CN1304932A - 制备1,4-二取代的四唑啉酮的中间体 - Google Patents
制备1,4-二取代的四唑啉酮的中间体 Download PDFInfo
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- CN1304932A CN1304932A CN00121913A CN00121913A CN1304932A CN 1304932 A CN1304932 A CN 1304932A CN 00121913 A CN00121913 A CN 00121913A CN 00121913 A CN00121913 A CN 00121913A CN 1304932 A CN1304932 A CN 1304932A
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- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 claims description 7
- -1 1,4-disubstituted tetrazolinones Chemical class 0.000 abstract description 29
- 239000000543 intermediate Substances 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 72
- 238000002360 preparation method Methods 0.000 description 33
- 230000002363 herbicidal effect Effects 0.000 description 23
- 230000000694 effects Effects 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000004009 herbicide Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 240000000178 Monochoria vaginalis Species 0.000 description 4
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- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 235000003990 Monochoria hastata Nutrition 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
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- 238000000746 purification Methods 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
Abstract
本发明涉及1,4-二取代的新四唑啉酮制备过程中的新的中间体,下式(Ⅱ)代表的四唑啉酮,式中X代表C1-4烷基,n代表1,2,3或4。
Description
本申请系申请日为1996年3月22日、申请号为96104414.4、发明名称为“新的四唑啉酮”的发明专利申请的分案申请。
本发明涉及1,4-二取代的新四唑啉酮制备过程中的新的中间体。所述1,4-二取代的四唑啉酮作为水田除莠剂表现出特别高的活性。
人们已知某种四唑啉酮衍生物具有除莠活性(参见:日本专利公开昭62-12767号和昭60-146879号;美国专利4956469、5019152和5003075)。
现已发现新的式(Ⅰ)四唑啉酮:式中X代表C1-4烷基,n代表1,2,3或4,R1和R2各自独立地代表C1-6烷基,C2-4链烯基,C2-6炔基,C3-8环烷基,
可任选地被取代的芳基(其中取代基是至少一个选自卤素、C1-4烷
基、C1-2卤代烷基、C1-2卤代烷氧基、C1-2卤代烷硫基、酰基、硝基和
氰基的基团)或可任选地被卤素取代的芳烷基,或者R1和R2可同与之键合的N原子一起形成可任选地被取代的环。
按照本发明的化合物可这样来制备:(a)使式(Ⅱ)化合物在惰性溶剂存在下并且,若合适,在酸结合剂和/或催化剂存在下与式(Ⅲ)化合物反应(=制备方法(a));所述式(Ⅱ)和(Ⅲ)如下:式中X和n的定义同上,式中R1和R2的定义同上,和hal代表离去基团,例如氯,溴等。
按照本发明的式(Ⅰ)化合物具有很强的除莠活性。令人惊讶的是,与日本专利公开昭62-12767号和昭60-146879号及美国专利4956469、5019152和5003075中描述的已知化合物的除莠活性相比,按照本发明的式(Ⅰ)四唑啉酮显示出强得多的除莠活性,特别是,它们是对于水田具有选择生余莠活性的理想化合物,对于水田杂草显示出极佳的除莠活性,而且同时对水稻植物基本上未表现出植物毒性。
在本说明书中,
“烷基”和卤代烷基,卤代烷氧基和卤代烷硫基中的烷基部分是直链的或支链的,包括甲基乙基,正丙基,异丙基,正、异、仲或叔丁基,正己基,正庚基等,并且由碳数限定的烷基和烷基部分可选自上述的基团;
“卤素”和卤代烷基、卤代烷氧基和卤代烷硫基中的卤素部分包括氟、氯、溴和碘,优选氟,氯或溴;
“链烯基”包括乙烯基,1-丙烯基,烯丙基,1-(2-或3-)丁烯基等,优选烯丙基;
“炔基”包括乙炔基,1-丙炔基,炔丙基,1-、2-或3-丁炔基,1-甲基-2-丙炔基,1,1-二甲基-2-丙炔基等,优选炔丙基,1-甲基-2-丙炔基或1,1-二甲基-2-丙炔基;
“酰基”包括烷基羰基,苯甲酰基等,优选乙酰基;
“芳基”包括苯基,萘基等,优选苯基;
“芳烷基”代表芳基取代的烷基,包括苄基,苯乙基等,优选苄基;
“与N原子一起形成的环”包括具有一个N原子的5或6元杂环,或其9或10元烃缩合环,其优选的实例是吡咯烷基,哌啶基,吲哚基,二氢吲哚基,1,2,3,4-四氢喹啉基,1,2-二氢喹啉基等。
在按照本发明的式(Ⅰ)四唑啉酮衍生物中,优选的化合物是式中取代基如下定义的化合物:X代表甲基或乙基,n代表1或2,R1和R2各自独立地代表C1-4烷基,C3-4链烯基,C3-5炔基,环
丙基,环戊基,环己基,可任选地被取代的苯基(其中取代基是至
少一个选自氟、氯、溴、甲基、乙基、正丙基、三氟甲基、二氟甲
氧基、三氟甲氧基、三氟甲硫基、乙酰基、硝基和氰基的基团)或
可任选地被氯取代的苄基,或者R1和R2可同与之键合的N原子一起形成可任选地被甲基取代的5或
6元环,或其苯并稠合的环。
特别优选的式(Ⅰ)四唑啉酮是式中取代基如下定义的化合物:X代表甲基,n代表1或2,R1和R2各自独立地代表乙基,正丙基,异丙基,正丁基,异丁基
仲丁基,烯丙基,炔丙基,1-甲基2-丙炔基,1,1-二甲基-2-丙炔
基,环丙基,环己基,可任选地被取代的苯基(其中取代基是至少
一个选自氟、氯、溴、甲基、三氟甲基、二氟甲氧基、三氟甲氧基、
三氟甲硫基、乙酰基、硝基和氰基的基团)或可任选地被氯取代的
苄基,或者R1和R2可同与之键合的N原子一起形成可任选地被甲基取代的
1,2,3,4-四氢喹啉-1-基或1,2-二氢喹啉-1-基。
在上述的制备方法(a)中,作为原料的式(Ⅱ)化合物是新化合物,通常可例如用下列制备方法(b)至(e)中任一方法来制备:制备方法b):使式(Ⅳ)代表的化合物在催化量的乙醚合三氟化硼存在下与三甲基甲硅烷基叠氮反应,所述式(Ⅳ)如下:式中X和n的定义同上;制备方法c):使上述的式(Ⅳ)代表的化合物在极性溶剂中在催化量的氯化铵存在下与叠氮化钠反应;制备方法(d):使式(Ⅴ)代表的化合物与三甲基甲硅烷基叠氮反应,所述式(Ⅴ)如下:式中X和n的定义同上;或者制备方法(e):使式(Ⅵ)代表的化合物与式(Ⅶ)代表的化合物反应,所述式(Ⅵ)和(Ⅶ)如下:式中X和n的定义同上,式中M是卤原子或甲基。
在上述的制备方法(b)和(c)中,用作原料的式(Ⅳ)化合物包括有机化学领域中公知的异氰酸酯类,可例如用“New ExperimentalChemistry Course(Shin Jikken Kagaku Koza)”由Japanese ChemicalSociety编辑,第14卷,第1490-1503页(由Maruzen在1977年12月20日发行)中所述的方法来合成。
在上述的制备方法(d)中用作原料的式(Ⅴ)化合物包括有机化学领域中公知的酰氯,可用“New Experimental Chemistry Course(ShinJikken Kagaku Koza)”由Japanese Chemical Society编辑,第14卷,第1104-1120页(由Maruzen在1977年12月20日发行)中所述的方法来合成。它们可容易地例如通过式(Ⅷ)化合物与作为卤化剂的亚硫酰氯反应来获得;所述式(Ⅷ)如下:式中X和n的定义同上。
此外,上述式(Ⅷ)化合物还可用“New Experimental ChemistryCourse(Shin Jikken Kagalku Koza)”由Japanese Chemical Society编辑,第14卷,第921-1000页(由Maruzen在1977年12月20日发行)中所述的方法来合成。
另外,上述式(Ⅷ)化合物还可以通过将相应的环己烷羧酸酯水解来制备。
在上述的制备方法(e)中用作原料的式(Ⅵ)化合物可例如用Berichte,第28卷,74-76页(1895)中所述的方法来制备,即将式(Ⅹ)代表的化合物与叠氮化钠反应;所述式(Ⅹ)如下:式中X和n的定义同上。
上述式(Ⅹ)二硫代氨基甲酸酯可容易地按下述方法来制备:使甲硫醇与式(Ⅺ)化合物反应,或使式(Ⅻ)代表的化合物与二硫化碳反应,接着再与甲基化剂例如硫酸二甲酯或碘甲烷反应;所述式(Ⅺ)和(Ⅻ)如下:式中X和n的定义同上,式中X和n的定义同上。
上述的式(Ⅺ)化合物可例如按照“New Experimental ChemistryCourse(Shin Jikken Kagalku Koza)”由Japanese Chemical Society编辑,第14卷,第1503-1509页(由Maruzen在1977年12月20日发行)中所述的方法来制备。
此外,式(Ⅻ)化合物可例如按照“New Experimental ChemistryCourse(Shin Jikken Kagaku Koza)”由Japanese Chemical Society编辑,第14卷,第1332-1399页(由Maruzen在1977年12月20日发行)中所述的方法来制备。
在制备方法(e)中用作原料的式(Ⅶ)化合物是本身已知的,可以环氧乙烷或1,2-环氧丙烷为例。
可按上述制得的式(Ⅱ)化合物的典型实例包括下列化合物:1-(1-甲基环己基)-5(4H)-四唑啉酮,1-(2-甲基环已基)-5(4H)-四唑啉酮,1-(3-甲基环己基)-5(4H)-四唑啉酮,1-(4-甲基环己基)-5(4H)-四唑啉酮,1-(2,3-二甲基环己基)-5(4H)-四唑啉酮,1-(2,6-二甲基环己基)-5(4H)-四唑啉酮,1-(3,5-二甲基环己基)-5(4H)-四唑啉酮,1-(2,2-二甲基环己基)-5(4H)-四唑啉酮,1-(4-乙基环己基)-5(4H)-四唑啉酮,1-(3,3,5,5-四甲基环己基)-5(4H)-四唑啉酮,等。
在上述的制备方法(a)中用作原料的式(Ⅲ)化合物是有机化学领域中熟知的,其实例包括下列化合物:二乙基氨基甲酰氯,N-环己基-N-乙基氨基甲酰氯,N-环丙基-N-正丙基氨基甲酰氯,二烯丙基氨基甲酰氯,N-异丙基-N-苯基氨基甲酰氯,N-(2-氟苯基)-N-异丙基氨基甲酰氯,N-环己基-N-异丙基氨基甲酰氯,N-乙基-N-异丙基氨基甲酰氯,N-(4-氯苯基)-N-异丙基氨基甲酰氯,N-异丙基-N-(2-甲基苯基)氨基甲酰氯,2-甲基-1,2,3,4-四氢喹啉-1-基氨基甲酰氯,N-(1-甲基-2-丙炔基)-N-苯基氨基甲酰氯,N-(1,1-二甲基-2-丙炔基)-N-苯基氨基甲酰氯,N-乙基-N-苯基氨基甲酰氯,2,2-二甲基-1,2,3,4-四氢喹啉-1-基碳酰氯,2-甲基-1,2-二氢喹啉-1-基碳酰氯,2,2-二甲基-1,2-二氢喹啉-1-基碳酰氯,等。
上述的制备方法(a)中的反应可在适宜的溶剂、特别是隋性有机溶剂中进行,可用的溶剂的实例是脂族、脂环族和芳族烃类(可任选地被氯化),例如戊烷,己烷,环己烷,石油醚,轻石油,苯,甲苯,二甲苯,二氯甲烷,氯仿,四氯化碳,1,2-二氯乙烷,氯苯和二氯苯;醚类,例如乙醚,甲基乙基醚,二异丙基醚,二丁基醚,二氧六环,二甲氧基乙烷(DME),四氢呋喃(THF)和二甘醇二甲基醚(DGM);腈类,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺(DMF),二甲基乙酰胺(DMA),N-甲基吡咯烷酮,1,3-二甲基-2-咪唑啉酮和六甲基磷三酰胺(HMPA);砜和亚砜类,例如二甲亚砜(DMSO)和四氢噻吩砜;和碱类,例如吡啶。
上述的制备方法a)中的反应可在酸结合剂存在下进行。这样的酸结合剂的实例有无机碱,碱金属的碳酸盐和碳酸氢盐,例如碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾等;和有机碱,叔胺类、二烷基氨基苯胺类和吡啶类,例如三乙胺、1,1,4,4-四甲基乙二胺(TMEDA)、N,N-二甲基苯胺、N,N-二乙基苯胺、吡啶、4-二甲氨基吡啶(DMAP)、1,4-二氮杂二环[2.2.2]辛烷(DABCO)、1,8-二氮杂二环[5.4.0]-十一碳-7-烯(DBU)等。
此外,为选择性合成所需的化合物,可将4-二甲氨基吡啶用作催化剂和/或酸结合剂。
制备方法a)中的反应可在宽的温度范围内进行,但通常宜在约-30℃~200℃温度范围内进行,特别是在大约-20℃~130℃进行。反应应最好在常压下进行,但也可任选地在加压或减压下进行。
制备方法a)可例如这样实施:在1~1.2mol酸结合剂和4-二甲氨基吡啶存在下,将1mol式(Ⅱ)化合物在溶剂例如甲苯中与1~1.2mol式(Ⅲ)化合物反应,由此获得所需的式(Ⅰ)化合物。
按照本发明的式(Ⅰ)化合物正如由后面的试验实施例显示的那样,表现出极佳的除莠活性,因此它们可用作灭杂草的除莠剂、特别是水田的除莠剂。此外还发现:当将按照本发明的式(Ⅰ)化合物作为除莠有效成分与至少一种选自下列的除莠化合物配合使用时能获得具有特别高的除莠活性的除莠组合物:除莠磺酰胺、除莠吡唑、除莠N-丙酰苯胺、除莠三嗪、除莠氨基甲酸酯、除莠二苯醚、除莠嘧啶和除莠酰胺。
在上述的除莠组合物中,可与按照本发明的式(Ⅰ)化合物一起使用的除莠化合物的具体实例如下:除莠磺酰胺:
N-2-联苯基磺酰基-N’-(4,6-二甲氧基-1,3,5-三嗪-2-基)-脲,
5-[3-(4,6-二甲氧基嘧啶-2-基)脲基磺酰基]-1-甲基吡唑-4-羧酸乙酯,
2-[3-(4,6-二甲氧基嘧啶-2-基)脲基磺酰基甲基]苯甲酸甲酯,
3-(4,6-二甲氧基-1,3,5-三嗪-2-基)-1-[2-(2-甲氧基乙氧基)-苯磺酰基]脲,
N-(2-氯咪唑并[1,2-a]吡啶-3-基-磺酰基)-N’-(4,6-二甲氧基-2-嘧啶基)脲,
N’-(4,6-二甲氧基嘧啶-2-基)-N''-(4-甲基苯基磺酰基氨基)-N'''-(4-乙氧基羰基-1-甲基吡唑-5-基-磺酰基)胍,
N-(2-环丙基羰基苯基氨磺酰基)-N’-(4,6-二甲氧基嘧啶-2-基)脲等。
这些化合物是本身已知的,见述于日本专利公告昭59-481号;日本专利公开昭57-112379号,昭57-56452号,昭59-122488号,平1-38091号,平1-70475号等。除莠吡唑:
4-(2,4-二氯苯甲酰基)-1,3-二甲基吡唑-5-基-对甲苯磺酸酯,
2-[4-(2,4-二氯苯甲酰基)-1,3-二甲基吡唑-5-基]乙酰苯,
2-[4-(2,4-二氯-间甲苯酰基)-1,3-二甲基吡唑-5-基氧基]-4-甲基乙酰苯等。除莠N-丙酰苯胺:
2-(β-萘氧基)-N-丙酰苯胺,
(RS)-2-(2,4-二氯间甲苯氧基)-N-丙酰苯胺等。除莠三嗪:
2,4-双(乙氨基)-6-(甲氨基)-1,3,5-三嗪,
2-乙氨基-4-(1,2-二甲基丙氨基)-6-甲硫基-1,3,5-三嗪等。除莠氨基甲酸酯:
二乙基硫代氨基甲酸S-对氯苄酯,
哌啶-1-硫代羧酸S-1-甲基-1-苯基乙酯,
1,2-二甲基丙基(乙基)硫代氨基甲酸S-苄酯等。除莠二苯醚:
2,4,6-三氯苯基-4’-硝基苯基醚,
2,4-二氯苯基-3’-甲氧基-4’-硝基苯基醚等。除莠嘧啶:2-[(4,6-二甲氧基-2-嘧啶基)氧基]-6-[1-(甲氧基亚氨基)乙基]苯甲酸甲酯等。除莠酰胺:
(RS)-2-溴-N-(α,α-二甲基苄基)-3,3-二甲基丁酰胺等。
以上除莠化合物例如在由英国作物保护委员会出版的PesticideManual,1991中有述。
此外,上述除莠嘧啶还见述于BCPC Weeds,1993,Brighton,Nov.22-25th,1993,第1卷,Ref.2-b。
在上述的除莠组合物中,各有效成分的混合重量比可在比较宽的范围内变动。但一般来讲,可适当地在下列范围内调整:即每重量份式(Ⅰ)化合物,0.01-2重量份、优选0.05-1重量份除莠磺酰胺,2.5-35重量份、优选3-15重量份除莠吡唑,0.6-50重量份、优选2.0-28重量份除莠N-丙酰苯胺,0.06-10重量份、优选0.15-6重量份除莠三嗪,3-15重量份、优选5-10重量份除莠氨基甲酸酯,5-35重量份、优选7-15重量份除莠二苯醚,0.01-2重量份、优选0.1-1重量份除莠嘧啶,和3.5-25重量份、优选4.0-10重量份除莠酰胺。
上述的除莠组合物对多种杂草显示出强除莠作用,因此这些组合物可用作除莠组合物,特别是它们作为水田的选择性除莠剂显示出极佳的效果。
按照本发明的除莠化合物和上述的除莠组合物可用于杀灭例如下列种的水田杂草:下列属的双子叶植物杂草:
蓼属,蔊菜属,节节菜属,母草属,鬼针草属,虻眼属,醴肠属,沟繁缕属,水八角属,Vandellia,丁香蓼属,水芹属,毛茛属和泽番椒属;下列属的单子叶植物杂草:稗属,黍属,早熟禾属,莎草属,雨久花属,飘拂草属,慈姑属,荸荠属,藨草属,泽泻属,安尼来墨草属,水筛属,谷精草属和眼子菜属。
更具体地讲,它们可用于杀灭例如下列水田杂草:学名(植物名)双子叶植物杂草:Rotala indica Koehne(节节菜)Lindemia Procumbens Philcox(陌上菜)Ludwigia prostrata Roxburgh(丁香蓼)Potamogeton distinctus A.Benn(眼子菜)Elatine triandra Schk(三蕊沟繁缕)Oenanthe javanica(Blume)DC.(水芹)单子叶植物杂草:Echinochloa oryzicola Vasing(稗)Monochoria vaginalis Presl(鸭舌草)Eleocharis acicular is L.(牛毛毡)Eleocharis Kuroguwai Ohwi(菱角)Cyperus difformis L.(异型莎草)Cyperus serotinus Rottboel(water nutgrass)Sagittaria pygmaea Miq(矮慈姑)Alisma canaliculatum A.Br.et Bouche(窄叶泽泻)Scirpus juncoides Roxburgh(萤蔺)。
然而本发明的除莠化合物和上述的除莠组合物的应用决不受这些杂草的限制,而同样也可以周于其它的水田杂草。
本发明的除莠剂和上述的除莠组合物可以常规制剂的形式来使用,例如溶液剂、乳剂、可湿性粉末剂、混悬剂、粉剂、可溶性粉剂、颗粒剂、片剂、浓缩混悬剂-乳剂、在聚合物中的微小胶囊,浸有活性化合物的天然的和合成的材料等。
这些制剂可按本身已知的方法来制备。可例如通过将该活性化合物与增量剂即液体溶剂和/或固体载体混合来制备,可任选地使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
适宜的液体溶剂主要有芳烃类例如二甲苯、甲苯或烷基萘;氯化芳烃和氯化脂肪烃类,例如氯苯、氯化乙烯或二氯甲烷;脂肪烃类,例如环己烷或石蜡类,例如石油馏分,矿物油和植物油;醇类,例如丁醇或乙二醇及其醚和酯;酮类,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲亚砜;以及水。在用水作增量剂的情况下,若有必要,可将有机溶剂用作辅助溶剂。
适宜的固体载体有例如铵盐和磨碎的天然的矿物例如高岭土、粘土、滑石、白垩、石英、绿坡镂石、蒙脱石或硅藻土,和磨碎的人造矿物例如高分散硅酸、氧化铝和硅酸盐。用于颗粒剂的适宜的固体载体有例如粉碎并分级的岩石,例如方解石、大理石、浮石、海泡石和白云石以及合成的有机和无机粉颗粒以及有机物质例如木屑、椰子壳、玉米穗轴和烟草茎的颗粒。
适宜的乳化剂和/或发泡剂有例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯和聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物。
适宜的分散剂有例如木素亚硫酸盐废液和甲基纤维素等。
粘合剂亦可以任选地用在制剂例如粉剂、颗粒剂、浸有活性化合物的天然的和合成的材料或乳剂中,有用的粘合剂可举出以下实例:羧甲基纤维素和天然的和合成的聚合物,例如阿拉伯胶,聚乙烯醇,聚乙酸乙烯酯以及天然产物例如脑磷脂和卵磷脂和合成的磷脂。此外,矿物油和植物油可被掺入作为添加剂。
可以使用着色剂例如无机颜料,如氧化铁、二氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,以及微量营养物如金属盐,例如铁、镁、硼、铜、钼、钴和锌的盐。
在所述制剂中活性化合物的含量一般在0.1-95%(重量)之间,0.5-90%(重量)为佳。
按照本发明的除莠化合物和上述的除莠组合物中的活性化合物可直接或以所述制剂的形式用于杀灭不合乎需要的杂草。这些制剂可以事先以最终制剂的形式制得,或者通过使用前进行桶混合来制备。此外,按照本发明的除莠剂和上述的除莠组合物还可以含有其它已知的活性化合物,例如通常可用于水田的那些活性化合物如杀真菌剂、杀虫剂、植物生长调节剂、植物营养剂、土壤改良剂、植物毒性减缓剂和其它除莠剂。在优选的实施方案中,在上述的除莠组合物中,每1重量份上述除莠化合物例如除莠磺酰胺可加入1-200重量份、最好是2-100重量份例如1-(α,α-二甲基苄基)-3-对甲苯基脲作为植物毒性减缓剂。
该活性化合物可直接使用,可以其制剂的形式或以由这样一种制剂通过进一步稀释制得的使用形式例如现成的溶液、乳液、混悬液、粉剂、可湿性粉剂和颗粒剂形式使用。它们可按常规方法例如液体散布、喷雾、雾化、撒粉或散播来使用。
按照本发明的除莠剂和上述的除莠组合物可在出苗前和出苗后施用。
在本发明的除莠剂的情况下,活性化合物的施用量可根据所需作用的性质在宽范围内变动,但一般来讲,该量可例如为每公顷大约0.01-10kg本发明活性化合物,最好为每公顷大约0.1-2kg本发明活性化合物。
此外,在上述的除莠组合物的情况下,该组合物的施用量可在宽范围内变动。就有效成分的总量而言,施用量通常在每公顷0.1-5kg范围内,最好是在0.2-3kg之间。
下面用实施例说明本发明的化合物及其作为除莠剂的用途,但本发明决不受其限制。制备实施例:
实施例1
将1-(2-甲基环己基)-5(4H)-四唑啉酮(2g)、4-二甲氨基吡啶(1.6g)和二乙基氨基甲酰氯(1.7g)悬浮于甲苯(70ml)中,并将混合物于50-55℃搅拌5-6小时。冷却后,将有机层依次周水、1%盐酸、水、碳酸氢钠饱和水溶液和水洗涤。将有机层用无水硫酸钠干燥后,减压蒸除溶剂,并将残余物用柱层析纯化(洗脱剂:氯仿),得到所需的1-(2-甲基环己基)-4-(二乙基氨基甲酰基)-5(4H)-四唑啉酮(2.6g),ND201.4992。
表Ⅰ中示出了用方法(a)可制得的其它四唑啉酮衍生物以及上述实施例1的化合物(为第27号化合物):
表1
表1(续)
表1(续)
表1(续)
将2-甲基环己基异氰酸酯(10g)、三甲基甲硅烷基叠氮(12.4g)和催化量的乙醚合三氟化硼混合,并将混合物加热回流40小时。减压蒸出过量的三甲基甲硅烷基叠氮,并将甲醇加至残余物中。然后减压蒸出甲醇,并将残余物用柱层析纯化(洗脱剂:乙醇/氯仿=4/100),得到所需的1-(2-甲基环己基)-5(4H)-四唑啉酮(10.2g)。m.p.109-113℃。
将4-甲基环己基碳酰氯(10g)、三甲基甲硅烷基叠氮(20.7g)和催化量的乙醚合三氟化硼混合,并将混合物加热回流48小时。减压蒸出过量的三甲基甲硅烷基叠氮,并将甲醇加至残余物中。然后减压蒸出甲醇,而将残余物用柱层析纯化(洗脱剂:乙醇/氯仿=4/100),得到所需的1-(4-甲基环己基)-5(4H)-四唑啉酮(9.5g),m.p.91-95℃。
表2中示出了用任何上述的制备方法(b)-(e)可制得的其它式(Ⅱ)化合物以及上述实施例2和3的化合物(分别为第Ⅱ.2号化合物和第Ⅱ.4号化合物)。
表 2
化合物序号 Xn mp.℃/nD 20
Ⅱ.1 1-CH3 1.4926
Ⅱ.2 2-CH3 109-113
Ⅱ.3 3-CH3 1.5081
Ⅱ.4 4-CH3 91-95
Ⅱ.5 2,3-(CH3)2 84-87.5
Ⅱ.6 2,6-(CH3)2 145-146,5
Ⅱ.7 2,2-(CH3)2
Ⅱ.8 4-C2H5
Ⅱ.9 3,5-(CH3)2
Ⅱ.10 3,3,5,5-(CH3)4
实施例4(生物试验)
对水田杂草的除莠效果试验试验药品的制备载体:丙酮,5重量份乳化剂:苄氧基聚乙二醇醚,1重量份
通过将1重量份的一种活性化合物与上述量的载体和乳化剂混合可以乳剂形式获得一种活性物质的制剂。将规定量的该制剂周水稀释,制得试验药品。试验方法
在温室中,将1株3蘖2.5叶发育阶段(15cm高)的水稻(栽培品种:Nipponbare)秧苗移植在填装有水田土壤的1/2000公亩的盆(25×25×9cm)中的两处。然后将稗、异型莎草、鸭舌草、宽叶杂草(陌上菜、节节菜、三蕊沟繁缕、多花水苋、虻眼)和萤蔺的种子播到土壤中,并加水至水深为高出土壤表面大约2-3cm。在水稻移植5天后,将按照上述制备方法制得的试验药品各施用于水表面上。
处理3周后检查除莠效果和对作物植物的植物毒性的程度,在处理后3周这段时间中水深度保持在3cm。
在全部死亡的情况下除莠效果被评定为100%,而在未观察到除莠效果的情况下,除莠效果被评定为0%。结果见下表3。
表 3
制剂实施例1
化合物序号(见表1) | 浓度(kg/ha) | 除莠效果 | 植物毒性 | ||||
稗 | 异型莎草 | 萤蔺 | 鸭舌草 | 宽叶杂草 | 水稻 | ||
3132388183对比:C-1C-2 | 0.250.250.250.250.250.250.25 | 10010010010010080100 | 10010010010010090100 | 901009090907090 | 10010010010010090100 | 90909090908090 | 000001030 |
将水加至1.25重量份化合物31、30重量份膨润土、66.75重量份滑石粉和2重量份木素磺酸盐的混合物中,并将混合物充分捏合,接着进行制粒,干燥,得到颗粒剂。本发明的效果:
如实施例中所示,本发明的新的除莠四唑啉酮不仅可容易地用常规制备方法来合成,而且作为除莠剂,显示出极佳的活性,特别是对水田杂草具有极佳的活性。
此外,本发明的四唑啉酮在与某些其它的除莠化合物混合后能形成效果更佳的除莠组合物。
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JP7088619A JPH08259548A (ja) | 1995-03-23 | 1995-03-23 | テトラゾリノン類及び除草剤 |
JP88619/1995 | 1995-03-23 |
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KR (1) | KR100435192B1 (zh) |
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DE19504059A1 (de) * | 1995-02-08 | 1996-08-14 | Bayer Ag | Verfahren zur Herstellung von substituierten N-Carbamoyl-tetrazolinonen |
US6017853A (en) | 1996-07-16 | 2000-01-25 | Nihon Bayer Agrochem K.K. | Herbicidal 1-substituted methyl-tetrazolinones |
US6277790B1 (en) | 1997-08-06 | 2001-08-21 | Basf Aktiengesellschaft | Substituted herbicide tetrazolinonecarboxylic acid amides |
JP2000327668A (ja) | 1999-05-21 | 2000-11-28 | Nippon Bayer Agrochem Co Ltd | テトラゾリノン誘導体 |
CA2798330A1 (en) | 2010-05-05 | 2011-11-10 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
JP6142752B2 (ja) | 2012-09-28 | 2017-06-07 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
JP6142753B2 (ja) | 2012-09-28 | 2017-06-07 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
JP6337896B2 (ja) * | 2013-05-29 | 2018-06-06 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
WO2015088038A1 (ja) * | 2013-12-12 | 2015-06-18 | 住友化学株式会社 | 芳香族化合物及びその用途 |
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US5019152A (en) * | 1983-12-09 | 1991-05-28 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and their use as herbicides |
US5120346A (en) * | 1983-12-09 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones for plant growth inhibition |
US5003075A (en) * | 1983-12-09 | 1991-03-26 | Uniroyal Chemical Company, Inc. | Preparation of substituted tetrazolinones |
US4826529A (en) * | 1983-12-09 | 1989-05-02 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and herbicidal compositions thereof |
US4618365A (en) * | 1983-12-09 | 1986-10-21 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and their use as herbicides |
US4830661A (en) * | 1983-12-09 | 1989-05-16 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones and herbicidal compositions thereof |
JP3102952B2 (ja) * | 1992-05-28 | 2000-10-23 | 日本バイエルアグロケム株式会社 | 除草性1−(3−ハロ−4−トリフルオロメチルフェニル)テトラゾリノン誘導体 |
JP3102953B2 (ja) * | 1992-05-28 | 2000-10-23 | 日本バイエルアグロケム株式会社 | 1−(3,4−ジ置換フェニル)テトラゾリノン誘導体、その製造法および除草剤としての用途 |
JP3102954B2 (ja) * | 1992-06-03 | 2000-10-23 | 日本バイエルアグロケム株式会社 | 除草性1−(3−ハロ−4−置換フェニル)テトラゾリノン誘導体 |
JP3505195B2 (ja) * | 1992-07-09 | 2004-03-08 | バイエルクロップサイエンス株式会社 | テトラゾリノン類の水田用除草剤としての利用 |
JP2822143B2 (ja) * | 1993-02-25 | 1998-11-11 | 日本バイエルアグロケム株式会社 | テトラゾリノン類の水田用除草剤としての利用 |
JP3670314B2 (ja) * | 1993-08-05 | 2005-07-13 | バイエルクロップサイエンス株式会社 | 1−置換−5(4h)−テトラゾリノン類の製造方法 |
JP3390499B2 (ja) * | 1993-09-30 | 2003-03-24 | バイエルクロップサイエンス株式会社 | テトラゾリノン類の製造方法 |
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TW304948B (zh) | 1997-05-11 |
CN1138574A (zh) | 1996-12-25 |
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