JPH04108777A - Pyrimidine derivative and herbicide - Google Patents
Pyrimidine derivative and herbicideInfo
- Publication number
- JPH04108777A JPH04108777A JP22925990A JP22925990A JPH04108777A JP H04108777 A JPH04108777 A JP H04108777A JP 22925990 A JP22925990 A JP 22925990A JP 22925990 A JP22925990 A JP 22925990A JP H04108777 A JPH04108777 A JP H04108777A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- japanese
- water
- compound
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- 239000004009 herbicide Substances 0.000 title claims abstract description 9
- 150000003230 pyrimidines Chemical class 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 30
- -1 (substituted) phenylthio, pyrrole Chemical class 0.000 abstract description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002689 soil Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- 240000001341 Reynoutria japonica Species 0.000 description 11
- 235000018167 Reynoutria japonica Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000301850 Cupressus sempervirens Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000008096 xylene 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
- KSHVLQBPQNIFDW-UHFFFAOYSA-N 2-acetyl-6-sulfanylbenzoic acid Chemical compound CC(=O)C1=CC=CC(S)=C1C(O)=O KSHVLQBPQNIFDW-UHFFFAOYSA-N 0.000 description 2
- SQSKOSICCNPQQW-UHFFFAOYSA-N 2-methylsulfanyl-6-sulfanylbenzoic acid Chemical compound CSC1=CC=CC(S)=C1C(O)=O SQSKOSICCNPQQW-UHFFFAOYSA-N 0.000 description 2
- CHNZMLJFMJNPJO-UHFFFAOYSA-N 2-phenylsulfanylpyrimidine Chemical compound N=1C=CC=NC=1SC1=CC=CC=C1 CHNZMLJFMJNPJO-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000254158 Lampyridae Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 244000078534 Vaccinium myrtillus Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- SRKIJSXUFKQFPE-UHFFFAOYSA-N 2-fluoro-6-methylsulfanylbenzonitrile Chemical compound CSC1=CC=CC(F)=C1C#N SRKIJSXUFKQFPE-UHFFFAOYSA-N 0.000 description 1
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 description 1
- 241001311476 Abies veitchii Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241001647031 Avena sterilis Species 0.000 description 1
- 235000004535 Avena sterilis Nutrition 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001038806 Carex kobomugi Species 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
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- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001520921 Leersia virginica Species 0.000 description 1
- 240000000486 Lepidium draba Species 0.000 description 1
- 235000000391 Lepidium draba Nutrition 0.000 description 1
- 241001124553 Lepismatidae Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 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
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 235000019693 cherries Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、新規なピリミジン誘導体並びにその塩及びこ
れを有効成分として含有する水田、畑及び非農耕地等に
適用できる除草剤に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a novel pyrimidine derivative, a salt thereof, and a herbicide containing the same as an active ingredient and which can be applied to rice fields, fields, non-agricultural land, etc. .
（従来の技術）
特開昭６２−１７４０５９号公報明細書、特開昭５４−
５．５７２９号公報明細書及びアグリカルチュラル・ア
ンド・バイオロジカル・ケミストリ（Ａｇｒｉｃａｌｔ
ｕｒａｌ ａｎｄ Ｂｉｏｌｏｇｉｃａｌ Ｃｈ
ｅｍｉｓｔｒｙ） ３０巻、９号、８９６頁（１９
６６年）には、２−フェノキシビリミジン誘導体ならび
に２−フェニルチオピリミジン銹導体が除草作用を有す
ることが記載されている。(Prior art) Specification of JP-A-62-174059, JP-A-54-
5.5729 and Agricultural and Biological Chemistry (Agricultural and Biological Chemistry)
Ural and Biological Ch.
volume 30, issue 9, page 896 (19
1966) describes that 2-phenoxypyrimidine derivatives and 2-phenylthiopyrimidine conductors have herbicidal activity.
（発明が解決しようとする問題点）
しかしながら、これらに記載された化合物は除幕効果が
不十分であったり、一部の作物に対する安全性の点で問
題がある。(Problems to be Solved by the Invention) However, the compounds described in these documents have insufficient unveiling effects or have problems in terms of safety for some crops.
本発明者らはピリミジン系化合物について、更に改良さ
れた化合物を開発することを目的に鋭意研究した結果、
フェニルチオピリミジン銹導体のピリミジン環及びベン
ゼン環上の特定の位置に置換基を配した本発明化合物が
一年生雑葦はもとより多年生雑草に対して優れた除草効
果を示すとともに、作物、特に棉に対する安全性の高い
ものであることを見いだし、本発明を完成した。As a result of intensive research into pyrimidine compounds with the aim of developing further improved compounds, the present inventors found that
The compound of the present invention, which has a substituent at a specific position on the pyrimidine ring and benzene ring of a phenylthiopyrimidine conductor, exhibits excellent herbicidal effects against annual weeds as well as perennial weeds, and is safe for crops, especially cotton. They found that it has high properties and completed the present invention.
（問題点を解決する為の手段）
本発明のピリミジン銹導体は一般式
（式中、Ｘはニトロ基、アルキル基、アルコキシ基、ア
ルキルチオ基、ハロアルキル基、ハロゲン原子、アシル
基、アルコキシカルボニル基、アルコキシアルコキシ基
、フェノキシアルコキシ基、アルコキシアルキルチオ基
、アルキル基またはハロゲン原子で置換されてもよいフ
ェニルチオ基、ビロール基またはシクロアルキルアルコ
キシ基を示し、Ｒは水素原子、アルキル基またはベンジ
ル基を示し、ｎは１または２の整数を示す。但し。(Means for Solving the Problems) The pyrimidine rust conductor of the present invention has the general formula (wherein, an alkoxyalkoxy group, a phenoxyalkoxy group, an alkoxyalkylthio group, an alkyl group, or a phenylthio group optionally substituted with a halogen atom, a virol group, or a cycloalkylalkoxy group, R represents a hydrogen atom, an alkyl group, or a benzyl group, and n indicates an integer of 1 or 2. However,
Ｘがアルキル基またはハロゲン原子を示すときｎは２を
示す。）にて表される。When X represents an alkyl group or a halogen atom, n represents 2. ).
また、一般式［Ｉ］のＲが水素原子の場合は、遊離型で
もよいし、塩の形でもよい。これらの塩としてはアルカ
リ金属塩５アルカリ土類金属城、遷移金属塩及び有機ア
ンモニウム塩がある。Further, when R in the general formula [I] is a hydrogen atom, it may be in a free form or in a salt form. These salts include alkali metal salts, alkaline earth metal salts, transition metal salts, and organic ammonium salts.
前記一般式［１１で表される本発明化合物を第１表に例
示する。なお化合物番号は以後の記載において参照され
る。The compounds of the present invention represented by the general formula [11] are illustrated in Table 1. Note that the compound number will be referred to in the following description.
（以下余白）
第１表
第１表つづき
本発明化合物は次の方法に従って製造することができる
。(The following is a blank space) Table 1 Table 1 continued The compound of the present invention can be produced according to the following method.
〔則 ［１１１１［１〕
（式中、Ｙ“はハロゲン原子、アルキルスルホニル基、
ベンジルスルホニル基、または置換ベンジルスルホニル
基を示し、Ｘ、Ｒ及びｎは前記と同じ意味を示す。）
すなわち、式［同で示される本発明化合物は、式（Ｕ］
で示される化合物と式［ＩＩＩ］ で示される化合物と
を塩基の存在下、好ましくは不活性溶媒中で、室温から
溶媒の濁点の温度範囲で１〜２４時間反応させることに
より、製造することができる。無溶媒で反応を行う場合
には、塩基として無水炭酸カリウムのようなアルカリ金
属の炭酸塩などを使用し、１２０〜１６０℃の温度範囲
内で反応させる。[Rule [1111[1] (In the formula, Y" is a halogen atom, an alkylsulfonyl group,
It represents a benzylsulfonyl group or a substituted benzylsulfonyl group, and X, R and n have the same meanings as above. ) That is, the compound of the present invention represented by the formula [the formula (U]
It can be produced by reacting the compound represented by the formula [III] with the compound represented by the formula [III] in the presence of a base, preferably in an inert solvent, at a temperature ranging from room temperature to the cloudy point of the solvent for 1 to 24 hours. can. When the reaction is carried out without a solvent, an alkali metal carbonate such as anhydrous potassium carbonate is used as a base, and the reaction is carried out within a temperature range of 120 to 160°C.
溶媒としてはベンゼン、トルエン、キシレンなどの炭化
水素系溶媒、塩化メチレン、クロロホルムなどのハロゲ
ン化炭化水素系溶媒、メタノール、エタノール、２−プ
ロパツールなどのアルコール系溶媒、ジエチルエーテル
、イソプロピルエーテル、テトラヒドロフラン、１．４
−ジオキサンなどのエーテル系溶媒、アセトン、メチル
エチルケトンなどのケトン系溶媒、酢酸メチル、酢酸エ
チルなどのエステル系溶媒、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
キシドなどの非プロトン性極性溶媒、アセトニトリル及
び水などが使用できる。また、塩基としては金属ナトリ
ウム、金属カリウムなどのアルカリ金属類、水素化ナト
リウム、水素化カリウム、水素化カルシウムなどの水素
化アルカリ金属及び水素化アルカリ土類金属類、炭酸ナ
トリウム、炭酸カリウム、炭酸カルシウム、炭酸水素ナ
トリウム、炭酸水素カリウムなどの炭酸塩類、水酸化ナ
トリウム、水酸化カリウム及び水酸化カルシウムなどの
水酸化金属類が使用できる。Examples of solvents include hydrocarbon solvents such as benzene, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride and chloroform, alcohol solvents such as methanol, ethanol, and 2-propanol, diethyl ether, isopropyl ether, tetrahydrofuran, 1.4
- Ether solvents such as dioxane, ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide. Solvents such as acetonitrile and water can be used. In addition, bases include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, sodium carbonate, potassium carbonate, and calcium carbonate. , carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, and metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide.
また、本発明化合物は次の方法によっても製造すること
ができる。The compound of the present invention can also be produced by the following method.
［ＩＶｌ ［Ｖ］ ［Ｖ［］
（式中、Ｒ，Ｘ及びｎは前記と同じ意味を表す。）すな
わち、式（１１で示される本発明化合物は、塩基性溶液
中において低温、好ましくは一２０〜１０℃の温度範囲
内で式［ＩＶ）で示されるアニリン誘導体からジアゾニ
ウム塩ＥＶ］ を製造し、このジアゾニウム塩［Ｖ］
と式［ＶＩ］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。ジアゾニウム塩としては、
塩酸塩のほかに臭化水素酸塩、ヨウ化水素酸塩、テトラ
フルオロホウ酸塩及び硫酸塩などがある。また、塩基性
溶液は溶媒に水酸化ナトリウム、水酸化カリウム、水酸
化バリウム及び水酸化カルシウムなどの強塩基類を加え
ることにより製造できる。[IVl [V] [V[]
(In the formula, R, A diazonium salt EV] is produced from the aniline derivative represented by the formula [IV), and the diazonium salt [V]
It can be produced by reacting with a compound represented by formula [VI]. As a diazonium salt,
In addition to hydrochloride, there are hydrobromide, hydroiodide, tetrafluoroborate, and sulfate. Moreover, a basic solution can be produced by adding strong bases such as sodium hydroxide, potassium hydroxide, barium hydroxide, and calcium hydroxide to a solvent.
以上のようにして製造された２−（４，６−シメトキシ
ビリミジンー２−イルチオ）安息香酸はアルコールまた
は水中で等量の重曹、水酸化ナトリウム、水酸化カリウ
ム、水素化ナトリウムなどと反応させてアルカリ金属塩
とすることができる。2-(4,6-Simethoxypyrimidin-2-ylthio)benzoic acid produced as above is reacted with equal amounts of baking soda, sodium hydroxide, potassium hydroxide, sodium hydride, etc. in alcohol or water. can be made into an alkali metal salt.
また、アルカリ金属塩に塩化カルシウムを反応させるか
、相当する安息香酸に炭酸カルシウム、水素化カルシウ
ムを反応させ、アルカリ土類金属塩とすることができる
。さらに、アルカリ金属塩に塩化鉄などを反応させ、鉄
などの遷移金属塩とすることができる。Moreover, an alkaline earth metal salt can be obtained by reacting an alkali metal salt with calcium chloride or reacting the corresponding benzoic acid with calcium carbonate or calcium hydride. Furthermore, a transition metal salt such as iron can be obtained by reacting an alkali metal salt with iron chloride or the like.
さらに、第１級アミン、第２級アミン、第３級アミン、
ジェタノールアミン、トリエタノールアミン、アルコキ
シアルキルアミン、シクロヘキシルアミン、モルホリン
などの脂肪族アミンまたはアニリン、ナフチルアミン等
の芳香族アミンを反応させて有機アンモニウム塩とする
ことができる。Furthermore, primary amines, secondary amines, tertiary amines,
An organic ammonium salt can be obtained by reacting aliphatic amines such as jetanolamine, triethanolamine, alkoxyalkylamine, cyclohexylamine, and morpholine, or aromatic amines such as aniline and naphthylamine.
次に実施例をあげて本発明化合物の製造法を具体的に説
明する。Next, the method for producing the compound of the present invention will be specifically explained with reference to Examples.
実施例１６−アセチル−２−（４，６−シメトキシビリ
ミジンー２−イルチオ）安息
香酸（化合物８）の合成
２−アミノ−６−アセチル安息香酸塩酸塩６゜０ｇを濃
塩酸９ｍＱ及び亜硝酸ナトリウム２，３ｇでジアゾニウ
ム塩とした後、このジアゾニウム塩をあらかじめ調製し
た二硫化ナトリウム水溶液（硫化ナトリウムの９含水物
８．３ｇ、硫黄１．１ｇ、水酸化ナトリウム２．６ｇ及
び水１５ｍｇより調製）に０〜５℃で徐々に滴下した。Example 1 Synthesis of 6-acetyl-2-(4,6-cymethoxypyrimidin-2-ylthio)benzoic acid (compound 8) After making a diazonium salt with 2.3 g of sodium nitrate, this diazonium salt was converted into a previously prepared aqueous sodium disulfide solution (prepared from 8.3 g of 9-hydrated sodium sulfide, 1.1 g of sulfur, 2.6 g of sodium hydroxide, and 15 mg of water). ) was gradually added dropwise at 0 to 5°C.
滴下終了後、室温下で２時間撹拌して反応終了とした。After the dropwise addition was completed, the mixture was stirred at room temperature for 2 hours to complete the reaction.
反応液は多量の水に注ぎ、濃塩酸を加えた後、酢酸エチ
ルで抽出した。酢酸エチル層に炭酸水素ナトリウム水溶
液を加え、炭酸水素ナトリウム可溶分を抽出した。この
水溶液にピロ硫酸ナトリウム７゜０ｇを加え、３０分間
還流して反応終了とした。The reaction solution was poured into a large amount of water, concentrated hydrochloric acid was added thereto, and then extracted with ethyl acetate. An aqueous sodium hydrogen carbonate solution was added to the ethyl acetate layer to extract the sodium hydrogen carbonate soluble content. 7.0 g of sodium pyrosulfate was added to this aqueous solution, and the mixture was refluxed for 30 minutes to complete the reaction.
反応液に濃塩酸を加えた後、酢酸エチルで抽出した。抽
出液は乾燥した後、溶剤を減圧下に留去して６−アセチ
ル−２−メルカプト安息香酸５．０ｇ（収率７７％）を
得た。After adding concentrated hydrochloric acid to the reaction solution, the mixture was extracted with ethyl acetate. After the extract was dried, the solvent was distilled off under reduced pressure to obtain 5.0 g (yield: 77%) of 6-acetyl-2-mercaptobenzoic acid.
次いで、６−アセチル−２−メルカプト安息香酸５．０
ｇ、４，６−シメトキシー２−メチルスルホニルピリミ
ジン６．７ｇ及び無水炭酸カリウム３．５ｇをジメチル
スルホキシド：２０ ｍ Ｑに懸濁させた後、室温で１
時間撹拌した。反応液を多量の水に注ぎ、クロロホルム
で洗浄した。水層に濃塩酸を加え酸性とし、生成した油
状物をジエチルエーテルで抽出した。ジエチルエーテル
層は、水洗、乾燥したのち不純物を除くためフロリジル
（Ｆｌｏｒｉｓｉｌ）の層を通した。その後、溶媒を減
圧上留去して微黄色粉末の目的化合物１．Ｉｇを得た。Then 6-acetyl-2-mercaptobenzoic acid 5.0
After suspending 6.7 g of 4,6-simethoxy-2-methylsulfonylpyrimidine and 3.5 g of anhydrous potassium carbonate in 20 mQ of dimethyl sulfoxide,
Stir for hours. The reaction solution was poured into a large amount of water and washed with chloroform. The aqueous layer was made acidic by adding concentrated hydrochloric acid, and the resulting oil was extracted with diethyl ether. The diethyl ether layer was washed with water, dried, and then passed through a layer of Florisil to remove impurities. Thereafter, the solvent was distilled off under reduced pressure to obtain the target compound 1. as a pale yellow powder. Ig was obtained.
融点１７７〜１８０℃。Melting point: 177-180°C.
実施例２ ２−（４，６−シメトキシビリミジンー２−
イルチオ）−６−メチルチオ安
息香酸（化合物１８）の合成
６−フルオル−２−メチルチオベンゾニトリル１６．７
ｇおよび水硫化ナトリウム１０．４ ｇをジメチルス
ルホキシドｌｏｏｍＱに懸濁させ、８０℃で２時間加熱
攪拌した。終了後、混合物を多量の氷水にあけ、さらに
水酸化ナトリウムで溶液のｐＨを１１−１２にＩＲ整し
たのち中性分をクロロホルムで抽出した。水層を濃塩酸
で酸性にし、生成した油状分を酢酸エチルで抽出、水洗
、乾燥したのち溶媒を留去し、油状物質８．３ｇを得た
。Example 2 2-(4,6-cymethoxypyrimidine-2-
Synthesis of ylthio)-6-methylthiobenzoic acid (compound 18) 6-Fluoro-2-methylthiobenzonitrile 16.7
g and 10.4 g of sodium hydrosulfide were suspended in dimethyl sulfoxide roomQ, and the mixture was heated and stirred at 80° C. for 2 hours. After the completion of the reaction, the mixture was poured into a large amount of ice water, the pH of the solution was adjusted to 11-12 using sodium hydroxide, and the neutral components were extracted with chloroform. The aqueous layer was made acidic with concentrated hydrochloric acid, and the resulting oil was extracted with ethyl acetate, washed with water, dried, and the solvent was distilled off to obtain 8.3 g of an oily substance.
次に、油状物質６．３ｇ、硫化ナトリウム８．３ｇ、水
酸化ナトリウム７．０ｇ及び水３０ｍ２からなる水溶液
をオートクレーブに封入し、液温１７０〜１８０℃、内
圧８〜ｌ ０Ｋｇ７ｃｍ”で７時間加熱した。冷却後、
氷水にあけｐＨを９〜１０に調整し、クロロホルムで洗
浄した。水層は、濃塩酸で酸性にし生成した油状分を酢
酸エチルで抽出した。有機層を水洗、乾燥した後、溶剤
を減圧上留去して６−メチルチオ−２−メルカプト安息
香酸６．６ｇを得た。Next, an aqueous solution consisting of 6.3 g of oily substance, 8.3 g of sodium sulfide, 7.0 g of sodium hydroxide, and 30 m2 of water was sealed in an autoclave and heated at a liquid temperature of 170 to 180°C and an internal pressure of 8 to 10 kg, 7 cm for 7 hours. After cooling,
The mixture was poured into ice water, the pH was adjusted to 9 to 10, and the mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid, and the resulting oil was extracted with ethyl acetate. After washing the organic layer with water and drying, the solvent was distilled off under reduced pressure to obtain 6.6 g of 6-methylthio-2-mercaptobenzoic acid.
次いで、６−メチルチオ−２−メルカプト安息香酸３．
Ｏｇ、４．６−シメトキシー２−メチルスルホニルピリ
ミジン３．６ｇ及び水酸化ナトリウム２．１ｇを、Ｎ、
Ｎ−ジメチルホルムアミド１５ｒｎＱ、水１０ｍｇの混
合液に溶かし、室温で３時間攪拌した。反応液を多量の
水に注ぎ、グロロホルムで洗浄した。水層に濃塩酸を加
え酸性とし、生成した油状物をジエチルエーテルで抽出
した。Then 6-methylthio-2-mercaptobenzoic acid 3.
Og, 3.6 g of 4,6-simethoxy-2-methylsulfonylpyrimidine and 2.1 g of sodium hydroxide, N,
It was dissolved in a mixture of N-dimethylformamide 15rnQ and water 10mg, and stirred at room temperature for 3 hours. The reaction solution was poured into a large amount of water and washed with chloroform. The aqueous layer was made acidic by adding concentrated hydrochloric acid, and the resulting oil was extracted with diethyl ether.
ジエチルエーテル層は、水洗、乾燥したのち不純物を除
くためフロリジル（Ｆｌｏｒｉｓｉｌ）の層を通した。The diethyl ether layer was washed with water, dried, and then passed through a layer of Florisil to remove impurities.
その後、溶媒を減圧上留去して白色粉末の目的化合物１
．４ｇを得た。融点１４５〜１４７℃。Then, the solvent was distilled off under reduced pressure to obtain the target compound 1 as a white powder.
．． 4g was obtained. Melting point 145-147°C.
実施例３６−メドキシー２− （４，６−シメトキシビ
リミジンー２−イルチオ）安息
香酸メチル（化合物７）の合成
テトラヒドロフランとＮ、Ｎ−ジメチルホルムアミドの
１＝１混合液（’２０ｍＱ）に６０％水素化ナトリウム
０．２ｇを懸濁した後、６−メドキシー２− （４，６
−シメトキシピリミジー２−イルチオ）安息香酸１．６
ｇを加え、３０分間攪拌した。次に、ヨウ化メチル０．
８ｇを室温下に滴下し、さらに３時間攪拌した。混合液
を水に注ぎ、トルエンと酢酸エチルの混合液で抽出した
。抽出液を水洗、乾燥したのち、溶媒を減圧下で留去し
て白色固体の目的化合物１．４ｇを得た。融点１２０〜
＋２１’ｌ：。Example 36 - Synthesis of methyl medoxy 2- (4,6-cymethoxypyrimidin-2-ylthio)benzoate (compound 7) After suspending 0.2 g of % sodium hydride, 6-medoxy 2- (4,6
-cymethoxypyrimidi-2-ylthio)benzoic acid 1.6
g and stirred for 30 minutes. Next, methyl iodide 0.
8 g was added dropwise to the mixture at room temperature, and the mixture was further stirred for 3 hours. The mixture was poured into water and extracted with a mixture of toluene and ethyl acetate. After washing the extract with water and drying, the solvent was distilled off under reduced pressure to obtain 1.4 g of the target compound as a white solid. Melting point 120~
+21'l:.
本発明の除草剤は、一般式［ｒｌで示されるピリミジン
誘導体及びその塩を有効成分としてなる。The herbicide of the present invention contains a pyrimidine derivative represented by the general formula [rl and a salt thereof as an active ingredient.
本発明化合物を除草剤として水田、畑地、樹園地、非農
耕地等に使用する場合、その目的に応じて有効成分を適
当な剤型で用いることができる。When the compound of the present invention is used as a herbicide in rice fields, fields, orchards, non-agricultural lands, etc., the active ingredient can be used in an appropriate dosage form depending on the purpose.
通常の場合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剤、分散剤、補助剤等
を配合して、粉剤、水和剤、乳剤、粒剤等の各種形態に
製剤して使用することができる。製剤化に際して用いら
れる担体としては、例えばジ−クライト、タルク、ベン
トナイト、クレー、カオリン、珪藻土、ホワイトカーボ
ン、バーミキュライト、消石灰、珪砂、硫安、尿素等の
固体担体、２−プロパツール、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あげられる。In normal cases, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, surfactants, dispersants, adjuvants, etc. are added to form powders, wettable powders, emulsions, granules, etc. It can be formulated and used in various forms. Examples of carriers used in formulation include solid carriers such as dicrite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea, 2-propanol, xylene, cyclohexanone, Examples include liquid carriers such as methylnaphthalene.
界面活性剤及び分散剤としては、例えばアルコール硫酸
エステル塩、アルキルアリールスルホン酸塩、リグニン
スルホン酸塩、ポリオキシエチレングリコールエーテル
、ポリオキシエチレンアルキルアリールエーテル、ポリ
オキシエチレンソルビタンモノアルキレート等があげら
れる。Examples of surfactants and dispersants include alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene sorbitan monoalkylates. .
補助剤としては、例えばカルボキシメチルセルロース、
ポリエチレングリコール、アラビアゴム等があげられる
。使用に際しては、適当な濃度に希釈して散布するが、
または直接施用する。本発明化合物は有効成分でｌｏア
ール当り０．Ｉｇ〜ＩＫｇ施用する。Examples of adjuvants include carboxymethyl cellulose,
Examples include polyethylene glycol and gum arabic. When using it, dilute it to an appropriate concentration and spray it.
Or apply directly. The compound of the present invention has an active ingredient of 0.0% per lo are. Apply Ig to IKg.
また、本発明の化合物は必要に応じて殺虫剤、殺菌剤、
他の除草剤、植物生長調節剤、肥料等と混用してもよい
。In addition, the compound of the present invention may be used as an insecticide, fungicide, or
It may be used in combination with other herbicides, plant growth regulators, fertilizers, etc.
次に代表的な製剤例をあげて１１！剤方法を具体的に説
明する。以下の説明において「部」は重量部を意味する
。Next, we will give 11 representative formulation examples! The agent method will be specifically explained. In the following description, "part" means part by weight.
製剤例１ 水和剤
化合物（６）の１０部にエマルゲン（花王株式会社の登
録商標）８ＩＯの０．５部、デモール（花王株式会社の
登録商標）Ｎの０．５部、クニライト（クニミネ工業株
式会社の登録商標）２０１の２０部、ジ−クライト（ジ
−クライト株式会社の登録商標）ＣＡの６９部を混合粉
砕し、水和剤を得る。Formulation Example 1 10 parts of wettable powder compound (6), 0.5 part of Emulgen (registered trademark of Kao Corporation) 8IO, 0.5 part of Demol (registered trademark of Kao Corporation) N, Kunilite (Kunimine Kogyo Co., Ltd.) 201 (registered trademark of ZICRITE Co., Ltd.) and 69 parts of ZICRITE CA (registered trademark of ZICRITE Co., Ltd.) are mixed and ground to obtain a wettable powder.
製剤例２ 水和剤 化合物（８）の１０部にエマルゲン８１０の。。Formulation example 2 Hydrating agent of Emulgen 810 to 10 parts of compound (8). .
５部、デモールＮの０．５部、クニライト２０１の２０
部、カープレックス８ｏの５部、ジ−クライトＣＡの６
４部を混合粉砕し、水和剤を得る。5 parts, 0.5 parts of Demol N, 20 of Kunilite 201
Part 5 of Carplex 8o, Part 6 of Zeekrite CA
4 parts were mixed and ground to obtain a wettable powder.
製剤例３ 乳剤
化合物（１５）の３０部にキシレンとイソホロンの等量
混合物６０部、界面活性剤ツルポール（東邦化学工業株
式会社の登録商標）８００Ａの１０部を加え、これらを
よくかきまぜることによって乳剤を得る。Formulation Example 3 To 30 parts of emulsion compound (15), 60 parts of a mixture of equal amounts of xylene and isophorone and 10 parts of surfactant Tsurupol (registered trademark of Toho Chemical Industry Co., Ltd.) 800A are added, and these are thoroughly stirred to form an emulsion. get.
製剤例４ 粒剤
化合物（１８）の１部部、タルクとベントナイトを１＝
３の割合の混合した増量剤の８０部、ホワイトカーボン
の５部、界面活性剤ツルポール８００Ａのの５部に水１
０部を加え、よく練ってペースト状としたものを直径０
．７ｍｍのふるい穴から押し出して乾燥した後に０．５
〜１ｍｍの長さに切断し、粒剤を得る。Formulation Example 4 One part of granule compound (18), one part of talc and one part of bentonite
80 parts of bulking agent mixed in a ratio of 3 parts, 5 parts of white carbon, 5 parts of surfactant Tsurupol 800A and 1 part of water.
Add 0 parts and knead well to make a paste with a diameter of 0.
．． After extruding through a 7mm sieve hole and drying, 0.5
Cut into lengths of ~1 mm to obtain granules.
（発明の効果）
一般式［＋］で表される本発明の化合物及びその塩は、
水田に発生するタイヌビエ、タマガヤツリ、コナギ等の
一年生雑草及びウリカワ、ミズガヤツリ、クログワイ、
ホタルイ、ヘラオモダカ等の多年生雑草の発芽時から生
育期の広い範囲にわたって、極めて低い薬量で優れた除
草効果を発揮する。また、畑地においても問題となる種
々の雑草、例えばオオイヌタデ、アオビユ、シロザ、ハ
コベ、イチビ、アメリカキンゴジカ、アサガオ、オナモ
ミ等の広葉雑草をはじめ、ハマスゲ、キハマスゲ、ヒメ
クグ、カヤツリグサ、コゴメガヤツリ等の多年生および
１年生カヤツリグサ科雑草、ヒエ、メヒシバ、エノコロ
グサ、スズメノカタビラ、ジョンソングラス、ノスズメ
ノテツボウ、野生エンバク等のイネ科雑草を有効に防除
することができる。一方、本発明の除草剤は作物に対す
る安全性も高く、中でも稲、小麦、大豆及び棉等に対し
て高い安全性を示す。(Effect of the invention) The compound of the present invention represented by the general formula [+] and its salt are:
Annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, and Japanese cypress;
It exhibits excellent herbicidal effects at extremely low dosages over a wide range of perennial weeds, such as firefly and grasshopper, from the time of germination to the growing season. In addition, there are various weeds that can be a problem in fields, such as broad-leaved weeds such as Japanese knotweed, Japanese knotweed, whiteweed, chickweed, Japanese chickweed, Japanese goldenrod, morning glory, and Japanese fir tree, as well as perennial weeds such as Japanese knotweed, Japanese yellowtail, Japanese cypress, Japanese cyperus, and Japanese cyperus. It is possible to effectively control grass weeds such as annual Cyperaceae weeds, barnyard grass, grasshopper, foxtail grass, sycamore grass, johnson grass, sycamore grass, and wild oat. On the other hand, the herbicide of the present invention is highly safe for crops, especially rice, wheat, soybeans, cotton, and the like.
次に試験例をあげて本発明化合物の奏する効果を説明す
る。Next, the effects of the compounds of the present invention will be explained by giving test examples.
試験例１ （水田土壌処理による除草効果試験）１００
ｃｍ″のプラスチックポットに水田土壌を充填し、代掻
後、タイヌビエ（Ｅｃ）、コナギ（Ｍｏ）及びホタルイ
（Ｓｃ）の各種子を０．５ｃｍの深さに播種し、水深３
ｃｍに湛水した。翌日、製剤例１に準じて調製した水和
剤を水で希釈し、水面滴下処理した。施用量は、有効成
分を１０アール当り１００ｇとした。その後、温室内で
育成し、処理後２８日１に第２表の基準に従い、除草効
果を調査した。その結果を第３表に示した。Test example 1 (herbicidal effect test by paddy soil treatment) 100
Fill paddy soil in a plastic pot of 1.5 cm in size, and after puddling, sow seeds of Japanese millet (Ec), Japanese moss (Mo), and bulrush (Sc) at a depth of 0.5 cm, and place the seeds in a water depth of 3 cm.
It was flooded to cm. The next day, the wettable powder prepared according to Formulation Example 1 was diluted with water and dropped onto the water surface. The application amount was 100 g of active ingredient per 10 ares. Thereafter, the plants were grown in a greenhouse, and 28 days after treatment, the herbicidal effect was investigated according to the standards in Table 2. The results are shown in Table 3.
第２表
第３表
第３表つづき
試験例２（畑地土壌処理による除草効果試験）１２０ｃ
＋ａ″チツクポツトに畑地土壌を充填し、オオイヌタデ
（Ｐａ）、アオビユ（Ａｎ＋）、シロザ（Ｃｈ）、コゴ
メガヤッリ（Ｃｉ）の各種子を播種して覆土した。Table 2 Table 3 Table 3 continued Test example 2 (herbicidal effect test by field soil treatment) 120c
+a'' tick pots were filled with upland soil and covered with soil by sowing seeds of Japanese knotweed (Pa), Japanese knotweed (An+), whiteberry (Ch), and blackberry (Ci).
製剤例１に準じて調製した水和剤を水で希釈し、１０ア
ール当り有効成分がｌ ＯＯｇになる様に、１０アール
当り１００Ｑを小型噴霧器で土壌表面に均一に散布した
。その後、温室内で育成し、処理後２０日１に第２表の
基準に従って、除草効果を調査した。その結果を第４表
に示す。A wettable powder prepared according to Formulation Example 1 was diluted with water, and 100Q per 10 ares was uniformly sprayed on the soil surface using a small sprayer so that the active ingredient was 1 OOg per 10 ares. Thereafter, they were grown in a greenhouse, and 20 days after treatment, the herbicidal effect was investigated according to the standards in Table 2. The results are shown in Table 4.
第４表
第４表つづき
試験例３（畑地茎葉処理による除葦効果試験）１２０ｃ
ｍ″プラスチックポットに畑地土壌を充填し、オオイヌ
タデ（ＰＯ）、アオビユ（Ａｍ）、シロザ（Ｃｈ）、コ
ゴメガヤツリ（Ｃ１）の各種子を播種し覆土した。温室
内で２週間育成後、製剤例】に準じて調製した水和剤を
水に希釈し、１０アール当り有効成分がｉ ００ｇにな
る様に、１０アール当り１００Ｑを小型噴霧器で植物体
の上方から全体に茎葉散布処理した。その後、温室内で
育成し、処理後１４日百計第２表の基準に従って、除草
効果を調査した。試験結果を第５表に示す。Table 4 Table 4 Continued Test Example 3 (Reed removal effect test by field soil stem and leaf treatment) 120c
m'' plastic pots were filled with upland soil, and seeds of Japanese knotweed (PO), Japanese violet (Am), white cherries (Ch), and cypress (C1) were sown and covered with soil. After growing in a greenhouse for two weeks, formulation example] The hydrating agent prepared according to the above method was diluted with water, and 100Q per 10 ares was sprayed on the foliage from the top of the plant using a small sprayer so that the active ingredient was 100 g per 10 ares.Then, the greenhouse The herbicidal effect was investigated 14 days after treatment according to the standards in Table 2. The test results are shown in Table 5.
なお、比較薬剤として以下に示す化合物を使用した。以
後の試験例においても同様である。In addition, the following compounds were used as comparative drugs. The same applies to subsequent test examples.
化合物（Ａ） （特開昭６２−１７４０５９号公報記載化合物）しり。Compound (A) (Compound described in JP-A-62-174059) Shiri.
（特開昭５４−５５７２９号公報記載化合物）記載化合
物）
第５表
試験例４ （畑地土壌処理における薬効・薬害試験）６
００ｃｍ’ブラスチッグポット各々に畑地土壌を充填し
、タイプＡとして棉（ＧＯ）、ヒエ（Ｅｃ）、ジョンソ
ングラス（ＳＯ）、オオイヌタデ（Ｐｏ）、アオビユ（
Ａｍ）、シロザ（Ｃｈ）、ノアサガオ（Ｉｐ）及びオナ
モミ（Ｘａ）を播種し、ハマスゲ（Ｃｒ）の塊茎を置床
して覆土した。また、タイプＢとして大豆（Ｇｌ）、ヒ
エ（Ｅｃ）、メヒシバ（Ｄｉ）、ジョンソングラス（Ｓ
ｏ）、オオイヌタデ（Ｐａ）、アオビユ（Ａｍ）及びシ
ロザ（Ｃｈ）を播種し、ハマスゲ（Ｃｒ）の塊茎を置床
して覆土した。(Compounds described in JP-A No. 54-55729) Table 5 Test Example 4 (Medical efficacy/toxicity test in field soil treatment) 6
00cm' brass stig pots were each filled with upland soil, and type A cotton (GO), barnyard grass (Ec), johnson grass (SO), Japanese knotweed (Po), and blueberry (
Am), Shiroza (Ch), Noasagao (Ip), and Onamia (Xa) were sown, and tubers of Japanese sedge (Cr) were placed on the bed and covered with soil. Type B also includes soybean (Gl), barnyard grass (Ec), crabgrass (Di), and johnson grass (S).
o), Japanese knotweed (Pa), Japanese knotweed (Am), and white grass (Ch) were sown, and tubers of Japanese knotweed (Cr) were placed on the bed and covered with soil.
ポット底部より吸水させた後、製剤例１に準じて調製し
た水和剤の所定有効成分量を１ｏアール当り１ｏｏｇの
水で希釈し、小型噴霧器で土壌表面に散布処理した。そ
の後温室内で育成し、処理後２０日百計第２表の基準に
従って、除草効果及び薬害を調査した。その結果を第６
−Ａ表及び第６−Ｂ表に示す。After absorbing water from the bottom of the pot, a predetermined amount of the active ingredient of the wettable powder prepared according to Formulation Example 1 was diluted with 10g of water per 10are, and the mixture was sprayed onto the soil surface using a small sprayer. Thereafter, they were grown in a greenhouse, and 20 days after treatment, their herbicidal effects and phytotoxicity were investigated according to the standards in Table 2. The result is the 6th
- Shown in Table A and Table 6-B.
試験例５（畑地茎葉処理による薬効・薬害試験）６００
ｃｍ＋’プラスチックポット各々に畑地土壌を充填し、
棉（ＧＯ）、ヒエ（Ｅｃ）、ジョンソングラス（Ｓｏ）
、オオイヌタデ（Ｐｏ）、アオビユ（Ａｍ）、シロザ（
Ｃｈ）、ノアサガオ（Ｉｐ）及びオナモミ（Ｘａ）を播
種し、ハマスゲ（Ｃｒ）の塊茎を置床して覆土した。ボ
・ソト底部より吸水させ、温室内で２週間育成後、製剤
例１に準じて調製した水和剤をの所定有効成分量を１０
アール当り１００ρの水で希釈し、小型噴霧器で植物体
の上方から全体に茎葉散布処理した。Test Example 5 (Medicinal efficacy/phytotoxicity test by field soil, stem, and leaf treatment) 600
Fill each cm+' plastic pot with upland soil,
Cotton (GO), Japanese barnyard grass (Ec), Johnson grass (So)
, Japanese knotweed (Po), Japanese bluetail (Am), and silverfish (
Ch), Noasagao (Ip), and Onamia (Xa) were sown, and tubers of Red-bellied lily (Cr) were placed on the bed and covered with soil. After absorbing water from the bottom of Bo Soto and growing it in a greenhouse for 2 weeks, a predetermined amount of active ingredient in a hydrating powder prepared according to Formulation Example 1 was added to 10
It was diluted with 100 ρ of water per area and sprayed on the entire plant from above using a small sprayer.
その後、再び温室内で育成し、処理後１４日百計第２表
の基準に従って、除草効果を調査した。その結果を第７
表に示す。Thereafter, the plants were grown again in the greenhouse, and the herbicidal effect was investigated 14 days after treatment according to the standards in Table 2. The results are shown in the 7th section.
Shown in the table.
試験例６ （水田土壌処理による作物選択性試験）１
／ ５０００ ａワグネルポットに水田土壌を充填し、
入水、代掻後、ヒエ（Ｅｃ）、コナギ（Ｍｏ）及びホタ
ルイ（Ｓｃ）の種子を０．５ｃｍの深さに播種し、萌芽
したウリカワ（Ｓａ）の塊茎をポット当り２個体づつ深
度２ｃｍに埋没させ、更に２．５葉期の水稲（Ｏｒ）を
移植深度２ｃｍで、２本移植して水深３ｃｍに湛水した
。翌日、製刑例１に準じて調製した水和剤の所定有効成
分量を水で希釈し、水面に滴下処理した。その後、温室
内で育成し、処理後２８日目に第２表の基準に従い、除
草効果及び薬害を調査した。その結果を第８表に示す。Test Example 6 (Crop selectivity test by paddy soil treatment) 1
/ 5000a Wagner pot filled with paddy soil,
After watering and puddling, seeds of Japanese barnyard grass (Ec), Japanese mulberry (Mo), and firefly (Sc) were sown at a depth of 0.5 cm, and the sprouted tubers of Urikawa (Sa) were sown at a depth of 2 cm, two individuals per pot. After burying the soil, two paddy rice plants (Or) at the 2.5-leaf stage were transplanted to a depth of 2 cm and submerged in water to a depth of 3 cm. The next day, a predetermined amount of the active ingredient of a wettable powder prepared according to Preparation Example 1 was diluted with water and dropped onto the water surface. Thereafter, they were grown in a greenhouse, and 28 days after treatment, the herbicidal effect and phytotoxicity were investigated according to the standards in Table 2. The results are shown in Table 8.
第８表
イハラケミカル工業株式会社
手続補正書（白側
平成２年１１月２０日
１、事件の表示
平成２年特許願第２２９２５９号
２、発明の名称
ピリミジン誘導体及び除草剤
３、補正をする者
事件との関係 特許出願人
住所 東京都台東区池之端１丁目４番２６号電話０３（
８２２）５１７８
４、補正命令の日付 自発
５、補正の対象
（１）明細書第２２頁下から９行目の
「チックポット」を「プラスチックポット」と訂正しま
す。Table 8 Ihara Chemical Industry Co., Ltd. Procedural Amendment (white side November 20, 1990 1, Description of the case 1990 Patent Application No. 229259 2, Name of the invention pyrimidine derivatives and herbicides 3, Person making the amendment) Relationship to the incident Patent applicant address: 1-4-26 Ikenohata, Taito-ku, Tokyo Telephone: 03 (
822) 5178 4. Date of amendment order Voluntary action 5. Subject of amendment (1) "Tick pot" in line 9 from the bottom of page 22 of the specification is corrected to "plastic pot."
（２）明細書第２２頁下６−Ｂ表中の 「 以上(2) In Table 6-B on page 22 of the specification " that's all
Claims (2)
ルキルチオ基、ハロアルキル基、ハロゲン原子、アシル
基、アルコキシカルボニル基、アルコキシアルコキシ基
、フェノキシアルコキシ基、アルコキシアルキルチオ基
、アルキル基またはハロゲン原子で置換されてもよいフ
ェニルチオ基、ピロール基またはシクロアルキルアルコ
キシ基を示し、Ｒは水素原子、アルキル基またはベンジ
ル基を示し、ｎは１または２の整数を示す。但し、Ｘが
アルキル基またはハロゲン原子を示すときｎは２を示す
。）で表されるピリミジン誘導体及びその塩。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, A phenoxyalkoxy group, an alkoxyalkylthio group, an alkyl group, or a phenylthio group optionally substituted with a halogen atom, a pyrrole group, or a cycloalkylalkoxy group, R represents a hydrogen atom, an alkyl group, or a benzyl group, and n is 1 or 2 (wherein, when X represents an alkyl group or a halogen atom, n represents 2.) and salts thereof.
ルキルチオ基、ハロアルキル基、ハロゲン原子、アシル
基、アルコキシカルボニル基、アルコキシアルコキシ基
、フェノキシアルコキシ基、アルコキシアルキルチオ基
、アルキル基またはハロゲン原子で置換されてもよいフ
ェニルチオ基、ピロール基またはシクロアルキルアルコ
キシ基を示し、Ｒは水素原子、アルキル基またはベンジ
ル基を示し、ｎは１または２の整数を示す。但し、Ｘが
アルキル基またはハロゲン原子を示すときｎは２を示す
。）で表されるピリミジン誘導体及びその塩を有効成分
として含有する除草剤。(2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, A phenoxyalkoxy group, an alkoxyalkylthio group, an alkyl group, or a phenylthio group optionally substituted with a halogen atom, a pyrrole group, or a cycloalkylalkoxy group, R represents a hydrogen atom, an alkyl group, or a benzyl group, and n is 1 or 2 (wherein, when X represents an alkyl group or a halogen atom, n represents 2.) A herbicide containing a pyrimidine derivative and its salt as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22925990A JPH04108777A (en) | 1990-08-30 | 1990-08-30 | Pyrimidine derivative and herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22925990A JPH04108777A (en) | 1990-08-30 | 1990-08-30 | Pyrimidine derivative and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04108777A true JPH04108777A (en) | 1992-04-09 |
Family
ID=16889312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22925990A Pending JPH04108777A (en) | 1990-08-30 | 1990-08-30 | Pyrimidine derivative and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04108777A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994017059A1 (en) * | 1993-01-29 | 1994-08-04 | Nippon Soda Co., Ltd. | Heterocyclic derivative |
| WO2015089003A1 (en) * | 2013-12-10 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
| US10131652B2 (en) | 2014-01-16 | 2018-11-20 | E. I. Du Pont De Nemours And Company | Pyrimidinyloxy benzene derivatives as herbicides |
| US10485235B2 (en) | 2015-07-13 | 2019-11-26 | Fmc Corporation | Aryloxypyrimidinyl ethers as herbicides |
| US11006631B2 (en) | 2015-03-18 | 2021-05-18 | Fmc Corporation | Substituted pyrimidinyloxy pyridine derivatives as herbicides |
| US11053204B2 (en) | 2015-06-05 | 2021-07-06 | Fmc Corporation | Pyrimidinyloxy benzene derivatives as herbicides |
| US11427549B2 (en) | 2017-05-02 | 2022-08-30 | Fmc Corporation | Pyrimidinyloxy benzo-fused compounds as herbicides |
-
1990
- 1990-08-30 JP JP22925990A patent/JPH04108777A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994017059A1 (en) * | 1993-01-29 | 1994-08-04 | Nippon Soda Co., Ltd. | Heterocyclic derivative |
| WO2015089003A1 (en) * | 2013-12-10 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
| US9695155B2 (en) | 2013-12-10 | 2017-07-04 | E I Du Pont De Nemours And Company | Herbicidal substituted pyrimidinyloxy benzene compounds |
| RU2703460C1 (en) * | 2013-12-10 | 2019-10-17 | ЭфЭмСи Корпорейшн | Herbicidal substituted pyrimidinyloxybenzole compounds |
| US10131652B2 (en) | 2014-01-16 | 2018-11-20 | E. I. Du Pont De Nemours And Company | Pyrimidinyloxy benzene derivatives as herbicides |
| US10654840B2 (en) | 2014-01-16 | 2020-05-19 | Fmc Corporation | Pyrimidinyloxy benzene derivatives as herbicides |
| US11447476B2 (en) | 2014-01-16 | 2022-09-20 | Fmc Corporation | Pyrimidinyloxy benzene derivatives as herbicides |
| US11006631B2 (en) | 2015-03-18 | 2021-05-18 | Fmc Corporation | Substituted pyrimidinyloxy pyridine derivatives as herbicides |
| US11053204B2 (en) | 2015-06-05 | 2021-07-06 | Fmc Corporation | Pyrimidinyloxy benzene derivatives as herbicides |
| US10485235B2 (en) | 2015-07-13 | 2019-11-26 | Fmc Corporation | Aryloxypyrimidinyl ethers as herbicides |
| US11427549B2 (en) | 2017-05-02 | 2022-08-30 | Fmc Corporation | Pyrimidinyloxy benzo-fused compounds as herbicides |
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