JPH0331266A - Pyrimidine derivative and herbicide - Google Patents
Pyrimidine derivative and herbicideInfo
- Publication number
- JPH0331266A JPH0331266A JP16494289A JP16494289A JPH0331266A JP H0331266 A JPH0331266 A JP H0331266A JP 16494289 A JP16494289 A JP 16494289A JP 16494289 A JP16494289 A JP 16494289A JP H0331266 A JPH0331266 A JP H0331266A
- Authority
- JP
- Japan
- Prior art keywords
- group
- parts
- halogen atom
- compound
- derivative
- 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
- 239000004009 herbicide Substances 0.000 title claims abstract description 17
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 13
- 150000003230 pyrimidines Chemical class 0.000 title claims description 16
- 239000004480 active ingredient Substances 0.000 claims abstract description 25
- 230000003287 optical effect Effects 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 15
- 241000196324 Embryophyta Species 0.000 abstract description 14
- 239000002904 solvent Substances 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- -1 (substituted) ammonium Chemical class 0.000 abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 239000002585 base Substances 0.000 abstract description 3
- 240000007594 Oryza sativa Species 0.000 abstract description 2
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 2
- 235000021307 Triticum Nutrition 0.000 abstract description 2
- 244000098338 Triticum aestivum Species 0.000 abstract description 2
- 240000008042 Zea mays Species 0.000 abstract description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 235000005822 corn Nutrition 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 235000009566 rice Nutrition 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 abstract 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 abstract 1
- 235000005476 Digitaria cruciata Nutrition 0.000 abstract 1
- 235000006830 Digitaria didactyla Nutrition 0.000 abstract 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 abstract 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 abstract 1
- 244000058871 Echinochloa crus-galli Species 0.000 abstract 1
- 244000025670 Eleusine indica Species 0.000 abstract 1
- 235000014716 Eleusine indica Nutrition 0.000 abstract 1
- 241000490453 Rorippa Species 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 244000184734 Pyrus japonica Species 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000234653 Cyperus Species 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000009969 flowable effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004563 wettable powder 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 244000172533 Viola sororia Species 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
- 238000009835 boiling Methods 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- OLLQYIBTJXUEEX-UHFFFAOYSA-N diethyl 3-hydroxypentanedioate Chemical compound CCOC(=O)CC(O)CC(=O)OCC OLLQYIBTJXUEEX-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- 241000254032 Acrididae Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101000613598 Carica papaya Caricain Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 101100145155 Escherichia phage lambda cIII gene Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010033546 Pallor Diseases 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BZFWGBFTIQSEBN-UHFFFAOYSA-N ethyl 3-hydroxy-2-methylbutanoate Chemical compound CCOC(=O)C(C)C(C)O BZFWGBFTIQSEBN-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 150000002576 ketones Chemical class 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
- KJRFTNVYOAGTHK-UHFFFAOYSA-N methyl 3-hydroxy-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CO KJRFTNVYOAGTHK-UHFFFAOYSA-N 0.000 description 1
- XTXCFTMJPRXBBC-UHFFFAOYSA-N methyl 4,4-dimethyl-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(C)(C)C XTXCFTMJPRXBBC-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
本発明は新規なピリミジン誘導体もしくは該誘導体の光
学異性体及び該誘導体の１種又は２種以上を有効成分と
して含有する除草剤に関するものである。Detailed Description of the Invention (a) Industrial Application Field The present invention relates to a novel pyrimidine derivative, an optical isomer of the derivative, and a herbicide containing one or more of the derivatives as an active ingredient. be.
（ロ）従来の技術
従来、除草剤を使用するにあたっては、単位面積当たり
の有効成分処理量の多少により、除草剤を使用する際の
経済コストが左右されることが一般的に指摘されており
、使用薬量の低い、新規な除草剤の出現が望まれている
。(b) Conventional technology It has generally been pointed out that the economic cost of using herbicides is influenced by the amount of active ingredient treated per unit area. There is a desire for the emergence of new herbicides that require lower dosages.
一方、従来の除草剤では、使用時、作物に対して悪影響
を及ぼす場合があり、低薬量で高い除草効果、より高度
な作物と雑草間の選択性を有する化合物の研究が長年に
わたり続けられてきた。On the other hand, conventional herbicides can have an adverse effect on crops when used, and research has continued for many years into compounds that have high herbicidal effects at low doses and higher selectivity between crops and weeds. It's here.
例えば、ピリミジン核を有する除草剤として特開昭５４
−５５７２９号公報等が知られている。For example, as a herbicide with a pyrimidine core,
-55729 etc. are known.
（ハ）発明の態様
本発明者らは、長年にわたる研讃を重ねた結果、本発明
のピリミジン誘導体もしくは該誘導体の光学異性体が従
来の除草剤に比べ著しく除草効果が高く、しかも本発明
のピリミジン誘導体もしくは該誘導体の光学異性体の幾
つかは、イネ、トウモロコシ、コムギ、ダイス、ワタ、
ビート等の作物に選択性を有し実用的に有用であること
、更に重要雑草であるノビエ、メヒシバ、カヤツリグサ
、イヌホーズキ、ハキダメギク、イヌガラシ、ホタルイ
、コナギ、キカシグサ、ウリカワに優れた活性を有して
いることを見出し、本発明を完成するに至った。(C) Aspects of the Invention As a result of many years of research, the present inventors have found that the pyrimidine derivative of the present invention or the optical isomer of the derivative has a significantly higher herbicidal effect than conventional herbicides, and that Some of the pyrimidine derivatives or optical isomers of the derivatives are used in rice, corn, wheat, soybeans, cotton, etc.
It is selective and practically useful for crops such as beets, and it also has excellent activity against important weeds such as wild grass, cyperus, cyperus, japonica, japonica, japonica, bulrush, japonica, japonica, and urikawa. The present invention was completed based on this discovery.
即ち、本発明のピリミジン誘導体もしくは該誘導体の光
学異性体は、従来の公知化合物に比べて単位面積当たり
の有効成分投下量を著しく低減させることができ、従来
の除草剤と比べ作物に対する薬害は極めて軽微であり、
その経済効果は極めて大である。That is, the pyrimidine derivatives of the present invention or the optical isomers of the derivatives can significantly reduce the amount of active ingredients applied per unit area compared to conventionally known compounds, and are extremely less harmful to crops than conventional herbicides. Minor;
The economic effect is extremely large.
更に、本発明のピリミジン誘導体もしくは該誘導体の光
学異性体は農薬の多鼠施用による環境汚染の危険性を著
しく低減することができ、土壌残留による他の作物への
悪影響も少ない画期的な除草剤といえる。Furthermore, the pyrimidine derivative or the optical isomer of the derivative of the present invention can significantly reduce the risk of environmental contamination due to the multiple application of pesticides, and can be used as an innovative weed killer with less negative impact on other crops due to residual soil. It can be said to be a drug.
本発明は一般式ＣＩ）
〔式中、Ｒは水素原子、置換していてもよい低級アルキ
ル基（この置換基としてはハロゲン原子、低級アルコキ
シ基、低級アルキルチオ基或いはハロゲン原子、低級ア
ルキル基、低級アルコキシ基、低級アルキルチオ基で置
換していてもよいフェニル基を示す。）、アルカリ金属
、アルカリ土類金属もしくは置換されていてもよいアン
モニウムカチオンを表す。The present invention is based on the general formula CI) [wherein R is a hydrogen atom, an optionally substituted lower alkyl group (such as a halogen atom, a lower alkoxy group, a lower alkylthio group, or a halogen atom, a lower alkyl group, a lower represents a phenyl group which may be substituted with an alkoxy group or a lower alkylthio group), an alkali metal, an alkaline earth metal, or an optionally substituted ammonium cation.
Ｒ１、Ｒ２は各々同−又は相異なってもよく、ハロゲン
原子、低級アルキル基、低級ハロアル−１−ル基、低級
アルコキシ基、低級ハロアルコキシ基もしくは低級ジア
ルキルアミノ基を表す。R1 and R2 may be the same or different, and each represents a halogen atom, a lower alkyl group, a lower haloal-1-l group, a lower alkoxy group, a lower haloalkoxy group or a lower dialkylamino group.
ＸＩ 、）（２、ＹｌおよびＹ２は各々同−又は相異な
ってもよく、水素原子、シアノ基、カルボキシル基、低
級アルコキシカルボニル基、ホルミル基、低級アルコキ
シ基、置換していてもよい低級アルキル基（この置換基
としてはハロゲン原子、シアノ基、ニトロ基、ホルミル
基、低級アルコキシ基、低級アルキルチオ基、カルボキ
シル基、低級アルコキシカルボニル基、低級ジアルキル
アミノ基、フェニル基、フェノキシ基あるいはフェニル
チオ基を示す。）、置換していてもよい低級アルケニル
基（この置換基としてはハロゲン原子、シアノ基、ニト
ロ基、ホルミル基、低級アルコキシ基、カルボキシル基
、低級アルコキシ力ルポニル基、フェニル基もしくはフ
ェノキシ基を示す。）、置換していてもよいフェニル基
（この置換基としてはハロゲン原子、シアノ基、ニトロ
基、低級アルキル基、低級アルコキシ基、カルボキシル
基あるいは低級アルコキシカルボニル基を示す。）を表
す。］で表されるピリミジン誘導体もしくは該誘導体の
光学異性体に関し、更にピリミジン誘導体もしくは該誘
導体の光学異性体の１種又は２種以上を有効成分として
含有する除草剤に関するものである。XI, ) (2, Yl and Y2 may be the same or different, and each represents a hydrogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a formyl group, a lower alkoxy group, an optionally substituted lower alkyl group (This substituent includes a halogen atom, a cyano group, a nitro group, a formyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a lower dialkylamino group, a phenyl group, a phenoxy group, or a phenylthio group. ), an optionally substituted lower alkenyl group (such substituents include a halogen atom, a cyano group, a nitro group, a formyl group, a lower alkoxy group, a carboxyl group, a lower alkoxy group, a phenyl group, or a phenoxy group). ), an optionally substituted phenyl group (the substituents include a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower alkoxy group, a carboxyl group, or a lower alkoxycarbonyl group). The present invention relates to a pyrimidine derivative or an optical isomer of the derivative, and further relates to a herbicide containing one or more of the pyrimidine derivative or the optical isomer of the derivative as an active ingredient.
本発明のピリミジン誘導体もしくは該誘導体の光学異性
体は文献未記載の新規化合物であり、且つ除草剤として
優れた生理活性を有する。The pyrimidine derivative of the present invention or the optical isomer of the derivative is a novel compound that has not been described in any literature, and has excellent physiological activity as a herbicide.
本発明の一般式（１）で表されるピリミジン誘導体もし
くは該誘導体の光学異性体は、一般式（ＩＩ）
〔式中、Ｒ，Ｘ’ 、Ｘ”
同じ意味を表す。〕
で表されるアルコールと
一般式（ＩＩＩ）
Ｙｌ及びＹ２は前記と
ｉ
〔式中、Ｒ３はハロゲン原子、アルキルスルホニル基又
は置換されていてもよいベンジルスルホニル基を表し、
Ｒ１、ｐ、ｚは前記と同じ意味を表す。〕
で表されるピリミジン化合物を、任意の割合、好ましく
は一般式（Ｉｔ）の環状アルコール１モルに対して一般
式（ＩＩ［）のピリミジン化合物１モルを混合し、必要
ならば、塩基の存在下溶媒中で反応させることによって
製造することができる。The pyrimidine derivative represented by the general formula (1) or the optical isomer of the derivative of the present invention is an alcohol represented by the general formula (II) [wherein R, X', and X'' represent the same meaning] and general formula (III) Yl and Y2 are as above i [wherein R3 represents a halogen atom, an alkylsulfonyl group or an optionally substituted benzylsulfonyl group,
R1, p and z have the same meanings as above. ] The pyrimidine compound represented by is mixed in any ratio, preferably 1 mol of the pyrimidine compound of the general formula (II[) to 1 mol of the cyclic alcohol of the general formula (It), and if necessary, the presence of a base is added. It can be produced by reacting in a lower solvent.
溶媒としては、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、メチルアルコール、エチルアルコー
ル、イソプロピルアルコール等のアルコール系溶媒、ジ
エチルエーテル、ジ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、その他アセトニトリル、水
等が挙げられる。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 methyl alcohol, ethyl alcohol, and isopropyl alcohol, diethyl ether, diisopropyl ether, and tetrahydrofuran. , ether solvents such as 1゜4-dioxane, 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, and other acetonitrile. , water, etc.
塩基としては１、金属ナトリウト、金属カリウム等のア
ルカリ金属類、水素化す） ＩＪ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、トリ
エチルアミン、ピリジン等の有機塩基が挙げられる。Bases include 1, alkali metals such as sodium metal and potassium metal, hydrides), alkali metal hydrides such as calcium hydride, alkaline earth metal hydrides, carbonates such as sodium carbonate and potassium carbonate, Examples include metal hydroxides such as sodium hydroxide and potassium hydroxide, and organic bases such as triethylamine and pyridine.
反応は、溶媒の凝固点から沸点までの任意の温度、好ま
しくは０゛Ｃから溶媒の沸点迄の温度で行なうことがで
き、必要に応じて加熱或いは冷却することができる。The reaction can be carried out at any temperature from the freezing point to the boiling point of the solvent, preferably from 0°C to the boiling point of the solvent, and can be heated or cooled as necessary.
反応時間としては、数分〜数十時間、好ましくは０．５
〜３５時間がよい。The reaction time is several minutes to several tens of hours, preferably 0.5
~35 hours is good.
上記のような製造法により得られた本発明のピリミジン
誘導体もしくは該誘導体の光学異性体は、必要に応じて
再結晶或いはカラムクロマトグラフィーによって精製す
ることもできる。The pyrimidine derivative of the present invention obtained by the above production method or an optical isomer of the derivative can be purified by recrystallization or column chromatography, if necessary.
以下、本発明を合成例、配合例及び試験例により更に詳
しく説明するが本発明はこれらに限られるものではない
。The present invention will be explained in more detail below using synthesis examples, formulation examples, and test examples, but the present invention is not limited thereto.
幻Ｕ土
（本発明化合物Ｎα１２２）
２−メチル−３−ヒドロキシブタン酸エチルエステル１
．４６ ｇ （０，０１モル）および２−メタンスルホ
ニル−４，６−シメトキシピリミジン２．０ｇ（０，０
０９２モル）を無水テトラヒドロフラン５０ｍ１に溶解
し、氷水浴で冷却した。Gen U soil (inventive compound Nα122) 2-methyl-3-hydroxybutanoic acid ethyl ester 1
．． 46 g (0,01 mol) and 2.0 g (0,0
092 mol) was dissolved in 50 ml of anhydrous tetrahydrofuran and cooled in an ice-water bath.
次に水素化ナトリウム０．５ｇ（５５％、油性）を添加
し室温で一晩撹拌した。反応終了を薄層クロマトグラフ
ィーで確認した後、反応混合物を氷水にあけ、酢酸エチ
ルで抽出後、無水硫酸ナトリウムで乾燥し、溶媒を留去
した。カラムクロマトグラフィー精製後２．４３ｇ（収
率９３％）の本発明化合物Ｎα１２２を無色粘稠液体と
して得た。Next, 0.5 g of sodium hydride (55%, oily) was added and stirred overnight at room temperature. After confirming the completion of the reaction by thin layer chromatography, the reaction mixture was poured into ice water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off. After column chromatography purification, 2.43 g (yield 93%) of the present compound Nα122 was obtained as a colorless viscous liquid.
物性 液体 ｎｏｚｏｌ、４８６４
’Ｈ−ＮＭＲ［δ値（ｐｐｍ）、ＣＤＣｌ３］１．０３
〜１．５０（９Ｈ，ｍ）
２．６３〜３．１２（ｉｌｌ、ｍ）
３．８７（６１１，ｓ） ４．１０（２１！、ｑ、Ｊ
＝６．５１１ｚ）５．０９〜５．５９（ＩＩＩ、ｍ）
５．６１ （ＩＩＩ、 ｓ）
金城Ｊじ−
（本発明化合物Ｎα２００）
メチル２．２−ジメチル−３−ヒドロキシプロピオネー
ト０．９３ ｇ （０，００７モル）及び２−メタンス
ルホニル−４，６−シメトキシビリミジン１．５ｇ（０
，００６９モル）を無水テトラヒドロフラン８０ｍｆｆ
１に溶かし、氷水浴にて冷却した。Physical properties Liquid nozol, 4864'H-NMR [δ value (ppm), CDCl3] 1.03
~1.50 (9H, m) 2.63 ~ 3.12 (ill, m) 3.87 (611, s) 4.10 (21!, q, J
=6.511z) 5.09-5.59 (III, m) 5.61 (III, s) Kinjo Jji- (Compound of the present invention Nα200) Methyl 2.2-dimethyl-3-hydroxypropionate 0. 93 g (0,007 mol) and 1.5 g (0
,0069 mol) in anhydrous tetrahydrofuran 80 mff
1 and cooled in an ice water bath.
次に水素化ナトリウム０．４４ｇ（５５％、油性）を加
え室温で一晩撹拌した。反応混合物を氷水にあけ、ジエ
チルエーテルで抽出後、無水硫酸ナトリウムで乾燥し、
溶媒を留去した。カラムクロマトグラフィー精製後１．
６５ ｇ （０，００６モル、収率８７％）の本発明化
合物Ｎα２００を得た。Next, 0.44 g (55%, oily) of sodium hydride was added and stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with diethyl ether, and dried over anhydrous sodium sulfate.
The solvent was distilled off. After column chromatography purification1.
65 g (0,006 mol, yield 87%) of the present compound Nα200 was obtained.
物性 固体 融点 ７６．０〜８０．０°Ｃ’ＩＩ−Ｎ
ＭＲ［δ値（ｐｐｍ） 、 ＣＤＣｌ ｙ ］１．３０
（６ｆ１．ｓ） ３．６８（３Ｈ，ｓ）３．
９０ （６１１，ｓ） ４．３８（２１１，ｓ
）５．６７ （ｉｌｌ、ｓ）
合議Ｉ［支
（本発明化合物Ｎα２６１）
エチルトリフルオロアセトアセテート２ｇ（０，０１０
９モル）を無水ジエチルエーテルに溶かし氷水浴で冷却
した。次にボランアンモニアコンプレックス０．１８
ｇを加え室温で一晩撹拌した。Physical properties Solid Melting point 76.0-80.0°C'II-N
MR [δ value (ppm), CDCly] 1.30
(6f1.s) 3.68 (3H,s)3.
90 (611,s) 4.38 (211,s
) 5.67 (ill, s) Council I
9 mol) was dissolved in anhydrous diethyl ether and cooled in an ice-water bath. Next, borane ammonia complex 0.18
g was added thereto, and the mixture was stirred at room temperature overnight.
反応終了後希塩酸で中和し、ジエチルエーテルで抽出し
、無水硫酸ナトリウムで乾燥した。溶媒留去後１．６６
ｇ（収率８０％）のエチル ３−ヒドロキシ−４，４，
４−）リフルオロブチレートを得た。After the reaction was completed, the mixture was neutralized with diluted hydrochloric acid, extracted with diethyl ether, and dried over anhydrous sodium sulfate. After solvent distillation 1.66
g (yield 80%) of ethyl 3-hydroxy-4,4,
4-) Rifluorobutyrate was obtained.
４．６−シメトキシビリミジン１．９４ ｇを無水テト
ラヒドロフラン８０ｍｊ！に溶かし、氷水冷で冷却した
。4.1.94 g of 6-cymethoxypyrimidine and 80 mj of anhydrous tetrahydrofuran! The mixture was dissolved in water and cooled with ice water.
次に水素化ナトリウム０．５２ｇ（５５％、抽出）を加
え室温で一晩撹拌した。カラムクロマトグラフィー精製
後、目的化合物０．５３ｇ（収率１８％）を得た。Next, 0.52 g (55%, extracted) of sodium hydride was added and stirred overnight at room temperature. After column chromatography purification, 0.53 g (yield 18%) of the target compound was obtained.
物性 液体 ｎｏ” １．４５３５
’ＩＩ−ＮＭＲ［δ値（ｐｐｍ） 、 ＣＤＣ尼ｚ ］
１．２０ （３１１，ｔ、Ｊ＝７．０１ｌｚ）２．８５
〜３．０Ｏ（２１１，ｍ）
３．９０（６Ｂ、ｓ） ４．１０（２１１，ｑ、Ｊ＝
７．０ｌｌｚ）５．７５（ＩＩＩ、ｓ） ６．１〜６
．４０（ＩＩＩ、ｍ）合議Ｉ引（
（本発明化合物Ｎα３０５）
上記で得た化合物及び２−メタンスルホニル−メチル３
−ヒドロキシ−４，４，４−）リクロロブチジーＮ、５
２ｇ及び２−メタンスルホニル−４，６−シメトキシビ
リミジン１．５ ｇ （０，００６９モル）を無水テト
ラヒドロフラン８０ｍ１に溶かし氷水浴にて冷却した。Physical properties Liquid no. 1.4535 'II-NMR [δ value (ppm), CDCNMR]
1.20 (311,t, J=7.01lz)2.85
~3.0O (211, m) 3.90 (6B, s) 4.10 (211, q, J=
7.0llz) 5.75 (III, s) 6.1~6
．． 40 (III, m) Consultation I ((Compound of the present invention Nα305) The compound obtained above and 2-methanesulfonyl-methyl 3
-Hydroxy-4,4,4-)lichlorobutidy N,5
2 g and 1.5 g (0,0069 mol) of 2-methanesulfonyl-4,6-simethoxypyrimidine were dissolved in 80 ml of anhydrous tetrahydrofuran and cooled in an ice-water bath.
次に水素化ナトリウム０．４５ ｇ（５５％、油性）を
加え室温で一晩撹拌した。Next, 0.45 g of sodium hydride (55%, oily) was added and stirred overnight at room temperature.
反応溶液を氷水にあけ、ジエチルエーテルで抽出後、無
水硫酸す） ＩＪウムで乾燥し、溶媒を留去した。カラ
ムクロマトグラフィーで精製後１．３１ｇ （０，００
３６４モル、収率５３％）の本発明化合物ＮＯ，３０５
を得た。The reaction solution was poured into ice water, extracted with diethyl ether, dried over anhydrous sulfuric acid, and the solvent was distilled off. After purification by column chromatography, 1.31g (0,00
364 mol, yield 53%) of the present compound NO, 305
I got it.
物性 固体 融点 ６１．０〜６３，０°Ｃ’ＩＩ−Ｎ
ＭＲ［δイ直（ｐｐｍ）、ＣＤＣｌ ｓ ］３．１５
（２１１，ｄ、ｄ、ｄ、 Ｊ＝４．０ｌｌｚ、 １．０
ＩＩｚ、 ３．０１ｌｚ）３．６２（３１１，ｓ）
３．９２（６１１，ｓ）５．７５（ｌｔｌ、ｓ）
６．４５（１１１，ｄｄ、Ｊ＝４１１ｚ、７１１ｚ）企
裁２例」−
（本発明化合物Ｎα４７６）
メチル３−オキソ−４，４−ジメチルペンタネート２ｇ
を合成例３と同様の方法でメチル３−ヒドロキシ−４，
４−ジメチルペンタネート１．８ｇ（収率８９％）を合
成し、さらに合成例３と同様の操作を経て本発明化合物
Ｎα４７６を０．５５ｇ（収率１６％）で得た。Physical properties Solid Melting point 61.0-63,0°C'II-N
MR [δ i (ppm), CDCl s ] 3.15
(211, d, d, d, J=4.0llz, 1.0
IIz, 3.01lz) 3.62 (311,s)
3.92 (611, s) 5.75 (ltl, s)
6.45 (111, dd, J=411z, 711z) 2 cases of trial” - (Compound of the present invention Nα476) Methyl 3-oxo-4,4-dimethylpentanate 2 g
in the same manner as in Synthesis Example 3 to prepare methyl 3-hydroxy-4,
1.8 g (yield: 89%) of 4-dimethylpentanate was synthesized, and the same operation as in Synthesis Example 3 was performed to obtain 0.55 g (yield: 16%) of the present compound Nα476.
物性 液体 ｎＤ” １．４８７８
’ＩＩ−ＮＭＲ［δ値（ｐｐｍ） 、 ＣＤＣＱ ：ｌ
］］１００ （９８，ｓ） ２．６７（２１１，ｄ
Ｊ＝７．０１１ｚ）３．６０ （３Ｌｓ） ３．９
５ （６１１，ｓ）５．６０ （１１，ｔ Ｊ＝７．
０１１ｚ）５．７０（ＬＨ，ｓ）
合議ｕ１灸
’ＩＩ−ＮＭＲ［δ値（ＰＰＩＩＩ） 、 ＣＤＣｆｆ
ｉ 、 ］２．９７ （２８，ｄ、 Ｊ＝８．６Ｈ
ｚ）３．７０ （６１１，ｓ） ３．８５（６１
１，ｓ）５．６５ （ＩＩＩ、ｔ Ｊ＝８．０Ｈｚ）
５．６７（ｌｔｌ、ｓ）合部■引Ｌ
（本発明化合物Ｎα６１８）
Ｄ、Ｌ−リンゴ酸ジメチル０．７４ ｇ （０，００４
６モル）及び２−メタンスルホニル−４，６−ジメトキ
シピリミジン１ ｇ （０，００４６モル）を無水テト
ラヒドロフラン５０ｍｊ２に溶かし氷水浴にて冷却した
。次に水素化ナトリウム０．２５ｇ（５５％、油性）を
加え室温で一晩撹拌した。Physical properties Liquid nD" 1.4878 'II-NMR [δ value (ppm), CDCQ: l
]]100 (98,s) 2.67(211,d
J=7.011z) 3.60 (3Ls) 3.9
5 (611,s)5.60 (11,t J=7.
011z) 5.70 (LH, s) Council u1 Moxibustion'II-NMR [δ value (PPIII), CDCff
i, ]2.97 (28,d, J=8.6H
z) 3.70 (611, s) 3.85 (61
1, s) 5.65 (III, t J=8.0Hz)
5.67 (ltl, s) joint ■ pull L (inventive compound Nα618) D, L-dimethyl malate 0.74 g (0,004
6 mol) and 1 g (0,0046 mol) of 2-methanesulfonyl-4,6-dimethoxypyrimidine were dissolved in 50 mj2 of anhydrous tetrahydrofuran and cooled in an ice-water bath. Next, 0.25 g (55%, oily) of sodium hydride was added and stirred overnight at room temperature.
反応混合物を氷水にあけジエチルエーテルで抽出後、無
水硫酸ナトリウムで乾燥し、溶媒を留去した。カラムク
ロマトグラフィー精製後１．０８ ｇ（０，００３６モ
ル、収率７８％）の本発明化合物Ｎα６１８を得た。The reaction mixture was poured into ice water, extracted with diethyl ether, dried over anhydrous sodium sulfate, and the solvent was distilled off. After column chromatography purification, 1.08 g (0,0036 mol, yield 78%) of the present compound Nα618 was obtained.
物性 固体 融点 ５７．０〜６１．０℃（本発明化合
物Ｎｏ、 ６２２ ）
ジエチル１．３−アセトンジカルボキシレート２０ｇ（
０，１０モル）の２００ｍ１ジエチルエーテル？容液に
ボラン−タージャリーフ゛チルアミンコンプレックス３
．２ｇを加え、室温で一昼夜撹拌した。Physical properties Solid Melting point 57.0 to 61.0°C (Compound No. 622 of the present invention) 20 g of diethyl 1.3-acetonedicarboxylate (
0.10 mol) of 200ml diethyl ether? Borane-tajary ethylamine complex 3 in solution
．． 2 g was added, and the mixture was stirred at room temperature all day and night.
それに希塩酸水溶液を加え弱酸性とした後、分液し、有
機溶液を乾燥′ａ縮して、粗３−ヒドロキシグルタル酸
ジエチルエステル１４．１ ｇを得た。After making it weakly acidic by adding a dilute aqueous hydrochloric acid solution, the mixture was separated, and the organic solution was dried and condensed to obtain 14.1 g of crude 3-hydroxyglutaric acid diethyl ester.
この３−ヒドロキシグルタル酸ジエチルエステル２、Ｏ
ｇおよび２−メタンスルホニル−４，６−ジメトキシピ
リミジン２．０ｇを無水テトラヒドロフラン５０ｍ１に
溶解し、氷水浴で冷却した。以後合成例１と同様の方法
により、本発明化合物Ｎｏ。This 3-hydroxyglutarate diethyl ester 2,O
g and 2.0 g of 2-methanesulfonyl-4,6-dimethoxypyrimidine were dissolved in 50 ml of anhydrous tetrahydrofuran and cooled in an ice-water bath. Thereafter, the same method as in Synthesis Example 1 was used to prepare compound No. of the present invention.
６２２を２．８０ｇ（収率９０％）で１）た。2.80 g (yield 90%) of 622 was obtained (1).
物性 液体 ｎｏｚｏ １．４８２３
’＋１−ＮＭＲ［δ値（ｐｐ積）、ＣＤＣｊ！ｉ ］１
．２０ （３１１，ｔ、Ｊ＝’？、０１１ｚ）１．２３
（３１１，ｔ、Ｊ＝７．０ｔｌｚ）２．３１ （２１
１，ｄ、Ｊ＝７．０ｌｌｚ）２．３４ （２１１，ｄ、
Ｊ＝７．０ｆ（ｚ）３．８７ （６１１，ｓ） ４
．Ｑ８（４１（、ｑ、Ｊ＝７．ｏｌＩｚ）５．６５ （
ｉｌｌ、ｓ） ５．８３（ｉｌｌ、５ｔｈ、Ｊ＝７
．０ｆ（ｚ）又、合成例１から合成例７と同様な合成法
によって得られる本発明化合物を第１表に示す。Physical properties Liquid nozo 1.4823'+1-NMR [δ value (pp product), CDCj! i ] 1
．． 20 (311, t, J='?, 011z) 1.23
(311,t, J=7.0tlz)2.31 (21
1, d, J=7.0llz) 2.34 (211, d,
J=7.0f(z)3.87 (611,s) 4
．． Q8(41(,q,J=7.olIz)5.65 (
ill, s) 5.83 (ill, 5th, J=7
．． 0f(z) Table 1 also shows the compounds of the present invention obtained by the same synthesis methods as Synthesis Examples 1 to 7.
また物性値を前記実施例を含めて第２表に示す。Further, physical property values are shown in Table 2 including the above examples.
本発明化合物Ｎαは、以下の配合例及び試験例について
参照される。The compound Nα of the present invention is referred to in the following formulation examples and test examples.
本発明のピリミジン誘導体もしくは該誘導体の光学異性
体を除草剤として施用するにあたっては−ａには適当な
担体、例えばクレー、タルク、ベントナイト、珪藻土等
の固体担体或いは水、アルコール類（メタノール、エタ
ノール等）、芳香族炭化水１類（ベンゼン、トルエン、
キシレン等）塩素化炭化水素類、エーテル類、ケトン類
、エステル１ｊｌｌ （酢酸エチル等）、酸アミド類（
ジメチルホルムアミド等）等の液体担体と混用して適用
することができ、所望により乳化剤、分散剤、懸濁剤、
浸透剤、展着剤、安定剤等を添加し、液剤、乳剤、水和
剤、粉剤、粒剤、フロアブル剤等任意の剤型にて実用に
供することができる。When applying the pyrimidine derivative of the present invention or an optical isomer of the derivative as a herbicide, -a is a suitable carrier, such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, or water, alcohol (methanol, ethanol, etc.). ), aromatic hydrocarbons class 1 (benzene, toluene,
xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (
It can be applied by mixing with a liquid carrier such as dimethylformamide (dimethylformamide, etc.), and if desired, emulsifiers, dispersants, suspending agents, etc.
By adding a penetrating agent, a spreading agent, a stabilizer, etc., it can be put to practical use in any desired dosage form such as a liquid, emulsion, wettable powder, powder, granule, or flowable agent.
これらの製剤中における有効成分化合物の含有量は特に
限定されるものではないが、一般に０．１０〜９０．０
重量％の範囲が望ましい。The content of the active ingredient compound in these preparations is not particularly limited, but is generally 0.10 to 90.0.
A weight percent range is desirable.
又、必要に応じて製剤化又は散布時に他種の除草剤、各
種殺虫剤、殺菌剤、植物生長調節剤、共力剤等と混合施
用してもよい。Further, if necessary, it may be mixed with other herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. during formulation or spraying.
例えば、ファーム・ケミカルズ・ハンドブック（Ｆａｒ
ｍ Ｃｈｅｍｉｃａｌｓ ）ｌａｎｄｂｏｏｋ）、第７
５版、１９８９年に記載されている化合物等がある。For example, the Farm Chemicals Handbook (Far
m Chemicals) landbook), No. 7
There are compounds described in the 5th edition, 1989.
尚、本発明のピリミジン誘導体もしくは該誘導体の光学
異性体は畑地、水田、果樹園等の農園芸分野以外に運動
場、空地、線路端等非農耕地における各種雑草の防除に
も適用することができ、その施用薬量は適用場面、施用
時期、施用方法、対象草種、栽培作物等により差異はあ
るが、一般には有効成分量としてヘクタール当たり０．
００５〜１０ｋｇ程度が適当である。In addition, the pyrimidine derivative of the present invention or the optical isomer of the derivative can be applied to control various weeds not only in agricultural and horticultural fields such as fields, paddy fields, and orchards, but also in non-agricultural fields such as playgrounds, vacant lots, and railway edges. The amount of the applied drug varies depending on the application situation, application time, application method, target grass species, cultivated crops, etc., but in general, the amount of active ingredient is 0.00% per hectare.
Approximately 0.05 to 10 kg is appropriate.
次に、本発明のピリミジン誘導体もしくは該誘導体の光
学異性体を有効成分とする除草剤の配合例を示すが、こ
れらのみに限定されるものではない。Next, examples of formulations of herbicides containing the pyrimidine derivative of the present invention or an optical isomer of the derivative as an active ingredient will be shown, but the invention is not limited thereto.
尚、以下の配合例において１部」は重量部を意味する。In addition, in the following formulation examples, "1 part" means part by weight.
散−月
有効成分 ：５〜７５部、望ましくは１０〜５０部、特
に１５〜４０部が好ましい。Active ingredient: 5 to 75 parts, preferably 10 to 50 parts, particularly preferably 15 to 40 parts.
液体担体 ：９５〜２５部、望ましくは８８〜３０部、
特に８２〜４０部が好ましい。Liquid carrier: 95 to 25 parts, preferably 88 to 30 parts,
Particularly preferably 82 to 40 parts.
界面活性剤：１〜３０部、望ましくは２〜２０部。Surfactant: 1 to 30 parts, preferably 2 to 20 parts.
１−コ可
有効成分 ：１〜５０部、望ましくは５〜４５部、特に
１０〜４０部が好ましい。1-Co active ingredient: 1 to 50 parts, preferably 5 to 45 parts, particularly preferably 10 to 40 parts.
界面活性剤：１〜３０部、望ましくは２〜２５部、特に
３〜２０部が好ましい。Surfactant: 1 to 30 parts, preferably 2 to 25 parts, particularly preferably 3 to 20 parts.
液体担体 ：２０〜９５部、望ましくは３０〜９３部、
特に５７〜８５部が好ましい。Liquid carrier: 20 to 95 parts, preferably 30 to 93 parts,
Particularly preferably 57 to 85 parts.
紛−コ肌 有効成分 二０．５〜１０部。Pale skin Active ingredient 20.5 to 10 parts.
特に１５〜４０部が好ましい。Particularly preferred is 15 to 40 parts.
固体担体 ： ９５．５〜９０部。Solid carrier: 95.5 to 90 parts.
２旦１ズ及■ 有効成分 ＝５〜７５部、望ましくは１０〜５０部。2dan 1z and■ Active ingredient = 5 to 75 parts, preferably 10 to 50 parts.
水 ：９４〜２５部、望ましくは９０〜３０部
。Water: 94 to 25 parts, preferably 90 to 30 parts.
界面活性剤：１〜３０部、望ましくは２〜２０部。Surfactant: 1 to 30 parts, preferably 2 to 20 parts.
氷−祖−Ｍ
有効成分 ：２．５〜９０部、望ましくは１０〜８０部
、特に２０〜７５部が好ましい。Ice-So-M Active ingredient: 2.5 to 90 parts, preferably 10 to 80 parts, particularly preferably 20 to 75 parts.
界面活性剤：０．５〜２０部、望ましくは１〜１５部、
特に２〜１０部が好ましい。Surfactant: 0.5 to 20 parts, preferably 1 to 15 parts,
Particularly preferably 2 to 10 parts.
液体担体 ：５〜９０部、望ましくは７．５〜８８部、
特に１６〜５６部が好ましい。Liquid carrier: 5 to 90 parts, preferably 7.5 to 88 parts,
Particularly preferably 16 to 56 parts.
粒−１− 有効成分 ：０．１〜３０部。grain-1- Active ingredient: 0.1 to 30 parts.
固体担体 ： ９５．５〜７０部。Solid carrier: 95.5 to 70 parts.
液剤及び乳剤（よ界面活性剤を含む液体担体に有効成分
を溶解して調整する。水和剤は界面活性剤、固体担体及
び有効成分を混合し、更に粉砕することにより調整する
。Solutions and emulsions are prepared by dissolving the active ingredient in a liquid carrier containing a surfactant. Wettable powders are prepared by mixing a surfactant, a solid carrier, and the active ingredient, and then pulverizing the mixture.
粉剤は界面活性剤、固体担体及び有効成分を混合し、必
要ならば、更に粉砕することにより調整する。Powders are prepared by mixing the surfactant, solid carrier and active ingredient and, if necessary, further grinding.
フロアブル剤は、界面活性剤を含む水溶液に有効成分を
懸濁、分散して調整する。粒剤は有効成分と補助剤を混
合して調整する。Flowable agents are prepared by suspending or dispersing active ingredients in an aqueous solution containing a surfactant. Granules are prepared by mixing the active ingredient and adjuvants.
へ−Ｙ例」−水和剤
本発明化合物 Ｎｏ、 １２２ ・・・・・・
・・・５０部ジークライトＰＦＰ ・・・
・・・・・・４３部（カオリン系クレー：ジークライト
工業■商品名）
ツルポール５０３９ ・・・・・・・・・ ５
部（非イオン性界面活性剤とアニオン性界面活性剤との
混合物：東邦化学工業０勾商品名）カップレックス（固
結防止剤） ・・・・・・ ２部（界面活性剤とホワイ
トカーボンの混合物：塩野義製薬■商品名）
以上を均一に混合粉砕して水和剤とする。使用に際して
は上記水和剤を１０〜１０，０００倍に希釈して、有効
成分量かへクタール当たり０．００５ ｋｇ〜１０ｋｇ
になるように散布する。- Example Y” - Hydrating agent Compound of the present invention No. 122...
... 50 copies Sieglite PFP ...
・・・・・・43 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039 ・・・・・・・・・ 5
1 part (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd. product name) Couplex (anti-caking agent) 2 parts (mixture of surfactant and white carbon) Mixture: Shionogi & Co., Ltd. ■Product name) Mix and grind the above mixture uniformly to make a wettable powder. When using, the above hydrating agent is diluted 10 to 10,000 times, and the amount of active ingredient is 0.005 kg to 10 kg per hectare.
Spread it so that
配合涯ｌ 乳剤
本発明化合物 Ｎａ３０５ ・・・・・・・・
・ＩＯ部キ シ し ン
・・・・・・・・・７０部ジメチルホルムアミ
ド ・・・・・・・・弓０部ツルポール２６８０
・・・・・・・・・１０部（非イオン性界面
活性剤とアニオン性界面活性剤との混合物：東邦化学工
業Ｑ増血品名）以上を均一に混合して乳剤とする。使用
に際しては上記乳剤を１０〜１０．０００倍に希釈して
、有効成分量がへクタール当たり０．００５ｋｇ−１０
ｋｇになるように散布する。Compounding formula Emulsion Compound of the present invention Na305 ・・・・・・・・・
・IO section
・・・・・・・・・70 parts dimethylformamide ・・・・・・・・・0 parts Tsurupol 2680
. . . 10 parts or more (mixture of nonionic surfactant and anionic surfactant: Toho Kagaku Kogyo Q blood enrichment product name) are uniformly mixed to form an emulsion. When using, the above emulsion is diluted 10 to 10.000 times so that the amount of active ingredient is 0.005 kg-10 per hectare.
Spread it to make a total of kg.
Ａ匙Ｆ例Ｊ−粒剤
本発明化合物 Ｎα２６１ ・・・・・・・・
・ ５部ベントナイト ・・・・・・・
・・５４部タ ル り
・・・・・・・・・４０部リグニンスルホン酸
カルシウム・・・・・・・・・ １部以上を均一に混合
粉砕して少量の水を加えて撹拌混合し、押出式造粒機で
造粒し、乾燥して粒剤とする。使用に際しては上記乳剤
を有効成分量かへクタール当たりＯ，ＯＯ５ｋｇ〜１０
ｋｇになるように散布する。A Spoon F Example J - Granules Compound of the present invention Nα261...
・ 5th part bentonite ・・・・・・・・・
・・54 part tarri
・・・・・・・・・40 parts Calcium ligninsulfonate ・・・・・・・・・ 1 part or more is mixed and pulverized uniformly, a small amount of water is added, stirred and mixed, and extrusion granulator is used. Granulate and dry to make granules. When using the above emulsion, the amount of active ingredient is O, OO5 kg to 10 per hectare.
Spread it to make a total of kg.
酊金旦ｔ フロアブル剤
本発明化合物 Ｎｏ、４７６ ・・・・・・・
・・２５部ツルポール３３５３ ・・・・・・
・・・１０部（非イオン性界面活性剤：東邦化学工業■
商品名）
ルノックス１００ＯＣ・・・・・・・・・０．５部（陰
イオン性界面活性剤：東邦化学工業９１商品名）
１％ザンサンガム水溶液 ・・・・・・・・・２０
部（天然高分子）
水 ・・・・・・
４４．５部ツルポール３３５３、ルノックス１００ＯＣ
及び１％ザンサンガム水溶液を水に均一に溶解し、次に
本発明化合物Ｎα３８を加えよく撹拌した後、サンドミ
ルにて湿式粉砕してフロアブル剤を得る。Noukindant Flowable agent Compound of the present invention No. 476 ・・・・・・・・・
・・25 part vine pole 3353 ・・・・・・
...10 parts (nonionic surfactant: Toho Chemical Industry ■
Product name) Lunox 100OC 0.5 part (anionic surfactant: Toho Chemical Industry 91 product name) 1% xanthan gum aqueous solution 20
Part (natural polymer) Water ・・・・・・
44.5 part Tsurupol 3353, Lunox 100OC
and 1% xanthan gum aqueous solution were uniformly dissolved in water, and then the compound of the present invention Nα38 was added and stirred well, followed by wet grinding in a sand mill to obtain a flowable agent.
使用に際しては、上記フロアブル剤を１０〜１０．００
０倍に希釈して有効成分量かへクタール当たり０．００
５ ｋｇ−１０ｋｇになるように分散する。When using, the above flowable agent should be added at a rate of 10 to 10.00
The amount of active ingredient when diluted to 0 times is 0.00 per hectare.
Distribute to weigh between 5 kg and 10 kg.
次に、本発明化合物の除草剤としての有用性を以下の試
験例において具体的に説明する。Next, the usefulness of the compounds of the present invention as herbicides will be specifically explained in the following test examples.
が３支例」−土壌処理による除草効果試験縦３０ｃｍ、
横２２ｃｍ、深さ６ｃＩＩＩのプラスチック製箱に殺菌
した洪積土壌を入れ、ノビエ、メヒシバ、カヤツリグサ
、イヌホーズキ、ハキダメギク、イヌガラシ、ワタを播
種し、約１．５ ｃｍ覆土した後有効成分量が所定の割
合となるように土壌表面へ均一に散布した。散布の際の
薬液は、前記配合例の液剤、水和剤、乳剤又はフロアブ
ル剤を水で希釈して小型スプレーで全面に散布した。薬
液＋Ｉｔ布４布間週間後種雑草に対する除草効果を下記
の判定基準に従い調査した。3 supporting examples - Test of herbicidal effect by soil treatment 30 cm long,
Fill a plastic box with a width of 22 cm and a depth of 6 cIII with sterilized diluvial soil, sow grasshoppers, cyperus, cyperus, japonica, chinensis, japonica, and cotton, and cover with soil to a depth of about 1.5 cm. It was evenly distributed over the soil surface at the same ratio. The chemical solution used for spraying was the liquid formulation, wettable powder, emulsion or flowable formulation of the formulation example described above, which was diluted with water and sprayed over the entire surface using a small sprayer. After 4 weeks between the chemical solution + It cloth, the herbicidal effect on seed weeds was investigated according to the following criteria.
判定基準
訃・・殺草率９０％以上（殆ど完全枯死）４・・・殺草
率７０〜９０％
３・・・殺草率４０〜７０％
２・・・殺草率２０〜４０％
１・・・殺草率 ５〜２０％
０・・・殺草率 ５％以下（殆ど効力なし）但し、上記
の殺草率は、薬剤処理区の地上部生草重及び無処理区の
地上部生草重を測定して下記の式により求めたものであ
る。Judgment criteria Mortality: Weed killing rate 90% or more (almost complete death) 4... Weed killing rate 70-90% 3... Weed killing rate 40-70% 2... Weed killing rate 20-40% 1... Killing Grass rate 5-20% 0...Weed killing rate 5% or less (almost ineffective) However, the above weed killing rate is based on measuring the above-ground grass weight in the chemical treated area and the above-ground grass weight in the untreated area. It was calculated using the following formula.
２〜３葉期に達したとき、有効成分量が所定の割合とな
るように菫葉部へ均一に散布した。When the 2nd to 3rd leaf stage was reached, the amount of active ingredient was uniformly sprayed onto the violet leaves at a predetermined ratio.
散布の際の薬液は、前記配合例の液剤、水和剤、乳剤又
はフロアブル剤を水で希釈して小型スプレーで各種雑草
及び作物の菫葉部の全面に散布した。The chemical solution used for spraying was the liquid formulation, wettable powder, emulsion or flowable formulation of the formulation example described above, which was diluted with water and sprayed over the entire surface of the violet leaves of various weeds and crops using a small sprayer.
薬液散布４週間後に各種雑草に対する除草効果を試験例
１の判定基準に従い調査した。結果を第４表に示す。Four weeks after spraying the chemical solution, the herbicidal effect on various weeds was investigated according to the criteria of Test Example 1. The results are shown in Table 4.
結果を第３表に示す。The results are shown in Table 3.
試用■ｌ 苗葉処理による除草効果試験縦３０ＣＩＩ＋
、横２２ｃ＋ｍ、深さ５ｃｍのプラスチック製箱に殺菌
した洪積土壌を入れ、ノビエ、メヒシバ、カラスムギ、
カヤツリグサ、イヌホーズキ、イヌガラシ、ハキダメギ
クの種子をそれぞれスポット状に播種し、約１．５ ｃ
ｔａ覆土した。各種植物がＮｏ、 Ｘ’
ｔ
１
Ｙ” Ｒ
ｌ
２
第１表
恥。Trial■l Weeding effect test by seedling leaf treatment Vertical 30CII+
, Put sterilized diluvial soil in a plastic box with a width of 22 cm + m and a depth of 5 cm.
Seeds of cyperus japonica, cyperus japonica, cyperus japonica, and cyperus japonica were sown in spots, and the seedlings were about 1.5 c.
It was covered with ta soil. Various plants are No.
Ｘｌ ×２ １ ２ １ ２ Ｎｏ。Xl ×2 1 2 1 2 No.
×１ ２ ｌ Ｙ！ １ ２ Ｎｏ。×1 2 l Y! 1 2 No.
Ｘｌ ｔ １ ２ Ｒ’ ２ Ｎｏ。Xl t 1 2 R' 2 No.
ＸＩ ｔ ｌ ｆｆｉ １ ２ Ｎｏ。XI t l ffi 1 2 No.
ＸＩ ×２ ｌ ２ Ｎｏ。XI ×2 l 2 No.
２ １ ２ １ ２ １ ２ Ｎｏ。2 1 2 1 2 1 2 No.
ＸＩ ２ Ｙ’ ２ Ｎｏ。XI 2 Y' 2 No.
ｌ ×２ １ ２ １ ２ １ ２ Ｎｏ。l ×2 1 2 1 2 1 2 No.
×１ ×２ ｌ ２ Ｎｏ。×1 ×2 l 2 No.
×１ ｔ １ ２ １ ｔ １ ２ Ｎｏ。×1 t 1 2 1 t 1 2 No.
Ｉ
２
１
２
１
２
上記第１表において（＋）は光学活性体で右旋イ生を表
し、（−）は左旋性を表す。陶はメチル基、Ｅｌはエチ
ル基、Ｐｒはプロピル基、’Ｐｒはイソプロピル基、ｔ
ｆｌｕはターシャリ−ブチル基、Ｐｈはフェニール基を
表す。I 2 1 2 1 2 In Table 1 above, (+) represents an optically active substance with dextrorotation, and (-) represents levorotation. Ceramic is a methyl group, El is an ethyl group, Pr is a propyl group, 'Pr is an isopropyl group, t
flu represents a tertiary-butyl group, and Ph represents a phenyl group.
（以下余白）
０５
有の ノ
動部 ビ
成理 工
分量
ｇ／アール
２５．０
６．３ ５ ５ ４ ５ ５ ４１２．５
５ ５ ５ ５ ５ ５２５．０ ５
５ ５ ５ ５ ５第
表
物 性 値
１．４０９５ ［ｃｙｌ ｏ””
１．４９１５ ［α］、２３°３
１．４８９０ ［ｃｙｌ ｏ”・４
１．４８７３ ［α］ Ｉｌ！！、４１．４８６４
７６．０〜８０．０℃
１．４５３５
６１．０〜詔、０℃
１．４８７８
５７．０−６１．０℃
１．４８２３
５．０〜５８．０℃
６５、Ｇ〜７０．０℃
１．８
＋１２．８３ （Ｃ＝１．０９１ ＣｌＩＣ１３）−１
３，６１（Ｃ＝１．１０９ ＣｌＩＣｌ５）＋ ６．１
８ （Ｃ＝１．０９９ ＣｌＩＣｌ５）６．２７（Ｃ＝
１．０７４ Ｃ）ＩＣＩ：ｌ）第４
表
０５
ｇ／７−ル
２５．０
３
２５．０
５３、
ギ グ ズ ギ
サ キ り
５
２
４
３(Leaving space below) 05 Existing moving part construction work amount g/are 25.0 6.3 5 5 4 5 5 412.5
5 5 5 5 5 525.0 5
5 5 5 5 5 Table Physical Properties Value 1.4095 [cyl o”” 1.4915 [α], 23°3 1.4890 [cyl o”・4 1.4873 [α] Il!!, 41.4864 76.0~80.0℃ 1.4535 61.0~Yoshi, 0℃ 1.4878 57.0~61.0℃ 1.4823 5.0~58.0℃ 65, G~70.0℃ 1 .8 +12.83 (C=1.091 ClIC13)-1
3,61 (C=1.109 ClICl5) + 6.1
8 (C=1.099 ClICl5) 6.27 (C=
1.074 C) ICI: l) Table 4 05 g/7-ru 25.0 3 25.0 53, gigs 5 2 4 3
Claims (2)
ル基（この置換基としてはハロゲン原子、低級アルコキ
シ基、低級アルキルチオ基或いはハロゲン原子、低級ア
ルキル基、低級アルコキシ基、低級アルキルチオ基で置
換していてもよいフェニル基を示す。）、アルカリ金属
、アルカリ土類金属もしくは置換されていてもよいアン
モニウムカチオンを表す。 Ｒ＾１、Ｒ＾２は各々同一又は相異なってもよく、ハロ
ゲン原子、低級アルキル基、低級ハロアルキル基、低級
アルコキシ基、低級ハロアルコキシ基もしくは低級ジア
ルキルアミノ基を表す。 Ｘ＾１、Ｘ＾２、Ｙ＾１およびＹ＾２は各々同一又は相
異なってもよく、水素原子、シアノ基、カルボキシル基
、低級アルコキシカルボニル基、ホルミル基、低級アル
コキシ基、置換していてもよい低級アルキル基（この置
換基としてはハロゲン原子、シアノ基、ニトロ基、ホル
ミル基、低級アルコキシ基、低級アルキルチオ基、カル
ボキシル基、低級アルコキシカルボニル基、低級ジアル
キルアミノ基、フェニル基、フェノキシ基あるいはフェ
ニルチオ基を示す。）、置換していてもよい低級アルケ
ニル基（この置換基としてはハロゲン原子、シアノ基、
ニトロ基、ホルミル基、低級アルコキシ基、カルボキシ
ル基、低級アルコキシカルボニル基、フェニル基もしく
はフェノキシ基を示す。）、置換していてもよいフェニ
ル基（この置換基としてはハロゲン原子、シアノ基、ニ
トロ基、低級アルキル基、低級アルコキシ基、カルボキ
シル基あるいは低級アルコキシカルボニル基を示す。）
を表す。〕で表されるピリミジン誘導体もしくは該誘導
体の光学異性体。(1) General formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. group, a lower alkylthio group, or a phenyl group optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkylthio group), an alkali metal, an alkaline earth metal, or an optionally substituted ammonium cation. represents. R^1 and R^2 may be the same or different, and represent a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, or a lower dialkylamino group. X^1, X^2, Y^1 and Y^2 may be the same or different, and each may be a hydrogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a formyl group, a lower alkoxy group, or a substituted A lower alkyl group (such substituents include a halogen atom, a cyano group, a nitro group, a formyl group, a lower alkoxy group, a lower alkylthio group, a carboxyl group, a lower alkoxycarbonyl group, a lower dialkylamino group, a phenyl group, a phenoxy group, or phenylthio group), an optionally substituted lower alkenyl group (this substituent includes a halogen atom, a cyano group,
It represents a nitro group, formyl group, lower alkoxy group, carboxyl group, lower alkoxycarbonyl group, phenyl group or phenoxy group. ), an optionally substituted phenyl group (this substituent includes a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower alkoxy group, a carboxyl group, or a lower alkoxycarbonyl group).
represents. ] A pyrimidine derivative or an optical isomer of the derivative.
誘導体の光学異性体の１種又は２種以上を有効成分とし
て含有する除草剤。(2) A herbicide containing as an active ingredient one or more of the pyrimidine derivative or optical isomer of the derivative according to claim (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16494289A JPH0331266A (en) | 1989-06-27 | 1989-06-27 | Pyrimidine derivative and herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16494289A JPH0331266A (en) | 1989-06-27 | 1989-06-27 | Pyrimidine derivative and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0331266A true JPH0331266A (en) | 1991-02-12 |
Family
ID=15802779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16494289A Pending JPH0331266A (en) | 1989-06-27 | 1989-06-27 | Pyrimidine derivative and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0331266A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5228315A (en) * | 1990-12-28 | 1993-07-20 | Zexel Corporation | Condenser having a receiver tank formed integrally therewith |
| 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 |
| US5459194A (en) * | 1994-05-31 | 1995-10-17 | Dow Corning Corporation | Compositions for bonding organosiloxane elastomers to organic polymers |
| KR100502361B1 (en) * | 1998-06-19 | 2005-09-30 | 한라공조주식회사 | Refrigerant filter fastening device |
| US7109205B2 (en) | 1994-10-14 | 2006-09-19 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| DE102011011357A1 (en) | 2010-02-16 | 2011-08-18 | Showa Denko K.K., Tokyo | capacitor |
| DE102011013519A1 (en) | 2010-03-10 | 2011-09-15 | Showa Denko K.K. | capacitor |
| DE102011007749A1 (en) | 2010-04-20 | 2011-10-20 | Showa Denko K.K. | Condenser for use in vehicle air conditioning apparatus, has tank comprising branch control device that conveys flux from coolant in fluid state of tank into pipe for forming coolant undercooling path |
| US8708037B2 (en) | 2010-04-16 | 2014-04-29 | Showa Denko K.K. | Condenser |
-
1989
- 1989-06-27 JP JP16494289A patent/JPH0331266A/en active Pending
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5228315A (en) * | 1990-12-28 | 1993-07-20 | Zexel Corporation | Condenser having a receiver tank formed integrally therewith |
| US5459194A (en) * | 1994-05-31 | 1995-10-17 | Dow Corning Corporation | Compositions for bonding organosiloxane elastomers to organic polymers |
| US7582647B2 (en) | 1994-10-14 | 2009-09-01 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| USRE42477E1 (en) | 1994-10-14 | 2011-06-21 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US7119097B2 (en) | 1994-10-14 | 2006-10-10 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and their use |
| US8349843B2 (en) | 1994-10-14 | 2013-01-08 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US7601730B2 (en) | 1994-10-14 | 2009-10-13 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US7863445B2 (en) | 1994-10-14 | 2011-01-04 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| USRE42462E1 (en) | 1994-10-14 | 2011-06-14 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| US7109205B2 (en) | 1994-10-14 | 2006-09-19 | Abbott Gmbh & Co. Kg | Carboxylic acid derivatives, their preparation and use |
| KR100502361B1 (en) * | 1998-06-19 | 2005-09-30 | 한라공조주식회사 | Refrigerant filter fastening device |
| DE102011011357A1 (en) | 2010-02-16 | 2011-08-18 | Showa Denko K.K., Tokyo | capacitor |
| DE102011013519A1 (en) | 2010-03-10 | 2011-09-15 | Showa Denko K.K. | capacitor |
| US8708037B2 (en) | 2010-04-16 | 2014-04-29 | Showa Denko K.K. | Condenser |
| US8783335B2 (en) | 2010-04-16 | 2014-07-22 | Showa Denko K.K. | Condenser |
| US8839847B2 (en) | 2010-04-16 | 2014-09-23 | Showa Denko K.K. | Condenser |
| DE102011007749A1 (en) | 2010-04-20 | 2011-10-20 | Showa Denko K.K. | Condenser for use in vehicle air conditioning apparatus, has tank comprising branch control device that conveys flux from coolant in fluid state of tank into pipe for forming coolant undercooling path |
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