JPS63258462A - 2-phenoxypyrimidine derivative and herbicide - Google Patents
2-phenoxypyrimidine derivative and herbicideInfo
- Publication number
- JPS63258462A JPS63258462A JP9178487A JP9178487A JPS63258462A JP S63258462 A JPS63258462 A JP S63258462A JP 9178487 A JP9178487 A JP 9178487A JP 9178487 A JP9178487 A JP 9178487A JP S63258462 A JPS63258462 A JP S63258462A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- herbicide
- grass
- 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 17
- 239000004009 herbicide Substances 0.000 title claims abstract description 14
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000004252 dithioacetals Chemical class 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 32
- 239000002904 solvent Substances 0.000 abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 3
- 240000002439 Sorghum halepense Species 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 244000075634 Cyperus rotundus Species 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 235000005010 Scirpus paludosus Nutrition 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 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
- 241000196324 Embryophyta Species 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 244000025254 Cannabis sativa Species 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 benzylsulfonyl group Chemical group 0.000 description 9
- 241000218691 Cupressaceae Species 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 240000001341 Reynoutria japonica Species 0.000 description 5
- 235000018167 Reynoutria japonica Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000000887 hydrating effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001311476 Abies veitchii Species 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000254032 Acrididae 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
- 241000480037 Argyrosomus japonicus Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001585533 Callitris endlicheri Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000722731 Carex Species 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000234653 Cyperus 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
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 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
- 240000003173 Drymaria cordata Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000000486 Lepidium draba Species 0.000 description 1
- 235000000391 Lepidium draba Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 240000006959 Melochia corchorifolia Species 0.000 description 1
- 241000878007 Miscanthus Species 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- 241001600434 Plectroglyphidodon lacrymatus Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 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
- 208000003251 Pruritus Diseases 0.000 description 1
- 240000007807 Sisymbrium officinale Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 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
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003905 agrochemical 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
- 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011835 investigation Methods 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
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 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２−フェノキシピリミジン誘導体及び
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 2-phenoxypyrimidine derivative and a herbicide containing the same as an active ingredient that can be applied to paddy fields, fields, non-agricultural land, etc. .
（従来の技術）
２−フェノキシピリミジン誘導体が除草作用を有するこ
とは、（１）アグリ力ルチーラル・アンド・バイオロジ
カル・ケミストリ（Ａｇｒ、Ｂｉｏｌ、Ｃｈｅｍ、）
５０巻、９号、８９６頁（１９６６年） 、 （２１特
開昭５４−５５７２９−号公報明細書（３）％開昭５４
−１１７４８６号公報明細書及び（４）特公昭 ４２−
９４７４号公報明細１等に記載されている。(Prior art) The fact that 2-phenoxypyrimidine derivatives have herbicidal activity is known from (1) Agricultural and Biological Chemistry (Agr, Biol, Chem,)
Volume 50, No. 9, Page 896 (1966), (21 JP-A-54-55729- Specification (3)%
-117486 publication specification and (4) Japanese Patent Publication No. 42-
It is described in Publication No. 9474, Specification 1, etc.
（発明が解決しようとする問題点）
しかしながら、これら公報明細書及び文献に記載された
化合物の一年生雑草に対する防除効果は不十分であり、
しかも多年生雑草に対しては殆ど活性を示さないという
欠点を有している。(Problems to be Solved by the Invention) However, the control effects of the compounds described in these patent specifications and literature on annual weeds are insufficient;
Moreover, it has the disadvantage of showing almost no activity against perennial weeds.
本発明者らは、２−フェノキシピリミジン系化合物につ
いて除草活性の優れた化合物の開発を目的に鋭意研究し
た結果、ピリミジン環及びベンゼン環上の特定の位置に
置換基を導入した本願発明化合物が一年生雑草はもとよ
り多年生雑草、特に、ハマスゲ及びジョンソングラスに
対して優れた除草効果を示すとともに、作物に対する安
全性が極めて高いということを見い出し、本発明を完成
した。As a result of intensive research aimed at developing 2-phenoxypyrimidine compounds with excellent herbicidal activity, the present inventors discovered that the present invention compound with substituents introduced into specific positions on the pyrimidine ring and benzene ring has a one-year lifespan. The present invention was completed based on the discovery that the present invention exhibits an excellent herbicidal effect on not only weeds but also perennial weeds, especially mulberry grass and johnson grass, and is extremely safe for crops.
（問題点を解決する為の手段）
本発明の２−フェノキシピリミジン誘導体は一般式
〔式中、Ｒ１は水素原子、低級アルキル基、またはベン
ジル基を示す。）を示し、Ｘはアセチレン基、ピロール
基、ジチオアセタール基、または基２を示す。〕を示す
。〕にて表される０前記一般式（１）にて表される本発
明化合物を第１表に例示する。(Means for Solving the Problems) The 2-phenoxypyrimidine derivative of the present invention has the general formula [wherein R1 represents a hydrogen atom, a lower alkyl group, or a benzyl group]. ), and X represents an acetylene group, a pyrrole group, a dithioacetal group, or a group 2. ]. ] The compounds of the present invention represented by the above general formula (1) are illustrated in Table 1.
尚、化合物番号は以後の記載において参照される。In addition, the compound number will be referred to in the following description.
〇
第１表
４一
本発明化合物は下記の方法に従って製造することができ
るが、これらの方法に限定されるものではない。〇Table 1 41 The compounds of the present invention can be produced according to the following methods, but are not limited to these methods.
（Ａ法）
（式中、Ｒ２はハロゲン原子、アルキルスルホニル基、
ペンシルスルホニル基、または置換ベンジルスルホニル
基を示しＲ１及びＸは前記と同じ意味を示す。）
本発明化合物の内、式〔６〕で示される化合物は式〔１
〕で示される化合物と式〔２〕で示されるピリミジン化
合物とを塩基の存在下、好ましくは溶媒中で室温ないし
溶媒の沸点の温度範囲で１〜２４時間反応させることに
より製造することができる。(Method A) (wherein R2 is a halogen atom, an alkylsulfonyl group,
It represents a pencilsulfonyl group or a substituted benzylsulfonyl group, and R1 and X have the same meanings as above. ) Among the compounds of the present invention, the compound represented by formula [6] is represented by formula [1]
] and a pyrimidine compound represented by formula [2] in the presence of a base, preferably in a solvent at a temperature ranging from room temperature to the boiling point of the solvent for 1 to 24 hours.
無溶媒下で反応を行う場合は塩基として、無水炭酸カリ
ウムのようなアルカリ金属の炭酸塩等を使用して１２０
〜１６０°Ｃの温度範囲内で反応させることもできる。When carrying out the reaction without a solvent, an alkali metal carbonate such as anhydrous potassium carbonate is used as a base.
It is also possible to carry out the reaction within a temperature range of -160°C.
ここに使用される溶媒としては、例えば、ベンゼン、ト
ルエン、キシレン等の炭化水素系溶媒、塩化メチレン、
クロロホルム等のハロゲン化炭化水素系溶媒、メタノー
ル、エタノール、イソプロパツール等のアルコール系溶
媒、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−ジオキサン等のエーテル系溶媒、
アセトン、メチルエチルケトン等のケトン系溶媒、酢酸
メチル、酢酸エチル等のエステル系溶媒、ジメチルホル
ムアミド、ジメチルアセトアミド、ジメチルスルホキシ
ド等の非プロトン性極性溶媒及びアセトニトリル、水等
が挙げられる。また塩基としては、金属ナトリウム、金
属カリウム等のアルカリ金属類、水素化ナトリウム、水
素化カリウム、水素化カルシウム等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、炭酸水系ナトリウム、炭酸水素カリウム等
の炭酸塩類、水酸化ナトリウム、水酸化カリウム等の水
酸化金属類が挙げられる。Examples of the solvent used here include hydrocarbon solvents such as benzene, toluene, and xylene, methylene chloride,
Halogenated hydrocarbon solvents such as chloroform, alcohol solvents such as methanol, ethanol, and isopropanol, ether solvents such as ethyl ether, isopropyl ether, tetrahydrofuran, and 1,4-dioxane,
Examples include ketone solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide, acetonitrile, and water. 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 carbonated water. Examples include carbonates such as sodium and potassium hydrogen carbonate, and metal hydroxides such as sodium hydroxide and potassium hydroxide.
（Ｂ法）
−（４） ［５）〔６〕
（式中、ＲＢは低級アルキル基、またはベンジル基を示
し、Ｍはアルカリ金属、またはアルカリ土類金属を示し
、Ｘは前記と同じ意味を示す。）式〔６〕で示される本
発明化合物は、式〔４〕で示される化合物を塩基の存在
下、極性溶媒、水、または極性溶媒と水との混合溶媒中
、室温ないし溶媒の沸点の温度範囲で０．５〜６６時間
反応させ、７一
式〔５〕で示される化合物を製造した後、この化合物を
酸析することによって製造することができる。(Method B) -(4) [5) [6] (In the formula, RB represents a lower alkyl group or a benzyl group, M represents an alkali metal or an alkaline earth metal, and X has the same meaning as above. ) The compound of the present invention represented by formula [6] can be prepared by mixing the compound represented by formula [4] in the presence of a base in a polar solvent, water, or a mixed solvent of a polar solvent and water at room temperature or at the boiling point of the solvent. It can be produced by reacting at a temperature range of 0.5 to 66 hours to produce a compound represented by formula 7 [5], and then precipitating this compound with acid.
ここに使用される溶媒としては、例えばメタノール、エ
タノール、イソプロパツール等のアルコール系溶媒、ア
セトン、メチルエチルケトン等のケトン系溶媒等が挙げ
られる。また、塩基としては、例えば炭酸ナトリウム、
炭酸カリウム、炭酸カルシウム、炭酸水素ナトリウム、
炭酸水素カリウム等の炭酸塩類、水酸化ナトリウム、水
酸化カリウム等の水酸化金属類が挙げられる。Examples of the solvent used here include alcohol solvents such as methanol, ethanol, and isopropanol, and ketone solvents such as acetone and methyl ethyl ketone. In addition, as a base, for example, sodium carbonate,
potassium carbonate, calcium carbonate, sodium bicarbonate,
Examples include carbonates such as potassium hydrogen carbonate, and metal hydroxides such as sodium hydroxide and potassium hydroxide.
また、〔４〕においてＲ４がベンジル基を示す場合は、
水素による接触還元法により式〔６〕を製造することも
できる。Furthermore, when R4 in [4] represents a benzyl group,
Formula [6] can also be produced by a catalytic reduction method using hydrogen.
次に実施例を挙げて説明する。Next, an example will be given and explained.
実施例１
２−Ｃ４，６−シメトキシビリジンー２−イル）オキシ
−６−ピロリル安息香酸ベンジルの合成（化合物７）
６−ピロリルサリチル酸ベンジル（４，２ｙ−）、４．
６−シメトキシー２−メチルスルホニルピリミジン（３
，４ｊ？）及び炭酸水素カリウム（１，７ｙ−）をジメ
チルホルムアミド（２０ｍ）に懸濁後、１００〜１１０
℃で１時間加熱攪拌した。放冷後、反応液を水にあけ、
酢酸エチルで抽出した。抽出液は水洗、乾燥後溶剤を減
圧下に留去し、得られた残渣をシリカゲルカラムクロマ
トグラフィーにより精製し、標記化合物を白色無定形個
体（３，３ｙ−）として得た。Example 1 Synthesis of benzyl 2-C4,6-cymethoxypyridin-2-yl)oxy-6-pyrrolylbenzoate (compound 7) Benzyl 6-pyrrolylsalicylate (4,2y-), 4.
6-Simethoxy2-methylsulfonylpyrimidine (3
,4j? ) and potassium hydrogen carbonate (1,7y-) in dimethylformamide (20m), 100-110
The mixture was heated and stirred at ℃ for 1 hour. After cooling, the reaction solution was poured into water.
Extracted with ethyl acetate. After washing the extract with water and drying, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound as a white amorphous solid (3,3y-).
（融点１１１〜１１６℃）
実施例２
２−Ｃ４，６−シメトキシピリジンー２−イル）オキシ
−６−ピロリル安息香酸の合成（化合物８）１０多パラ
ジウムチヤコール（０，５，＠）、メチルアルコール（
１００ｍｔ）、酢酸エチル（５０祷）及び酢酸（２０膨
）を懸濁後、２− （４，６−シメトキシピリジンー２
−イル）オキシ−６−ピロリル安息香酸ベンジル（２，
３！１Ｉ−）を加え、常圧下接触還元を行った。水素の
吸収が止んだところで触媒を濾別し、濾液を濃縮した。(Melting point 111-116°C) Example 2 Synthesis of 2-C4,6-simethoxypyridin-2-yl)oxy-6-pyrrolylbenzoic acid (Compound 8) 10 polypalladium thiacol (0,5,@), Methyl alcohol (
After suspending ethyl acetate (50 mt) and acetic acid (20 mt), 2-(4,6-cymethoxypyridine-2
-yl)oxy-6-pyrrolylbenzoate benzyl (2,
3!1I-) was added to perform catalytic reduction under normal pressure. When hydrogen absorption ceased, the catalyst was filtered off, and the filtrate was concentrated.
残渣を酢酸エチルに溶解し、水洗、乾燥後溶剤を減圧下
に留去し、標記化合物を白色結晶（ｉ、 １ 、Ｐ ）
として得た〇（融点１２５〜１２７℃）
本発明の除草剤は１本発明化合物である２−フェノキシ
ピリミジン誘導体を含んでなる。The residue was dissolved in ethyl acetate, washed with water, dried, and then the solvent was distilled off under reduced pressure to give the title compound as white crystals (i, 1, P).
The herbicide of the present invention contains a 2-phenoxypyrimidine derivative, which is a compound of the present invention.
本発明化合物を除草剤として使用する場合、化合物のめ
、またはこれに農薬の製剤化に際し一般的に用いられる
、担体、界面活性剤、分散剤、補助剤等を配合して、水
和剤、粒剤、乳剤または粉剤等の各種形態に製剤して使
用することができる。When the compound of the present invention is used as a herbicide, a carrier, a surfactant, a dispersant, an auxiliary agent, etc., which are commonly used in the formulation of agricultural chemicals, are blended with the compound or with the compound to form a hydrating agent. It can be formulated and used in various forms such as granules, emulsions, or powders.
製剤化に際し２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、バーミキーライト、消石
灰、珪砂、硫安、尿素等の囲体担体、イソプロピルアル
コール、キシレン、シクロヘキサン、メチルナフタレン
等の液体担体等が挙げられる。界面活性剤及び分散剤と
しては、例えば、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、リグニンスルボン酸塩、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
アルギ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１／−ト等が挙げられる。補助剤として
は、例えば、カルボキシメチルセルロース、ポリエチレ
ングリコール、アラビアゴム等が挙げられる。使用に際
しては、適当な濃度に希釈して散布するか、または直接
施用する。Examples of carriers used in formulation 2 include dicrite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermicelliite, slaked lime, silica sand, ammonium sulfate, urea and other surrounding carriers, isopropyl alcohol, Examples include liquid carriers such as xylene, cyclohexane, and methylnaphthalene. Examples of surfactants and dispersants include alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene argylaryl ether, polyoxyethylene sorbitan monoalkyl 1/ - etc. Examples of the adjuvant include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. When using it, it can be diluted to an appropriate concentration and sprayed, or it can be applied directly.
また、本発明の除草剤は他の除草剤と混合して使用する
事もできる。Moreover, the herbicide of the present invention can also be used in combination with other herbicides.
本発明除草剤は、水田において、雑草の発芽前または発
芽後に湛水土壌処理または茎葉処理することにより、水
田に発生する各種の雑草を防除することができる。また
、畑地においても、雑草の発芽前または発芽後に土壌処
理、または茎葉処理することにより、畑地に発生する各
種の雑草を防除することができる。The herbicide of the present invention can control various weeds that occur in rice fields by treating the soil with water or treating the foliage before or after the germination of the weeds. In addition, various weeds occurring in fields can be controlled by treating the soil or treating the foliage before or after the germination of the weeds.
本発明除草剤は、有効成分で１０アール当たり０、１
ｆ〜１に９施用する。また植物茎葉に散布する場合はｊ
ｐｐｍ〜ｊ ００００ ｐｐｍに希釈して施用する。The herbicide of the present invention has an active ingredient of 0 to 1 per 10 ares.
9 applications to f~1. Also, when spraying on plant stems and leaves,
It is applied diluted to between ppm and j 0000 ppm.
次に、本発明除草剤の実施例を挙げるが、本発明はこの
範囲に限定されるものではない。Next, Examples of the herbicide of the present invention will be given, but the present invention is not limited to this range.
尚、実施例中に記載のφは重量百分率を示す。In addition, φ described in the examples indicates weight percentage.
実施例３ （水和剤）
化合物（７） １０ ％、エマルゲン８１０（花王石鹸
株式会社登録商標）１１．ｓｇ＆、デモールＮ（花王石
鹸株式会社登録商標） ０．５１＋、クニライト（クニ
ミネ工業株式会社登録商標）２０１ ２０’％、ジ−ク
ライト（ジ−クライト株式会社登録商標）ＣＡ６９％を
均一に混合粉砕して水和剤とした。Example 3 (Wettable powder) Compound (7) 10%, Emulgen 810 (registered trademark of Kao Soap Co., Ltd.) 11. sg&, Demol N (registered trademark of Kao Soap Co., Ltd.) 0.51+, Kunilite (registered trademark of Kunimine Industries Co., Ltd.) 201 20'%, and Zikrite (registered trademark of Zikrite Co., Ltd.) CA69% are uniformly mixed and ground. It was used as a hydrating agent.
実施例４ （乳剤）
化合物（１１３０９６，シクロへキサノン２０チ、ポリ
オキシエチレンアルキルアリールエーテル１１チ、アル
キルベンゼンスルホン酸カルシウム４９＆、及びメチル
ナフタリン６５チを均一に溶解して乳剤とした。Example 4 (Emulsion) Compounds (113096, 20% cyclohexanone, 11% polyoxyethylene alkylaryl ether, 49% calcium alkylbenzenesulfonate, and 65% methylnaphthalene) were uniformly dissolved to prepare an emulsion.
実施例５ （粒剤）
化合物（９） ５ ％、ラウリルアルコール硫酸エステ
ルのナトリウム塩２％、リグニンスルホン酸ナトリウム
５％、カルボキシメチルセルロース２チ、及びクレー８
６％を均一に混合粉砕する。この混合物１００重量部に
水２０重量部を加えて練合し押出式造粒機を用いて１４
〜３２メツシユの粒状に加工したのち、乾燥して粒剤と
した。Example 5 (granules) Compound (9) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium lignin sulfonate 5%, carboxymethyl cellulose 2, and clay 8
Mix and grind 6% uniformly. Add 20 parts by weight of water to 100 parts by weight of this mixture, knead it, and use an extrusion type granulator for 14 hours.
After processing into granules of ~32 meshes, they were dried to form granules.
実施例６ （粉剤）
化合物（８）２％、珪藻±５多、及びクレー９３％を均
一に混合粉砕して粉剤とした。Example 6 (Powder) 2% of compound (8), ±5 diatoms, and 93% of clay were uniformly mixed and ground to obtain a powder.
（発明の効果）
本発明の化合物及び除草剤は、水田に発生するタイヌビ
エ、タマガヤツリ、コナギ、ホタルイ、ヘラオモダカ等
の一年生雑草及びミズガヤツリ、ウリカワ、クログワイ
等の多年生雑草を有効に防除することができる。また、
畑地に発生するヒエ、メヒシバ、オヒシバ、エノコログ
サ、スズメノテッポウ、スズメノカタビラ、カラスムギ
、イタリアンライグラス、オオイヌタデ、アオビユ、シ
ロザ、アカザ、イチビ、アメリカキンゴジカ、エビスグ
サ、ハコベ、アサガオ、オナモミ、コゴメガヤツリ、メ
リケンニクキビ、イッチグラス、ウマノチャヒキ、ソバ
カズラ、ノハラガラシ、アメリカセンダングサ等の一年
生雑草及びハマスゲ、ジョンソングラス、キョウギシバ
、シバムギ等の多年生雑草をも有効に防除することがで
きる。一方、作物に対する安全性は極めて高い。更に、
本発明へ 化合物は、前述の文献記載の公知化合物と
比較しても、−手生雑草はもとより、ハマスゲ等の多年
生雑草に対する除草効果が優れているという特徴を有す
るものである。(Effects of the Invention) The compounds and herbicides of the present invention can effectively control annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, and perennial weeds such as Japanese cypress, Japanese cypress, and black cypress. Also,
Japanese barnyard grass, crabgrass, black-and-white grass, foxtail grass, sycamore, sycamore, oat, Italian ryegrass, Japanese knotweed, blueberry, whiteweed, redweed, Japanese croaker, golden deer, yellowtail grass, chickweed, morning glory, Japanese fir, Japanese snail, Japanese snail, and itch. It is also possible to effectively control annual weeds such as grass, grass, buckwheat, wild mustard, and helium, as well as perennial weeds such as common grass, johnson grass, silver grass, and grasshopper. On the other hand, it is extremely safe for crops. Furthermore,
Toward the Present Invention The compound is characterized in that it has an excellent herbicidal effect on perennial weeds such as sedges as well as hand weeds, even when compared with the known compounds described in the above-mentioned literature.
次に、本発明除草剤の奏する効果を試験例を挙げて説明
する。Next, the effects of the herbicide of the present invention will be explained using test examples.
試験例１ （茎葉処理）
土壌を充填した１００ｍポットにヒエ、メヒシバ、オオ
イヌタデ、アオビユ、シロザ及びコゴメガヤツリの各種
子を播種し、０．５〜１ｃｒ／Ｌに覆土した。ポットは
２０〜２５℃のガラス室内で２週間育成後に実施例乙に
準じて調製した水和剤を有効成分で１０アール当り４０
０ノとなるよう１０アール当り１００ｔの水で希釈し、
茎葉表面に散布した。調査は薬剤処理後１４日１に第２
表の基準に従い行った。結果を第６表に指数で示した。Test Example 1 (Treatment of Stalks and Leaves) Seeds of Japanese barnyard grass, Japanese knotweed, Japanese knotweed, Japanese violet, white-tailed grass, and Japanese cypress were sown in a 100 m pot filled with soil, and covered with soil at a concentration of 0.5 to 1 cr/L. After growing the pot in a glass room at 20 to 25°C for two weeks, add a hydrating powder prepared according to Example B to the active ingredient at 40% per 10 ares.
Dilute with 100 tons of water per 10 are so that it becomes 0.
Sprayed on the surface of the leaves. The survey was carried out 1 and 2 times on the 14th day after drug treatment.
It was conducted according to the standards in the table. The results are shown in Table 6 as an index.
第２表 第６表 （注） ｔ 試験植物の略記号は下記の植物を表す。Table 2 Table 6 (note) t The abbreviations for test plants represent the following plants.
（他の表も同様である）
Ｅｃｈ； ヒエ （Ｅｃｈｉｎｏｃｈｌｏ
ａ ｃｒｕｓ−ｇａｌｉ）Ｄｉｇ ； メヒシバ
（Ｄｉｇｉｔａｒｉａ ａｄｓｃｅｎｄｅｎｓ）Ｐｏ
ｌ； オオイヌタデ （Ｐｏｌｙｇｏｎｕｍ ｎｏｄ
ｏｓｕｍ）Ａｍａ ； アオビユ （Ａｍａｒａｎ
ｔｈｕｓ ｒｅｔｒｏｆｌｅｘｕｓ）Ｃｈｅ ； シ
ロザ （Ｃｈｅｎｏｐｏｄｉｕｍ ａｌｂｕｍ）
Ｃｙｉ； コゴメガヤツリ （Ｃｙｐｅｒｕｓ １ｒ
ｉａ）２、比較化合物Ａ、Ｂ及びＣは下記の化合物を表
す。（他の表も同じである）
Ｃ％開昭−５４−５５７２９号公報記載）Ｉ
（％開昭−５４−５５７２９号公報記載）しに′Ｌ３
アグリカルチュラル・アンド・バイオロジカル・ケミス
トリ（Ａｇｒ、Ｂｉｏｌ、Ｃｈｅｍ、） ３０巻、９
号、８９６頁（１９６６年）記載
試験例２ （土壌処理）
土壌を充填した１ｏａｄボツトにヒエ、メヒシバ、オオ
イヌタデ、アオビユ、シロザ及びコゴメガヤツリの各種
子を播種し、０．５〜１ｃｆＩＬに覆土した。播種翌日
に実施例乙に準じて調製した水和剤を有効成分で１０ア
ール当り４００／となるよう１０アール当り１００ｔの
水で希釈し、土壌表面に散布した。薬剤処理２０日目に
第２表の基準に従い行った調査結果を第４表に指数で示
した。(The same applies to other tables) Ech; Millet (Echinochlo)
a crus-gali) Dig;
(Digitalia adscendens)Po
l; Polygonum nod
osum) Ama; Aobiyu (Amaran)
thus retroflexus) Che; Shiroza (Chenopodium album)
Cyi; Cyperus 1r
ia) 2. Comparative compounds A, B and C represent the following compounds. (Other tables are the same) Biol, Chem,) Volume 30, 9
No., p. 896 (1966) Test Example 2 (Soil treatment) Seeds of Japanese barnyard grass, Japanese knotweed, Japanese knotweed, Japanese violet, white-tailed grass, and Japanese cypress were sown in a 1-oad pot filled with soil, and the seeds were covered with soil to a depth of 0.5 to 1 cfIL. On the day after sowing, a hydrating agent prepared according to Example B was diluted with the active ingredient to a concentration of 400/10 ares with 100 tons of water per 10 ares, and was sprayed on the soil surface. The results of the investigation conducted on the 20th day of drug treatment according to the criteria in Table 2 are shown in Table 4 as an index.
第４表
試験例３ （多年生雑草に対する効果）土壌を充填した
６ ０ ｏｃ１１ｔボットにハマスゲの塊茎を覆土が０
．５〜１はの厚さになるように埋め込んだ。土壌処理で
は播種１日後に、実施例３に準じて調製した水相剤の所
定量を１０アール当り１００ｔの水で希釈し、土壌表面
に散布した。Table 4 Test Example 3 (Effect on perennial weeds) Covering the tubers of the common grass in a 60 oc11t bot filled with soil.
．． 5 to 1 were embedded to a thickness of . In the soil treatment, one day after sowing, a predetermined amount of the aqueous phase agent prepared according to Example 3 was diluted with 100 tons of water per 10 ares and sprayed on the soil surface.
また、茎葉処理ではポットを２０〜２５℃のガラス室内
で２週間育成した後に、実施例４に準じて調製した水和
剤の所定量を展着剤としてサーファクタントＷＫ ２０
００ ｐｐｍの濃度を含む１０アール当り１００ｔの水
で希釈し、茎葉表面に散布した。In addition, in the foliage treatment, after growing the pots in a glass room at 20 to 25°C for two weeks, a predetermined amount of a hydrating powder prepared according to Example 4 was used as a spreading agent and surfactant WK 20 was used.
The solution was diluted with 100 tons of water per 10 are containing a concentration of 0.00 ppm and sprayed on the surfaces of the leaves.
調査は、土壌処理は薬剤処理５０日目に、茎葉処理は２
１日目に行った。結果を第２表の基準に従い指数で第５
表に示した。The survey was conducted on the 50th day of chemical treatment for soil treatment, and on the 2nd day for foliage treatment.
I went on the first day. The results are indexed according to the criteria in Table 2.
Shown in the table.
第５表 （注） 比較化合物りは下記の化合物を表す。Table 5 (note) Comparative compounds represent the following compounds.
ｒr
Claims (2)
ンジル基を示す。）を示し、Ｘはアセチレン基、ピロー
ル基、ジチオアセタール基、または基 ▲数式、化学式、表等があります▼（式中、ｎは０、１
、また は２を示す。）を示す。〕にて表される２−フェノキシ
ピリミジン誘導体。(1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents a hydrogen atom, a lower alkyl group, or a benzyl group. ), and X is an acetylene group, pyrrole group, dithioacetal group, or group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, n is 0, 1
, or 2. ) is shown. ] A 2-phenoxypyrimidine derivative represented by:
ンジル基を示す。）を示し、Ｘはアセチレン基、ピロー
ル基、ジチオアセタール基、または基 ▲数式、化学式、表等があります▼（式中、ｎは０、１
、ま たは２を示す。）を示す。〕にて表される２−フェノキ
シピリミジン誘導体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, R^1 represents a hydrogen atom, a lower alkyl group, or a benzyl group. ), and X is an acetylene group, pyrrole group, dithioacetal group, or group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, n is 0, 1
, or 2. ) is shown. ] A herbicide containing a 2-phenoxypyrimidine derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9178487A JPS63258462A (en) | 1987-04-14 | 1987-04-14 | 2-phenoxypyrimidine derivative and herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9178487A JPS63258462A (en) | 1987-04-14 | 1987-04-14 | 2-phenoxypyrimidine derivative and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63258462A true JPS63258462A (en) | 1988-10-25 |
Family
ID=14036223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9178487A Pending JPS63258462A (en) | 1987-04-14 | 1987-04-14 | 2-phenoxypyrimidine derivative and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63258462A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5125957A (en) * | 1989-11-01 | 1992-06-30 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5129938A (en) * | 1990-07-26 | 1992-07-14 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5135563A (en) * | 1990-07-05 | 1992-08-04 | Sumitomo Chemical Company, Limited | Pyrimidine derivative |
| US5232897A (en) * | 1990-05-15 | 1993-08-03 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| US5298632A (en) * | 1990-05-15 | 1994-03-29 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| EP2486004B1 (en) * | 2009-10-09 | 2017-05-03 | Zafgen, Inc. | Sulphone compounds for use in the treatment of obesity |
-
1987
- 1987-04-14 JP JP9178487A patent/JPS63258462A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5125957A (en) * | 1989-11-01 | 1992-06-30 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5300640A (en) * | 1989-11-01 | 1994-04-05 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives, their production and use |
| US5232897A (en) * | 1990-05-15 | 1993-08-03 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| US5298632A (en) * | 1990-05-15 | 1994-03-29 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| US5455355A (en) * | 1990-05-15 | 1995-10-03 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5135563A (en) * | 1990-07-05 | 1992-08-04 | Sumitomo Chemical Company, Limited | Pyrimidine derivative |
| US5129938A (en) * | 1990-07-26 | 1992-07-14 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| EP2486004B1 (en) * | 2009-10-09 | 2017-05-03 | Zafgen, Inc. | Sulphone compounds for use in the treatment of obesity |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5324854A (en) | Intermediate isocyana to benzenesulfonamide compounds | |
| JPS63115870A (en) | 2-phenoxypyrimidine derivative and herbicide | |
| JPH01250365A (en) | Pyrimidine derivative and herbicide | |
| JPS63258463A (en) | 2-phenoxypyrimidine derivative and herbicide | |
| JPS595181A (en) | N-heterocyclosulfonyl-n'-pyrimidinylurea and n-heterocyclosulfonyl-n'-triazinylurea, manufacture and plant growth regulant | |
| JPH04103574A (en) | Pyrimidine derivative and herbicide | |
| JPS63264465A (en) | Triazine derivative, production thereof and herbicide comprising said derivative as active ingredient | |
| JP2000063360A (en) | Trifluoromethanesulfonylanilide derivative, its production and herbicide with the same as active ingredient | |
| JPH01250378A (en) | Pyrimidine derivative and herbicide | |
| JPS6351379A (en) | Triazine derivative, production thereof and herbicide containing said derivative as active ingredient | |
| JPS63258462A (en) | 2-phenoxypyrimidine derivative and herbicide | |
| JPS63258467A (en) | 2-phenoxytriazine derivative and herbicide | |
| JPH04145081A (en) | Pyrazolecarboxylic acid derivative and herbicide | |
| JPH01301668A (en) | Mandelic acid derivative and herbicide | |
| JPH0256469A (en) | Pyridazinone derivative and herbicide | |
| JPH0285262A (en) | Herbicide and novel alkanoic acid derivative useful as active component of same herbicide | |
| SU1709910A3 (en) | Method for the synthesis of sulphonylurea bicyclic derivative | |
| JP2530188B2 (en) | 2-phenoxypyrimidine derivatives and herbicides | |
| JPS60149571A (en) | 2-(substituted phenyl)-1,2,4-triazolin-3-one and herbicide containing same as active constituent | |
| JPS63258461A (en) | 2-phenoxypyrimidine derivative and herbicide | |
| JP2730022B2 (en) | 3-Alkoxybutylyl imidazole derivatives, their production and herbicides | |
| JP2530156B2 (en) | 2-Phenoxypyrimidine derivative and herbicide | |
| JPH01250366A (en) | 2-phenoxypyrimidine derivative and herbicide | |
| JPH01250363A (en) | 4-benzylaminopyrimidine derivative and herbicide | |
| JPH01121290A (en) | Tetrahydrotriazopyridazine-3-thiox-1(2h)-one derivative and herbicide |