DE4029648A1 - 4-ANILINO-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDES - Google Patents
4-ANILINO-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDESInfo
- Publication number
- DE4029648A1 DE4029648A1 DE4029648A DE4029648A DE4029648A1 DE 4029648 A1 DE4029648 A1 DE 4029648A1 DE 4029648 A DE4029648 A DE 4029648A DE 4029648 A DE4029648 A DE 4029648A DE 4029648 A1 DE4029648 A1 DE 4029648A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- optionally substituted
- alkoxy
- alkylthio
- halo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- JLVLBDODYLEYOY-UHFFFAOYSA-N n-phenylpyrimidin-4-amine Chemical compound C=1C=NC=NC=1NC1=CC=CC=C1 JLVLBDODYLEYOY-UHFFFAOYSA-N 0.000 title description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 373
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 58
- 150000002367 halogens Chemical class 0.000 claims abstract description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 46
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 22
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 241000233866 Fungi Species 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 6
- -1 hydroxy, amino, nitro, cyano, thiocyano Chemical group 0.000 claims description 53
- 125000004414 alkyl thio group Chemical group 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 8
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims description 8
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 8
- 125000004693 haloalkylthiocarbonyl group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 4
- 125000006805 (C3-C9) cycloalkylamino group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 150000002390 heteroarenes Chemical class 0.000 claims 2
- 101100006371 Arabidopsis thaliana CHX3 gene Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 4
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
- 229910019213 POCl3 Inorganic materials 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- ALMBOXQFPLQVLF-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC(C)=CC(Cl)=N1 ALMBOXQFPLQVLF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 239000013589 supplement Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 241001668536 Oculimacula yallundae Species 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 3
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 3
- 229910052939 potassium sulfate Inorganic materials 0.000 description 3
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- LDBWHCHTYQUBIP-UHFFFAOYSA-N 4-chloro-6-methyl-2-prop-1-ynoxypyrimidine Chemical compound ClC1=NC(=NC(=C1)C)OC#CC LDBWHCHTYQUBIP-UHFFFAOYSA-N 0.000 description 2
- OCOHPSHRDKBGOZ-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C=C(C)N1 OCOHPSHRDKBGOZ-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JXSLKLPKMIQFRT-UHFFFAOYSA-N n,6-dimethyl-2-methylsulfanyl-n-phenylpyrimidin-4-amine Chemical compound CSC1=NC(C)=CC(N(C)C=2C=CC=CC=2)=N1 JXSLKLPKMIQFRT-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
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- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
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- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
- LCRMGUFGEDUSOG-UHFFFAOYSA-N naphthalen-1-ylsulfonyloxymethyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(OCOS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 LCRMGUFGEDUSOG-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 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
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 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
- 239000008262 pumice Substances 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 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
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 150000003512 tertiary amines Chemical class 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
- 229930192474 thiophene Natural products 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
- 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
- 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
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-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
- 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
- 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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
4-Anilino-pyrimidin-Derivate sind bekannt als wirksame Komponenten in fungiziden Mitteln (vergl. z. B. JP 01/093575, JP 63/238068, DE 36 44 799, EP 2 48 349, DE 36 18 353, JP 58/198472; J. Environ. Sci. Health, Part B, B 18(4-5), (1983), S. 599-610; DE 32 05 638, JP 54/147921, Indian. J. Chem. Sect. B, 16B(10), (1978), S. 932-3; DE 26 54 090, GB 13 94 817; Boll. Chim. Farm., 105(9), (1966), S. 660-5).4-anilino-pyrimidine derivatives are known to be effective components in fungicidal compositions (see e.g. JP 01/093575, JP 63/238068, DE 36 44 799, EP 2 48 349, DE 36 18 353, JP 58/198472; J. Environ. Sci. Health, Part B, B 18 (4-5), (1983) pp 599-610; DE 32 05 638, JP 54/147921, Indian. J. Chem. Sect. B, 16B (10), (1978), pp. 932-3; DE 26 54 090, GB 13 94 817; Boll. Chim. Farm., 105 (9), (1966), pp. 660-5).
Es gibt allerdings nur sehr wenige Hinweise auf Verbindungen, die in der 2-Position des Pyrimidins Reste mit Dreifachbindungen tragen, beispielsweise ist ein 2,3-Dimethylphenyl-4-aminopyridin beschrieben (US 39 74 162).However, there is very little evidence of connections in the 2 position of the Wear pyrimidine residues with triple bonds, for example is a 2,3-Dimethylphenyl-4-aminopyridine described (US 39 74 162).
Außerdem ist die mikrobiocide Wirkung von Nitrophenyl-Derivaten (EP 1 39 613, GB 21 37 991) bekannt.In addition, the microbiocidal action of nitrophenyl derivatives (EP 1 39 613, GB 21 37 991) known.
Die Wirkung dieser Derivate ist jedoch - insbesondere bei niedrigen Aufwandmengen - nicht immer befriedigend, häufig ist auch das Artenspektrum nicht ausreichend. Außerdem ist eine Schädigung der Nutzpflanzen durch diese Derivate möglich.However, the effect of these derivatives is not - especially when the application rates are low always satisfactory, often the spectrum of species is not sufficient. Besides, one is Damage to crops possible through these derivatives.
Es wurden neue 4-Anilino-pyrimidin-Derivate gefunden, die vorteilhafte Wirkungen bei der Bekämpfung eines breiten Spektrums phytopatogener Pilze, insbesondere bei niedrigen Dosierungen, aufweisen und keine Schädigung von Nutzpflanzen verursachen. New 4-anilino-pyrimidine derivatives have been found which have advantageous effects in the Control of a wide range of phytopatogenic fungi, especially low ones Dosages, and do not cause damage to crops.
Gegenstand der vorliegenden Erfindung sind daher Verbindungen der Formel I,The present invention therefore relates to compounds of the formula I
worin
R¹, R² = unabhängig voneinander Wasserstoff, (C₁-C₉)Alkyl, Cyano-(C₁-C₄)alkyl,
Halo-(C₁-C₄)alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl,
(C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl,
Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl,
(C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl,
(C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach
durch (C₁-C₄)Alkyl substituiert sein können, gegebenenfalls substituierter 5- oder
6gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls
substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl,
gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester,
(C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl,
(C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und
Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert
bedeuten kann,
R¹ und R² gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10
Ringgliedern,
R³ = Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl,
Cyano-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl,
Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio,
Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl,
(C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl,
(C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach
durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl,
(C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl,
(C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl,
(C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls
substituierter 5- oder 6gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl,
gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes
Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl,
gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls
substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester,
(C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl,
(C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und
Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert
bedeuten kann.
R⁴, R⁵, R⁶ = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano,
Thiocyano, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylamino,
(C₁-C₄)Dialkylamino, (C₁-C₄)Alkylcarbonylamino, Halo-(C₁-C₄)alkyl,
Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl,
Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio,
Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl,
(C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl,
(C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach
durch (C₁-C₄)Alkyl substituiert sein können,
(C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl,
(C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl,
(C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Haloalkoxycarbonyl, (C₁-C₄)Alkylthiocarbonyl,
(C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl,
(C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls substituierter 5- oder 6gliedriger
Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes
Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls
substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl,
gegebenenfalls substituiertes Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls
substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenyl (Heteroaromat) bis zu dreifach durch Halogen, Ester,
(C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl,
(C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und
Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert
bedeuten kann,
R⁴, R⁵ und/oder R⁶ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder
aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder
P mit 4 bis 10 Ringgliedern,
R⁷ = Wasserstoff, Formyl, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Halo-(C₁-C₄)alkoxy,
Amino(C₁-C₄)alkoxy, (C₁-C₄)Alkylamino(C₁-C₄)alkoxy,
(C₁-C₄)Alkoxy(C₁-C₄)alkoxy, Amino, (C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino,
Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, Cyano-(C₁-C₄)alkyl,
Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl,
(C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl,
(C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl,
(C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl,
(C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die
cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können,
(C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl,
(C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl,
(C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl,
(C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl,
(C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls
substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl,
gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenylteil bis zu dreifach durch Halogen, Ester (C₁-C₄)Alkyl,
(C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder
einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten
ein- oder mehrfach durch Halogenatome substituiert sein kann,
R⁷ und R⁴ und/oder R⁵ gegebenfalls zusammen einen gesättigten, oder teilweise
ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder
P mit 4 bis 10 Ringgliedern,
R⁸, R⁹ = unabhängig voneinander Wasserstoff, Halogen, (C₁-C₄)Alkyl,
Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, Cyano-(C₁-C₄)alkyl,
Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl,
Halo-(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio,
Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl,
(C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-, (C₁-C₄)Dialkylamino-,
(C₃-C₉)Cycloalkylamino-, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl,
(C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach
durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl,
(C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl,
(C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl,
(C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls
substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls
substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl,
gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl,
(C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder
einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten
ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁸ und R⁹ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder
aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder
P mit 4 bis 10 Ringgliedern,
X = Sauerstoff oder Schwefel und
n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze.wherein
R¹, R² = independently of one another hydrogen, (C₁-C₉) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl , (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo- (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄ ) Alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl , where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C ) alkyl, optionally substituted phenylamino (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester, (C₁- C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents one or more times can be substituted by halogen atoms,
R¹ and R² optionally together a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R³ = hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄) alkyl, ( C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio, halo- (C₁-C₄ ) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl , (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁- C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄ ) Haloalkoxycarbonyl, (C₁-C₄) alkylthio carbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part (heteroaromatic) is up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁- C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the sub can be substituted one or more times by halogen atoms.
R⁴, R⁵, R⁶ = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) Alkylamino, (C₁-C₄) dialkylamino, (C₁-C₄) alkylcarbonylamino, halo- (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio- (C₁- C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄ ) Dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) Heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁ -C₄) alkyl, (C ₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁ -C₄) haloalkoxycarbonyl, (C₁-C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenoxy, optionally substituted phenoxy , optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- ( C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl (heteroaromatic) up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano may mean halo in the substituents substituted one or more times by halogen atoms,
R⁴, R⁵ and / or R⁶ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R⁷ = hydrogen, formyl, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, halo- (C₁-C₄) alkoxy, amino (C₁-C₄) alkoxy, (C₁-C₄) alkylamino (C₁-C₄) alkoxy, (C₁-C₄) alkoxy (C₁-C₄) alkoxy, amino, (C₁-C₄) alkylamino, (C₁-C₄) dialkylamino, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- ( C₁-C₄) alkyl, halo (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio , Halo (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂- C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉ ) Cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, ( C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C -C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) haloalkoxycarbonyl, (C₁- C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄ ) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino - (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, where optionally substituted is to be understood that the phenyl moiety up to three times by halogen, ester (C₁-C₄) alkyl, (C₁-C₄) alkoxy , (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can be substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁷ and R⁴ and / or R⁵ optionally together a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R⁸, R⁹ = independently of one another hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄ ) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo- (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- ( C₁-C₄) alkylthio, halo (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino-, (C₁-C₄) dialkylamino-, (C₃-C₉) cycloalkylamino-, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl , where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁- C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C -C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) haloalkoxycarbonyl, (C₁-C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, ( C₁-C₄) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo - (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply by nitro ode r cyano can be substituted, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁸ and R⁹ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
X = oxygen or sulfur and
n = a number from 0 to 8, and their acid addition salts.
In Formel I bedeuten
R¹, R² bevorzugt unabhängig voneinander Wasserstoff, (C₁-C₉)Alkyl, im Phenylteil durch
Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenyl,
insbesondere Wasserstoff oder (C₁-C₄)Alkyl, besonders bevorzugt Wasserstoff,
R¹ und R² können zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder
Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,
insbesondere mit 5 oder 6 Ringgliedern bilden, und
R³ bedeutet bevorzugt Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl,
Dihydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl,
(C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl,
(C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die
cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können,
gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy,
gegebenenfalls substituierter 5- bis 6gliedriger Heteroaromat, beispielsweise Pyridin,
Thiophen, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil
(Heteroaromat) bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy,
(C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro
oder Cyano substituiert sein kann.
R³ bedeutet insbesondere Wasserstoff oder Halogen, besonders bevorzugt Wasserstoff,
R⁴, R⁵, R⁶ bedeuten bevorzugt unabhängig voneinander Wasserstoff, Halogen, Hydroxy,
Amino, Nitro, Cyano, Thiocyano, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy,
(C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, Halo-(C₁-C₄)alkyl, Hydroxy-(C₁-C₄)alkyl,
(C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio,
Halo-(C₁-C₄)alkylthio, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl,
(C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl,
(C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach
durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl,
(C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkoxycarbonyl,
(C₁-C₄)Alkoxycarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl,
gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy,
gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, wobei unter gegebenenfalls
substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester,
(C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl,
(C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann.
R⁴, R⁵ und/oder R⁶ können zusammen einen gesättigten, teilweise ungesättigten oder
aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit
4 bis 10 Ringgliedern bilden.
R⁴, R⁵, R⁶ bedeuten insbesondere unabhängig voneinander Wasserstoff, Halogen,
(C₁-C₄)Alkyl, (C₁-C₄)Alkoxy oder im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder
(C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenoxy, besonders bevorzugt
Wasserstoff, Cl, F oder OCH₃,
R⁷ bedeutet bevorzugt Wasserstoff, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy,
Halo-(C₁-C₄)alkoxy, Amino(C₁-C₄)alkoxy, (C₁-C₄)Alkylamino(C₁-C₄)alkoxy,
(C₁-C₄)Alkoxy(C₁-C₄)alkoxy, Amino, (C₁-C₄)Alkylamino,
(C₁-C₄)Alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Perhalo-(C₁-C₄)alkylthio,
(C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei
die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können,
(C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl,
(C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls
substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, wobei
unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach
durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio,
(C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano
substituiert sein kann.
R⁷ und R⁴ und/oder R⁵ können zusammen einen gesättigten, teilweise ungesättigten
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10
Ringgliedern bilden.
R⁷ bedeutet insbesondere Wasserstoff oder (C₁-C₄)Alkyl, besonders bevorzugt Wasserstoff.
R⁸, R⁹ sind bevorzugt unabhängig voneinander Wasserstoff, Halogen, (C₁-C₄)Alkyl,
Hydroxy-(C₁-C₄)alkyl, Perhalo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy,
(C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio,
(C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl,
(C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, (C₃-C₉)Cycloalkylamino,
(C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl,
(C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl,
(C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die
cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können,
(C₁-C₄)Alkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl,
gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes
Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist,
daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl,
(C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder
einfach durch Nitro oder Cyano substituiert sein kann.
R⁸ bedeutet insbesondere Wasserstoff, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Phenyl-(C₁-C₄)alkoxy
oder Halogen, besonders bevorzugt Wasserstoff, Cl oder OCH₃.
R⁸ und R⁹ können zusammen einen gesättigten, teilweise ungesättigten oder aromatischen
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10
Ringgliedern bilden.
R⁹ bedeutet insbesondere Wasserstoff, (C₁-C₄)Alkyl, Perhalo-(C₁-C₄)alkyl,
(C₁-C₄)Alkoxy-(C₁-C₄)alkyl oder Phenyl-(C₁-C₄)alkyl, besonders bevorzugt
Wasserstoff oder CH₃.
X ist bevorzugt Sauerstoff oder Schwefel und
n ist eine Zahl von 0 bis 4, insbesondere 0 oder 1, besonders bevorzugt 0.In formula I mean
R¹, R² preferably independently of one another hydrogen, (C₁-C₉) alkyl, in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenyl, in particular hydrogen or (C₁-C₄) alkyl, particularly preferably hydrogen ,
R¹ and R² together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members, in particular with 5 or 6 ring members, and
R³ is preferably hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, (C₂-C₆) alkenyl, (C₂-C₆ ) Alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) Cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, optionally substituted Phenyl, optionally substituted phenoxy, optionally substituted 5- to 6-membered heteroaromatic, for example pyridine, thiophene, where optionally substituted is understood to mean that the phenyl part (heteroaromatic) up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁ -C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano.
R³ means in particular hydrogen or halogen, particularly preferably hydrogen,
R⁴, R⁵, R⁶ are preferably independently hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄ ) Alkylamino, (C₁-C₄) dialkylamino, halo (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo (C₁-C₄) alkylthio, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl , (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄ ) Alkoxycarbonyl, (C₁-C₄) alkoxycarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, optionally substituted phenyl, optionally substituted pheno xy, optionally substituted phenylketo (C₁-C₄) alkyl, where optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄ ) Alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano.
R⁴, R⁵ and / or R⁶ together can form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
R⁴, R⁵, R⁶ mean in particular independently of one another hydrogen, halogen, (C₁-C₄) alkyl, (C₁-C₄) alkoxy or in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenoxy, especially preferably hydrogen, Cl, F or OCH₃,
R⁷ preferably denotes hydrogen, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, halo- (C₁-C₄) alkoxy, amino (C₁-C₄) alkoxy, (C₁-C₄) Alkylamino (C₁-C₄) alkoxy, (C₁-C₄) alkoxy (C₁-C₄) alkoxy, amino, (C₁-C₄) alkylamino, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio , Perhalo (C₁-C₄) alkylthio, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁ -C₄) alkylcarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo- (C₁-C₄) alkyl, where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C ) Alkylthio, (C₁-C₄) haloalkyl, (which may be C₁-C₄) haloalkoxy or monosubstituted by nitro or cyano.
R⁷ and R⁴ and / or R⁵ together can form a saturated, partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
R⁷ means in particular hydrogen or (C₁-C₄) alkyl, particularly preferably hydrogen.
R⁸, R⁹ are preferably independently of one another hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, perhalo- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino, (C₁-C₄) dialkylamino, (C₃-C₉) cycloalkylamino, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- ( C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁ -C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenoxyphenyl- ( C₁-C₄) alkyl, wherein optionally substituted is to be understood that de r phenyl moiety up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply by nitro or cyano can be substituted.
R⁸ means in particular hydrogen, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, phenyl- (C₁-C₄) alkoxy or halogen, particularly preferably hydrogen, Cl or OCH₃.
R⁸ and R⁹ together can form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
R⁹ means in particular hydrogen, (C₁-C₄) alkyl, perhalo (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl or phenyl- (C₁-C₄) alkyl, particularly preferably hydrogen or CH₃.
X is preferably oxygen or sulfur and n is a number from 0 to 4, in particular 0 or 1, particularly preferably 0.
Unter Halo ist in den einzelnen Substituenten ein- oder mehrfach durch Halogenatome substituiert zu verstehen.Halo is in the individual substituents one or more times by halogen atoms to understand substituted.
Zur Herstellung der Säureadditionssalze der Verbindungen der Formel I kommen folgende Säuren in Frage: Halogenwasserstoffsäuren wie Chlorwasserstoffsäure oder Bromwasserstoffsäure, Phosphorsäure, Salpetersäure, Schwefelsäure, mono- oder bifunktionelle Carbonsäuren und Hydroxycarbonsäuren wie Essigsäure, Maleinsäure, Bernsteinsäure, Fumarsäure, Weinsäure, Citronensäure, Salicylsäure, Sorbinsäure oder Milchsäure, sowie Sulfonsäuren wie p-Toluolsulfonsäure oder 1,5-Naphthalindisulfonsäure. Die Säureadditionsverbindungen der Formel I können in einfacher Weise nach den üblichen Salzbildungsmethoden, z. B. durch Lösen einer Verbindung der Formel I in einem geeigneten organischen Lösungsmittel und Hinzufügen der Säure erhalten werden und in bekannter Weise, z. B. durch Abfiltrieren, isoliert und gegebenenfalls durch Waschen mit einem inerten organischen Lösungsmittel gereinigt werden.The following are used to prepare the acid addition salts of the compounds of the formula I. Acids in question: hydrohalic acids such as hydrochloric acid or Hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, Succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or Lactic acid and sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula I can be prepared in a simple manner according to the usual Salt formation methods, e.g. B. by dissolving a compound of formula I in a suitable organic solvents and adding the acid can be obtained and in known Way, e.g. B. by filtering, isolated and optionally by washing with an inert organic solvents can be cleaned.
Die Pyrimidine der Formel I können nach verschiedenen mehrstufigen Verfahren hergestellt werden.The pyrimidines of the formula I can be prepared by various multistage processes will.
Man erhält die erfindungsgemäßen Verbindungen, indem man Verbindungen der Formel IIThe compounds of the invention are obtained by using compounds of the formula II
worin Hal = Cl oder Br und R¹² = (C₁-C₄)Alkylthio, im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenyl(C₁-C₄)alkylthio oder den Rest IIIwherein Hal = Cl or Br and R¹² = (C₁-C₄) alkylthio, in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenyl (C₁-C₄) alkylthio or the rest III
bedeuten, mit Verbindungen der Formel IVmean with compounds of formula IV
umsetzt und, falls R¹² eine von der Formel III abweichende Bedeutung hat, anschließend die erhaltenen Verbindungen im Rest R¹² oxidiert und die entstandenen Oxidationsprodukte mit Verbindungen der Formel Vimplemented and, if R¹² has a different meaning from the formula III, then the Compounds obtained in the rest R¹² oxidized and the resulting oxidation products with Compounds of formula V
zu den Endprodukten der Formel I mit R¹² = Rest der Formel III umsetzt sowie gegebenenfalls, wenn R³ = H, den Wasserstoff gegen Halogen in bekannter Weise austauscht.to the end products of formula I with R¹² = radical of formula III and optionally, when R³ = H, the hydrogen against halogen in a known manner exchanges.
Die Ausgangsstoffe der Formel I erhält man nach einer Anzahl literaturbekannter Verfahren.The starting materials of formula I are obtained by a number of processes known from the literature.
Durch Kondensation geeigneter 3-Ketocarbonsäureester mit Thioharnstoff oder S-alkylierten Thioharnstoffen, wobei sie in reiner Form oder in situ, aus ihren Salzen freigesetzt, eingesetzt werden können, ohne Lösungsmittel oder in einem geeigneten aprotischen oder protischen Lösungsmittel (Wasser, niedere Alkohole), bei Temperaturen von 0°C bis 160°C, bevorzugt bei Temperaturen zwischen Raumtemperatur und der Siedetemperatur des Lösungsmittels, in Gegenwart einer geeigneten Base, wie Alkalicarbonate (Na₂CO₃ oder K₂CO₃) oder Alkalialkoholate (NaOMe oder NaOEt), zu entsprechenden 4-Pyrimidinonen.By condensation of suitable 3-ketocarboxylic acid esters with thiourea or S-alkylated Thioureas, used in pure form or in situ, released from their salts can be without solvent or in a suitable aprotic or protic Solvents (water, lower alcohols), at temperatures from 0 ° C to 160 ° C, preferred at temperatures between room temperature and the boiling point of the solvent, in Presence of a suitable base, such as alkali carbonates (Na₂CO₃ or K₂CO₃) or Alkaline alcoholates (NaOMe or NaOEt), to corresponding 4-pyrimidinones.
R¹⁰ steht in diesem und in den folgenden Formelschemata für S,S-(C₁-C₄)Alkyl, im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes S-(C₁-C₄)Alkyl-phenyl.R¹⁰ is in this and in the following formula schemes for S, S- (C₁-C₄) alkyl, in Phenyl part optionally substituted by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy S- (C₁-C₄) alkyl phenyl.
Die Verfahren sind in der Literatur bekannt, die Edukte sind käuflich oder können nach literaturbekannten Verfahren (z. B. Beilstein 3./4. Ergänzungswerk, Band 25, S. 50, S. 472) hergestellt werden. The processes are known in the literature, the starting materials are commercially available or can be processes known from the literature (e.g. Beilstein 3rd / 4th supplement, volume 25, p. 50, p. 472) getting produced.
Für die Herstellung der Pyrimidine der Formel II mit R⁸ = Halogen ist die Umsetzung geeigneter 4-Pyrimidinone mit elementaren Halogenen in einem aprotischen oder protischen Lösungsmittel wie Essigsäure bevorzugten (Beilstein, 3./4. Ergänzungswerk, Band 25, S. 56).The reaction is for the preparation of the pyrimidines of the formula II with R⁸ = halogen suitable 4-pyrimidinones with elemental halogens in an aprotic or protic Preferred solvents such as acetic acid (Beilstein, 3rd / 4th supplement, volume 25, p. 56).
R¹¹ steht in diesem und in den folgenden Formelschemata für (C₁-C₄)Alkyl oder im Phenylteil durch Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy oder im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes (C₁-C₄)Alkyl-phenyl oderR¹¹ is in this and in the following formula schemes for (C₁-C₄) alkyl or in Phenyl part by halogen, (C₁-C₄) alkyl, (C₁-C₄) alkoxy or in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted (C₁-C₄) alkylphenyl or
Verbindungen der Formel II mit R⁹ = Wasserstoff können in Ablehnung an entsprechende Literaturvorschriften (Beilstein, 3./4. Ergänzungswerk, Band 25, S. 279) 2stufig in einem Eintopfverfahren hergestellt werden. Zunächst werden in einem inerten Lösungsmittel wie Toluol, THF, Dioxan oder Diethylether entsprechende Carbonsäurederivate mit einer geeigneten Base, zumeist einem Alkalihydrid (NaH) oder Alkalialkoholat (NaOMe) anionisiert und dann mit einem Ameisensäureester formyliert.Compounds of formula II with R⁹ = hydrogen can be rejected to corresponding Literature regulations (Beilstein, 3rd / 4th supplement, volume 25, p. 279) in two stages in one One-pot processes can be produced. First, like in an inert solvent Toluene, THF, dioxane or diethyl ether corresponding carboxylic acid derivatives with a suitable base, usually an alkali hydride (NaH) or alkali alcoholate (NaOMe) anionized and then formylated with a formic acid ester.
Die anschließende Kondensation kann mit Thioharnstoff oder S-alkylierten Thioharnstoffen erfolgen, wobei diese in reiner Form oder in situ, mittels Basen (Alkoholate wie NaOMe) aus ihren Salzen freigesetzt, eingesetzt werden können. Als besonders für die Kondensation geeignet haben sich protische Lösungsmittel, insbesondere niedere Alkohole, erwiesen.The subsequent condensation can be with thiourea or S-alkylated thioureas take place, these in pure form or in situ, using bases (alcoholates such as NaOMe) released their salts, can be used. As especially for the condensation Protic solvents, in particular lower alcohols, have proven suitable.
Die Modifizierung bekannter Pyrimidinone oder Mercaptopyrimdinone erfolgt mit einem Alkylierungsmittel, wie Alkylhalogenide (z. B. Methyljodid) oder Alkylsäureester (z. B. Dimethylsulfat, Phosphorsäuretrimethylester), insbesondere Propinylhalogenide, unter Verwendung einer Base wie NaOH, NaH oder Triethylamin in einem geeigneten protischen oder aprotischen Lösungsmittel (DMF, Acetonitril, Wasser) bei Temperaturen von 0°C bis 260°C, bevorzugt im Temperaturbereich von 50°C bis zu der Siedetemperatur des Lösungsmittels.Known pyrimidinones or mercaptopyrimdinones are modified with a Alkylating agents such as alkyl halides (e.g. methyl iodide) or alkyl acid esters (e.g. Dimethyl sulfate, phosphoric acid trimethyl ester), especially propynyl halides, under Use a base such as NaOH, NaH or triethylamine in a suitable protic or aprotic solvents (DMF, acetonitrile, water) at temperatures from 0 ° C to 260 ° C, preferably in the temperature range from 50 ° C to the boiling point of Solvent.
Die so erhaltenen 4-Pyrimidinone können mit überschüssigem POCl₃ (POBr₃) ohne Lösungsmittel, in einem gegen POCl₃ (POBr₃) inerten Lösungsmittel oder in einem basischen Lösungsmittel wie DMF ohne oder mit einem Säurefänger, wie N,N-Dimethylanilin in 0,001 bis 2 Moläquivalenten, vorzugsweise 0,02 Äquivalenten, bei Temperaturen von 50°C bis 110°C, vorzugsweise bei der Siedetemperatur des POCl₃ (POBr₃) in die entsprechenden 4-Halogenpyrimidine überführt werden (vergl. Beilstein, Hauptwerk, Band 25, S. 372, Beilstein, 3./4. Ergänzungswerk, Band 23, S. 2471).The 4-pyrimidinones thus obtained can with excess POCl₃ (POBr₃) without Solvent, in a solvent inert to POCl₃ (POBr₃) or in one basic solvents such as DMF without or with an acid scavenger, such as N, N-dimethylaniline in 0.001 to 2 molar equivalents, preferably 0.02 equivalents Temperatures from 50 ° C to 110 ° C, preferably at the boiling point of POCl₃ (POBr₃) are converted into the corresponding 4-halopyrimidines (cf. Beilstein, Hauptwerk, volume 25, p. 372, Beilstein, 3./4. Supplement, volume 23, p. 2471).
Die Aniline der Formel IV sind größtenteils bekannte Verbindungen bzw. können in analoger, dem Fachmann geläufiger Weise hergestellt werden.The anilines of the formula IV are mostly known compounds or can in can be produced in a manner analogous to those skilled in the art.
Die Umsetzung von II mit IV erfolgt in Abhängigkeit von der Reaktivität der Derivate in einem inerten Lösungsmittel (Wasser/Aceton, Toluol, THF) bei Temperaturen von 0°C bis 150°C, vorzugsweise von 50°C bis 100°C. Der Austausch kann durch katalytischen bis äquimolaren Basenzusatz begünstigt werden, im allgemeinen hat es sich jedoch als vorteilhaft erwiesen, die Reaktion mit Säure, insbesondere mit Salzsäure, zu katalysieren.The reaction of II with IV takes place depending on the reactivity of the derivatives in an inert solvent (water / acetone, toluene, THF) at temperatures from 0 ° C to 150 ° C, preferably from 50 ° C to 100 ° C. The exchange can be catalytic up equimolar base addition are favored, but in general it has proven to be proven to catalyze the reaction with acid, especially with hydrochloric acid.
Ist R¹² ein Rest mit einer Dreifachbindung, so findet die erwartete Addition des Anilin an die Dreifachbindung nicht statt.If R¹² is a radical with a triple bond, the expected addition of the aniline to the Triple binding does not take place.
Sofern die zur Synthese der erfindungsgemäßen Verbindungen benötigten, den Rest -CR¹R²-(CH₃)n-C≡CR³ enthaltenden Pyrimidin-Derivate der Formel II nicht zur Verfügung stehen, kann man diesen Rest nachträglich in die zunächst erhaltenen Umsetzungsprodukte von II (mit R¹² = Rest der Formel III) und IV einführen. Hierzu kann bei entsprechenden 2-Alkylmercaptopyrimidinen die schwefeltragende Gruppe oxidiert werden. Die Oxidation kann nach üblichen Verfahren mit geeigneten Oxidationsmitteln, wie Peroxide (z. B. H₂O₂), Permanganat, Perbenzoesäuren, oder mit einem Gemisch aus Kaliumperoxomonosulfat, 2 KHSO₅, KHSO₄, und K₂SO₄ in einem Lösungsmittel oder Lösungsmittelgemisch (z. B. Wasser, Essigsäure, Methanol) oxidiert werden (vergl. Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3, S. 96; D. J. Brown, B. T. England; J. Chem. Soc.(C), (1971), S. 256). Die Oxidation kann auch mittels Katalysatoren gestartet oder beschleunigt werden.If the pyrimidine derivatives of the formula II which are required for the synthesis of the compounds according to the invention and contain the radical -CR¹R²- (CH₃) n -C≡CR³ are not available, this radical can subsequently be converted into the reaction products of II (with R¹² = Introduce the rest of the formula III) and IV. For this purpose, the sulfur-bearing group can be oxidized with corresponding 2-alkylmercaptopyrimidines. The oxidation can be carried out by customary methods using suitable oxidizing agents, such as peroxides (e.g. H₂O₂), permanganate, perbenzoic acids, or using a mixture of potassium peroxomonosulfate, 2 KHSO₅, KHSO₄, and K₂SO₄ in a solvent or solvent mixture (e.g. water, Acetic acid, methanol) are oxidized (see Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3, p. 96; DJ Brown, BT England; J. Chem. Soc. ( C), (1971), p. 256). The oxidation can also be started or accelerated using catalysts.
In diesem oder den weiteren Formelschemata steht R¹³ für Halogen, inbesondere für Chlor, oder fürIn this or the other formula schemes, R 13 represents halogen, in particular chlorine, or for
Im nächsten Schritt kann der Austausch der Sulfonylgruppe gegen Alkohole erfolgen. In Abhängigkeit von der Reaktivität der Derivate kann man in einem inerten Lösungsmittel (Toluol, THF) bei 0°C bis 150°C, im allgemeinen bei 25°C bis 50°C, arbeiten, wobei die Sulfonylgruppe gegen Alkolate der entsprechenden Alkinole, hergestellt aus dem entsprechenden Alkinol und einer Base, im allgemeinen NaH, austauschen. Hierbei sind zur Vermeidung von Nebenreaktionen, insbesondere für Verbindungen der Formel I mit R¹³=Halogen, möglichst niedrige Temperaturen anzustreben; auch sollte ein Überschuß an Alkoholat vermieden werden. Der Austausch von Sulfonylmethylgruppen bei Pyrimidinen ist bekannt (Vergl. Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3, S. 97), die Anwendung der Reaktion auf hier beschriebene Systeme dagegen ist neu.In the next step, the sulfonyl group can be exchanged for alcohols. In Depending on the reactivity of the derivatives, one can in an inert solvent (Toluene, THF) at 0 ° C to 150 ° C, generally at 25 ° C to 50 ° C, the Sulfonyl group against alkolates of the corresponding alkynols, prepared from the exchange the corresponding alkinol and a base, generally NaH. Here are for Avoidance of side reactions, in particular for compounds of the formula I where R 13 = halogen, to strive for the lowest possible temperatures; also should be a surplus Alcoholate should be avoided. The exchange of sulfonylmethyl groups in pyrimidines is known (see Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3, p. 97), the application of the reaction to The systems described here are new.
Wie bereits beschrieben, kann für den Fall, daß R¹³ = Halogen ist, das Halogen anschließend gegen Anilin ausgetauscht werden.As already described, in the event that R 13 = halogen, the halogen can subsequently be exchanged for aniline.
Als Beispiel für eine weitere Modifizierung von Edukten zur Herstellung von Verbindungen der Formel I sei die Halogenierung der Alkinylfunktion genannt. In Abwandlung literaturbekannter Methoden ("Alkine, Di- und Polyine, Allene, Kumulene", Methoden der organischen Chemie (Houben/Weyl) Thieme-Verlag, 1977, Band 5, 2a, Stuttgart, S. 600 ff.) kann in einem geeigneten aprotischen Lösungsmittel, wie THF oder Dioxan, mit Basen, wie n-Butyllithium, das terminale Proton des Ethinyl-Derivates abstrahiert und anschließend ein Halogen, beispielsweise Jod oder Brom, eingeführt werden.As an example for a further modification of starting materials for the production of compounds Formula I is the halogenation of the alkynyl function. In a variation methods known from the literature ("Alkynes, Di- und Polyine, Allene, Kumulene", methods of organic chemistry (Houben / Weyl) Thieme-Verlag, 1977, volume 5, 2a, Stuttgart, p. 600 ff.) can in a suitable aprotic solvent, such as THF or dioxane, with bases, such as n-butyllithium, which abstracts the terminal proton of the ethynyl derivative and then one Halogen, for example iodine or bromine, are introduced.
In diesem Beispiel steht dann R³ für X, stellvertretend für Halogen, insbesondere für Brom oder Jod.In this example, R³ then stands for X, which represents halogen, in particular bromine or iodine.
Die erfindungsgemäßen Verbindungen der Formel I können zum Schutz verschiedener Kulturpflanzen gegen pathogene Mikroorganismen, insbesondere Fungi, eingesetzt werden, wobei sie sich durch besonders hohe Kulturpflanzenverträglichkeit auszeichnen. Sie besitzen vorteilhafte präventive oder systemische Eigenschaften. Bereits in das pflanzliche Gewebe eingedrungene pilzliche Krankheitserreger lassen sich auch erfolgreich kurativ bekämpfen. Durch Besprühen, Bestäuben oder andere Applikationen mit Wirkstoffen der Formel I können Pflanzen und bestehende oder zuwachsende Pflanzenteile vor auftretenden Schädlingen geschützt werden. Sie eignen sich auch als Beizmittel zur Behandlung von Saatgut und Stecklingen zum Schutz vor Pilzinfektionen sowie im Erdboden auftretende pathogene Pilze. Das Wirkungsspektrum der beanspruchten Verbindungen umfaßt eine Vielzahl verschiedener wirtschaftlich bedeutender, phytopathogener Pilze, wie Alternaria mali, Botrytis cinerea, Benzimidazol- und/oder Dicarboximid-sensible und resistente Stämme, Sclerotinia sclerotinorum sowie weitere Grauschimmelarten, Cercospora beticola, Ceratobasidium cerealis, Erysiphe graminis, Erysiphe graminis, hordei, Erysiphe chichoracearum sowie andere Echte Mehltauarten, Fusarium culmorum und andere Fusariumarten, Moniliniaarten, Leptosphaeria nodorum sowie andere Septoriaarten und Blattfleckenverursachende Arten, Pellicularia sasakii, Piricularia oryzae und andere Reispilzarten, Phytophthora infestans, Phytophtora capsici und verschiedene andere Kraut- und Knollenfäulepilze, Plasmopara viticola, Pseudopernospora cubensis und weitere Pernospora oder Falsche Mehltauarten, Pseudocercosporella herpotrichoides und verschiedene andere Augenflecken bzw. Halmbruch verursachende Pilzarten, Puccinia recondita und verschiedene andere Rostpilze, Pyrenophora teres und andere Drechslerarten, Ustilagoarten, Venturia inaequalis und Schorfarten, wobei jedoch die Wirkung gegen Ascomyceten und Deuteromyceten und insbesondere gegen BCM-resistente Pseudocercosporella herpotrichoides-Stämme hervorzuheben ist.The compounds of formula I according to the invention can protect various Crop plants against pathogenic microorganisms, in particular fungi, are used, whereby they are characterized by a particularly high crop tolerance. they have advantageous preventive or systemic properties. Already in the vegetable Tissue-infested pathogens can also be successfully curated fight. By spraying, dusting or other applications with active ingredients of Formula I can plants and existing or growing parts of plants before occurring Pests are protected. They are also suitable as a mordant for the treatment of Seeds and cuttings to protect against fungal infections and those occurring in the ground pathogenic fungi. The spectrum of action of the claimed compounds includes one Variety of different economically important phytopathogenic mushrooms, such as Alternaria mali, botrytis cinerea, benzimidazole and / or dicarboximide sensitive and resistant Strains, Sclerotinia sclerotinorum and other gray mold species, Cercospora beticola, Ceratobasidium cerealis, Erysiphe graminis, Erysiphe graminis, hordei, Erysiphe chichoracearum and other powdery mildew species, Fusarium culmorum and others Fusarium species, Moniliniaarten, Leptosphaeria nodorum as well as other Septoriaarten and Leaf blotch causing species, Pellicularia sasakii, Piricularia oryzae and others Rice mushroom species, Phytophthora infestans, Phytophtora capsici and various other herb and tuber rot fungi, Plasmopara viticola, Pseudopernospora cubensis and others Pernospora or downy mildew species, Pseudocercosporella herpotrichoides and various other eye spots or stalks causing fungus, Puccinia recondita and various other rust fungi, Pyrenophora teres and other types of turner, Ustilagoarten, Venturia inaequalis and scab species, however, the effect against Ascomycetes and Deuteromycetes and especially BCM-resistant Pseudocercosporella herpotrichoides strains should be emphasized.
Die erfindungsgemäßen Verbindungen eignen sich daneben auch für den Einsatz in technischen Bereichen, beispielsweise als Holzschutzmittel, als Konservierungsmittel in Anstrichfarben, in Kühlschmiermittel für die Metallbearbeitung oder als Konservierungsmittel in Bohr- und Schneidölen.The compounds of the invention are also suitable for use in technical areas, for example as a wood preservative, as a preservative in Paints, in cooling lubricants for metalworking or as Preservative in drilling and cutting oils.
Gegenstand der Erfindung sind auch Mittel, die die Verbindungen der Formel I neben geeigneten Formulierungshilfsmitteln enthalten. Die erfindungsgemäßen Mittel enthalten die Wirkstoffe der Formel I im allgemeinen zu 1 bis 95 Gew.-%.The invention also relates to agents which in addition to the compounds of the formula I. contain suitable formulation aids. The agents according to the invention contain the Active ingredients of formula I in general from 1 to 95 wt .-%.
Sie können auf verschiedene Art formuliert werden, je nachdem wie es durch die biologischen und chemisch-physikalischen Parameter vorgegeben ist. Als Formulierungsmöglichkeiten kommen daher in Frage: Spritzpulver (WP), emulgierbare Konzentrate (EC), wäßrige Dispersionen auf Öl- oder Wasserbasis (SC), Suspoemulsionen (SC), Stäubemittel (DP), Beizmittel, Granulate in Form von wasserdispergierbaren Granulaten (WG), ULV-Formulierungen, Mikrokapseln, Wachse oder Köder.They can be formulated in different ways, depending on how it is done by the biological and chemical-physical parameters is specified. As Formulation options are therefore possible: wettable powder (WP), emulsifiable Concentrates (EC), aqueous dispersions based on oil or water (SC), suspo emulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible Granules (WG), ULV formulations, microcapsules, waxes or baits.
Diese einzelnen Formulierungstypen sind bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N. Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.These individual types of formulation are known and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carrier", 2nd Ed., Darland Books, Caldwell N. J.; H. v. Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed. J. Wiley & Sons, N. Y.; Marschen, "Solvents Guide", 2nd Ed., Interscience, N. Y. 1950; Mc Cutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp. Ridgewood, N. J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N. Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsges., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986.The necessary formulation aids such as inert materials, surfactants, solvents and further additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carrier," 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed. J. Wiley & Sons, N. Y .; March, Solvents Guide, 2nd Ed., Interscience, N.Y. 1950; Mc Cutcheon's, "Detergents and Emulsifiers Annual," MC Publ. Corp. Ridgewood, N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Surface-active ethylene oxide adducts", Wiss. Verlagsges., Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, Düngemitteln und/oder Wachstumsregulatoren herstellen, z. B. in Form einer Fertigformulierung oder als Tankmix.On the basis of these formulations, combinations with other pesticides can also be made manufacture effective substances, fertilizers and / or growth regulators, e.g. B. in the form of a finished formulation or as a tank mix.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Netzmittel, z. B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenyl-sulfonate und Dispergiermittel, z. B. ligninsulfonsaures Natrium, 2,2′-dinaphthyl-methan-6,6′-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleylmethyltaurinsaures Natrium erhalten. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel, z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedende Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt.Spray powders are preparations which are uniformly dispersible in water, in addition to the active ingredient in addition to a diluent or inert, wetting agents, e.g. B. polyoxethylated Alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenyl sulfonates and Dispersants, e.g. B. sodium lignosulfonic acid, 2,2′-dinaphthyl-methane-6,6′-disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or obtained sodium oleylmethyl tauric acid. Become emulsifiable concentrates by dissolving the active ingredient in an organic solvent, e.g. B. butanol, Cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or Hydrocarbons produced with the addition of one or more emulsifiers.
Als Emulgatoren können beispielsweise verwendet werden:The following can be used as emulsifiers:
Alkylarylsulfonsaure Calciumsalze wie Ca-dodecylbenzolsulfonat oder nichtionogene Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Sorbitanfettsäureester, Polyoxyethylensorbitan-Fettsäureester oder Polyoxethylensorbitester.Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or non-ionogenic Emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide-sorbitan fatty acid ester, Polyoxyethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.
Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z. B. Talkum, natürlichen Tonen wie Kaolin, Bentonit, Poryphillit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z. B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gegebenenfalls in Mischung mit Düngemitteln - granuliert werden.Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth. Granules can either be sprayed onto the adsorbable, granulated inert material or by applying Active ingredient concentrates by means of adhesives, e.g. B. polyvinyl alcohol, polyacrylic acid Sodium or mineral oils on the surface of carriers such as sand, kaolinite or of granulated inert material. Suitable active ingredients in the for Production of fertilizer granules in the usual way - optionally in a mixture with Fertilizers - be granulated.
In Spritzpulvern beträgt die Wirkstoffkonzentration 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-%. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.The active substance concentration in wettable powders is 10 to 90% by weight, the rest 100% by weight. consists of common formulation components. For emulsifiable concentrates the active ingredient concentration can be 5 to 80% by weight. Dusty formulations usually contain 5 to 20 wt .-%. In the case of granules, the active ingredient content depends in part depends on whether the active compound is liquid or solid and which compound is liquid or solid and which granulation aids, fillers etc. are used.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Lösungsmittel, Füll- oder Trägerstoffe.In addition, the active ingredient formulations mentioned may each contain usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, solvents, fillers or Carriers.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Konzentrate gegebenenfalls in üblicher Weise verdünnt, z. B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser.The concentrates available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water.
Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.Dusty and granular preparations as well as sprayable solutions are used before Application usually no longer diluted with other inert substances.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u. a. variiert die erforderliche Aufwandmenge. Sie kann innerhalb weiter Grenzen schwanken, z. B. von 0,005 bis 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch im Bereich von 0,01 bis 5 kg/ha.With the external conditions such as temperature, humidity and. a. varies the required Application rate. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha or more of active substance, but it is preferably in the range from 0.01 to 5 kg / ha.
Die erfindungsgemäßen Wirkstoffe können in ihren handelsüblichen Formulierungen entweder allein oder in Kombination mit weiteren, literaturbekannten Fungiziden angewendet werden.The active compounds according to the invention can be in their commercially available formulations either alone or in combination with other fungicides known from the literature be applied.
Als literaturbekannte Fungizide, die erfindungsgemäß mit den Verbindungen der Formel I kombiniert werden können, sind beispielsweise folgende Produkte zu nennen: Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, PP 969, Flutriafol, BAY-MEB 6401, Propiconazol, Etaconazol, Diclobutrazol, Bitertanol, Triadimefon, Triadimenol, Tebuconazole, Fluotrimazol, Tridemorph, Dimethomorph, Dodemorph, Fenpropimorph, Falimorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK-483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichlofunanid, Captafol, Captan, Folpet, Tolyfluanid, Chlorothalonil, Etridiazol, Iprodione, Procymidon, Vinclozol, Metomeclan, Myclozolin, Dichlozolinate, Fluorimide, Drazoxolan, Chinomethionate, Nitrothalisopropyl, Dithianon, Dinocap, Binapacryl, Fentinacetate, Fentinhydroxide, Carboxin, Oxycarboxin, Pyracarolid, Methfuroxam, Fenfura, Furmecyclos, Benodanil, Mebenil, Mepronil, Flutanalil, Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiofante, Thiofanatemethyl, CGD-95340 F, IKF-1216, Mancozeb, Zineb, Nabam, Thiram, Probineb, Prothiocarb, Propamocarb, Dodine, Guazatine, Dicloran, Quintozene, Chloroneb, Tecnazene, Biphenyl, Anilazine, 2-Phenylphenol, Kupferverbindungen wie Cu-oxychlorid, Oxine-Cu, Cu-oxide, Schwefel, Fosethylaluminium, Natrium-dodecylbenzolsulfonat, Natrium-dodecylsulfat, Natrium-C13/C15-alkoholethersulfonat, Natriumcetostearylphosphatester, Dioctyl-natriumsulfosuccinat, Natrium-isopropylnaphthalinsulfonat, Natrium-methylenbisnaphthalinsulfonat, Cetyl-trimethyl-ammoniumchlorid, Salze von langkettigen primären, sekundären oder tertiären Aminen, Alkyl-propyleamine, Lauryl-pyridinium-bromid, ethoxilierte quaternierte Fettamine, Alkyl-dimethyl-benzylammoniumchlorid und 1-Hydroxyethyl-2-alkyl-imidazolin.As fungicides known in the literature which, according to the invention, with the compounds of the formula I The following products can be combined, for example: Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, PP 969, Flutriafol, BAY-MEB 6401, Propiconazole, etaconazole, diclobutrazole, bitertanol, triadimefon, triadimenol, Tebuconazole, fluotrimazole, tridemorph, dimethomorph, dodemorph, fenpropimorph, Falimorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK-483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichlofunanid, Captafol, Captan, Folpet, Tolyfluanid, Chlorothalonil, etridiazole, iprodione, procymidone, vinclozole, metomeclan, myclozolin, Dichlozolinate, fluorimide, drazoxolan, quinomethionate, nitrothalisopropyl, dithianon, Dinocap, Binapacryl, Fentinacetate, Fentinhydroxide, Carboxin, Oxycarboxin, Pyracarolid, Methfuroxam, Fenfura, Furmecyclos, Benodanil, Mebenil, Mepronil, Flutanalil, Fuberidazole, thiabendazole, carbendazim, benomyl, thiofante, thiofanatemethyl, CGD-95340 F, IKF-1216, Mancozeb, Zineb, Nabam, Thiram, Probineb, Prothiocarb, Propamocarb, Dodine, Guazatine, Dicloran, Quintozene, Chloroneb, Tecnazene, Biphenyl, Anilazines, 2-phenylphenol, copper compounds such as Cu-oxychloride, Oxine-Cu, Cu-oxide, Sulfur, fosethyl aluminum, sodium dodecylbenzenesulfonate, sodium dodecyl sulfate, Sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, Dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate, Sodium methylene bisnaphthalene sulfonate, cetyl trimethyl ammonium chloride, Salts of long-chain primary, secondary or tertiary amines, alkyl-propyleamines, Lauryl-pyridinium-bromide, ethoxylated quaternized fatty amines, Alkyl-dimethyl-benzylammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline.
Die oben genannten Kombinationspartner stellen bekannte Wirkstoffe dar, die zum großen Teil in CH. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7. Auflage (1983), British Crop Protection Council, beschrieben sind.The above-mentioned combination partners are well-known active ingredients that are great Part in CH. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council.
Darüber hinaus können die erfindungsgemäßen Wirkstoffe, insbesondere die der aufgeführten Beispiele, in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, Formamidine, Zinnverbindungen, durch Mikroorganismen hergestellte Stoffe u. a. Bevorzugte Mischungspartner sind:In addition, the active compounds according to the invention, in particular those of the listed Examples, in their commercial formulations as well as in those formulations prepared application forms in a mixture with other active ingredients, such as insecticides, Attractants, sterilants, acaricides, nematicides, fungicides, growth regulators Substances or herbicides are present. Insecticides include, for example Phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds Microorganisms manufactured substances u. a. Preferred mix partners are:
1. Aus der Gruppe der Phosphorsäureester
Azinphos-ethyl, Azinphosmethyl, 1-(4-Chlorphenyl)-4-(O-ethyl,
S-propyl)phosphoryloxypyrazol (TIA-230), Chlorpyrifos, Coumaphos, Demeton,
Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion,
Fenthion, Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,
Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.1. From the group of phosphoric acid esters
Azinphos-ethyl, azinphosmethyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, dimethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
2. Aus der Gruppe der Carbamate
Aldicarb, Bendiocarb, BPMC (2-(1-Methylpropyl)phenylmethylcarbamat), Butocarboxim,
Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl,
Oxamyl, Primicarb, Promecarb, Propoxur, Thiodicarb.2. From the group of carbamates
Aldicarb, Bendiocarb, BPMC (2- (1-methylpropyl) phenylmethylcarbamate), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Primicarb, Promecarb, Propoxur, Thiodicarb.
3. Aus der Gruppe der Carbonsäureester
Allethrin, Alphamethrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin,
Cypermethrin, Deltamethrin, 2,2-Dimethyl-3-
2-chlor-2-trifluormethylvinyl)-cyclopropancarbonsäure-(alpha-
cyano-3-phenyl-2-methyl-benzyl)ester (FMC 54800, Fenpropathrin, Fenfluthrin, Fenvalerat,
Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin.
3. From the group of carboxylic acid esters
Allethrin, Alphamethrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-Dimethyl-3- 2-chloro-2-trifluoromethylvinyl) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl- benzyl) ester (FMC 54800, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin.
4. Aus der Gruppe der Formamidine
Amitraz, Chlordimeform.4. From the group of formamidines
Amitraz, chlorordime form.
5. Aus der Gruppe der Zinnverbindungen
Azocyclotin, Cyhexatin, Fenbutatinoxid.5. From the group of tin compounds
Azocyclotin, Cyhexatin, Fenbutatinoxid.
6. Sonstige
Abamektin, Bacillus thuringiensis, Bensultap, Binapacyl, Bromopropylate, Buprofecin,
Camphechlor, Cartap, Chlorbenzialate, Chlorfluazuron,
2-(4-Chlorphenyl)-4,5-diphenylthiophen (UBI-T 930), Chlofentezine,
Cyclopropancarbonsäure(2-naphthylmethyl)-ester (Ro 12-0470), Cyromacin, DDT, Dicofol,
N-(3,5-Dichlor-4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,-6-difluor-benzamide
(XRD 473), Diflubenzuron, N-(2,3-Dihydro-3-methyl-1,2-thiazol-2-ylidene)2,4-xylidine,
Dinobuton, Dinocap, Endosulfan,, Fenoxycarb, Fenthiocarb, Flubenzimine, Flufenoxuron,
Gamma-HCH, Hexythiazox, Hydramethylnon (AC 217 300), Ivermectin,
2-Nitro-methyl-4,5-dihydro-6H-thiazin (SD 52618), 2-Nitromethyl-3,4-dihydrothiazol (SD
35651), 2-Nitromethylene-1,3-thiazinan-3yl-carbamaldehyde (WL 108 477), Propargite,
Teflubenzuron, Tetradifon, Tetrasul, Thicyclam, Triflumaron, Kernpolyeder- und
Granuloseviren.6. Other
Abamectin, Bacillus thuringiensis, Bensultap, Binapacyl, Bromopropylate, Buprofecin, Camphechlor, Cartap, Chlorbenzialate, Chlorfluazuron, 2- (4-Chlorphenyl) -4,5-diphenylthiophene (UBI-T 930), Chlofentezine, Cyclopropanecarbmonic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) carbonyl) -2, -6-difluoro-benzamide ( XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidene) 2,4-xylidine, dinobutone, dinocap, endosulfan ,, fenoxycarb, fenthiocarb, flubenzimine, flufenoxuron, Gamma-HCH, hexythiazox, hydramethylnon (AC 217 300), ivermectin, 2-nitro-methyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2 -Nitromethylene-1,3-thiazinan-3yl-carbamaldehyde (WL 108 477), propargite, teflubenzuron, tetradifone, tetrasul, thicyclam, triflumarone, nuclear polyhedron and granulosic viruses.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren, die Wirkstoffkonzentration der Anwendungsformen kann von 0,0001 bis zu 100 Gew.-% Wirkstoff, vorzugsweise von 0,001 bis 1 Gew.-% liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weisen.The active substance content of those prepared from the commercially available formulations Forms of use can vary widely, the active ingredient concentration Use forms can be from 0.0001 to 100% by weight of active compound, preferably from 0.001 are up to 1% by weight. The application takes place in one of the application forms adapted usual ways.
Nachfolgende Beispiele dienen zur Erläuterung der Erfindung.The following examples serve to explain the invention.
a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile Wirkstoff und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.a) A dust is obtained by adding 10 parts by weight of active ingredient and 90 parts by weight Mixing talc as an inert substance and crushing it in a hammer mill.
b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gew.-Teile Wirkstoff, 65 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gew.-Teile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.b) A wettable powder which is readily dispersible in water is obtained by 25 Parts by weight of active ingredient, 65 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight Potassium lignosulfonate and 1 part by weight sodium oleoylmethyl taurine as wetting and Mixes dispersant and grinds in a pin mill.
c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat stellt man her, indem man 40 Gew.-Teile Wirkstoff mit 7 Gew.-Teilen eines Sulfobernsteinsäurehalbesters, 2 Gew.-Teilen eines Ligninsulfonsäure-Natriumsalzes und 51 Gew.-Teilen Wasser mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.c) A dispersion concentrate which is easily dispersible in water is prepared by adding 40 Parts by weight of active ingredient with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and mixed in one Grinding ball mill ground to a fineness of less than 5 microns.
d) Ein emulgierbares Konzentrat läßt sich herstellen aus 15 Gew.-Teilen Wirkstoff, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertem Nonylphenol (10 AeO) als Emulgator.d) An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 Parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated Nonylphenol (10 AeO) as an emulsifier.
e) Ein Granulat läßt sich herstellen aus 2 bis 15 Gew.-Teilen Wirkstoff und einem inerten Granulatträgermaterial wie Attapulgit, Bimsgranulat und/oder Quarzsand. Zweckmäßigerweise verwendet man eine Suspension des Spritzpulvers aus Beispiel b) mit einem Feststoffanteil von 30% und spritzt diese auf die Oberfläche eines Attapulgitgranulats, trocknet und vermischt innig. Dabei beträgt der Gewichtsanteil des Spritzpulvers ca. 5% und der des inerten Trägermaterials ca. 95% des fertigen Granulats. e) Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert one Granulate carrier material such as attapulgite, pumice granulate and / or quartz sand. A suspension of the wettable powder from example b) is expediently used a solids content of 30% and sprayed this onto the surface of a Attapulgite granules, dry and mix intimately. The weight percentage is Spray powder approx. 5% and that of the inert carrier material approx. 95% of the finished granulate.
4-Methyl-N-phenyl-2-(3-propinyloxy)-6-pyrimidinamin
Verbindung Nr. 14-methyl-N-phenyl-2- (3-propynyloxy) -6-pyrimidinamine
Compound No. 1
Zu 324 g wasserfreiem Natriumcarbonat in 1600 ml Wasser gab man 416 g Acetessigsäureethylester und anschließend 445 g S-Methylisothioharnstoffsulfat, rührte etwa 96 Stunden bei Raumtemperatur und stellte dann mit Essigsäure einen pH-Wert von 5,5 bis 6 ein. Nach Abfiltrieren und Trocknung des Produkts erhielt man 485 g (97%) 6-Methyl-2-methylmercapto-1H-pyrimidin-4-on, Smp.: 180-185°C.416 g were added to 324 g of anhydrous sodium carbonate in 1600 ml of water Acetoacetic acid ethyl ester and then 445 g of S-methylisothiourea sulfate, stirred about 96 hours at room temperature and then adjusted to pH 5.5 to 6 with acetic acid a. After filtering off and drying the product, 485 g (97%) were obtained. 6-methyl-2-methylmercapto-1H-pyrimidin-4-one, M.p .: 180-185 ° C.
In 500 ml POCl₃ und 15 ml N,N-Dimethylanilin erhitzte man 425 g 6-Methyl-2-methylmercapto-1H-pyrimidin-4-on unter Rückfluß. Nach vollständiger Lösung des Pyrimidions (etwa 60 Minuten) destillierte man bei etwa 200 mm Hg das POCl₃ ab nahm in Methylenchlorid auf, hydrolysierte und wusch die organische Phase neutral, trocknete diese und destillierte (Sdp.: 63-66°C/0,2 mm Hg). Man erhielt 397 g (83%) 4-Chlor-6-methyl-2-methylthiopyrimidin, Smp.: 38-40°C.In 500 ml of POCl₃ and 15 ml of N, N-dimethylaniline, 425 g were heated 6-methyl-2-methylmercapto-1H-pyrimidin-4-one under reflux. After a complete solution the pyrimidione (about 60 minutes) was distilled at about 200 mm Hg the POCl₃ took in Methylene chloride, hydrolyzed and washed the organic phase neutral, dried it and distilled (bp: 63-66 ° C / 0.2 mm Hg). 397 g (83%) were obtained 4-chloro-6-methyl-2-methylthiopyrimidine, m.p .: 38-40 ° C.
Man suspendierte 461 g eines Gemisches aus Kaliumperoxomonosulfat, 2 KHSO₅, KHSO₄ und K₂SO₄ in einer Mischung aus jeweils 300 ml Methanol, Wasser und Essigsäure und gab unter Rühren 87,3 g 4-Chlor-6-methyl-2-methylthiopyrimidin hinzu. Nach Abklingen der exothermen Reaktion (etwa 1 Stunde) extrahierte man mit reichlich Methylenchlorid, wusch die organische Phase, trocknete diese und destillierte das Lösungsmittel ab. Man erhielt 67 g (65%) 4-Chlor-6-methyl-2-methylsulfonyl-pyrimidin, Smp.: 81-84°C.461 g of a mixture of potassium peroxomonosulfate, 2 KHSO₅, KHSO₄ were suspended and K₂SO₄ in a mixture of 300 ml of methanol, water and acetic acid and gave 87.3 g of 4-chloro-6-methyl-2-methylthiopyrimidine were added with stirring. After the exothermic reaction (about 1 hour) was extracted with plenty of methylene chloride, washed the organic phase, dried it and distilled off the solvent. 67 g were obtained (65%) 4-chloro-6-methyl-2-methylsulfonyl-pyrimidine, m.p .: 81-84 ° C.
Zu 3,2 g NaH (80% in Mineralöl) in 150 ml abs. THF tropfte man 5,9 g Propinylalkohol, rührte eine Stunde und gab dann 20,7 g 4-Chlor-6-methyl-2-methylthiopyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach Abdestillation des Lösungsmittels 13,4 g (74%) 4-Chlor-6-methyl-2-propinyloxypyrimidin, Sdp.: 85-95°C/0,05-0,01 mbar.To 3.2 g NaH (80% in mineral oil) in 150 ml abs. THF was added dropwise to 5.9 g of propynyl alcohol, stirred for an hour and then added 20.7 g of 4-chloro-6-methyl-2-methylthiopyrimidine. To The mixture was hydrolyzed for 16 hours, extracted with ethyl acetate or methylene chloride and washed organic phase, dried and obtained after distilling off the solvent 13.4 g (74%) 4-chloro-6-methyl-2-propynyloxypyrimidine, Bp: 85-95 ° C / 0.05-0.01 mbar.
Zu 80 ml Wasser gab man eine Lösung von 13,4 g 4-Chlor-6-methyl-2-propinyloxypyrimidin in 20 ml Aceton, gab dann 6,8 g Anilin sowie etwa 1,5 ml konz. Salzsäure hinzu und erhitzte etwa 1 Stunde unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man etwa 100 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase trocknete man und destillierte das Lösungsmittel ab. Man erhielt ein festes Rohprodukt, welches aus Benzin/Essigester-Mischungen umkristallisiert werden konnte. Nach der Umkristallisation erhielt man 16,4 g (94%) 4-Methyl-N-phenyl-2-(3-propinyloxy)-6-pyrimidinamin, Smp.: 94-97°C.A solution of 13.4 g of 4-chloro-6-methyl-2-propynyloxypyrimidine was added to 80 ml of water in 20 ml of acetone, then gave 6.8 g of aniline and about 1.5 ml of conc. Added hydrochloric acid and heated about 1 hour under reflux. After the reaction mixture had cooled, about 100 ml were added Water to the reaction mixture, the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase and dried distilled off the solvent. A solid crude product was obtained, which consists of Gasoline / ethyl acetate mixtures could be recrystallized. After recrystallization 16.4 g (94%) of 4-methyl-N-phenyl-2- (3-propynyloxy) -6-pyrimidinamine were obtained, m.p .: 94-97 ° C.
4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6-aminopyrimidin
Verbindung Nr. 614-methyl-N-methyl-2-propynyloxy-N-phenyl-6-aminopyrimidine
Compound No. 61
Zu 80 ml Wasser gab man eine Lösung von 17,6 g 4-Chlor-6-methyl-2-methylthiopyrimidin in 20 ml Aceton, gab dann 10,7 g N-Methylanilin sowie etwa 1,5 ml konz. Salzsäure hinzu und erhitzte etwa 1 Stunde unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man etwa 100 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase, Trocknung, Abdestillation des Lösungsmittels und Umkristallisation des Produkts aus einer Heptan/Essigestermischung erhielt man 16,3 g (66%) 4-Methyl-N-methyl-2-methylthio-N-phenyl-6-pyrimidinamin, Smp.: 88-89°C. A solution of 17.6 g of 4-chloro-6-methyl-2-methylthiopyrimidine was added to 80 ml of water in 20 ml of acetone, then gave 10.7 g of N-methylaniline and about 1.5 ml of conc. Hydrochloric acid and heated under reflux for about 1 hour. After the reaction mixture had cooled, about 100 ml of water to the reaction mixture, made the mixture slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase, drying, Distillation of the solvent and recrystallization of the product from a Heptane / ethyl acetate mixture gave 16.3 g (66%) 4-methyl-N-methyl-2-methylthio-N-phenyl-6-pyrimidinamine, M.p .: 88-89 ° C.
Man suspendierte 46 g eines Gemisches aus Kaliumperoxomonosulfat, 2 KHSO₅, KHSO₄ und K₂SO₄ in einer Mischung aus jeweils 100 ml Methanol, Wasser und Essigsäure und gab unter Rühren 12,3 g 4-Methyl-N-methyl-2-methylthio-N-phenyl-6-pyrimidinamin hinzu. Nach Abklingen der exothermen Reaktion (etwa 1 Stunde) extrahierte man mit reichlich Methylenchlorid, wusch die organische Phase und erhielt nach Trocknung und Abdestillation des Lösungsmittels 9,2 g (66%) 4-Methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamin, Smp.: 166-167°C.46 g of a mixture of potassium peroxomonosulfate, 2 KHSO₅, KHSO₄ were suspended and K₂SO₄ in a mixture of 100 ml of methanol, water and acetic acid and gave with stirring, add 12.3 g of 4-methyl-N-methyl-2-methylthio-N-phenyl-6-pyrimidinamine. After the exothermic reaction had subsided (about 1 hour), the mixture was extracted with plenty Methylene chloride, washed the organic phase and obtained after drying and distillation of the solvent 9.2 g (66%) 4-methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamine, M.p .: 166-167 ° C.
Zu 1,1 g NaH (80% in Mineralöl) in 50 ml abs. THF tropfte man 1,9 g Propinylalkohol, rührte eine Stunde und gab dann 7,0 g 4-Methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach Abdestillieren des Lösungsmittels und säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (1 : 1) als Laufmittel, 5,4 g (85%) 4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6-aminopyrimidin, Smp.: 88-90°C.To 1.1 g NaH (80% in mineral oil) in 50 ml abs. THF was added dropwise 1.9 g of propynyl alcohol, stirred for an hour and then gave 7.0 g 4-Methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamine added. After 16 hours hydrolyzed, extracted with ethyl acetate or methylene chloride, the organic was washed Phase, dried and obtained after distilling off the solvent and column chromatographic purification of the product, with ethyl acetate and heptane (1: 1) as Mobile phase, 5.4 g (85%) 4-methyl-N-methyl-2-propynyloxy-N-phenyl-6-aminopyrimidine, M.p .: 88-90 ° C.
2-(1-Jod-3-propinyloxy)-4-methyl-N-methyl-N-phenyl-6-aminopyrimidin
Verbindung Nr. 632- (1-iodo-3-propynyloxy) -4-methyl-N-methyl-N-phenyl-6-aminopyrimidine
Compound No. 63
Unter N₂-Atmosphäre legte man 3,2 g 4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6-aminopyrimidin in 60 ml THF vor, kühlte auf -78°c und gab 8,5 ml 1,6 molare n-Butyllithiumlösung in Hexan hinzu. Nach etwa 1 Stunde gab man 3,5 g Jod zu, ließ die Lösung auf Raumtemperatur erwärmen und hydrolisierte nach etwa 30 Minuten. Man nahm in Methylenchlorid auf, wusch mit Wasser, trocknete die Lösung, destillierte das Lösungsmittel ab und erhielt nach säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (1 : 1) als Laufmittel, 3,4 g (73%) 2-(1-Jod-3-propinyloxy)-4-methyl-N-methyl-N-phenyl-6-aminopyrimidin,- Smp.: 177-180°C.3.2 g was placed under an N 2 atmosphere Pre-4-methyl-N-methyl-2-propynyloxy-N-phenyl-6-aminopyrimidine in 60 ml of THF cooled -78 ° C and added 8.5 ml of 1.6 molar n-butyllithium solution in hexane. After about 1 hour 3.5 g of iodine were added, the solution was allowed to warm to room temperature and hydrolyzed about 30 minutes. It was taken up in methylene chloride, washed with water, the solution was dried, the solvent was distilled off and, after purification by column chromatography, the Product, with ethyl acetate and heptane (1: 1) as eluent, 3.4 g (73%) 2- (1-iodo-3-propynyloxy) -4-methyl-N-methyl-N-phenyl-6-aminopyrimidine, mp: 177-180 ° C.
4-(3-Chloranilino)-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidi-n
Verbindung Nr. 1184- (3-chloroanilino) -2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidi-n
Compound No. 118
Zu einer frisch hergestellten Natriummethanlösung aus 46 g Natrium und 1000 ml Ethanol gab man 107 g Thioharnstoff und danach 184 g Trifluoressigsäureethylester, erhitzte dann 6 Stunden unter Rückfluß, destillierte das Lösungsmittel ab und nahm in Eiswasser auf. Nach der Zugabe von etwa 120 ml konz. Salzsäure stellte man mit Essigsäure einen pH-Wert zwischen 5 und 6 ein, und erhielt nach dem Abfiltrieren 162 g (83%) 2-Mercapto-4-trifluormethyl-1,3-dihydro-4-pyrimidinon.To a freshly prepared sodium methane solution from 46 g sodium and 1000 ml ethanol 107 g of thiourea and then 184 g of ethyl trifluoroacetate were added, and 6 were then heated Hours under reflux, the solvent distilled off and taken up in ice water. To the addition of about 120 ml of conc. Hydrochloric acid was adjusted to pH with acetic acid between 5 and 6, and after filtering off received 162 g (83%) 2-mercapto-4-trifluoromethyl-1,3-dihydro-4-pyrimidinone.
Zu 6 g Natriumhydrid (80% in Mineralöl) in 200 ml Acetonitril gab man 39,3 g 2-Mercapto-4-trifluormethyl-1,3-dihydro-4-pyrimidinon und 1 ml Tri(C₈/C₁₀)alkylmethylammoniumchlorid, rührte etwa 1 Stunde, tropfte dann 34 ml Propinylbromid (80-%-Lösung in Toluol) hinzu und erhitzte etwa 6 Stunden unter Rückfluß. Nach Abkühlung und Einengung des Reaktionsgemisches nahm man in 300 ml Wasser auf, neutralisierte mit Essigsäure und erhielt nach dem Abfiltrieren 46 g (98%) 2-(3-(1-Propinyl)-thio)-6-trifluormethyl-1H-4-pyrimidinon, Smp.: 158-163°C.39.3 g were added to 6 g of sodium hydride (80% in mineral oil) in 200 ml of acetonitrile 2-mercapto-4-trifluoromethyl-1,3-dihydro-4-pyrimidinone and 1 ml Tri (C₈ / C₁₀) alkylmethylammonium chloride, stirred for about 1 hour, then dripped 34 ml Propinyl bromide (80% solution in toluene) was added and heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and received 46 g (98%) after filtering off 2- (3- (1-propynyl) thio) -6-trifluoromethyl-1H-4-pyrimidinone, m.p .: 158-163 ° C.
In 200 ml POCl₃ und 5 ml N,N-Dimethylanilin erhitzte man 46 g 2-(3-(1-Propinyl)-thio)-6-trifluormethyl-1H-4-pyrimidinon unter Rückfluß. Nach vollständiger Lösung des Pyrimidinons (etwa 60 Minuten) destillierte man bei etwa 200 mm Hg das POCL₃ ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknete, destillierte (Sdp.: 56-57°C/0,02 mm Hg) und erhielt 39,2 g (78%) 4-Chlor-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidin.In 200 ml of POCl₃ and 5 ml of N, N-dimethylaniline was heated 46 g 2- (3- (1-Propynyl) thio) -6-trifluoromethyl-1H-4-pyrimidinone under reflux. To complete solution of the pyrimidinone (about 60 minutes) was distilled at about 200 mm Hg the POCL₃ from, took up in methylene chloride and hydrolyzed, washed the organic phase neutral, dried, distilled (bp: 56-57 ° C / 0.02 mm Hg) and received 39.2 g (78%) 4-chloro-2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidine.
Zu 40 ml Wasser gab man eine Lösung von 5,1 g 4-Chlor-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidin in 10 ml Aceton, gab dann 2,6 g Anilin sowie etwa 1 ml konz. Salzsäure hinzu und erhitzte etwa 2 Stunden unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man etwa 50 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase trocknete man, destillierte das Lösungsmittel ab und erhielt nach säulenchromatographischer Reinigung, mit Essigester und Heptan (3 : 7) als Laufmittel, 0,8 g (12%) 4-(3-Chloranilino)-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidi-n, Smp.: 85-87°C.A solution of 5.1 g was added to 40 ml of water 4-Chloro-2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidine in 10 ml acetone, then gave 2.6 g Aniline and about 1 ml conc. Hydrochloric acid was added and heated under reflux for about 2 hours. To Cooling of the reaction mixture was added to the reaction mixture about 50 ml of water the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. To Washing the organic phase was dried, the solvent was distilled off and obtained after purification by column chromatography, with ethyl acetate and heptane (3: 7) as eluent, 0.8 g (12%) 4- (3-chloroanilino) -2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidi-n, m.p .: 85-87 ° C.
4-Anilino-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin
Verbindung Nr. 2494-anilino-5-methoxy-2- (3- (1-propynyl) thio) pyrimidine
Compound No. 249
Zu 33 g NaH (80% in Mineralöl) in 600 ml abs. THF tropfte man 15% einer Mischung aus 118 g Ameisensäureethylester und 104 g Methoxyessigsäuremethylester und erwärmte das Reaktionsgemisch gelinde, bis eine Wasserstoffentwicklung festzustellen war. Den restlichen Anteil der obigen Mischung tropfte man anschließend so zu, daß die Reaktionstemperatur bei 35-40°C lag und eine mittlere Wasserstoffentwicklung beobachtet wurde. Hierbei bildete sich ein schwer rührbares Reaktionsgemisch. Nach Stehenlassen über 16 Stunden gab man 600 ml Isopropanol und 76 g Thioharnstoff hinzu und erhitzte dieses Reaktionsgemisch 120 Minuten unter Rückfluß, wobei das THF teilweise abdestilliert wurde. Anschließend destillierte man die Lösungsmittel ab und nahm den Rückstand in Wasser auf, säuerte mit Essigsäure an und erhielt nach dem Abfiltrieren 145 g (92%) 5-Methoxy-2-thio-1,3-dihydro-4-pyrimidinon, Smp.: 275-278°C. To 33 g NaH (80% in mineral oil) in 600 ml abs. 15% of a mixture was dripped out of THF 118 g of ethyl formate and 104 g of methyl methoxyacetate and warmed the The reaction mixture was mild until hydrogen evolution was observed. The rest Portion of the above mixture was then added dropwise so that the reaction temperature at 35-40 ° C and an average hydrogen evolution was observed. Here formed a difficult to stir reaction mixture. After standing for over 16 hours one gave 600 ml of isopropanol and 76 g of thiourea were added and this reaction mixture was heated 120 Minutes under reflux, the THF being partially distilled off. Subsequently the solvents were distilled off and the residue was taken up in water and acidified Acetic acid and, after filtering off, obtained 145 g (92%) 5-methoxy-2-thio-1,3-dihydro-4-pyrimidinone, m.p .: 275-278 ° C.
Zu 12 g Natriumhydrid (80% in Mineralöl) in 200 ml Acetonitril gab man 47,4 g 5-Methoxy-2-thio-1,3-dihydro-4-pyrimidinon und 1 ml Tri(C₈/C₁₀)alkylmethylammoniumchlorid, rührte etwa 1 Stunde, tropfte dann 50 ml Propinylbromid (80-%-Lösung in Toluol) hinzu und erhitzte etwa 6 Stunden unter Rückfluß. Nach Abkühlen und Einengung des Reaktionsgemisches nahm man in 300 ml Wasser auf, neutralisierte mit Essigsäure und erhielt nach dem Abfiltrieren 44 g (75%) 5-Methoxy-2-(3-(1-propinyl)-thio)-1H-4-pyrimidinon, Smp.: 158°C.47.4 g were added to 12 g of sodium hydride (80% in mineral oil) in 200 ml of acetonitrile 5-methoxy-2-thio-1,3-dihydro-4-pyrimidinone and 1 ml Tri (C₈ / C₁₀) alkylmethylammonium chloride, stirred for about 1 hour, then dripped 50 ml Propinyl bromide (80% solution in toluene) was added and heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and obtained 44 g (75%) after filtering off 5-methoxy-2- (3- (1-propynyl) thio) -1H-4-pyrimidinone, m.p .: 158 ° C.
In 200 ml POCl₃ und 5 ml N,N-Dimethylanilin erhitzte man 44 g 5-Methoxy-2-(3-(1-propinyl)-thio)-1H-4-pyrimidinon unter Rückfluß. Nach vollständiger Lösung des Pyrimidinons (etwa 60 Minuten) destillierte man bei etwa 200 mm Hg das POCl₃ ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknete diese und erhielt nach Abdestillieren des Lösungsmittels 24,8 g (52%) 4-Chlor-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin, Smp.: 70-72°C.In 200 ml of POCl₃ and 5 ml of N, N-dimethylaniline was heated 44 g 5-methoxy-2- (3- (1-propynyl) thio) -1H-4-pyrimidinone under reflux. After more complete Solution of the pyrimidinone (about 60 minutes), the POCl₃ was distilled off at about 200 mm Hg, took up in methylene chloride and hydrolyzed, washed the organic phase neutral, dried this and, after distilling off the solvent, obtained 24.8 g (52%) 4-chloro-5-methoxy-2- (3- (1-propynyl) thio) pyrimidine, M.p .: 70-72 ° C.
Zu 40 ml Wasser gab man eine Lösung von 5,4 g 4-Chlor-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin in 10 ml Aceton, dann gab 2,3 g Anilin sowie etwa 1 ml konz. Salzsäure hinzu und erhitzte etwa 2 Stunden zum Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man etwa 50 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase, Trocknen, Abdestillation des Lösungsmittels und säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (7 : 3) als Laufmittel, erhielt man 5,2 g (77%) 4-Anilino-5-methoxy-2-(3-(1-propinyl)-thio-pyrimidin, Smp.: 95-96°C.A solution of 5.4 g was added to 40 ml of water 4-chloro-5-methoxy-2- (3- (1-propynyl) thio) pyrimidine in 10 ml acetone, then gave 2.3 g aniline and about 1 ml of conc. Hydrochloric acid was added and heated to reflux for about 2 hours. To Cooling of the reaction mixture was added to the reaction mixture about 50 ml of water the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. To Washing the organic phase, drying, distilling off the solvent and column chromatographic purification of the product, with ethyl acetate and heptane (7: 3) as Eluent, 5.2 g (77%) of 4-anilino-5-methoxy-2- (3- (1-propynyl) thio-pyrimidine were obtained, M.p .: 95-96 ° C.
Die Ausbeuten der angegebenen Beispiele wurden nicht optimiert. Entsprechend der oben aufgeführten Beispiele können die in der Tabelle 1 genannten Verbindungen hergestellt werden. The yields of the examples given were not optimized. According to the examples listed above, the compounds listed in Table 1 can be prepared.
Weizenpflanzen der Sorte "Diplomat" wurden etwa 4 Wochen nach Aussaat mit wäßrigen Suspensionen der erfindungsgemäßen Verbindungen tropfnaß behandelt.Wheat plants of the "Diplomat" variety were watered about 4 weeks after sowing Suspensions of the compounds according to the invention treated to runoff.
Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer wäßrigen Sporensuspension von Pseudocercosporella herpotrichoides inokuliert. Die Pflanzen wurden danach bei 16-18°C und etwa 90-100% rel. Luftfeuchte gehalten.After the spray coating had dried on, the plants were washed with an aqueous Spore suspension of Pseudocercosporella herpotrichoides inoculated. The plants were then at 16-18 ° C and about 90-100% rel. Humidity kept.
Nach einer Inkubationszeit von etwa 4 Wochen konnte die Befallsauswertung der Versuchspflanzen vorgenommen werden. Der Wirkungsgrad wurde aus dem Befallsgrad im Vergleich zu den unbehandelten, infizierten Kontrollpflanzen ermittelt und ist in Tabelle 2 wiedergegeben. After an incubation period of about 4 weeks, the infection evaluation of the Trial plants are made. The efficiency was determined from the degree of infestation in the Comparison to the untreated, infected control plants determined and is in Table 2 reproduced.
Etwa 14 Tage alte Ackerbohnen der Sorte "Harz Freya" oder "Frank's Ackerperle" wurden mit wäßrigen Suspensionen der erfindungsgemäßen Verbindungen tropfnaß behandelt.About 14 days old beans of the variety "Harz Freya" or "Frank's Ackerperle" were also with aqueous suspensions of the compounds according to the invention treated to runoff.
Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension (1,5 Mio Sporen/ml) von Botrytis cinerea (BCM-resistenter Stamm) inokuliert. Die Pflanzen wurden in einer Klimakammer bei 20-22°C und etwa 99% rel. Luftfeuchte weiterkultiviert. Die Infektion der Pflanzen äußerte sich in der Bildung schwarzer Flecke auf Blättern und Stengeln. Die Auswertung der Versuche erfolgte etwa 1 Woche nach Inokulation.After the spray coating had dried on, the plants were spore-suspended (1.5 Million spores / ml) of Botrytis cinerea (BCM-resistant strain). The plants were in a climatic chamber at 20-22 ° C and about 99% rel. Humidity continued to be cultivated. The infection of the plants manifested itself in the formation of black spots on leaves and Stems. The tests were evaluated about 1 week after inoculation.
Der Wirkungsgrad der Prüfsubstanzen wurde prozentual zur unbehandelten, infizierten Kontrolle bonitiert und ist in Tabelle 3 wiedergegeben. The efficiency of the test substances was a percentage of the untreated, infected Control is rated and is shown in Table 3.
Claims (8)
R¹, R² = unabhängig voneinander Wasserstoff, (C₁-C₉)Alkyl, Cyano-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, gegebenenfalls substituierter 5- oder 6gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteilteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R¹ und R² gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,
R³ = Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, Cyano-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl, (C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls substituierter 5- oder 6gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann.
R⁴, R⁶, R⁶ = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano, Thiocyano, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, (C₁-C₄)Alkylcarbonylamino, Halo-(C₁-C₄)alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Haloalkoxycarbonyl, (C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls substituierter 5- oder 6gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁴, R⁵ und/oder R⁶ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,
R⁷ = Wasserstoff, Formyl, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Halo-(C₁-C₄)alkoxy, Amino(C₁-C₄)alkoxy, (C₁-C₄)Alkylamino(C₁-C₄)alkoxy, (C₁-C₄)Alkoxy(C₁-C₄)alkoxy, Amino, (C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, Cyano-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl, (C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, (C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert sein kann,
R⁷ und R⁴ und/oder R⁵ gegebenfalls zusammen einen gesättigten, oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,
R⁸, R⁹ = unabhängig voneinander Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, Cyano-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo-(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, Halo-(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-, (C₁-C₄)Dialkylamino-, (C₃-C₉)Cycloalkylamino-, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Dialkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Haloalkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Haloalkoxycarbonyl, (C₁-C₄)Alkylthiocarbonyl, (C₁-C₄)Haloalkylthiocarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl, (C₁-C₄)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxy-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenylamino-(C₁-C₄)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁸ und R⁹ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,
X = Sauerstoff oder Schwefel und
n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze.1. Compounds of formula I. wherein
R¹, R² = independently of one another hydrogen, (C₁-C₉) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl , (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo- (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄ ) Alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl , where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C ) alkyl, optionally substituted phenylamino (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester, (C₁- C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents one or more times can be substituted by halogen atoms,
R¹ and R² optionally together a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R³ = hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄) alkyl, ( C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio, halo- (C₁-C₄ ) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl , (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁- C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄ ) Haloalkoxycarbonyl, (C₁-C₄) alkylthio carbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part (heteroaromatic) is up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁- C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the sub can be substituted one or more times by halogen atoms.
R⁴, R⁶, R⁶ = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) Alkylamino, (C₁-C₄) dialkylamino, (C₁-C₄) alkylcarbonylamino, halo- (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio- (C₁- C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄ ) Dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) Heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁ -C₄) alkyl, (C ₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁ -C₄) haloalkoxycarbonyl, (C₁-C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenoxy, optionally substituted phenoxy , optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- ( C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part (heteroaroma at) up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply by nitro or cyano may be substituted, and halo in the substituents may be substituted one or more times by halogen atoms,
R⁴, R⁵ and / or R⁶ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R⁷ = hydrogen, formyl, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, halo- (C₁-C₄) alkoxy, amino (C₁-C₄) alkoxy, (C₁-C₄) alkylamino (C₁-C₄) alkoxy, (C₁-C₄) alkoxy (C₁-C₄) alkoxy, amino, (C₁-C₄) alkylamino, (C₁-C₄) dialkylamino, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- ( C₁-C₄) alkyl, halo (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio , Halo (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂- C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉ ) Cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, ( C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C -C₄) alkyl, (C₁-C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) haloalkoxycarbonyl, (C₁- C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, (C₁-C₄) haloalkylaminocarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄ ) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo- (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino - (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, where optionally substituted is to be understood that the phenyl moiety up to three times by halogen, ester (C₁-C₄) alkyl, (C₁-C₄) alkoxy , (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can be substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁷ and R⁴ and / or R⁵ optionally together a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R⁸, R⁹ = independently of one another hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, halo- (C₁-C₄ ) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo- (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- ( C₁-C₄) alkylthio, halo (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino-, (C₁-C₄) dialkylamino-, (C₃-C₉) cycloalkylamino-, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl , where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁- C₄) dialkylaminocarbonyl- (C₁-C₄) alkyl, (C -C₄) alkylcarbonyl, (C₁-C₄) haloalkylcarbonyl, (C₁-C₄) alkoxycarbonyl, (C₁-C₄) haloalkoxycarbonyl, (C₁-C₄) alkylthiocarbonyl, (C₁-C₄) haloalkylthiocarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, ( C₁-C₄) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C₁-C₄) alkyl, optionally substituted phenoxy- (C₁-C₄) alkyl, optionally substituted phenylmercapto- (C₁-C₄) alkyl, optionally substituted phenylketo - (C₁-C₄) alkyl, optionally substituted phenyloxycarbonyl- (C₁-C₄) alkyl, optionally substituted phenylamino- (C₁-C₄) alkyl, optionally substituted phenoxyphenyl- (C₁-C₄) alkyl, whereby optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply by nitro ode r cyano can be substituted, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁸ and R⁹ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
X = oxygen or sulfur and
n = a number from 0 to 8, and their acid addition salts.
R¹, R² bevorzugt unabhängig voneinander Wasserstoff, (C₁-C₉)Alkyl, im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenyl,
R¹ und R² gegebenenfalls einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,
R³ Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl, Dihydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituierter 5- oder 6gliedriger Heteroaromat, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Säureester, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁴, R⁵, R⁶ = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano, Thiocyano, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, Halo-(C₁-C₄)alkyl, Hydroxy-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Halo-(C₁-C₄)alkylthio, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Alkoxycarbonyl, Aminocarbonyl, (C₁-C₄)Alkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁴, R⁵ und/oder R⁶ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,
R⁷ = Wasserstoff, (C₁-C₄)Alkyl, Cyano-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy, Halo-(C₁-C₄)alkoxy, Amino(C₁-C₄)alkoxy, (C₁-C₄)Alkylamino(C₁-C₄)alkoxy, (C₁-C₄)Alkoxy(C₁-C₄)alkoxy, Amino, (C₁-C₄)Alkylamino, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, Perhalo-(C₁-C₄)alkylthio, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkoxycarbonyl-(C₁-C₄)alkyl, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C₁-C₄)alkyl,sein, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁷ und R⁴ und/oder R⁵ können zusammen einen gesättigten, teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,
R⁸, R⁹ = unabhängig voneinander Wasserstoff, Halogen, (C₁-C₄)Alkyl, Hydroxy-(C₁-C₄)alkyl, Perhalo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, (C₁-C₄)-Alkoxy, Halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)Alkylthio, (C₁-C₄)Alkylthio-(C₁-C₄)alkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₁-C₄)Alkylamino, (C₁-C₄)Dialkylamino, (C₃-C₉)Cycloalkylamino, (C₁-C₄)Alkylamino-(C₁-C₄)alkyl, (C₁-C₄)Dialkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)Cycloalkyl, (C₃-C₉)Cycloalkyl-(C₁-C₄)alkyl, (C₃-C₉)Heterocycloalkyl-(C₁-C₄)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C₁-C₄)Alkyl substituiert sein können, (C₁-C₄)Alkylcarbonyl, (C₁-C₄)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenoxyphenyl-(C₁-C₄)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylthio, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann,
R⁸ und R⁹ gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,
X = Sauerstoff oder Schwefel und
n = ist eine Zahl von 0 bis 4 bedeuten, sowie deren Säureadditionssalze.2. Compounds of formula I, wherein
R¹, R² preferably independently of one another hydrogen, (C₁-C₉) alkyl, in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenyl,
R¹ and R² optionally a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
R³ is hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, dihydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl , (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted 5- or 6-membered heteroaromatic, where optionally substituted is understood to mean that the phenyl part (heteroaromatic) up to three times by halogen, acid ester, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can be substituted simply by nitro or cyano, and halo in the substituents one or more times by halogena tome may mean substituted,
R⁴, R⁵, R⁶ = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) Alkylamino, (C₁-C₄) dialkylamino, halo (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy- ( C₁-C₄) alkyl, (C₁-C₄) alkylthio, halo- (C₁-C₄) alkylthio, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, wherein the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁-C₄) alkylaminocarbonyl- (C₁-C₄) alkyl, (C₁-C₄) Alkoxycarbonyl, (C₁-C₄) alkoxycarbonyl, aminocarbonyl, (C₁-C₄) alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally s substituted phenylketo (C₁-C₄) alkyl, where optionally substituted is to be understood that the phenyl moiety up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio , (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can simply be substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁴, R⁵ and / or R⁶ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
R⁷ = hydrogen, (C₁-C₄) alkyl, cyano- (C₁-C₄) alkyl, (C₁-C₄) alkoxy, halo- (C₁-C₄) alkoxy, amino (C₁-C₄) alkoxy, (C₁-C₄) alkylamino (C₁-C₄) alkoxy, (C₁-C₄) alkoxy (C₁-C₄) alkoxy, amino, (C₁-C₄) alkylamino, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, Perhalo- (C₁-C₄) alkylthio, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl , (C₃-C₉) heterocycloalkyl- (C₁-C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkoxycarbonyl- (C₁-C₄) alkyl, (C₁- C₄) alkylcarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo- (C₁-C₄) alkyl, whereby optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester , (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio , (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or can simply be substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R⁷ and R⁴ and / or R⁵ together can form a saturated, partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
R⁸, R⁹ = independently of one another hydrogen, halogen, (C₁-C₄) alkyl, hydroxy- (C₁-C₄) alkyl, perhalo- (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl, ( C₁-C₄) alkoxy, halo (C₁-C₄) alkoxy- (C₁-C₄) alkyl, (C₁-C₄) alkylthio, (C₁-C₄) alkylthio- (C₁-C₄) alkyl, (C₂-C₆) alkenyl, (C₂-C₆) alkynyl, (C₁-C₄) alkylamino, (C₁-C₄) dialkylamino, (C₃-C₉) cycloalkylamino, (C₁-C₄) alkylamino- (C₁-C₄) alkyl, (C₁-C₄) dialkylamino- ( C₁-C₄) alkyl, (C₃-C₉) cycloalkylamino- (C₁-C₄) alkyl, (C₃-C₉) cycloalkyl, (C₃-C₉) cycloalkyl- (C₁-C₄) alkyl, (C₃-C₉) heterocycloalkyl- (C₁ -C₄) alkyl, where the cyclic radicals can be substituted up to three times by (C₁-C₄) alkyl, (C₁-C₄) alkylcarbonyl, (C₁-C₄) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenoxyphenyl- ( C₁-C₄) alkyl, where optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, (C₁-C₄) alkylthio, (C₁-C₄) haloalkyl, (C₁-C₄) haloalkoxy or simply substituted by nitro or cyano may mean halo in the substituents substituted one or more times by halogen atoms,
R⁸ and R⁹ optionally together a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
X = oxygen or sulfur and
n = is a number from 0 to 4 and their acid addition salts.
R¹, R² unabhängig voneinander Wasserstoff oder (C₁-C₄)Alkyl,
R¹ und R² gegebenenfalls zusammen einen Teil eines gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 5 oder 6 Ringgliedern,
R³ Wasserstoff oder Halogen,
R⁴, R⁵, R⁶ unabhängig voneinander Wasserstoff, Halogen, (C₁-C₄)Alkyl, (C₁-C₄)-Alkoxy oder im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenoxy,
R³, R⁵ und R⁶ zusammen einen oder einen Teil eines gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroaromaten O, N oder S mit 5 bis 7 Ringgliedern,
R⁷ = Wasserstoff oder (C₁-C₄)Alkyl,
R⁸ = Wasserstoff, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Phenyl-(C₁-C₄)alkoxy oder Halogen,
R⁹ = Wasserstoff, (C₁-C₄)Alkyl, Perhalo-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl oder Phenyl-(C₁-C₄)alkyl,
R⁸ und R⁹ gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroaromaten mit 5 bis 6 Ringgliedern,
X = Sauerstoff oder Schwefel und
n = 0 oder 1 bedeuten.3. Compounds of formula I according to claims 1 or 2, wherein
R¹, R² independently of one another are hydrogen or (C₁-C₄) alkyl,
R¹ and R² optionally together part of a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 5 or 6 ring members,
R³ is hydrogen or halogen,
R⁴, R⁵, R⁶ independently of one another are hydrogen, halogen, (C₁-C₄) alkyl, (C₁-C₄) alkoxy or in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenoxy,
R³, R⁵ and R⁶ together form one or a part of a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroaromatics O, N or S with 5 to 7 ring members,
R⁷ = hydrogen or (C₁-C₄) alkyl,
R⁸ = hydrogen, (C₁-C₄) alkyl, (C₁-C₄) alkoxy, phenyl- (C₁-C₄) alkoxy or halogen,
R⁹ = hydrogen, (C₁-C₄) alkyl, perhalo (C₁-C₄) alkyl, (C₁-C₄) alkoxy- (C₁-C₄) alkyl or phenyl- (C₁-C₄) alkyl,
R⁸ and R⁹ optionally together a saturated or partially unsaturated carbocycle or heterocycle with the heteroaromatics having 5 to 6 ring members,
X = oxygen or sulfur and
n = 0 or 1 mean.
Hal = Cl oder Br und
R¹² = (C₁-C₄)Alkylthio, im Phenylteil durch Halogen, (C₁-C₄)Alkyl oder (C₁-C₄)Alkoxy gegebenenfalls substituiertes Phenyl(C₁-C₄)alkylthio oder den Rest III bedeuten, mit Verbindungen der Formel IV umsetzt und, falls R¹² eine von der Formel III abweichende Bedeutung hat, anschließend die erhaltenen Verbindungen im Rest R¹² oxidiert und die entstandenen Oxidationsprodukte mit Verbindungen der Formel V zu den Endprodukten der Formel I, worin R¹²=Rest der Formel III bedeutet, umsetzt und, wenn R³=H bedeutet, den Wasserstoff gegebenenfalls austauscht.5. A process for the preparation of compounds of formula I according to one or more of claims 1 to 4, characterized in that compounds of formula II wherein
Hal = Cl or Br and
R¹² = (C₁-C₄) alkylthio, in the phenyl part by halogen, (C₁-C₄) alkyl or (C₁-C₄) alkoxy optionally substituted phenyl (C₁-C₄) alkylthio or the rest III mean with compounds of formula IV implemented and, if R¹² has a meaning deviating from formula III, then the compounds obtained are oxidized in the rest of R¹² and the resulting oxidation products with compounds of formula V to the end products of the formula I, in which R 12 = radical of the formula III, and, if R 3 = H, optionally exchanges the hydrogen.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4029648A DE4029648A1 (en) | 1990-09-19 | 1990-09-19 | 4-ANILINO-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDES |
| ZA917428A ZA917428B (en) | 1990-09-19 | 1991-09-18 | 4-anilinopyrimidines,processes for their preparation,compositions containing them,and their use as fungicides |
| PCT/EP1991/001791 WO1992005158A1 (en) | 1990-09-19 | 1991-09-19 | 4-anilino-pyrimidines, process for producing the same, agents containing the same and their use as fungicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4029648A DE4029648A1 (en) | 1990-09-19 | 1990-09-19 | 4-ANILINO-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4029648A1 true DE4029648A1 (en) | 1992-03-26 |
Family
ID=6414525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4029648A Withdrawn DE4029648A1 (en) | 1990-09-19 | 1990-09-19 | 4-ANILINO-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDES |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE4029648A1 (en) |
| WO (1) | WO1992005158A1 (en) |
| ZA (1) | ZA917428B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981537A (en) * | 1993-11-12 | 1999-11-09 | Pharmacia & Upjohn Company | Pyrimidine-thioalkyl and alkylether compounds |
| US6197958B1 (en) * | 1994-10-14 | 2001-03-06 | Basf Aktiengesellschaft | Carboxylic acid derivatives, their preparation and use |
| WO2001081320A1 (en) * | 2000-04-19 | 2001-11-01 | Degussa Ag | 2-alkoxy-5-methoxypyrimidines or their tautomeric forms and methods for producing the same |
| US7205306B2 (en) * | 2001-05-14 | 2007-04-17 | Bristol-Myers Squibb Pharma Company | Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands |
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| KR100516434B1 (en) * | 2002-04-04 | 2005-09-22 | (주) 비엔씨바이오팜 | 6-(4-substituted-anilino)pyrimidine derivatives, method for preparing thereof and antiviral pharmaceutical composition comprising the same |
| CN1984660B (en) * | 2003-07-03 | 2010-12-15 | 美瑞德生物工程公司 | 4-Arylamino-quinazolines as caspase-specific activators and inducers of apoptosis |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| JP2009530288A (en) * | 2006-03-16 | 2009-08-27 | ノバルティス アクチエンゲゼルシャフト | Heterocyclic organic compounds, especially for the treatment of melanoma |
| WO2011032656A1 (en) | 2009-09-18 | 2011-03-24 | Bayer Cropscience Ag | 5-fluor-2-thio-substituted pyrimidine derivatives |
| CN113754633B (en) * | 2021-09-26 | 2023-05-05 | 中国农业大学 | 1- (6-substituted pyrimidine-4-yl) -1,2,3, 4-tetrahydroquinoline compound and preparation method and application thereof |
| CN114644596B (en) * | 2022-03-31 | 2024-01-30 | 青岛科技大学 | Fluoropyrimidine aromatic amine compound and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3974162A (en) * | 1972-12-21 | 1976-08-10 | American Home Products Corporation | 4-Pyrimidinylthioacetic acid derivatives |
| DK130584A (en) * | 1983-04-08 | 1984-10-09 | Ciba Geigy Ag | N- (2-NITROPHENYL) -4-AMINO-PYRIMIDINE DERIVATIVES AND THEIR PREPARATION AND USE AS MICROBICIDES |
| GR80171B (en) * | 1983-08-29 | 1985-01-02 | Ciba Geigy Ag | N-(2-nitrophenyl)-4-aminopyrimidine derivatives process for the preparation thereof and use |
| JPH02200678A (en) * | 1989-01-28 | 1990-08-08 | Kumiai Chem Ind Co Ltd | 2-iodopropargyloxypyrimidine derivative and agricultural and horticultural germicide |
-
1990
- 1990-09-19 DE DE4029648A patent/DE4029648A1/en not_active Withdrawn
-
1991
- 1991-09-18 ZA ZA917428A patent/ZA917428B/en unknown
- 1991-09-19 WO PCT/EP1991/001791 patent/WO1992005158A1/en not_active Ceased
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981537A (en) * | 1993-11-12 | 1999-11-09 | Pharmacia & Upjohn Company | Pyrimidine-thioalkyl and alkylether compounds |
| US6197958B1 (en) * | 1994-10-14 | 2001-03-06 | Basf Aktiengesellschaft | Carboxylic acid derivatives, their preparation and use |
| US7601730B2 (en) | 1994-10-14 | 2009-10-13 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US7863445B2 (en) | 1994-10-14 | 2011-01-04 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| USRE42462E1 (en) | 1994-10-14 | 2011-06-14 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| USRE42477E1 (en) | 1994-10-14 | 2011-06-21 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US8349843B2 (en) | 1994-10-14 | 2013-01-08 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| WO2001081320A1 (en) * | 2000-04-19 | 2001-11-01 | Degussa Ag | 2-alkoxy-5-methoxypyrimidines or their tautomeric forms and methods for producing the same |
| US6620932B2 (en) | 2000-04-19 | 2003-09-16 | Degussa Ag | 2-alkoxy-5-methoxypyrimidines or their tautomeric forms and methods for producing the same |
| US7205306B2 (en) * | 2001-05-14 | 2007-04-17 | Bristol-Myers Squibb Pharma Company | Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands |
| US7319100B2 (en) | 2001-05-14 | 2008-01-15 | Bristol-Myers Squibb Pharma Company | Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA917428B (en) | 1992-04-29 |
| WO1992005158A1 (en) | 1992-04-02 |
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