JPH0495077A - 2-iodopropargyloxypyrimidine derivative and fungicide for agricultural and horticultural use - Google Patents
2-iodopropargyloxypyrimidine derivative and fungicide for agricultural and horticultural useInfo
- Publication number
- JPH0495077A JPH0495077A JP21141090A JP21141090A JPH0495077A JP H0495077 A JPH0495077 A JP H0495077A JP 21141090 A JP21141090 A JP 21141090A JP 21141090 A JP21141090 A JP 21141090A JP H0495077 A JPH0495077 A JP H0495077A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- alkoxy
- formula
- halogen atom
- 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.)
- Pending
Links
- 239000000417 fungicide Substances 0.000 title claims abstract description 11
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 9
- OAOQJBULEGQFPV-UHFFFAOYSA-N 2-iodo-4-prop-2-ynoxypyrimidine Chemical class IC1=NC=CC(OCC#C)=N1 OAOQJBULEGQFPV-UHFFFAOYSA-N 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 28
- -1 phenoxy, cyano, phenyl Chemical group 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 8
- JYQJMGROXSSXDR-UHFFFAOYSA-N 3-iodoprop-2-yn-1-ol Chemical compound OCC#CI JYQJMGROXSSXDR-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 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 17
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 241000233866 Fungi Species 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 240000008067 Cucumis sativus Species 0.000 description 8
- 241000209094 Oryza Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000007605 air drying Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 230000000887 hydrating effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 241000223600 Alternaria Species 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- 241000233614 Phytophthora Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000010432 cotyledon development Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000206761 Bacillariophyta Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001361634 Rhizoctonia Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IWEPSGGZINUNSM-UHFFFAOYSA-N 2-sulfonyl-1h-pyrimidine Chemical class O=S(=O)=C1N=CC=CN1 IWEPSGGZINUNSM-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000228457 Leptosphaeria maculans Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZGBSOTLWHZQNLH-UHFFFAOYSA-N [Mg].S(O)(O)(=O)=O Chemical compound [Mg].S(O)(O)(=O)=O ZGBSOTLWHZQNLH-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 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
- 239000012752 auxiliary agent Substances 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 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
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000002554 disease preventive effect Effects 0.000 description 1
- 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 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
- 239000002552 dosage form Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000002917 insecticide Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000012184 tortilla Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000004563 wettable powder 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、新規な２−ヨードプロパルギルオキシピリミ
ジン誘導体及び該化合物を有効成分として含有する農園
芸用殺菌剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel 2-iodopropargyloxypyrimidine derivative and an agricultural and horticultural fungicide containing the compound as an active ingredient.
（従来の技術）
従来からピリミジン誘導体に関しては種々の研究がなさ
れている。農園芸用殺菌剤として活性を示すピリミジン
誘導体としては、例えばヨードプロパルギルオキシ基を
４位に置換した化合物が特することである。(Prior Art) Various studies have been conducted on pyrimidine derivatives. Pyrimidine derivatives that exhibit activity as agricultural and horticultural fungicides include, for example, compounds in which an iodopropargyloxy group is substituted at the 4-position.
（課題を解決するための手段）
本発明者らは更に有用な殺菌剤を開発すべくヨードプロ
パルギルオキシ基をピリミジン環の２位に配した化合物
を種々合成し、その殺菌活性について検討を重ねた結果
、本発明化合物が水稲及び園芸作物の各種病害に幅広く
優れた効果を示し、作物に対しては薬害を示さないとい
う優れた特徴を有することを見いだし、本発明を完成し
たものである。(Means for Solving the Problems) In order to develop more useful fungicides, the present inventors synthesized various compounds in which an iodopropargyloxy group was placed at the 2-position of the pyrimidine ring, and repeatedly investigated their fungicidal activity. As a result, we have completed the present invention by discovering that the compound of the present invention exhibits a wide range of excellent effects against various diseases of paddy rice and horticultural crops, and has the excellent feature of not causing chemical damage to crops.
即ち、本発明の２−ヨードプロパルギルオキシピリミジ
ン誘導体は、一般式［Ｎ
（発明が解決しようとする課題）
しかしながら、これら公知化合物の有する殺菌効果は必
ずしも十分満足できるものとはいえない。That is, the 2-iodopropargyloxypyrimidine derivative of the present invention has the general formula [N (Problem to be Solved by the Invention) However, the bactericidal effects of these known compounds are not necessarily fully satisfactory.
即ち、本発明は更に改良された新規なヨードプロパルギ
ルオキシ基置換ピリミジン誘導体を提供（式中、Ｒ゛は
水素原子、ハロゲン原子、アルキル基、アルコキシ基、
ハロアルキル基、フェノキシ基、シアノ基、フェニル基
またはアルコキシカルボニル基を示し、Ｒ゛は水素原子
、ハロゲン原子、アルキル基、アルコキシ基またはアル
コキシカルボニル基を示し、Ｒ″は水素原子、ハロゲン
原子、アルキル基、アルコキシ基、ハロアルキル基、フ
ェニル基、アルコキシカルボニル基、フェノキシ基（−
個以上のハロゲン原子、アルキル基、アルコキシ基また
はハロアルキル基で置換されていてもよい）、アルケニ
ルオキシ基、アルコキシアルコキシ基またはハロアルキ
ニルオキシ基を示す。）で表される。That is, the present invention provides further improved novel iodopropargyloxy group-substituted pyrimidine derivatives (wherein R' is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group,
Represents a haloalkyl group, phenoxy group, cyano group, phenyl group, or alkoxycarbonyl group, R'' represents a hydrogen atom, halogen atom, alkyl group, alkoxy group, or alkoxycarbonyl group, and R'' represents a hydrogen atom, a halogen atom, or an alkyl group. , alkoxy group, haloalkyl group, phenyl group, alkoxycarbonyl group, phenoxy group (-
halogen atoms, alkyl groups, alkoxy groups, or haloalkyl groups), alkenyloxy groups, alkoxyalkoxy groups, or haloalkynyloxy groups. ).
次に、一般式〔■〕で表される本発明化合物を第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
。Next, the compounds of the present invention represented by the general formula [■] are illustrated in Table 1. Compound numbers are referenced in the following description.
第１表
（以下余白）
第１表つづき
慎１表つづき
本発明化合物は例えば以下に示す製造方法に従って製造
することができる。Table 1 (blank below) Table 1 (Continued) Table 1 (Continued) The compound of the present invention can be produced, for example, according to the production method shown below.
［Ｉ［］ ［
＋］（式中、Ｒｏ、Ｒ”及びＲｏは前記と同じ意味を示
し、Ｒ“はアルキル基、ベンジル基または置換ベンジル
基を示す。）
即ち、本発明化合物ＣＩ］は、３−ヨードプロパルギル
アルコールを溶媒に溶かし、アルカリ金属またはアルカ
リ金属水酸化物でアルコラードとした後、一般式［ＩＩ
］で示される２−（アルキル、ジン類を加え、反応温度
−２０℃から溶媒の沸点の範囲、好ましくは１０℃〜４
０℃の範囲で反応させることにより製造することができ
る。[I[] [
+] (In the formula, Ro, R" and Ro have the same meanings as above, and R" represents an alkyl group, a benzyl group or a substituted benzyl group.) That is, the compound CI] of the present invention is 3-iodopropargyl alcohol was dissolved in a solvent and converted into an alcoholade with an alkali metal or alkali metal hydroxide, and then the general formula [II
] 2-(alkyl, zine) is added, and the reaction temperature ranges from -20°C to the boiling point of the solvent, preferably 10°C to 4°C.
It can be produced by reacting at a temperature of 0°C.
本反応に使用できる溶媒としては、例えばベンゼン、ト
ルエン、キシレン等の芳香族炭化水素、Ｎ、Ｎ−ジメチ
ルホルムアミド、Ｎ、Ｎ−ジメチルアセトアミド、ジメ
チルスルホキシド等の不活性な極性溶媒、ジエチルエー
テル、ジオキサン、テトラヒドロフラン等のエーテル類
、アセトン、メチルエチルケトン、シクロヘキサノン等
のケトン類及びアセトニトリル、プロピオニトリル等の
ニトリル類を挙げることができる。ベンゼン、トルエン
等の芳香族炭化水素を用いると、効率よく化合物［１］
を製造することができる。Examples of solvents that can be used in this reaction include aromatic hydrocarbons such as benzene, toluene, and xylene, inert polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide, diethyl ether, and dioxane. , ethers such as tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, and nitrites such as acetonitrile and propionitrile. When aromatic hydrocarbons such as benzene and toluene are used, compounds [1]
can be manufactured.
尚、一般式［■］で示される出発物質の大部分は、それ
自体殺菌活性を有する新規物質であるが、新規な出発物
質である２−（アルキル、ベンジルまたは置換ベンジル
）スルホニルピリミジン類を第２表に例示する。Most of the starting materials represented by the general formula [■] are new substances that themselves have bactericidal activity, but the new starting materials, 2-(alkyl, benzyl or substituted benzyl) sulfonylpyrimidines, are Examples are shown in Table 2.
また、３−ヨードプロパルギルアルコールは特開昭４９
−２４４４５号公報に記載された方法に従って製造する
ことができる。In addition, 3-iodopropargyl alcohol is
It can be produced according to the method described in JP-A-24445.
第２表
第２表つづき
（以下余日）
次に実施例及び参考例を挙げて本発明化合物及び中間体
の製造法を具体的に説明する。Table 2 Continued from Table 2 (continued below) Next, the method for producing the compounds and intermediates of the present invention will be specifically explained with reference to Examples and Reference Examples.
実施例１
４−クロロ−６−ニトキシー２−（３−ヨードプロパル
ギルオキシ）ピリミジン（化合物番号７）の製造
６０％水素化ナトリウム０．４４ ｇをｎ−ヘキサンで
洗浄した後、ベンゼン５０ｍ１に懸濁した。Example 1 Production of 4-chloro-6-nitoxy 2-(3-iodopropargyloxy)pyrimidine (compound number 7) 0.44 g of 60% sodium hydride was washed with n-hexane and then suspended in 50 ml of benzene. did.
これに３−ヨードプロパルギルアルコール２．７ｇを加
え、室温下で３時間攪拌した。次に４−クロロ−６−ニ
トキシー２−メチルスルホニルピリミジン２．４ｇを加
え、室温下で２時間攪拌した。2.7 g of 3-iodopropargyl alcohol was added to this, and the mixture was stirred at room temperature for 3 hours. Next, 2.4 g of 4-chloro-6-nitoxy-2-methylsulfonylpyrimidine was added, and the mixture was stirred at room temperature for 2 hours.
した後、減圧下に濃縮した。残渣をシリカゲルクロマト
グラフィー（展開溶媒：酢酸エチル／ ｎ −ヘキサン
）にて精製し、無色プリズム状結晶の目的化合物１．９
ｇ（収率５５．９％）を得た。融点８０〜８３℃
実施例２
２−（３−ヨードプロパルギルオキシ）−４フェノキシ
−６−トリフルオロメチルピリミジン（化合物番号２０
）の製造
６０％水素化ナトリウム０．６ｇをｎ−ヘキサンで洗浄
した後、トルエン８０ｍ１に懸濁した。これに３−ヨー
ドプロパルギルアルコール２．７ｇを加え、室温下で２
時間攪拌した。次に２−メチルスルホニル−４−フェノ
キシ−６−トリフルオロメチルピリミジン２．９ｇを加
え、室温下で２］条時間攪拌した。反応混合物に水５０
ｍ ｌ及びトルだ
渣をシリカゲルクロマトグラフィー（展開溶媒。After that, it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: ethyl acetate/n-hexane) to obtain the target compound 1.9 as colorless prismatic crystals.
g (yield 55.9%) was obtained. Melting point 80-83°C Example 2 2-(3-iodopropargyloxy)-4phenoxy-6-trifluoromethylpyrimidine (Compound No. 20
After washing 0.6 g of 60% sodium hydride with n-hexane, it was suspended in 80 ml of toluene. Add 2.7 g of 3-iodopropargyl alcohol to this and
Stir for hours. Next, 2.9 g of 2-methylsulfonyl-4-phenoxy-6-trifluoromethylpyrimidine was added, and the mixture was stirred at room temperature for 2 hours. 50% water to the reaction mixture
ml and the tortilla residue were subjected to silica gel chromatography (developing solvent.
酢酸エチル／ｎ−ヘキサン）にて精製し、黄褐色透明粘
稠液体の目的化合物２．５ｇ（収率５９．５％）を得た
。屈折率ｎ１°＝１．５６１８実施例３
４．６−ジクロロ−２（３−ヨードプロパルギルオキシ
）−５−メトキシピリミジン（化合物番号４４）の製造
６０％水素化ナトリウム１．３ ｇをｎ−ヘキサンで洗
浄した後、ベンゼン１５０ｍ１に懸濁した。The product was purified using ethyl acetate/n-hexane) to obtain 2.5 g (yield: 59.5%) of the target compound as a yellow-brown transparent viscous liquid. Refractive index n1°=1.5618 Example 3 Production of 4.6-dichloro-2(3-iodopropargyloxy)-5-methoxypyrimidine (Compound No. 44) 1.3 g of 60% sodium hydride was added to n-hexane. After washing with water, it was suspended in 150 ml of benzene.
これに３−ヨードプロパルギルアルコール６．２ｇを加
え、室温下で３時間攪拌した。次に４，６−ジクロロ−
５−メトキシ−２−メチルスルホニルピリミジン７．３
ｇを加え、室温下で２時間攪拌した。反応混合物に水５
０ｍ１及び酢酸エチル１００ｍ１を加え、有機層を水洗
、硫酸マグネジ溶液へ７０％メタクロロ過安息香酸５．
３ｇを室温下に加え、室温で１時間、次いで５０℃で３
０分間撹拌して反応終了とした。反応混合物を室温まで
冷却した後、濾過し、濾液を水、亜硫酸ナトリウム水溶
液、水の順で洗い、有機層を塩化カルシウムで乾燥し、
減圧下に濃縮した。残渣をシリカゲルクロマトグラフィ
ー（展開溶媒：酢酸エチル／ｎ−ヘキサン）にて精製し
、橙色粘稠液体の目的化合物４．０ｇ（収率７７．０％
）を得た。屈チル／ｎ−ヘキサン）にて精製し、無色プ
リズム参考例（中間体１２の製造法）
４−（４−ｔｅｒｔ−ブチルフェノキシ）−２−メチル
スルホニル−６−トリフルオロメチルピリジンの製造
クロロホルム８０ｍ１へ４− （４−ｔｅｒｔ −ブチ
ルフェノキシ）−２−メチルチオ−６−トリフルオロメ
チルピリジン４．８ｇを溶解し、この本発明の農園芸用
殺菌剤は一般式［１１で示される２−ヨードプロパルギ
ルオキシピリミジン誘導体を有効成分として含有してな
る。6.2 g of 3-iodopropargyl alcohol was added to this, and the mixture was stirred at room temperature for 3 hours. Then 4,6-dichloro-
5-Methoxy-2-methylsulfonylpyrimidine 7.3
g was added thereto, and the mixture was stirred at room temperature for 2 hours. Add 5 liters of water to the reaction mixture
0 ml and 100 ml of ethyl acetate were added, the organic layer was washed with water, and 70% metachloroperbenzoic acid was added to the sulfuric acid Magnesium solution.5.
3g was added at room temperature and incubated at room temperature for 1 hour, then at 50°C for 3 hours.
The reaction was completed after stirring for 0 minutes. After cooling the reaction mixture to room temperature, it was filtered, the filtrate was washed with water, an aqueous sodium sulfite solution, and water in that order, and the organic layer was dried with calcium chloride.
Concentrate under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: ethyl acetate/n-hexane) to obtain 4.0 g of the target compound as an orange viscous liquid (yield 77.0%).
) was obtained. Reference example (method for producing intermediate 12) Production of 4-(4-tert-butylphenoxy)-2-methylsulfonyl-6-trifluoromethylpyridine Chloroform 80ml By dissolving 4.8 g of 4-(4-tert-butylphenoxy)-2-methylthio-6-trifluoromethylpyridine into the 2-iodopropargyl pyridine of the general formula [11] It contains an oxypyrimidine derivative as an active ingredient.
本発明化合物を農園芸用殺菌剤として使用する場合には
、その目的に応じて有効成分を適当な剤層に製剤して使
用することが望ましい。通常は有効成分を不活性な液体
または固体の担体で希釈し、必要に応じて界面活性側、
分散剤または他の補助剤を加え、粉剤、水和剤、乳刑、
粒剤等の製剤形態で使用する。好適な担体としては、例
えばタルク、ベントナイト、クレー、カオリン、珪藻土
。When the compound of the present invention is used as a fungicide for agriculture and horticulture, it is desirable to formulate the active ingredient into a suitable agent layer depending on the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, the surface-active side,
Adding dispersants or other auxiliaries, powders, wettable powders, emulsion,
It is used in formulations such as granules. Suitable carriers include, for example, talc, bentonite, clay, kaolin, diatomaceous earth.
ホワイトカーボン、バーミキュライト、消石灰、珪砂、
硫安、Ｉ素等の個体担体、イソプロピルアルコール、キ
シレン、シクロヘキサノン、メチルナフタレン等の液体
担体等が挙げられる。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スルホン酸塩、アルコール硫酸
エステル塩、アルキルアリールスルホン酸塩、リグニン
スルホン１酸塩、ポリオキシエチレングリコールエーテ
ル、本発明の農園芸用殺菌剤の施用量は、使用される化
合物の種類、対象病害、発生傾向、被害の程度、環境条
件、使用する剤型などによって変るが、粉剤及び粒剤の
ようにそのまま使用する場合には、有効成分で１０アー
ル当り０，１ｇ〜５Ｋｇ、好ましくは１ｇ−ＩＫｇの範
囲から適宜選ぶのがよい。また、乳剤及び水和剤のよう
に液状で使用する場合には、０．．１ ｐｐｍ 〜１０
．ＯＯＯｐｐｍ。White carbon, vermiculite, slaked lime, silica sand,
Examples include solid carriers such as ammonium sulfate and elemental I, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. As surfactants and dispersants,
For example, dinaphthyl methanesulfonate, alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, the application amount of the agricultural and horticultural fungicide of the present invention depends on the type of compound used. Although it varies depending on the target disease, incidence tendency, degree of damage, environmental conditions, dosage form used, etc., when used as is such as powders and granules, the active ingredient is preferably 0.1 g to 5 kg per 10 ares. is preferably selected from the range of 1g-IKg. In addition, when used in liquid form such as emulsions and wettable powders, 0. ．． 1 ppm ~10
．． OOOppm.
好ましくは１０〜３．ＯＯＯｐｐｍの範囲がら適盲選ぶ
のがよい。Preferably 10-3. It is best to choose the appropriate one from the OOOppm range.
本発明化合物ハ子嚢菌類（Ａｓｃｏｍｙｃｅｔｅｓ）
、不等が挙げられる。補助剤としてはカルボキシメチル
セルロース、ポリエチレングリコール等が挙げられる。Compound of the present invention Ascomycetes
, inequality can be mentioned. Examples of auxiliary agents include carboxymethyl cellulose and polyethylene glycol.
これらの製剤は適宜な濃度に希釈して散布するか、また
は直接施用する。These preparations can be diluted to an appropriate concentration and sprayed, or applied directly.
有効成分の配合割合は、必要に応じ適宜選ばれるが、粉
剤及び粒剤とする場合は、０．１〜２０％（重量）、ま
た乳剤及び水和剤とする場合は、５〜８０％（重量）が
適当である。The blending ratio of the active ingredients is selected as appropriate depending on the need, but it is 0.1 to 20% (by weight) for powders and granules, and 5 to 80% (by weight) for emulsions and wettable powders. weight) is appropriate.
菌に起因する植物病を有効に防除できる。これら菌に属
する植物病菌としては、スフエロテヵ（並ｈａｅｒｏｔ
ｈｅｃａ ）属のうどんこ病菌（並立と匹ｈｅｃａ ｆ
皿ユ旦胆）、ビリキュラリア（ｈ：且止払■）属のいも
ち病菌（ｈ二且佳払二匹ムと）、リゾクトニア（Ｒｈｉ
ｚｏｃｔｏｎｉａ）属の紋枯病菌（Ｒｈｉｚｏｃｔｏｎ
ｉａｓｏｌａｎｉ） 、アルタナリア（Ａｌｔｅｒｎａ
ｒｉａ）属の黒すす病菌（Ａｌｔｅｒｎａｒｉａ ｂｒ
ａｓｓｉｃｉ−ｃｏｌａ） 、シュードベロノスボラ（
Ｐｓｅｕｄｏ ｅｒｏｎｏｓ ｏｒａ）属のべと病菌（
Ｐｓｅｕｄｏ ｅｒｏｎｏｓ ｏｒａ ｈｕｍｕｌｉま
たは７胚■凹匪坦ｃｕｂｅｎｓｉｓ） 、プラスモパラ
（旦…五…ｒａ）属のべと病菌（Ｐｌａｓ＋＋＋ｏｐａ
ｒａ ｖｉｔｉｃｏｌａ） 、ペロノスボラ（Ｐｅｒｏ
ｎｏｓ ｏｒａ）属のべと病菌（Ｐｅｒｏｎ匹三二目巨
鈷またはＰ、ｂｒａｓｓｉｃａｅ） 、フィトフトラ（
Ｐｈ ｔｏ ｈｔｈｏｒａ）属の疫病菌（Ｐｈ ｔｏ
ｈｔｈｏｒａ １ｎｆｅｓｔａｎｓ）等を例示すること
ができる。Plant diseases caused by fungi can be effectively controlled. Plant disease fungi belonging to these fungi include Sphaerotheca
Powdery mildew fungi of the genus heca
Blast fungus of the genus Viricularia (h: 作术), Rhizoctonia (Rhi)
Rhizocton of the genus Zoctonia
iasolani), Alternaria (Alterna)
Alternaria br of the genus Alternaria br.
assici-cola), Pseudoberonosvora (
Pseudo eronos ora) genus downy mildew fungi (
Plas+++ opa
ra viticola), Peronosvora (Pero
downy mildew fungi (P. brassicae) of the genus P. nos ora, Phytophthora (
Phytophthora (Ph to hthora) genus Phytophthora (Ph to hthora)
hthora 1nfestans), etc.
更に、本発明化合物は必要に応じて殺虫剤、殺菌剤、除
草剤、植物生長調節剤、肥料等と混用してもよい。Furthermore, the compound of the present invention may be used in combination with insecticides, fungicides, herbicides, plant growth regulators, fertilizers, etc., if necessary.
製剤例１ 粉剤
化合物（２０）５％、珪藻±５％、クレー９３％を均一
に混合粉砕して粉剤とした。Formulation Example 1 Powder 5% of compound (20), ±5% of diatoms, and 93% of clay were uniformly mixed and ground to obtain a powder.
製剤例２ 水和剤
化合物（２０）５０％、珪藻±４５％、ジナフチルメタ
ンジスルホン酸ナトリウム２％、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した。Formulation Example 2 Wettable powders 50% of Compound (20), 45% of diatoms, 2% of sodium dinaphthylmethane disulfonate, and 3% of sodium ligninsulfonate were uniformly mixed and ground to prepare a wettable powder.
製剤例３ 乳剤
化合物（２０）３０％、シクロへキサノン２０％、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シウム４％、メチルナフタ
リン３５％を混合撹拌して乳剤とした。Formulation Example 3 An emulsion was prepared by mixing and stirring 30% of emulsion compound (20), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate, and 35% of methylnaphthalene.
製剤例４ 粒剤
トヒ合物（２０）５％、ラウリルアルコール硫酸エステ
ルのナトリウム塩２％、リグニンスルホン酸１％、クレ
ー８６％を均一に混合して粉砕する。この混合物に水２
０％を加えて練合し、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、乾燥して粒剤を得る。Formulation Example 4 5% of granulated tohi compound (20), 2% of sodium salt of lauryl alcohol sulfate, 1% of lignin sulfonic acid, and 86% of clay are uniformly mixed and pulverized. Add 2 ounces of water to this mixture
Add 0% and knead, and use an extrusion granulator to make 14 to 32
After processing into mesh granules, they are dried to obtain granules.
次に本発明の農園芸用殺菌剤の奏する効果を試験例を挙
げて具体的に説明する。Next, the effects of the agricultural and horticultural fungicide of the present invention will be specifically explained using test examples.
試験例１ イネいもち病予防効果試験
直径９ｃｍの白磁製鉢に水稲種子（品種：愛知旭）を２
０粒づつ播種し、温室内で３〜４週間育成した。第４葉
展開後の幼苗に製剤例２に準じて調製した水和剤を、有
効成分濃度が５０ｐｐｍになるように水で希釈し、■鉢
当たり１０ｍ１散布した。風乾後、いもち病菌（ｈ二μ
」払旦旦ｕ憇）の胞子懸濁液を噴霧接種し、２５℃の温
室内に入れた。接種５日後に病斑を数え、下記計算式に
従い防除価を算出した。結果を第３表に示す。Test Example 1 Rice blast prevention effect test Two rice seeds (variety: Aichi Asahi) were placed in a white porcelain pot with a diameter of 9 cm.
0 seeds were sown and grown in a greenhouse for 3 to 4 weeks. A hydrating powder prepared according to Formulation Example 2 was diluted with water to an active ingredient concentration of 50 ppm, and 10 ml of the solution was sprayed on the seedlings after the fourth leaf had developed per pot. After air-drying, blast fungus (h2μ
The plants were inoculated by spraying with a spore suspension of ``Fudan dan u 憇'' and placed in a greenhouse at 25°C. Five days after inoculation, the lesions were counted and the control value was calculated according to the formula below. The results are shown in Table 3.
第３表
１号公報記載の下記化合物を製剤例２に準じ製剤試験例
２ イネ紋枯病予防効果試験
直径７ｃｍの素焼鉢に水稲種子（品種、全南風）を１５
粒ずつ播種し、温室内で４〜５週間育成した。第５葉展
開後の幼苗に製剤例２に準じて調製した水和剤を、有効
成分濃度が５００ｐｐｍになるように水で希釈し、ｌ鉢
当りｌｏｍｌ散布した。Table 3 Preparation Test Example 2 Preventive effect test on rice sheath blight using the following compounds described in Publication No. 1 according to Formulation Example 2. 15 paddy rice seeds (variety: Zennanpu) were placed in a clay pot with a diameter of 7 cm.
Seeds were sown one by one and grown in a greenhouse for 4 to 5 weeks. A hydrating powder prepared according to Formulation Example 2 was diluted with water to give an active ingredient concentration of 500 ppm and sprayed on the seedlings after developing the fifth leaf in an amount of 1 loml per pot.
風乾後、モミガラフスマ培地で７日間培養した紋枯病菌
（Ｒｈｉｚｏｃｔｏｎｉａ ５ｏｌａｎｉ）を株元に接
種し、第４表
評価基準
Ａクラス
Ｄクラス
Ｃクラス
Ｄクラス
防除価９０％以上
〃 ８０％以上〜９０％未満
〃 ５０％以上〜８０％未満
５０％未満
第３表つづき
第４表つづき
（以下余白）
試験例３ キュウリベと病予防効果試験９ ｃ ｍ Ｘ
９ ｃ ｍの塩化ビニール製鉢各々にキュウリ種子（
品種、相接半白）を１２粒づつ播種し、温室内で７日間
育成させた。子葉展開後の幼苗に実施例２に準じて調製
した水和剤を、有効成分濃度が５０ｐｐｍになるように
水で希釈し、ｌ針当たりｌｏｍｌを散布した。風乾後キ
ュウリベと病菌（Ｐｓｅｕｄｏ ｅｒｏｎｏｓ ｏｒａ
ｃｕｂｅｎｓｉｓ）の胞子懸濁液評価基準
Ａクラス
Ｂクラス
Ｃクラス
Ｄクラス
防除価９０％以上
〃 ７０％以上９０％未満
〃 ４０％以上７０％未満
ｌ ４０％未満
（以下余白）
発病が認められない葉数
発病面積 １７３未満の葉数
１／３以上２／３未満の葉数
２７３以上の葉数
（％） ；
発病程度
ｎ ：
ｎ ：
ｎ ：
ｎ ：
発病度
Ｎ
Ｎは調査全葉数を示す。After air drying, inoculate the root blight fungus (Rhizoctonia 5olani) cultured for 7 days in a rice grain medium and use Table 4 Evaluation Criteria A Class D Class C Class D Class Control value 90% or more〃 80% or more - 90 Less than % 50% or more - less than 80% less than 50% Table 3 continued Table 4 continued (margins below) Test Example 3 Cucumber and Disease Prevention Effect Test 9 cm X
Place cucumber seeds (
Twelve seeds of the cultivar, 20-year-old (Half White) were sown at a time and grown in a greenhouse for 7 days. A hydrating agent prepared according to Example 2 was diluted with water to give an active ingredient concentration of 50 ppm, and LOml per needle was sprayed onto the seedlings after cotyledon development. After air drying, cucumbers and diseased bacteria (Pseudo eronos ora)
Spore suspension evaluation criteria for A class B class C class D control value 90% or more〃 70% or more but less than 90%〃 40% or more and less than 70%l Less than 40% (hereinafter referred to as margin) Leaves with no disease symptoms Number of diseased areas Number of leaves less than 173 Number of leaves 1/3 or more and less than 2/3 Number of leaves 273 or more (%); Disease severity n: n: n: n: disease severity N N indicates the total number of leaves investigated.
第５表
第５表つづき
２＼
試験例４ キュウリうどんこ病予防効果試験９ｃｍＸ９
ｃｍの塩ビ製鉢にキュウリ種子（品種：相接半白）を１
２粒づつ播種し、温室内で７日間育成させた。子葉展開
後の幼苗に製剤例２に準じて調整した水和剤を、有効成
分濃度が５００ｐｐｍになるように水で希釈し、１鉢当
たり１０ｍ、ｌ散布した。風乾後、キュウリうどんこ病
菌（Ｓ ｈａｅｒｏｔｈｅｃａ ４）の胞子を接種し、
２５〜３０℃の温室内に入れた。接種１０日後に下記基
準により鉢全体の発病程度を調査した。Table 5 Table 5 continued 2\ Test Example 4 Cucumber powdery mildew preventive effect test 9cm x 9
1 cucumber seed (variety: mutually semiwhite) in a cm PVC pot
Two seeds each were sown and grown in a greenhouse for 7 days. A hydrating agent prepared according to Formulation Example 2 was diluted with water to an active ingredient concentration of 500 ppm and sprayed on the seedlings after cotyledon development at 10 ml per pot. After air drying, spores of cucumber powdery mildew fungus (S haerotheca 4) were inoculated,
It was placed in a greenhouse at 25-30°C. Ten days after inoculation, the degree of disease onset in the entire pot was investigated according to the following criteria.
１：２５％未満の発病面積
２：２５％以上５０％未満の発病面積
３：５０％以上７５％未満の発病面積
４ニア５％以上の発病面積
結果を第６表に示す
第６表
第７表
第６表つづき
試験例５ 小松菜黒すす病予防効果試験９ｃｍＸ９ｃｍ
の塩ビ製鉢に小松菜種子を１２粒づつ播種し、温室内で
７日間育成させた。子葉展開後の幼苗に製剤例２に準じ
て調製した水和剤を、有効成分濃度が５００ｐｐｍにな
るように水で希釈し、１鉢当たりｌｏｍｌ散布した。風
乾後、小松菜黒すす病菌（Ａｌｔｅｒｎａｒｉａ ｂｒ
ａｓｓｉｃｉ−ｃｏｌａ）の胞子懸濁液を噴霧接種し、
３０℃の温室内に入防除価（％）＝
無処理区の平均病斑数
下記基準に従って評価した結果を第７表に示す。1: Affected area of less than 25% 2: Affected area of 25% or more and less than 50% 3: Affected area of 50% or more and less than 75% 4 Affected area of 5% or more The results are shown in Table 6 Table 7 Table 6 Table continued Test Example 5 Komatsuna black soot disease preventive effect test 9cm x 9cm
Twelve komatsuna seeds were sown in PVC pots and grown in a greenhouse for 7 days. A hydrating agent prepared according to Formulation Example 2 was diluted with water to an active ingredient concentration of 500 ppm and sprayed on the seedlings after cotyledon development in an amount of loml per pot. After air drying, Komatsuna black sooty fungus (Alternaria br.
spray inoculation with a spore suspension of Assici-cola),
Pest control value (%) = average number of lesions in untreated area Table 7 shows the results of evaluation according to the following criteria.
評価基準
Ａクラス ： 防除価９０％以上
Ｂクラス ： ８０％以上９０％未満Ｃクラス
： ５０％以上８０％未満Ｃクラス 、
５０％未満
第７表つづき
試験例６ トマト疫病予防効果試験
直径５ｃｍのプラスチックポットにトマト苗（品種：ボ
ンテローザ）を１本移植し、温室内で育成させた。木葉
が３〜４葉展開したトマト幼苗に製剤例２に準じて調整
した水和剤を、有効成分濃度が１１００ｐｐになるよう
に水で希釈し、ｌ針当たり１５ｍ１散布した。風乾後、
トマト疫病菌（Ｐ ｔｈｏ ｈｔｈｏｒａ １ｎｆｅｓ
ｔａｎｓ）の胞子を噴霧接種し２３℃の温室に入れた。Evaluation criteria A class: Control value 90% or more B class: 80% or more but less than 90% C class
: 50% or more and less than 80% C class,
Less than 50% Table 7 continued Test Example 6 Tomato late blight preventive effect test One tomato seedling (variety: Bonterosa) was transplanted into a plastic pot with a diameter of 5 cm and grown in a greenhouse. A hydrating powder prepared according to Formulation Example 2 was diluted with water to give an active ingredient concentration of 1100 pp, and sprayed on tomato seedlings with 3 to 4 leaves developed at 15 ml per 1 needle. After air drying,
Tomato late blight fungus (P thohthora 1nfes)
The cells were spray-inoculated with spores of A. tans) and placed in a greenhouse at 23°C.
接種４日後に下記基準により鉢全体の発病程度を調査し
た。Four days after inoculation, the degree of disease onset in the entire pot was investigated according to the following criteria.
発病指数Ｏ： 発病を認めず
１： １０％未満の発病面積
２： ｔｏ％以上３０％未満の発病面積３： ３０％
以上７５％未満の発病面積４： ７５％以上の発病面積
下記基準に従い評価した結果を第８表に示す。Disease index O: No disease onset 1: Diseased area less than 10% 2: Diseased area more than to% but less than 30% 3: 30%
Affected area of 75% or more 4: Affected area of 75% or more The results of evaluation according to the following criteria are shown in Table 8.
評価基準 Ａクラス ： 発病指数 ０． ＩＢクラ
ス ： ２
Ｃグラス ＝ ３
Ｄクラス ： ４
（以下余白）
第８表
（発明の効果）
本発明の農園芸用殺菌剤は前述の公知化合物と比較して
も、特にキュウリベと病防除剤として卓効を示し、さら
にイネいもち病、イネ紋枯病、キュウリうどんこ病、小
松菜黒すす病及びトマト疫病防除剤としても有効である
。Evaluation criteria A class: Disease index 0. IB class: 2 C grass = 3 D class: 4 (Left below blank) Table 8 (Effects of the invention) The agricultural and horticultural fungicide of the present invention is particularly effective as a cucumber and disease control agent, even when compared with the above-mentioned known compounds. It is highly effective and is also effective as a control agent for rice blast, rice sheath blight, cucumber powdery mildew, komatsuna black soot, and tomato late blight.
特に、各種べと病に対しては高い活性を示し、しかも作
物に薬害を示すことなく残効性、耐雨性に優れると言う
特徴をも併せ持っている。In particular, it shows high activity against various downy mildews, and also has the characteristics of excellent residual efficacy and rain resistance without causing chemical damage to crops.
特許出願人 クミアイ化学工業株式会社外１名Patent applicant: 1 person other than Kumiai Chemical Industry Co., Ltd.
Claims (2)
、アルコキシ基、ハロアルキル基、フェノキシ基、シア
ノ基、フェニル基またはアルコキシカルボニル基を示し
、Ｒ＾２は水素原子、ハロゲン原子、アルキル基、アル
コキシ基またはアルコキシカルボニル基を示し、Ｒ＾３
は水素原子、ハロゲン原子、アルキル基、アルコキシ基
、ハロアルキル基、フェニル基、アルコキシカルボニル
基、フェノキシ基（一個以上のハロゲン原子、アルキル
基、アルコキシ基またはハロアルキル基で置換されてい
てもよい）、アルケニルオキシ基、アルコキシアルコキ
シ基またはハロアルキニルオキシ基を示す。｝で表され
る２−ヨードプロパルギルオキシビリミジン誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ {In the formula, R^1 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a phenoxy group, a cyano group, a phenyl group, or an alkoxycarbonyl group , R^2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkoxycarbonyl group, and R^3
is hydrogen atom, halogen atom, alkyl group, alkoxy group, haloalkyl group, phenyl group, alkoxycarbonyl group, phenoxy group (optionally substituted with one or more halogen atom, alkyl group, alkoxy group or haloalkyl group), alkenyl Indicates an oxy group, an alkoxyalkoxy group, or a haloalkynyloxy group. A 2-iodopropargyloxypyrimidine derivative represented by }.
、アルコキシ基、ハロアルキル基、フェノキシ基、シア
ノ基、フェニル基またはアルコキシカルボニル基を示し
、Ｒ＾２は水素原子、ハロゲン原子、アルキル基、アル
コキシ基またはアルコキシカルボニル基を示し、Ｒ＾３
は水素原子、ハロゲン原子、アルキル基、アルコキシ基
、ハロアルキル基、フェニル基、アルコキシカルボニル
基、フェノキシ基（一個以上のハロゲン原子、アルキル
基、アルコキシ基またはハロアルキル基で置換されてい
てもよい）、アルケニルオキシ基、アルコキシアルコキ
シ基またはハロアルキニルオキシ基を示す。｝で表され
る２−ヨードプロパルギルオキシビリミジン誘導体を有
効成分として含有する農園芸用殺菌剤。(2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ {In the formula, R^1 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a phenoxy group, a cyano group, a phenyl group, or an alkoxycarbonyl group , R^2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkoxycarbonyl group, and R^3
is hydrogen atom, halogen atom, alkyl group, alkoxy group, haloalkyl group, phenyl group, alkoxycarbonyl group, phenoxy group (optionally substituted with one or more halogen atom, alkyl group, alkoxy group or haloalkyl group), alkenyl Indicates an oxy group, an alkoxyalkoxy group, or a haloalkynyloxy group. An agricultural and horticultural fungicide containing a 2-iodopropargyloxypyrimidine derivative represented by } as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21141090A JPH0495077A (en) | 1990-08-09 | 1990-08-09 | 2-iodopropargyloxypyrimidine derivative and fungicide for agricultural and horticultural use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21141090A JPH0495077A (en) | 1990-08-09 | 1990-08-09 | 2-iodopropargyloxypyrimidine derivative and fungicide for agricultural and horticultural use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0495077A true JPH0495077A (en) | 1992-03-27 |
Family
ID=16605498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21141090A Pending JPH0495077A (en) | 1990-08-09 | 1990-08-09 | 2-iodopropargyloxypyrimidine derivative and fungicide for agricultural and horticultural use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0495077A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6427246B1 (en) | 1999-10-12 | 2002-08-06 | Mizuno Corporation | Glove for baseball |
| US6440984B1 (en) | 1998-03-06 | 2002-08-27 | Basf Aktiengesellschaft | Use of aryl-substituted pyrimidines as insecticidal and acaricidal agents |
| US6838463B2 (en) | 2000-09-19 | 2005-01-04 | Sumitomo Chemical Company, Limited | Pyrimidine compounds and their use |
| US7223769B2 (en) | 2002-03-12 | 2007-05-29 | Sumitomo Chemical Company, Limited | Pyrimidine compounds and their use as pesticides |
-
1990
- 1990-08-09 JP JP21141090A patent/JPH0495077A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6440984B1 (en) | 1998-03-06 | 2002-08-27 | Basf Aktiengesellschaft | Use of aryl-substituted pyrimidines as insecticidal and acaricidal agents |
| US6427246B1 (en) | 1999-10-12 | 2002-08-06 | Mizuno Corporation | Glove for baseball |
| US6838463B2 (en) | 2000-09-19 | 2005-01-04 | Sumitomo Chemical Company, Limited | Pyrimidine compounds and their use |
| US7291730B2 (en) | 2000-09-19 | 2007-11-06 | Sumitomo Chemical Company, Limited | Pyrimidine compounds and their use |
| US7223769B2 (en) | 2002-03-12 | 2007-05-29 | Sumitomo Chemical Company, Limited | Pyrimidine compounds and their use as pesticides |
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