LT3663B - Pyridine derivatives, process for their production, herbicidal method and composition - Google Patents

Pyridine derivatives, process for their production, herbicidal method and composition Download PDF

Info

Publication number: LT3663B
Authority: LT; Lithuania
Prior art keywords: group; salt; formula; bis; oxy
Prior art date: 1987-12-22

Application number

LTIP830A

Other languages

English (en)

Lithuanian (lt)

Inventor

Nobuhide Wada

Shoji Kusano

Yasuhumi Toyokawa

Original Assignee

Kumiai Chemical Industry Co

Ihara Chemical Ind Co

Priority date (The priority date 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 date listed.)

1987-12-22

Filing date

1993-08-03

Publication date

1996-01-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=18171590&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LT3663(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1993-08-03 Application filed by Kumiai Chemical Industry Co, Ihara Chemical Ind Co filed Critical Kumiai Chemical Industry Co

1995-02-27 Publication of LTIP830A publication Critical patent/LTIP830A/xx

1996-01-25 Publication of LT3663B publication Critical patent/LT3663B/lt

Links

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
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240000003461 Setaria viridis Species 0.000 description 2
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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
244000202761 Sorghum bicolor subsp verticilliflorum Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
235000010724 Wisteria floribunda Nutrition 0.000 description 2
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
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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
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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
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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
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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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
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238000003756 stirring Methods 0.000 description 2
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239000004094 surface-active agent Substances 0.000 description 2
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Classifications

- 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)

LTIP830A 1987-12-22 1993-08-03 Pyridine derivatives, process for their production, herbicidal method and composition LT3663B (en)

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)

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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
CN105052938B (zh) *	2007-08-27	2017-12-01	陶氏益农公司	含某些吡啶羧酸或嘧啶羧酸和某些谷物和稻除草剂的协同性除草组合物
EP2052608A1 (de)	2007-10-24	2009-04-29	Bayer CropScience AG	Herbizid-Kombination
JP5406032B2 (ja) *	2007-10-26	2014-02-05	クミアイ化学工業株式会社	サトウキビ用糖度向上剤及びこれを用いたサトウキビの登熟促進方法
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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
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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 KR KR1019880017153A patent/KR960007527B1/ko not_active Expired - Lifetime
- 1988-12-21 US US07/287,056 patent/US4906285A/en not_active Expired - Lifetime
- 1988-12-21 RU SU884613101A patent/RU1807848C/ru active
- 1988-12-21 UA UA4613101A patent/UA26890C2/uk unknown
- 1988-12-22 CN CN88108904A patent/CN1024664C/zh 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
- 1988-12-30 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 CN92112271A patent/CN1033200C/zh not_active Expired - Lifetime
- 1992-10-22 CN CN92112424A patent/CN1033201C/zh not_active Expired - Lifetime
1993
- 1993-08-03 LT LTIP830A patent/LT3663B/lt not_active IP Right Cessation

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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
EP0321846A2 (de)	1989-06-28
AU2691488A (en)	1989-06-22
CN1033200C (zh)	1996-11-06
EP0321846B1 (de)	1995-04-19
CN1071550A (zh)	1993-05-05
RU2028294C1 (ru)	1995-02-09
KR890009914A (ko)	1989-08-04
KR960007527B1 (ko)	1996-06-05
DE3853622T2 (de)	1996-01-11
AU610311B2 (en)	1991-05-16
CN1035292A (zh)	1989-09-06
ES2074433T3 (es)	1995-09-16
EG18666A (en)	1994-04-30
CN1033201C (zh)	1996-11-06
UA26890C2 (uk)	1999-12-29
EP0321846A3 (en)	1990-03-28
DE3853622D1 (de)	1995-05-24
LTIP830A (en)	1995-02-27
PH25156A (en)	1991-03-27
JPH01250365A (ja)	1989-10-05
JP2558516B2 (ja)	1996-11-27
US5081244A (en)	1992-01-14
BR8806801A (pt)	1989-08-29
RU1807848C (ru)	1993-04-07
US4906285A (en)	1990-03-06
CN1024664C (zh)	1994-05-25
CN1072313A (zh)	1993-05-26

Legal Events

Date	Code	Title	Description
2013-09-25	MK9A	Expiry of a patent	Effective date: 20130803

Publication	Publication Date	Title
LT3663B (en)	1996-01-25	Pyridine derivatives, process for their production, herbicidal method and composition
RU2049781C1 (ru)	1995-12-10	Производные пиримидина
DE69125667T2 (de)	1997-09-25	Pyrimidin-Derivate und diese enthaltende herbizide Zusammensetzungen
CZ282275B6 (cs)	1997-06-11	Substituované deriváty pyrimidinu, způsob jejich výroby, meziprodukty pro jejich výrobu pesticidní prostředek a způsob hubení škůdců a zvířecích ektoparasitů
WO2010139271A1 (zh)	2010-12-09	含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用
JPH06128237A (ja)	1994-05-10	新規な除草有効性ｎ−（シクロプロピル−トリアジニル−および−ピリミジニル）−ｎ’−（アリールスルホニル）尿素の中間体として有用な２−アミノ−４−シクロプロピル−（ピリミジンおよび１，３，５−トリアジン）
HU187389B (en)	1985-12-28	Herbicide compositions and process for preparing tiazoline derivatives
EP0517215B1 (de)	1998-09-02	Pyrimidin- oder Triazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
EP0739341A1 (de)	1996-10-30	Aryl- und heteroaryl- pyrimidine als herbizide
CA2052263C (en)	2002-05-07	Herbicides
EP0481512A1 (de)	1992-04-22	3-Alkoxyalkansäure Derivate, Verfahren zu deren Herstellung und diese benützende Herbizide
DE68919731T2 (de)	1995-07-06	Pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende herbizide Zusammensetzungen.
JPH04235171A (ja)	1992-08-24	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
IL96114A (en)	1995-08-31	Insecticidal miticidal and nematocidal compositions containing 3-arylpyrimidinyl ethers and theioethers and some such novel compounds and processes for the preparation thereof
JPS61236766A (ja)	1986-10-22	ｏ−置換フエノキシ複素環化合物、その製造法およびそれを有効成分とする除草剤
JPH0421672B2 (de)	1992-04-13
US5426090A (en)	1995-06-20	Heterocyclic compounds
EP0493321A1 (de)	1992-07-01	Pyrimidinyl- und Triazinyl-salicylamide sowie deren Verwendung und Herstellung
US4846882A (en)	1989-07-11	Herbicidal aryl tetrahydrophthalimides
JP2730021B2 (ja)	1998-03-25	３−ベンジルオキシアルカン酸誘導体、その製造法及び除草剤
EP0567014B1 (de)	1995-07-12	Sulfonamidderivate, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
JP2730022B2 (ja)	1998-03-25	３−アルコキシブチリルイミダゾール誘導体、その製造法及び除草剤
JPH07112972A (ja)	1995-05-02	ピラゾールカルボキサミド誘導体、その製法及び農園芸用の有害生物防除剤
JP2985992B2 (ja)	1999-12-06	３−アルコキシ−ｎ−シクロアルキルスルホニルアルカン酸アミド誘導体、その製造法及び除草剤
DE60102893T2 (de)	2005-03-31	Extrudierter polytetrafluorethylenschaum