JPS6323870A - 2-substituted sulfonylpyrimidine derivative - Google Patents
2-substituted sulfonylpyrimidine derivativeInfo
- Publication number
- JPS6323870A JPS6323870A JP61167066A JP16706686A JPS6323870A JP S6323870 A JPS6323870 A JP S6323870A JP 61167066 A JP61167066 A JP 61167066A JP 16706686 A JP16706686 A JP 16706686A JP S6323870 A JPS6323870 A JP S6323870A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- compound
- substituted
- alkoxy
- 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.)
- Granted
Links
- -1 2-substituted sulfonylpyrimidine Chemical class 0.000 title claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000417 fungicide Substances 0.000 abstract description 5
- 240000008067 Cucumis sativus Species 0.000 abstract description 4
- 230000000855 fungicidal effect Effects 0.000 abstract description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 2
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 2
- IWEPSGGZINUNSM-UHFFFAOYSA-N 2-sulfonyl-1h-pyrimidine Chemical class O=S(=O)=C1N=CC=CN1 IWEPSGGZINUNSM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-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
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- PBDUGUOJJABWLO-UHFFFAOYSA-N 4-(difluoromethoxy)-6-methoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC(F)F)=NC(S(C)(=O)=O)=N1 PBDUGUOJJABWLO-UHFFFAOYSA-N 0.000 description 1
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 244000000005 bacterial plant pathogen Species 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 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 1
- 230000003902 lesion Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YNPFMWCWRVTGKJ-UHFFFAOYSA-N mianserin hydrochloride Chemical compound [H+].[Cl-].C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 YNPFMWCWRVTGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、農園芸用殺菌剤および除草剤の中間体として
有用であり、それ自身も殺菌列として有用な２−置換ス
ルホニルビ＋１ ミジン誘導体（以下本発明化合物と称
する）Ｋ関する。Detailed Description of the Invention (Industrial Field of Application) The present invention provides 2-substituted sulfonyl bi+1 midine derivatives ( (hereinafter referred to as the compound of the present invention).
１（従来の技Ｖｇ）
特開昭５９−５９６６９号明細書には、不発明化合物の
前駆体である２−アルキルチオピリミジン誘導体の１つ
の例として、２−メチルチオ−４，６−シメトキシビリ
ミジンが記載されており、その５位をホルミル化する原
料として使用している。しかしながらこれを酸化して得
られる本発明化合物については記載されていない。1 (Prior art Vg) JP-A-59-59669 describes 2-methylthio-4,6-simethoxypyrimidine as an example of a 2-alkylthiopyrimidine derivative which is a precursor of an uninvented compound. is described, and its 5th position is used as a raw material for formylation. However, the compound of the present invention obtained by oxidizing this is not described.
キシピリミジンが記載されており、米国特許第４５４２
２１６号に（工、２−メチルスルホニル−４−ジフルオ
ロメトキシ−６−メトキシピリミジンが記載されている
が、いずれも生理活性に関しては言及されておらす、本
発明化合物についても全（記載されていない０
本発明化合物は文献未記載の新規化合物であり、しかも
殺菌剤としての有用性をも併せもつものである。Xypyrimidine has been described, US Pat. No. 4,542
In No. 216, 2-methylsulfonyl-4-difluoromethoxy-6-methoxypyrimidine is described, but none of them mention physiological activity. 0 The compound of the present invention is a novel compound that has not been described in any literature, and also has usefulness as a fungicide.
（発明が解決しよ５とする問題点及び 問題点を解決するための手段） 本発明化合物は・中間体として有用である。(Problems to be solved by the invention and (Means to solve the problem) The compounds of the present invention are useful as intermediates.
最終物質としての２−（を換）フェノキシ−４゜６−ジ
置換ピリミジン誘導体及び２−（置換）アニリノ−４，
６一ジ誼換ピリミジン誘導体は、それぞれ水田用、畑作
用除草剤及び農園芸用殺菌剤として優れた性質を持つも
のである０これらを製造する方法は各種あるが、本発明
化合物を中間体として使用した場合には、収率良く純度
も高い最終生成物が得られるという利点を有する。2-(substituted)phenoxy-4゜6-disubstituted pyrimidine derivatives and 2-(substituted)anilino-4,
The diconverted pyrimidine derivatives have excellent properties as herbicides for paddy fields, field herbicides, and fungicides for agriculture and horticulture, respectively.There are various methods for producing these, but using the compound of the present invention as an intermediate. When used, it has the advantage that a final product with good yield and high purity can be obtained.
本発明化合物は、さらに殺菌剤としての有用性も兼ね備
えている。すなわち、種々の植物病原菌、特にキーウリ
灰色カビ病菌、ベト病菌、トマト疫病菌及びリンビ斑落
病菌に対して優れた殺菌活性を有するとともに、エンテ
ロノ々クター・アエログネス（Ｅｎｔｅｒｏｂａｃｔｅ
ｒ ａｅｒｏｇｅｎｅｓ）％イー・コーリ（：ｌ５ｃｈ
ｅｒｉｃｈｉａ ｃｏｌｉ）、ノ々チルス・ズブチルス
（Ｂａｏｉｌｌｕｓ ５ｕｂｔｉｌｉｓ）、ノ々チルス
・セレウス（Ｂａｃｉｌｌｕｓ ｃｅｒｅｕｓ）、シュ
ウトモナス・アエルギノサ（ｐｓｅｕａｏｍｏｎａｓ
ａｅｒｕｇｉｎｏｓａ）、スタフィロコッカス・アウレ
ウス（Ｓｔａｐｈｙｌｏｃ ｏｃｃｕｓａｕｒｅｕａ）
等の細菌類及びアスペルギルス◆ニガー （Ａｓｐｅｒ
ｇｉｌｌｕａ ｎｉｇθｒ）、ゲオトリカム・カンジダ
ム（Ｇｅｏｔｒｉｃｈｕｍ ｃａｎｄｌｕｍ）、アウレ
、Ｓシジウム・プルラン、ｘ、 （Ａｕｒｅｏｂａｓｔ
ａｌｕｍ ｐｕｌｌｕｌａｎａ）、ペニシリウム・ステ
ッキ（Ｐｅｎｉｃｉｌｌｉｕｍ ５ｔｅｃｋｉｉ）、ト
リ：コデルマ（Ｔｒｉａｈｏｄｅｒｍａ ＳＰ） 等
の糸状菌に（構 成）
本発明の２−置換スルホニルピリミジン誘導体は、一般
式
（式中、Ａはアルキル基またはベンジル基を示し、Ｒ１
はアルキル基、アルコキシ基、ハロゲン原子、プロピニ
ル基またはトリメチルシリルエチニル基ヲ示し、Ｒ１ハ
アルキル基・アルコキシ基、プロピニル基、ハロゲン置
換プロピニルオキシ基またはトリメチルシリルエチニル
基を示す。但し・Ａがメチル基のとき・Ｒ１はへ以上の
アルキル基、アルコキシ基、ヨウ素原子、）。The compounds of the present invention also have utility as fungicides. In other words, it has excellent fungicidal activity against various plant pathogenic bacteria, especially Botrytis botrytis, Downy mildew, Tomato Phytophthora, and Limbi bacterium.
r aerogenes)% E. Kohli (:l5ch
erichia coli), Baoillus 5ubtilis, Bacillus cereus, pseudomonas aeruginosa
aeruginosa), Staphylococcus aureus (Staphylococcus aureus)
Bacteria such as Aspergillus niger
gillua nigθr), Geotrichum candlum, Aure, S. pullulan, x, (Aureobast
The 2-substituted sulfonylpyrimidine derivative of the present invention can be applied to filamentous fungi such as Alum pullulana, Penicillium 5teckii, and Triahoderma SP. Represents a benzyl group, R1
represents an alkyl group, an alkoxy group, a halogen atom, a propynyl group or a trimethylsilylethynyl group, and represents an R1 haalkyl group/alkoxy group, propynyl group, halogen-substituted propynyloxy group or trimethylsilylethynyl group. However, when A is a methyl group, R1 is an alkyl group, an alkoxy group, or an iodine atom.
素原子、臭素原子、プロピニル基またはトリメチルシリ
ルエチニル基を示し、八）Ｘ Ｃ１以上のアルキル基、
アルコキシ基、フロビニル基、ハロゲン置換プロピニル
オキシ基またはトリメチルシリルエチニル基を示す。）
で表わされろ０上記一般式〔！〕にて表わされる化合物
を第１表に例示する。化合物番号は以後の記載において
参照される。8) represents an atom, a bromine atom, a propynyl group or a trimethylsilylethynyl group;
It represents an alkoxy group, a flovinyl group, a halogen-substituted propynyloxy group, or a trimethylsilylethynyl group. )
Represented by 0 above general formula [! ] Table 1 shows examples of compounds represented by . Compound numbers are referenced in the following description.
富 ト 「 ［− 本発明化合物は次の反応式に従って得ることが出来る。wealth to " [- The compound of the present invention can be obtained according to the following reaction formula.
Ｃｍ］ ［ｍ〕［、ｒ〕（但し、式中
Ａ、Ｒ，及び凡は前述の意味を表わす０）上記反応にお
いて酸化剤としては、過マンガン酸カリウム、過硫酸水
素カリウム、酸化ルテニウム、酸化オスミウム、メタ過
ヨウ素醋ナトリウム、四酸化二窒素、過酷化水素、過酸
、ヒドロペルオキシド、オゾン等が使用される。Cm] [m] [, r] (However, in the formula, A, R, and 0 represent the above-mentioned meanings) In the above reaction, the oxidizing agent is potassium permanganate, potassium hydrogen persulfate, ruthenium oxide, Osmium, sodium metaperiodide, dinitrogen tetroxide, harsh hydrogen, peracid, hydroperoxide, ozone, etc. are used.
過酸化水素を用いる場合、タングステン酸ナトリウム等
のタングステン触媒も有効である。When hydrogen peroxide is used, tungsten catalysts such as sodium tungstate are also effective.
式ＣＩ）の式ＣＩ）への酸化は式（ＩＩＩ）のスルホキ
シドを経て合成されるが、使用される溶媒は酢酸、＠酸
、水、ジクロロメタン、クロロホルム、四ｍ化炭素、メ
チルアルコール、エチルアルコール、クロロベンゼン、
ジクロロベンゼン等が挙げられろ。これらの溶媒を混合
することによっても使用できる。反応温度は、０度から
１００度、特に好ましくは室温から７０度である□次に
製造例を挙げて具体的に説明する。The oxidation of formula CI) to formula CI) is synthesized via the sulfoxide of formula (III), and the solvents used are acetic acid, @acid, water, dichloromethane, chloroform, carbon tetramide, methyl alcohol, ethyl alcohol. , chlorobenzene,
Examples include dichlorobenzene. It can also be used by mixing these solvents. The reaction temperature is from 0 degrees Celsius to 100 degrees Celsius, particularly preferably from room temperature to 70 degrees Celsius.Next, a detailed explanation will be given with reference to production examples.
製造例１）２−メチルスルホニル−４，６ｙｙ’トキシ
ビリミジン（化合物１ンの契
２−メチルチオー４，６−シメトキシピリミジン１８６
．２ｐ（１モル）を酢酸２００ｄ中に入れ、タングステ
ン酸ナトリウム・２水塩１０？（０，０３モル）を入れ
た後、４０℃にて攪拌下３０％過酸化水素２２６．６ｔ
＜２モル）をゆっくり滴下した。温度は５０℃±ｌＯ℃
に保って２時間反応を行わせた。滴下終了後１時間熟成
度応を行った後、未反応の過酸化水素を亜硫酸ナトリウ
ムで処理をし結晶な濾別、水洗し、２−メチルスルホニ
ル−牛、６−シメトキシビリミジン１９３．５２（収率
８８．６％）を得た。融点１１６〜１１９℃
（ａ 造例２ ） ２−ベンジルスルホニル−４−メチ
ル−６−（１−プロピニル）ピリミ
ジン（化合物１０）の製造
２−ベンジルチオ−牛−メチル−６−（１−プロピニル
）ピリミジン５．５２をクロロホルム１０Ｑｍへ溶解し
、この溶液へ７０％メタクロル過安息査酸１６．２ｐを
加え、室温で１時間攪拌した。反応混合物を濾過、濾液
を重曹水、次いで水で洗い、芒硝で乾燥後、濃縮した。Production Example 1) 2-Methylsulfonyl-4,6yy'toxypyrimidine (2-methylthio-4,6-cymethoxypyrimidine 186 of compound 1)
．． Put 2p (1 mol) in 200d of acetic acid and add 10% of sodium tungstate dihydrate. After adding (0.03 mol), 226.6 t of 30% hydrogen peroxide was stirred at 40°C.
<2 mol) was slowly added dropwise. Temperature is 50℃±lO℃
The reaction was carried out for 2 hours while maintaining the temperature. After the completion of the dropwise addition, the ripening rate was determined for 1 hour, and unreacted hydrogen peroxide was treated with sodium sulfite, and the crystals were filtered off and washed with water to give 2-methylsulfonyl-cow, 6-cymethoxypyrimidine 193.52 (yield: 88.6%). Melting point: 116-119°C (a Preparation Example 2) Production of 2-benzylsulfonyl-4-methyl-6-(1-propynyl)pyrimidine (Compound 10) 2-benzylthio-cow-methyl-6-(1-propynyl)pyrimidine 5.52 was dissolved in 10Qm of chloroform, 16.2p of 70% methachloroperbenzoic acid was added to this solution, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was washed with aqueous sodium bicarbonate and then with water, dried over Glauber's salt, and concentrated.
残渣をエタノールで再結して、２−ベンジルスルホ＝
Ａ／ −４−メチル−６−（１−プロピニル）ピリミジ
ン５．８＃（収率９７％）を得た。The residue was reconsolidated with ethanol to give 2-benzylsulfo=
A/-4-methyl-6-(1-propynyl)pyrimidine 5.8# (yield 97%) was obtained.
融点 １３１〜１３３℃
本発明化合物は、それ自体で用いてもよいが、通常は担
体、界面活性剤、分散剤またを工補助剤等を配合して常
法により、例えば粉剤、水和剤、乳剤、微粒剤または粒
剤に製剤する。Melting point: 131-133°C The compound of the present invention may be used by itself, but it is usually mixed with a carrier, a surfactant, a dispersant, or a processing aid, etc., and prepared by a conventional method, such as a powder, a wettable powder, or a powder. Formulate into emulsion, microgranules or granules.
好適な担体としては、例えばメルク、ベントナイト、ク
レー、カオリン、珪礫土、ホワイトカーボン、バーミキ
ュライト、消石灰、珪砂、硫安、尿素等の固体担体、メ
チルナフタリン、イソプロピルアルコール、キシレン、
シクロヘキサノン等の液体担体等が挙げられろ・界面活
性剤及び分散剤としては、例えばジナフチルメタンジス
ルホン酸塩、アルコール硫酸エステル塩、アルキルスル
ホン酸塩、アルキルアリール、スルホン酢塩、リグニン
スルホン酸塩、ポリオキシエチレングリコールエーテル
、ポリオキシエチレンアルキルアリールエーテル、ポリ
オキシエチレンソルビタンモノアルキレート等が挙げら
れる。補助剤としては、例えばカルボキシメチルセルロ
ース、ポリエチレングリコール、アラビアゴム等が挙げ
られる。これらの製剤を適宜な濃度に希釈して散布する
か、又は直接施用する。Suitable carriers include, for example, solid carriers such as Merck, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea, methylnaphthalene, isopropyl alcohol, xylene,
Examples include liquid carriers such as cyclohexanone. Examples of surfactants and dispersants include dinaphthylmethane disulfonate, alcohol sulfate ester salt, alkyl sulfonate, alkylaryl, sulfone acetate salt, lignin sulfonate, Examples include polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monoalkylate, and the like. Examples of the adjuvant include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. These preparations can be diluted to an appropriate concentration and sprayed, or applied directly.
次に製剤例を挙げて具体的に説明する。下記表剤例中の
係は重量％を意味する。Next, a specific explanation will be given using formulation examples. In the following surface agent examples, the term "byte" means % by weight.
製剤例１ （粉剤）
化合物（１）２％、珪藻±５％及びクレー９３傷を均一
に混合粉砕して粉剤とする。Formulation Example 1 (Powder) 2% of compound (1), ±5% of diatoms, and 93 scratches of clay are uniformly mixed and ground to obtain a powder.
製剤例２ （水和剤）
化合−（４） ５０係、珪藻±４５％、ジナフチルメタ
ンジスルホン酸ナトリウム２％及びリグニンスルホン酸
ナトリウム３％を均一に混合粉砕して水和剤とする＠
製剤例３ （乳剤）
化合物（５１３０％、シクロヘキサノン２０チ、ポリオ
キシエチレンアルキルアリールエーテル１１％、アルキ
ルベンゼンスルホン酸カル−に溶解して乳剤とずぶ。′
製剤例４ ｃ粒剤）
化合物αＧ５％、ラウリルアルコール臓酸エステルのナ
トリウム塩２％、リグニンスルホン酸ナトリウム５％、
カルボキシメチルセルロース２％及びクレー８６％を均
一に混合粉砕する・この混合物１００重量部に水２０重
量部を側えて練合し、押出式造粒機を用いて１４〜３２
メツシユの粒状に加工したのち、乾燥して粒剤とする。Formulation Example 2 (Wettable powder) Compound-(4) Unit 50, diatom ±45%, 2% sodium dinaphthylmethane disulfonate, and 3% sodium ligninsulfonate are uniformly mixed and ground to form a wettable powder @ Formulation Example 3 (Emulsion) Compound (5130%, 20% cyclohexanone, 11% polyoxyethylene alkylaryl ether, dissolved in alkylbenzene sulfonic acid carboxyl to form an emulsion. Formulation Example 4 C granules) Compound αG 5%, lauryl alcohol 2% sodium salt of visceral acid ester, 5% sodium lignin sulfonate,
2% carboxymethyl cellulose and 86% clay are uniformly mixed and pulverized. 100 parts by weight of this mixture is kneaded with 20 parts by weight of water, and an extrusion granulator is used to make 14-32% of the mixture.
After processing into mesh granules, it is dried and made into granules.
次に本発明化合物の奏する殺菌効果を試験例を挙げて具
体的【説明する。Next, the bactericidal effect exhibited by the compound of the present invention will be specifically explained using test examples.
試験例１ （キュウリ灰色かび病防除効果）−辺９１の
角鉢に鉢当り１２粒播槙したキーウリ（品種；相撲半白
）が双葉期に達した時に、製剤例２に準じて調製した水
和剤を水で所定濃度に希釈し、スプレーガンを用いて、
１鉢当り５ｄ散布した。散布液風乾後、キュウリ灰色か
び病菌の液体培養菌体摩砕液を噴霧接種した。温室内で
３日間培養した後、下記の基準にしたがい発病葉数を調
査した。その結果を第２表に示す。Test Example 1 (Cucumber gray mold control effect) - When cucumbers (variety: Sumo Hanshiro), which were sown in a square pot with side 91 and 12 seeds per pot, reached the bifoliate stage, water prepared according to Formulation Example 2 was applied. Dilute the Japanese additive with water to the specified concentration, use a spray gun,
Sprayed 5d per pot. After the sprayed liquid was air-dried, a liquid cultured cell suspension of cucumber gray mold fungus was spray inoculated. After culturing in a greenhouse for 3 days, the number of diseased leaves was investigated according to the following criteria. The results are shown in Table 2.
調査基準
発病指数 ０・・・病斑なし
１・・・発病面積が葉面積の３未満
２・・・発病面積が葉面積のＺ以上％未満３・・・発病
面積が葉面積の％以上
第２表Survey standard disease index 0...No lesions 1...Infected area is less than 3 of the leaf area 2...Infected area is Z or more and less than % of the leaf area 3...Infected area is more than % of the leaf area 2 tables
Claims (1)
１はアルキル基、アルコキシ基、ハロゲン原子、プロピ
ニル基またはトリメチルシリルエチニル基を示し、Ｒ＿
２はアルキル基、アルコキシ基、プロピニル基、ハロゲ
ン置換プロピニルオキシ基またはトリメチルシリルエチ
ニル基を示す。但し、Ａがメチル基のとき、Ｒ＿１はＣ
＿２以上のアルキル基、アルコキシ基、ヨウ素原子、フ
ッ素原子、臭素原子、プロピニル基またはトリメチルシ
リルエチニル基を示し、Ｒ＿２はＣ＿２以上のアルキル
基、アルコキシ基、プロピニル基、ハロゲン置換プロピ
ニルオキシ基またはトリメチルシリルエチニル基を示す
。）で表わされる２−置換スルホニルピリミジン誘導体
。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, A represents an alkyl group or a benzyl group, R_
1 represents an alkyl group, an alkoxy group, a halogen atom, a propynyl group or a trimethylsilylethynyl group, and R_
2 represents an alkyl group, an alkoxy group, a propynyl group, a halogen-substituted propynyloxy group, or a trimethylsilylethynyl group. However, when A is a methyl group, R_1 is C
_2 or more alkyl group, alkoxy group, iodine atom, fluorine atom, bromine atom, propynyl group, or trimethylsilylethynyl group, R_2 is C_2 or more alkyl group, alkoxy group, propynyl group, halogen-substituted propynyloxy group, or trimethylsilylethynyl group shows. ) A 2-substituted sulfonylpyrimidine derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61167066A JPH07121919B2 (en) | 1986-07-16 | 1986-07-16 | 2-Substituted sulfonylpyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61167066A JPH07121919B2 (en) | 1986-07-16 | 1986-07-16 | 2-Substituted sulfonylpyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6323870A true JPS6323870A (en) | 1988-02-01 |
| JPH07121919B2 JPH07121919B2 (en) | 1995-12-25 |
Family
ID=15842772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61167066A Expired - Lifetime JPH07121919B2 (en) | 1986-07-16 | 1986-07-16 | 2-Substituted sulfonylpyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07121919B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008368A (en) * | 2016-06-22 | 2016-10-12 | 连云港笃翔化工有限公司 | 2-hydrocarbonmercapto-4,6-dialkoxypyrimidine compounds synthesized from 2,4,6-trichloropyrimidine with one-pot method and preparation method of compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5052075A (en) * | 1973-09-12 | 1975-05-09 |
-
1986
- 1986-07-16 JP JP61167066A patent/JPH07121919B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5052075A (en) * | 1973-09-12 | 1975-05-09 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008368A (en) * | 2016-06-22 | 2016-10-12 | 连云港笃翔化工有限公司 | 2-hydrocarbonmercapto-4,6-dialkoxypyrimidine compounds synthesized from 2,4,6-trichloropyrimidine with one-pot method and preparation method of compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07121919B2 (en) | 1995-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5089581B2 (en) | 1,2-Benzisothiazole derivatives and plant disease control agents for agriculture and horticulture | |
| JPS63141971A (en) | Pyrimidine derivative and germicide for agriculture and horticulture | |
| JP2000336080A (en) | Isothiazolecarboxamides | |
| US4228165A (en) | Phenyl isothiocyanate derivatives and their production | |
| JPS6323870A (en) | 2-substituted sulfonylpyrimidine derivative | |
| KR100297332B1 (en) | Pyridyl-1,2,4-thiadiazole as a pest control agent | |
| KR980009261A (en) | 1,2,3-benzothiadiazole derivatives | |
| JPS58213758A (en) | Heteroarylthiovinyl compound, manufacture and use as agricultural drug | |
| JP2503547B2 (en) | Carbamoyltriazole derivative, its production method and herbicide containing it as an active ingredient | |
| JPH0256469A (en) | Pyridazinone derivative and herbicide | |
| JPH0688975B2 (en) | 0-Substituted 3-oxypyridinium salt and fungicide containing the compound | |
| JPS6325590B2 (en) | ||
| JPH05194449A (en) | 3-(4-bromophenyl)-5-methylsulfonyl-1,2,4-thiadiazole | |
| JPS6078966A (en) | Trichloroacryloyloxime derivative, production thereof and agricultural germicide | |
| JPH04124108A (en) | Control agent of phycomycete plant disease, containing 2-chloropyridine derivative as active ingredient | |
| JPS5885863A (en) | Dihalophenyl substituted ethylsulfonylpridine 1-oxide derivative | |
| JPS6299305A (en) | Agricultural and horticultural germicide | |
| JPS6327482A (en) | Herbicidal composition | |
| JPH05255269A (en) | Phenylimidazole compound, its production and agricultural and horticultural germicide comprising same | |
| JPS627907B2 (en) | ||
| JPH07110859B2 (en) | 1-trifluoromethylcarboline derivative, method for producing the same, and plant disease control agent containing the same | |
| JPH0788281B2 (en) | Agro-horticultural fungicide | |
| KR930000150B1 (en) | Pyrimidine derivative process for preparing same and agricutral or horticultural fungicd al composition containing same | |
| JPH07291970A (en) | Pyrazole derivative and herbicide using the same | |
| JPH0413668A (en) | 2-anilinopyrimidine derivative, its production and fungicide for agricultural and horticultural use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |