CA2068338A1 - Pyridine derivatives, process for making them, agents containing them and their use as fungicides - Google Patents
Pyridine derivatives, process for making them, agents containing them and their use as fungicidesInfo
- Publication number
- CA2068338A1 CA2068338A1 CA002068338A CA2068338A CA2068338A1 CA 2068338 A1 CA2068338 A1 CA 2068338A1 CA 002068338 A CA002068338 A CA 002068338A CA 2068338 A CA2068338 A CA 2068338A CA 2068338 A1 CA2068338 A1 CA 2068338A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- phenyl
- halogen
- alkylthio
- 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.)
- Abandoned
Links
- 239000000417 fungicide Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 title abstract description 11
- 150000003222 pyridines Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- -1 polymethylene chain Polymers 0.000 claims abstract description 45
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 42
- 150000002367 halogens Chemical class 0.000 claims abstract description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 150000005694 halopyrimidines Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000002463 imidates Chemical class 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 abstract description 16
- 125000004438 haloalkoxy group Chemical group 0.000 abstract description 9
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- 125000004660 phenylalkylthio group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 21
- 239000002904 solvent Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000008187 granular material Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 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 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 239000010949 copper Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 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
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001484259 Lacuna Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 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
- 230000015572 biosynthetic process Effects 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
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000005695 dehalogenation reaction 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
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 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
- 239000011737 fluorine Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 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 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VZPRFNYMFQEGNV-UHFFFAOYSA-N naphthalen-2-ylmethyl cyclopropanecarboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC(=O)C1CC1 VZPRFNYMFQEGNV-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
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- YATDSXRLIUJOQN-SVRRBLITSA-N (2,3,4,5,6-pentafluorophenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=C(F)C(F)=C1F YATDSXRLIUJOQN-SVRRBLITSA-N 0.000 description 1
- MYUPFXPCYUISAG-UHFFFAOYSA-N (2,4-dichlorophenyl)(phenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC(Cl)=CC=1)Cl)(O)C1=CC=CC=C1 MYUPFXPCYUISAG-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- LZTIMERBDGGAJD-SNAWJCMRSA-N (2e)-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)\C=C1/NCCCS1 LZTIMERBDGGAJD-SNAWJCMRSA-N 0.000 description 1
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 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
- 239000012071 phase Substances 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
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002335 preservative 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
- 239000000047 product Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 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
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 208000024891 symptom Diseases 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
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 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
- 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
- 150000003606 tin compounds Chemical group 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
- 125000005270 trialkylamine group Chemical group 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Floor Finish (AREA)
Abstract
Abstract of the disclosure Pyridine derivatives, process for their preparation, agents containing them and their use as fungicides Compounds of the formula I
Description
2~8338 .iOECHST AKTI~NGES2LLSCHAF~ ~OE 89/F 359 ~e~criptio7a ?yridine derivatives, process for their preparation, ~gents containing them and their use as fungicides The present invention relates to novel pyridine deriva-ti-~es, a process for their prepara~ion, agents containing them and their use as fungicides.
Pyridine derivatives are already known as acti~e components in fungicidal agents (cf. EP-A-270,362, EP-A 278,610, EP-A-259,139, EP-A 234,104). However, the action of these cornpounds is not always satisfactory, in particular at low application rates.
Novel pyridine derivatives have now been found which have advantageous effects in the control of a wide spectrum of phytopathogenic fungi, in particular at low dosages.
The present inven~ion therefore relates to the compounds of the formula I, ~5 ~ ~` R9 R~R 2 ~ 8 in which R1, R2, R3 and R4 are independently of one another, hydrogen, halogen, nitro, (C~-C4)alkyl, (Cl-C4~alkoxy, (cl-c4)alkylthio~ (Cl-C4)haloalkoxy or (C1 -C4 ) haloalkyl, R5, R6 and R7 are independently of one another hydrogen, (C1 C6)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to 2~33~
trisubstituted by halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4 ) haloalkyl, or (Cl-C4)haloalkoxy, R8 and R9 are independently of one another hydrogen, (C1-C6)alkyl, ( C3-C7 ) cycloalkyl, ( C3-C7 ) cycloalkyl-(C,-C4)alkyl, it being possible for the ~wo last-mentioned radicals to be monosu~stituted to trisubstituted in the cycloalkyl moiety by (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (Cl-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkylthio-(C1-C4)alkyl, halogen, (C2-C6)al-kenyl, (C2-C6)alkynyl, phenyl, phenoxy, phenoxy-(C1-C4)alkyl, phenylmercapto-(Cl-C4)alkyl, phenyl-mercapto, phenyl-(C1-C4)alkoxy or phenyl-(C1-C4)alkylthio, it being po~sible for the seven last-mentioned radical to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (Cl-C4)alkoxy, (C1 C4)alkylthio, (Cl-C4)haloalkyl or (C1-C4)haloalkoxy, or (c2-c4)alkenyloxy~
~C2-C4)alkynyloxy, (Cl-C4)haloalkoxy, (Cl-C4)alkoxy-(Cl-C4)alkoxy or (C1-C4)alkylthio-(C1-C4)alkylthio, Rl is hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C2-C6)-alkenyloxy, (C2-C6)alkynyloxy, (C1-C4)alkylthio, halogen, phenyl, it beinq possible for the phenyl radical to be monosubstituted to trisubstituted by halogen, nitro, cyano, (C1-C4)alkyl, (Cl-C4)alk-oxy, (C1-C4)alkylthio, (Cl-C4)haloalkyl or (Cl-C4)haloalkoxy, or 30 R8 and R10 together form a polymethylene chain of the formula -(CH2) m- where m = 3 - 4, Rl1 and R12 are independently of one another hydrogen or (C1-C4)alkyl, Y is N or -CRl and n is 1-3, and their acid addition salts.
The alkyl, alkenyl or alkynyl radicals here can be both straight-~hain and branched. Halogen is F, Cl, Br and I, preferably F, Cl and Br. The prefix "halo~' in the 2~833~
Pyridine derivatives are already known as acti~e components in fungicidal agents (cf. EP-A-270,362, EP-A 278,610, EP-A-259,139, EP-A 234,104). However, the action of these cornpounds is not always satisfactory, in particular at low application rates.
Novel pyridine derivatives have now been found which have advantageous effects in the control of a wide spectrum of phytopathogenic fungi, in particular at low dosages.
The present inven~ion therefore relates to the compounds of the formula I, ~5 ~ ~` R9 R~R 2 ~ 8 in which R1, R2, R3 and R4 are independently of one another, hydrogen, halogen, nitro, (C~-C4)alkyl, (Cl-C4~alkoxy, (cl-c4)alkylthio~ (Cl-C4)haloalkoxy or (C1 -C4 ) haloalkyl, R5, R6 and R7 are independently of one another hydrogen, (C1 C6)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to 2~33~
trisubstituted by halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4 ) haloalkyl, or (Cl-C4)haloalkoxy, R8 and R9 are independently of one another hydrogen, (C1-C6)alkyl, ( C3-C7 ) cycloalkyl, ( C3-C7 ) cycloalkyl-(C,-C4)alkyl, it being possible for the ~wo last-mentioned radicals to be monosu~stituted to trisubstituted in the cycloalkyl moiety by (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (Cl-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkylthio-(C1-C4)alkyl, halogen, (C2-C6)al-kenyl, (C2-C6)alkynyl, phenyl, phenoxy, phenoxy-(C1-C4)alkyl, phenylmercapto-(Cl-C4)alkyl, phenyl-mercapto, phenyl-(C1-C4)alkoxy or phenyl-(C1-C4)alkylthio, it being po~sible for the seven last-mentioned radical to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (Cl-C4)alkoxy, (C1 C4)alkylthio, (Cl-C4)haloalkyl or (C1-C4)haloalkoxy, or (c2-c4)alkenyloxy~
~C2-C4)alkynyloxy, (Cl-C4)haloalkoxy, (Cl-C4)alkoxy-(Cl-C4)alkoxy or (C1-C4)alkylthio-(C1-C4)alkylthio, Rl is hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C2-C6)-alkenyloxy, (C2-C6)alkynyloxy, (C1-C4)alkylthio, halogen, phenyl, it beinq possible for the phenyl radical to be monosubstituted to trisubstituted by halogen, nitro, cyano, (C1-C4)alkyl, (Cl-C4)alk-oxy, (C1-C4)alkylthio, (Cl-C4)haloalkyl or (Cl-C4)haloalkoxy, or 30 R8 and R10 together form a polymethylene chain of the formula -(CH2) m- where m = 3 - 4, Rl1 and R12 are independently of one another hydrogen or (C1-C4)alkyl, Y is N or -CRl and n is 1-3, and their acid addition salts.
The alkyl, alkenyl or alkynyl radicals here can be both straight-~hain and branched. Halogen is F, Cl, Br and I, preferably F, Cl and Br. The prefix "halo~' in the 2~833~
description of a substituent here and in the following means that this substituent can occur once or several times with the s~ne or a different meaning. The prefix 'halo" comprises fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine. Examples of haloalkyl which may be mentioned are: CF3, CF2CHF2, CF2CF3, CC13, CC12F, CFzCF2CF3~ CF2CHFCF3 and (CF2)3CF3- ExampleS of haloalkoxy are OCF3, OCF2CHF2 or OCF2CF2CF3.
Preferred compounds of the formula I are those in which Rl, R2, R3 and R4 are independently of one another hydro-qen, halogen, (C1-C2)haloalkyl or (C1-C3)alkyl, R5 and R6 are independently of one another hydrogen, ~C1-C3)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to trisub-stituted by halogen or (C1-C4)alkyl, R7 is hydrogen, R3 and R9 are independently of one another hydrogen, (Cl-C6)alkyl, (C3-C6jcycloalkyl, (Cs-C6)cycloalkyl-(C1-C3~alkyl, halogen, phenyl which can be mono-substituted to tri~ubstituted by halogen, (C1-C4)alkyl or (Cl-C4)alkoxy, or (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, ( C~-C4 ) haloalkoxy or ( Cl-c4 ) alk-oxy-(C1-C4)alkoxy R10 is hydrogen, (C1-C4)alkyl, halogen, phenyl, it being possible for the phenyl radical to be monosubstituted to trisubstituted by halogen or (Cl-C3)alkyl, or (C1 C3 ) alkoxy or R3 and R10 together form a polymethylene chain of the formula -(CH2) m~ where m - 3 - 4, Rl1 and Rl2 are hydrogen, Y is N or -CR10 and n = 1, and their acid addition salts.
The following acids are suitable for the preparation of the acid addition salts of the compounds of the formula I:
hydrohalic acid such as hydrochloric acid or hydrobromic 20~8338 acid, and in addition phosphoric acid, nitric acid, sulfuric acid, mono or bifunctional carboxylic acids and hydroxycarboxylic acids such as ~cetic 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-naphthalene-disulfonic acid. The acid addition salts of the compounds of the formula I can be obtained in a simple manner by customary salt formation methods, for example by dis-solving a compound of the formula I in a suitable organic solvent and adding the acid and are isolated in a known manner, for example by filtering off, and, if desired, purified by washing with an inert organic solvent.
The present invention also relates to a process for the preparation of the compounds of the formula I.
These compounds can be prepared by the following variants:
1~ Pyridine derivatives of the formula I where R9 = H
and Y = -CR10 can be obtained by reductive dehalogen-ation of appropriate halopyrimidines of the formula I in which R9 - halogen (for example Cl, Br, or I) and the remaining substituents are as defined in formula I.
The dehalogenation can be carried out with hydrogen in the presence of catalysts (for example palladium/carbon) in an inert solvent, for example water, lower alcohol (such as methanol and ethanol), ethyl acetate or toluene or mixtures thereof. The addition of base~ such as alkali metal hydroxides or alkali metal carbonates or alkaline earth metal hydroxides or alkaline earth metal carbonates is advantageous. The reaction i~ carried out in the range 15-60C under a pressure of 1 to 5 bar.
2) Pyridine derivatives of the -formula I, in which R9 2~83~
is (C~-C4)alkoxy, (Cl-C4)alkylthio, phenoxy, phenyl-mercapto,phenyl-(C1-C4)alkoxyorphenyl-(Cl-C4)alkyl thio, it being possible for the 4 last-mentioned radicals in the phenyl moiety to be mono~ubstituted to trisubstituted by halogen, nitro, cyano, (Cl-C4)alkyl, (Cl-C4)alkoxy, (C1-C4)alkylthio, (Cl-4)haloalkylor(C1-C4)haloalkoxy,or(C2-C4)alkenyl-oxy (C2-C4)alkynyloxy, ( C~-C4 ) haloalkoxy, (C1-C4)alk-oxy-(Cl-C4)alkoxy or(C1-C4)alkylthio-(C1-C4)alkylthio and Y is -CRl, can be prepared by reaction of the appropriate halopyrimidines I (R9 = halogen) with an alkali metal compound of the formula II RaM (II), in which R9 has the abovementioned meaning and M is an alkali metal (for example Li, Na or K).
The reaction can be carried out between 0~C and 130C in the course of 0.5 h to 72 h. The alkali metal compound (II) can be employed in amounts of 1 to 2 mol equivalents relative to 1 equivalent of the halopyrimidine (I) (R9 = halo~en). The reaction is usually carried out in the presence of a solvent.
In the cases in which an alkali metal compound R9M
is employed in which R9 is (Cl-C4)alkoxy, phenyl-(C1-C4)alkoxy, (C2~C4)alkenyloxyl (C2-C4)-alkynyloxy, (C1-C4)haloalkoxy or (C1-C4)alkoxy-(Cl-C4)alkoxy, the corresponding alcohol R9OH or an ether (for example diethyl ether, dioxane or tetrahydrofuran) or a mixture thereof is used as the solvent.
In the cases in which an alkali metal compound is employed in which R9 is (Cl-C4)alkylthio, phenoxy, phenylmercapto, phenyl-(Cl-C4)alkoxy or phenyl-(C1-C4)alkylthio, an ether (for example diethyl ether, dioxane or tetrahydrofuran), a nitrile (for example acetonitrile), an aromatic hydrocar~on (for example toluene or xylene) or a mixture thereof is used as the solvent.
~g338 3) Pyridlne derivatives of the formula I, in which R9 is (Cl-C6)alkyl, ( C3-c7 ) cycloalkyl, 1 C3-C7 ) cycloalkyl-(cl-c4)alkyl~(cl~c4)alkoxy-(cl-c4)alkylr(cl-c4)alkyl-thio-(Cl-C4)alkyl or phenyl, it being possible for the last-mentioned radical to be monosubstituted to trisubstituted by (Cl-C4)alkyl or (Cl-C4)alkoxy, and Y is -CR10, can be obtained by reaction of appropri-ate halopyrimidines I (R9 = halogen) with Grignard compounds R9MgX (III), where R9 is defined a~ indi-cated above and X is halogen (Cl, Br or I), in the presence of nickel-phosphine complexes such as, for example, 1,2-bi~(diphenylphosphino)ethane-nickel(II) chloride or 1,3-bis(diphenylphosphino)propane-nickel(II) chloride (cf. Chem. Pharm. Bull. 26, 2160 (1978)).
The reaction can be carried out in the course of 2 - 48 h between 0C and 80C or at the boiling point of the solvent. The Grignard compound R9MgX is in this case employed in amounts of 1-2.5 mol equivalents relative to 1 equivalent of halo-pyrimidine (I). Suitable solvents are ethers such as, for example, diethyl ether, THF, dioxane and dime~hoxyethane.
The halopyrimidines I (R9 = halogen) can be obtained by reaction of the appropriate hydroxypyrimidines (I), in which R9 is the radical OH and the other substituents have the meanings as in formula I, with halogenating agents. Halogenating agents which can be employed are, for example, thionyl chloride, phosgene, phosphorus oxychloride, phosphorus pen-tachloride, phosphorus oxybromide or phosphorus tribromide. The reactions can be carried out in a solvent, but also without solvent. The halogenating agent is employed in amounts of 1 to ~ equivalents relative to 1 equivalent of the hydroxypyrimidine lI) (R9 = 0~). The reactions can be carried out in a temperature range from 25 to 160C. Solvents used ~0~833~
are, for example, aromatic hydrocarbons (for example benzene or toluene, inter alia) or halogenated hydrocarbons (for example chlorobenzene).
The hydroxypyrimidines (I) (R9 = OH) can be prepared by condensation of the amidine derivatives (IV) with ~-oxocarboxylates V
; - _7 .. I `
;.; ~R
' - _ 3 ? ^ 2 :~3 :~
. ~
I~ V
in which Rl-R8, R10-Rl2 and n are as defined in formula I, X is halogen (for example chlorine, bromine or iodine) and Rl3 is lower alkyl radicals such as methyl, ethyl and propyl.
The reactions are carried out in the temperature range from 20 to 110C within the course of 2 - 72 h. The ~-oxocarboxylate (V) can be employed in amounts of 1 - 1.5 equivalents relative to 1 equivalent of amidine derivative (IV). The reaction is carried out in the presence of a base and of a solvent. Bases used can be, for example, inorganic bases such as alkali metal hydroxide6 and carbonates or organic ba~es such as ~odium alkoxides, trialkylamines and N,N-dialkylanilines. Solvents used are lower alcohols (such as methanol and ethanol), cyclic ethers (such as dioxane and THF), pyridine, N,N-dimethylformamide, water or mixtures thereof. The amidine derivatives t~V) and the ~oxocarboxy:Late~ can be prepared by proces6es known per se (cf. J. Org. Chem. 32, 1591 (1967) and ~8~3~
S~-~nthesis 1982, 451 and Organikum 1986, 516 et seq.).
Preferred compounds of the formula I are those in which Rl, R2, R3 and R4 are independently of one another hydro-qen, halogen, (C1-C2)haloalkyl or (C1-C3)alkyl, R5 and R6 are independently of one another hydrogen, ~C1-C3)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to trisub-stituted by halogen or (C1-C4)alkyl, R7 is hydrogen, R3 and R9 are independently of one another hydrogen, (Cl-C6)alkyl, (C3-C6jcycloalkyl, (Cs-C6)cycloalkyl-(C1-C3~alkyl, halogen, phenyl which can be mono-substituted to tri~ubstituted by halogen, (C1-C4)alkyl or (Cl-C4)alkoxy, or (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, ( C~-C4 ) haloalkoxy or ( Cl-c4 ) alk-oxy-(C1-C4)alkoxy R10 is hydrogen, (C1-C4)alkyl, halogen, phenyl, it being possible for the phenyl radical to be monosubstituted to trisubstituted by halogen or (Cl-C3)alkyl, or (C1 C3 ) alkoxy or R3 and R10 together form a polymethylene chain of the formula -(CH2) m~ where m - 3 - 4, Rl1 and Rl2 are hydrogen, Y is N or -CR10 and n = 1, and their acid addition salts.
The following acids are suitable for the preparation of the acid addition salts of the compounds of the formula I:
hydrohalic acid such as hydrochloric acid or hydrobromic 20~8338 acid, and in addition phosphoric acid, nitric acid, sulfuric acid, mono or bifunctional carboxylic acids and hydroxycarboxylic acids such as ~cetic 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-naphthalene-disulfonic acid. The acid addition salts of the compounds of the formula I can be obtained in a simple manner by customary salt formation methods, for example by dis-solving a compound of the formula I in a suitable organic solvent and adding the acid and are isolated in a known manner, for example by filtering off, and, if desired, purified by washing with an inert organic solvent.
The present invention also relates to a process for the preparation of the compounds of the formula I.
These compounds can be prepared by the following variants:
1~ Pyridine derivatives of the formula I where R9 = H
and Y = -CR10 can be obtained by reductive dehalogen-ation of appropriate halopyrimidines of the formula I in which R9 - halogen (for example Cl, Br, or I) and the remaining substituents are as defined in formula I.
The dehalogenation can be carried out with hydrogen in the presence of catalysts (for example palladium/carbon) in an inert solvent, for example water, lower alcohol (such as methanol and ethanol), ethyl acetate or toluene or mixtures thereof. The addition of base~ such as alkali metal hydroxides or alkali metal carbonates or alkaline earth metal hydroxides or alkaline earth metal carbonates is advantageous. The reaction i~ carried out in the range 15-60C under a pressure of 1 to 5 bar.
2) Pyridine derivatives of the -formula I, in which R9 2~83~
is (C~-C4)alkoxy, (Cl-C4)alkylthio, phenoxy, phenyl-mercapto,phenyl-(C1-C4)alkoxyorphenyl-(Cl-C4)alkyl thio, it being possible for the 4 last-mentioned radicals in the phenyl moiety to be mono~ubstituted to trisubstituted by halogen, nitro, cyano, (Cl-C4)alkyl, (Cl-C4)alkoxy, (C1-C4)alkylthio, (Cl-4)haloalkylor(C1-C4)haloalkoxy,or(C2-C4)alkenyl-oxy (C2-C4)alkynyloxy, ( C~-C4 ) haloalkoxy, (C1-C4)alk-oxy-(Cl-C4)alkoxy or(C1-C4)alkylthio-(C1-C4)alkylthio and Y is -CRl, can be prepared by reaction of the appropriate halopyrimidines I (R9 = halogen) with an alkali metal compound of the formula II RaM (II), in which R9 has the abovementioned meaning and M is an alkali metal (for example Li, Na or K).
The reaction can be carried out between 0~C and 130C in the course of 0.5 h to 72 h. The alkali metal compound (II) can be employed in amounts of 1 to 2 mol equivalents relative to 1 equivalent of the halopyrimidine (I) (R9 = halo~en). The reaction is usually carried out in the presence of a solvent.
In the cases in which an alkali metal compound R9M
is employed in which R9 is (Cl-C4)alkoxy, phenyl-(C1-C4)alkoxy, (C2~C4)alkenyloxyl (C2-C4)-alkynyloxy, (C1-C4)haloalkoxy or (C1-C4)alkoxy-(Cl-C4)alkoxy, the corresponding alcohol R9OH or an ether (for example diethyl ether, dioxane or tetrahydrofuran) or a mixture thereof is used as the solvent.
In the cases in which an alkali metal compound is employed in which R9 is (Cl-C4)alkylthio, phenoxy, phenylmercapto, phenyl-(Cl-C4)alkoxy or phenyl-(C1-C4)alkylthio, an ether (for example diethyl ether, dioxane or tetrahydrofuran), a nitrile (for example acetonitrile), an aromatic hydrocar~on (for example toluene or xylene) or a mixture thereof is used as the solvent.
~g338 3) Pyridlne derivatives of the formula I, in which R9 is (Cl-C6)alkyl, ( C3-c7 ) cycloalkyl, 1 C3-C7 ) cycloalkyl-(cl-c4)alkyl~(cl~c4)alkoxy-(cl-c4)alkylr(cl-c4)alkyl-thio-(Cl-C4)alkyl or phenyl, it being possible for the last-mentioned radical to be monosubstituted to trisubstituted by (Cl-C4)alkyl or (Cl-C4)alkoxy, and Y is -CR10, can be obtained by reaction of appropri-ate halopyrimidines I (R9 = halogen) with Grignard compounds R9MgX (III), where R9 is defined a~ indi-cated above and X is halogen (Cl, Br or I), in the presence of nickel-phosphine complexes such as, for example, 1,2-bi~(diphenylphosphino)ethane-nickel(II) chloride or 1,3-bis(diphenylphosphino)propane-nickel(II) chloride (cf. Chem. Pharm. Bull. 26, 2160 (1978)).
The reaction can be carried out in the course of 2 - 48 h between 0C and 80C or at the boiling point of the solvent. The Grignard compound R9MgX is in this case employed in amounts of 1-2.5 mol equivalents relative to 1 equivalent of halo-pyrimidine (I). Suitable solvents are ethers such as, for example, diethyl ether, THF, dioxane and dime~hoxyethane.
The halopyrimidines I (R9 = halogen) can be obtained by reaction of the appropriate hydroxypyrimidines (I), in which R9 is the radical OH and the other substituents have the meanings as in formula I, with halogenating agents. Halogenating agents which can be employed are, for example, thionyl chloride, phosgene, phosphorus oxychloride, phosphorus pen-tachloride, phosphorus oxybromide or phosphorus tribromide. The reactions can be carried out in a solvent, but also without solvent. The halogenating agent is employed in amounts of 1 to ~ equivalents relative to 1 equivalent of the hydroxypyrimidine lI) (R9 = 0~). The reactions can be carried out in a temperature range from 25 to 160C. Solvents used ~0~833~
are, for example, aromatic hydrocarbons (for example benzene or toluene, inter alia) or halogenated hydrocarbons (for example chlorobenzene).
The hydroxypyrimidines (I) (R9 = OH) can be prepared by condensation of the amidine derivatives (IV) with ~-oxocarboxylates V
; - _7 .. I `
;.; ~R
' - _ 3 ? ^ 2 :~3 :~
. ~
I~ V
in which Rl-R8, R10-Rl2 and n are as defined in formula I, X is halogen (for example chlorine, bromine or iodine) and Rl3 is lower alkyl radicals such as methyl, ethyl and propyl.
The reactions are carried out in the temperature range from 20 to 110C within the course of 2 - 72 h. The ~-oxocarboxylate (V) can be employed in amounts of 1 - 1.5 equivalents relative to 1 equivalent of amidine derivative (IV). The reaction is carried out in the presence of a base and of a solvent. Bases used can be, for example, inorganic bases such as alkali metal hydroxide6 and carbonates or organic ba~es such as ~odium alkoxides, trialkylamines and N,N-dialkylanilines. Solvents used are lower alcohols (such as methanol and ethanol), cyclic ethers (such as dioxane and THF), pyridine, N,N-dimethylformamide, water or mixtures thereof. The amidine derivatives t~V) and the ~oxocarboxy:Late~ can be prepared by proces6es known per se (cf. J. Org. Chem. 32, 1591 (1967) and ~8~3~
S~-~nthesis 1982, 451 and Organikum 1986, 516 et seq.).
4) Pyridine derivatives of the formula (I), in which R~
= R9 and is (Cl-C4)alkyl, phenyl-(C1-C4)alkyl or phenyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, [lacuna]
(C1-C4)alkyl, (Cl-C4)alkoxy, (Cl-C4)alkylthio, (Cl-C4)haloalkyl or (C1-C4)haloalkoxy, and Y is N, can be prepared by reaction of the amidine derivatives IV with an imidate derivative of the formula VI in which R9 [sic]
?~ C~ 3 (VI), has the abovementioned meaning and R13 is as defined in formula v (cf. also JOC 27, 3608 (1962~).
lS The reaction can be carried out in the presence of a solvent or, alternatively, without solvent.
Suitable solvents are lower alcohols such as methanol and ethanol. The reaction is carried out in the temperature range from 10C to 100C. The imidate derivative (VI) can be employed in amounts of 2 to 5 equivalents relative to 1 equivalent of amidine derivative IV.
The compounds of the formula (I) according to the inven-tion are distinguished by an excellent fungicidal action.
Causative organisms of fungal disease which have already penetrated into the plant tissue can be successfully controlled in a curative manner~ This is particularly important and advantageous in those fungal diseases which, after infection has occurred, can no longer be controlled effectively with the otherwise customary ~68338 funaicides. The spectrum of action of the compounds claimed includes a plurality of various economically important phytopathogenic fungi, such as, for example, Piricularla oryzae, Venturia inaequalis, Cercospora beticola, powdery mildew species, Fusarium species, Plasmopora viticola, Pseudoperonospra cubensis [sic], Leptosphaeria nodorum, Drechslera, various rust fungi and Pseudocercosporella herpotrichoides. Benzimidazole- and dicarboximide- sensitive and -resistant Boytritis cinerea [sic] strains are particularly well controlled.
The compounds according to the invention are in addition also suitable for use in industrial fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metal processing or as preserva-tives in drilling and cutting oils.
The invention also relates to agents which contain thecompounds of the formula I in addition to suitable formulation auxiliaries.
The agents according to the invention in general contain the active compounds of the formula I in amounts of 1 to 95% by weight.
They can be variously formulated, depending on how it is prespecified by the biological and/or physicochemical parameters. Suita~le formulation possibilities are therefore:
Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions ~SC), emulsions, sprayable solutions, dispersions having an oil or water base (SC), ~uspo-emulsions (SC), dusting agents (DP), seed dressings, granules in the form of micro-, spray, absorption and adsorption granules, water-dispersible granules (WG), ULV
formulations, microcapsules, waxes or baits.
These individual formulation types are known in principle 2~833~
and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie" (Chemical Technology), Volume 7, C- Hauser Verlag Munich, 4th Ed. 1986; van Falkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed.
1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed.
1979, G. Goodwin Ltd. London.
The formulation auxiliaries required such as inert materials, surfactants, solvents and other additives are likewise known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carriers , 2nd Ed., Darland Books, Caldwell N.J.; H.Y.
Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y.; Marschen [sic], "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon'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;
Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte"
(Surface-active ethylene oxide adducts), Wiss.
Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie~ (Chemical Technology), Volume /, C. ~auser Verlag Munich, 4th Ed. 1986.
On the basis of these formulations, combinations with other pesticidally active substances, fertilizers and/or gro~th regulators can also be prepared, for example in the form of a finished formulation or as a tank mix.
Wettable powders are preparations which can be uniformly dispersed in water and, apart from the active compound and a diluent or inert substance, additionally contain wetting agents, for example polyoxyethylated alkyl-phenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates and dispersing agents, for example sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6r6'-disulfonate, sodium dibutylnaphthalenesulfonate or, alternatively, sodium oleylmethyltaurate. Emulsifiable ; concentrates are prepared by dissolving the active 2~3C~8 compound in an organic solvent, ~or example butanol, cyclohexanone, dimethylformamide, xylene or, alter-natively, higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. Examples of emulsifiers which can be used are.
alkylarylsulfonic acid calcium salts such as Ca dodecyl-benzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl pol~glycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide [lacuna] sorbitan fatty acid esters, polyoxy-ethylene sorbitan fatty acid esters or polyoxyethylene sorbitol e~ters.
Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, poryphillite [sic] or diatomaceous earth. Granules can either be prepared by spraying the active compound onto adsorptive granulated inert material or by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or, alternatively, mineral oils, to the surface of support substances such as sand or kaolinites or of granulated inert material. Suitable active compounds can also be granulated in the customary manner for the pre~aration of fertilizer granules - if desired mixed with fertilizers.
In wettable powders the active compound concentration is, ~or exarnple, about 10 to 90% by weight, the remainder to 100~ by weight is composed of customary formulat.ion com-ponents. In the case of emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations contain mostly 5 to 20~ by weight of active compound, sprayable solutions about 2 to 20~ by weight of active compound. In the case of granules, the active compound content partially depends on whether the active compound is liquid or solid and which granulation auxiliaries, fillers etc. are used.
20~8~3~
In addition, said active compound formulations optionally contain the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, filler~ or support substances customary in each ca~e.
For application, the concentrates present in commercial form are optionally diluted in a customary manner, for example by means of water in the case of wettable pow^
ders, emulsifiable concentrates, dispersions and some-times even in the case of microgranulates. Dust-like and granulated preparations, and sprayable solutions are customarily not diluted further with other inert substan-ces before application.
The application rate required varies with the external conditions such as temperature, humidity and the like. It can vary within wide limits, for example between 0.005 and 10.0 kg/ha or more of active substance, but it is preferably between 0.01 and 5 k~/ha.
The active compounds according to the invention in their commercial formulations can be applied either alone or in combination with other fungicides known from the litera-ture.
Examples of fungicides known from the literature which, according to the invention, can be combined with the compounds of the formula I are the following products:
imazalil, prochloraz, fenapanil, SSF 105, triflumizol, PP 969, flutriafol, BAY-ME~ 6401, propiconazole, etaconazole, diclobutrazol, bitertanol, triadimefon, triadimenol, fluotrimazole, tridemorph, dodemorph, fenpropimorph, falimorph, S-32165, chlobenzthiazone, parinol, buthio~ate, fenpropidin, triforine, fenarimol, nuarimol, triarimol, ethirimol, dimethirimol, bupirimate, rabenzazole, tricyclazole, fluobenzimine, pyroxyfur, NK-483, PP~389, pyroquilon, hymexazole, fenitropan, UHF-8227, cymoxanil, dichlorunanid [sic], captafol, captan, folpet, tolylfluanid, chlorothaloni], 2~3~8 etridiazole, iprodione ~formula II), procymidone, vinclozolin, metomeclan, myclozolin, dichlozolinate, fluorimide, drazoxolan, quinomethionate, nitrothal-i~opropyl, dithianon, dinocap, binapacryl, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, pyracarbolid, methfuroxam, ~enfura [sic], furmecyclox, benodanil, mebenil, mepronil, flutalanil, fuberidazole, thiabendazole, carbendazim, benomyl, thiofante [sic], thiofanate-methyl [sic], CGD-94340 F, IKF-1216, mancozeb, maneb, zineb, nabam, thiram, probineb, prothiocarb, propamocarb, dodine, guazatine, dicloran, quintozene, chloroneb, tecnazene, biphenyl, ~nilazlne, 2-phenylphenol, copper compounds such as Cu oxychloride, oxine Cu, Cu oxides, sulfur, fosetylaluminum [sic], sodium dodecylbenzenesulfonate, sodium dodecyl sulfate, sodium C13/C15 alcohol ether sulfonate, sodium cetostearylphosphate ester, dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfcnate, cetyltrimethylammonium chloride, Salts of long-chain primary, secondary or tertiary amines, alkylpropylenamines, laurylpyridinium bromide, ethoxylated quaternized fatty amines, alkyldimethyl-benzylammonium chloride and 1-hydroxyethyl-2-alkylimid-azoline.
The abovementioned combination components are known active compounds, many of which are described in CH [sic].~. Worthing, U. [sic]S.B. Walker, ~The Pesticide Manual", 7th Edition (1983), British Crop Protection Council.
The active compounds according to the invention, in particular those of the examples mentioned, can in addition be present in their commercial formulations and 3 3 ~
in the application forms prepared from these formulations mixed with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fun gicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin cornpounds, substances produced by microorganisms and the like. Preferred mixture components are:
1. from the phosphoric acid ester group azinphos-2 ethyl, azinphos-2 methyl, 1-(4-chloro-phenyl)-4-(O-ethyl, S-propyl)phosphoryl-oxypyrazole (TIA-230), chlorpyrifos, coumaphos, demeton, demeton-S-methyl, diazinon, dichlorvo~, dimethoate, ethoprophos, etrimfos, fenitrothion, fenthion, heptenophos, parathion, parathion-methyl, phosalone, pirimiphos-ethyl, pirimiphos-methyl, profenof GS, prothiofos, sulprofos, triazophos or trichlorophon.
2. from the carbamate group aldicarb, bendiocarb, BPMC (2-(1-methylpropyl)-phenylmethyl carbamate), butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, primicarb[sic], promecarb, propoxur or thiodicarb.
3. from the carboxylic acid ester group . 25 allethrin, alphamethrin, bioallethrin, : bioresmethrin, cycloprothrin, cyfluthrin, . cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl 2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)-cyclopropanecarboxy-late (FMC 54800), fenpropathrin, fenfluthrin, fen-valerate, flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin or tralomethrin.
4. from the formamidine group amitraz or chlordimeform 2 ~ 3 ~
= R9 and is (Cl-C4)alkyl, phenyl-(C1-C4)alkyl or phenyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, [lacuna]
(C1-C4)alkyl, (Cl-C4)alkoxy, (Cl-C4)alkylthio, (Cl-C4)haloalkyl or (C1-C4)haloalkoxy, and Y is N, can be prepared by reaction of the amidine derivatives IV with an imidate derivative of the formula VI in which R9 [sic]
?~ C~ 3 (VI), has the abovementioned meaning and R13 is as defined in formula v (cf. also JOC 27, 3608 (1962~).
lS The reaction can be carried out in the presence of a solvent or, alternatively, without solvent.
Suitable solvents are lower alcohols such as methanol and ethanol. The reaction is carried out in the temperature range from 10C to 100C. The imidate derivative (VI) can be employed in amounts of 2 to 5 equivalents relative to 1 equivalent of amidine derivative IV.
The compounds of the formula (I) according to the inven-tion are distinguished by an excellent fungicidal action.
Causative organisms of fungal disease which have already penetrated into the plant tissue can be successfully controlled in a curative manner~ This is particularly important and advantageous in those fungal diseases which, after infection has occurred, can no longer be controlled effectively with the otherwise customary ~68338 funaicides. The spectrum of action of the compounds claimed includes a plurality of various economically important phytopathogenic fungi, such as, for example, Piricularla oryzae, Venturia inaequalis, Cercospora beticola, powdery mildew species, Fusarium species, Plasmopora viticola, Pseudoperonospra cubensis [sic], Leptosphaeria nodorum, Drechslera, various rust fungi and Pseudocercosporella herpotrichoides. Benzimidazole- and dicarboximide- sensitive and -resistant Boytritis cinerea [sic] strains are particularly well controlled.
The compounds according to the invention are in addition also suitable for use in industrial fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metal processing or as preserva-tives in drilling and cutting oils.
The invention also relates to agents which contain thecompounds of the formula I in addition to suitable formulation auxiliaries.
The agents according to the invention in general contain the active compounds of the formula I in amounts of 1 to 95% by weight.
They can be variously formulated, depending on how it is prespecified by the biological and/or physicochemical parameters. Suita~le formulation possibilities are therefore:
Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions ~SC), emulsions, sprayable solutions, dispersions having an oil or water base (SC), ~uspo-emulsions (SC), dusting agents (DP), seed dressings, granules in the form of micro-, spray, absorption and adsorption granules, water-dispersible granules (WG), ULV
formulations, microcapsules, waxes or baits.
These individual formulation types are known in principle 2~833~
and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie" (Chemical Technology), Volume 7, C- Hauser Verlag Munich, 4th Ed. 1986; van Falkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed.
1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed.
1979, G. Goodwin Ltd. London.
The formulation auxiliaries required such as inert materials, surfactants, solvents and other additives are likewise known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carriers , 2nd Ed., Darland Books, Caldwell N.J.; H.Y.
Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y.; Marschen [sic], "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon'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;
Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte"
(Surface-active ethylene oxide adducts), Wiss.
Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie~ (Chemical Technology), Volume /, C. ~auser Verlag Munich, 4th Ed. 1986.
On the basis of these formulations, combinations with other pesticidally active substances, fertilizers and/or gro~th regulators can also be prepared, for example in the form of a finished formulation or as a tank mix.
Wettable powders are preparations which can be uniformly dispersed in water and, apart from the active compound and a diluent or inert substance, additionally contain wetting agents, for example polyoxyethylated alkyl-phenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates and dispersing agents, for example sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6r6'-disulfonate, sodium dibutylnaphthalenesulfonate or, alternatively, sodium oleylmethyltaurate. Emulsifiable ; concentrates are prepared by dissolving the active 2~3C~8 compound in an organic solvent, ~or example butanol, cyclohexanone, dimethylformamide, xylene or, alter-natively, higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. Examples of emulsifiers which can be used are.
alkylarylsulfonic acid calcium salts such as Ca dodecyl-benzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl pol~glycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide [lacuna] sorbitan fatty acid esters, polyoxy-ethylene sorbitan fatty acid esters or polyoxyethylene sorbitol e~ters.
Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, poryphillite [sic] or diatomaceous earth. Granules can either be prepared by spraying the active compound onto adsorptive granulated inert material or by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or, alternatively, mineral oils, to the surface of support substances such as sand or kaolinites or of granulated inert material. Suitable active compounds can also be granulated in the customary manner for the pre~aration of fertilizer granules - if desired mixed with fertilizers.
In wettable powders the active compound concentration is, ~or exarnple, about 10 to 90% by weight, the remainder to 100~ by weight is composed of customary formulat.ion com-ponents. In the case of emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations contain mostly 5 to 20~ by weight of active compound, sprayable solutions about 2 to 20~ by weight of active compound. In the case of granules, the active compound content partially depends on whether the active compound is liquid or solid and which granulation auxiliaries, fillers etc. are used.
20~8~3~
In addition, said active compound formulations optionally contain the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, filler~ or support substances customary in each ca~e.
For application, the concentrates present in commercial form are optionally diluted in a customary manner, for example by means of water in the case of wettable pow^
ders, emulsifiable concentrates, dispersions and some-times even in the case of microgranulates. Dust-like and granulated preparations, and sprayable solutions are customarily not diluted further with other inert substan-ces before application.
The application rate required varies with the external conditions such as temperature, humidity and the like. It can vary within wide limits, for example between 0.005 and 10.0 kg/ha or more of active substance, but it is preferably between 0.01 and 5 k~/ha.
The active compounds according to the invention in their commercial formulations can be applied either alone or in combination with other fungicides known from the litera-ture.
Examples of fungicides known from the literature which, according to the invention, can be combined with the compounds of the formula I are the following products:
imazalil, prochloraz, fenapanil, SSF 105, triflumizol, PP 969, flutriafol, BAY-ME~ 6401, propiconazole, etaconazole, diclobutrazol, bitertanol, triadimefon, triadimenol, fluotrimazole, tridemorph, dodemorph, fenpropimorph, falimorph, S-32165, chlobenzthiazone, parinol, buthio~ate, fenpropidin, triforine, fenarimol, nuarimol, triarimol, ethirimol, dimethirimol, bupirimate, rabenzazole, tricyclazole, fluobenzimine, pyroxyfur, NK-483, PP~389, pyroquilon, hymexazole, fenitropan, UHF-8227, cymoxanil, dichlorunanid [sic], captafol, captan, folpet, tolylfluanid, chlorothaloni], 2~3~8 etridiazole, iprodione ~formula II), procymidone, vinclozolin, metomeclan, myclozolin, dichlozolinate, fluorimide, drazoxolan, quinomethionate, nitrothal-i~opropyl, dithianon, dinocap, binapacryl, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, pyracarbolid, methfuroxam, ~enfura [sic], furmecyclox, benodanil, mebenil, mepronil, flutalanil, fuberidazole, thiabendazole, carbendazim, benomyl, thiofante [sic], thiofanate-methyl [sic], CGD-94340 F, IKF-1216, mancozeb, maneb, zineb, nabam, thiram, probineb, prothiocarb, propamocarb, dodine, guazatine, dicloran, quintozene, chloroneb, tecnazene, biphenyl, ~nilazlne, 2-phenylphenol, copper compounds such as Cu oxychloride, oxine Cu, Cu oxides, sulfur, fosetylaluminum [sic], sodium dodecylbenzenesulfonate, sodium dodecyl sulfate, sodium C13/C15 alcohol ether sulfonate, sodium cetostearylphosphate ester, dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfcnate, cetyltrimethylammonium chloride, Salts of long-chain primary, secondary or tertiary amines, alkylpropylenamines, laurylpyridinium bromide, ethoxylated quaternized fatty amines, alkyldimethyl-benzylammonium chloride and 1-hydroxyethyl-2-alkylimid-azoline.
The abovementioned combination components are known active compounds, many of which are described in CH [sic].~. Worthing, U. [sic]S.B. Walker, ~The Pesticide Manual", 7th Edition (1983), British Crop Protection Council.
The active compounds according to the invention, in particular those of the examples mentioned, can in addition be present in their commercial formulations and 3 3 ~
in the application forms prepared from these formulations mixed with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fun gicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin cornpounds, substances produced by microorganisms and the like. Preferred mixture components are:
1. from the phosphoric acid ester group azinphos-2 ethyl, azinphos-2 methyl, 1-(4-chloro-phenyl)-4-(O-ethyl, S-propyl)phosphoryl-oxypyrazole (TIA-230), chlorpyrifos, coumaphos, demeton, demeton-S-methyl, diazinon, dichlorvo~, dimethoate, ethoprophos, etrimfos, fenitrothion, fenthion, heptenophos, parathion, parathion-methyl, phosalone, pirimiphos-ethyl, pirimiphos-methyl, profenof GS, prothiofos, sulprofos, triazophos or trichlorophon.
2. from the carbamate group aldicarb, bendiocarb, BPMC (2-(1-methylpropyl)-phenylmethyl carbamate), butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, primicarb[sic], promecarb, propoxur or thiodicarb.
3. from the carboxylic acid ester group . 25 allethrin, alphamethrin, bioallethrin, : bioresmethrin, cycloprothrin, cyfluthrin, . cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl 2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)-cyclopropanecarboxy-late (FMC 54800), fenpropathrin, fenfluthrin, fen-valerate, flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin or tralomethrin.
4. from the formamidine group amitraz or chlordimeform 2 ~ 3 ~
5. from the tin compound group azocyclotin, cyhexatin and fenbutatin oxide 6. Miscellaneous abamektin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofecin, camphechlor, cartap, chlorobenzialate [sic], chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlofentezine, 2-naphthylmethyl cyclopropanecar-boxylate (Ro 12-0470), cyromacin, DDT, dicofol, N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl-amino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,2-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, endo-sulfan, fenoxycarb, fenthiocarb [sic], flubenzimine, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217 300),ivermectin,2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydro-thiaz~le(SD 35651),2-nitromethylene-1,3-thiazinan-3-yl-carbamaldehyde [sic] (WL 108 477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, triflumaron, core polyhedrosis and granulosis viruses.
The active compound content of the application forms prepared from the cornmercial formulations can vary within wide ranges, and the active compound concentration of the application forms can be from 0.0001 up to 100% by weight of active compound, preferably between 0.001 and 1% by weight. Application is carried out in one of the custom-ary ways 6uited to the application forms.
The following examples serve to illustrate the invention.
A. Formulation example~
a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as the inert substance and comminuting the 2~g33~
mixture in a hammer mill.
b) A wettable powder which is e~sily dispersible in water is obtained by mixing 25 part by weight of active compound, 64 parts by weight of kaolin-containing quartz as the inert sub~tance, 10 parts by weight of potas~ium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as the wetting agent and dispersant and grinding the mixture in a pinned disk mill.
c) A dispersion concentrate which is easily dispersible in water is obtained by mixing 40 parts by weight of active compound with 7 part~ by weight of a sul-fosuccinic acid half-ester, 2 parts by weiyht of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture in a friction ball mill to a fineness o less than 5 microns.
d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as the solvent and 10 parts by weight of oxyethylated nonylphenol (10 E0) as the - emulsifier.
e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granulate support material such as attapulgite, pumice ; 25 granules and/or quartz sand. Expediently, a ~uspen-sion of the wettable powder from Example b) having a solid~ content of 30% is used and this is sprayed onto the surface of attapulgite granules, dried and mixed intimately. The weight content of the wettable powder here i8 about 5% and that of the inert support material is about 95% of the finished granules.
2~33~
B. Chemical exa~ples 2-(6-Benzylpyridin-2-yl)-4-propylpyrimidine (Example No.: 1.2) 0.2 g of 5% palladium/carbon is added to a solution of 3.24 g (0.01 mol) of 2-(6-benzylpyridin-2-yl)-6-chloro-4-propylpyrimidine in 50 ml of ethanol. ~his mixture is brought into contact with hydrogen under a pressure of 3 bar and at a temperature of 60C with vigorous stirring for 2 h. The catalyst is then filtered off and the filtrate is concentrated in vacuo. The residue is taken up in water, saturated with sodium bicarbonate and extracted with CH2Cl2. The organic phase is dried over Na2S04 and concentrated. 2.85 g (98.6%) of a yellowish oil are obtained.
2-(6-benzylpyridin-2-yl)-4-methoxy-6-phenylpyrimidine (Example No.: 1.15) A sodium methylate solution is prepared by dissolving 0.184 g (0.008 mol) of sodium in 40 ml of abs. methanol.
1.79 g (0.005 mol) of 2-(6-benzylpyridin-2-yl)-4~chloro-6-phenylpyrimidine is added to this solution and the mixture is boiled under reflux for 3 h. It is then concentrated, water is added to the residue and the mixture is extracted with methylene chloride. The organic phase i5 dried using Na2S04 and concentrated. After crystallization from diisopropyl ether, 1.49 g (84.3%) of a colorless solid are obtained.
Melting point: 128 - 129C
2-(5-benzylpyridin-2-yl)-4,6-dimethyl-1,3,5-triazine (Example No. 2.L) 2.47 g (0,01 mol) of 6-benzyl-2-picolinamidine hydrochlo-ride are stirred together with 3048 g (0.04 mol) of ethyl acekimidate at 60c for 2 h. The reacticn mixture is then taken up in water and extracted with CHCl3. The organic 20~833~
~ 18 -phase is washed with water, dried over Na2SO4 and con centrated. The residue is subjected to column chromatog-- raphy (eluent: methylene chloride). 1.62 g (58.7%) of a colorless oil are obtained.
The compounds of Table A can be prepared analogously to these examples.
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- 27 - 2~;8338 .~
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Z r 2~8338 - ~8 -C. Biological Examples Example 1 Rice plants of the "Ballila" type about 5 weeks old were treated with the concentration of the claimed compounds indicated below after prespraying with 0.05~ strength gelatine solution. After the spray coating had dried on, the plants were uniformly inoculated with a spore suspen-sion of Piricularia oryzae and placed for 48 h in a climatic chamber, which was kept dark, having a tempera-ture of 25C and 100% relative atmospheric humidity. The rice plants were then cultivated further in a greenhouse having a temperature of 25C and 80~ relative atmospheric humidity. Evaluation of attack was carried out after 5 days. The degree of attack was expressed in % of attacked leaf surface in comparison to untreated infected controlplants. The results are collated in Table lo T~ble 1 Compound Leaf surface attacked with Piricularia according oryzae in % at mg of active compound/
to Bxample liter of spray liquor . _ 1.3 0 1.2 1.5 0 2.1 0 1.43 0 1.11 0 1.44 0 1.10 0 1.46 o . _ _ untreated infected plants 100 Exa~ple 2 Barley plants were heavily inoculated in the 2-leaf stage with barley mildew conidia (Erysiphe graminis hordei) and cultivated further in a greenhouse at 20C and a relative atmospheric humidity of about 50%. 1 day after inocula-tion, the plants were we~ted uniformly with the compounds listed in Table 2 at the active compound concentration indicated. After an incubation time of 7-9 days, the plants were examined for attack by barley mildew. The degree of attack is expressed in ~ of attacked leaf surface, relative to untreated infected control plants (=
100% attack). The result is summarized in Table 2.
Table 2 Compound Leaf surface attacked with barley according mildew in % at mg of active compound/
to Example liter of spray liquor .. . ....
1.2 0 1.43 0 1.10 0 1.~6 0 .: -untreated infected plants 100 Example 3 Wheat of the "Jubilar" type was treated in the 2-leaf stage with aqueous suspensions of the claimed compounds until dripping wet. After the spray coating had dried on, the plants were inoculated with an aqueous spore sus-pension of Puccinia recondita. The plants were placed dripping wet in a climatic chamber at 20C and about 100%
2~833~
relative atmospheric humidity for about 16 hours. The infected plants were then cultivated further in a green~
house at a temperature of 22-25C and 50-70% relative atmospheric humidity.
After an incubation time of about 2 weeks, the fungi sporulates onto the entire leaf surface of the untreated control plants such that an evaluation of attack of the test plants can be carried out. The degree of attack was expressed in % of attacked leaf surface in comparison to untreated infected control plants and iY reproduced in Table 3.
Table 3 Compound Leaf surface attacked with Puccinia re-according condita in % at mg of active compound/
to Example liter of spray liquor .
1.3 0 1.2 0 untreated infected plants 100 ~ample 4 Wheat plants of the "Jubilar" type were treated in the 2-leaf stage with aqueous suspensions o~ the preparations given in Table 4 until dripping wet.
After the spray coating had dried on, the plants were inoculated with an aqueous pyknospore suspension of Leptosphaeria nodorum and incubated at 100% relative atmospheric humidity in a climatic chamber for several hours. Until expression of symptoms, the plants were further cultivated in a greenhouse at about 9Q% relative atmospheric humidity.
- 31 - 2~83~
The degree of action is expressed as a percentage of the untreated infected control and is reproduced in Table 4.
Table 4 Compound Leaf surface attacked with Leptosphaeria according nodorum in % at mg of actlve compound~
to Example liter of spray liquor 1.43 0 1.11 0 1.44 0 1.46 o 1.14 0 1.5 0 1.4 0 1.3 0 1.2 0 untreated infected plants 103 ~xample 5 Broad beans of the "Herz Freya" or "Frank's Ackerperle"
type about 14 days old were treated with aqueous suspensions of the claimed compounds until dropping wet.
After the spray coating had dried on, the plants were inoculated with a spore suspension (1.5 million spores/ml) of Botrytis cinerea. The plants were cul-tivated further in a climatic chamber at 20-22C and about 99% relative atmospheric humidity. The infection of the plants is manifested by the formation of black spots on the leaves ancl stalks. Evaluation of the tests was carried out 1 week after inoculation.
The degree of action of the test substances was assessed 3 ~ ~
as a percentage of the untreated infected control and is reproduced in Ta~le 5.
Table 5 Compound Leaf surface attacked with ~otrytis according cinerea in % at mg of active compound/
to Example liter of spray liquor 2.1 0 untreated infected plants 100
The active compound content of the application forms prepared from the cornmercial formulations can vary within wide ranges, and the active compound concentration of the application forms can be from 0.0001 up to 100% by weight of active compound, preferably between 0.001 and 1% by weight. Application is carried out in one of the custom-ary ways 6uited to the application forms.
The following examples serve to illustrate the invention.
A. Formulation example~
a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as the inert substance and comminuting the 2~g33~
mixture in a hammer mill.
b) A wettable powder which is e~sily dispersible in water is obtained by mixing 25 part by weight of active compound, 64 parts by weight of kaolin-containing quartz as the inert sub~tance, 10 parts by weight of potas~ium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as the wetting agent and dispersant and grinding the mixture in a pinned disk mill.
c) A dispersion concentrate which is easily dispersible in water is obtained by mixing 40 parts by weight of active compound with 7 part~ by weight of a sul-fosuccinic acid half-ester, 2 parts by weiyht of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture in a friction ball mill to a fineness o less than 5 microns.
d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as the solvent and 10 parts by weight of oxyethylated nonylphenol (10 E0) as the - emulsifier.
e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granulate support material such as attapulgite, pumice ; 25 granules and/or quartz sand. Expediently, a ~uspen-sion of the wettable powder from Example b) having a solid~ content of 30% is used and this is sprayed onto the surface of attapulgite granules, dried and mixed intimately. The weight content of the wettable powder here i8 about 5% and that of the inert support material is about 95% of the finished granules.
2~33~
B. Chemical exa~ples 2-(6-Benzylpyridin-2-yl)-4-propylpyrimidine (Example No.: 1.2) 0.2 g of 5% palladium/carbon is added to a solution of 3.24 g (0.01 mol) of 2-(6-benzylpyridin-2-yl)-6-chloro-4-propylpyrimidine in 50 ml of ethanol. ~his mixture is brought into contact with hydrogen under a pressure of 3 bar and at a temperature of 60C with vigorous stirring for 2 h. The catalyst is then filtered off and the filtrate is concentrated in vacuo. The residue is taken up in water, saturated with sodium bicarbonate and extracted with CH2Cl2. The organic phase is dried over Na2S04 and concentrated. 2.85 g (98.6%) of a yellowish oil are obtained.
2-(6-benzylpyridin-2-yl)-4-methoxy-6-phenylpyrimidine (Example No.: 1.15) A sodium methylate solution is prepared by dissolving 0.184 g (0.008 mol) of sodium in 40 ml of abs. methanol.
1.79 g (0.005 mol) of 2-(6-benzylpyridin-2-yl)-4~chloro-6-phenylpyrimidine is added to this solution and the mixture is boiled under reflux for 3 h. It is then concentrated, water is added to the residue and the mixture is extracted with methylene chloride. The organic phase i5 dried using Na2S04 and concentrated. After crystallization from diisopropyl ether, 1.49 g (84.3%) of a colorless solid are obtained.
Melting point: 128 - 129C
2-(5-benzylpyridin-2-yl)-4,6-dimethyl-1,3,5-triazine (Example No. 2.L) 2.47 g (0,01 mol) of 6-benzyl-2-picolinamidine hydrochlo-ride are stirred together with 3048 g (0.04 mol) of ethyl acekimidate at 60c for 2 h. The reacticn mixture is then taken up in water and extracted with CHCl3. The organic 20~833~
~ 18 -phase is washed with water, dried over Na2SO4 and con centrated. The residue is subjected to column chromatog-- raphy (eluent: methylene chloride). 1.62 g (58.7%) of a colorless oil are obtained.
The compounds of Table A can be prepared analogously to these examples.
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- 27 - 2~;8338 .~
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Z r 2~8338 - ~8 -C. Biological Examples Example 1 Rice plants of the "Ballila" type about 5 weeks old were treated with the concentration of the claimed compounds indicated below after prespraying with 0.05~ strength gelatine solution. After the spray coating had dried on, the plants were uniformly inoculated with a spore suspen-sion of Piricularia oryzae and placed for 48 h in a climatic chamber, which was kept dark, having a tempera-ture of 25C and 100% relative atmospheric humidity. The rice plants were then cultivated further in a greenhouse having a temperature of 25C and 80~ relative atmospheric humidity. Evaluation of attack was carried out after 5 days. The degree of attack was expressed in % of attacked leaf surface in comparison to untreated infected controlplants. The results are collated in Table lo T~ble 1 Compound Leaf surface attacked with Piricularia according oryzae in % at mg of active compound/
to Bxample liter of spray liquor . _ 1.3 0 1.2 1.5 0 2.1 0 1.43 0 1.11 0 1.44 0 1.10 0 1.46 o . _ _ untreated infected plants 100 Exa~ple 2 Barley plants were heavily inoculated in the 2-leaf stage with barley mildew conidia (Erysiphe graminis hordei) and cultivated further in a greenhouse at 20C and a relative atmospheric humidity of about 50%. 1 day after inocula-tion, the plants were we~ted uniformly with the compounds listed in Table 2 at the active compound concentration indicated. After an incubation time of 7-9 days, the plants were examined for attack by barley mildew. The degree of attack is expressed in ~ of attacked leaf surface, relative to untreated infected control plants (=
100% attack). The result is summarized in Table 2.
Table 2 Compound Leaf surface attacked with barley according mildew in % at mg of active compound/
to Example liter of spray liquor .. . ....
1.2 0 1.43 0 1.10 0 1.~6 0 .: -untreated infected plants 100 Example 3 Wheat of the "Jubilar" type was treated in the 2-leaf stage with aqueous suspensions of the claimed compounds until dripping wet. After the spray coating had dried on, the plants were inoculated with an aqueous spore sus-pension of Puccinia recondita. The plants were placed dripping wet in a climatic chamber at 20C and about 100%
2~833~
relative atmospheric humidity for about 16 hours. The infected plants were then cultivated further in a green~
house at a temperature of 22-25C and 50-70% relative atmospheric humidity.
After an incubation time of about 2 weeks, the fungi sporulates onto the entire leaf surface of the untreated control plants such that an evaluation of attack of the test plants can be carried out. The degree of attack was expressed in % of attacked leaf surface in comparison to untreated infected control plants and iY reproduced in Table 3.
Table 3 Compound Leaf surface attacked with Puccinia re-according condita in % at mg of active compound/
to Example liter of spray liquor .
1.3 0 1.2 0 untreated infected plants 100 ~ample 4 Wheat plants of the "Jubilar" type were treated in the 2-leaf stage with aqueous suspensions o~ the preparations given in Table 4 until dripping wet.
After the spray coating had dried on, the plants were inoculated with an aqueous pyknospore suspension of Leptosphaeria nodorum and incubated at 100% relative atmospheric humidity in a climatic chamber for several hours. Until expression of symptoms, the plants were further cultivated in a greenhouse at about 9Q% relative atmospheric humidity.
- 31 - 2~83~
The degree of action is expressed as a percentage of the untreated infected control and is reproduced in Table 4.
Table 4 Compound Leaf surface attacked with Leptosphaeria according nodorum in % at mg of actlve compound~
to Example liter of spray liquor 1.43 0 1.11 0 1.44 0 1.46 o 1.14 0 1.5 0 1.4 0 1.3 0 1.2 0 untreated infected plants 103 ~xample 5 Broad beans of the "Herz Freya" or "Frank's Ackerperle"
type about 14 days old were treated with aqueous suspensions of the claimed compounds until dropping wet.
After the spray coating had dried on, the plants were inoculated with a spore suspension (1.5 million spores/ml) of Botrytis cinerea. The plants were cul-tivated further in a climatic chamber at 20-22C and about 99% relative atmospheric humidity. The infection of the plants is manifested by the formation of black spots on the leaves ancl stalks. Evaluation of the tests was carried out 1 week after inoculation.
The degree of action of the test substances was assessed 3 ~ ~
as a percentage of the untreated infected control and is reproduced in Ta~le 5.
Table 5 Compound Leaf surface attacked with ~otrytis according cinerea in % at mg of active compound/
to Example liter of spray liquor 2.1 0 untreated infected plants 100
Claims (6)
1. A compound of the formula I
(I), in which R1, R2, R3 and R4 are independently of one another, hydrogen, halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkoxy or (C1-C4) haloalkyl, R5, R6 and R7 are independently of one another hydrogen, (C1-C6)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to trisub-stituted by halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4) haloalkyl, or (C1-C4)haloalkoxy, R8 and R9 are independently of one another hydrogen, (C1-C6)alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl-(C1-C4)alkyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the cycloalkyl moiety by (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkylthio-(C1-C4)alkyl, halogen, (C2-C6)al-kenyl, (C2-C6)alkynyl, phenyl, phenoxy, phenoxy-(C1-C4)alkyl, phenylmercapto-(C1-C4)alkyl, phenyl-mercapto, phenyl-(C1-C4)alkoxy or phenyl-(C1-C4)alkylthio, it being possible for the seven last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-C4)halo-alkoxy, or (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C1-C4)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy or (C1-C4)alkylthio-(C1-C4)alkylthio, R10 is hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C2-C6)-alkenyloxy, (C2-C6)alkynyloxy, (C1-C4)alkylthio, halogen, phenyl, it being possible for the phenyl radical to be monosubstituted to trisubstituted by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alk-oxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-4)haloalkoxy, or R8 and R10 together form a polymethylene chain of the formula -(CH2)m- where m = 3 - 4, R11 and R12 are independently of one another hydrogen or (C1-C4)alkyl, Y is N or -CR10 and n is 1-3, and their acid addition salts.
(I), in which R1, R2, R3 and R4 are independently of one another, hydrogen, halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkoxy or (C1-C4) haloalkyl, R5, R6 and R7 are independently of one another hydrogen, (C1-C6)alkyl or phenyl, it being possible for the phenyl radical to be monosubstituted to trisub-stituted by halogen, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4) haloalkyl, or (C1-C4)haloalkoxy, R8 and R9 are independently of one another hydrogen, (C1-C6)alkyl, (C3-C7) cycloalkyl, (C3-C7) cycloalkyl-(C1-C4)alkyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the cycloalkyl moiety by (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkylthio-(C1-C4)alkyl, halogen, (C2-C6)al-kenyl, (C2-C6)alkynyl, phenyl, phenoxy, phenoxy-(C1-C4)alkyl, phenylmercapto-(C1-C4)alkyl, phenyl-mercapto, phenyl-(C1-C4)alkoxy or phenyl-(C1-C4)alkylthio, it being possible for the seven last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-C4)halo-alkoxy, or (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C1-C4)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy or (C1-C4)alkylthio-(C1-C4)alkylthio, R10 is hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C2-C6)-alkenyloxy, (C2-C6)alkynyloxy, (C1-C4)alkylthio, halogen, phenyl, it being possible for the phenyl radical to be monosubstituted to trisubstituted by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alk-oxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-4)haloalkoxy, or R8 and R10 together form a polymethylene chain of the formula -(CH2)m- where m = 3 - 4, R11 and R12 are independently of one another hydrogen or (C1-C4)alkyl, Y is N or -CR10 and n is 1-3, and their acid addition salts.
2. A compound of the formula I of claim 1, in which R1, R2, R3 and R4 are independently of one another hydro-gen, halogen, (C1-C2)haloalkyl or (C1-C3)alkyl, R5 and R6 are independently of one another hydrogen, (C1-C3)alkyl or phenyl, it being possible for the phenyl rddical to be monosubstituted to trisub-stituted by haloqen or (C1-C4)alkyl, R7 is hydrogen, R8 and R9 are independently of one another hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkyl-(C1-C3)alkyl, halogen, phenyl which can be mono-substituted to trisubstituted by halogen, (C1-C4)alkyl or (C1-C4) alkoxy, or (C2-C4)alkenyl-oxy, (C2-C4)alkynyloxy, (C1-C4)haloalkoxy or (C1-C4)alkoxy-(C1-C4)alkoxy, R10 is hydrogen, (C1-C4)alkyl, halogen, phenyl, it being possible for the phenyl radical to be monosubstituted to trisubstituted by halogen or (C1-C3)alkyl, or (C1-C3)alkoxy or R8 and R10 together form a polymethylene chain of the formula -(CH2)m- where m = 3 - 4, R11 and R12 are hydrogen, Y is N or -CR10 and n = 1, and their acid addition salts.
3. A process for the preparation of compounds of the formula I as claimed in claim 1 or 2, which comprises a) for compounds I where R9 = H, Y = -CR10 and the remaining substituents have the meanings of the formula I, reductively dehalogenating an appropriate halopyrimidine I in which R9 = halogen, or b) for compounds I in which R9 is (C1-C4)alkoxy, (C1-C4)alkylthio, phenoxy, phenylmercapto, phenyl-(C1-C4)alkoxy or phenyl-(C1-C4)alkylthio, it being possible for the 4 last-mentioned radicals in the phenyl moiety to be monosubstituted to trisubstitu-ted by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-C4)haloalkoxy, or (C2-C4) alkenyloxy, (C2-C4)alkynyl-oxy, (C1-C4)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy or (C1-C4)alkylthio-(C1-C4)alkylthio and Y is -CR10, reacting an appropriate halopyrimidine I in which R9 = halogen with a compound of the formula II
R9M (II), where R9 has the abovementioned meaning and M is an alkali metal, or c) for compounds of the formula I in which R9 is (C1-C6)alkyl, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl-(C1-C4)alkyl,(C1-C4)alkoxy-(C1-C4)alkyl,(C1-C4)alkyl-thio-(C1-C4)alkyl or phenyl, it being possible for the last-mentioned radical to be monosubstituted to trisubstituted by (C1-C4)alkyl or (C1-C4)alkoxy, and Y is -CR10 reacting an appropriate halopyrimidine I
where R9 = halogen with a Grignard compound III
R9 MgX (III), where R9 has the abovementioned meaning and X is halogen, in the presence of nickel-phosphine com-plexes, or d) for compounds o the formula I in which R3 = R9 and is (C1-C4)alkyl, phenyl-(C1-C4)alkyl or phenyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-C4)haloalkoxy, and Y is N, reacting an amidine derivative of the formula IV
(IV), in which R1-R7, R11-R12 and n have the meaning indicated in formula I and X is halogen, with an imidate derivative of the formula VI
(VI), where R9 has the abovementioned meaning and R13 is (C1-C3)alkyl.
R9M (II), where R9 has the abovementioned meaning and M is an alkali metal, or c) for compounds of the formula I in which R9 is (C1-C6)alkyl, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl-(C1-C4)alkyl,(C1-C4)alkoxy-(C1-C4)alkyl,(C1-C4)alkyl-thio-(C1-C4)alkyl or phenyl, it being possible for the last-mentioned radical to be monosubstituted to trisubstituted by (C1-C4)alkyl or (C1-C4)alkoxy, and Y is -CR10 reacting an appropriate halopyrimidine I
where R9 = halogen with a Grignard compound III
R9 MgX (III), where R9 has the abovementioned meaning and X is halogen, in the presence of nickel-phosphine com-plexes, or d) for compounds o the formula I in which R3 = R9 and is (C1-C4)alkyl, phenyl-(C1-C4)alkyl or phenyl, it being possible for the two last-mentioned radicals to be monosubstituted to trisubstituted in the phenyl moiety by halogen, nitro, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkyl or (C1-C4)haloalkoxy, and Y is N, reacting an amidine derivative of the formula IV
(IV), in which R1-R7, R11-R12 and n have the meaning indicated in formula I and X is halogen, with an imidate derivative of the formula VI
(VI), where R9 has the abovementioned meaning and R13 is (C1-C3)alkyl.
4. A fungicidal agent which contains an effective amount of a compound of the formula I as claimed in claim 1 or 2.
5. The use of compounds of the formula I as claimed in claim 1 or 2 for controlling harmful fungi.
6. A method for controlling harmful fungi which com-prises applying an effective amount of a compound of the formula I as claimed in claim 1 or 2 to the plants, surfaces or substrates attacked by them.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3937285.5 | 1989-11-09 | ||
DE3937285A DE3937285A1 (en) | 1989-11-09 | 1989-11-09 | PYRIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THE AGENTS CONTAINING THEY AND THEIR USE AS FUNGICIDES |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2068338A1 true CA2068338A1 (en) | 1991-05-10 |
Family
ID=6393174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002068338A Abandoned CA2068338A1 (en) | 1989-11-09 | 1990-11-07 | Pyridine derivatives, process for making them, agents containing them and their use as fungicides |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP0500755B1 (en) |
JP (1) | JPH05501558A (en) |
KR (1) | KR927003570A (en) |
CN (1) | CN1051558A (en) |
AU (1) | AU6886891A (en) |
BR (1) | BR9007831A (en) |
CA (1) | CA2068338A1 (en) |
DE (2) | DE3937285A1 (en) |
HU (1) | HUT62286A (en) |
IL (1) | IL96270A0 (en) |
MX (1) | MX23261A (en) |
PT (1) | PT95832A (en) |
WO (1) | WO1991007399A1 (en) |
YU (1) | YU212890A (en) |
ZA (1) | ZA908959B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9012017D0 (en) * | 1990-05-30 | 1990-07-18 | Ici Plc | Fungicidal compounds |
GB9024873D0 (en) * | 1990-11-15 | 1991-01-02 | Ici Plc | Fungicidal compounds |
DE4128789A1 (en) * | 1991-08-30 | 1993-03-04 | Bayer Ag | SUBSTITUTED PYRIDYLTRIAZINE, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AND NEW INTERMEDIATE PRODUCTS |
EA007719B1 (en) | 2001-03-15 | 2006-12-29 | Басф Акциенгезельшафт | 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi |
CA2764818A1 (en) * | 2009-06-08 | 2010-12-16 | California Capital Equity, Llc | Triazine derivatives and their therapeutical applications |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3675197D1 (en) * | 1985-12-03 | 1990-11-29 | Sumitomo Chemical Co | PYRIDINYLPYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THESE PLANT DISEASES PROTECTIVE CONTAINING THE ACTIVE SUBSTANCE. |
PH23565A (en) * | 1986-09-05 | 1989-08-25 | Sumitomo Chemical Co | Novel pyrimidinylpyrimidine derivatives and a plant disease protectant containing them as the active ingredient |
-
1989
- 1989-11-09 DE DE3937285A patent/DE3937285A1/en not_active Withdrawn
-
1990
- 1990-10-05 ZA ZA908959A patent/ZA908959B/en unknown
- 1990-11-07 DE DE59010331T patent/DE59010331D1/en not_active Expired - Fee Related
- 1990-11-07 AU AU68868/91A patent/AU6886891A/en not_active Abandoned
- 1990-11-07 KR KR1019920701087A patent/KR927003570A/en not_active Withdrawn
- 1990-11-07 WO PCT/EP1990/001857 patent/WO1991007399A1/en active IP Right Grant
- 1990-11-07 BR BR909007831A patent/BR9007831A/en not_active Application Discontinuation
- 1990-11-07 HU HU9201542A patent/HUT62286A/en unknown
- 1990-11-07 EP EP90917650A patent/EP0500755B1/en not_active Expired - Lifetime
- 1990-11-07 IL IL96270A patent/IL96270A0/en unknown
- 1990-11-07 JP JP3500089A patent/JPH05501558A/en active Pending
- 1990-11-07 CA CA002068338A patent/CA2068338A1/en not_active Abandoned
- 1990-11-08 CN CN90108966A patent/CN1051558A/en active Pending
- 1990-11-08 PT PT95832A patent/PT95832A/en not_active Application Discontinuation
- 1990-11-09 YU YU212890A patent/YU212890A/en unknown
- 1990-11-09 MX MX2326190A patent/MX23261A/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE59010331D1 (en) | 1996-06-20 |
DE3937285A1 (en) | 1991-05-16 |
IL96270A0 (en) | 1991-08-16 |
HUT62286A (en) | 1993-04-28 |
ZA908959B (en) | 1991-08-28 |
MX23261A (en) | 1993-11-01 |
EP0500755B1 (en) | 1996-05-15 |
HU9201542D0 (en) | 1992-09-28 |
JPH05501558A (en) | 1993-03-25 |
EP0500755A1 (en) | 1992-09-02 |
WO1991007399A1 (en) | 1991-05-30 |
YU212890A (en) | 1992-09-07 |
BR9007831A (en) | 1992-09-22 |
KR927003570A (en) | 1992-12-18 |
CN1051558A (en) | 1991-05-22 |
PT95832A (en) | 1991-09-13 |
AU6886891A (en) | 1991-06-13 |
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