US20020006958A1 - Substituted aminosalicylic acid amides with fungicidal effect and intermediate products for production thereof - Google Patents
Substituted aminosalicylic acid amides with fungicidal effect and intermediate products for production thereof Download PDFInfo
- Publication number
- US20020006958A1 US20020006958A1 US09/740,450 US74045000A US2002006958A1 US 20020006958 A1 US20020006958 A1 US 20020006958A1 US 74045000 A US74045000 A US 74045000A US 2002006958 A1 US2002006958 A1 US 2002006958A1
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- US
- United States
- Prior art keywords
- carbon atoms
- case
- methyl
- formula
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- DNNHKCJYOXXXOX-UHFFFAOYSA-N 2-aminooxybenzamide Chemical class NOC1=CC=CC=C1C(N)=O DNNHKCJYOXXXOX-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims 10
- 230000000855 fungicidal effect Effects 0.000 title description 2
- 239000013067 intermediate product Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 102
- 239000000543 intermediate Substances 0.000 claims abstract description 4
- -1 cyano- Chemical class 0.000 claims description 437
- 125000004432 carbon atom Chemical group C* 0.000 claims description 172
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 84
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 77
- 239000000460 chlorine Substances 0.000 claims description 75
- 229910052801 chlorine Inorganic materials 0.000 claims description 75
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 69
- 239000011737 fluorine Substances 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 42
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 42
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 42
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 239000001301 oxygen Substances 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 239000005864 Sulphur Chemical group 0.000 claims description 29
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 24
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- DGMIGAHDDPJOPN-UHFFFAOYSA-N 4,6-dichloro-5-fluoropyrimidine Chemical compound FC1=C(Cl)N=CN=C1Cl DGMIGAHDDPJOPN-UHFFFAOYSA-N 0.000 claims description 16
- 125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- 125000001494 2-propynyl group Chemical class [H]C#CC([H])([H])* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000006193 alkinyl group Chemical group 0.000 claims description 12
- UANYAEMYXKVZHS-UHFFFAOYSA-N 2-phenoxypyrimidin-4-amine Chemical class NC1=CC=NC(OC=2C=CC=CC=2)=N1 UANYAEMYXKVZHS-UHFFFAOYSA-N 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
- PRYIHRAZTQDJEP-UHFFFAOYSA-N (2-carbamoylphenyl) nitrate Chemical class NC(=O)C1=CC=CC=C1O[N+]([O-])=O PRYIHRAZTQDJEP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 9
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- XGSFAIWGUAFXSG-UHFFFAOYSA-N 5-fluoro-4-hydroxy-1h-pyrimidin-6-one Chemical compound OC=1N=CNC(=O)C=1F XGSFAIWGUAFXSG-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 125000005842 heteroatom Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- WWWFHFGUOIQNJC-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1O WWWFHFGUOIQNJC-UHFFFAOYSA-N 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 5
- CEJAMBAOKKMZRC-UHFFFAOYSA-N benzyl 2-nitrooxybenzoate Chemical class [O-][N+](=O)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 CEJAMBAOKKMZRC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- SPMFTXFUUJPTKG-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzoyl chloride Chemical compound OC1=C(C(Cl)=O)C=CC=C1[N+]([O-])=O SPMFTXFUUJPTKG-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000010953 base metal Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004520 1,3,4-thiadiazolyl 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
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 22
- 239000000417 fungicide Substances 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- LSBIUXKNVUBKRI-UHFFFAOYSA-N CC1=CC(C)=NC=N1 Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 0 CC(C(OC1(P)P)=*OC1(P)P)=*OP Chemical compound CC(C(OC1(P)P)=*OC1(P)P)=*OP 0.000 description 21
- 239000007858 starting material Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- JTQUWFXGJVFYMM-YRNVUSSQSA-N CO/N=C(\C)C1=NOC(C)(C)C(C)(C)O1 Chemical compound CO/N=C(\C)C1=NOC(C)(C)C(C)(C)O1 JTQUWFXGJVFYMM-YRNVUSSQSA-N 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000370 acceptor Substances 0.000 description 11
- JKJLQBZSWAMMBZ-UHFFFAOYSA-N C.CON=C(C)C Chemical compound C.CON=C(C)C JKJLQBZSWAMMBZ-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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- GRODYPJHIDVMOV-UHFFFAOYSA-N COC1=CC(OC2=CC=CC(C)=C2)=NC=N1 Chemical compound COC1=CC(OC2=CC=CC(C)=C2)=NC=N1 GRODYPJHIDVMOV-UHFFFAOYSA-N 0.000 description 5
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- 238000001816 cooling Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
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- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 229960003811 pyrithione disulfide Drugs 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SRCCECZAEZWOJX-UHFFFAOYSA-M sodium;2-[formyl(hydroxy)amino]propanoate Chemical compound [Na+].[O-]C(=O)C(C)N(O)C=O SRCCECZAEZWOJX-UHFFFAOYSA-M 0.000 description 1
- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-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
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- 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
- A01N43/54—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
- A01N43/72—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
- A01N43/82—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 three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the invention relates to novel substituted aminosalicylamides, to a plurality of processes for their preparation and to their use as fungicides, and also to novel intermediates and to a plurality of processes for their preparation.
- the present invention accordingly, provides the novel substituted aminosalicylamides of tie general formula (I),
- R 1 represents hydrogen, alkyl or alkoxy
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
- Y 2 or Y 3 represents —G—Z
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH 2 —, —CH 2 —Q—CQ—, —Q—CQ—CH 2 —, —Q—CQ—Q—CH 2 —, —S(O) n —, —CH 2 —S(O) n —, —CQ—, —S(O) n —CH 2 —, —C(R 3 ) ⁇ N—O—, —C(R 3 ) ⁇ N—O—CH 2 —, —N(R 4 )—, —CQ—N(R 4 )—, —N(R 4 )—CQ—, —Q—CQ—N(R 4 )—, —N ⁇ C(R 3 )—Q—CH 2 —, —CH 2 —O—N ⁇ C(R 3 )—, —C(CH 3 )-O—CH 2
- Ar 1 represents optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene (i.e. a doubly attached aliphatic ring in which one or more carbon atoms are replaced by heteroatoms, i.e. by atoms different from carbon),
- n represents the numbers 0, 1 or 2
- Q represents oxygen or sulphur
- R 3 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
- R 4 represents hydrogen, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
- R 5 represents hydrogen or alkyl
- T represents a single bond, represents oxygen, sulphur, —CH 2 —O—, —CH 2 —S— or represents optionally substituted alkanediyl,
- Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
- hydrocarbon chains such as alkyl, alkylene, alkenyl or alkinyl
- hydrocarbon chains are in each case straight-chain or branched, including in combination with heteroatoms, such as an alkoxy, alkylthio or alkylamino.
- Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
- Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
- Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds having up to eight ring members in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form, together with further carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
- Cycloalkyl represents saturated carbocyclic cyclic compounds which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
- Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above,
- R 1 is as defined above and
- X 1 represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above,
- the compounds according to the invention and their precursors are present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers or else tautomers.
- stereoisomers such as, for example, E and Z, threo and erythro, and also optical isomers or else tautomers.
- R 1 preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms;
- [0046] in particular represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; preferably hydrogen, methyl or methoxy; particularly preferably hydrogen.
- Y 1 , Y 4 and Y 5 independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms; in particular represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
- Y 2 and Y 3 independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and one of the radicals Y 2 or Y 3 represents the group —G—Z.
- Y 2 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
- Y 3 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably the group —G—Z.
- G preferably represents one of the groupings below
- G represents —C(R 3 ) ⁇ N—O—CH 2 —, where R 3 preferably represents cyclopropyl and in particular methyl.
- G preferably represents —T—Ar 1 —, —T—Ar 1 —S— and in particular —T—Ar 1 —O—, where
- T preferably represents a single bond, represents oxygen, sulphur, —CH 2 —O—, —CH 2 —S— or represents alkanediyl having 1 to 3 carbon atoms, in particular represents a single bond, represents oxygen, sulphur, —CH 2 —O—, —CH 2 —S—, methylene, ethylene or propylene and preferably oxygen.
- Ar 1 preferably represents phenylene, naphthylene, cycloalkylene, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heteroarylene or heterocycloalkylene having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogenoalkyl straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and also
- [0068] represents phenylene or pyridinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, represents in each case optionally monosubstituted pyrimidinediyl, pyridazineidyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, where the possible substituents are preferably selected from the list below:
- Ar 1 preferably
- [0071] represents 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or disubstituted by identical or different substituents, possible substituents being the substituents mentioned above, or particularly preferably represents 1,2,4-thiadiazolediyl or pyrimidinediyl which is optionally mono- or disubstituted by identical or different substituents, possible substituents being those mentioned above, where the substituents preferably represent halogen, in particular fluorine.
- Z preferably represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl and C 1 -C 4 -alkylsulphonyl (each of which may optionally be substituted by halogen);
- [0074] represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms;
- [0075] represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenoalkoxy), C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-carbonyl;
- [0076] represents phenyl, naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogenoalkyl straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- phenyl or phenoxy each of which is mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
- a 1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- a 2 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or
- a 3 represents alkyl having 1 to 4 carbon atoms
- a 4 , A 5 , A 6 and A 7 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- Z in particular represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- [0097] represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- [0098] represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl;
- a 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- a 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethylthioethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
- a 3 represents methyl or ethyl
- a 4 , A 5 , A 6 and A 7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- Z preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano or methoxy;
- [0113] represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- [0114] represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl;
- [0115] and preferably represents phenyl, pyridyl, pyrimidyl or thienyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are as defined above and preferably selected from the list below:
- a 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- a 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
- a 3 represents methyl or ethyl
- a 4 , A 5 , A 6 and A 7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- Z particularly preferably represents pyridyl, pyrimidyl, each of which is optionally mono- to trisubstituted by identical or different substituents, and in particular represents phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents, where the possible substituents are as defined above and preferably selected from the list below:
- the present application preferably provides aminosalicylamides of the formula (I)
- R 1 represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are identical or different and each represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and either
- Y 2 or Y 3 represents —G—Z
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH 2 —, —CH 2 —Q—CQ—, —Q—CQ—CH 2 —, —Q—CQ—Q—CH 2 —, —N ⁇ N—, —S(O) n —, —CH 2 —S(O) n —, —CQ—, —S(O) n —CH 2 —, —C(R 3 ) ⁇ N—O—, —C(R 3 ) ⁇ N—O—CH 2 —, —N(R 4 )—, —CQ—N(R 4 )—, —N(R 4 )—CQ—, —Q—CQ—N(R 4 )—, —N ⁇ C(R 3 )—Q—CH 2 —, —CH 2 —O—N ⁇ C(R 3 )—, —C
- n represents the numbers 0, 1 or 2
- Q represents oxygen or sulphur
- R 3 represents hydrogen, cyano, represents in each case optionally halogen-, cyano- or C 1 -C 1 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups or represents in each case optionally halogen-, cyano-, carboxyl-, C 1 -C 1 -alkyl- or C 1 -C 1 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and
- R 4 represents hydrogen, hydroxyl, cyano or represents optionally halogen-, cyano- or C 1 -C 1 -alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents optionally halogen-, cyano-, carboxyl-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
- R 5 represents hydrogen or alkyl having 1 to 4 carbon atoms
- Ar 1 represents phenylene, naphthylene or cycloalkylene, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heteroarylene or heterocycloalkylene having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below: halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- halogenoalkyl straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and also
- T represents a single bond, represents oxygen, sulphur, —CH 2 —O—, —CH 2 —S— or represents alkanediyl having 1 to 3 carbon atoms,
- Z represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl and C 1 -C 4 -alkylsulphonyl (each of which may optionally be substituted by halogen);
- [0153] represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms;
- [0154] represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenoalkoxy), C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-carbonyl;
- [0155] represents phenyl, naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogenoalkyl straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- phenyl or phenoxy each of which is mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
- a 1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- a 2 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or
- a 3 represents alkyl having 1 to 4 carbon atoms
- a 4 , A 5 , A 6 and A 7 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- R 1 represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy,
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
- Y 2 or Y 3 represents —G—Z
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH 2 —, —CH 2 —Q—CQ—, —Q—CQ—CH 2 —, —Q—CQ—Q—CH 2 —, —N ⁇ N—, —S(O) n —, —CH 2 —S(O) n —, —CQ—, —S(O) n —CH 2 —, —C(R 3 ) ⁇ N—O—, —C(R 3 ) ⁇ N—O—CH 2 —, —N(R 4 )—, —CQ—N(R 4 )—, —N(R 4 )—CQ—, —Q—CQ—N(R 4 )—, —N ⁇ C(R 3 )—Q—CH 2 —, —CH 2 —O—N ⁇ C(R 3 )—, —C
- n represents the numbers 0, 1 or 2
- Q represents oxygen or sulphur
- R 3 represents hydrogen, cyano, methyl, ethyl or cyclopropyl
- R 4 represents hydrogen, methyl, ethyl or cyclopropyl
- R 5 represents hydrogen or methyl
- Ar 1 represents phenylene or pyridinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, represents in each case optionally monosubstituted pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, where the possible substituents are preferably selected from the list below:
- T represents a single bond, represents oxygen, sulphur, —CH 2 —O—, CH 2 —S—, methylene, ethylene or propylene,
- Z represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl or methyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- [0192] represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- [0193] represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; or
- Z represents phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- a 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- a 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
- a 3 represents methyl or ethyl
- a 4 , A 5 , A 6 and A 7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- a very particularly preferred groups of compounds according to the invention are those compounds of the formula (I),
- R 1 represents hydrogen, methyl or methoxy
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
- Y 2 or Y 3 represents —G—Z
- G represents —C(R 3 ) ⁇ N—O—CH 2 —
- R 3 represents methyl or cyclopropyl
- Z represents phenyl, pyridyl or pyrimidyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- R 1 represents hydrogen, methyl or methoxy.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy.
- Y 2 or Y 3 represents —G—Z
- G represents —T—Ar 1 — or —T—Ar 1 —O—
- Ar 1 represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methyl, cyclopropyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,
- T represents a single bond, represents oxygen, sulphur, —CH 2 —O—, CH 2 —S—, methylene, ethylene or propylene.
- Z represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- [0227] represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- [0228] represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl and ethyl; or
- Z represents phenyl, pyridyl, pyrimidyl or thienyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- a 1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- a 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
- a 3 represents methyl or ethyl
- a 4 , A 5 , A 6 and A 7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- radical definitions given in the respective combinations or preferred combinations of radicals individually for this radical are, independently of the respective given combination, replaced by any corresponding radical definition from other preferred ranges.
- the formula (II) provides a general definition of the aminosalicylamides required as starting materials for carrying out the process a) according to the invention.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y 1 , Y 2 , Y 3 , Y 4 and Y 5 .
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above
- a reducing agent such as, for example, hydrogen, iron, zinc, tin-II chloride, sodium hydrogen sulphide or ammonium hydrogen sulphide, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst,
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above
- [0256] are reacted with hydrogen, if appropriate in the presence of a diluent, and if appropriate in the presence of a catalyst.
- the formula (IV) provides a general definition of the nitrosalicylamides required as starting materials for carrying out the process d) according to the invention.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y 1 , Y 2 , Y 3 , Y 4 and Y 5 .
- nitrosalicylamides of the formula (IV) are novel and also form part of the subject matter of the present application.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each as defined above,
- novel nitrosalicylamides of the formula (IV) are suitable for controlling pests on plants and industrial materials, preferably fungi, insects and bacteria.
- the formula (VII) provides a general definition of the amines furthermore required as starting materials for carrying out the process f) according to the invention.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 each preferably or in particular has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y 1 , Y 2 , Y 3 , Y 4 and Y 5 .
- Y 6 , Y 7 , Y 8 , Y 9 and Y 10 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
- Y 7 or Y 8 represents a grouping
- m 0 or 1
- Ar 2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidin-4,6-diyl which is optionally substituted in the 5 position by halogen and
- Z 3 represents optionally substituted aryl.
- Y 6 , Y 7 , Y 8 , Y 9 and Y 10 are identical or different and each represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and either
- Y 7 or Y 8 represents a grouping
- m 0 or 1
- Ar 2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidine-4,6-diyl which is optionally substituted in the 5 position by fluorine or chlorine and
- Z 3 represents phenyl or naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- halogenoalkyl straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- phenyl or phenoxy each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
- a 8 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- a 9 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or
- a 10 represents alkyl having 1 to 4 carbon atoms
- a 11 , A 12 , A 13 and A 14 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- Y 6 , Y 7 , Y 8 , Y 9 and Y 10 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
- Y 7 or Y 8 represents a grouping
- m 0 or 1
- Ar 2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidine-4,6-diyl which is optionally substituted in the 5 position by fluorine or chlorine and
- Z 3 represents phenyl which is in each case optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- a 8 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- a 9 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
- a 10 represents methyl or ethyl
- a 11 , A 12 , A 13 and A 14 are identical or different and, independently of one another, each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- m 0 or 1
- X 2 represents hydrogen, fluorine or chlorine
- X 3 represents chlorine or fluorine
- X 4 represents methylsulphonyl, chlorine or bromine
- Q represents oxygen or sulphur
- Y 11 , Y 12 , Y 13 , Y 14 and Y 15 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
- Y 12 or Y 13 represents amino
- X 2 , Y 11 , Y 12 , Y 13 , Y 14 and Y 15 are each as defined above and
- X 5 represents chlorine or fluorine
- the formula (VIII) provides a general definition of the diazoles required as starting materials for carrying out the process h) according to the invention.
- m and Z 3 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for m and Z 3 .
- X 4 represents methylsulphonyl, chlorine or bromine.
- diazoles of the formula (VIII) are known, and they can be prepared by known methods (compare, for example, DE-A 2142913).
- the formula (IX) provides a general definition of the halogenopyrimidines alternatively required as starting materials for carrying out the process h) according to the invention.
- m and Z 3 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for m and Z 3 .
- X 2 represents hydrogen, fluorine or chlorine.
- X 3 represents fluorine or chlorine.
- halogenopyrimidines of the formula (IX) are known, and they can be prepared by known methods (cf. for example, Pharm.Chem.J.(Engl.Transl.), 23, 6, 1989, 500-503; RU, 23, 6, 1989, 705-707).
- Z 3 is as defined above, except for the compound methyl 2-[(6-chloro-5-fluoro-4-pyrimidinyl)-oxy]- ⁇ -(methoxymethylene)-benzoate.
- the formula (XII) provides a general definition of the phenols required as starting materials for carrying out the process j) according to the invention.
- Z 3 preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for Z 3 .
- the phenols of the formula (XII) are known chemicals for synthesis, or they can be prepared by known processes (WO 95-04728).
- the formula (XI) provides a general definition of the aminophenoxypyrimidines required as starting materials for carrying out the process i) according to the invention.
- Y 11 , Y 12 , Y 13 , Y 14 and Y 15 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the amines of the formula (X) as being preferred or as being particularly preferred for Y 11 , Y 12 , Y 13 , Y 14 and Y 15 .
- X 2 and X 5 independently of one another each represent chlorine or fluorine.
- aminophenoxypyrimidines of the formula (XI) are novel and also form part of the subject matter of the present application.
- X 2 and X 5 are each as defined above and
- X 6 represents fluorine or chlorine
- the formula (XV) provides a general definition of the trihalogenopyrimidines required as starting materials for carrying out the process 1) according to the invention.
- X 2 and X 5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (XI) as being preferred or as being particularly preferred for X 2 and X 5 .
- X 6 represents fluorine or chlorine.
- the formula (V) provides a general definition of the O-benzyl-nitrosalicylamides required as starting materials for carrying out the process e) according to the invention.
- Y 1 , Y 2 , Y 3 , Y 4 and Y 5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y 1 , Y 2 , Y 3 , Y 4 and Y 5 .
- O-benzyl-nitrosalicylamides of the formula (V) have hitherto not been known, as novel substances, they form part of the subject matter of the present application.
- O-benzyl-nitrosalicylamides of the formula (V) are obtained when (process g) O-benzyl-nitrosalicylic acid derivatives of the formula (VI),
- X 7 represents halogen, hydroxyl or alkoxy
- the formula (VI) provides a general definition of the O-benzyl-nitrosalicylic acid derivatives required as starting materials for carrying out the process g) according to the invention.
- X 7 represents halogen, preferably chlorine; hydroxyl or alkoxy, preferably methoxy or ethoxy.
- O-benzyl-nitrosalicylic acid derivatives of the formula (VI) are known, and they can be prepared by known methods (compare, for example, J. Am. Chem. Soc. 1959, 5215-5217).
- the formula (III) provides a general definition for the acylating agents furthermore required as starting materials for carrying out the process a) according to the invention.
- R 1 preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for R 1 .
- X 1 represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy, preferably chlorine, hydroxyl, methoxy, ethoxy or acetoxy.
- acylating agents of the general formula (III) are known reagents in organic chemistry.
- Suitable diluents for carrying out the processes a), f) and g) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxye
- Suitable diluents for carrying out the processes d) and e) according to the invention are all inert organic solvents. These preferably include esters such as methyl acetate or ethyl acetate; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethlylene glycol monomethyl ether, diethylene glycol monoethyl ether, water, salt solutions, such as, for example, ammonium chloride solution, acids, such as, for example, hydrochloric acid or acetic acid, and also any mixtures of the abovementioned diluents.
- esters such as methyl acetate or ethyl acetate
- alcohols such as methanol, ethanol, n- or i-propanol,
- Suitable diluents for carrying out the processes h), i), j) and 1) according to the invention are all inert organic solvents. These preferably include ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; sulphoxides, such as dimethyl sulfoxide; or sulphones, such as sulpholane.
- ethers such as
- Suitable diluents for carrying out the process k) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile.
- aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane,
- Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicyclound
- the processes b), c), d) and e) according to the invention are, if appropriate, carried out in the presence of a catalyst.
- Suitable catalysts are all catalysts which are also usually employed for hydrogenations. Examples include: Raney nickel, palladium or platinum, if appropriate on a support, such as, for example, activated carbon.
- the process c) according to the invention is, if appropriate, also carried out in the presence of hydrogen or, if appropriate, in the presence of a base metal.
- Suitable base metals are, for example: zinc, tin, iron, aluminium or magnesium.
- Suitable further reaction auxiliaries for carrying out the processes a), b) and c) according to the invention are all dehydrating agents, in particular acetic anhydride.
- the processes f) and g) according to the invention are, if appropriate, carried out in the presence of a condensing agent.
- acyl halide formers such as, for example, phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulphonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ)
- Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, alkoxides, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate.
- Suitable catalysts for processes h), i), j) and l) according to the invention are all copper(I) salts, such as, for example, copper(I) chloride, copper(I) bromide or copper(I) iodide, or else fluorides, such as, for example, sodium fluoride, potassium fluoride or ammonium fluoride, and also tertiary ammonium fluorides, such as tetrabutylammonium fluoride.
- copper(I) salts such as, for example, copper(I) chloride, copper(I) bromide or copper(I) iodide
- fluorides such as, for example, sodium fluoride, potassium fluoride or ammonium fluoride, and also tertiary ammonium fluorides, such as tetrabutylammonium fluoride.
- the process k) according to the invention is, if appropriate, carried out in the presence of a suitable catalyst.
- Suitable catalysts are all tertiary amines, such as, for example, trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), and also amides, such as dimethylformamide.
- DABCO diazabicyclooctane
- DBN diazabicyclononene
- DBU diazabicycloundecene
- Suitable halogenating agents for carrying out the process k) according to the invention are all reagents which are capable of exchanging hydroxyl groups which are attached to carbon for chlorine. Examples include: phosgene, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride and, if appropriate, additionally hydrogen chloride or chlorine.
- reaction temperatures can be varied within a relatively wide range.
- the processes are carried out at temperatures from 0° C. to 180° C., preferably at temperatures from 0° C. to 130° C.
- reaction temperatures can be varied within a relatively wide range.
- the processes are carried out at temperatures from ⁇ 20° C. to 200° C., preferably at temperatures from ⁇ 10° C. to 150° C.
- reaction temperatures can be varied within a relatively wide range.
- the process is carried out at temperatures from 0° C. to 250° C., preferably at temperatures from 0° C. to 200° C.
- the compounds according to the invention have potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
- Fungicides are employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
- Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
- Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae;
- Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrymans;
- Erwinia species such as, for example, Erwinia amylovora
- Pythium species such as, for example, Pythium ultimum
- Phytophthora species such as, for example, Phytophthora infestans
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
- Plasmopara species such as, for example, Plasmopara viticola
- Bremia species such as, for example, Bremia lactucae
- Peronospora species such as, for example, Peronospora pisi or P. 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 P. graminea (conidia form: Drechslera, syn: Helminthosporium);
- Cochliobolus species such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);
- Uromyces species such as, for example, Uromyces appendiculatus
- Puccinia species such as, for example, Puccinia recondita
- Sclerotinia species such as, for example, Sclerotinia sclerotiorum
- 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
- Altemaria species such as, for example, Altemaria brassicae;
- Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
- the active compounds according to the invention can be employed particularly successfully for controlling diseases in fruit and vegetable growing and viticulture, such as, for example, against Venturia Phytophthora species. They are also very successfully used for controlling cereal diseases, such as, for example, Pseudocercosporella species, or for controlling rice diseases, such as, for example, Pyricularia species.
- the active compounds according to the invention are also suitable for increasing the harvest yield. Moreover, they show reduced toxicity and are well tolerated by plants.
- the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and micro-encapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
- customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and micro-encapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
- formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam-formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents.
- extenders that is, liquid solvents, liquefied gases under pressure, and/or solid carriers
- surfactants that is emulsifiers and/or dispersants, and/or foam-formers.
- the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents.
- aromatics such as xylene, toluene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, for example 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 sulphoxide, or else water.
- Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide.
- Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates.
- Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
- Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates.
- Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
- Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
- Other suitable additives are mineral and vegetable oils.
- colourants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
- trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
- the active compounds according to the invention can be used as such or in their formulations also mixed with known fungicides, bactericides, acaricides, nematicides or insecticides in order thus, for example, to widen the spectrum of action or to prevent development of resistance. In many cases, synergistic effects are achieved, i.e. the activity of the mixture exceeds the activity of the individual components.
- debacarb dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,
- kasugamycin, kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
- tebuconazole tecloftalam, tecnazene, tetcyclasis, tetraconazole, thiabendazole, thicyofen, thifuzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
- bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloflalam, copper sulphate and other copper preparations.
- Bacillus thuringiensis 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,
- fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron, flucythninate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
- imidacloprid iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,
- parathion A parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenophos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
- vamidothion, XMC, xylylcarb, zetamethrin [0560] vamidothion, XMC, xylylcarb, zetamethrin.
- the active compounds can be used as such or in the form of their commercial formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, spreading, dusting, foaming, brushing-on and the like. It is further possible to apply the by the ultra-low volume method or to inject the preparation of active compound, or the active compound itself, into the soil. The seed of the plants can also be treated.
- the application rates can be varied within a relatively wide range, depending on the type of application.
- the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha.
- the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
- the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
- Emulsifier 3 parts by weight of alkylaryl polyglycol ether
- Emulsifier 3 parts by weight of alkylaryl polyglycol ether
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Abstract
Description
- The invention relates to novel substituted aminosalicylamides, to a plurality of processes for their preparation and to their use as fungicides, and also to novel intermediates and to a plurality of processes for their preparation.
- Certain substituted acylaminosalicylamides, such as, for example, the compounds 3-formamido-salicylanilide 3-(formylamino)-2-hydroxy-N-(phenylmethyl)-benzamide, are already known (compare, for example, Biochim. Biophys. Acta (1993), 1142(3), 262-8, J. Med. Chem. (1990), 33(1), 136-42 or J. Biol. Chem. (1971), 246(23), 7125-30). However, a pesticidal activity of these prior-art compounds has hitherto not been described.
-
- in which
- R1 represents hydrogen, alkyl or alkoxy,
- Y1, Y2, Y3, Y4 and Y5 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
- Y2 or Y3 represents —G—Z,
- in which
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH2—, —CH2—Q—CQ—, —Q—CQ—CH2—, —Q—CQ—Q—CH2—, —S(O)n—, —CH2—S(O)n—, —CQ—, —S(O)n—CH2—, —C(R3)═N—O—, —C(R3)═N—O—CH2—, —N(R4)—, —CQ—N(R4)—, —N(R4)—CQ—, —Q—CQ—N(R4)—, —N═C(R3)—Q—CH2—, —CH2—O—N═C(R3 )—, —C(CH3)-O—N═C(R3 )—, —N(R4)—CQ—Q—, —CQ—N(R4)—CQ—Q—, —N(R4)—CQ—Q—CH2—, —Q—C(R3)═N—O—CH2—, —N(R4)—C(R3)═N—O—CH2—, —O—CH2—C(R3)═N—O—CH2—, —N═N—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)—O—N═CH—, —C(═N—O—R5)—C(R3)—O—N═C(CH3)—, —T—Ar1— or —T—Ar1—Q—,
- where
- Ar1 represents optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene (i.e. a doubly attached aliphatic ring in which one or more carbon atoms are replaced by heteroatoms, i.e. by atoms different from carbon),
- n represents the numbers 0, 1 or 2,
- Q represents oxygen or sulphur,
- R3 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
- R4 represents hydrogen, hydroxyl, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
- R5 represents hydrogen or alkyl and
- T represents a single bond, represents oxygen, sulphur, —CH2—O—, —CH2—S— or represents optionally substituted alkanediyl,
- Z represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.
- In the definitions, the hydrocarbon chains, such as alkyl, alkylene, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as an alkoxy, alkylthio or alkylamino.
- Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
- Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
- Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds having up to eight ring members in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form, together with further carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
- Cycloalkyl represents saturated carbocyclic cyclic compounds which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
- Cycloalkenyl represents carbocyclic cyclic compounds which contain at least one double bond and which form, if appropriate, a polycyclic ring system with other carbocyclic fused-on or bridged rings.
- Furthermore, it has been found that the novel substituted acylaminosalicylamides of the general formula (I) are obtained when
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above,
-
- in which
- R1 is as defined above and
- X1 represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy,
- if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor, and if appropriate in the presence of a further reaction auxiliary, or when
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above
- are reacted with formic acid, if appropriate in the presence of a catalyst and if appropriate in the presence of a further reaction auxiliary, or when
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above,
- are reacted with formic acid, if appropriate in the presence of hydrogen or a base metal, if appropriate in the presence of a catalyst and if appropriate in the presence of a further reaction auxiliary.
- Finally, it has been found that the novel substituted aminosalicylamides of the general formula (I) have very strong fungicidal activity.
- If appropriate, the compounds according to the invention and their precursors are present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers or else tautomers. What is claimed are both the E and the Z isomers, and also the threo and erythro and the optical isomers, and also the possible tautomers, and any mixtures of these isomers.
- In the general formula (I),
- R1 preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms;
- in particular represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; preferably hydrogen, methyl or methoxy; particularly preferably hydrogen.
- In the general formula (I),
- Y1, Y4 and Y5 independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms; in particular represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
- In the general formula (I),
- Y2 and Y3 independently of one another each preferably represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and one of the radicals Y2 or Y3 represents the group —G—Z.
- In particular, Y2 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably hydrogen.
- In particular, Y3 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably the group —G—Z.
- In the general formula (I), G preferably represents one of the groupings below
- —Q—CQ—, —CQ—Q—, —CQ—Q—CH2—, —CH2—Q—CQ—, —Q—CQ—CH2—, —Q—CQ—Q—CH2—, —N═N—, S(O)n—, —CH2—S(O)n—, —CQ—, —S(O)n—, CH2—, —C(R3)═N—O—, —C(R3)═N—O—CH2—, —N(R4)—, —CQ—N(R4)—, —N(R4)—CQ—, —Q—CQ—N(R4)—, —N═C(R3)—Q—CH2—, —CH2—O—N═C(R3)—, —C(CH3)—O—N═C(R3)—, —N(R4)—CQ—Q—, —CQ—N(R4)—CQ—Q—,—N(R4)—CQ—Q—CH2—, —Q—C(R3)═N—O—CH2—, —N(R4)—C(R3)═N—O—CH2—, —O—CH2—C(R3)═N—O—CH2—, —N═N—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)—O—N═CH—, —C(═N—O—R5)—C(R3)—O—N═C(CH3)—, —T—Ar1— or —T—Ar1—Q—;
- where Q, n, R3, R4 and R5 are each as defined in the application.
- In particular, G represents —C(R3)═N—O—CH2—, where R3 preferably represents cyclopropyl and in particular methyl.
- G preferably represents —T—Ar1—, —T—Ar1—S— and in particular —T—Ar1—O—, where
- T preferably represents a single bond, represents oxygen, sulphur, —CH2—O—, —CH2—S— or represents alkanediyl having 1 to 3 carbon atoms, in particular represents a single bond, represents oxygen, sulphur, —CH2—O—, —CH2—S—, methylene, ethylene or propylene and preferably oxygen.
- Ar1 preferably represents phenylene, naphthylene, cycloalkylene, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heteroarylene or heterocycloalkylene having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and also
- cycloalkyl having 3 to 6 carbon atoms and
- Ar1 in particular
- represents phenylene or pyridinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, represents in each case optionally monosubstituted pyrimidinediyl, pyridazineidyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-,i-,s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and
- Ar1 preferably
- represents 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or disubstituted by identical or different substituents, possible substituents being the substituents mentioned above, or particularly preferably represents 1,2,4-thiadiazolediyl or pyrimidinediyl which is optionally mono- or disubstituted by identical or different substituents, possible substituents being those mentioned above, where the substituents preferably represent halogen, in particular fluorine.
- In the general formula (l),
- Z preferably represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl and C1-C4-alkylsulphonyl (each of which may optionally be substituted by halogen);
- represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms;
- represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy), C1-C4-alkyl and C1-C4-alkoxy-carbonyl;
- represents phenyl, naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulphonyloxy, having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
- in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
- cycloalkyl having 3 to 6 carbon atoms;
- phenyl or phenoxy, each of which is mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
-
- in which
- A1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
-
- in which
- A3 represents alkyl having 1 to 4 carbon atoms and
- A4, A5, A6 and A7 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- In the general formula (I),
- Z in particular represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl;
- and preferably represents phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are each as defined above and preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,
- phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
-
- in which
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
-
- in which
- A3 represents methyl or ethyl and
- A4, A5, A6 and A7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- In the general formula (I),
- Z preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano or methoxy;
- represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl;
- and preferably represents phenyl, pyridyl, pyrimidyl or thienyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are as defined above and preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl or phenoxy;
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl;
- cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy, or
-
- in which
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- A2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
-
- in which
- A3 represents methyl or ethyl and
- A4, A5, A6 and A7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- In the general formula (I),
- Z particularly preferably represents pyridyl, pyrimidyl, each of which is optionally mono- to trisubstituted by identical or different substituents, and in particular represents phenyl which is unsubstituted or mono- to trisubstituted by identical or different substituents, where the possible substituents are as defined above and preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl or phenoxy;
- the present application preferably provides aminosalicylamides of the formula (I)
- in which
- R1 represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms,
- Y1, Y2, Y3, Y4 and Y5 are identical or different and each represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and either
- Y2 or Y3 represents —G—Z,
- in which
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH2—, —CH2—Q—CQ—, —Q—CQ—CH2—, —Q—CQ—Q—CH2—, —N═N—, —S(O)n—, —CH2—S(O)n—, —CQ—, —S(O)n—CH2—, —C(R3)═N—O—, —C(R3)═N—O—CH2—, —N(R4)—, —CQ—N(R4)—, —N(R4)—CQ—, —Q—CQ—N(R4)—, —N═C(R3)—Q—CH2—, —CH2—O—N═C(R3)—, —C(CH3)—O—N═C(R3)—, —N(R4)—CQ—Q—, —CQ—N(R4)—CQ—Q—, —N(R4)—CQ—Q—CH2—, —Q—C(R3)═N—O—CH2—, —N(R4)—C(R3)═N—O—CH2—, —O—CH2—C(R3)═N—O—CH2—, —N═N—C(R3)═N—O—CH2—,—C(═N—O—R5)—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)—O—N═CH—, —C(═N—O—R5)—C(R3)—O—N═C(CH3)—, —T—Ar1— or —T—Ar1—Q—,
- where
- n represents the numbers 0, 1 or 2,
- Q represents oxygen or sulphur,
- R3 represents hydrogen, cyano, represents in each case optionally halogen-, cyano- or C1-C1-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups or represents in each case optionally halogen-, cyano-, carboxyl-, C1-C1-alkyl- or C1-C1-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and
- R4 represents hydrogen, hydroxyl, cyano or represents optionally halogen-, cyano- or C1-C1-alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- or C1-C4-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
- R5 represents hydrogen or alkyl having 1 to 4 carbon atoms,
- Ar1 represents phenylene, naphthylene or cycloalkylene, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heteroarylene or heterocycloalkylene having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below: halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and also
- cycloalkyl having 3 to 6 carbon atoms and
- T represents a single bond, represents oxygen, sulphur, —CH2—O—, —CH2—S— or represents alkanediyl having 1 to 3 carbon atoms,
- Z represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl and C1-C4-alkylsulphonyl (each of which may optionally be substituted by halogen);
- represents in each case optionally halogen-substituted alkenyl or alkinyl having in each case up to 8 carbon atoms;
- represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted by halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy), C1-C4-alkyl and C1-C4-alkoxy-carbonyl;
- represents phenyl, naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulphonyloxy, having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
- in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
- cycloalkyl having 3 to 6 carbon atoms;
- phenyl or phenoxy, each of which is mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
-
- in which
- A1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- A2 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or
-
- in which
- A3 represents alkyl having 1 to 4 carbon atoms and
- A4, A5, A6 and A7 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- The present application relates in particular to compounds of the formula (I)
- in which
- R1 represents hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy,
- Y1, Y2, Y3, Y4 and Y5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
- Y2 or Y3 represents —G—Z,
- in which
- G represents one of the groupings below —Q—CQ—, —CQ—Q—, —CQ—Q—CH2—, —CH2—Q—CQ—, —Q—CQ—CH2—, —Q—CQ—Q—CH2—, —N═N—, —S(O)n—, —CH2—S(O)n—, —CQ—, —S(O)n—CH2—, —C(R3)═N—O—, —C(R3)═N—O—CH2—, —N(R4)—, —CQ—N(R4)—, —N(R4)—CQ—, —Q—CQ—N(R4)—, —N═C(R3)—Q—CH2—, —CH2—O—N═C(R3)—, —C(CH3)—O—N═C(R3)—, —N(R4)—CQ—Q—, —CQ—N(R4)—CQ—Q—, —N(R4)—CQ—Q—CH2—, —Q—C(R3)═N—O—CH2—, —N(R4)—C(R3 )N—O—CH2—, —O—CH2—C(R3)═N—O—CH2—, —N═N—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)═N—O—CH2—, —C(═N—O—R5)—C(R3)—O—N═CH—, —C(═N—O—R5)—C(R3)—O—N═C(CH3)—, —T—Ar1— or —T—Ar1—Q—,
- where
- n represents the numbers 0, 1 or 2,
- Q represents oxygen or sulphur,
- R3 represents hydrogen, cyano, methyl, ethyl or cyclopropyl and
- R4 represents hydrogen, methyl, ethyl or cyclopropyl,
- R5 represents hydrogen or methyl,
- Ar1 represents phenylene or pyridinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, represents in each case optionally monosubstituted pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and
- T represents a single bond, represents oxygen, sulphur, —CH2—O—, CH2—S—, methylene, ethylene or propylene,
- Z represents ethyl, n- or i-propyl, n-, i-, s- or t-butyl or methyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; or
- Z represents phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, i- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,
-
- in which
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
-
- in which
- A3 represents methyl or ethyl and
- A4, A5, A6 and A7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- A very particularly preferred groups of compounds according to the invention are those compounds of the formula (I),
- in which
- R1 represents hydrogen, methyl or methoxy,
- Y1, Y2, Y3, Y4 and Y5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
- Y2 or Y3 represents —G—Z,
- in which
- G represents —C(R3)═N—O—CH2—,
- in which
- R3 represents methyl or cyclopropyl, and
- Z represents phenyl, pyridyl or pyrimidyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case doubly attached methylenedioxy or ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl, and also phenyl and phenoxy.
- Likewise, particularly preferred groups of compounds according to the invention are those compounds of the formula (I):
- in which
- R1 represents hydrogen, methyl or methoxy.
- Y1, Y2, Y3, Y4 and Y5 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy.
- Y2 or Y3 represents —G—Z,
- in which
- G represents —T—Ar1— or —T—Ar1—O—,
- in which
- Ar1 represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methyl, cyclopropyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,
- T represents a single bond, represents oxygen, sulphur, —CH2—O—, CH2—S—, methylene, ethylene or propylene.
- Z represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano and methoxy;
- represents in each case optionally fluorine- or chlorine-substituted vinyl, allyl or propargyl;
- represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, cyano, methoxy, phenyl, methyl and ethyl; or
- Z represents phenyl, pyridyl, pyrimidyl or thienyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl
-
- in which
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
-
- in which
- A3 represents methyl or ethyl and
- A4, A5, A6 and A7 are identical or different and independently of one another each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.
- The radical definitions given in the respective combinations or preferred combinations of radicals individually for this radical are, independently of the respective given combination, replaced by any corresponding radical definition from other preferred ranges.
-
-
-
-
- where Z2 represents the substituents mentioned in Table 2.
- The formula (II) provides a general definition of the aminosalicylamides required as starting materials for carrying out the process a) according to the invention. In this formula (II), Y1, Y2, Y3, Y4 and Y5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y1, Y2, Y3, Y4 and Y5.
- The starting materials of the formula (II) are novel and also form part of the subject matter of the present application.
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above
- are reacted with a reducing agent, such as, for example, hydrogen, iron, zinc, tin-II chloride, sodium hydrogen sulphide or ammonium hydrogen sulphide, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst,
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above
- are reacted with hydrogen, if appropriate in the presence of a diluent, and if appropriate in the presence of a catalyst.
- The formula (IV) provides a general definition of the nitrosalicylamides required as starting materials for carrying out the process d) according to the invention. In this formula (IV), Y1, Y2, Y3, Y4 and Y5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y1, Y2, Y3, Y4 and Y5.
- The nitrosalicylamides of the formula (IV) are novel and also form part of the subject matter of the present application.
-
- in which
- Y1, Y2, Y3, Y4 and Y5 are each as defined above,
- if appropriate in the presence of a diluent, if appropriate in the presence of a condensing agent and if appropriate in the presence of an acid acceptor.
- Furthermore, it has been found that the novel nitrosalicylamides of the formula (IV) are suitable for controlling pests on plants and industrial materials, preferably fungi, insects and bacteria.
- The 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-nitrobenzoyl chloride required as starting materials for carrying out the process f) according to the invention are known (compare, for example, J.Chem.Soc., 1953 2049, 2050 or U.S. Pat. Ser. No. 03/527,865).
- The formula (VII) provides a general definition of the amines furthermore required as starting materials for carrying out the process f) according to the invention. In this formula (VII), Y1, Y2, Y3, Y4 and Y5 each preferably or in particular has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y1, Y2, Y3, Y4 and Y5.
- Some of the amines of the formula (VII) are known, and they can be prepared by known processes (compare, for example, WO-A 9601825, EP-A 192180).
-
- in which
- Y6, Y7, Y8, Y9 and Y10 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
-
- in which
- m represents 0 or 1,
- Ar2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidin-4,6-diyl which is optionally substituted in the 5 position by halogen and
- Z3 represents optionally substituted aryl.
- Preference is given to amines of the formula (VII-a)
- in which
- Y6, Y7, Y8, Y9 and Y10 are identical or different and each represents hydrogen, halogen, cyano, alkyl or alkoxy having in each case 1 to 4 carbon atoms, halogenoalkyl, or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and either
-
- in which
- m represents 0 or 1,
- Ar2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidine-4,6-diyl which is optionally substituted in the 5 position by fluorine or chlorine and
- Z3 represents phenyl or naphthyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulphonyloxy, having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
- in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
- cycloalkyl having 3 to 6 carbon atoms;
- phenyl or phenoxy, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and straight-chain or branched alkyl having 1 to 4 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—, or
-
- in which
- A8 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- A9 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or
-
- in which
- A10 represents alkyl having 1 to 4 carbon atoms and
- A11, A12, A13 and A14 are identical or different and, independently of one another, each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- A11 and A12 or A11 and A13 or A13 and A14 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
- Particular preference is given to amines of the formula (VII-a)
- in which
- Y6, Y7, Y8, Y9 and Y10 are identical or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either
-
- in which
- m represents 0 or 1,
- Ar2 represents 1,2,4-oxadiazole-3,5-diyl, 1,2,4-thiadiazole-3,5-diyl or represents pyrimidine-4,6-diyl which is optionally substituted in the 5 position by fluorine or chlorine and
- Z3 represents phenyl which is in each case optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- 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, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl or ethyl
- phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
-
- in which
- A8 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl,
- A9 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or
-
- in which
- A10 represents methyl or ethyl and
- A11, A12, A13 and A14 are identical or different and, independently of one another, each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- A11 and A12 or A11 and A13 or A13 and A14 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms.
-
- in which
- m represents 0 or 1,
- X2 represents hydrogen, fluorine or chlorine,
- X3 represents chlorine or fluorine,
- X4 represents methylsulphonyl, chlorine or bromine and
- Q represents oxygen or sulphur, and
- Z3 is as defined above
-
- in which
- Y11, Y12, Y13, Y14 and Y15 are identical or different and each represents hydrogen, halogen, cyano, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, and either
- Y12 or Y13 represents amino,
-
- in which
- X2, Y11, Y12, Y13, Y14 and Y15 are each as defined above and
- X5 represents chlorine or fluorine,
- are reacted with a phenol of the general formula (XII),
- Z3—OH (XII)
- in which
- Z3 is as defined above,
- if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
- The formula (VIII) provides a general definition of the diazoles required as starting materials for carrying out the process h) according to the invention. In this formula (VIII), m and Z3 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for m and Z3. X4 represents methylsulphonyl, chlorine or bromine.
- The diazoles of the formula (VIII) are known, and they can be prepared by known methods (compare, for example, DE-A 2142913).
- The formula (IX) provides a general definition of the halogenopyrimidines alternatively required as starting materials for carrying out the process h) according to the invention. In this formula (IX), m and Z3 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for m and Z3. X2 represents hydrogen, fluorine or chlorine. X3 represents fluorine or chlorine.
- Some of the halogenopyrimidines of the formula (IX) are known, and they can be prepared by known methods (cf. for example, Pharm.Chem.J.(Engl.Transl.), 23, 6, 1989, 500-503; RU, 23, 6, 1989, 705-707).
-
- in which
- Z3 is as defined above, except for the compound methyl 2-[(6-chloro-5-fluoro-4-pyrimidinyl)-oxy]-α-(methoxymethylene)-benzoate.
- The novel 4-chloro-5-fluoro-6-phenoxypyrimidines are obtained when (process j) phenols of the general formula (XII),
- Z3—OH (XII)
- in which
- Z3 is as defined above
- are reacted with 4,6-dichloro-5-fluoropyrimidine (XIII), if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
- The formula (XII) provides a general definition of the phenols required as starting materials for carrying out the process j) according to the invention. In this formula (XII), Z3 preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (VII-a) according to the invention as being preferred or as being particularly preferred for Z3.
- The phenols of the formula (XII) are known chemicals for synthesis, or they can be prepared by known processes (WO 95-04728).
- The 4,6-dichloro-5-fluoropyrimidine (XIII) furthermore required as starting material for carrying out the process j) according to the invention is novel and also forms part of the subject matter of the present application.
- It is obtained when (process k) 5-fluoro-6-hydroxy-4(1H)-pyrimidinone (XIV) is reacted with a chlorinating agent, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
- The 5-fluoro-6-hydroxy-4(1H)-pyrimidinone (XIV) required as starting material for carrying out the process k) according to the invention is known and can be prepared by known methods (JP 61205262; CA: 106:84632).
- The formula (XI) provides a general definition of the aminophenoxypyrimidines required as starting materials for carrying out the process i) according to the invention. In this formula (XI), Y11, Y12, Y13, Y14 and Y15 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the amines of the formula (X) as being preferred or as being particularly preferred for Y11, Y12, Y13, Y14 and Y15. X2 and X5 independently of one another each represent chlorine or fluorine.
- The aminophenoxypyrimidines of the formula (XI) are novel and also form part of the subject matter of the present application.
-
- in which
- X2 and X5 are each as defined above and
- X6 represents fluorine or chlorine
- are reacted with an aminophenol of the formula (X)
- if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
- The formula (XV) provides a general definition of the trihalogenopyrimidines required as starting materials for carrying out the process 1) according to the invention. In this formula (XV), X2 and X5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (XI) as being preferred or as being particularly preferred for X2 and X5. X6 represents fluorine or chlorine.
- Some of the trihalogenopyrimidines of the formula (XV) are known, and they can be prepared by known methods (compare, for example, Chesterfield et al., J. Chem. Soc., 1955; 3478, 3480). A special case of the compounds of the formula (XV) is the compound (XIII) according to the invention; it can be prepared by process k).
- The aminophenols of the formula (X) furthermore required as starting materials for carrying out the process 1) according to the invention have already been described further above in the description of the process h) according to the invention.
- The phenols of the formula (XII) furthermore required as starting materials for carrying out the process i) according to the invention have already been described further above in the description of the process j) according to the invention.
- The formula (V) provides a general definition of the O-benzyl-nitrosalicylamides required as starting materials for carrying out the process e) according to the invention. In this formula (V), Y1, Y2, Y3, Y4 and Y5 each preferably or in particular have those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for Y1, Y2, Y3, Y4 and Y5.
- The O-benzyl-nitrosalicylamides of the formula (V) have hitherto not been known, as novel substances, they form part of the subject matter of the present application.
-
- in which
- X7 represents halogen, hydroxyl or alkoxy,
- are reacted with an amine of the formula (VII),
- if appropriate in the presence of a diluent, if appropriate in the presence of a condensing agent and if appropriate in the presence of an acid acceptor.
- The formula (VI) provides a general definition of the O-benzyl-nitrosalicylic acid derivatives required as starting materials for carrying out the process g) according to the invention. In this formula (VI), X7 represents halogen, preferably chlorine; hydroxyl or alkoxy, preferably methoxy or ethoxy.
- The O-benzyl-nitrosalicylic acid derivatives of the formula (VI) are known, and they can be prepared by known methods (compare, for example, J. Am. Chem. Soc. 1959, 5215-5217).
- The amines of the formula (VII) furthermore required as starting materials for carrying out the process g) according to the invention have already been described further above in connection with the description of the process f) according to the invention.
- The formula (III) provides a general definition for the acylating agents furthermore required as starting materials for carrying out the process a) according to the invention. In this formula (III), R1 preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or as being particularly preferred for R1. X1 represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy, preferably chlorine, hydroxyl, methoxy, ethoxy or acetoxy.
- The acylating agents of the general formula (III) are known reagents in organic chemistry.
- The nitrosalicylamides of the formula (IV) required as starting materials for carrying out the process b) according to the invention have already been described further above in connection with the description of the process d) according to the invention.
- The O-benzyl-nitrosalicylamides of the formula (V) required as starting materials for carrying out the process c) according to the invention have already been described further above in connection with the description of the process e) according to the invention.
- Suitable diluents for carrying out the processes a), f) and g) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide or sulphones, such as sulpholane.
- Suitable diluents for carrying out the processes d) and e) according to the invention are all inert organic solvents. These preferably include esters such as methyl acetate or ethyl acetate; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethlylene glycol monomethyl ether, diethylene glycol monoethyl ether, water, salt solutions, such as, for example, ammonium chloride solution, acids, such as, for example, hydrochloric acid or acetic acid, and also any mixtures of the abovementioned diluents.
- Suitable diluents for carrying out the processes h), i), j) and 1) according to the invention are all inert organic solvents. These preferably include ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; sulphoxides, such as dimethyl sulfoxide; or sulphones, such as sulpholane.
- Suitable diluents for carrying out the process k) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile.
- The processes a), f) and g) according to the invention are, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
- The processes b), c), d) and e) according to the invention are, if appropriate, carried out in the presence of a catalyst. Suitable catalysts are all catalysts which are also usually employed for hydrogenations. Examples include: Raney nickel, palladium or platinum, if appropriate on a support, such as, for example, activated carbon.
- The process c) according to the invention is, if appropriate, also carried out in the presence of hydrogen or, if appropriate, in the presence of a base metal. Suitable base metals are, for example: zinc, tin, iron, aluminium or magnesium.
- Suitable further reaction auxiliaries for carrying out the processes a), b) and c) according to the invention are all dehydrating agents, in particular acetic anhydride.
- The processes f) and g) according to the invention are, if appropriate, carried out in the presence of a condensing agent. These preferably include acyl halide formers such as, for example, phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulphonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine/carbon tetrachloride.
- The processes h), i), j) and 1) according to the invention are, if appropriate, carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, alkoxides, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate.
- Suitable catalysts for processes h), i), j) and l) according to the invention are all copper(I) salts, such as, for example, copper(I) chloride, copper(I) bromide or copper(I) iodide, or else fluorides, such as, for example, sodium fluoride, potassium fluoride or ammonium fluoride, and also tertiary ammonium fluorides, such as tetrabutylammonium fluoride.
- The process k) according to the invention is, if appropriate, carried out in the presence of a suitable catalyst. Suitable catalysts are all tertiary amines, such as, for example, trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), and also amides, such as dimethylformamide.
- Suitable halogenating agents for carrying out the process k) according to the invention are all reagents which are capable of exchanging hydroxyl groups which are attached to carbon for chlorine. Examples include: phosgene, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride and, if appropriate, additionally hydrogen chloride or chlorine.
- When carrying out the processes a), b), c), d), e), f) and g) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures from 0° C. to 180° C., preferably at temperatures from 0° C. to 130° C.
- When carrying out the processes h), i), j) and 1) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures from −20° C. to 200° C., preferably at temperatures from −10° C. to 150° C.
- When carrying out the process k) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures from 0° C. to 250° C., preferably at temperatures from 0° C. to 200° C.
- For carrying out the process a) according to the invention for preparing the compounds of the formula (I), generally from 1 to 2000 mol, preferably from 1 to 800 mol, of acylating agent of the formula (III) are employed per mole of the aminosalicylamide of the formula (II).
- For carrying out the processes b) and c) according to the invention for preparing the compounds of the formula (I), generally from 100 to 2000 mol, preferably from 200 to 1000 mol, of formic acid are employed per mole of the nitrosalicylamide of the formula (IV), or of the O-benzyl-nitrosalicylamide of the formula (V).
- For carrying out the process d) according to the invention for preparing the compounds of the formula (II), generally from 1 to 100 mol, preferably from 2 to 20 mol, of reducing agent are employed per mole of the nitrosalicylamide of the formula (IV).
- For carrying out the process e) according to the invention for preparing the compounds of the formula (II), generally from 1 to 100 mol, preferably from 2 to 50 mol, of hydrogen are employed per mole of the O-benzyl-nitrosalicylamide of the formula (V).
- For carrying out the process f) according to the invention for preparing the compounds of the formula (IV), generally from 0.5 to 10 mol, preferably from 0.8 to 5 mol, of 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-nitrobenzoyl chloride are employed per mole of amine of the formula (VII).
- For carrying out the process g) according to the invention for preparing the compounds of the formula (V), generally from 0.5 to 10 mol, preferably from 0.8 to 5 mol, of O-benzyl-nitrosalicylic acid derivatives of the formula (VI) are employed per mole of the amine of the formula (VII).
- For carrying out the process h) according to the invention for preparing the compounds of the formula (VII-a), generally from 0.5 to 5 mol, preferably from 0.8 to 2 mol, of halogenopyrimidine of the formula (IX) or diazole of the formula (VIII) are employed per mole of the aminophenol of the formula (X).
- For carrying out the process i) according to the invention for preparing the compounds of the formula (VII-a), generally from 0.5 to 5 mol, preferably from 0.8 to 2 mol, of aminophenoxypyrimidine (XI) are employed per mole of the phenol of the formula (XII).
- For carrying out the process j)according to the invention for preparing the compounds of the formula (IX-a), generally from 0.5 to 5 mol, preferably from 0.8 to 2 mol, of 4,6-dichloro-5-fluoropyrimidine (XIII) are employed per mole of the phenol of the formula (XII).
- For carrying out the process k) according to the invention for preparing 4,6-dichloro-5-fluoropyrimidine (XIII), generally from 0.05 to 20 mol, preferably from 0.1 to 10 mol, of halogenating agent are employed per mole of 5-fluoro-6-hydroxy-4(1H)-pyrimidinone (XIV).
- For carrying out the process l) according to the invention for preparing the compounds of the formula (XI), generally from 0.5 to 5 mol, preferably from 0.8 to 2 mol, of trihalogenopyrimidine (XV) are employed per mole of the aminophenol of the formula (X).
- The processes a) to l) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure—in general between 0.1 bar and 10 bar.
- The compounds according to the invention have potent microbicidal activity and can be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
- Fungicides are employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
- Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
- Some pathogens causing fungal and bacterial diseases which come under the generic names listed above are mentioned as examples, but not by way of limitation:
- Xanthomonas species, such as, for example,Xanthomonas campestris pv. oryzae;
- Pseudomonas species, such as, for example,Pseudomonas syringae pv. lachrymans;
- Erwinia species, such as, for example,Erwinia amylovora;
- Pythium species, such as, for example,Pythium ultimum;
- Phytophthora species, such as, for example,Phytophthora infestans;
- Pseudoperonospora species, such as, for example,Pseudoperonospora humuli or Pseudoperonospora cubensis;
- Plasmopara species, such as, for example,Plasmopara viticola;
- Bremia species, such as, for example,Bremia lactucae;
- Peronospora species, such as, for example,Peronospora pisi or P. 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 P. graminea (conidia form: Drechslera, syn: Helminthosporium);
- Cochliobolus species, such as, for example,Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);
- Uromyces species, such as, for example,Uromyces appendiculatus;
- Puccinia species, such as, for example,Puccinia recondita;
- Sclerotinia species, such as, for example,Sclerotinia sclerotiorum
- 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;
- Altemaria species, such as, for example,Altemaria brassicae;
- Pseudocercosporella species, such as, for example,Pseudocercosporella herpotrichoides.
- The fact that the active compounds are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil.
- The active compounds according to the invention can be employed particularly successfully for controlling diseases in fruit and vegetable growing and viticulture, such as, for example, against Venturia Phytophthora species. They are also very successfully used for controlling cereal diseases, such as, for example, Pseudocercosporella species, or for controlling rice diseases, such as, for example, Pyricularia species.
- The active compounds according to the invention are also suitable for increasing the harvest yield. Moreover, they show reduced toxicity and are well tolerated by plants.
- Depending on their particular physical and/or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and micro-encapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
- These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam-formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, the following are suitable for use as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example 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 sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
- Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other suitable additives are mineral and vegetable oils.
- It is possible to use colourants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
- Depending on their particular physical and/or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
- The active compounds according to the invention can be used as such or in their formulations also mixed with known fungicides, bactericides, acaricides, nematicides or insecticides in order thus, for example, to widen the spectrum of action or to prevent development of resistance. In many cases, synergistic effects are achieved, i.e. the activity of the mixture exceeds the activity of the individual components.
- Examples of co-components in mixtures are the following compounds:
- Fungicides:
- aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
- benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
- calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,
- debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,
- ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
- famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, fumecyclox,
- guazatine,
- hexachlorobenzene, hexaconazole, hymexazole,
- imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfosufen (IBP), iprodione, irumamycin, isoprothiolane, isovaledione,
- kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
- mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
- nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
- ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
- paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
- quinconazole, quintozene(PCNB),
- sulphur and sulphur preparations,
- tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole, thiabendazole, thicyofen, thifuzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
- uniconazole,
- validamycin A, vinclozolin, viniconazole,
- zarilamide, zineb, ziram and also
- Dagger G,
- OK-8705,
- OK-8801,
- α(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,
- α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
- α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
- α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,
- (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,
- (E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,
- isopropyl {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,
- 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,
- 1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,
- 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,
- 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,
- 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,
- 1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,
- 1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,
- 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,
- 2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,
- 2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,
- 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,
- 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,
- 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,
- 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,
- 2-[(1-methylethyl)sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,
- 2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
- 2-aminobutane,
- 2-bromo-2-(bromomethyl)-pentanedinitrile,
- 2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,
- 2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,
- 2-phenylphenol (OPP),
- 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,
- 3,5-dichloro-N-[cyano[(1-methyl-2-propinyl)-oxy]-methyl]-benzamide,
- 3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
- 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,
- 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide,
- 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,
- 8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methaneamine,
- 8-hydroxyquinoline sulphate,
- 9H-xanthene-2-[(phenylamino)-carbonyl-9-carboxylic hydrazide,
- bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
- cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,
- cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,
- ethyl [(4-chlorophenyl)-azo]-cyanoacetate,
- potassium hydrogen carbonate,
- methanetetrathiol sodium salt,
- methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,
- methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,
- methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,
- N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,
- N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,
- N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
- N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulfonamide,
- N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,
- N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,
- N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetanide,
- N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,
- N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,
- N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methaneimidamide,
- N-formyl-N-hydroxy-DL-alanine sodium salt,
- O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
- O-methyl S-phenyl phenylpropylphosphoramidothioate,
- S-methyl 1,2,3-benzothiadiazole-7-carbothioate,
- spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,
- Bactericides:
- bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloflalam, copper sulphate and other copper preparations.
- Insecticides/Acaricides[Nematicides:
- abamectin, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
-
- cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, N-[(6-chloro-3-pyridinyl)-methyl]-N′-cyano-N-methyl-ethanimidamide, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
- deltamethrin, demeton M, demeton S, demeton S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,
- edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos,
- fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron, flucythninate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
- HCH, heptenophos, hexaflumuron, hexythiazox,
- imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,
- lambda-cyhalothrin, lufenuron,
- malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
- naled, NC 184, nitenpyram,
- omethoate, oxamyl, oxydemethon M, oxydeprofos,
- parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenophos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
- quinalphos,
- salithion, sebufos, silafluofen, sulfotep, sulprofos,
- tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,
- vamidothion, XMC, xylylcarb, zetamethrin.
- It is also possible to admix other known active compounds, such as herbicides, fertilizers and growth-regulating substances.
- The active compounds can be used as such or in the form of their commercial formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, spreading, dusting, foaming, brushing-on and the like. It is further possible to apply the by the ultra-low volume method or to inject the preparation of active compound, or the active compound itself, into the soil. The seed of the plants can also be treated.
- When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of soil, the active compound application rates are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
-
- Process c)
- 1.67 g (3.02 mmol) of 2-benzyloxy-N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-3-nitro-benzamide in 20 ml of formic acid are stirred with 0.4 g of Raney nickel at 40° C. for 24 hours. The mixture is poured into water and extracted repeatedly with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using cyclohexane/ethyl acetate (1:1). This gives 0.4 g (35% of theory) of N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-3-formyl-amino-2-hydroxy-benzamide as a colourless oil.
- HPLC: logP=3.31
-
- Process b)
- 0.5 g (1.08 mmol) of N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-2-hydroxy-3-nitrobenzamide in 10 ml of formic acid are stirred with 0.5 g of Raney nickel at 40° C. for 24 hours. The mixture is poured into water and extracted repeatedly with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using cyclohexane/ethyl acetate (1:1). This gives 0.4 g (81% of theory) of N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-3-formyl-amino-2-hydroxy-benzamide as a colourless oil.
- HPLC: logP=3.31
- Preparation of Compounds of the Formula (IV)
-
- Process f)
- A mixture of 1.7 g (9 mmol) of 3-nitrosalicylic acid and 2.7 g (9 mmol) of 4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenylamine in 20 ml of toluene is heated with stirring to 50° C. 0.5 g of phosphorus trichloride is added, and the mixture is heated at the boil under reflux for a further 4 hours. After cooling, the mixture is concentrated and the residue is extracted with dichloromethane. The organic phase is washed repeatedly with water and dried over sodium sulphate. The solvent is distilled off, giving 1.7 g (41% of theory) of N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-2-hydroxy-3-nitrobenzamide.
- Mass spectrum: m/e=462 (M+)
- Preparation of Compounds of the Formula (V)
-
- Process g)
- At 0° C., a solution of 2.4 g (0.011 mol) of triethylamine and 5.3 g (18 mmol) of 4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenylamine in 30 ml of dichloromethane is added dropwise to a solution of 4.3 g (18 mmol) of 2-benzyloxy-3-nitro-benzoyl chloride in 20 ml of dichloromethane, and the mixture is stirred without further cooling for another 2 hours. The mixture is filtered and the filtrate is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel using cyclohexane/ethyl acetate (2:1). This gives 2.8 g (30% of theory) of 2-benzyloxy-N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-3-nitro-benzamide as an oil.
- HPLC: logP=4.56
- Preparation of Compounds of the Formula (IX-a)
-
- Process j)
- To a mixture of 5 g (0.0295 mol) of 4,6-dichloro-5-fluoropyrimidine and 5 g (0.036 mol) of potassium carbonate in 25 ml of acetonitrile is heated to 50° C. At this temperature, a solution of 3.8 g (0.03 mol) of 2-chlorophenol in 25 ml of acetonitrile is added dropwise over a period of 6 hours, and the mixture is stirred at this temperature for a further 6 hours. After cooling, the solvent is distilled off under reduced pressure and the residue is taken up in water and extracted repeatedly with in each case 40 ml of dichloromethane. The organic phase is washed with 10% strength aqueous sodium hydroxide solution, dried over sodium sulphate and reconcentrated under reduced pressure. This gives 6.9 g (86.7% of theory) of 4-chloro-6-(2-chlorophenoxy)-5-fluoropyrimidine.
-
-
- Process j)
- To a mixture of 3 g (0.018 mol) of 4,6-dichloro-5-fluoropyrimidine and 2.7 g (0.018 mol) of potassium carbonate in 30 ml of acetonitrile is heated to 70° C. At this temperature, a solution of 3.8 g (0.03 mol) of (5,6-dihydro-[1.4.2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl oxime in 20 ml of acetonitrile is added dropwise over a period of 2 hours, and the mixture is heated under reflux for a further 16 hours. After cooling, the solvent is distilled off under reduced pressure and the residue is taken up in water and extracted repeatedly with in each case 40 ml of dichloromethane. The organic phase is washed with 10% strength aqueous sodium hydroxide solution, dried over sodium sulphate and reconcentrated under reduced pressure. This gives 7 g (86.7% of theory) of [2-(6-chloro-5-fluoropyrimidine-4-yloxy)-phenyl]-(5,6-dihydro-[1.4.2]-dioxazin-3-yl)-methanone O-methyl oxime.
-
- Preparation of 4,6-dichloro-5-fluoropyrimidine
-
- Process k)
- Over a period of 30 minutes, 7.8 g (0.064 mol) of N,N-dimethylaniline are added dropwise to 30 ml of phosphorus oxychloride, and the mixture is stirred at 25° C. for 10 minutes. 8.3 g of 5-fluoropyrimidine-4,6-diole are subsequently added, and the mixture is heated under reflux for 15 hours. After cooling, the excess phosphorus oxychloride is distilled off under water pump vacuum and the residue is subjected to vacuum distillation. This gives 11.2 g (100% of theory) of 4,6-dichloro-5-fluoropyrimidine of boiling point 58-60° C. at 14 mbar.
- Preparation of compounds of the formula (VII-a)
-
- Process i)
- A mixture of 2 g (9 mmol) of 4-(4-aminophenoxy)-6-chloro-pyrimidine, 1.1 g (9 mmol) of 3-chlorophenol and 2 g (18 mmol) of dried potassium carbonate in 20 ml of acetonitrile is heated under reflux for 4 hours. The mixture is subsequently filtered and the filtrate is concentrated under reduced pressure. The residue is taken up in dichloromethane, washed with water, and the organic phase is dried over sodium sulphate and reconcentrated under reduced pressure. This gives 1.3 g (46% of theory) of 4-(4-aminophenoxy)-6-(2-chlorophenoxy)-pyrimidine.
- HPLC: logP=1.96
- Preparation of Compounds of the Formula (XI)
-
- Process l)
- A mixture of 50 g (0.3 mol) of 4,6-dichloropyrimidine, 37 g (0.3 mol) of 4-aminophenol, 80 g (0.6 mol) of dried potassium carbonate and 50 mg of copper-II bromide in 600 ml of acetonitrile is heated under reflux for 4 hours. The mixture is subsequently filtered and the filtrate is concentrated under reduced pressure. The residue is taken up in dichloromethane, washed with water, and the organic phase is dried over sodium sulphate and reconcentrated under reduced pressure. This gives 60 g (58% of theory) of 4-(4-aminophenoxy)-6-chloro-pyrimidine.
- HPLC: logP=0.65
-
- 2.7 g of 6-chloro-5-fluoro-4-(2-chlorophenyloxy)pyrimidine and 1.5 g of potassium carbonate are initially charged in 20 ml of acetonitrile and, under reflux, admixed with 1.8 g of 2,3-dichloro-aminophenol over a period of 1.5 hours. The mixture is heated under reflux for a further 12 hours, cooled, the solvent is removed under reduced pressure and the residue is taken up in 45 ml of dichloromethane. The solution is washed with 0.25 N of aqueous sodium hydroxide solution and then admixed with 5 g of activated carbon and filtered, and the solvent is distilled off. The residue is chromatographed over silica gel using petroleum ether/ethyl acetate (2:1). This gives 2.7 g (64.3%) of 2,3-dichloro-4-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]-phenylamine of melting point 162-163° C.
- The compounds of the formula (I-f) mentioned in Table 5 below were obtained by the method of Example 1, and in accordance with the general description of the processes b) and c) according to the invention:
TABLE 5 Example Y2 Y3 logP 2 —H 2.96 3 —H 3.62 4 —H 3.61 5 —CH3 3.35 6 —H 3.07 7 —H 3.26 8 —H 3.21 9 —H 3.86 10 —H 3.09 11 —H 3.58 12 —H 3.19 13 —H 3.53 14 —H 3.86 15 —H 2.95 16 —H 3.86 17 —H 3.39 18 —H 3.79 19 —H 3.61 20 —H 3.27 21 —H 3.59 22 —H 2.82 23 —H 3.00 24 —H 3.17 25 —H 2.88 26 —H 3.55 27 —H 4.09 28 —H 3.58 29 —H 4.10 30 —H 3.88 31 —H 3.20 32 —H 3.90 -
- * mass spectrum
- The compounds of the formula (VI-a) mentioned in Table 7 below were obtained by the method of Example (V-1), and in accordance with the general description of the process g) according to the invention:
TABLE 7 (V-a) Example Y2 Y3 logP (V-2) —H 4.24 (V-3) —H 4.83 (V-4) —H 5.75 (V-5) —H 4.99 (V-6) —H 3.77 (V-7) —CH3 4.65 (V-8) —H 4.33 (V-9) —H 4.55 (V-10) —H 4.55 (V-11) —H 4.73 (V-12) —H 4.35 (V-13) —H 4.79 (V-14) —H 4.42 (V-15) —H 4.80 (V-16) —H 5.12 (V-17) —H 5.05 (V-18) —H 4.21 (V-19) —H 5.05 (V-20) —H 4.77 (V-21) —H 4.69 (V-22) —H 4.90 (V-23) —H 4.56 (V-24) —H 4.84 (V-25) —H 4.28 (V-26) —H 4.42 (V-27) —H 5.39 (V-28) —H 4.15 (V-29) —H 4.85 (V-30) —H 4.96 (V-31) —H 5.06 (V-32) —H 4.52 (V-33) —H 4.09 (V-34) —H 5.12 - (V-a)
TABLE 7 Example Y2 Y3 logP (V-2) —H 4.24 (V-3) —H 4.83 (V-4) —H 5.75 (V-5) —H 4.99 (V-6) —H 3.77 (V-7) —CH3 4.65 (V-8) —H 4.33 (V-9) —H 4.55 (V-10) —H 4.55 (V-11) —H 4.73 (V-12) —H 4.35 (V-13) —H 4.79 (V-14) —H 4.42 (V-15) —H 4.80 (V-16) —H 5.12 (V-17) —H 5.05 (V-18) —H 4.21 (V-19) —H 5.05 (V-20) —H 4.77 (V-21) —H 4.69 (V-22) —H 4.90 (V-23) —H 4.56 (V-24) —H 4.84 (V-25) —H 4.28 (V-26) —H 4.42 (V-27) —H 5.39 (V-28) —H 4.15 (V-29) —H 4.85 (V-30) —H 4.96 (V-31) —H 5.06 (V-32) —H 4.52 (V-33) —H 4.09 (V-34) —H 5.12 - The compounds of the formula (VII-b) mentioned in Table 8 below were obtained by the methods of Examples (VII-a-1) and (VII-a-2), and in accordance with the general description of the processes h) and i) according to the invention:
TABLE 8 (VII-b) Ex. No. Y10 Y9 Ar2 m Z3 m.p.: LogP VII-a-3 —H —H 1 phenyl 130 1.53 VII-a-4 —H —H 0 phenyl 2.57 VII-a-5 —H —H 1 phenyl 1.88 VII-a-6 —H —CH3 1 phenyl 2.32 VII-a-7 —H —H 1 4-chloro- phenyl 2.12 VII-a-8 —H —H 1 3,4-difluoro- phenyl 4.55 VII-a-9 —H —H 1 4-bromo- phenyl 2.02 VII-a-10 —H —H 1 2,4-dichloro- phenyl 2.33 VII-a-11 —H —H 1 3,4-dichloro- phenyl 2.48 VII-a-12 —H —H 1 3-methoxy- phenyl 1.61 VII-a-13 —H —H 1 4-tri- fluoromethyl- phenyl 2.21 VII-a-14 —H —H 1 3-tri- fluoromethyl- phenyl 2.18 VII-a-15 —H —H 1 2-fluoro- phenyl 1.61 VII-a-16 —H —H 1 3-fluoro- phenyl 1.46 VII-a-17 —H —H 1 3-tolyl 2.12 VII-a-18 —H —H 1 2,5-dichloro- phenyl 2.26 VII-a-19 —H —H 1 2,3-dimethyl- phenyl 1.98 VII-a-20 —H —H 1 3,5-dimethyl- phenyl 2.12 VII-a-21 —H —H 1 2,4-difluoro- phenyl 1.76 VII-a-22 —H —H 1 3,5-dichloro- phenyl 2.6 VII-a-23 —H —H 1 4-methoxy- phenyl 1.52 VII-a-24 —H —H 1 4-fluoro- phenyl 1.59 VII-a-25 —H —H 1 3-bromo- phenyl 2.05 VII-a-26 —H —H 1 2,3-dichloro- phenyl 2.26 VII-a-27 —H —H 1 2,5-dimethyl- phenyl 2.02 VII-a-28 —H —H 1 4-phenoxy- phenyl 2.55 VII-a-29 —H —H 1 2-methoxy- phenyl 1.46 VII-a-30 —H —H 1 2-tolyl 1.71 VII-a-31 —H —H 1 3-phenoxy- phenyl 2.54 VII-a-32 —H —H 1 2-chloro- phenyl 3.61 VII-a-33 —H —H 1 2,6-dimethyl- phenyl VII-a-34 —-H —H 1 2,6-dichloro- phenyl - Phytophthora Test (Tomato)/Protective
- Solvent: 47 parts by weight of acetone
- Emulsifier: 3 parts by weight of alkylaryl polyglycol ether
- To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension ofPhytophthora infestans. The plants are then placed in an incubation cabin at approximately 20° C. and 100% relative atmospheric humidity.
- Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
- In this test, for example, the following compounds of Preparation Examples 1, 2 and 4 exhibit, at an exemplary active compound application rate of 100 g/ha, an efficacy of more than 80%, compared with the untreated control.
- Venturia Test (Apple)/Protective
- Solvent: 47 parts by weight of acetone
- Emulsifier: 3 parts by weight of alkylaryl polyglycol ether
- To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causative organism of apple scabVenturia inaequalis and then remain in an incubation cabin at approximately 20° C. and 100% relative atmospheric humidity for 1 day.
- The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.
- Evaluation is carried out 12 days after the evaluation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
- In this test, for example, the following compounds of Preparation Examples 1 and 2 exhibit, at an exemplary active compound application rate of 100 g/ha, an efficacy of more than 80%, compared with the untreated control.
Claims (27)
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US4847258A (en) * | 1986-08-26 | 1989-07-11 | Ciba-Geigy Corporation | Substituted benzoylphenylureas compounds useful as pesticides |
GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
GB9413975D0 (en) | 1994-07-11 | 1994-08-31 | Fujisawa Pharmaceutical Co | New heterobicyclic derivatives |
EP0463488B2 (en) * | 1990-06-27 | 2004-04-21 | BASF Aktiengesellschaft | O-Benzyl oxime ethers and fungicides containing them |
NZ242290A (en) * | 1991-04-15 | 1994-12-22 | Zeneca Ltd | Pyridyl and pyrimidinyl substituted oxime-o-benzyl ether derivatives; preparatory processes, fungicidal compositions and an intermediate |
TW234077B (en) | 1992-07-17 | 1994-11-11 | Shell Internat Res Schappej B V | |
ZW8594A1 (en) | 1993-08-11 | 1994-10-12 | Bayer Ag | Substituted azadioxacycbalkenes |
DE4340181A1 (en) * | 1993-11-25 | 1995-06-01 | Bayer Ag | 3-methoxy-2-phenyl-acrylic acid methyl ester |
RU2154629C2 (en) | 1994-03-10 | 2000-08-20 | Байер Аг | Oxime derivatives, method of preparing thereof, fungicidal agent, and method of controlling fungal diseases |
DE19501842A1 (en) * | 1995-01-23 | 1996-07-25 | Bayer Ag | Substituted arylazadioxacycloalkenes |
TR199800327T1 (en) | 1995-08-30 | 1998-06-22 | Bayer Aktiengesellschaft | A�ilaminosalisilamidler. |
-
1997
- 1997-03-14 DE DE19710609A patent/DE19710609A1/en not_active Withdrawn
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1998
- 1998-03-02 JP JP54006898A patent/JP4416842B2/en not_active Expired - Lifetime
- 1998-03-02 DE DE59813369T patent/DE59813369D1/en not_active Expired - Lifetime
- 1998-03-02 CN CNB031038972A patent/CN1229329C/en not_active Expired - Lifetime
- 1998-03-02 CN CN98803332A patent/CN1121393C/en not_active Expired - Lifetime
- 1998-03-02 DK DK05002366.2T patent/DK1533303T3/en active
- 1998-03-02 PL PL98335842A patent/PL335842A1/en not_active IP Right Cessation
- 1998-03-02 AU AU68256/98A patent/AU6825698A/en not_active Abandoned
- 1998-03-02 BR BRPI9808255-8A patent/BR9808255B1/en not_active IP Right Cessation
- 1998-03-02 ES ES05002366T patent/ES2422894T3/en not_active Expired - Lifetime
- 1998-03-02 EP EP05002366.2A patent/EP1533303B1/en not_active Expired - Lifetime
- 1998-03-02 ES ES98913618T patent/ES2256934T3/en not_active Expired - Lifetime
- 1998-03-02 WO PCT/EP1998/001164 patent/WO1998041513A2/en active IP Right Grant
- 1998-03-02 EP EP98913618A patent/EP0970057B1/en not_active Expired - Lifetime
- 1998-03-02 CN CNB2005100531247A patent/CN1303071C/en not_active Expired - Lifetime
- 1998-03-02 DK DK98913618T patent/DK0970057T3/en active
- 1998-03-02 US US09/380,969 patent/US6194418B1/en not_active Expired - Lifetime
- 1998-03-02 EP EP10182907A patent/EP2292608A1/en not_active Withdrawn
- 1998-03-02 IL IL13186598A patent/IL131865A/en not_active IP Right Cessation
-
2000
- 2000-12-19 US US09/740,450 patent/US6380386B2/en not_active Expired - Lifetime
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2009
- 2009-02-19 JP JP2009036308A patent/JP5148526B2/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6734304B2 (en) | 2000-03-24 | 2004-05-11 | Bayer Aktiengesellschaft | Method for producing asymmetrical 4,6-bis(aryloxy)pyrimidine derivatives |
US20050124498A1 (en) * | 2002-03-01 | 2005-06-09 | Fritz Maurer | Halobenzyl substituted phenylaceto esters and amides and use thereof for prevention of harmful organisms |
US20070191628A1 (en) * | 2003-08-18 | 2007-08-16 | Bayer Cropscience Aktiengesellschaft | Method for producing alpha-fluoromalonic acid dialkyl esters |
US7807851B2 (en) | 2003-08-18 | 2010-10-05 | Bayer Cropscience Ag | Method for producing α-fluoromalonic acid dialkyl esters |
CN103721626A (en) * | 2013-12-11 | 2014-04-16 | 浙江工业大学 | Synthesis and application of reticular non-ionic surfactant containing fluorine |
Also Published As
Publication number | Publication date |
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BR9808255B1 (en) | 2009-08-11 |
DE19710609A1 (en) | 1998-09-17 |
DE59813369D1 (en) | 2006-04-13 |
ES2256934T3 (en) | 2006-07-16 |
CN1440962A (en) | 2003-09-10 |
EP0970057A2 (en) | 2000-01-12 |
JP5148526B2 (en) | 2013-02-20 |
CN1229329C (en) | 2005-11-30 |
DK0970057T3 (en) | 2006-05-29 |
AU6825698A (en) | 1998-10-12 |
EP1533303B1 (en) | 2013-04-24 |
ES2422894T3 (en) | 2013-09-16 |
CN1121393C (en) | 2003-09-17 |
DK1533303T3 (en) | 2013-07-29 |
EP2292608A1 (en) | 2011-03-09 |
WO1998041513A2 (en) | 1998-09-24 |
BR9808255A (en) | 2000-05-16 |
US6380386B2 (en) | 2002-04-30 |
JP4416842B2 (en) | 2010-02-17 |
CN1654459A (en) | 2005-08-17 |
PL335842A1 (en) | 2000-05-22 |
CN1303071C (en) | 2007-03-07 |
IL131865A0 (en) | 2001-03-19 |
WO1998041513A3 (en) | 1999-03-11 |
CN1250442A (en) | 2000-04-12 |
EP1533303A1 (en) | 2005-05-25 |
IL131865A (en) | 2004-08-31 |
EP0970057B1 (en) | 2006-02-01 |
JP2009149672A (en) | 2009-07-09 |
JP2001515497A (en) | 2001-09-18 |
US6194418B1 (en) | 2001-02-27 |
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