O-, CH,-S-, Methylen, Ethylen oder Propylen steht undT stands for a single bond, for oxygen, sulfur, -CH, -O-, CH, -S-, methylene, ethylene or propylene and
für j eweils über ein Kohlenstoffatom gebundenes, j eyvei l s gegebenenfalls an einem Stickstoffatom durch Methyl oder Ethyl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1 ,2,3-Triazolyl, 1.2.4- Triazolyl, Tetrazolyl,for pyrrolyl, imidazolyl, pyrazolyl, 1, 2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, which is bonded via a carbon atom and is optionally substituted on a nitrogen atom by methyl or ethyl,
für j eyvei l s über ei n Kohl enstoffatom gebundenes, j eyvei l s gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1 ,2,5-Oxadiazolyl, Furyl, Thienyl. 1.2-Thiazolyl , 1.3-Thiazolyl . 1 ,2.3-Thiadiazolyl, 1 ,2,4-Thιadiazolyl. 1 ,2,5-Thiadiazolyl, 1 .3.4- Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1.2.3-Triazyl. 1 ,2.4-Triazy , 1 ,3.5-Triazyl, partiell oder vollständig hydriertesfor j eyvei l s bonded via a carbon atom, j eyvei l s optionally substituted by methyl, methoxy or hydroxy 1, 2,5-oxadiazolyl, furyl, thienyl. 1,2-thiazolyl, 1,3-thiazolyl. 1, 2,3-thiadiazolyl, 1, 2,4-thιadiazolyl. 1, 2,5-thiadiazolyl, 1 .3.4-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2.3-triazyl. 1,2,4-triazy, 1,3,5-triazyl, partially or fully hydrogenated
Thiazolyl oder Thiazinyl,Thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethvliden, Benzyliden, Acetylmethyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxycarbonylmethyliden substituiertes 4-Oxo- l ,3-thiazol-2- yl.
- 129 -for 4-oxol, 3-thiazol-2-yl optionally substituted by methylidene, ethlidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene. - 129 -
für jeweils gegebenenfalls durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,for saturated heterocyclyl with 3 to 8 ring members optionally substituted by methyl or ethyl, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imidazolidin-2-yl. Tetra- hydropyrimidin-2-yl oder 4,5,6,7-Tetrahydro-lH- l ,3-diazepin-2-yl steht,or for imidazolidin-2-yl which is optionally substituted once, twice or three times by methyl or ethyl. Tetrahydropyrimidin-2-yl or 4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl,
für j eweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, 1 ,2,4-Thiadiazolyl, 1 ,3.4-Thia- diazolyl, 1 ,2,4-Oxadiazolyl, 1,3,4-Oxadiazolyl, Pvridinyl, Pvrimi- dinyl, Pyridazinyl, Pyrazinyl, 1 ,2,3-Triazinyl, 1 ,2.4-Triazιnvl oder 1,3,5-Triazinyl steht, wobei die möglichen Substituenten vorzugs¬ weise aus der nachstehenden Aufzählung ausgewählt sind.for each phenyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, Pvridinyl, Pvrimi- dinyl, pyridazinyl, pyrazinyl, 1, 2,3-triazinyl, 1, 2,4-triazιnvl or 1,3,5-triazinyl, the possible substituents preferably being selected from the list below.
Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl. n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio,Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl. n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,
Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl, Trifluormethyl, Trifluorethyl. Difluormethoxy, Trifiuormethoxy, Difluorchlormethoxy, Trifluor- ethoxy, Difluormethylthio, Trifluormethylthio. Difluorchlor- methylthio, Trifluormethylsulfinyl oder Trifluormethvlsulfonyl.Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl. Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio. Difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl.
Methoxycarbonyl, Ethoxycarbonyl.Methoxycarbonyl, ethoxycarbonyl.
jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpftes Methylendioxy oder Ethylendioxy,each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy,
oder eine Gruppierung , yvoπn
or a grouping, yvoπn
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, i-. s- oder t-Butyl Cyclopropyl oder Cyclobutyl steht und
- 130 -A 1 for methyl, ethyl, n- or i-propyl, n-, i-. s- or t-butyl is cyclopropyl or cyclobutyl and - 130 -
A2 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butvl, Allyl, Propargyl, But-2-en-l -yl, 2-Methyl-prop- l -en-3-yl, Cyanmethyl, Methoxymethyl, Ethoxymethyl, Methoxy ethyl, Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methyl- thioethyl, Ethylthioethyl, Dimethylaminomethyl, Dimethyl- aminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl, Chlorbenzyl, Fluorbenzyl, Trifluor- metylbenzyl, Benzoyl, Chlorbenzoyl oder stehtA 2 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butvl, allyl, propargyl, but-2-en-l -yl, 2-methyl-prop- l -en -3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxy ethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl, trifluoromethyl Chlorbenzoyl or stands
Verbindungen der Formel (I) gemäß Anspruch 1 ,Compounds of the formula (I) according to Claim 1,
in welcherin which
Ar für ortho-Phenylen, Pyridin-2,3-diyl oder Thiophen-2,3-diyl steht.Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl.
E für eine der nachstehenden Gruppierungen steht,E represents one of the groupings below,
^ C^ ^C^ ^^ C ^ ^ C ^ ^
II II I ,II II I,
CH . N„ , RCH. NO
*R R' * RR '
worinwherein
R und R~ jeweils für Methoxy stehen,R and R ~ each represent methoxy,
R1 für Wasserstoff, Methyl oder Ethyl steht,R 1 represents hydrogen, methyl or ethyl,
G für -O-CH, steht undG stands for -O-CH, and
R für j eyveil s über ei n Kohl enstoffatom gebundenes. j eyy ei X gegebenenfalls an einem Stickstoffatom durch Methy l oder Ethvl substituiertes Pyrrolyl, Imidazolyl. Pyrazolyl, 1 ,2,3-Tπazolyl. 1.2.4- Triazolyl, Tetrazolyl,R for j eyveil s bound by a carbon atom. j eyy ei X pyrrolyl, imidazolyl optionally substituted on a nitrogen atom by methyl or ethylene. Pyrazolyl, 1, 2,3-tπazolyl. 1.2.4- triazolyl, tetrazolyl,
für j eweils über ein Kohlenstoffatom gebundenes, j eyvei l s gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertes 1 ,2.5-Oxadiazolyl, Furyl, Thienyl, 1 ,2-Thiazolyl. 1 ,3-Thiazolyl. 1 ,2,3-Thiadiazolyl, 1 ,2.4-Thiadιazolyl, 1 ,2.5-Thiadiazolyl . 1 .3.4-
- 131 -for 1, 2.5-oxadiazolyl, furyl, thienyl, 1, 2-thiazolyl, which is bonded in each case via a carbon atom and is optionally substituted by methyl, methoxy or hydroxyl. 1, 3-thiazolyl. 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2,5-thiadiazolyl. 1 .3.4- - 131 -
Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1,2,3-Triazyl, 1 ,2,4-Triazyl, 1,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,Thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1,2,3-triazyl, 1, 2,4-triazyl, 1,3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyliden, Acetylmethyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxycarbonylmethyliden substituiertes 4-Oxo-l ,3-thiazol-2- yi,for 4-oxo-l, 3-thiazol-2-yi which is optionally substituted by methylidene, ethylidene, benzylidene, acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene,
für jeweils gegebenenfalls einfach oder mehrfach durch Methyl oderfor each optionally one or more times by methyl or
Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bi s 8 Ringgliedern, wobei ein, zwei oder drei Ringglieder für Sauerstoff und/oder Schwefel stehen,Ethyl substituted, saturated heterocyclyl with 3 to 8 ring members, one, two or three ring members representing oxygen and / or sulfur,
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substituiertes Imidazol i din-2-yl , Tetrahydropyrimidin-2-yl oder 4,5,6,7-Tetrahydro- 1 H- 1 ,3-diazepin- 5 2-yl steht,or for imidazole i din-2-yl, tetrahydropyrimidin-2-yl or 4,5,6,7-tetrahydro-1 H- 1,3-diazepine-5 2- optionally substituted once, twice or three times by methyl or ethyl. yl stands,
Z für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl steht, wobei die möglichen Sub¬ stituenten vorzugsweise aus der nachstehenden Aufzählung ausge- yvählt sind.Z represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below.
< ) Fluor. Chlor, Brom, Cyano. Methyl . Ethyl, n- oder i -Propyl , n-, ι -, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio. Ethylthio, n- oder i-Propylthio. Methylsulfinyl. Ethylsulfinyl. Methyl sulfonyl oder Ethylsulfonyl, Trifluormethyl, Difluormethoxy, Trifiuormethoxy. Difluorchlormethoxy. Trifluorethoxy, Difluor- 5 methylthio, Trifluormethylthio, Difluorchlormethylthio. Trifluor- methylsulfinyl oder Trifluormethylsulfony . Methoxycarbonyl . Ethoxycarbonyl,<) Fluorine. Chlorine, bromine, cyano. Methyl. Ethyl, n- or i-propyl, n-, ι -, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio. Ethylthio, n- or i-propylthio. Methylsulfinyl. Ethylsulfinyl. Methyl sulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy. Difluorochloromethoxy. Trifluoroethoxy, difluoro-5-methylthio, trifluoromethylthio, difluorochloromethylthio. Trifluoromethylsulfinyl or Trifluormethylsulfony. Methoxycarbonyl. Ethoxycarbonyl,
jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor. Methyl. Trifluormethyl oder Ethyl substituiertes. (ι jeyveils zweifach verknüpftes Methylendioxy oder Ethylendioxy.
- u ? .each optionally up to four times, identical or different by fluorine, chlorine. Methyl. Trifluoromethyl or ethyl substituted. (ι jeyveils doubly linked methylenedioxy or ethylenedioxy. - u? ,
oder eine Gruppierung || , worinor a grouping || , in which
A. ,NON
OO
A1 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Cyclopropyl oder Cyclobutyl steht undA 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
A2 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Allyl, Propargyl, But-2-en-l-yI. 2-Methyl-prop-l-en-3-yl.A 2 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yI. 2-methyl-prop-l-en-3-yl.
Cyanmethyl, Methoxymethyl, Ethoxymethyl. Methoxy ethyl. Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methylthioethyl, Ethylthioethvl, Dimethylaminomethyl. Dimethvlaminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl, Chlorbenzyl, Fluorbenzyl.Cyanomethyl, methoxymethyl, ethoxymethyl. Methoxy ethyl. Ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethvl, dimethylaminomethyl. Dimethvlaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl.
Trifluormetylbenzyl, Benzoyl, Chlorbenzoyl oder stehtTrifluorometylbenzyl, Benzoyl, Chlorbenzoyl or stands
6. Verbindungen der Formel (I) gemäß Anspruch 1,6. Compounds of formula (I) according to claim 1,
in welcherin which
Ar für ortho-Phenylen, Pyridin-2,3-diyl oder Thiophen-2.3-dιyl steht.Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-dιyl.
E für eine der nachstehenden Gruppierungen steht.E represents one of the groupings below.
^C^ ^c ^^ C ^ ^ c ^
II II I,II II I,
CH , N , R" •R1 ^R' CH, N, R" •R1 ^ R'
yvorinyvorin
R' und R2 jeweils für Methoxy stehen,R 'and R 2 each represent methoxy,
R; für Wasserstoff, Methyl oder Ethyl steht.R ; represents hydrogen, methyl or ethyl.
G für -C(R4)=N-O-CH,- steht, wobeiG represents -C (R 4 ) = NO-CH, -, where
R4 für Wasserstoff. Cyano. Methyl. Ethyl oder Cyclopropyl steht.
- 133 -R 4 for hydrogen. Cyano. Methyl. Ethyl or cyclopropyl is available. - 133 -
R für jeweils über ein Kohlenstoffatom gebundenes, jeweils gegebenenfalls an einem Sückstoffatom durch Methyl oder Ethvl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Tπazolyl, 1,2,4- Tπazolyl, Tetrazolyl,R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, each bonded via a carbon atom and in each case optionally substituted on a nitrogen atom by methyl or ethylene.
für jeweils über ein Kohlenstoffatom gebundenes, jeweils gege¬ benenfalls durch Methyl, Methoxy oder Hydroxv substituiertes 1,25-Oxadιazol>l, Furyl Thienyl, 1,2-Thιazolyl, 1,3-Thιazolvl 1,2,3-Thιadιazolyl, 1,2,4-Thιadιazolyl, 1,2,5-Thιadιazolyl 1,34- Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyπdazvl 1,23-Tπazλl 1,24-Tπazyl 1,35-Tπazyl, partiell oder vollständig hvdπertes Thia¬ zolyl oder Thiazinvlfor 1,25-oxadiazole> l, each of which is bonded via a carbon atom and is optionally substituted by methyl, methoxy or hydroxv, furyl thienyl, 1,2-thιazolyl, 1,3-thιazolvl 1,2,3-thιadιazolyl, 1, 2,4-thιadιazolyl, 1,2,5-thιadιazolyl 1,34-thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyπdazvl 1,23-tπazλl 1,24-tπazyl 1,35-tπazyl, partially or completely hydrogenated thiazole or Thiazinvl
für gegebenenfalls durch Methvliden Ethvliden Benzyliden Acetylmethyliden, Benzoylmeth>hden Ethoxvcarbonylmethy liden oder Methoxycarbonylmethvhden substituiertes 4-Oxo-l 3-thιazol-2- yl,for 4-oxo-l 3-thιazol-2-yl which is optionally substituted by methylene oxide, benzylidene, acetylmethylidene, benzoylmethane, ethoxvcarbonylmethylidene or methoxycarbonylmethylene,
für jeweils gegebenenfalls durch Methvl oder Ethyl substituiertes gesättigtes Heterocvclyl mit 3 bis 8 Ringghedern wobei ein zyvei oder drei Rin 'og;glieder für Sauerstoff und/oder Schyvefel stehenfor in each case optionally substituted by methylene or ethyl, saturated heterocyclic with 3 to 8 ring gethers, one or three ring members representing oxygen and / or schyvefel
oder für |eyveιls gegebenenfalls eintach zyseifach oder dreifach durch Methyl oder Ethyl substituiertes lmιdazolιdιn-2-y 1or for | eyveιls optionally single or triple substituted with methyl or ethyl imidazolid-2-y 1
Tetrahydropy πmιdιn-2-y 1 oder 4567-letrahy dro-1 H-l
2-yl stehtTetrahydropy πmιdιn-2-y 1 or 4567-letrahy dro-1 St. 2-yl stands
Z für leyveils gegebenenfalls einfach bis dreifach gleich oder y erschieden substituiertes Phenyl Pyridyl oder Pyrimidyl steht yyobei die möglichen Substituenten y orzugsyyeise aus der nach¬ stehenden Aufzahlung ausgey\ahlt sindZ represents leyveils phenyl pyridyl or pyrimidyl which is monosubstituted to trisubstituted by the same or y substituents, yy being the possible substituents y are selected from the list below
Fluor Chlor Brom Cyano Methyl Ethyl n- oder i-Propyl n- I- s- oder t-Butyl Methoxy Ethoxy n- oder i-Propoxy MethylthioFluorine chlorine bromine cyano methyl ethyl n- or i-propyl n- I- s- or t-butyl methoxy ethoxy n- or i-propoxy methylthio
Ethylthio n- oder i-Propvlthio Methvlsulfiny 1 Ethvlsulfiny 1 Methvlsulfonyl oder Ethylsulfonyl Trifluormeth l Tπfluorethy 1Ethylthio n- or i-Propvlthio Methvlsulfiny 1 Ethvlsulfiny 1 Methvlsulfonyl or Ethylsulfonyl Trifluormeth l Tπfluorethy 1
Difluormethoxy Trifiuormethoxy Difluorchlormethoxy Tπfluor-
- 134 -Difluoromethoxy Trifiuormethoxy Difluorchlormethoxy Tπfluor- - 134 -
ethoxy, Difiuormethylthio, Trifluormethylthio, Difluorchlormethyl- thio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl, Methoxy¬ carbonyl, Ethoxycarbonyl, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl, Ethoximinoethyl, jeweils gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Methyl, Trifluormethyl oder Ethyl substituiertes, jeweils zweifach verknüpf¬ tes Methylendioxy oder Ethylendioxyethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrachloromethyl, identical or different, fluorine, identical or different, fluorine doubly linked methylenedioxy or ethylenedioxy
7. Verbindungen der Formel (I) gemäß Anspruch 1,7. Compounds of formula (I) according to claim 1,
in welcherin which
Ar für ortho-Phenylen steht,Ar represents ortho-phenylene,
E für eine der nachstehenden Gruppierungen steht,E represents one of the groupings below,
^C^ ^c-" ^^ C ^ ^ c- "^
II II I ,II II I,
CH . N^ , RCH. N ^, R
•R1 ^R2 • R 1 ^ R 2
worinwherein
R' und R2 jeyveils für Methoxy stehen,R 'and R 2 each represent methoxy,
R1 für Wasserstoff, Methyl oder Ethyl steht.R 1 represents hydrogen, methyl or ethyl.
G für -T-Ar'-Q- steht, wobeiG represents -T-Ar'-Q-, where
Q für Sauerstoff oder Schwefel steht,Q represents oxygen or sulfur,
Ar1 für 1 ,2,4-Thiadiazoldiyl, 1 ,3.4-Thiadιazoldιvl, 1.2,4-Oxa- diazoldiyl, 1,3,4-Oxadiazoldiyl oder für jeyveils gegebenen- falls einfach oder zweifach, gleich oder verschieden durchAr 1 for 1, 2,4-thiadiazole diyl, 1, 3,4-thiadiazole divl, 1,2,4-oxadiazole diyl, 1,3,4-oxadiazole diyl or for jeyveil, if necessary, once or twice, identically or differently
Fluor, Chlor, Cyano, Methyl, Cyclopropyl, Methoxy. Methylthio, Trifluormethyl , Difluormethoxy. Trifiuor¬ methoxy, Difluorchlormethoxy substituiertes, Pyridindiyl. Pyrimidindiyl oder 1 ,3,5-Triazindiyl steht.
- 135 -Fluorine, chlorine, cyano, methyl, cyclopropyl, methoxy. Methylthio, trifluoromethyl, difluoromethoxy. Trifiuor¬ methoxy, Difluorchlormethoxy substituted, pyridinediyl. Pyrimidinediyl or 1, 3,5-triazinediyl. - 135 -
T für eine Einfachbindung, für Sauerstoff, Schwefel, -CH,-O-,T for a single bond, for oxygen, sulfur, -CH, -O-,
CH,-S-, Methylen, Ethylen oder Propylen steht undCH, -S-, methylene, ethylene or propylene and
R für jeweils über ein Kohlenstoffatom gebundenes, j eweil s gegebenenfalls an einem Sückstoffatom durch Methyl oder Ethvl substituiertes Pyrrolyl, Imidazolyl, Pyrazolyl, 1,2,3-Triazolyl, 1 ,2.4-R for pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1, 2.4-, each of which is bonded via a carbon atom and is optionally substituted on a nitrogen atom by methyl or ethylene.
Triazolyl, Tetrazolyl,Triazolyl, tetrazolyl,
für j eweil s über ein Kohlenstoffatom gebundenes, j eweil s gegebenenfalls durch Methyl, Methoxy oder Hydroxy substituiertesfor each one bonded via a carbon atom, each one optionally substituted by methyl, methoxy or hydroxy
1 ,2,5-Oxadiazolyl, Furyl, Thienyl, 1 ,2-Thiazolyl, 1 ,3-Thiazolyl. 1 ,2,3-Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1 ,2.5-Thiadiazolyl, 1 ,3.4-1, 2,5-oxadiazolyl, furyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl. 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2,5-thiadiazolyl, 1, 3.4-
Thiadiazolyl, Pyridyl, Pyrimidyl, Pyrazyl, Pyridazyl, 1 ,2,3-Triazyl. 1 ,2,4-Triazyl, 1 ,3,5-Triazyl, partiell oder vollständig hydriertes Thiazolyl oder Thiazinyl,Thiadiazolyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, 1, 2,3-triazyl. 1, 2,4-triazyl, 1, 3,5-triazyl, partially or fully hydrogenated thiazolyl or thiazinyl,
für gegebenenfalls durch Methyliden, Ethyliden, Benzyl iden. Acetylmethyliden, Benzoylmethyliden, Ethoxycarbonylmethyliden oder Methoxycarbonylmethyliden substituiertes 4-Oxo- 1 .3-thiazol-2- yi,for optionally by methylidene, ethylidene, benzyl idene. Acetylmethylidene, benzoylmethylidene, ethoxycarbonylmethylidene or methoxycarbonylmethylidene substituted 4-oxo-1,3-thiazol-2-yi,
für jeyveils gegebenenfalls durch Methyl oder Ethyl substituiertes, gesättigtes Heterocyclyl mit 3 bis 8 Ringgliedern.
ein.
eι oder drei Ringglieder für Sauerstoff und/oder Sςhw ef stehen.for jeyveils, optionally substituted by methyl or ethyl, saturated heterocyclyl with 3 to 8 ring members. on. eι or three ring members stand for oxygen and / or Sςhw ef.
oder für jeweils gegebenenfalls einfach, zweifach oder dreifach durch Methyl oder Ethyl substitui ertes Imi dazol i di n-2-y l Tetrahydropyrimidin-2-yl oder 4,5.6,7-Tetrahydro- 1 H- 1.3-diazepιn- 2-yl steht.or for in each case mono-, di- or trisubstituted by methyl or ethyl imi dazol i di n-2-yl tetrahydropyrimidin-2-yl or 4,5,6,7-tetrahydro-1 H- 1,3-diazepion-2-yl.
Z für jeyveils gegebenenfalls einfach bis dreifach, gleich oder ver¬ schieden durch Fluor. Chlor. Brom. Cyano. Methyl. Ethyl. n- oder I - Propv'l. n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Difluormethoxy, Difiuorchlormethoxy, Trifluor- ethoxv, Trifiuormethoxy oder jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Fluor. Chlor, Methy l.Z for jeyveils optionally up to three times, the same or different by fluorine. Chlorine. Bromine. Cyano. Methyl. Ethyl. n- or I - Propv ' l. n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxv, trifluoromethoxy or in each case optionally single or multiple, identical or different by fluorine. Chlorine, methyl l.
Trifluormethyl oder Ethyl substituiertes, j eyveils zweifach
- 136 -Trifluoromethyl or ethyl substituted, j eyveils twice - 136 -
verknüpftes Methylendioxy oder Ethylendioxy, substituiertes Phenyl, Pyridyl oder Thienyl stehtlinked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl or thienyl
8. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung der Formel (I) nach Anspruch 18. pesticide, characterized by a content of at least one compound of the formula (I) according to claim 1
9 Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) nach Anspruch 1 auf Schädlinge und/oder ihren Lebensraum einwirken läßt9 A method of combating pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat
10 Verwendung von Verbindungen der Formel (I) nach den Ansprüchen 1 bis 7 zur Bekämpfung von Schädlingen10 Use of compounds of formula (I) according to claims 1 to 7 for combating pests
1 1 Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln, dadurch gekennzeichnet, daß man Verbindungen der Formel (I) nach den An¬ sprüchen 1 bis 7 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt1 1 Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claims 1 to 7 are mixed with extenders and / or surface-active agents
12 Verfahren zur Herstellung von Verbindungen der Formel (I) nach Anspruch 1 , dadurch gekennzeichnet, daß man12 A process for the preparation of compounds of formula (I) according to claim 1, characterized in that
a) Ketone der allgemeinen Formel (II)a) ketones of the general formula (II)
.Ar , R.Ar, R
O (II)O (II)
in yvelcherin yvelcher
Ar. G. R und Z die in Anspruch ld angegebenen Bedeutungen habenAr. G. R and Z have the meanings given in claim ld
mit einem Amin der Formel (III),with an amine of the formula (III),
R2-NH2 (III)R 2 -NH2 (III)
in yvelcher
- 137 -in yvelcher - 137 -
R2 die in Anspruch 1 angegebene Bedeutung hat,R 2 has the meaning given in claim 1,
oder einem Säureadditionskomplex davon, gegebenenfalls in Gegen¬ wart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reaktionshilfsmittels, umsetzt,or an acid addition complex thereof, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
oder wenn manor if you
b) Nitrile der allgemeinen Formel (IV)b) nitriles of the general formula (IV)
Z. ^Ar . CN G " Ε.Z. ^ Ar. CN G " Ε.
(IV)(IV)
in welcherin which
Ar, E, G und Z die in Anspruch 1 angegebenen Bedeutungen haben,Ar, E, G and Z have the meanings given in claim 1,
mit einer bifunktionellen Alkylenverbindung der allgemeinen Formel (V),with a bifunctional alkylene compound of the general formula (V),
R -A-R7 (V)R -AR 7 (V)
in yvelcherin yvelcher
A für gegebenenfalls substituiertes Alkylen steht,A represents optionally substituted alkylene,
R'' für Amino oder -SH steht.R '' stands for amino or -SH.
R" für Amino, -COOR oder
steht, wobeiR " for amino, -COOR or stands, where
Rs für Alkyl oder Wasserstoff steht undR s represents alkyl or hydrogen and
R" für Alkyl steht,R "represents alkyl,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gege¬ benenfalls in Gegenyvart eines Reaktionshilfsmittels. umsetzt.
- 138 -optionally in the presence of a diluent and, if appropriate, in the counter-yvart of a reaction auxiliary. implements. - 138 -
oder wenn manor if you
c) Ketone der allgemeinen Formel (II)c) ketones of the general formula (II)
.Ar . R.Ar. R
O D in welcherO D in which
Ar, G, R und Z die oben angegebenen Bedeutungen habenAr, G, R and Z have the meanings given above
mit Phosphorverbindungen der allgemeinen Formel (VI)with phosphorus compounds of the general formula (VI)
(P)— R1 (VI)(P) - R 1 (VI)
in welcherin which
R1 die oben angegebene Bedeutung hat undR 1 has the meaning given above and
(P> für -P(RUV X' oder für -PO(ORn ): steht,(P> stands for -P (R U VX ' or for -PO (OR n ) :
wobeiin which
R, (l für Aryl oder Alkvl steht.R , (l stands for aryl or alkylene.
Rn für Alkyl steht undR n stands for alkyl and
X für Halogen steht,X represents halogen,
gegebenenfalls in Gegenyvart eines Verdünnungsmittels und gege¬ benenfalls in Gegenwart eines Reaktionshilfsmittels, umsetztif appropriate in the countervail of a diluent and, if appropriate, in the presence of a reaction auxiliary
oder wenn manor if you
d) Thioamide der allgemeinen Formel (MI)
- 139 -d) thioamides of the general formula (MI) - 139 -
(VII)(VII)
in welcherin which
Ar, G, E und Z die in Anspruch 1 angegebenen Bedeutungen habenAr, G, E and Z have the meanings given in claim 1
mit Halogenalkylverbindungen der allgemeinen Formel (VIII)with haloalkyl compounds of the general formula (VIII)
1212th
RR
(VIII)(VIII)
X'X '
in yvelcherin yvelcher
R ,12 für Wasserstoff oder Alkyl steht,R, 12 represents hydrogen or alkyl,
X1 für Halogen steht,X 1 represents halogen,
Y1 für Cyano, Alkylcarbonyl. Arylcarbonyl, Formyl. Dialkoxyalkyl oder Alkoxycarbonyl steht.Y 1 for cyano, alkylcarbonyl. Arylcarbonyl, formyl. Dialkoxyalkyl or alkoxycarbonyl.
oder mit Acetylenverbindungen der Formel (IX)or with acetylene compounds of the formula (IX)
Y: Y: (IX)Y : Y : (IX)
in y.elcherin y.elcher
Y" für Alkoxycarbonyl steht undY "stands for alkoxycarbonyl and
YΛ für Wasserstoff, Alkyl, Aryl, Alkylcarbonyl, Arylcarbonyl. oder Alkoxycarbonyl steht,Y Λ for hydrogen, alkyl, aryl, alkylcarbonyl, arylcarbonyl. or alkoxycarbonyl,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gege¬ benenfalls in Gegenwart eines Reaktionshilfsmittels. umsetzt
140if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary. implements 140
13. Verbindungen der Formel (II)13. Compounds of formula (II)
.Ar ^ R.Ar ^ R
O (M)O (M)
in welcher Ar, G, R und Zin which Ar, G, R and Z
die in Anspruch 1 angegebenen Bedeutungen haben.have the meanings given in claim 1.
14 Verbindungen der Formel (Xa)14 compounds of the formula (Xa)
in welcherin which
für -O-CH,-, -C(CH,)=N-0- oder -TX.Ar-O- steht, yvobeistands for -O-CH, -, -C (CH,) = N-0- or -TX.Ar-O-, where
Ar für gegebenenfalls einfach durch Halogen substituierte? Heteroarvlen steht.Ar for halogen which is optionally simply substituted by halogen? Heteroarvlen stands.
T für eine Einfachbindung, für Sauerstoff. Schwefel. -CH,-0-T for a single bond, for oxygen. Sulfur. -CH, -0-
CH,-S- oder für gegebenenfalls substituiertes Alkandivl steht undCH, -S- or represents optionally substituted alkane divl and
Z4 für gegebenenfalls substituiertes Phenyl steht.Z 4 represents optionally substituted phenyl.
R1 " für Wasserstoff oder Alkvl steht.R 1 "represents hydrogen or alkylene.
R1'' für gegebenenfalls durch Cycloalkyl, Hydroxy oder Alkoxy substituiertes Alkyl oder Alkenyl, oder für gegebenenfalls durch Alkyl substituiertes Cycloalkyl oder für Hydroxy oder Alkoxy steht. oder
- 141 -R 1 ″ stands for alkyl or alkenyl optionally substituted by cycloalkyl, hydroxy or alkoxy, or for cycloalkyl optionally substituted by alkyl or for hydroxy or alkoxy. or - 141 -
R13 und R16 gemeinsam mit dem Sückstoffatom, an das sie gebunden sind, für einen gegebenenfalls durch Alkyl substituierten heterocyclischen Ring stehen, der noch ein Sauerstoff- oder Sückstoffatom enthalten, oderR 13 and R 16 together with the nitrogen atom to which they are attached represent an optionally substituted alkyl heterocyclic ring which also contain an oxygen or nitrogen atom, or
G1 für -O-CH,-, -C(CH3)=N-O- oder -T'-Ar-O- steht, wobeiG 1 represents -O-CH, -, -C (CH 3 ) = NO- or -T'-Ar-O-, wherein
Ar für 1 ,2,4-Oxadιazoldiyl, 1 ,3,4-Oxadιazoldιyl, 1 ,2,4-Thιa- diazoldiyl, 1 ,3,4-Thiadiazoldiyl oder für gegebenenfalls einfach durch Halogen substituiertes Pyπmidindivl oder 1 ,3.5-Triazindiyl steht,Ar stands for 1, 2,4-oxadιazoldiyl, 1, 3,4-oxadιazoldιyl, 1, 2,4-thιa- diazole diyl, 1, 3,4-thiadiazole diyl or for pyπmidinedivl or 1,3,5-triazinediyl which is optionally monosubstituted by halogen ,
T1 für eine Einfachbindung, für Sauerstoff Sclnvefel. -CH,-. -T 1 for a single bond, sulfur for oxygen. -CH, -. -
CH,-CH,-, -CH,-O- oder -CH,-S- steht undCH, -CH, -, -CH, -O- or -CH, -S- stands and
Z4 für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, wobei die möglichen Substituen¬ ten vorzugsweise aus der nachstehenden Aufzahlung ausgewählt sindZ 4 for phenyl which may be monosubstituted to trisubstituted identically or differently, the possible substituents preferably being selected from the list below
Fluor, Chlor, Brom, Cyano. Methyl, Ethyl, n- oder i-Propyl, n-. 1-, s- oder t-Butyl, Methoxy, Ethoxy. n- oder i-Propoxy . Methylthio Ethylthio, n- oder i-Propylthio, Methylsulfiny l Ethylsulfiny l Methvlsulfonvl oder Ethylsulfonyl. Trifluormeth l Tπfluorethy 1 Difluormethoxy. Trifiuormethoxy . Difluorchlormethox . Tπfluor- ethoxy . Difluormethylthio, Tπfluormethylthio Difluorchlormethvl- thio, Trifluormethylsulfinyl oder Tπfluormethvlsulfony I. Methoxy ¬ carbonyl. Ethoxycarbonyl,Fluorine, chlorine, bromine, cyano. Methyl, ethyl, n- or i-propyl, n-. 1-, s- or t-butyl, methoxy, ethoxy. n- or i-propoxy. Methylthio Ethylthio, n- or i-Propylthio, Methylsulfiny l Ethylsulfiny l Methvlsulfonvl or ethylsulfonyl. Trifluormeth l Tπfluorethy 1 difluoromethoxy. Trifluoromethoxy. Difluorochloromethox. Tπfluoroethoxy. Difluormethylthio, Tπfluormethylthio Difluorchlormethvl- thio, Trifluormethylsulfinyl or Tπfluormethvlsulfony I. Methoxy ¬ carbonyl. Ethoxycarbonyl,
leyveils gegebenenfalls einfach bis vierfach, gleich odei verschieden durch Fluor. Chlor. Methyl, Trifluormethyl oder Ethyl substituiertes leyveils zyveifach verknüpftes Methylendioxv oder Ethvlendioxy.leyveils optionally up to four times, the same or different due to fluorine. Chlorine. Methyl, trifluoromethyl or ethyl substituted l eyveils zyveiffach linked methylene dioxv or ethylenedioxy.
oder eine Gruppierung 4
, worin
- 142 -or a grouping 4 , in which - 142 -
X für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl. Cyclopropyl oder Cyclobutyl steht undX represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. Cyclopropyl or cyclobutyl stands and
A4 für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl. Allyl, Propargyl, But-2-en- l -yl, 2-MethyI-prop- l -en-3-yl. Cyanmethyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl.A 4 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. Allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl. Cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl.
Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methyl- thioethyl, Ethylthioethyl, Dimethylaminomethyl. Dimethyl- aminoethyl, Methylaminomethyl, Methylaminoethyl oder Benzyl, Methylbenzyl, Chlorbenzyl, Fluorbenzyl. Trifluor- methylbenzyl, Benzoyl, Chlorbenzoyl oder Fluorbenzoyl steht,Ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl. Dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, methylbenzyl, chlorobenzyl, fluorobenzyl. Trifluoromethylbenzyl, benzoyl, chlorobenzoyl or fluorobenzoyl,
R1 "1 für Wasserstoff oder Methyl, Ethyl, n- oder i-Propyl, n-, ι-. s- oder t-Butyl steht,R 1 "1 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, ι-. S- or t-butyl,
R1 für Methyl, Cyclopropylmethyl, Hydroxy, Methoxy, Ethoxy oder für gegebenenfalls durch Carboxy, Hydroxy oder Methoxy substituiertesR 1 for methyl, cyclopropylmethyl, hydroxy, methoxy, ethoxy or for optionally substituted by carboxy, hydroxy or methoxy
Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, 1 -, 2- oder 3-Pentyl. 1 -, 2- oder 3-Hexyl, 1 -, 2-, 3- oder 4-Heptyl, Allyl, oder für gegebe¬ nenfalls durch Methyl substituiertes Cyclopropyl. Cyclobuty l. Cyclopentyl oder Cyclohexyl steht, oderEthyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2- or 3-pentyl. 1 -, 2- or 3-hexyl, 1 -, 2-, 3- or 4-heptyl, allyl, or for cyclopropyl optionally substituted by methyl. Cyclobuty l. Cyclopentyl or cyclohexyl, or
R1 " und R1'' gemeinsam mit dem Stickstoffatom, an das sie gebunden sind einen Pvrrolidin-. Piperidin-, N'-Methylpiperazin- oder Morpholm- ring bildenR 1 " and R 1 " together with the nitrogen atom to which they are attached form a pvrrolidine. Piperidine, N'-methylpiperazine or morphol ring
Verbindungen der Formel (IVa),Compounds of the formula (IVa),
z-G G^ N χ (IVa) z - G G ^ N χ (IVa)
I . R"I. R "
in yvelcherin yvelcher
Ar, G, R und Z die in Anspruch 1 angegebenen Bedeutungen haben
143Ar, G, R and Z have the meanings given in claim 1 143
16. Verbindungen der Formel (XXII),16. Compounds of the formula (XXII),
.Ar . CN " IM (XXII).Ar. CN " IM (XXII)
R" R "
in welcherin which
Ar und R die in Anspruch 1 angegebenen Bedeutungen haben undAr and R have the meanings given in claim 1 and
X" für Halogen steht.
X " stands for halogen.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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DE19504624 | 1995-02-13 | ||
DE19504624 | 1995-02-13 | ||
DE19532345 | 1995-09-04 | ||
DE19532345A DE19532345A1 (en) | 1995-02-13 | 1995-09-04 | Substituted heterocyclic compounds |
PCT/EP1996/000383 WO1996025398A1 (en) | 1995-02-13 | 1996-01-31 | Substituted heterocyclic compounds and their use as fungicides |
Publications (1)
Publication Number | Publication Date |
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EP0809632A1 true EP0809632A1 (en) | 1997-12-03 |
Family
ID=26012370
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP96902952A Withdrawn EP0809632A1 (en) | 1995-02-13 | 1996-01-31 | Substituted heterocyclic compounds and their use as fungicides |
Country Status (5)
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US (1) | US6177459B1 (en) |
EP (1) | EP0809632A1 (en) |
JP (1) | JPH11500716A (en) |
AU (1) | AU4715996A (en) |
WO (1) | WO1996025398A1 (en) |
Families Citing this family (3)
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GB9511694D0 (en) * | 1995-06-09 | 1995-08-02 | Fujisawa Pharmaceutical Co | Benzamide derivatives |
JP4608140B2 (en) * | 2000-07-05 | 2011-01-05 | 石原産業株式会社 | Benzoylpyridine derivatives or salts thereof, fungicides containing them as active ingredients, methods for producing them, and intermediates for producing them |
WO2012083261A1 (en) * | 2010-12-16 | 2012-06-21 | Human Biomolecular Research Institute | Blood brain barrier-penetrating oximes for cholistenerases reactivation |
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GB9320744D0 (en) * | 1992-11-04 | 1993-12-01 | Zeneca Ltd | Oxa and thiadiazole derivatives |
GB9307247D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Fungicidal compounds |
CN1094487C (en) * | 1994-04-01 | 2002-11-20 | 盐野义制药株式会社 | Oxime derivative and bactericide containing the same as active ingredient |
-
1996
- 1996-01-31 AU AU47159/96A patent/AU4715996A/en not_active Abandoned
- 1996-01-31 JP JP8524609A patent/JPH11500716A/en active Pending
- 1996-01-31 WO PCT/EP1996/000383 patent/WO1996025398A1/en not_active Application Discontinuation
- 1996-01-31 EP EP96902952A patent/EP0809632A1/en not_active Withdrawn
- 1996-08-22 US US08/875,818 patent/US6177459B1/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
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See references of WO9625398A1 * |
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US6177459B1 (en) | 2001-01-23 |
JPH11500716A (en) | 1999-01-19 |
WO1996025398A1 (en) | 1996-08-22 |
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