LT3663B - Pyridine derivatives, process for their production, herbicidal method and composition - Google Patents
Pyridine derivatives, process for their production, herbicidal method and composition Download PDFInfo
- Publication number
- LT3663B LT3663B LTIP830A LTIP830A LT3663B LT 3663 B LT3663 B LT 3663B LT IP830 A LTIP830 A LT IP830A LT IP830 A LTIP830 A LT IP830A LT 3663 B LT3663 B LT 3663B
- Authority
- LT
- Lithuania
- Prior art keywords
- group
- salt
- formula
- bis
- oxy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 67
- 230000002363 herbicidal effect Effects 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003222 pyridines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 91
- -1 alkali metal salt Chemical class 0.000 claims description 55
- 241000196324 Embryophyta Species 0.000 claims description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- RYVIXQCRCQLFCM-UHFFFAOYSA-N bispyribac Chemical group COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(O)=O)=N1 RYVIXQCRCQLFCM-UHFFFAOYSA-N 0.000 claims description 5
- AKEUNCKRJATALU-UHFFFAOYSA-N gamma-resorcylic acid Natural products OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- 239000000843 powder Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 238000009736 wetting Methods 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 240000007594 Oryza sativa Species 0.000 description 15
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 235000009566 rice Nutrition 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- 239000004009 herbicide Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 239000002689 soil Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 229920001732 Lignosulfonate Polymers 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 244000098338 Triticum aestivum Species 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 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 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 3
- 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
- 241000132536 Cirsium Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NVFYWVGJQFRNND-UHFFFAOYSA-N 2-(4-chloro-6-methoxypyrimidin-2-yl)oxy-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid Chemical compound COC1=CC(Cl)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(O)=O)=N1 NVFYWVGJQFRNND-UHFFFAOYSA-N 0.000 description 2
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 description 2
- CMOSHHAKKLXTTK-UHFFFAOYSA-N 2-trimethylsilylethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)oxy-6-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate Chemical compound COC1=CC(Cl)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)OCC[Si](C)(C)C)=N1 CMOSHHAKKLXTTK-UHFFFAOYSA-N 0.000 description 2
- 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
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- DMNJKRNLPLOTAG-UHFFFAOYSA-N 4-chloro-6-methoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(Cl)=NC(S(C)(=O)=O)=N1 DMNJKRNLPLOTAG-UHFFFAOYSA-N 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 241000272201 Columbiformes Species 0.000 description 2
- 235000016854 Cyperus rotundus Nutrition 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 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 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- 235000017879 Nasturtium officinale Nutrition 0.000 description 2
- 240000005407 Nasturtium officinale Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 241000124033 Salix Species 0.000 description 2
- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- 239000004178 amaranth Substances 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- OTHQLUSOEGXJEA-UHFFFAOYSA-N benzyl 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)OCC=2C=CC=CC=2)=N1 OTHQLUSOEGXJEA-UHFFFAOYSA-N 0.000 description 2
- UONCJNZKQVIGHS-UHFFFAOYSA-N benzyl 2,6-dihydroxybenzoate Chemical compound OC1=CC=CC(O)=C1C(=O)OCC1=CC=CC=C1 UONCJNZKQVIGHS-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229920005646 polycarboxylate Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium 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
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32496487 | 1987-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP830A LTIP830A (en) | 1995-02-27 |
| LT3663B true LT3663B (en) | 1996-01-25 |
Family
ID=18171590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP830A LT3663B (en) | 1987-12-22 | 1993-08-03 | Pyridine derivatives, process for their production, herbicidal method and composition |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US4906285A (de) |
| EP (1) | EP0321846B1 (de) |
| JP (1) | JP2558516B2 (de) |
| KR (1) | KR960007527B1 (de) |
| CN (3) | CN1024664C (de) |
| AU (1) | AU610311B2 (de) |
| BR (1) | BR8806801A (de) |
| DE (1) | DE3853622T2 (de) |
| EG (1) | EG18666A (de) |
| ES (1) | ES2074433T3 (de) |
| LT (1) | LT3663B (de) |
| PH (1) | PH25156A (de) |
| RU (2) | RU1807848C (de) |
| UA (1) | UA26890C2 (de) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5125957A (en) * | 1989-11-01 | 1992-06-30 | Sumitomo Chemical Company, Limited | Pyrimidine derivatives |
| US5340811A (en) * | 1990-03-08 | 1994-08-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Isoquinoline-or quinoline-sulfonamide derivative and a pharmaceutical composition comprising the same |
| JPH04235171A (ja) * | 1990-07-26 | 1992-08-24 | Sumitomo Chem Co Ltd | スルホヒドロキサム酸誘導体、その製造法およびそれを有効成分とする除草剤 |
| US5298632A (en) * | 1990-05-15 | 1994-03-29 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| US5232897A (en) * | 1990-05-15 | 1993-08-03 | Sumitomo Chemical Company, Limited | Herbicidal pyrimidine compounds, compositions containing the same and method of use |
| AU638840B2 (en) * | 1990-07-05 | 1993-07-08 | Sumitomo Chemical Company, Limited | Pyrimidine derivative |
| JPH04103574A (ja) * | 1990-08-22 | 1992-04-06 | Kumiai Chem Ind Co Ltd | ピリミジン誘導体及び除草剤 |
| DE4030041A1 (de) * | 1990-09-22 | 1992-03-26 | Bayer Ag | Bisazinylverbindungen |
| DE4211610A1 (de) * | 1992-04-07 | 1993-10-14 | Bayer Ag | Substituierte Azine |
| DE4217928A1 (de) * | 1992-05-30 | 1993-12-02 | Hoechst Ag | Neue Mischungen aus Herbiziden und Antidots, neue (Hetero-)Aryloxy-Verbindungen, Verfahren zu deren Herstellung, diese enthaltenden Mittel und deren Verwendung |
| CN1101345A (zh) * | 1993-01-27 | 1995-04-12 | 株式会社乐喜 | 具有除草作用的嘧啶衍生物，它们的生产方法及应用 |
| US5521146A (en) * | 1993-11-13 | 1996-05-28 | Lucky Ltd. | Herbicidal pyrimidine derivatives, process for preparation thereof and their use as herbicide |
| KR100376173B1 (ko) * | 1995-07-20 | 2003-08-19 | 주식회사 엘지생명과학 | 벤질리딘아미노에스테르구조를갖는제초성피리미딘화합물의제조방법 |
| KR100380145B1 (ko) * | 1995-12-27 | 2003-08-14 | 주식회사 엘지생명과학 | 피리미딜옥시벤조산옥심에스테르의신규한제조방법 |
| SG63694A1 (en) * | 1996-03-07 | 1999-03-30 | American Cyanamid Co | Process for the preparation of unsymmetrical 4,6-bis (aryloxy) pyrimidine compounds |
| DE10142336A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide enthaltend ein Tetrazolinon-Derivat |
| CN1208325C (zh) * | 2003-07-04 | 2005-06-29 | 中国科学院上海有机化学研究所 | 2－嘧啶氧基－n－脲基苯基苄胺类化合物、制备方法及其用途 |
| EP1836894A1 (de) | 2006-03-25 | 2007-09-26 | Bayer CropScience GmbH | Neue Sulfonamid-haltige feste Formulungen |
| DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
| EP1844654A1 (de) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetrationsförderer für agrochemische Wirkstoffe |
| US20090062121A1 (en) * | 2007-08-27 | 2009-03-05 | Dow Agrosciences Llc | Synergistic herbicidal composition containing certain pyridine or pyrimidine carboxylic acids and certain cereal and rice herbicides |
| EP2052608A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| AU2008314934A1 (en) * | 2007-10-26 | 2009-04-30 | Kumiai Chemical Industry Co., Ltd. | Agent for improving sugarcane brix and method of promoting sugarcane ripening using the same |
| EP2064953A1 (de) | 2007-11-29 | 2009-06-03 | Bayer CropScience AG | Herbizid-Azol-Kombination |
| CN101265235B (zh) * | 2008-05-08 | 2012-04-25 | 上海交通大学 | 除草剂双草醚的制备方法 |
| DE102008037631A1 (de) * | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
| RU2440731C2 (ru) * | 2010-02-24 | 2012-01-27 | Юрий Аглямович Гарипов | Суспензионный концентрат гербицидной композиции и способ его получения |
| HRP20211509T1 (hr) | 2010-10-15 | 2021-12-24 | Bayer Cropscience Aktiengesellschaft | Upotreba herbicida inhibitora als za suzbijanje neželjene vegetacije u biljkama beta vulgaris tolerantnim na herbicide inhibitore als |
| CN102461558A (zh) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | 一种含双草醚和莎稗磷的混合除草组合物 |
| CN102461547B (zh) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | 一种含醚磺隆、双草醚与环庚草醚的混合除草剂及其应用 |
| CN102461531B (zh) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | 一种含醚磺隆、双草醚与氰氟草酯的混合除草剂及其应用 |
| CN102461544B (zh) * | 2010-11-19 | 2013-08-07 | 南京华洲药业有限公司 | 一种含醚磺隆、灭草松与双草醚的混合除草剂及其应用 |
| CN102461521B (zh) * | 2010-11-19 | 2014-03-05 | 南京华洲药业有限公司 | 一种含双草醚和噁嗪草酮的混合除草组合物 |
| CN102461527A (zh) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | 一种含双草醚和禾草丹的混合除草组合物 |
| CN102461545B (zh) * | 2010-11-19 | 2014-04-16 | 南京华洲药业有限公司 | 一种含双草醚和环丙嘧磺隆的混合除草组合物 |
| CN102461548B (zh) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | 一种含醚磺隆、双草醚与禾草敌的混合除草剂及其应用 |
| CN102461552B (zh) * | 2010-11-19 | 2013-11-27 | 南京华洲药业有限公司 | 一种含醚磺隆、双草醚与二甲戊乐灵的混合除草剂及其应用 |
| CN102461554A (zh) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | 一种含双草醚和吡嘧磺隆的混合除草组合物 |
| CN102461507B (zh) * | 2010-11-19 | 2013-12-25 | 南京华洲药业有限公司 | 一种含双草醚和乙草胺的混合除草组合物及其应用 |
| CN102461543A (zh) * | 2010-11-19 | 2012-05-23 | 南京华洲药业有限公司 | 一种含双草醚和醚磺隆的混合除草组合物 |
| AU2012251597B2 (en) | 2011-05-04 | 2015-11-05 | Bayer Intellectual Property Gmbh | Use of ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant Brassica, such as B. napus, plants |
| CN102415388A (zh) * | 2011-11-07 | 2012-04-18 | 广东中迅农科股份有限公司 | 一种环保高效水稻田除草剂及其制备方法 |
| RS57806B2 (sr) | 2012-12-13 | 2022-07-29 | Bayer Cropscience Ag | Upotreba als inhibitora herbicida za kontrolu neželjene vegetacije kod beta vulgaris biljaka tolerantnih na als inhibitore herbicida |
| CN105026376B (zh) * | 2013-02-18 | 2018-05-11 | 加尔达化学有限公司 | 用于制备双草醚钠及其中间体的方法 |
| CN105272924B (zh) * | 2013-07-22 | 2016-08-17 | 金坛市信德农业科技有限公司 | 具有除草活性的氟嘧啶草醚类化合物及其制备方法 |
| CN104396954A (zh) * | 2014-03-29 | 2015-03-11 | 潍坊先达化工有限公司 | 含有2,4-二氯苯氧丁酸及其衍生物的除草剂组合物 |
| CN107311982A (zh) * | 2017-06-26 | 2017-11-03 | 杨子辉 | 一种双草醚衍生物及其制备方法与应用 |
| WO2019244088A1 (en) | 2018-06-21 | 2019-12-26 | Pi Industries Ltd. | Agrochemical composition comprising a pyrimidyloxybenzoate in a synergistic combination with sulfonylureas |
| US20240401073A1 (en) | 2021-10-15 | 2024-12-05 | KWS SAAT SE & Co. KGaA | Als inhibitor herbicide tolerant beta vulgaris mutants |
| CN115124477B (zh) * | 2022-08-08 | 2024-05-10 | 中国农业大学 | 一类新型嘧啶水杨酸酚酯、其合成方法及作为除草剂的应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4248619A (en) | 1978-08-08 | 1981-02-03 | Ici Australia Limited | Bis[pyrimidyloxy(thio)]benzene derivatives |
| US4427437A (en) | 1977-09-13 | 1984-01-24 | Ici Australia Limited | Use of 2-phenoxypyrimidines as herbicides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH082883B2 (ja) * | 1986-06-06 | 1996-01-17 | クミアイ化学工業株式会社 | ２−フエノキシピリミジン誘導体および除草剤 |
-
1988
- 1988-12-14 DE DE3853622T patent/DE3853622T2/de not_active Expired - Lifetime
- 1988-12-14 EP EP88120917A patent/EP0321846B1/de not_active Expired - Lifetime
- 1988-12-14 ES ES88120917T patent/ES2074433T3/es not_active Expired - Lifetime
- 1988-12-15 AU AU26914/88A patent/AU610311B2/en not_active Expired
- 1988-12-20 JP JP63322714A patent/JP2558516B2/ja not_active Expired - Lifetime
- 1988-12-21 UA UA4613101A patent/UA26890C2/uk unknown
- 1988-12-21 RU SU884613101A patent/RU1807848C/ru active
- 1988-12-21 KR KR1019880017153A patent/KR960007527B1/ko not_active Expired - Lifetime
- 1988-12-21 US US07/287,056 patent/US4906285A/en not_active Expired - Lifetime
- 1988-12-22 BR BR888806801A patent/BR8806801A/pt not_active Application Discontinuation
- 1988-12-22 PH PH37967A patent/PH25156A/en unknown
- 1988-12-22 CN CN88108904A patent/CN1024664C/zh not_active Expired - Lifetime
- 1988-12-30 EG EG64588A patent/EG18666A/xx active
-
1989
- 1989-12-22 US US07/454,937 patent/US5081244A/en not_active Expired - Lifetime
-
1992
- 1992-02-20 RU SU925011097A patent/RU2028294C1/ru active
- 1992-10-22 CN CN92112424A patent/CN1033201C/zh not_active Expired - Lifetime
- 1992-10-22 CN CN92112271A patent/CN1033200C/zh not_active Expired - Lifetime
-
1993
- 1993-08-03 LT LTIP830A patent/LT3663B/lt not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427437A (en) | 1977-09-13 | 1984-01-24 | Ici Australia Limited | Use of 2-phenoxypyrimidines as herbicides |
| US4248619A (en) | 1978-08-08 | 1981-02-03 | Ici Australia Limited | Bis[pyrimidyloxy(thio)]benzene derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2691488A (en) | 1989-06-22 |
| DE3853622D1 (de) | 1995-05-24 |
| CN1033201C (zh) | 1996-11-06 |
| EP0321846B1 (de) | 1995-04-19 |
| CN1072313A (zh) | 1993-05-26 |
| US5081244A (en) | 1992-01-14 |
| EG18666A (en) | 1994-04-30 |
| JPH01250365A (ja) | 1989-10-05 |
| PH25156A (en) | 1991-03-27 |
| RU1807848C (ru) | 1993-04-07 |
| RU2028294C1 (ru) | 1995-02-09 |
| BR8806801A (pt) | 1989-08-29 |
| UA26890C2 (uk) | 1999-12-29 |
| KR960007527B1 (ko) | 1996-06-05 |
| KR890009914A (ko) | 1989-08-04 |
| CN1035292A (zh) | 1989-09-06 |
| US4906285A (en) | 1990-03-06 |
| LTIP830A (en) | 1995-02-27 |
| DE3853622T2 (de) | 1996-01-11 |
| ES2074433T3 (es) | 1995-09-16 |
| CN1024664C (zh) | 1994-05-25 |
| JP2558516B2 (ja) | 1996-11-27 |
| EP0321846A2 (de) | 1989-06-28 |
| AU610311B2 (en) | 1991-05-16 |
| CN1033200C (zh) | 1996-11-06 |
| EP0321846A3 (en) | 1990-03-28 |
| CN1071550A (zh) | 1993-05-05 |
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| Date | Code | Title | Description |
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| MK9A | Expiry of a patent |
Effective date: 20130803 |