WO1996025398A1 - Substituierte heterocyclische verbindungen und ihre verwendung als fungizide - Google Patents
Substituierte heterocyclische verbindungen und ihre verwendung als fungizide Download PDFInfo
- Publication number
- WO1996025398A1 WO1996025398A1 PCT/EP1996/000383 EP9600383W WO9625398A1 WO 1996025398 A1 WO1996025398 A1 WO 1996025398A1 EP 9600383 W EP9600383 W EP 9600383W WO 9625398 A1 WO9625398 A1 WO 9625398A1
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- WIPO (PCT)
- Prior art keywords
- methyl
- ethyl
- optionally substituted
- cyano
- optionally
- Prior art date
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- 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
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- 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
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- 239000000203 mixture Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
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- 239000007858 starting material Substances 0.000 description 24
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- 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
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 15
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
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- 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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- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 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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- 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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- 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
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- 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
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- 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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- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8524609A JPH11500716A (ja) | 1995-02-13 | 1996-01-31 | 置換複素環式化合物および殺菌・殺カビ剤としてのその使用 |
AU47159/96A AU4715996A (en) | 1995-02-13 | 1996-01-31 | Substituted heterocyclic compounds and their use as fungicides |
EP96902952A EP0809632A1 (de) | 1995-02-13 | 1996-01-31 | Substituierte heterocyclische verbindungen und ihre verwendung als fungizide |
US08/875,818 US6177459B1 (en) | 1995-02-13 | 1996-08-22 | Substituted heterocyclic compounds and their use as fungicides |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19504624.2 | 1995-02-13 | ||
DE19504624 | 1995-02-13 | ||
DE19532345.9 | 1995-09-04 | ||
DE19532345A DE19532345A1 (de) | 1995-02-13 | 1995-09-04 | Substituierte heterocyclische Verbindungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996025398A1 true WO1996025398A1 (de) | 1996-08-22 |
Family
ID=26012370
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/000383 WO1996025398A1 (de) | 1995-02-13 | 1996-01-31 | Substituierte heterocyclische verbindungen und ihre verwendung als fungizide |
Country Status (5)
Country | Link |
---|---|
US (1) | US6177459B1 (de) |
EP (1) | EP0809632A1 (de) |
JP (1) | JPH11500716A (de) |
AU (1) | AU4715996A (de) |
WO (1) | WO1996025398A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9511694D0 (en) * | 1995-06-09 | 1995-08-02 | Fujisawa Pharmaceutical Co | Benzamide derivatives |
JP4608140B2 (ja) * | 2000-07-05 | 2011-01-05 | 石原産業株式会社 | ベンゾイルピリジン誘導体またはその塩、それらを有効成分として含有する殺菌剤、それらの製造方法ならびにそれらを製造するための中間体 |
US9751831B2 (en) * | 2010-12-16 | 2017-09-05 | Human Biomolecular Research Institute | Blood brain barrier-penetrating oximes for cholistenerases reactivation |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994010159A1 (en) * | 1992-11-04 | 1994-05-11 | Zeneca Limited | Oxa- and thiadiazole derivatives used as insecticides and fungicides |
WO1994022844A1 (en) * | 1993-04-07 | 1994-10-13 | Zeneca Limited | Fungicidal oxazolyl and oxadiazolyl derivatives |
WO1995026956A1 (fr) * | 1994-04-01 | 1995-10-12 | Shionogi & Co., Ltd. | Derive d'oxime et bactericide le contenant en tant qu'ingredient actif |
-
1996
- 1996-01-31 AU AU47159/96A patent/AU4715996A/en not_active Abandoned
- 1996-01-31 JP JP8524609A patent/JPH11500716A/ja active Pending
- 1996-01-31 EP EP96902952A patent/EP0809632A1/de not_active Withdrawn
- 1996-01-31 WO PCT/EP1996/000383 patent/WO1996025398A1/de not_active Application Discontinuation
- 1996-08-22 US US08/875,818 patent/US6177459B1/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994010159A1 (en) * | 1992-11-04 | 1994-05-11 | Zeneca Limited | Oxa- and thiadiazole derivatives used as insecticides and fungicides |
WO1994022844A1 (en) * | 1993-04-07 | 1994-10-13 | Zeneca Limited | Fungicidal oxazolyl and oxadiazolyl derivatives |
WO1995026956A1 (fr) * | 1994-04-01 | 1995-10-12 | Shionogi & Co., Ltd. | Derive d'oxime et bactericide le contenant en tant qu'ingredient actif |
Non-Patent Citations (5)
Title |
---|
CHEMICAL ABSTRACTS, vol. 124, no. 11, 11 March 1996, Columbus, Ohio, US; abstract no. 146156f, A. TAKASE ET AL.: "Preparation of oxime-containing heterocyclic compounds as agrochemical fungicides." page 1258; column 2; XP002001849 * |
G.M. BADGER ET AL.: "Polynuclear Heterocyclic Systems. Part VII. Syntheses using the Elbs Reaction.", JOURNAL OF THE CHEMICAL SOCIETY, 1953, LETCHWORTH GB, pages 2774 - 2778, XP002001845 * |
J. V. BRAUN: "Die Einwirkung von Formaldehyd auf sekundäre aromatische Amine.", CHEMISCHE BERICHTE, vol. 41, 1908, WEINHEIM DE, pages 2145 - 2156, XP002001847 * |
M.G. SEELEY ET AL.: "The Structure of the Isomeric Quinoline Dicyanides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 73, no. 2, 15 February 1951 (1951-02-15), DC US, pages 772 - 774, XP002001848 * |
N. MAXIM ET AL.: "L'action des composés organomagnésiens mixtes sur les amides N-disubstituées de l'acide alpha-furancarbonique;", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, vol. 6, 1939, PARIS FR, pages 1339 - 1347, XP002001846 * |
Also Published As
Publication number | Publication date |
---|---|
JPH11500716A (ja) | 1999-01-19 |
EP0809632A1 (de) | 1997-12-03 |
AU4715996A (en) | 1996-09-04 |
US6177459B1 (en) | 2001-01-23 |
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