CN1061651C - 除莠1-链烯基四唑啉酮 - Google Patents
除莠1-链烯基四唑啉酮 Download PDFInfo
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- CN1061651C CN1061651C CN96103127A CN96103127A CN1061651C CN 1061651 C CN1061651 C CN 1061651C CN 96103127 A CN96103127 A CN 96103127A CN 96103127 A CN96103127 A CN 96103127A CN 1061651 C CN1061651 C CN 1061651C
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- alkyl
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- 241000196324 Embryophyta Species 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 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 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- JTTIAXADVUVBBB-UHFFFAOYSA-N FC1=C(C(=C(C(=O)O)C=C1)C)C(=O)O Chemical compound FC1=C(C(=C(C(=O)O)C=C1)C)C(=O)O JTTIAXADVUVBBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 239000004009 herbicide Substances 0.000 abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 27
- -1 C 1-4Alkyl Inorganic materials 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006837 decompression Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 230000001419 dependent effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 241000219318 Amaranthus Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000002245 particle Substances 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
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- ONKIPJDBUYZQMP-UHFFFAOYSA-N n-cyclohexyl-n-ethylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1CCCCC1 ONKIPJDBUYZQMP-UHFFFAOYSA-N 0.000 description 1
- CDGCUPPKLDOYGV-UHFFFAOYSA-N n-ethyl-n-phenylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1 CDGCUPPKLDOYGV-UHFFFAOYSA-N 0.000 description 1
- CPGWSLFYXMRNDV-UHFFFAOYSA-N n-methyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1 CPGWSLFYXMRNDV-UHFFFAOYSA-N 0.000 description 1
- HIENBQZSBONJNN-UHFFFAOYSA-N n-phenyl-n-propylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)C1=CC=CC=C1 HIENBQZSBONJNN-UHFFFAOYSA-N 0.000 description 1
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- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
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- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及式(Ⅰ)1-链烯基四唑啉酮,该化合物表现出强除莠活性,可用作除莠剂。所述式(Ⅰ)如下,式中R2和R3相互独立地代表C1-6烷基,可任选地被甲基取代的C3-7环烷基,C2-4链烯基,C2-5炔基,可任选地被取代的苯基或芳烷基,或者R2和R3可同与之键合的N原子一起形成可任选地被取代的杂环;R1代表下式基团:
Description
本发明涉及新的1-链烯基四唑啉酮、其制备方法以及其作为除莠剂的用途以及用于其的新的中间体。
人们已知某种四唑啉酮具有除莠活性(参见:EP-A-146279)。
其它的参考文献包括美国专利4618365号(=EP 146279),4826529号,4830661号,4956469号,5003075号,5019152号,5120346号,5342954号,5344814号,5347009号,5347010号和5362704号。
式中
A代表氢,C1-4烷基,卤素或C1-2卤代烷基,
B和D相互独立地代表氢,C1-4烷基或卤素,或
B和D可同与之键合的C原子一起形成C5-6亚环烷基,
T代表氢或C1-4烷基,
n代表0,1,2或3,
式中
J和L相互独立地代表氢、C1-4烷基或卤素;和
G代表氢或C1-4烷基,或
B和G可同与之键合的C原子一起形成C5-6环烯-1-基,
R2和R3相互独立地代表C1-6烷基,可任选地被甲基取代的C3-7环烷基,C2-4链烯基,C2-5炔基,可任选地被取代的苯基或可任选地被取代的芳烷基,或者
R2和R3可任选地同与之键合的N原子一起形成可任选地被取代的杂环。
按照本发明的式(Ⅰ)化合物可例如用方法a)来制备,在方法a)中,使式(Ⅱ)化合物在惰性溶剂存在下并且,若合适,在酸结合剂存在下与式(Ⅲ)化合物反应;所述式(Ⅱ)和(Ⅲ)如下:式中R1的定义同上,式中R2和R3的定义同上,和M代表离去基团,例如氯,溴等。
按照本发明的式(Ⅰ)化合物具有强除莠活性,特别是,与上述的EP-A-146279中所述的与式(Ⅰ)化合物类似的已知化合物相比,按照本发明的式(Ⅰ)化合物显示强得多的除莠活性作用,并且表现出作物植物的良好的耐受性。因此,按照本发明的化合物特别可用作选择性除莠剂。
在本说明书中,术语“卤素”包括氟、氯、溴和碘,优选氟、氯或溴。
“烷基”、“链烯基”、“炔基”、“环烷基”、“环烷烃”和“环烯烃”分别为具有一定的碳数并适当地可具有支链的饱和的、不饱和的或环状的脂族烃基或脂族烃环。
“芳烷基”包括苄基、1-苯基乙基和2-苯基乙基,优选苄基。
在“可任选地被取代的苯基”和“可任选地被取代的芳烷基”中的取代基包括例如卤素,C1-4烷基,C1-2烷氧基,C1-2卤代烷基,C1-2卤代烷氧基,C1-2卤代烷硫基,氰基,硝基,乙酰基等。该苯基和芳烷基可被至少一个,优选1-2个这样的取代基取代。
在“与N原子一起形成的可任选地被取代的环”中,所述环为含至少一个、优选只含一个氮原子的5至6元单环或苯并稠合的多环杂环。可由式(Ⅰ)中基团形成的环状基团的实例包括吡咯烷-1-基,哌啶-1-基,二氢吲哚-1-基,吲哚-1-基,1,2-二氢喹啉-1-基,1,2,3,4-四氢喹啉-1-基等,并且这样的环可被任选地取代。其可能的取代基包括C1-4烷基例如甲基、乙基,和卤素(例如氟和氯),优选甲基或氟。
或基团:
式中
A1代表氢,甲基,氯,溴或三氟甲基,
B1和D1相互独立地代表氢,甲基,乙基,氯或溴,或者
B1和D1可同与之键合的C原子一起形成C5-6亚环烷基,
T1代表氢或甲基,
m代表0,1或2,
E1代表基团
式中
J1和L1相互独立地代表氢、甲基、乙基、氟或氯,和
G1代表氢或甲基,或者
E1和G1可同与之键合的C原子一起形成C5-6环烯-1-基,
R2和R3相互独立地代表C1-4烷基,环丙基,可任选地被甲基取代的C5-6环烷基,C2-3链烯基,C3-5炔基,可任选地被取代的苯基(其中取代基是卤素、C1-4烷基、C1-2卤代烷基、C1-2烷氧基、C1-2卤代烷氧基、C1-2卤代烷硫基、硝基、氰基或乙酰基)或可任选地被卤素或C1-4烷基取代的苄基,或者
R2和R3可同与之键合的N原子一起形成吡咯烷-1-基、哌啶-1-基、吲哚-1-基、二氢吲哚-1-基、1,2-二氢喹啉-1-基或1,2,3,4-四氢喹啉-1-基(其中,这些取代基可任选地被甲基或氟取代)。
式中
A2代表氢、甲基、氯或三氟甲基,
B2和D2相互独立地代表氢、甲基、乙基、氯或溴,或者
B2和D2可同与之键合的C原子一起形成C5-6亚环烷基,
T2代表氢,
m代表0,1或2,
E2代表基团:
式中
J2和L2相互独立地代表氢、甲基、乙基或氟,和G2代表氢或甲基,或者
E2和G2可同与之键合的C原子一起形成环戊烯-1-基,
R2和R3相互独立地代表C2-4烷基,环丙基,环戊基,环己基,它们可任选地被甲基取代,烯丙基,炔丙基,1-甲基-3-丙炔基,1,1-二甲基-3-丙炔基,可任选地被取代的苯基(其中取代基是氟、氯、溴、甲基、三氟甲基、三氟甲氧基、二氟甲基、甲氧基、三氟甲硫基、硝基、氰基或乙酰基),或可被氟取代的苄基,或者
R2和R3可同与之键合的N原子一起形成2-甲基二氢吲哚-1-基,2-甲基吲哚-1-基,6-氟-2-甲基-1,2,3,4-四氢喹啉-1-基,2-甲基-1,2,3,4-四氢喹啉-1-基,2-甲基-1,2-二氢喹啉-1-基,2,2-二甲基-1,2-二氢喹啉-1-基或2,2-二甲基-1,2,3,4-四氢喹啉-1-基。
在方法a)中,作为原料的式(Ⅱ)化合物,除R1是乙烯基的情况外,是新化合物,尚未在在前已知的文献中披露。这样的化合物通常可例如用下述方法来制备:方法b):使式(Ⅳ)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:
R1-N=C=O (Ⅳ)式中R1的定义同上;方法c):使上述的式(Ⅳ)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;或者方法d):使式(Ⅴ)化合物与三甲基甲硅烷基叠氮反应,所述式(Ⅴ)如下:式中R1的定义同上
在上述的方法b)和c)中,用作原料的式(Ⅳ)化合物包括在有机化学领域公知的异氰酸酯类,可例如通过由相应的链烯酰氯与叠氮化钠反应获得的链烯羰基叠氮来制备,即按照“Method for SynthesizingOrganic Compounds (Yuki Kagobutsu Goseiho)”,第11卷,133页(由Organic Synthetic Chemistry Association社团编辑,Gihodo于1959年7月15日发行)中所述的方法来制备。
在上述方法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,可例如通过式(Ⅷ)链烯羧酸与例如作为卤化剂的亚硫酰氯反应而容易地制得,即按照“New Experimental Chemistry Course(Shin Jikken Kagaku Koza)”,第14卷,1105-1120页(由Maruzen在1977年12月20日发行)中所述的方法来制备;所述式(Ⅷ)如下:
R1-COOH (Ⅷ)式中R1的定义同上。
上述的式(Ⅷ)化合物还可按照“New Experimental ChemistryCoutse(Shin JikkenKagaku Koza”,第14卷,921-1000页(由Matuzen在1997年12月20日发行)中所述的方法,通过将相应的链烯羧酸酯水解而容易地制得。
上述式(Ⅱ)化合物的典型实例如下:1-乙烯基-5(4H)-四唑啉酮,1-烯丙基-5(4H)四唑啉酮,1-(1-丙烯基)-5(4H)-四唑啉酮,1-(1-甲基乙烯基)-5(4H)-四唑啉酮,1-(3-丁烯基)-5(4H)-四唑啉酮,1-(1-丁烯基)-5(4H)-四唑啉酮,1-(1-甲基-1-丙烯基)-5(4H)-四唑啉酮,1-(2-甲基-1-丙烯基)-5(4H)-四唑啉酮,1-(2-甲基-2-丙烯基)-5(4H)-四唑啉酮,1-(1-戊烯基)-5(4H)-四唑啉酮,1-(2-戊烯基)-5(4H)-四唑啉酮,1-(1-甲基-1-丁烯基)-5(4H)-四唑啉酮,1-(5-己烯基)-5(4H)-四唑啉酮,1-(亚环戊基甲基)-5(4H)-四唑啉酮,1-(亚环己基甲基)-5(4H)-四唑啉酮,(Z)-1-(2-氯乙烯基)-5(4H)-四唑啉酮,(E)-1-(2-氯乙烯基)-5(4H)-四唑啉酮,1-(1-氯乙烯基)-5(4H)-四唑啉酮,1-(1-溴乙烯基)-5(4H)-四唑啉酮,1-(1-三氟甲基乙烯基)-5(4H)-四唑啉酮,1-(1,2,2-三氯乙烯基)-5(4H)-四唑啉酮,1-(2-溴-1-甲基乙烯基)-5(4H)-四唑啉酮,1-(2-氯-1-丙烯基)-5(4H)-四唑啉酮,1-(3,4,4-三氟-3-丁烯基)-5(4H)-四唑啉酮等。
另一方面,与上述的式(Ⅱ)化合物反应的式(Ⅲ)化合物是氨基甲酰氯类,它们是有机化学领域中熟知的,其典型的实例包括下列化合物:N,N-二乙基-氨基甲酰氯;N-环己基-N-乙基氨基甲酰氯,N,N-二正丙基氨基甲酰氯,N-环丙基-N-正丙基氨基甲酰氯,N-环戊基-N-正丙基氨基甲酰氯,N-二烯丙基氨基甲酰氯,N-二炔丙基氨基甲酰氯,N-异丙基-N-苯基氨基甲酰氯,N-2-氯苯基-N-异丙基氨基甲酰氯,N-3-氯苯基-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-对甲苯基氨基甲酰氯,N-苄基-N-异丙基氨基甲酰氯,N-(2,3-环氧丙烷-1-基)-N-苯基氨基甲酰氯,N-2-乙酰基苯基-N-异丙基氨基甲酰氯,N-异丙基-n-2-(1-甲氧基亚氨基乙基)苯基氨基甲酰氯,1-二氢吲哚基碳酰氯,2,2-二甲基-1,2,3,4-四氢喹啉-1-基碳酰氯,2-甲基-1,2,3,4-四氢喹啉-1-基碳酰氯,N-1,1-二甲基炔丙基-N-苯基氨基甲酰氯,N-烯丙基-N-苯基氨基甲酰氯,N-甲基-N-苯基氨基甲酰氯,N-乙基-N-苯基氨基甲酰氯,N-正丙基-N-苯基氨基甲酰氯,N-环己基-N-异丙基氨基甲酰氯,N-异丙基-N-4-硝基苯基氨基甲酰氯,N-异丙基-N-4-氰基苯基氨基甲酰氯,2-甲基-1,2-二氢喹啉-1-基氨基甲酰氯,2,2-二甲基-1,2-二氢喹啉-1-基氨基甲酰氯等。
方法a)中的反应通常可在对该反应惰性的有机溶剂中进行,可用于该反应的惰性有机溶剂的实例包括脂族、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);等。
方法a)可在碱存在下进行。可用的碱的优选实例包括4-二甲氨基吡啶(DMAP)。
在用DMAP作碱的情况下,方法a)中的反应通常可在常压下于大约-10-200℃、优选大约25-140℃的温度进行,但亦可任选地在加压或减压下进行。
此外,方法a)中的反应还可用除DMAP外的碱来进行。这样的碱的实例有无机盐(例如碳酸钠,碳酸钾,氢氧化钠,氢氧化钾等);链烷醇化物(例如甲醇钠,乙醇钠,叔丁醇钾等);氢氧化钠;氢氧化钾;氢氧化锂;有机碱(例如三乙胺,1,1,4,4-四甲基乙二胺,N,N-二甲基苯胺,吡啶等);等。
在用这样的碱进行该反应的情况下,式(Ⅰ)化合物可通过使用DMAP作催化剂而被选择性地获得。
在这种情况下的反应温度一般可设置在大约0-150℃、优选大约25-100℃的范围内。此外,该反应应最好在常压下进行,但亦可以任选地在加压或减压下进行。
因此,式(Ⅰ)化合物可通过例如使大约1-1.5mol式(Ⅲ)化合物在大约1-1.5mol DMAP作为碱存在下在如上所述的惰性溶剂中与1mol式(Ⅱ)化合物反应来获得。或者,式(Ⅰ)化合物还可以通过使大约1-1.5mol式(Ⅲ)化合物在下列条件下与1mol式(Ⅱ)化合物反应来制备:在大约0.01-0.3mol DMAP作为催化剂和大约1-1.5mol碱例如碳酸钾存在下,在如上所述的惰性溶剂中。
如此制得的式(Ⅰ)化合物可借助例如结晶法、层极法等分离纯化。
另一方面,上述的方法b)可通过使用乙醚合三氟化硼作催化剂来实施。反应温度一般可设置为大约0-200℃,优选大约50-150℃。此外,反应最好应在常压下进行,但亦可以任选地在加压或减压下进行。
方法b)可通过使大约1-2mol三甲基甲硅烷基叠氮在大约0.005-0.01mol乙醚合三氟化硼作催化剂存在下与1mol式(Ⅳ)化合物反应来实施。
此外,方法c)中的反应通常可在极性溶剂中进行,可用的极性溶剂的实例有酰胺,例如二甲基甲酰胺,二甲基乙酰胺等;和亚砜,例如二甲亚砜,四氢噻吩砜等。反应温度通常可设置为大约0-200℃,优选大约20-150℃。此外,该反应最好应在常压下进行,但亦可任选地在加压或减压下进行。
方法c)通常可通过使大约1-1.5mol叠氮化钠在大约0.05-1mol氯化铵作为催化剂存在下在极性溶剂例如二甲基甲酰胺中与1mol式(Ⅳ)化合物反应来实施。
在方法d)中的反应一般可在常压下在大约0-200℃、最好是大约25-130℃的温度进行,但亦可任选地在加压或减压下进行。
方法d)可通过使大约2-4mol三甲基甲硅烷基叠氮与1mol式(V)化合物反应来实施。
按照本发明的式(Ⅰ)活性化合物正如下面的试验实施例中所示的那样具有极佳的除莠活性,因而可将它们用作除莠剂用于防治杂草。术语“杂草”是指生长在不合需要的场所的所有植物。
按照本发明的化合物根据所用的浓度,能用作非选择性或选择性除莠剂。按照本发明的活性化合物例如对于下列杂草和栽培植物可用作选择性除莠剂。下列属的双子叶植物杂草:欧芥属,独行菜属,拉拉藤属,繁缕属,黎属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,番薯属,蓼属,豚草属,蓟属,苦苣菜属,茄属,蔊莱属,野芝麻属,婆婆纳属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,牛膝菊属,节节菜属,母草属等。下列属的双子叶栽培物:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,野豌豆属,烟草属,番茄属,落花生属,芸苔属,莴苣属,香瓜属,南瓜属等。下列属的单子叶植物杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,狐茅属,穇属,毒麦属,雀麦属,燕麦属,莎草属,高粮属,冰草属,雨久花属,飘拂草属,慈姑属,荸荠属,藨草属,雀稗属,鸭嘴草属,剪股颖属,看麦娘属,狗牙根属等。下列属的单子叶植物栽培物:稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,高粮属,黍属,甘蔗属,凤梨属,天门冬属,葱属等。
然而按照本发明的式(Ⅰ)活性化合物的应用决不受以上属的限制,而同样可扩展到其它植物。此外,本发明的活性化合物根据浓度适宜于完全杀灭例如工业场所、铁轨和植树或未植树的小路和广场上的杂草。
同样,本发明活性化合物可用于杀灭多年生栽培植物例如人造林、观赏树木种植园、果园、葡萄园、柑桔园林、坚果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕种植园、可可种植园、浆果种植园和啤酒花地里的杂草,并可用于选择性杀灭一年生栽培植物中的杂草。
按照本发明的式(Ⅰ)活性化合物可被转化成常规制剂,例如溶液剂,乳液剂、可湿性粉剂、混悬剂、粉剂、可溶性粉剂、颗粒剂、浓缩混悬剂-乳剂、在聚合物中的极细小胶囊、浸有活性化合物的天然的和合成的材料等。
这些制剂可按任何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、甲苯或烷基萘等;氯化芳烃或氯化脂肪烃类,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,可将有机溶剂用作辅助溶剂。
适宜的固体载体有铵盐和粉碎的天然矿石(例如高岭土、粘土、滑石、白垩、石英、绿坡镂石、蒙脱石或硅藻土,和粉碎的人造矿石,例如高分散硅酸、氧化铝和硅酸盐。适宜的用于颗粒剂的固体载体可以粉碎并分级的天然岩石为例,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,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。
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人造的材料或乳剂中,这样的粘合剂可举出以下实例:羧甲基纤维素,天然的和合成的聚合物例如阿拉伯胶,聚乙烯醇和聚乙酸乙烯酯以及天然的磷脂例如脑磷脂和卵磷脂,和合成的磷脂。矿物油和植物油亦可被用作另外的添加剂。
还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、钴、钼和锌的盐。
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。
本发明的活性化合物可直接或以所述制剂的形式用于防治杂草并可与任何已知的除莠剂混合。这些混合物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。
可将按照本发明的式(Ⅰ)活性化合物与化学损伤减缓剂混合。通过此种混合,可大大扩展选择性除莠剂的可施用性。
化学损伤减缓剂可举1-(α,α-二甲基苄基)-3-对甲苯基脲为例。
按照本发明的式(Ⅰ)活性化合物可被直接施用,或者以上述的制剂形式施用,施用方法为常规方法,例如液体散布、喷雾、雾化、撒粉或散播颗粒。
按照本发明的式(Ⅰ)活性化合物可在出苗前或出苗后的任何阶段施用,亦可在播种前将其掺至土壤中。
对活性化合物的施用量无严格限制,可根据所需效果、目标植物(一种或多种)的种类、施用地点、施用时间等在宽范围内变动。但作为试验性估量,例如施用量可例如为每公顷大约0.001-10kg活性化合物,最好为每公顷大约0.01-5kg活性化合物。
将(Z)-1-(2-氯乙烯基)-5(4H)-四唑啉酮(0.6g)、4-二甲氨基吡啶(0.7g)和二乙基氨基甲酰氯(0.7g)悬浮于甲苯(50ml)中并于50-55℃搅拌5小时。冷却后,将有机层依次用水、1N盐酸、水、饱和碳酸氢钠水溶液和水洗涤。将有机层用无水硫酸钠干燥,减压蒸除溶剂并将残余物用柱层析纯化(洗脱剂:氯仿100%),得到所需的(Z)-1-(2-氯乙烯基)-4-(N,N-二乙基氨基甲酰基)-5(4H)-四唑啉酮(0.85g);n20 D1.5094。
表Ⅰ中列出了用上述反应步骤可获得的其它式(Ⅰ)化合物以及实施例1所获得的化合物。
表1
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
将(Z)-2-氯乙烯基碳酰氯(10g)、三甲基甲硅烷基叠氮(27.6g)和催化量的乙醚合三氟化硼混合,并加热回流48小时。将过量的三甲基甲硅烷基叠氮减压蒸出,并向残余物中加入甲醇。然后将甲醇减压蒸出,将残余物用柱层析纯化(洗脱剂:乙醇/氯仿=6/100),得到(Z)-1-(2-氯乙烯基)-5(4H)-四唑啉酮(6.2g)。m.p.97-99℃。合成实施例3(中间体)
将1-丙烯基异氰酸酯(10g)、三甲基甲硅烷基叠氮(20.8g)和催化量的乙醚合三氟化硼混合并加热回流40小时。减压蒸出过量的三甲基甲硅烷基叠氮,并将甲醇加至该残余物中。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1-(1-丙烯基)-5(4H)-四唑啉酮(8.5g)m.p.110.5-111.5℃。
表2中示出了用与合成实施例2或3相同的方法获得的化合物以及合成实施例2和3中所获得的化合物。
表2(续)试验实施例1
对已耕地杂草的出苗前土壤处理试验制备方法载体:丙酮,5重量份乳化剂:苄氧基聚乙二醇醚,1重量份
将1重量份活性化合物与上述量的载体和乳化剂混合,得到乳剂。将规定量的该乳剂用水稀释,制得试验药品。试验方法
在温室中,将稗属和苋属的种子各播种在装有已耕地土壤的120cm2的花盆中的表层,用土覆盖,并将规定量的上述试验药品各均匀地撒布在试验花盆中的土壤的表层。施用4周后检查除莠效果。在全部死亡的情况下,将除莠效果评定为100%,而将未处理过的区域观察到同等生长的情况的除莠效果评定为0%。结果
通过施用1kg/公顷作为有效成分的第65、68、71、81、96、211、245、248、250、258、263、310和319号化合物100%地消灭掉目标杂草。试验实施例 2
对已耕地杂草出苗后叶面处理的试验试验方法
在温室中,将稗属和苋属的种子各播种在装有已耕地土壤的120cm2花盆中并用土壤覆盖。播种并覆盖土壤10天后(这时杂草平均来看是处于2叶阶段),将按类似于上述试验实施例1的方法制得的各规定量的药品均匀地撒布在试验花盆中的受试植物的叶片部分上,撒布3周后,检查除莠效果的程度。结果
通过施用1kg/公顷作为有效成分的第68、96、250、310和319号化合物,不低于90%的目标杂草被消灭掉。制剂实施例1(颗粒剂)
将25份水加至10份化合物65、30份膨润土(蒙脱石)、58份滑石粉和2份木素磺酸盐的混合物中,充分捏合,接着用挤出式制粒机在10-40筛中制粒,并于40-50℃干燥,获得颗粒剂。制剂实施例2(颗粒剂)
将95份粒度分布为0.2-2mm的粘土矿物颗粒和5份化合物68投入旋转式混合器中,在旋转下喷入液体稀释剂以进行均匀润湿,接着于40-50℃干燥,得到颗粒剂。制剂实施例3(乳剂)
将30份化合物71、55份二甲苯、8份聚氧乙烯烷基苯基醚和7份烷基苯磺酸钙搅拌混合获得乳剂。制剂实施例4(可湿性粉剂)
将15份化合物245、80份White Carbon(水合无定形氧化硅的细粉)和粘土粉末(1∶5)的混合物、2份烷基苯磺酸钠和3份烷基萘磺酸钠和甲醛的缩合物粉碎并混合,制得可湿性粉末。制剂实施例5(可湿性颗粒剂)
可湿性颗粒剂如下制备:将20份化合物310、30份木素磺酸钠、1 5份膨润土和35份煅烧过的硅藻土粉末充分混合,然后加水并将所得到的混合物挤压通过0.3mm筛,随后干燥。本发明的效果
按照本发明的新除莠四唑啉酮衍生物可用如实施例中所示的常规制备方法容易地合成,并能显示出作为除莠剂的有效作用。
Claims (6)
式中
A1代表氢或甲基,
B1和D1相互独立地代表氢,甲基,乙基,氯或溴,或者
B1和D1可同与之键合的C原子一起形成C5-6亚环烷基,
T1代表氢或甲基,
m代表0或1,
E1代表基团:
式中
J1和L1相互独立地代表氢,和
G1代表氢或甲基,
R2和R3相互独立地代表C1-4烷基,环丙基,可任选地被甲基取代的C5-6环烷基,C3-5炔基,可任选地被卤素或C1-4烷基取代的苯基,或者R2和R3可同与之键合的N原子一起形成吲哚-1-基、二氢吲哚-1-基、1,2-二氢喹啉-1-基或1,2,3,4-四氢喹啉-1-基,这些取代基可任选地被甲基或氟取代。
式中
A2代表氢或甲基,
B2和D2相互独立地代表氢、甲基、乙基、氯或溴,或者
B2和D2可同与之键合的C原子一起形成C5-6亚环烷基,
T2代表氢,
m代表0或1,
E2代表基团:
式中
J2和L2相互独立地代表氢,和
G2代表氢或甲基,
R2和R3相互独立地代表C2-4烷基,环丙基,环戊基,环己基,它们可任选地被甲基取代,炔丙基,1-甲基-3-丙炔基,1,1-二甲基-3-丙炔基,可任选地被氟、氯、溴或甲基取代的苯基,或者
R2和R3可同与之键合的N原子一起形成2-甲基二氢吲哚-1-基,2-甲基吲哚-1-基,6-氟-2-甲基-1,2,3,4-四氢喹啉-1-基,2-甲基-1,2,3,4-四氢喹啉-1-基,2-甲基-1,2-二氢喹啉-1-基,2,2-二甲基-1,2-二氢喹啉-1-基或2,2-二甲基-1,2,3,4-四氢喹啉-1-基。
式中
A代表氢或C1-4烷基,
B和D相互独立地代表氢,C1-4烷基或卤素,或
B和D可同与之键合的C原子一起形成C5-6亚环烷基,
T代表氢或C1-4烷基,
n代表0或1,
式中
J和L相互独立地代表氢,和
G代表氢或C1-4烷基,
R2和R3相互独立地代表C1-6烷基,可任选地被甲基取代的C3-7环烷基,C2-5炔基,可任选地被卤素或C1-4烷基取代的苯基,或者
R2和R3可任选地同与之键合的N原子一起形成吲哚-1-基、二氢吲哚-1-基、1,2-二氢喹啉-1-基或四氢喹啉-1-基,它们可任选地被甲基或氟取代,
所述方法的特征在于:
a)将式(Ⅱ)化合物在惰性溶剂存在下并且,若合适,在酸结合剂存在下与式(Ⅲ)化合物反应;所述式(Ⅱ)和(Ⅲ)如下:
式中
R2和R3的定义同上,和
M代表离去基团氯和溴。
5.除莠组合物,其特征在于:它们含有至少一种式(Ⅰ)1-链烯基四唑啉酮。
6.式(Ⅰ)1-链烯基四唑啉酮除杂草的用途。
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JP7085937A JPH08259547A (ja) | 1995-03-20 | 1995-03-20 | 除草性1−アルケニルテトラゾリノン類 |
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CN00117911A Pending CN1309123A (zh) | 1995-03-20 | 2000-05-23 | 制备除莠1-链烯基四唑啉酮所用的中间体 |
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EP (1) | EP0733624A1 (zh) |
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KR (1) | KR960034186A (zh) |
CN (2) | CN1061651C (zh) |
AR (1) | AR001113A1 (zh) |
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US6017853A (en) | 1996-07-16 | 2000-01-25 | Nihon Bayer Agrochem K.K. | Herbicidal 1-substituted methyl-tetrazolinones |
EP0820994A1 (en) * | 1996-07-18 | 1998-01-28 | Nihon Bayer Agrochem K.K. | Tetrazolinones as herbicides and intermediates |
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 |
WO2016022434A1 (en) | 2014-08-04 | 2016-02-11 | Rigel Pharmaceuticals, Inc. | Fumarate analogs and uses thereof in the treatment of an autoimmune disease or an inflammatory disease |
CN113666859B (zh) * | 2021-08-24 | 2023-04-25 | 广州大学 | 一种氮杂环取代的三氟甲基烯烃及其迈克尔加成产物的制备方法 |
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EP0146279A1 (en) * | 1983-12-09 | 1985-06-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones useful as herbicides |
EP0202929A2 (en) * | 1985-05-23 | 1986-11-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones |
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US5019152A (en) * | 1983-12-09 | 1991-05-28 | 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 |
US5003075A (en) * | 1983-12-09 | 1991-03-26 | Uniroyal Chemical Company, Inc. | Preparation of substituted tetrazolinones |
US5120346A (en) * | 1983-12-09 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Substituted tetrazolinones for plant growth inhibition |
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 |
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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- 1996-03-07 EP EP96103537A patent/EP0733624A1/en not_active Ceased
- 1996-03-14 AU AU48134/96A patent/AU4813496A/en not_active Abandoned
- 1996-03-15 KR KR1019960007059A patent/KR960034186A/ko not_active Application Discontinuation
- 1996-03-15 CA CA002171908A patent/CA2171908A1/en not_active Abandoned
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- 1996-03-19 BR BR9601052A patent/BR9601052A/pt not_active Application Discontinuation
- 1996-03-20 CN CN96103127A patent/CN1061651C/zh not_active Expired - Fee Related
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EP0146279A1 (en) * | 1983-12-09 | 1985-06-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones useful as herbicides |
EP0202929A2 (en) * | 1985-05-23 | 1986-11-26 | UNIROYAL CHEMICAL COMPANY, Inc. | Substituted tetrazolinones |
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KR960034186A (ko) | 1996-10-22 |
EP0733624A1 (en) | 1996-09-25 |
CN1134934A (zh) | 1996-11-06 |
AR001113A1 (es) | 1997-09-24 |
ZA962206B (en) | 1996-09-26 |
US5668087C1 (en) | 2002-07-09 |
CN1309123A (zh) | 2001-08-22 |
BR9601052A (pt) | 1998-01-06 |
US5668087A (en) | 1997-09-16 |
AU4813496A (en) | 1996-10-03 |
CA2171908A1 (en) | 1996-09-21 |
JPH08259547A (ja) | 1996-10-08 |
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