JPH0474174A - Benzooxazinyluracil derivative, preparation thereof and herbicide containing the same as active ingredient - Google Patents
Benzooxazinyluracil derivative, preparation thereof and herbicide containing the same as active ingredientInfo
- Publication number
- JPH0474174A JPH0474174A JP2256449A JP25644990A JPH0474174A JP H0474174 A JPH0474174 A JP H0474174A JP 2256449 A JP2256449 A JP 2256449A JP 25644990 A JP25644990 A JP 25644990A JP H0474174 A JPH0474174 A JP H0474174A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- general formula
- methyl
- formula
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 30
- 239000004009 herbicide Substances 0.000 title claims abstract description 11
- 239000004480 active ingredient Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title abstract description 3
- BOZKYCFDGPUIND-UHFFFAOYSA-N 5-(2H-1,2-benzoxazin-3-yl)-1H-pyrimidine-2,4-dione Chemical class O1NC(=CC2=C1C=CC=C2)C=1C(NC(NC=1)=O)=O BOZKYCFDGPUIND-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 4
- 241000196324 Embryophyta Species 0.000 abstract description 43
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012022 methylating agents Substances 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 238000006243 chemical reaction Methods 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 36
- 239000002689 soil Substances 0.000 description 36
- 238000011282 treatment Methods 0.000 description 36
- 239000000839 emulsion Substances 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 238000009472 formulation Methods 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 ligroin Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 244000025254 Cannabis sativa Species 0.000 description 13
- 240000007594 Oryza sativa Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 235000007164 Oryza sativa Nutrition 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- 231100000674 Phytotoxicity Toxicity 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 10
- 240000003173 Drymaria cordata Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241000218691 Cupressaceae Species 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 238000000638 solvent extraction Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 244000064622 Physalis edulis Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 240000001341 Reynoutria japonica Species 0.000 description 5
- 235000018167 Reynoutria japonica Nutrition 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 244000225942 Viola tricolor Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 241001311476 Abies veitchii Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 240000001549 Ipomoea eriocarpa Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 241000208422 Rhododendron Species 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 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
- 241000209763 Avena sativa Species 0.000 description 2
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- 241000234646 Cyperaceae Species 0.000 description 2
- 241000428981 Dyssodia Species 0.000 description 2
- 241001415961 Gaviidae Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920005551 calcium lignosulfonate Polymers 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OVNLPNMCVJZSTA-ARJAWSKDSA-N methyl (z)-2-fluorobut-2-enoate Chemical compound COC(=O)C(\F)=C\C OVNLPNMCVJZSTA-ARJAWSKDSA-N 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-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
- FCBJLBCGHCTPAQ-UHFFFAOYSA-N 1-fluorobutane Chemical compound CCCCF FCBJLBCGHCTPAQ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 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
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
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- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
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- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- ZKRJCMKLCDWROR-ONEGZZNKSA-N ethyl (e)-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C\C(F)(F)F ZKRJCMKLCDWROR-ONEGZZNKSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 230000009931 harmful effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Plural Heterocyclic Compounds (AREA)
- 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、新規なベンゾオキサジルウラシル誘導体、そ
の製造法およびそれを有効成分とする除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel benzoxazyluracil derivative, a method for producing the same, and a herbicide containing the same as an active ingredient.
〈従来の技術〉
これ迄、ある種のベンゾオキサジルウラシル誘導体が除
草剤の有効成分として用いられることが特開平１−１５
７９７７号公報に記載されている。<Prior Art> Until now, it has been reported in JP-A-1-15 that certain benzoxazyluracil derivatives are used as active ingredients of herbicides.
It is described in Publication No. 7977.
〈発明が解決しようとする課題〉
しかしながら、これらの化合物は除草効力が不充分であ
ったり、作物・雑草間の選択性に劣ったりすることから
必ずしも満足すべきものとは言い難い。<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory because their herbicidal efficacy is insufficient or their selectivity between crops and weeds is poor.
く課題を解決するための手段〉
本発明者等はこのような状況に鑑み、種々検討した結果
、ウラシル基に特定の置換基を有するベンゾオキサジル
ウラシル誘導体が上記のような欠点の少ない、優れた除
草効力を有し、かつ作物・雑草間に優れた選択性を示す
化合物であることを見出し本発明に至った。In view of this situation, the present inventors have conducted various studies and found that benzoxazyl uracil derivatives having a specific substituent on the uracil group are superior and have fewer drawbacks as described above. The present inventors have discovered that this compound has excellent herbicidal efficacy and exhibits excellent selectivity between crops and weeds, leading to the present invention.
すなわち、本発明は、一般式
〔式中、Ｒ１はトリフルオロメチル基またはペンタフル
オロエチル基を表わし、Ｒ倉はメチル基またはアミノ基
を表わし、Ｒ３は水素原子またはメチル基を表わし、Ｒ
４はアルキル基、アルケニル基、アルキニル基、ハロア
ルキル基、ハロアルケニル基またはアルコキシアルキル
基を表わし、Ｘは水素原子またはハロゲン原子を表わす
。〕で示されるベンゾオキサジルウラシル誘導体（以下
、本発明化合物と記す。）、その製造法およびそれを有
効成分とする除草剤を提供するものである。That is, the present invention is based on the general formula [wherein R1 represents a trifluoromethyl group or a pentafluoroethyl group, R represents a methyl group or an amino group, R3 represents a hydrogen atom or a methyl group, and R
4 represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, or an alkoxyalkyl group, and X represents a hydrogen atom or a halogen atom. The present invention provides a benzoxazyluracil derivative (hereinafter referred to as the compound of the present invention) represented by the following formula, a method for producing the same, and a herbicide containing the same as an active ingredient.
本発明化合物の中では、Ｒ８が水素原子、Ｒ６がアルキ
ニル基、Ｘがフッ素原子である化合物が好ましく、例え
ば、１−〔７−フルオロ−４−プロパルギル−２８−１
，４−ベンゾオキサジン−３（４Ｈ）−オン−６−イル
〕−３−メチル−４−トリフルオロメチル−１，２，３
，６−テトラヒドロビリミジン−２，６−ジオンがあげ
られる。Among the compounds of the present invention, compounds in which R8 is a hydrogen atom, R6 is an alkynyl group, and X is a fluorine atom are preferred, such as 1-[7-fluoro-4-propargyl-28-1
,4-benzoxazin-3(4H)-one-6-yl]-3-methyl-4-trifluoromethyl-1,2,3
, 6-tetrahydrobyrimidine-2,6-dione.
次に本発明化合物の製造法について説明する。Next, a method for producing the compound of the present invention will be explained.
（製法Ａ）
本発明化合物の中でＲ１がメチル基である化合物は、一
般式
〔式中、Ｒ’ 、Ｒ’ 、Ｒ’およびＸは前記と同じ意
味を表わす。〕
で示される化合物をメチル化することにより製造するこ
とができる。(Production method A) Among the compounds of the present invention, the compound in which R1 is a methyl group has the general formula [wherein R', R', R' and X have the same meanings as above. ] It can be produced by methylating the compound shown below.
この反応は、通常、溶媒中で行なわれ、反応温度の範囲
は０−１００°０１反応時間の範囲は０．５〜１０時間
であり、反応に供される試剤の量は、一般式（Ｉ［）で
示される化合物１等量に対して、メチル化剤は１〜３等
量である。This reaction is usually carried out in a solvent, the reaction temperature ranges from 0 to 100°01, the reaction time ranges from 0.5 to 10 hours, and the amount of reagents used in the reaction is determined by the general formula (I The amount of the methylating agent is 1 to 3 equivalents per 1 equivalent of the compound represented by [).
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、ジエチルエーテル、ジ
イソプロピルエーテル、ジオキサン、テトラヒドロフラ
ン、ジエチレングリコールジメチルエーテル等のエーテ
ル類、ピリジン、トリエチルアミン、Ｎ、Ｎ−ジエチル
アニリン、トリブチルアミン、Ｎ−メチルモルホリン等
の第三級アミン、ホルムアミド、Ｎ、Ｎ−ジメチルホル
ムアミド、アセトアミド等の酸アミド、ジメチルスルホ
キシド、スルホラン等の硫黄化合物、あるいは、それら
の混合物かあげられる。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine, etc. , formamide, acid amides such as N,N-dimethylformamide and acetamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, and mixtures thereof.
メチル化剤としては、ヨウ化メチル、ジメチル硫酸等が
あげられる。Examples of the methylating agent include methyl iodide and dimethyl sulfate.
反応終了後、反応液を水にあけ、有機溶媒抽出および濃
縮等の通常の後処理を行ない、必要ならばクロマトグラ
フィー、蒸留、再結晶等の操作によって精製することに
より、目的の本発明化合物を得ることができる。After the reaction is complete, the reaction solution is poured into water and subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, distillation, recrystallization, etc. to obtain the desired compound of the present invention. Obtainable.
（製法Ｂ）
本発明化合物の中でＲ１がメチル基であり、Ｘがフッ素
原子である化合物は、一般式〔式中、Ｒ１およびＲ３は
前記と同じ意味を表わす。〕
で示される化合物と、一般式
％式％（）
〔式中、Ｚはハロゲン原子またはメタンスルホニルオキ
シ基またはｐ−トルエンスルホニルオキシ基を表わし、
Ｒ４は前記と同じ意味を表わす。〕
で示される化合物とを反応させることにより製造するこ
とができる。(Production method B) Among the compounds of the present invention, a compound in which R1 is a methyl group and X is a fluorine atom has the general formula [wherein R1 and R3 represent the same meanings as above]. ] A compound represented by the general formula % formula % () [wherein Z represents a halogen atom, a methanesulfonyloxy group or a p-toluenesulfonyloxy group,
R4 represents the same meaning as above. ] It can be produced by reacting with the compound shown below.
本反応は、通常溶媒中、塩基の存在下で行われ、反応温
度の範囲は０〜１００°Ｃであり、反応時間の範囲は０
．５〜ｌＯ時間であり、反応に供される試剤の量は、一
般式（Ｉ［［）で示される化合物１当量に対して、一般
式（ＩＶ）で示される化合物は１〜１．２当量、塩基は
１〜３当量である。This reaction is usually carried out in a solvent in the presence of a base, the reaction temperature ranges from 0 to 100°C, and the reaction time ranges from 0 to 100°C.
．． The reaction time is 5 to 10 hours, and the amount of reagents used in the reaction is 1 to 1.2 equivalents of the compound represented by general formula (IV) per 1 equivalent of the compound represented by general formula (I[[). , the base is 1 to 3 equivalents.
塩基としては、水酸化ナトリウム、水酸化カリウム、炭
酸ナトリウム、炭酸カリウム、水素化ナトリウム等の無
機塩基、ナトリウムメトキシド、ナトリウムエトキシド
等のアルカリ金属アルコキシド等があげられる。Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride, and alkali metal alkoxides such as sodium methoxide and sodium ethoxide.
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、クロロホルム、四塩化
炭素、ジクロロエタン、クロロベンゼン、ジクロロベン
ゼン等のハロゲン化炭化水素類、ジエチルエーテル、ジ
イソプロピルエーテル、ジオキサン、テトラヒドロフラ
ン、ジエチレングリコールジメチルエーテル等のエーテ
ル類、アセトン、メチルエチルケトン、メチルイソブチ
ルケトン、イソホロン、シクロヘキサノン等のケトン類
、蟻酸、酢酸、オレイン酸等の脂肪酸、メタノール、エ
タノール、イソプロパツール、ｔ−ブタノール、オクタ
ツール、シクロヘキサノール、メチルセロソルブ、ジエ
チレングリコール、グリセリン等のアルコール類、蟻酸
エチル、酢酸エチル、酢酸ブチル、炭酸ジエチル等のエ
ステル類、ニトロエタン、ニトロベンゼン等のニトロ化
物、アセトニトリル、イソブチロニトリル等のニトリル
類、ピリジン、トリエチルアミン、Ｎ。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, Ketones such as methyl isobutyl ketone, isophorone, and cyclohexanone, fatty acids such as formic acid, acetic acid, and oleic acid, alcohols such as methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl cellosolve, diethylene glycol, and glycerin. , esters such as ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate, nitrides such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N.
Ｎ−ジエチルアニリン、トリブチルアミン、Ｎ−メチル
モルホリン等の第三級アミン、ホルムアミド、Ｎ、Ｎ−
ジメチルホルムアミド、アセトアミド等の酸アミド、液
体アンモニア、水等あるいは、それらの混合物かあげら
れる。Tertiary amines such as N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N-
Examples include acid amides such as dimethylformamide and acetamide, liquid ammonia, water, and mixtures thereof.
反応終了後、反応液を水にあけ、生じた結晶を濾取、ま
たは有機溶媒抽出および濃縮等の通常の後処理を行い、
必要ならばクロマトグラフィー、蒸留、再結晶等の操作
によって精製することにより、目的の本発明化合物を得
ることができる。After the reaction is completed, the reaction solution is poured into water, and the resulting crystals are collected by filtration, or subjected to usual post-treatments such as organic solvent extraction and concentration.
If necessary, the desired compound of the present invention can be obtained by purification by operations such as chromatography, distillation, and recrystallization.
（製法Ｃ）
本発明化合物の中でＲ１がアミノ基である化合物は一般
式（ＩＩ）で示される化合物をアミノ化することによっ
て製造することができる。(Production method C) Among the compounds of the present invention, compounds in which R1 is an amino group can be produced by aminating a compound represented by general formula (II).
本反応は、通常溶媒中で行われ、反応温度の範囲は０〜
１００℃、反応時間の範囲は０．５〜１０時間であり、
反応に供される試剤の量は、一般式ＣＩ［］で示される
化合物１当量に対してアミノ化剤は１〜３当量である。This reaction is usually carried out in a solvent, and the reaction temperature ranges from 0 to
100°C, reaction time range is 0.5 to 10 hours,
The amount of the reagent used in the reaction is 1 to 3 equivalents of the aminating agent per 1 equivalent of the compound represented by the general formula CI[].
アミン化剤としては、例えば２．４−ジニトロフェノキ
シアミンかあげられる。Examples of the aminating agent include 2,4-dinitrophenoxyamine.
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、べ５ンゼン、トルエン
、キシレン等の芳香族炭化水素類、ジエチルエーテル、
ジイソプロピルエーテル、ジオキサン、テトラヒドロフ
ラン、ジエチレングリコールジメチルエーテル等のエー
テル類、ピリジン、トリエチルアミン、Ｎ、Ｎ−ジエチ
ルアニリン、トリブチルアミン、Ｎ−メチルモルホリン
等の第三級アミン、ホルムアミド、Ｎ、Ｎ−ジメチルホ
ルムアミド、アセトアミド等の酸アミド、ジメチルスル
ホキシド、スルホラン等の硫黄化合物あるいは、それら
の混合物があげられる。Examples of solvents include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, diethyl ether,
Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N-dimethylformamide, acetamide, etc. Examples include sulfur compounds such as acid amides, dimethyl sulfoxide, and sulfolane, or mixtures thereof.
反応終了後、反応液を水にあけ、有機溶媒抽出および濃
縮等の通常の後処理を行い、必要ならばクロマトグラフ
ィー、蒸留、再結晶等の操作によって精製することによ
り、目的の本発明化合物を得ることができる。After the reaction is complete, the reaction solution is poured into water and subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, distillation, recrystallization, etc. to obtain the desired compound of the present invention. Obtainable.
上記の製造法に準じて製造されるいくつかの本”発明化
合物を３４１表に示す。Table 341 shows some compounds of the present invention produced according to the above production method.
第１表
なお、本発明化合物に光学活性体か含まれることはもち
ろんである。Table 1 Note that it goes without saying that the compounds of the present invention include optically active compounds.
本発明化合物を製造する場合、原料化合物である一般式
ＣＩ［）で示される化合物は、以下の経路に従って製造
することができる。When producing the compound of the present invention, the compound represented by the general formula CI[), which is a starting compound, can be produced according to the following route.
（Ｉ［）
↑
に＋
〔式中、Ｒ″はアルキル基を表わし、Ｒ３Ｒ４およびＸ
は前記と同じ意味を表わす。〕
（製法Ｄ）（Ｖ）→（Ｉ［）
一般式［］Ｉ）で示される化合物は、一般式［Ｖ）で示
される化合物と一般式
％式％（
〔式中、Ｒ“はアルキル基を表わし、Ｒは前記と同じ意
味を表わす。〕
で示される化合物とを反応させることにより製造するこ
とができる。(I[) ↑ + [In the formula, R″ represents an alkyl group, R3R4 and
has the same meaning as above. ] (Production method D) (V)→(I[) The compound represented by the general formula []I) is a compound represented by the general formula [V] and the general formula and R has the same meaning as above.] It can be produced by reacting with the compound shown below.
本反応は、通常、溶媒中、脱水素剤の存在下で行い、反
応温度の範囲は０〜２００℃、反応時間の範囲は０．５
〜１０時間であり、反応に供される試剤の量は一般式（
Ｖ）で示される化合物１当量に対して一般式〔■〕で示
される化合物は１〜１．２当量、脱水素剤は１〜１．２
当量である。This reaction is usually carried out in a solvent in the presence of a dehydrogenating agent, with a reaction temperature range of 0 to 200°C and a reaction time range of 0.5°C.
~10 hours, and the amount of reagents used in the reaction is expressed by the general formula (
The compound represented by the general formula [■] is 1 to 1.2 equivalents per equivalent of the compound represented by V), and the dehydrogenating agent is 1 to 1.2 equivalents.
It is equivalent.
溶媒としては、ヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、ジエチルエーテル、ジ
イソプロピルエーテル、ジオキサン、テトラヒドロフラ
ン、ジエチレングリコールジメチルエーテル等のエーテ
ル類、ピリジン、トリエチルアミン、Ｎ、Ｎ−ジエチル
アニリン、トリブチルアミン、Ｎ−メチルモルホリン等
の第三級アミン、ホルムアミド、Ｎ、Ｎ−ジメチルホル
ムアミド、アセトアミド等の酸アミド、ジメチルスルホ
キシド、スルホラン等の硫黄化合物、あるいは、それら
の混合物かあげられる。As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine, etc. , formamide, acid amides such as N,N-dimethylformamide and acetamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, and mixtures thereof.
脱水素剤としては、炭酸ナトリウム、炭酸カリウム、水
素化ナトリウム等の無機塩基、ナトリウムメトキシド、
ナトリウムエトキシド等のアルカリ金属アルコキシド等
があげられる。As dehydrogenating agents, inorganic bases such as sodium carbonate, potassium carbonate, sodium hydride, sodium methoxide,
Examples include alkali metal alkoxides such as sodium ethoxide.
反応終了後、反応液を水にあけ、有機溶媒抽出および濃
縮等の通常の後処理を行い、必要ならば、クロマトグラ
フィー、蒸留、再結晶等の操作によって精製することに
より、目的の一般式（ＩＩ）で示される化合物を得るこ
とができる。また、上記反応で得られる一般式（Ｉｌｌ
）で示される化合物を単離することなくそのままメチル
化またはアミノ化することにより本発明化合物を得るこ
ともできる。After the reaction is complete, the reaction solution is poured into water and subjected to usual post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, distillation, recrystallization, etc. to obtain the desired general formula ( A compound represented by II) can be obtained. In addition, the general formula (Ill
) The compound of the present invention can also be obtained by methylating or aminating the compound as it is without isolating it.
（製法Ｅ） （ＶＩ）→（Ｖ）
一般式（Ｖ）で示される化合物は一般式ＣＶＩ）で示さ
れる化合物と一般式
般式
ＣＩＣＯＲ’ （■〕〔式中、Ｒ″
は前記と同じ意味を表わす。〕で示される化合物とを反
応させることによって製造することができる。(Production method E) (VI)→(V) The compound represented by the general formula (V) is combined with the compound represented by the general formula CVI) and the general formula CICOR' (■] [in the formula, R''
has the same meaning as above. ] It can be produced by reacting with the compound shown below.
この反応は、通常、無溶媒または溶媒中、脱ハロゲン化
水素剤の存在下で行い、反応温度の範囲は０〜１５０°
Ｃ１反応時間の範囲は０．５〜ｌＯ時間であり、反応に
供される試剤の量は一般式（ＶＩ）で示される化合物１
当量に対して一般式〔■〕で示される化合物は１〜１．
５当量であり、脱ハロゲン化水素剤は１〜】、５当量で
ある。This reaction is usually carried out without a solvent or in a solvent in the presence of a dehydrohalogenating agent, and the reaction temperature ranges from 0 to 150°.
The range of C1 reaction time is 0.5 to 10 hours, and the amount of reagent used in the reaction is the same as that of compound 1 represented by general formula (VI).
The compound represented by the general formula [■] is 1 to 1.
5 equivalents, and the dehydrohalogenating agent is 1 to 5 equivalents.
溶媒としては、ベンゼン、トルエン、キシレン等の芳香
族炭化水素類、クロロホルム、四塩化炭素等のハロゲン
化炭化水素類、ジエチルエーテル、ジオキサン等のエー
テル類があげられる。Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chloroform and carbon tetrachloride, and ethers such as diethyl ether and dioxane.
脱ハロゲン化水素剤としては、ピリジン、トリエチルア
ミン、Ｎ、Ｎ−ジエチルアニリン等の有機塩基、水酸化
ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カ
リウム、水素化ナトリウム等の無機塩基、ナトリウムメ
トキシド、ナトリウムエトキシド等のアルカリ金属アル
フキシト等があげられる。Examples of dehydrohalogenation agents include organic bases such as pyridine, triethylamine, and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride, sodium methoxide, and sodium hydroxide. Examples include alkali metal alkoxides such as ethoxides.
反応終了後、反応液を水にあけ、有機溶媒抽出および濃
縮等の通常の後処理を行い、必要ならば、クロマトグラ
フィー、蒸留、再結品等ｎ作によって精製することによ
り、目的の一般式（Ｖ）で示される化合物を得ることが
できる。After the reaction is complete, the reaction solution is poured into water and subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, distillation, reconcentration, etc. to obtain the desired general formula. A compound represented by (V) can be obtained.
また、本発明化合物の原料化合物である一般式（ＩＩ［
］で示される化合物は以下の経路に従って製造すること
ができる。In addition, general formula (II[
] The compound represented by can be produced according to the following route.
ＣＩ［］
↑
〔式中、Ｒ１はアルキル基を表わし、Ｒ１およびＲ１は
前記と同じ意味を表わす。〕（製法Ｆ）（ＩＸ）→（Ｉ
［）
一般式（Ｉ［）で示される化合物は一般式（ＩＸ）で示
される化合物を還元すると同時に環化させることにより
製造することができる。CI[] ↑ [In the formula, R1 represents an alkyl group, and R1 and R1 have the same meaning as above. ] (Production method F) (IX) → (I
[) The compound represented by the general formula (I[) can be produced by reducing and simultaneously cyclizing the compound represented by the general formula (IX).
還元方法としては鉄還元または接触還元かあげられる。Examples of the reduction method include iron reduction or catalytic reduction.
鉄還元を行う場合、本反応は、通常溶媒中、少量の酸の
存在下で行われ、一般式（ＩＸ）で示される化合物１当
量に対して２５〜１０当量の鉄粉を用いる。反応温度の
範囲は５０〜２００℃、反応時間の範囲は０．５〜１０
時間である。溶媒としては、例えば、トルエン、１．２
−ジクロロエタン、メチルイソブチルケトン、酢酸、水
あるいはそれらの混合物があげられ、酸としては、例え
ば、酢酸、塩酸があげられる。When carrying out iron reduction, this reaction is usually carried out in a solvent in the presence of a small amount of acid, and 25 to 10 equivalents of iron powder are used per 1 equivalent of the compound represented by the general formula (IX). The reaction temperature range is 50-200℃, the reaction time range is 0.5-10
It's time. As a solvent, for example, toluene, 1.2
-dichloroethane, methyl isobutyl ketone, acetic acid, water or a mixture thereof; examples of acids include acetic acid and hydrochloric acid.
接触還元を行う場合、本反応はメタノール、エタノール
等の溶媒中、触媒量のパラジウム炭素の存在下で行われ
、室温で０．５〜２０時間で終了する。When carrying out catalytic reduction, this reaction is carried out in a solvent such as methanol or ethanol in the presence of a catalytic amount of palladium on carbon, and is completed in 0.5 to 20 hours at room temperature.
これらの反応が終了した後、反応液を濾過し、濾液に水
を加え、有機溶媒抽出および濃縮等の通常の後処理を行
い、必要ならば再結晶、カラムクロマトグラフィー等の
精製操作を行うことにより一般式（ＩＩ［）で示される
化合物を得ることができる。After these reactions are completed, the reaction solution is filtered, water is added to the filtrate, and conventional post-treatments such as organic solvent extraction and concentration are performed, and if necessary, purification operations such as recrystallization and column chromatography are performed. A compound represented by the general formula (II[) can be obtained.
（製法Ｇ）（Ｘ）→（ＩＸ）
一般式（ＩＸ）で示される化合物は一般式ＣＸ）で示さ
れる化合物と一般式
％式％（［）
〔式中、Ｒ３およびＲ＠は前記と同し意味を表わす。〕
で示される化合物とを反応させることにより製造するこ
とができる。(Production method G) (X) → (IX) The compound represented by the general formula (IX) is the compound represented by the general formula CX) and the general formula % formula % ([) [wherein, R3 and R@ are the same as above] and express the meaning. ] It can be produced by reacting with the compound shown below.
本反応は、通常塩基の存在下、溶媒中で行われ、反応温
度の範囲は２５〜２００°Ｃ１反応時間の範囲は０．５
〜１０時間であり、反応に供せられる試剤の量は一般式
（Ｘ）で示される化合物１当量に対して一般式（Ｘｌ＋
）で示される化合物はｌ −１，２当量であり、塩基は
１〜４当量である。This reaction is usually carried out in a solvent in the presence of a base, with a reaction temperature ranging from 25 to 200°C and a reaction time of 0.5°C.
~10 hours, and the amount of reagent used in the reaction is based on the general formula (Xl+) per equivalent of the compound represented by the general formula (X).
) The compound represented by 1-1,2 equivalents, and the base has 1 to 4 equivalents.
溶媒としてはトルエン、キシレン等の芳香族炭化水素類
、ジクロロメタン、１．２−ジクロロエタン等のハロゲ
ン化炭化水素類、テトラヒドロフラン、ジオキサン等の
エーテル類等があげられ、塩基としてはフッ化カリウム
、炭酸カリウム、水素化ナトリウム等の無機塩基等があ
げられる。Examples of solvents include aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, and ethers such as tetrahydrofuran and dioxane. Examples of bases include potassium fluoride and potassium carbonate. , inorganic bases such as sodium hydride, etc.
反応終了後、反応液を水にあけ、有機溶媒抽出および濃
縮等の通常の後処理を行い、必要ならばクロマトグラフ
ィー、再結晶等の操作を行って精製することにより一般
式（ＩＸ）で示される化合物を得ることができる。After the reaction is complete, the reaction solution is poured into water and subjected to usual post-treatments such as organic solvent extraction and concentration, and if necessary, purified by chromatography, recrystallization, etc. to obtain the product represented by general formula (IX). can be obtained.
（製法Ｈ） （ＸＩ）−＋（Ｘ）
一般式〔Ｘ〕で示される化合物は一般式（ＸＩ）で示さ
れる化合物を濃硫酸中、硝酸を用いてニトロ化すること
により製造することができる。(Production method H) (XI)-+(X) The compound represented by the general formula [X] can be produced by nitrating the compound represented by the general formula (XI) using nitric acid in concentrated sulfuric acid. .
本反応において反応温度の範囲は０〜３゜°Ｃ１反応時
間の範囲は０．３〜３時間であり、反応に供される硝酸
の量は一般式〔ｘ１〕で示される化合物１当量に対して
１−１．５当量である。反応終了後は通常の後処理を行
い、般式〔Ｘ〕で示される化合物を得ることができる。In this reaction, the reaction temperature range is 0 to 3°C, the reaction time is 0.3 to 3 hours, and the amount of nitric acid used for the reaction is per equivalent of the compound represented by the general formula [x1]. It is 1-1.5 equivalents. After the reaction is completed, the compound represented by the general formula [X] can be obtained by carrying out a usual post-treatment.
本発明化合物は、畑地の茎葉処理および土壌処理におい
て問題となる種々の雑草、例えば、ソバカズラ、サナエ
タデ、スベリヒエ、ハコベ、シロザ、アオゲイトウ、ダ
イコン、ノハラガラシ、ナズナ、アメリカッノクサネム
、エビスグサ、イチビ、アメリカキンゴジカ、フィール
ドパンジー、ヤエムグラ、アメリカアサガオ、マルバア
サガオ、セイヨウヒルガオ、ヒメオドリコソウ、ホトケ
ノザ、シロバナチョウセンアサガオ、イヌホオズキ、オ
オイヌノフグリ、オナモミ、ヒマワリ、イヌカミツレ、
コーンマリーゴールド等の広葉雑草、ヒエ、イヌビエ、
エノコログサ、メヒシバ、スズメノカタビラ、ノスズメ
ノテッポウ、エンバク、カラスムギ、セイバンモロコシ
、シバムギ、ウマノチャヒキ、ギョウギシバ、アキノエ
ノコログサ等のイネ科雑草およびツユクサ等のツユクサ
科雑草、フゴメガヤツリ、ハマズゲ等のカヤツリグサ科
雑草等に対して除草効力を有し、しかも本発明化合物は
、トウモロコシ、コムギ、オオムギ、イネ、ダイブ、ワ
タ等の主要作物に対して問題となるような薬害を示さな
い。The compound of the present invention can be used for various weeds that are problematic in the treatment of foliage and soil in upland areas, such as freckle grass, Japanese knotweed, purslane, chickweed, whiteweed, Japanese radish, daikon radish, Japanese radish, shepherd's purse, American staghorn, Ebisu spp. Golden deer, field pansies, Japanese violets, morning glories, common morning glories, European bindweed, Japanese odorifera, hotokenoza, white-breasted morning glories, Japanese Physalis, Japanese Physalis, Japanese Physalis, Japanese fir tree, Sunflower, Japanese Convolvulus,
Broad-leaved weeds such as corn marigolds, barnyard grass, and barnyard grass,
Herbicidal efficacy against grass family weeds such as foxtail grass, hawkweed, sycamore, grasshopper, oat, oat, seiban sorghum, grass barley, japanese grass, japonica, and cypress family weeds, as well as cyperaceae weeds such as dayflower, dayflower, and cyperaceae weeds such as cyperus spp. Furthermore, the compounds of the present invention do not cause any problematic phytotoxicity to major crops such as corn, wheat, barley, rice, diver, and cotton.
また、本発明化合物は、水田の湛水処理において問題と
なる種々の雑草、例えば、タイヌビエ等のイネ科雑草、
アゼナ、キカシグサ、ミゾハコベ等の広葉雑草、タマガ
ヤツリ、ホタルイ、マツバイ、ミズガヤツリ等のカヤツ
リグサ科雑草、コナギ、ウリカワ等に対して除草効力を
有し、しかもイネに対しては問題となるような薬害を示
さない。In addition, the compound of the present invention can be applied to various weeds that are problematic in the flooding treatment of rice fields, such as grass weeds such as Japanese millet grass,
It has a herbicidal effect on broad-leaved weeds such as azalea, Japanese chickweed, and Japanese chickweed, on cyperaceous weeds such as Japanese cypress, Japanese cypress, Japanese cypress, and Japanese cypress, as well as on Japanese cypress, Japanese cypress, and other plants, and does not cause any harmful effects on rice. do not have.
本発明化合物を除草剤の有効成分として用いる場合は、
通常、固体担体、液体担体、界面活性剤その他の製剤用
補助剤と混合して、乳剤、水和剤、懸濁剤、粒剤、顆粒
水和剤等に製剤する。これらの製剤には、有効成分とし
て本発明化合物を重量比で０．０２〜８０％、好ましく
は０．０５〜７０％含有する。When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, wettable powders, and the like. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.02 to 80%, preferably 0.05 to 70%.
固体担体としては、カオリンクレー、アッタバルジャイ
トクレー、ベントナイト、酸性白土、パイロフィライト
、タルク、珪藻土、方解石、クルミ殻粉、尿素、硫酸ア
ンモニウム、合成含水酸化珪素等の微粉末あるいは粒状
物かあげられ、液体担体としては、キンレン、メチルナ
フタレン等の芳香族炭化水素類、イソプロパツール、エ
チレングリコール、セロソルブ等のアルコール類、アセ
トン、シクロヘキサノン、イソホロン等のケトン類、大
豆油、綿実油等の植物油、ジメチルスルホキシド、Ｎ、
Ｎ−ジメチルホルムアミド、アセトニトリル、水等があ
げられる。Examples of solid carriers include fine powders or granules such as kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as quinolene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl sulfoxide, N,
Examples include N-dimethylformamide, acetonitrile, water and the like.
乳化、分散、湿展等のために用いられる界面活性剤とし
ては、アルキル硫酸エステル塩、アルキルスルホン酸塩
、アルキルアリールスルホン酸塩、ジアルキルスルホコ
ハク酸塩、ポリオキシエチレンアルキルアリールエーテ
ルリン酸エステル塩等の陰イオン界面活性剤、ポリオキ
シエチレンアルキルエーテル、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ポリオキシ
プロピレンブロックコボリマー、ソルビタン脂肪酸エス
テル、ポリオキシエチレンソルビタン脂肪酸エステル等
の非イオン界面活性剤等があげられる。Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc. It will be done.
その他の製剤用補助剤としては、リグニンスルホン酸塩
、アルギン酸塩、ポリビニルアルコール、アラビアガム
、ＣＭＣ（カルボキシメチルセルロース）、ＰＡＰ（酸
性リン酸イソプロピル）等があげられる。Other formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like.
本発明化合物は、通常製剤化して雑草の出芽前または出
芽後に土壌処理、茎葉処理または湛水処理する。土壌処
理には、土壌表面処理、土壌混和処理等があり、茎葉処
理には、植物体の上方からの処理のほか、作物に付着し
ないよう雑草に限って処理する局部処理等がある。The compound of the present invention is usually formulated and treated with soil, foliage, or flooding before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops.
また、他の除草剤と混合して用いることにより、除草効
力の増強を期待することができる。さらに、殺虫剤、殺
ダニ剤、殺線虫剤、殺菌剤、植物生長調節剤、肥料、土
壌改良剤等と混合して札いることもできる。Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be mixed with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地、森林あるいは非農耕地の有効成分として用いる
ことができる。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in lawns, forests or non-agricultural lands.
本発明化合物を除草剤の有効成分として用いる場合、そ
の処理量は気象条件、製剤形態、処理時期、方法、場所
、対象井草、対、象作物等によっても異なるが、通常１
アールあたり０．０１〜８０ｇ、好ましくは、０．０２
〜４０ｇであり、乳剤、水和剤、懸濁剤等は、通常その
所定量を１アールあたり１リツトル〜１０リツトルの（
必要ならば展着剤等の補助剤を添加した）水で希釈して
処理し、粒剤等は、通常なんら希釈することなくそのま
ま処理する。When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target grass, target crops, etc., but usually 1.
0.01 to 80g per are, preferably 0.02
~40g, and emulsions, wettable powders, suspending agents, etc. are usually used in a prescribed amount of 1~10 liters per are.
If necessary, it is diluted with water (to which an auxiliary agent such as a spreading agent is added), and granules and the like are usually treated as they are without any dilution.
展着剤としては、前記の界面活性剤のほか、ポリオキシ
エチレン樹脂酸（エステル）、すゲニンスルホン酸塩、
アビエチン酸塩、ジナフチルメタンジスルホン酸塩、パ
ラフィン等があげられる。In addition to the above-mentioned surfactants, the spreading agents include polyoxyethylene resin acid (ester), sugenine sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, and paraffin.
〈発明の効果〉
本発明化合物は、畑地の土壌処理および茎葉処理、さら
に水田の湛水処理にお−て問題となる種々の雑草に対し
て優れた除草効力を有し、主要作物と雑草間に優れた選
択性を示すことから除草剤の有効成分として種々の用途
に用いることができる。<Effects of the Invention> The compound of the present invention has excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in flooding treatment of rice fields, and has an excellent herbicidal effect on various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in waterlogging treatment of paddy fields. Since it exhibits excellent selectivity for herbicides, it can be used in a variety of applications as an active ingredient in herbicides.
〈実施例〉
以下、本発明を製造例、製剤例および試験例により、さ
らに詳しく説明するが、本発明はこれらの実施例に限定
されるものではない。<Examples> The present invention will be explained in more detail below using production examples, formulation examples, and test examples, but the present invention is not limited to these examples.
まず、製造例を示す。First, a manufacturing example will be shown.
製造例１
１−〔７−フルオロ−４−プロパルギル−２８−１，４
−ベンゾオキサジン−３（４Ｈ）−オン−６−イル）−
４−トリフルオロメチル−１，２，３，６−テトラヒド
ロピリミジン−２，６−シオン２．０ｇをジメチルホル
ムアミド１０ｇに溶解し、これにヨウ化メチル０．５ｇ
および炭酸カリウム１．６ ｇを加えて８０〜】００°
Ｃ１３時間加熱した。反応後反応液を水にあけ、生じた
結晶を濾取、水洗乾燥した後、カラムクロマトグラフィ
ーで精製して白色結晶の本発明化合物（５） ］、 Ｏ
ｇを得た。Production example 1 1-[7-fluoro-4-propargyl-28-1,4
-Benzoxazin-3(4H)-one-6-yl)-
Dissolve 2.0 g of 4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-sion in 10 g of dimethylformamide, and add 0.5 g of methyl iodide to this.
and 1.6 g of potassium carbonate to 80~]00°
C Heated for 13 hours. After the reaction, the reaction solution was poured into water, and the resulting crystals were collected by filtration, washed with water, dried, and purified by column chromatography to obtain the compound (5) of the present invention as white crystals.
I got g.
融点 ８６〜８８°Ｃ
’Ｈ−ＮＭＲδ（ｐｐｍ）
ＣＣＤＣＩ ｚ 、６０ＭＨｚ ）
２．２８ ｃｔ、Ｊ＝２．５Ｈ！、ＩＨ）３．５５ （
ｓ、３Ｈ）
４．６３ （ｄ、Ｊ＝２．５Ｈ工、２Ｈ）４．６６ （
ｓ、２Ｈ）
６．３３ （ｓ、ＩＨ）
６．９０ （ｄ、Ｊ＝Ｉ ＩＨｚ、ＩＨ）６．９８ （
ｄ、Ｊ＝６Ｈｚ、ＩＨ）
製造例２
７−フルオロ−６−メドキシカルボニルアミノー４−プ
ロパルギル−２８−１，４−ベンゾオキサジン−３（４
Ｈ）−オン１．４ ｇおよび３−アミノ−４，４，４−
）リフルオロクロトン酸メチル０．９２ｇをジメチルホ
ルムアミド５ｇに溶解し、６０％水素化ナトリウム０．
２ｇを加え水冷下３０分攪拌した。３０分後昇温し、３
時間還流した。放冷後、ヨウ化メチル１ｇを加え４０℃
で３０分攪拌した。Melting point 86-88°C'H-NMRδ (ppm) CCDCIz, 60MHz) 2.28 ct, J=2.5H! , IH) 3.55 (
s, 3H) 4.63 (d, J=2.5H, 2H) 4.66 (
s, 2H) 6.33 (s, IH) 6.90 (d, J=I IHz, IH) 6.98 (
d, J=6Hz, IH) Production Example 2 7-Fluoro-6-medoxycarbonylamino-4-propargyl-28-1,4-benzoxazine-3(4
H)-one 1.4 g and 3-amino-4,4,4-
) Dissolve 0.92 g of methyl fluorocrotonate in 5 g of dimethylformamide and add 0.92 g of methyl fluorocrotonate to 0.92 g of 60% sodium hydride.
2 g was added and stirred for 30 minutes under water cooling. After 30 minutes, raise the temperature and
Refluxed for an hour. After cooling, add 1 g of methyl iodide to 40°C.
The mixture was stirred for 30 minutes.
反応液に水を加え、エーテルで抽出、濃縮し、シリカゲ
ルカラムクロマトグラフィーで精製して本発明化合物＋
５） ０．３ ｇを得た。Water was added to the reaction solution, extracted with ether, concentrated, and purified by silica gel column chromatography to obtain the compound of the present invention +
5) 0.3 g was obtained.
製造例３
１−〔７−フルオロ−２Ｈ−１，４−ベンゾオキサジン
−３（４Ｈ）−オン−６−イル〕−３−メチル−４−ト
リフルオロメチル−１，２，３，６−テトラヒドロビリ
ミジン−２，６−ジオン Ｚ３ｇをジメチルホルムアミ
ド１０ｇに溶解し、これにクロロメチルメチルエーテル
１ｇおよび炭酸カリウム１．７ｇを加え、４０〜５０℃
で３０分加熱した。Production Example 3 1-[7-fluoro-2H-1,4-benzoxazin-3(4H)-one-6-yl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydro 3 g of pyrimidine-2,6-dione Z was dissolved in 10 g of dimethylformamide, 1 g of chloromethyl methyl ether and 1.7 g of potassium carbonate were added thereto, and the mixture was heated at 40-50°C.
It was heated for 30 minutes.
反応終了後、反応液を水にあけ、酢酸エチル３０−で抽
出し、水洗、乾燥、濃縮した。粗生成物をカラムクロマ
トグラフィーで精製して、本発明化合物（８） １．８
ｇを得た。After the reaction was completed, the reaction solution was poured into water, extracted with 30% of ethyl acetate, washed with water, dried, and concentrated. The crude product was purified by column chromatography to obtain the compound of the present invention (8) 1.8
I got g.
製造例４
７−フルオロ−６−メドキシカルポニルアミノー４−プ
ロパルギル−２Ｈ−１，４−ベンゾオキサジン−３（４
Ｈ）−オン１．４ ｇおよび３−アミノ−４，４，４−
トリフルオロクロトン酸エチル０．９２ ｇをジメチル
ホルムアミド５ｇに溶解し、これに水素化ナトリウム０
．２ｇを加え、水冷下３０分間攪拌し、その後３時間加
熱還流した。放冷後、２，４−ジニトロフェノキシアミ
ン１．２ ｇを加え、４０℃で３時間攪拌した。反応終
了後、反応液に水を加え、酢酸エチルで抽出し、濃縮し
た。Production Example 4 7-Fluoro-6-medoxycarponylamino-4-propargyl-2H-1,4-benzoxazine-3(4
H)-one 1.4 g and 3-amino-4,4,4-
Dissolve 0.92 g of ethyl trifluorocrotonate in 5 g of dimethylformamide, and add 0.0 g of sodium hydride to this solution.
．． 2 g was added, stirred for 30 minutes under water cooling, and then heated under reflux for 3 hours. After cooling, 1.2 g of 2,4-dinitrophenoxyamine was added, and the mixture was stirred at 40°C for 3 hours. After the reaction was completed, water was added to the reaction solution, extracted with ethyl acetate, and concentrated.
粗生成物をシリカゲルクロマトグラフィーで精製して本
発明化合物Ｑ４０．２ ｇを得た。The crude product was purified by silica gel chromatography to obtain 40.2 g of the present compound Q.
次に、この製造法に準じて製造された本発明化合物のい
くつかを１７Ｊ２表に示す。Next, some of the compounds of the present invention produced according to this production method are shown in Table 17J2.
次に、本発明化合物の原料化合物の製造例を示す。Next, a production example of a raw material compound for the compound of the present invention will be shown.
製造例５（化合物〔■〕）
７−フルオロ−６−メドキシカルボニルアミノー４−プ
ロパルギル−２Ｈ−１，４−ベンゾオキサジン−３（４
Ｈ）−オン１．４ｇおよび３−アミノ−４，４，４−１
−リフルオロクロトン酸エチルをジメチルホルムアミド
５ｇに溶解し、そこに水素化ナトリウム０．２ｇを加え
、水冷下３０分間攪拌し、その後３時間加熱還流した。Production Example 5 (Compound [■]) 7-Fluoro-6-medoxycarbonylamino-4-propargyl-2H-1,4-benzoxazine-3(4
H)-one 1.4 g and 3-amino-4,4,4-1
- Ethyl fluorocrotonate was dissolved in 5 g of dimethylformamide, 0.2 g of sodium hydride was added thereto, stirred for 30 minutes under water cooling, and then heated under reflux for 3 hours.
放冷後、反応液を水にあけ、酢酸エチルで抽出し、濃縮
した。粗生成物をカラムクロマトグラフィーで精製し、
ｌ−〔７−フルオロ−４−プロパルギル−２Ｈ−１，４
−ベンゾオキサジン−３（４Ｈ）−オン−６−イル）
−４−１−リフルオロメチル−１，２，３，６−チトラ
ヒドロピリミジンー２．６−ジオン０，２ｇを得た。After cooling, the reaction solution was poured into water, extracted with ethyl acetate, and concentrated. The crude product was purified by column chromatography,
l-[7-fluoro-4-propargyl-2H-1,4
-benzoxazin-3(4H)-one-6-yl)
0.2 g of -4-1-lifluoromethyl-1,2,3,6-titrahydropyrimidine-2,6-dione was obtained.
第３表
製造例６（化合物〔■〕）
６−アミツーツーフルオロ−４−プロパルギル−２Ｈ−
１，４−ベンゾオキサジン−３（４Ｈ）−オン２．１ｇ
、Ｎ、Ｎ−ジエチルアニリン１．５ｇおよびクロロギ酸
メチル１．０ ｇを１．２−ジクロロエタンＩＯｇに溶
解し、３時間還流した。放冷後反応液を水洗し、有機層
を濃縮した。粗生成物をメタノールで洗浄し、７−フル
オロ−６−メドキシカルボニルアミノー４−プロパルギ
ル−２８−１，４−ベンゾオキサジン−３（４Ｈ）−オ
ン２．０ｇを得た。Table 3 Production Example 6 (Compound [■]) 6-amitwofluoro-4-propargyl-2H-
2.1 g of 1,4-benzoxazin-3(4H)-one
, N,N-diethylaniline (1.5 g) and methyl chloroformate (1.0 g) were dissolved in IOg of 1,2-dichloroethane and refluxed for 3 hours. After cooling, the reaction solution was washed with water, and the organic layer was concentrated. The crude product was washed with methanol to obtain 2.0 g of 7-fluoro-6-medoxycarbonylamino-4-propargyl-28-1,4-benzoxazin-3(4H)-one.
次に、上記の製造例に準じて製造された一般式〔■〕で
示される化合物のいくつかを第４表に示す。Next, Table 4 shows some of the compounds represented by the general formula [■] that were produced according to the above production examples.
第４表
製造例７（化合物〔■〕）
１−（２−フルオロ−４−ブチルオキシカルボニルメト
キシ−５−二トロフェニル−３−メチル−４−トリフル
オロメチル−１，２゜３．６−テトラヒドロビリミジン
−２，６ジオン］Ｏｇ、水３ｇおよび鉄粉８ｇを酢酸５
０ｇに懸濁させ、３時間還流した。反応終了後、反応液
をセライト濾過し、濾液に水を加え、これを酢酸エチル
で抽出した。有機層を濃縮し、残渣をカラムクロマトグ
ラフィーで精製し、１−〔７−フルオロ−２Ｈ−１゜４
−ベンゾオキサジン−３（４Ｈ）−オン−６−イル〕−
３−メチル−４−トリフルオロメチル−１，２，３，６
−テトラヒドロピリミジン−２，６−ジオン８．Ｏｇを
得た。Table 4 Production Example 7 (Compound [■]) 1-(2-Fluoro-4-butyloxycarbonylmethoxy-5-nitrophenyl-3-methyl-4-trifluoromethyl-1,2°3.6- Tetrahydrobyrimidine-2,6dione]Og, 3g of water and 8g of iron powder were mixed with 5g of acetic acid.
The suspension was suspended at 0 g and refluxed for 3 hours. After the reaction was completed, the reaction solution was filtered through Celite, water was added to the filtrate, and this was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by column chromatography to obtain 1-[7-fluoro-2H-1゜4
-Benzoxazin-3(4H)-one-6-yl]-
3-methyl-4-trifluoromethyl-1,2,3,6
-Tetrahydropyrimidine-2,6-dione8. Obtained Og.
融点 ２２４−２２５℃
製造例８（化合物〔■〕）
１−（２，４−ジフルオロ−５−二トロフェニル）−３
−メチル−４−トリフルオロメチル−１，２，３，６−
テトラヒドロビリミジン−２，６−ジオン１０
酸ブチル５ｇおよびフッ化カリウム１０ｇをジオキサン
３０ｇに懸濁させ、４時間還流した。反応終了後、反応
液を水にあけ、酢酸エチルで抽出し、有機層を濃縮した
。残渣をシリカゲルカラムクロマトグラフィーで精製し
、１−（２−フルオロ−４−ブチルオキシカルボニルメ
トキシ−５−二トロフェニル）−３−メチル−４−トリ
フルオロメチル−１，２。Melting point 224-225°C Production example 8 (compound [■]) 1-(2,4-difluoro-5-nitrophenyl)-3
-Methyl-4-trifluoromethyl-1,2,3,6-
Tetrahydrobyrimidine-2,6-dione 10 5 g of butyl fluoride and 10 g of potassium fluoride were suspended in 30 g of dioxane and refluxed for 4 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was concentrated. The residue was purified by silica gel column chromatography to give 1-(2-fluoro-4-butyloxycarbonylmethoxy-5-nitrophenyl)-3-methyl-4-trifluoromethyl-1,2.
３、６−テトラヒドロビリミジン−２，６−ジオン１
１． Ｏ ｇを得た。3,6-tetrahydrobyrimidine-2,6-dione 1
1. Og was obtained.
融点 １１０−１１３℃
製造例９（化合物〔Ｘ〕）
１−（２．４−ジフルオロフェニル）−３−メチル−４
−トリフルオロメチル−１，２。Melting point 110-113°C Production example 9 (compound [X]) 1-(2.4-difluorophenyl)-3-methyl-4
-trifluoromethyl-1,2.
３、６−テトラヒドロピリミジン−２，６−シオン３
０． ６ ｇを濃硫酸１００ｇに溶解し、５℃に冷却し
た。そこに、１０℃以下で６１％硝酸を滴下し、３時間
攪拌した。反応終了後反応液を水にあけ、生じた結晶を
濾取、乾燥して１−（２．４−ジフルオロ−５−ニトロ
フェニル）−３−メチル−４−トリフルオロメチル−１
，２，３，６−チトラヒトロビリミジンー２．６−シオ
ン３３ｇを得た。3,6-tetrahydropyrimidine-2,6-sion 3
0. 6 g was dissolved in 100 g of concentrated sulfuric acid and cooled to 5°C. Thereto, 61% nitric acid was added dropwise at 10° C. or below, and the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was poured into water, and the resulting crystals were collected by filtration and dried to give 1-(2,4-difluoro-5-nitrophenyl)-3-methyl-4-trifluoromethyl-1.
, 33 g of 2,3,6-titrahydrobyrimidine-2,6-sion were obtained.
融点 １５６−１５７℃
次に、製剤例を示す。なお、本発明化合物は第２表の化
合物番号を示す。部は重量部である。Melting point: 156-157°C Next, formulation examples are shown. In addition, the compounds of the present invention show the compound numbers in Table 2. Parts are parts by weight.
製剤例１
本発明化合物（１）、（２）、（４）〜α２．０４〜α
Ｇ各々５０部、リグニンスルホン酸カルシウム３部、ラ
ウリル硫酸ナトリウム２部および合成含水酸化珪素４５
部をよく粉砕混合して水和剤を得る。Formulation Example 1 Compounds of the present invention (1), (2), (4) ~α2.04~α
50 parts each of G, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrated silicon oxide.
Thoroughly grind and mix the two parts to obtain a wettable powder.
製剤例２
本発明化合物（１）〜ＯＧ各々各部５部リオキシエチレ
ンスチリルフェニルエーテル１４部、ドデシルベンゼン
スルホン酸カルシウム６部、キシレン２５部およびシク
ロへキサノン５０部をよく混合して乳剤を得る。Formulation Example 2 5 parts each of compounds (1) to OG of the present invention, 14 parts of lyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 25 parts of xylene and 50 parts of cyclohexanone are thoroughly mixed to obtain an emulsion.
製剤例３
本発明化合物（１）〜０Ｇ各々２部、合成含水酸化珪素
１部、リグニンスルホン酸カルシウム２部、ベントナイ
ト３０部およびカオリンクレー６５部をよく粉砕混合し
、水を加えてよく練り合わせた後、造粒乾燥して粒剤を
得る。Formulation Example 3 2 parts each of the compounds of the present invention (1) to 0G, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, and water was added and kneaded well. Thereafter, the mixture is granulated and dried to obtain granules.
製剤例４
本発明化合物（１）、（２）、（４）〜Ｏ２、Ｑ４）
〜ａｅ各々２５部、ポリオキシエチレンソルビタンモノ
オレエート３部、ＣＭＣ３部、水６９部を混合し、粒度
か５ミクロン以下になるまで湿式粉砕して懸濁剤を得る
。Formulation Example 4 Compounds of the present invention (1), (2), (4) - O2, Q4)
25 parts of each of ~ae, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water are mixed and wet-pulverized until the particle size is 5 microns or less to obtain a suspension.
製剤例５
本発明化合物（１１〜αＧ各々０．０５部、合成含水酸
化珪素１部、リグニンスルホン酸カルシウム２部、ベン
トナイト３０部およびカオリンクレー６６．９５部をよ
く粉砕混合し、水を加えてよく練り合わせた後、造粒乾
燥して粒剤を得る。Formulation Example 5 Compounds of the present invention (0.05 parts each of 11 to αG, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite and 66.95 parts of kaolin clay were thoroughly ground and mixed, and water was added. After thoroughly kneading, the mixture is granulated and dried to obtain granules.
次に試験例を示す。なお、本発明化合物は第２表の化合
物番号で示し、比較対照に用いた化合物は第５表の化合
物記号で示す。Next, a test example is shown. The compounds of the present invention are indicated by the compound numbers in Table 2, and the compounds used for comparison are indicated by the compound symbols in Table 5.
第５表
バク、マルバアサガオ、イチビを播種し、覆土した。製
剤例２に準して供試化合物を乳剤にし、その所定量を１
アールあたり１０す、ットル相当の水で希釈し、小型噴
霧器で土壌表面に処理した。処理後２０日間温室内で育
成し、除草効力を調査した。その結果を第６表に示す。Table 5: Sowing tapir, morning glory, and trumpet and covering with soil. The test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount was
It was diluted with 10 liters of water per area and applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 6.
第６表
また、除草効力および薬害の評価は、調査時の供試植物
（雑草および作物）の８芽および生育の状態が無処理の
それと比較して全くないしほとんど違いが無いものを「
０」とし、供試植物が完全枯死または出芽もしくは生育
が完全に抑制されているものを「５」として、Ｏ〜５の
６段階に区分し、０．Ｉ、２．３．４．５で示す。Table 6 In addition, the evaluation of herbicidal efficacy and phytotoxicity is based on the condition of the test plants (weeds and crops) at the time of the survey.
The test plants are classified into 6 stages from 0 to 5, with the test plants being completely withered or whose budding or growth is completely suppressed as "5". I, 2.3.4.5.
試験例１
直径１０ｃｍ、深さ１０ｃｍの円筒型プラスチックポッ
トに畑地土壌を詰め、ヒエ、エン試験例２
直径１０ａｎ、深さ１０ａｎの円筒型プラスチックポッ
トに畑地土壌を詰め、ヒエ、エンバク、ブイコン、イチ
ビおよびマルバアサガオを播種し、温室内で１０Ｅｒ間
育成した。その後、製剤例２に準じて供試化合物を乳剤
にし、その所定量を１アールあたり１０リツトル相当の
展着剤を含む水で希釈し、小量噴霧器で植物体の上方か
ら茎葉処理した。処理後２０日間温室内で育成し、除草
効力を調査した。その結果を第７表に示す。Test Example 1 A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with field soil, and the fields were filled with field soil. and Maruba morning glory were sown and grown in a greenhouse for 10 Er. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small-volume sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 7.
第７表
し、その所定量を５ミリリツトルの水で希釈し、水面に
処理した。処理後、２０日間温室内で育成し、除草効力
および薬害を調査した。A predetermined amount of Table 7 was diluted with 5 milliliters of water and applied to the water surface. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy and phytotoxicity were investigated.
その結果を第８表に示す。The results are shown in Table 8.
第８表
試験例３
直径８ａｎ、深さ１２ａｎの円筒型プラスチックポット
に水田土壌を詰め、タイヌビエ、広葉雑草（アゼナ、キ
カシグサ、ミゾハコベ）の種子を１〜２ａ１１の深さに
混ぜ込んだ。湛水して水田状態にした後３葉期のイネを
移植し、温室内で育成した。６日後（各雑草の発生初期
）に製剤例２に準じて供試化合物を乳剤に試験例４
面積３３Ｘ２３ｅＩＩＩｒ１深さ１ｌａｎのバットに畑
地土壌を詰め、イネ、トウモロコシ、ダイブ、マルバア
サガオ、イチビ、イヌホオズキ、セイバンモロコシ、エ
ノコログサを播種し、１〜２ａｎの厚さに覆土した。製
剤例２に準じて供試化合物を乳剤にし、その所定量を１
アールあたりｌＯリットル相当の水で希釈し、小型噴霧
器で土壌表面に処理した。処理後第９表
２０日間温室内で育成し、除草効力および薬冬
像を調査した。その結果を第９表に示す。Table 8 Test Example 3 A cylindrical plastic pot with a diameter of 8 ann and a depth of 12 ann was filled with rice paddy soil, and seeds of Japanese millet and broad-leaved weeds (Azaena, Azalea, and Chickweed) were mixed in at a depth of 1 to 2 A11. After flooding the rice field and making it into a paddy field, rice plants at the 3-leaf stage were transplanted and grown in a greenhouse. After 6 days (at the beginning of each weed's emergence), the test compound was emulsified in accordance with Formulation Example 2. A vat with an area of 33 x 23 eIIIr 1 and a depth of 1 lan was filled with field soil, and then rice, corn, diver, mulva morning glory, Japanese radish, and Japanese dogwood were added. , Seiban sorghum, and hackberry were sown and covered with soil to a thickness of 1 to 2 ann. The test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount was added to 1
It was diluted with 10 liters of water per area and applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days as shown in Table 9, and their herbicidal efficacy and winter performance were investigated. The results are shown in Table 9.
試験例５
面積３３Ｘ２３ａｄ、深さ＋１−のバットに畑地土壌を
詰め、コムギ、オオムギ、サナエタデ、オオイヌノフグ
リ、フィールドパンジー、ヤエムグラを播種し、１〜２
ｃｍの厚さに覆土した。製剤例２に準じて供試化合物を
乳剤にし、その所定量を１アールあたり１０リツトル相
当の水で希釈し、小型噴霧器で土壌表面に処理した。処
理後２７日間温室内で育成し、除草効力および薬害を調
査した。その結果を第１Ｏ表に示す。Test Example 5 Fill a vat with an area of 33 x 23 ad and a depth of +1- with field soil, and sow wheat, barley, Japanese knotweed, field pansy, field pansy, and field soil.
It was covered with soil to a thickness of cm. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 27 days, and their herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 1O.
試験例６
面積３３Ｘ２３ｃｎｆ、深さｌ１ｃｍのバットに畑地土
壌を詰め、トウモロコシ、イネ、マルバアサガオ、オナ
モミ、イチビ、エビスグサ、イヌホオズキを播種し１８
日間育成した。その後、製剤例２に準じて供試化合物を
乳剤にし、その所定量を１アールあたり１０リツトル相
当の水で希釈し、小型噴霧器で植物体の上方から茎葉部
会面に均一に処理した。このとき雑草および作物の生育
状況は草種により異なるが、１〜４葉期で、草丈は２〜
１２ａｎであった。処理２０日後に除草効力および薬害
を調査した。その結果を第１＋表に示す。Test Example 6 A vat with an area of 33 x 23 cnf and a depth of 1 cm was filled with field soil, and corn, rice, morning glory, Japanese fir tree, Japanese crocodile, Ebisu grass, and Japanese Physalis were sown.
It was grown for days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was uniformly applied from above the plant to the surface of the leaves using a small sprayer. At this time, the growth status of weeds and crops differs depending on the grass species, but the 1- to 4-leaf stage and the plant height are 2- to 4-leaf stages.
It was 12an. Herbicidal efficacy and phytotoxicity were investigated 20 days after treatment. The results are shown in Table 1+.
なお、本試験は、全期間を通して温室内で行なった。This test was conducted in a greenhouse throughout the entire period.
第１０表
第１１表
試験例７
面積３３Ｘ２３ａｌ、ｆＨさ１１０のハツトに畑地土壌
を詰め、コムギ、オオムギ、サナエタデ、ヤエムグラ、
ハコベ、オオイヌノフグリ、フィールドパンジーを播種
し、２５日間育成した。その後、製剤例２に準じて供試
化合物を乳剤にし、その所定量を１アールあたり１０リ
ツトル相当の水で希釈し、小型噴霧器で植物体の上方か
ら茎葉部会面に均一に処理した。このとき雑草および作
物の生育状況は車種により異なるが、１〜４葉期で、草
丈は２〜１２ａｎであった。処理２７日後に除草効力お
よび薬害を調査した。その結果を第１２表に示す。なお
、本試験は全期間を通して温室内で行なった。Table 10 Table 11 Test Example 7 A hat with an area of 33 x 23 al and a fH of 110 was filled with field soil, and wheat, barley, Japanese knotweed, Japanese violet grass, etc.
Chickweed, giant dogweed, and field pansies were sown and grown for 25 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was uniformly applied from above the plant to the surface of the leaves using a small sprayer. At this time, the growth conditions of weeds and crops varied depending on the vehicle type, but they were in the 1-4 leaf stage and the plant height was 2-12 an. Herbicidal efficacy and phytotoxicity were investigated 27 days after treatment. The results are shown in Table 12. This test was conducted in a greenhouse throughout the entire period.
第１２表
試験例８
１１５０００ ａワグネルボットに水田土壌を詰め、ア
ゼナ、キカシグサ、ミゾハコベの種子を１〜２ｏｎの深
さに混ぜ込んだ。湛水して水田状態にした後、２葉期の
イネを移植し、温室内で育成した。４日後に製剤例２に
準じて供試化合物を乳剤にし、その所定量をｌＯミリリ
ットルの水で希釈して水面に処理し、その水深を４ａｏ
とした。処理後２０日間温室内で育成し、除草効力およ
び薬害を調査した。その結果を第１３表に示す。なお、
処理の翌日から２日間は、１日あたり３ａｎの水深に相
当する量の漏水を行なった。Table 12 Test Example 8 A 115,000 a Wagnerbot was filled with paddy soil, and seeds of azalea, azalea, and chickweed were mixed in to a depth of 1 to 2 ounces. After flooding the rice field to create a paddy field, two-leaf stage rice was transplanted and grown in a greenhouse. After 4 days, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with 10 milliliters of water and applied to the water surface.
And so. After treatment, the plants were grown in a greenhouse for 20 days, and their herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 13. In addition,
For two days from the day after the treatment, water was leaked in an amount equivalent to a water depth of 3 ann per day.
第１３表
試験例９
直径８国、深さ＋２ａｏの円筒量プラスチックポットに
水田土壌を詰め、タイヌビエ、広葉雑草（アゼナ、キカ
シグサ、ミゾハコベ）、ホタルイの種子を１〜２ｃｍの
深さに混ぜ込んだ。湛水して水田状態にした後、温室内
で育成した。６日後（各雑草の発生初期）に製剤例２に
準じて供試化合物を乳剤にし、その所定量を５ミリリツ
トルの水で希釈し、水面に処理した。処理後、２０日間
温室内で育成し、除草効力を調査した。その結果を第１
４表に示す。Table 13 Test Example 9 A cylindrical plastic pot with a diameter of 8 mm and a depth of +2 AO was filled with paddy soil, and seeds of Japanese millet, broad-leaved weeds (Azeena, Kikashigusa, Chickweed), and firefly were mixed in at a depth of 1 to 2 cm. . After being flooded into paddy fields, they were grown in a greenhouse. Six days later (at the beginning of each weed's emergence), the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with 5 milliliters of water, and the emulsion was applied to the water surface. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The result is the first
It is shown in Table 4.
第１４表
ムを播種し、１〜２Ｃ［１１の厚さに覆土した。製剤例
２に準じて供試化合物を乳剤にし、その所定量を１アー
ルあたりｌＯリットル相当の水で希釈し、小型噴霧器で
土壌表面に処理した。処理後２０日間温室内で育成し、
除草効力および薬害を調査した。その結果を第１５表に
示す。The 14th layer was sown and covered with soil to a thickness of 1 to 2C [11 cm. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. Grow in a greenhouse for 20 days after treatment,
Herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 15.
試験例１０
面積３３Ｘ２３ｃｏ？、深さ１１−の）く・ノド（＝畑
地土壌を詰め、ワタ、トウモロコシ、イネ、イチビ、オ
ナモミ、マルバアサガオ、イヌホオズキ、アオゲイトウ
、アメリカツノクサネ試験例１１
面積３３Ｘ２３ｃｊ、深さ１１０のバットに畑地土壌を
詰め、イヌビエ、セイバンモロコシ、エノコログサ、メ
ヒシバを播種し、１〜２ａｎの厚さに覆土した。製剤例
２に準じて供試化合物を乳剤にし、その所定量を１アー
ルあたりｌＯリットル相当の水で希釈し、小型噴霧器で
土壌表面に処理した。処理後２０日間温室内で育成し、
除草効力を調査した。その結果を第１６表に示す。Test example 10 Area 33x23co? , a depth of 11-) Filled with field soil, cotton, corn, rice, Japanese grass, Japanese fir, Japanese morning glory, Japanese Physalis, blue-bellied lily, American hornwort Test example 11 Area 33 x 23 cj, depth 110 in a bat Upland soil was packed, and golden millet, Seiban sorghum, hackberry, and crabgrass were sown, and the soil was covered to a thickness of 1 to 2 ann.The test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount was equivalent to 10 liters per are. It was diluted with water and treated on the soil surface with a small sprayer.After treatment, it was grown in a greenhouse for 20 days.
The herbicidal efficacy was investigated. The results are shown in Table 16.
第１６表
試験例１２
面積３３Ｘ２３Ｃｒｌ、深さ１１ｃｍのノ〈ットに畑地
土壌を詰め、コムギ、オオムギ、サナエタデ、ハコベ、
オオイヌノフグリ、シロザ、フィールドパンジーを播種
し、１〜２ａｎ（７）厚さに覆土した。製剤例２に準じ
て供試化合物を乳剤にし、その所定量を１アールあたり
１０リツトル相当の水で希釈し、小型噴霧器で土壌表面
に処理した。処理後２７日間温室内で育成し、除草効力
および薬害を調査した。Table 16 Test Example 12 A knot with an area of 33 x 23 Crl and a depth of 11 cm was filled with upland soil, and wheat, barley, Japanese knotweed, chickweed, etc.
Seeds of giant dogfish, white grass, and field pansies were sown, and the soil was covered with soil to a thickness of 1 to 2 an (7 cm). The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 27 days, and their herbicidal efficacy and phytotoxicity were investigated.
その結果を第１７表に示す。The results are shown in Table 17.
第１７表
試験例１３
面積３３Ｘ２３ａｌ、深さ１ｌａｎのバットに畑地土壌
を詰め、トウモロコツ、オナモミ、イチビ、マルバアサ
ガオ、エビスグサ、イヌホオズキ、イヌビエ、セイバン
モロコシを播種し、１８日間育成した。その後、製剤例
２に準じて供試化合物を乳剤にし、その所定量を１アー
ルあたり１０リツトル相当の水で希釈し、小型噴霧器で
植物体の上方から茎葉部全面に均一に処理した。このと
き雑草および作物の生育状況は草種により異なるが、１
〜４葉期で、草丈は２〜１２ａｎであった。処理２０日
後に除草効力および薬害を調査した。Table 17 Test Example 13 A vat with an area of 33 x 23 al and a depth of 1 lan was filled with field soil, and corn, Japanese fir, Japanese sorghum, Japanese morning glory, Ebisu grass, Japanese Physalis, Japanese commonweed, and Seiban sorghum were sown and grown for 18 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was uniformly applied from above to the entire surface of the plant with a small sprayer. At this time, the growth conditions of weeds and crops vary depending on the grass species, but 1
At the ~4-leaf stage, the plant height was 2-12 an. Herbicidal efficacy and phytotoxicity were investigated 20 days after treatment.
その結果を第１８表に示す。なお、本試験は全期間を通
して温室内で行なった。The results are shown in Table 18. This test was conducted in a greenhouse throughout the entire period.
試験例１４
面積３３Ｘ２３ａ［！、深さｌｌＣｌ！ｌのバットに畑
地土壌を詰め、コムギ、サナエタデ、ハコベ、オオイヌ
ノフグリ、フィールトパンジスズメノカタビラ、ノスズ
メノテッポウを播種し、２７日間育成した。その後、製
剤例２に準じて供試化合物を乳剤にし、その所定量を１
アールあたりｌＯリットル相当の水で希釈し、小型噴霧
器で植物体の上方から茎葉部会面に均一に処理した。こ
のとき雑草および作物の生育状況は草種により異なるが
、１〜４葉期で、草丈は２〜１２ａｎであった。処理２
７日後に除草効力および薬害を調査した。Test Example 14 Area 33x23a[! , depth llCl! Field soil was filled in a 1-liter vat, and wheat, Japanese knotweed, chickweed, giant dogweed, field panges staghorn, and sagebrush were sown and grown for 27 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount was
The solution was diluted with 10 liters of water per area and uniformly applied to the top and leaves of the plant using a small sprayer. At this time, the growth conditions of weeds and crops varied depending on the grass species, but they were in the 1-4 leaf stage and the plant height was 2-12 an. Processing 2
After 7 days, herbicidal efficacy and phytotoxicity were investigated.
その結果を第１９表に示す。なお、本試験は全期間を通
して温室内で行なった。The results are shown in Table 19. This test was conducted in a greenhouse throughout the entire period.
Claims (5)
ルオロエチル基を表わし、 Ｒ＾２はメチル基またはアミノ基を表わし、Ｒ＾３は水
素原子またはメチル基を表わし、Ｒ＾４はアルキル基、
アルケニル基、アルキニル基、ハロアルキル基、ハロア
ルケニル基またはアルコキシアルキル基を表わし、Ｘは
水素原子またはハロゲン原子を表わす。〕 で示されるベンゾオキサジルウラシル誘導体。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents a trifluoromethyl group or pentafluoroethyl group, R^2 represents a methyl group or an amino group, and R^3 represents a hydrogen atom or a methyl group, R^4 is an alkyl group,
It represents an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group or an alkoxyalkyl group, and X represents a hydrogen atom or a halogen atom. ] A benzoxadyluracil derivative represented by
ルオロエチル基を表わし、 Ｒ＾３は水素原子またはメチル基を表わし、Ｒ＾４はア
ルキル基、アルケニル基、アルキニル基、ハロアルキル
基、ハロアルケニル基またはアルコキシアルキル基を表
わし、Ｘは水素原子またはハロゲン原子を表わす。〕 で示される化合物をメチル化またはアミノ化することを
特徴とする請求項１記載のベンゾオキサジルウラシル誘
導体の製造法。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents a trifluoromethyl group or a pentafluoroethyl group, R^3 represents a hydrogen atom or a methyl group, and R^4 represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, or an alkoxyalkyl group, and X represents a hydrogen atom or a halogen atom. ] The method for producing a benzoxazyluracil derivative according to claim 1, characterized in that the compound represented by these is methylated or aminated.
を有効成分として含有することを特徴とする除草剤。(3) A herbicide containing the benzoxadyluracil derivative according to claim 1 as an active ingredient.
ルオロエチル基を表わし、 Ｒ＾３は水素原子またはメチル基を表わし、Ｒ＾４はア
ルキル基、アルケニル基、アルキニル基、ハロアルキル
基、ハロアルケニル基またはアルコキシアルキル基を表
わし、Ｘは水素原子またはハロゲン原子を表わす。〕 で示される化合物。(4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 represents a trifluoromethyl group or a pentafluoroethyl group, R^3 represents a hydrogen atom or a methyl group, and R^4 represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, or an alkoxyalkyl group, and X represents a hydrogen atom or a halogen atom. ] A compound represented by
ルオロエチル基を表わし、 Ｒ＾３は水素原子またはメチル基を表わす。 〕 で示される化合物。(5) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents a trifluoromethyl group or a pentafluoroethyl group, and R^3 represents a hydrogen atom or a methyl group. ] A compound represented by
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25032089 | 1989-09-26 | ||
| JP2-136498 | 1990-05-24 | ||
| JP13649890 | 1990-05-24 | ||
| JP1-250320 | 1990-05-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0474174A true JPH0474174A (en) | 1992-03-09 |
| JP3064371B2 JP3064371B2 (en) | 2000-07-12 |
Family
ID=26470055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP02256449A Expired - Fee Related JP3064371B2 (en) | 1989-09-26 | 1990-09-25 | Benzoxazyluracil derivative, process for producing the same and herbicide containing the same as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3064371B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013510810A (en) * | 2009-11-13 | 2013-03-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 3- (3,4-Dihydro-2H-benzo [1,4] oxazin-6-yl) -1H-pyrimidine-2,4-dione compounds as herbicides |
| JP2020528896A (en) * | 2017-07-24 | 2020-10-01 | レダッグ クロップ プロテクション リミテッド | Benzooxadinone derivative useful as a herbicide |
-
1990
- 1990-09-25 JP JP02256449A patent/JP3064371B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013510810A (en) * | 2009-11-13 | 2013-03-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 3- (3,4-Dihydro-2H-benzo [1,4] oxazin-6-yl) -1H-pyrimidine-2,4-dione compounds as herbicides |
| JP2020528896A (en) * | 2017-07-24 | 2020-10-01 | レダッグ クロップ プロテクション リミテッド | Benzooxadinone derivative useful as a herbicide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3064371B2 (en) | 2000-07-12 |
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