CN1141306C - 新型苯甲酰基吡唑化合物、制备中间体和除草剂 - Google Patents
新型苯甲酰基吡唑化合物、制备中间体和除草剂 Download PDFInfo
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- CN1141306C CN1141306C CNB988107872A CN98810787A CN1141306C CN 1141306 C CN1141306 C CN 1141306C CN B988107872 A CNB988107872 A CN B988107872A CN 98810787 A CN98810787 A CN 98810787A CN 1141306 C CN1141306 C CN 1141306C
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- Prior art keywords
- compound
- methyl
- phenmethyl
- phenacyl
- alkyl
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- 239000004009 herbicide Substances 0.000 title abstract description 12
- 239000000543 intermediate Substances 0.000 title abstract description 6
- UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 10
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- -1 pyrazole compound Chemical class 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
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- 238000006243 chemical reaction Methods 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 18
- 239000003513 alkali Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 12
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 235000015320 potassium carbonate Nutrition 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 238000003810 ethyl acetate extraction Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000000887 hydrating effect Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- NQSNZVWJOPFLDF-UHFFFAOYSA-N 3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl chloride Chemical compound CC1=C(C(Cl)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 NQSNZVWJOPFLDF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
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- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 3
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- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- UGPWBKRNDYFLAG-UHFFFAOYSA-N CC1C=CC(=C(C1(C)C(=O)O)CBr)S(=O)(=O)C Chemical compound CC1C=CC(=C(C1(C)C(=O)O)CBr)S(=O)(=O)C UGPWBKRNDYFLAG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000005512 Ethofumesate Substances 0.000 description 3
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- 235000010234 sodium benzoate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
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- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- Dentistry (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
通式[I]所示的化合物或其盐，其制备中间体，以及含有该化合物的除草剂。[式中，R1表示C1-6烷基，R2表示C1-6烷硫基或C1-6烷基磺酰基，R3和R4分别表示氢原子或C1-6烷基，R5表示氢原子或苯甲基等，R7、R8、R9和R10分别表示氢原子或C1-6烷基。]
Description
技术领域
本发明涉及吡唑环的4位被苯甲酰基取代的新型吡唑化合物和除草剂。
背景技术
在农作物的栽培中，有多种除草剂开始逐步用于必须花费很多劳力的杂草防除中。但是，由于会对作物产生药害，或残留在环境中，或造成污染，因此期望开发一种以更低药量即可发挥效果而且可以安全使用的药物。
作为具有吡唑环4位被苯甲酰基取代的吡唑骨架的除草剂，在日本专利公开第173/90号公报中记载了通式[A]所示的化合物，并在WO93/18031号中记载了式[B]所示的化合物。
另外，在WO96/26206号中记载了式[C]所示的化合物。
本发明的目的在于提供一种有利于工业合成，以更低药量即可确实发挥效果，安全性高、对作物的选择性优良的除草剂。
发明概述
即，本发明是含有通式[I]所示化合物或其盐，以及该化合物的一种或两种以上作为活性成份的除草剂。
[式中，R1表示C1-6烷基。
R2表示C1-6烷硫基或C1-6烷基磺酰基。
R3、R4分别表示氢原子或C1-6烷基。
R5表示氢原子或选自下式所示基团中的一种。
(式中，R6表示卤素原子、C1-6烷基或C1-6烷氧基，n表示0、1、2、3、4或5。)
R7、R8、R9、R10分别表示氢原子或C1-6烷基。另外，(R7或R8)与(R9或R10)之间也可以形成单键。]
在上述通式[I]中，R1表示甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基等C1-6烷基。
R2表示甲硫基、乙硫基、丙硫基、异丙硫基等C1-6烷硫基，如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基等C1-6烷基磺酰基。
R3和R4分别独立的表示氢原子或甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基等C1-6烷基。
R5表示氢原子或上述式表示的基团。更具体的说，例如可以带有取代基R6的苯磺酰基、可以带有取代基R6的苯甲基、可以带有取代基R6的苯甲酰甲基等。
作为更优选的例子，例如苯磺酰基、甲苯磺酰基、2，4，6-三甲基苯磺酰基、苯甲基、4-氯苯甲基、4-甲基苯甲基、4-甲氧基苯甲基、苯甲酰甲基、4-甲基苯甲酰甲基和3，5-二氯苯甲酰甲基等。
R6表示氢原子，氟、氯、溴等卤素原子，甲基、乙基、丙基、异丙基正丁基、仲丁基、叔丁基等C1-6烷基，或甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、叔丁氧基等C1-6烷氧基。
R7、R8、R9和R10分别表示氢原子或甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基等C1-6烷基。
另外，(R7或R8)和(R9或R10)之间也可以形成单键。
另外，本发明还提供上述通式[I]所示化合物的原料，即通式(1)所示苯甲酸或苯甲酸酯。
(式中，R1、R2、R7～R10与上述含义相同，R表示氢原子或C1-6烷基。)
通式(1)中R1、R2、R7～R10与上述含义相同。
R表示氢原子或甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、戊基、己基等直链或支链状C1-6烷基。
发明的最佳实施例
本发明的化合物可以按照以下方法制备。
(式中，R1～R5，R7～R10与上述含义相同。Q表示氢原子、烷基羰基氧基、羟乙基羰基氧基或苯甲酰氧基，L表示卤素原子。)
在反应中，化合物[VIIa]和[VIIb]可以通过使用化合物[V]和化合物[VIa](Q与上述含义相同)各1摩尔或一方过剩，在1摩尔或过剩的碱存在下进行反应得到。
该反应所使用的碱，例如KOH、NaOH等碱金属氢氧化物、碳酸钠，碳酸钾等碱金属碳酸盐，氢氧化钙、氢氧化镁等碱土金属氢氧化物，碳酸钙等碱金属碳酸盐，三乙胺、二异丙基乙胺等三(C1-6烷基)胺、吡啶等有机碱，磷酸钠等。
另外，作为溶剂可以使用水、二氯甲烷、氯仿、甲苯、乙酸乙酯、二甲基甲酰胺(DMF)、四氢呋喃(THF)、二甲氧基乙烷(DME)、乙腈等。
在0℃～50℃下搅拌反应混合物，直到反应结束。另外，使用季铵盐等相间移动催化剂，在两相系中进行反应。
而且，化合物[VIIa]和[VIIb]可以通过化合物[V]和化合物[VIb]在二环己基碳化二亚胺(DCC)等脱水缩合剂存在下反应得到。
该反应所使用的溶剂例如二氯甲烷、氯仿、甲苯、乙酸乙酯、DMF、THF、DME、乙腈、叔戊醇等。
在-10℃～50℃下搅拌反应混合物，直到反应结束。按照常规方法对反应混合物进行处理。
化合物[VIIa]和[VIIb]作为混合物用于以下的重排反应。
重排反应在氰化合物和温和的碱的存在下进行。即，使化合物[VIIa]和[VIIb]1摩尔与1～4摩尔(优选1～2摩尔)的碱和0.01～1.0摩尔(优选0.05～0.2摩尔)的氰化合物进行反应，得到[Ia]所示的化合物。
这里使用的碱例如KOH、NaOH等碱金属氢氧化物、碳酸钠，碳酸钾等碱金属碳酸盐，氢氧化钙、氢氧化镁等碱土金属氢氧化物，碳酸钙等碱金属碳酸盐，三乙胺、二异丙基乙胺等三(C1-6烷基)胺、吡啶等有机碱，磷酸钠等。
另外，作为氰化合物可以使用***、***、乙酰氰醇、氰化氢、含有***的聚合物等。另外，通过加入少量冠醚等相间移动催化剂，使反应在更短的时间内结束。
反应在低于80℃的温度下，优选在室温至40℃的温度范围内进行。反应所使用的溶剂为1，2-二氯乙烷、甲苯、乙腈、二氯甲烷、氯仿、乙酸乙酯、DMF、甲基异丁基酮、THF、DME等。
另外，该重排反应也可以在惰性溶剂中，在碳酸钾、碳酸钠、三乙胺、吡啶等碱的存在下进行。反应中所用碱的量相对于化合物[VIIa]和[VIIb]为0.5～2.0摩尔，溶剂可以使用THF、二氧六环、叔戊醇、叔丁醇等。反应温度优选室温至所用溶剂的沸点。
而且，化合物[Ia]也可以通过不从化合物[V]和化合物[VIb]中分离化合物[VIIa]和[VIIb]，使用DCC等脱水缩合剂和碱制得。该反应中使用的碱为碳酸钾、碳酸钠、三乙胺、吡啶等，所用碱的量相对于化合物[V]优选0.5～2.0摩尔。另外，溶剂为THF、二氧六环、叔戊醇、叔丁醇等，反应温度优选室温至所用溶剂的沸点。
化合物[I]可以通过使化合物[Ia]与R5L(R5，L与上述含义相同)所示化合物在碱存在下进行反应制得。该反应中使用的碱为KOH、NaOH等碱金属氢氧化物，碳酸钠，碳酸钾等碱金属碳酸盐，氢氧化钙、氢氧化镁等碱土金属氢氧化物，碳酸钙等碱土金属碳酸盐，三乙胺、二异丙基乙胺等三(C1-6烷基)胺、吡啶等有机碱，磷酸钠等。
作为溶剂可以使用二氯甲烷、氯仿、甲苯、乙酸乙酯、DMF、THF、DME、乙腈等。
在0℃至所用溶剂的沸点的温度下进行反应直到反应结束。另外，也可以通过使用季铵盐等相间移动催化剂，在水和上述溶剂中不溶于水的溶剂组成的二相系中进行反应制备。
通式[V]所示5-羟基吡唑类可以按照日本专利公开第234069/87号公报或日本专利公开第44375/91号公报中记载的下述方法制备。
其次，制备本发明化合物的重要中间体通式(1)所示化合物可以按照下述方法制备。
(式中，R1、R2、R7、R8、R9和R10与上述含义相同，R13表示低级烷基。)
通式(1)所示二氢异噁唑化合物可以通过下述方法制备，使醛肟化合物(2)与氯、溴、N-氯代琥珀酰亚胺(NCS)、N-溴代琥珀酰亚胺(NBS)等卤化剂在苯、甲苯等烃类；THF、二氧六环等醚类；乙腈等腈类或DMF等溶剂中，在-10℃～50℃反应后，使之与三乙胺等有机碱或碳酸氢钠、碳酸钾等碳酸盐等碱进行反应，形成氧化腈化合物(3)，使该物质与通式(4)(R7、R8、R9和R10与上述含义相同，优选氢原子或甲基。)所示化合物在常压下或使用高压釜等加压容器在加压条件下，在化合物(4)的存在下，在-10℃～150℃的温度下进行反应。另外，上述氧化腈化合物(3)也可以通过使醛肟化合物(2)与次氯酸钠等次卤酸盐进行反应制得。
(式中，R1、R2、R13与上述含义相同，R11、R12与上述R7、R8、R9或R10相对应。)
通式(7)所示异噁唑化合物可以通过下述方法制备，使醛肟化合物(2)与氯、溴、N-氯代琥珀酰亚胺(NCS)、N-溴代琥珀酰亚胺(NBS)等卤化剂在苯、甲苯等烃类；二氯甲烷、氯仿等卤代烃类；THF、二氧六环等醚类；乙腈等腈类；或DMF等溶剂中，在-10℃～50℃下反应后，使之与三乙胺等有机碱、或碳酸钠、碳酸钾等碳酸盐等碱进行反应，形成氧化腈化合物(3)，使该物质与取代醋酸乙烯酯(8)或取代乙炔(9)在-10℃至所用溶剂沸点的温度范围内进行反应。
另外，使上述醛肟化合物(2)与卤化剂进行反应得到的卤化物在取代醋酸乙烯酯(8)或取代乙炔(9)的存在下与上述碱进行反应也可以制得异噁唑化合物(7)。
(式中，R1、R7、R8、R9、R10和R13与上述含义相同，R5表示C1-6烷基。)
式(I-1)所示苯甲酸类可以通过下述方法制备，在碱存在下使R’SH所示硫醇对式(I-2)所示4-CI型化合物作用，形成式(I-3)所示4-SR’型化合物后，将该物质氧化。
该反应中所使用的碱例如氢氧化钠、氢氧化钾等碱金属氢氧化物，甲醇钠、乙醇钠等金属醇化物，碳酸钠、碳酸钾等碳酸盐，氢化钠等氢化物，三乙胺、二异丙基乙胺、1，8-二氮杂二环[5，4，0]十一碳-7-烯(DBU)、吡啶等有机碱。另外，反应所使用的溶剂例如甲醇和乙醇等醇类，THF和DME等醚类，DMF和二甲基乙酰胺等酰胺类，苯、甲苯、二甲苯等烃类，二甲基亚砜(DMSO)和乙腈等。
以下的氧化反应可以在水；醋酸等有机酸；二氯甲烷、氯仿或四氯化碳等卤代烃等惰性溶剂中，使用过氧化氢、过醋酸、过苯甲酸和间氯过苯甲酸等过酸；次氯酸钠、次氯酸钾等次氯酸盐等氧化剂进行。反应在室温至所用溶剂沸点的温度范围内顺利进行。
如果化合物[I]含有游离的羟基时，由该化合物可以衍生出其盐，特别是农业上可接受的盐。作为农业上可接受的盐例如钠、钾、钙和铵等盐。
作为铵盐的例子，例如与式：N+RaRbRcRd(式中Ra、Rb、Rc和Rd分别表示氢或根据情况表示被羟基等取代的C1-10烷基)所示离子形成的盐。Ra、Rb、Rc和Rd中的任何一个根据情况表示被取代的烷基时，它们优选含有1～4个碳原子。
这些衍生物可以按照常规方法制备。
本发明的化合物[Ia]能够以如下研述的多种互变异构体的形式存在。所述形式全部包括在本发明的范围内。
(式中R1、R2、R3、R4、R7、R8、R9和R10与上述含义相同。)
本发明化合物以及各种中间体等在反应结束后，可以通过常规的后处理得到。
本发明化合物以及各种中间体等的结构是通过IR、NMR和MS等确定的。
(除草剂)
本发明化合物也包括在栽培条件下，采用土壤处理或茎叶处理任意一种方法均显示较高的除草活性，对马唐、莎草、黄麻、野苋等各种田地杂草有效，对玉米、麦、大豆、棉等作物具有选择性的化合物。
另外，本发明化合物也包括对作物、观赏用植物和果树等有用植物具有控制生长作用等植物生长调节作用的化合物。
另外，本发明化合物也包括对水田杂草的ノビェ、伞形植物、慈姑和镳草等各种水田杂草具有优良的杀草效力，对稻具有选择性的化合物。
而且，本发明化合物也适用于果树园、草坪、轨道端、空地等的杂草的防除。
本发明化合物中也包括具有调节植物生长作用、杀菌活性、杀虫和杀蜱螨活性的物质。
本发明除草剂含有本发明化合物的一种或多种作为活性成份。在实际使用本发明化合物时，可以不加入其它成份，以纯物质的形态使用，也可以作为农药根据使用目的制成一般农药可以制成的剂型使用，即水合剂、颗粒剂、粉末剂、乳剂、水溶剂、悬浊剂、フロァブル等。以固体剂型为例，作为添加剂和载体，可以使用大豆粉、小麦粉等植物性粉末，硅藻土、磷灰石、石膏、滑石、膨润土、叶蜡石和粘土等矿物性粉末，苯甲酸钠、尿素、芒硝等有机和无机化合物。以液体剂型为例，可以使用煤油、二甲苯、溶剂石脑油等石油馏分，环己烷、环己酮、DMF、DMSO、乙醇、丙酮、三氯乙烯、甲基异丁基酮、矿物油、植物油、水等作为溶剂。为了使这些制剂达到均一而且稳定的状态，必要时也可以添加表面活性剂。作为表面活性剂没有特别的限定，例如聚氧乙烯烷基苯基醚、聚氧乙烯烷基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯三苯乙烯基苯基醚等非离子表面活性剂，聚氧乙烯烷基苯基醚的硫酸酯盐、烷基苯磺酸盐、高级醇硫酸酯盐、烷基硫酸盐、烷基萘磺酸盐、多羧酸盐、木质素磺酸盐、烷基萘磺酸盐的甲醛缩合物、异丁烯-马来酸酐的共聚物等。
本发明除草剂中活性成份的浓度根据上述制剂形态的不同，变化为各种不同的浓度。例如，在水合剂中采用5～90重量％(以下简写为％)的浓度，优选10～85％；在乳剂中采用3～70％的浓度，优选5～60％；在颗粒剂中采用0.01～50％的浓度，优选0.05～40％。
这样得到的水合剂或乳剂可以用水稀释到规定的浓度，制成悬浊液或乳浊液，颗粒剂可以在杂草发芽前后直接进行喷撒处理或混合处理。实际上使用本发明除草剂时，每公顷施用活性成份0.1g以上。
另外，本发明的除草剂也可以与公知的杀菌剂、杀虫剂、杀蜱螨剂、除草剂、植物生长调节剂和肥料等混合后使用。特别是通过与除草剂混合使用，有可能减少使用药量。另外，不仅省力，而且还可以通过药物的协同作用得到更高的效果。这时，也可以与两种或多种公知除草剂组合。
与本发明除草剂混合使用的适当药物例如シフルフェニカン和敌稗(propanil)等酰基苯胺类除草剂，甲草胺(alachlor)和丙草胺(pretilachlor)等氯乙酰苯胺类除草剂，2，4-D和2，4-DB等芳基氧链烷酸类除草剂，氯甲草(diclofop-methyl)、高恶唑禾草灵(fenoxaprop-ethyl)等芳基氧苯氧基链烷酸类除草剂，麦草畏(dicamba)和嘧硫苯甲酸钠(pyrithiobac)等芳基链烷酸类除草剂，灭草喹(imazaquin)和咪草烟(imazethapyr)等咪唑啉酮类除草剂，敌草隆(diuron)和异丙隆(isoproturon)等尿素类除草剂，氯苯胺灵(chlorproham)和苯敌草(phenmedipham)等氨基甲酸酯类除草剂，杀草丹(thiobencarb)和EPTC等硫代氨基甲酸酯类除草剂，氟乐灵(trifluralin)和ベンジメタリン等二硝基苯胺类除草剂，氟锁草醚(acifluorfen)和氟黄胺草醚(fomesafen)等二苯基醚类除草剂，苄嘧磺隆(bensulfuron methyl)和烟嘧黄隆(nicosulfuron)等磺酰脲类除草剂，塞克津(metribuzin)和メタトロン等三嗪酮类除草剂，莠去津(atrazine)和氰乙酰肼(cyanazine)等三嗪类除草剂，氟唑啶草(flumetsulam)等叠氮基嘧啶类除草剂，溴草腈(bromoxynil)、敌草腈(dichlobenil)等腈类除草剂，草甘膦(glyphosate)、グリホシネ-ト等磷酸类除草剂，对草快(paraquat)、苯敌快(difenzoquat)等季铵盐类除草剂，酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)和达草氟(fluthiacet-methyl)等环亚胺类除草剂，其它异噁草胺(isoxaben)、乙呋草黄(ethofumesate)、噁草灵(oxadiazon)、二氯喹啉酸(quinclorac)、异噁草酮(clomazone)、磺草酮(sulcotrione)、环庚草醚(cinmethylin)、氟硫草定(dithiopyr)、吡唑特(pyrazolate)、达草止(pyridate)、胺草唑(flupoxam)、苯达松(bentazone)、呋草黄(benfuresate)，以及稀禾定(sethoxydim)和肟草酮(tralkoxydim)等环己烷二酮类除草剂等。另外，在这些组合物质中也可以加入植物油和油浓缩物。
(实施例)
以下结合参考例、实施例， 更详细的说明本发明化合物。
参考例1
3-溴代甲基-4-甲磺酰基-2-甲基苯甲酸甲酯的制备
将2，3-二甲基-4-甲磺酰基苯甲酸甲酯29.69g溶解在四氯化碳260ml中，加入NBS 22.93g及过氧化苯甲酰基1.0g，加热回流2.5小时。冷却反应液后，过滤除去不溶物，减压浓缩滤液，得到粘稠油状物56.58g。采用硅胶柱色谱法(n-己烷/乙酸乙酯＝5/1)精制该物质，得到白色晶体状标题化合物18.98g。
参考例2
3-甲酰基-4-甲磺酰基-2-甲基苯甲酸甲酯的制备
将3-溴代甲基-4-甲磺酰基-2-甲基苯甲酸甲酯18.90g溶解在乙腈180ml中，室温下用10分钟添加N-甲基吗啉氧化物20.67g。直接在室温下搅拌1小时后，将反应液倒入冰水中，用浓盐酸调节至酸性，用苯萃取。用水、饱和食盐水洗涤有机层，用无水硫酸镁干燥后，减压蒸馏除去溶剂，得到白色晶体状标题化合物11.59g。用乙醇洗涤粗产物，得到标题化合物的白色晶体。m.p.108～110℃。
参考例3
3-甲酰基-4-甲磺酰基-2-甲基苯甲酸甲酯的制备
向20ml甲醇中加入28％的甲醇钠的甲醇溶液2.60g，室温下滴加2-硝基丙烷1.30g。接着，添加3-溴代甲基-4-甲磺酰基-2-甲基苯甲酸甲酯4.40g后，加热回流1小时。冷却后，向反应液中加入1N盐酸50ml，用乙酸乙酯萃取。用饱和食盐水洗涤有机层，用无水硫酸镁干燥。减压蒸馏除去溶剂，得到晶体状标题化合物3.10g。m.p.108～110℃。
参考例4
3-羟亚氨基甲基-4-甲磺酰基-2-甲基苯甲酸甲酯的制备
将3-甲酰基-4-甲磺酰基-2-甲基苯甲酸甲酯11.55g溶解在乙醇100ml中，加入羟胺盐酸盐4.70g，室温下放置1.5小时，再加热回流1小时。冷却反应液后，减压蒸馏除去乙醇，用乙酸乙酯溶解残渣。用水和饱和食盐水洗涤乙酸乙酯溶液，用无水硫酸镁干燥，减压蒸馏除去溶剂，得到粘稠油状粗产物12.31g。将该物质用硅胶柱色谱法(n-己烷/乙酸乙酯＝2/1)精制，得到白色晶体状标题化合物。m.p.123～129℃。
实施例1
3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸甲酯的制备
将粗3-羟亚氨基甲基-4-甲磺酰基-2-甲基苯甲酸甲酯6.00g溶解在氯仿100ml中，搅拌、-3℃～3℃的条件下，通入氯气35分钟。再在0℃下搅拌30分钟后，向反应液中通入氮气，以除去过剩的氯气，然后再减压蒸馏除去氯仿，得到粘稠的油状物。将其溶解在***90ml中，在搅拌、-10℃的条件下，通入乙烯5分钟。接着，在-10℃，滴加三乙胺7ml及***7ml，再通入乙烯20分钟。将该反应混合物移至预先冷却的200ml不锈钢制高压釜中，在60～70℃下，搅拌3.5小时。冷却后，将反应液倒入水中，用盐酸调节至酸性后，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层，用无水硫酸镁干燥后，减压蒸馏除去溶剂。将得到的粗产物用硅胶柱色谱法(n-己烷/乙酸乙酯＝2/1)精制，得到白色晶体状标题化合物3.20g。m.p.104～106.5℃。
实施例2
3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸的制备
向3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸甲酯3.00g中加入乙醇10ml和1N氢氧化钠溶液20ml，室温下搅拌2天。减压蒸馏除去乙醇后，用盐酸调节至酸性，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层，用无水硫酸镁干燥后，减压蒸馏除去溶剂，得到白色晶体状标题化合物2.75g。m.p.182～184.5℃。
实施例3
3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸甲酯的制备方法
将粗3-羟亚氨基甲基-4-甲磺酰基-2-甲基苯甲酸甲酯2.00g溶解在35ml氯仿中，在搅拌、-13～0℃的条件下，通入氯气30分钟。再在0℃下搅拌30分钟后，向反应液中通入氮气，以除去过剩的氯气，在减压的条件下，浓缩氯仿，得到固体。将该物质溶解在50ml***中，在搅拌、-11℃的条件下，通入乙炔气体5分钟。接着，在-15～-13.5℃下，滴加溶于***5ml中的三乙胺1.64g，再在-15～-13.5℃下，通入乙炔气体20分钟。将此反应混合物移至预先冷却的50ml不锈钢制高压釜中，在60～70℃下，搅拌3.5小时。冷却后，将反应液加入至水中，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层，用无水硫酸镁干燥后，减压蒸馏除去溶剂。将得到的残渣用硅胶柱色谱法(苯/乙酸乙酯＝9/1)精制，得到白色晶体状标题化合物0.82g。m.p.87～89℃。
实施例4
3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸的制备方法
向3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸甲酯0.80g中加入乙醇8ml和1N氢氧化钠溶液8ml，室温下搅拌2天。将反应液倒入冰水中，用盐酸调节至酸性，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层，用无水硫酸镁干燥后，减压蒸馏除去溶剂，得到白色晶体状标题化合物0.56g。m.p.150～151℃。
包括上述实施例，本发明化合物的例子如表1所示。
表1
| 化合物序 号 | R | R2 | R7 | R8 | R9 | R10 | 融点(℃) |
| 1 | H | SO2CH3 | H | H | H | H | [182-184.5] |
| 2 | CH3 | SO2CH3 | H | H | H | H | [104-106.5] |
| 3 | C2H5 | SO2CH3 | H | H | H | H | |
| 4 | C3H7 | SO2CH3 | H | H | H | H | |
| 5 | i-C3H7 | SO2CH3 | H | H | H | H | |
| 6 | C4H9 | SO2CH3 | H | H | H | H | |
| 7 | t-C4H9 | SO2CH3 | H | H | H | H | |
| 8 | H | SO2CH3 | H | H | CH3 | H | [133-134] |
| 9 | CH3 | SO2CH3 | H | H | CH3 | H | [85-87] |
| 10 | C2H5 | SO2CH3 | H | H | H | H | |
| 11 | C3H7 | SO2CH3 | H | H | H | H | |
| 12 | i-C3H7 | SO2CH3 | H | H | H | H | |
| 13 | C4H9 | SO2CH3 | H | H | H | H | |
| 14 | t-C4H9 | SO2CH3 | H | H | H | H | |
| 15 | H | SO2CH3 | CH3 | H | H | H | |
| 16 | CH3 | SO2CH3 | CH3 | H | H | H | |
| 17 | H | SO2CH3 | H | H | C2H5 | H | |
| 18 | CH3 | SO2CH3 | H | H | C2H5 | H |
表1(续)
(R1＝CH3)
| 化合物序 号 | R | R2 | R7 | R8 | R9 | R10 | 融点(℃) |
| 19 | H | SO2CH3 | CH3 | H | CH3 | H | |
| 20 | CH3 | SO2CH3 | CH3 | H | CH3 | H | |
| 21 | H | SO2CH3 | H | H | i-C3H | H | |
| 22 | CH3 | SO2CH3 | H | H | i-C3H7 | H | |
| 23 | H | SO2CH3 | H | H | CH3 | CH3 | |
| 24 | CH3 | SO2CH3 | H | H | CH3 | CH3 | |
| 25 | C2H5 | SO2CH3 | H | H | CH3 | CH3 | |
| 26 | H | SO2CH3 | H | H | CH3 | C2H5 | |
| 27 | CH3 | SO2CH3 | H | H | CH3 | C2H5 | |
| 28 | H | SO2CH3 | H | H | C2H5 | C2H5 | |
| 29 | CH3 | SO2CH3 | H | H | C2H5 | C2H5 | |
| 30 | H | SO2CH3 | CH3 | C2H5 | H | H | |
| 31 | CH3 | SO2CH3 | CH3 | C2H5 | H | H | |
| 32 | H | SO2CH3 | C2H5 | C2H5 | H | H | |
| 33 | CH3 | SO2CH3 | C2H5 | C2H5 | H | H | |
| 34 | H | SO2CH3 | CH3 | CH3 | H | H | |
| 35 | CH3 | SO2CH3 | CH3 | CH3 | H | H | |
| 36 | H | SO2CH3 | H | H | H | H | |
| 37 | CH3 | SO2CH3 | H | H | H | H | |
| 38 | H | SO2CH3 | H | H | H | H | |
| 39 | CH3 | SO2CH3 | H | H | H | H | |
| 40 | H | SO2CH3 | H | H | H | H | |
| 41 | CH3 | SO2CH3 | H | H | H | H | |
| 42 | CH3 | SO2CH3 | H | H | H | H |
表1(续)
(R1＝CH3)
| 化合物序 号 | R | R2 | R7 | R8 | R9 | R10 | 融点(℃) |
| 43 | H | SO2CH3 | H | 单键 | H | [150-151] | |
| 44 | CH3 | SO2CH3 | H | 单键 | H | [87-89] | |
| 45 | C2H5 | SO2CH3 | H | 单键 | H | ||
| 46 | i-C3H7 | SO2CH3 | H | 单键 | H | ||
| 47 | C4H9 | SO2CH3 | H | 单键 | H | ||
| 48 | t-C4H9 | SO2CH3 | H | 单键 | H | ||
| 49 | H | SO2CH3 | CH3 | 单键 | H | ||
| 50 | CH3 | SO2CH3 | CH3 | 单键 | H | ||
| 51 | H | SO2CH3 | H | 单键 | CH3 | [158-162] | |
| 52 | CH3 | SO2CH3 | H | 单键 | CH3 | [100-105] | |
| 53 | C2H5 | SO2CH3 | H | 单键 | CH3 | ||
| 54 | i-C3H7 | SO2CH3 | H | 单键 | H | ||
| 55 | C4H9 | SO2CH3 | H | 单键 | H | ||
| 56 | t-C4H9 | SO2CH3 | H | 单键 | H | ||
| 57 | H | SO2CH3 | CH3 | 单键 | CH3 | ||
| 58 | CH3 | SO2CH3 | CH3 | 单键 | CH3 | ||
| 59 | H | SO2CH3 | H | 单键 | C2H5 | ||
| 60 | CH3 | SO2CH3 | H | 单键 | C2H5 | ||
| 61 | H | SO2CH3 | C2H5 | 单键 | H | ||
| 62 | CH3 | SO2CH3 | C2H5 | 单键 | H | ||
| 63 | H | SO2CH3 | CH3 | 单键 | C2H5 | ||
| 64 | CH3 | SO2CH3 | CH3 | 单键 | C2H5 | ||
| 65 | H | SO2CH3 | H | 单键 | i-C3H7 | ||
| 66 | CH3 | SO2CH3 | H | 单键 | i-C3H7 | ||
实施例5
4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-5-羟基-1-甲基吡唑(化合物序号1-1)的制备
向3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸2.75g中加入苯30ml，再加入亚硫酰氯1.7ml和吡啶1滴，加热回流3小时。冷却反应液后，减压蒸馏除去溶剂，得到3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯2.90g。接着，将5-羟基-1-甲基吡唑盐酸盐0.93g溶解在氯仿20ml中，在冰水浴条件下，加入三乙胺1.60g。再向其中滴加3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯1.90g的氯仿10ml溶液，室温下搅拌30分钟后，加入三乙胺0.76g和丙酮氰醇0.16g，再搅拌一夜。用稀盐酸、饱和食盐水洗涤反应液后，用无水硫酸镁干燥。减压蒸馏除去溶剂，向残渣中加入甲醇，过滤收集得到晶体，得到白色晶体状标题化合物1.59g。m.p.224～226℃。
实施例6
4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-1-乙基-5-羟基吡唑(化合物序号1-9)的制备
向3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸2.75g中加入苯30ml，再加入亚硫酰氯1.7ml和吡啶1滴后，加热回流3小时。冷却反应液后，减压蒸馏除去溶剂，得到3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯2.90g。接着，将1-乙基-5-羟基吡唑盐酸盐0.93g溶解在氯仿20ml中，在冰水浴条件下，加入三乙胺1.60g。再向其中滴加3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯1.90g的氯仿10ml溶液，室温下搅拌30分钟后，加入三乙胺0.76g和丙酮氰醇0.16g，再搅拌一夜。用稀盐酸、饱和食盐水洗涤反应液后，用无水硫酸镁干燥。减压蒸馏除去溶剂，向残渣中加入甲醇，过滤收集得到晶体，得到白色晶体状标题化合物1.59g。m.p.183～184.5℃。
实施例7
5-苯甲基-4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-1-甲基吡唑(化合物序号1-4)的制备
将4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-5-羟基-1-甲基吡唑0.45g溶解在DMF 15ml中，加入碳酸钾0.26g，接着加入溴化苯甲基0.25g。室温下搅拌一夜后，将反应液倒入冰水中，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层后，用无水硫酸镁干燥。减压蒸馏除去溶剂，向残渣中加入甲醇，过滤收集得到的晶体，得到白色晶体状标题化合物0.42g。m.p.151.5～153℃。
实施例8
4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-1-乙基-5-苯甲酰甲基氧吡唑(化合物序号1-11)的制备
将4-[3-(4，5-二氢异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]-1-乙基-5-羟基吡唑0.20g溶解在DMF 10ml中，加入碳酸钾0.11g，接着加入苯甲酰甲基溴0.13g。室温下搅拌一夜后，将反应液倒入冰水中，用乙酸乙酯萃取。用水、饱和食盐水洗涤有机层后，用无水硫酸镁干燥。减压蒸馏除去溶剂，向残渣中加入甲醇，过滤收集得到的晶体，得到白色晶体状标题化合物0.17g。m.p.177～179℃。
实施例9
1-乙基-5-羟基-4-[(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰基]吡唑(化合物序号2-9)的制备
向3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酸0.55g中加入苯10ml，加入亚硫酰氯0.17ml及三乙胺1滴后，加热回流2小时。冷却反应液后，减压蒸馏除去溶剂，得到3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯。
接着，将1-乙基-5-羟基吡唑盐酸盐0.38g溶解在氯仿10ml中，在冰水浴条件下，加入三乙胺0.52g。再向其中滴加先前得到的3-(异噁唑-3-基)-4-甲磺酰基-2-甲基苯甲酰氯的氯仿5ml溶液，室温下搅拌1小时。再向反应混合物中加入三乙胺0.26g及丙酮氰醇0.05g，再搅拌一夜。将反应液用稀盐酸、水、饱和食盐水洗涤后，用无水硫酸镁干燥。减压蒸馏除去溶剂，向得到的残渣中加入甲醇，过滤收集得到的晶体，得到白色晶体状标题化合物0.18g。m.p.85～88℃。
包括上述实施例，本发明化合物的例子如表2及表3所示。
表2
(R8，R10＝H)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7 | R9 | 融点(℃) |
| 1-1 | CH3 | SO2CH3 | H | CH3 | H | H | H | [224-226] |
| 1-2 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | |
| 1-3 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | |
| 1-4 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | H | [151.5-153] |
| 1-5 | CH3 | SO2CH3 | CH3 | CH3 | H | H | H | |
| 1-6 | CH3 | SO2CH3 | CH3 | CH3 | 甲苯磺酰基 | H | H | |
| 1-7 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲酰甲基 | H | H | |
| 1-8 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲基 | H | H | |
| 1-9 | CH3 | SO2CH3 | H | C2H5 | H | H | H | [183-184.5] |
| 1-10 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | H | H | |
| 1-11 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | H | H | [177-179] |
| 1-12 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | H | H | |
| 1-13 | CH3 | SO2CH3 | H | CH3 | H | CH3 | H | |
| 1-14 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | H | |
| 1-15 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | H | |
| 1-16 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | H | |
| 1-17 | CH3 | SO2CH3 | H | CH3 | H | H | CH3 | [183-185] |
表2(续)
(R8，R10＝H)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7 | R9 | 融点(℃) |
| 1-18 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | CH3 | |
| 1-19 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | CH3 | |
| 1-2O | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | CH3 | |
| 1-21 | CH3 | SO2CH3 | H | CH3 | H | CH3 | CH3 | |
| 1-22 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | CH3 | |
| 1-23 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | CH3 | |
| 1-24 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | CH3 | |
| 1-25 | CH3 | SO2CH3 | H | C2H5 | H | CH3 | H | |
| 1-26 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | CH3 | H | |
| 1-27 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | CH3 | H | |
| 1-28 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | CH3 | H | |
| 1-29 | CH3 | SO2CH3 | H | C2H5 | H | H | CH3 | |
| 1-30 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | H | CH3 | |
| 1-31 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | H | CH3 | |
| 1-32 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | H | CH3 | |
| 1-33 | CH3 | SO2CH3 | H | C2H5 | H | CH3 | CH3 | |
| 1-34 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | CH3 | CH3 | |
| 1-35 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | CH3 | CH3 | |
| 1-36 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | CH3 | CH3 | |
| 1-37 | CH3 | SO2CH3 | CH3 | CH3 | H | CH3 | CH3 | |
| 1-38 | CH3 | SO2CH3 | CH3 | CH3 | 甲苯磺酰基 | CH3 | CH3 | |
| 1-39 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲酰甲基 | CH3 | CH3 | |
| 1-40 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲基 | CH3 | CH3 | |
| 1-41 | CH3 | SO2CH3 | CH3 | CH3 | H | H | i-Pr |
表2(续)
(R8，R10＝H)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7 | R9 | 融点(℃) |
| 1-42 | C2H5 | SO2CH3 | H | CH3 | H | H | H | |
| 1-43 | C2H5 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | |
| 1-44 | C2H5 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | |
| 1-45 | C2H5 | SO2C2H5 | H | CH3 | 苯甲基 | H | H | |
| 1-46 | CH3 | SO2C2H5 | H | CH3 | H | H | H | |
| 1-47 | CH3 | SO2C2H5 | H | CH3 | 甲苯磺酰基 | H | H | |
| 1-48 | CH3 | SO2C2H5 | CH3 | CH3 | 苯甲酰甲基 | H | H | |
| 1-49 | CH3 | SO2C2H5 | CH3 | CH3 | 苯甲基 | H | H | |
| 1-50 | CH3 | SO2C3H7 | H | CH3 | H | H | CH3 | |
| 1-51 | CH3 | SO2C3H7 | H | CH3 | 甲苯磺酰基 | H | CH3 | |
| 1-52 | CH3 | SO2C3H7 | H | CH3 | 苯甲酰甲基 | H | CH3 | |
| 1-53 | CH3 | SO2C3H7 | H | CH3 | 苯甲基 | H | CH3 | |
| 1-54 | CH3 | SO2i-Pr | H | CH3 | H | CH3 | H | |
| 1-55 | CH3 | SO2i-Pr | H | CH3 | 甲苯磺酰基 | CH3 | H | |
| 1-56 | CH3 | SO2i-Pr | H | CH3 | 苯甲酰甲基 | CH3 | H | |
| 1-57 | CH3 | SO2i-Pr | H | CH3 | 苯甲基 | CH3 | H | |
| 1-58 | CH3 | SO2t-Bu | H | CH3 | H | H | H | |
| 1-59 | CH3 | SO2CH3 | H | Pr | H | H | H | |
| 1-60 | CH3 | SO2CH3 | H | i-Pr | 甲苯磺酰基 | H | H | |
| 1-61 | CH3 | SO2CH3 | H | t-Bu | 苯甲酰甲基 | H | H | |
| 1-62 | CH3 | SO2CH3 | H | Pr | 苯甲基 | H | H | |
| 1-63 | CH3 | SO2CH3 | H | CH3 | 2-Cl-苯甲基 | H | H | |
| 1-64 | CH3 | SO2CH3 | H | CH3 | 4-Me-苯甲基 | H | H | |
| 1-65 | CH3 | SO2CH3 | H | CH3 | 3-OMe-苯甲酰甲基 | H | H |
表2(续)
(R8，R10＝H)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7 | R8 | R9 | R10 |
| 1-66 | CH3 | SO2CH3 | H | CH3 | H | CH3 | CH3 | H | H |
| 1-67 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | CH3 | H | H |
| 1-68 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | CH3 | H | H |
| 1-69 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | CH3 | H | H |
| 1-70 | CH3 | SO2CH3 | H | CH3 | H | CH3 | C2H5 | H | H |
| 1-71 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | C2H5 | H | H |
| 1-72 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | C2H5 | H | H |
| 1-73 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | C2H5 | H | H |
| 1-74 | CH3 | SO2CH3 | H | CH3 | H | C2H5 | C2H5 | H | H |
| 1-75 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | C2H5 | C2H5 | H | H |
| 1-76 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | C2H5 | C2H5 | H | H |
| 1-77 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | C2H5 | C2H5 | H | H |
| 1-78 | CH3 | SO2CH3 | H | CH3 | H | H | H | CH3 | CH3 |
| 1-79 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | CH3 | CH3 |
| 1-80 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | CH3 | CH3 |
| 1-81 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | H | CH3 | CH3 |
| 1-82 | CH3 | SO2CH3 | H | CH3 | H | H | H | CH3 | C2H5 |
| 1-83 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | CH3 | C2H5 |
| 1-84 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | CH3 | C2H5 |
| 1-85 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | H | CH3 | C2H5 |
| 1-86 | CH3 | SO2CH3 | H | CH3 | H | H | H | C2H5 | C2H5 |
| 1-87 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | C2H5 | C2H5 |
| 1-88 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | C2H5 | C2H5 |
| 1-89 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | H | C2H5 | C2H5 |
表3
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7(R8) | R9(R10) | 融点(℃) |
| 2-1 | CH3 | SO2CH3 | H | CH3 | H | H | H | |
| 2-2 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | |
| 2-3 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | |
| 2-4 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | H | |
| 2-5 | CH3 | SO2CH3 | CH3 | CH3 | H | H | H | |
| 2-6 | CH3 | SO2CH3 | CH3 | CH3 | 甲苯磺酰基 | H | H | |
| 2-7 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲酰甲基 | H | H | |
| 2-8 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲基 | H | H | |
| 2-9 | CH3 | SO2CH3 | H | C2H5 | H | H | H | |
| 2-10 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | H | H | |
| 2-11 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | H | H | |
| 2-12 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | H | H | |
| 2-13 | CH3 | SO2CH3 | H | CH3 | H | CH3 | H | |
| 2-14 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | H | |
| 2-15 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | H | |
| 2-16 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | H | |
| 2-17 | CH3 | SO2CH3 | H | CH3 | H | H | CH3 | |
| 2-18 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | CH3 |
表3(续)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7(R8) | R9(R10) | 融点(℃) |
| 2-19 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | CH3 | |
| 2-20 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | H | CH3 | |
| 2-21 | CH3 | SO2CH3 | H | CH3 | H | CH3 | CH3 | |
| 2-22 | CH3 | SO2CH3 | H | CH3 | 甲苯磺酰基 | CH3 | CH3 | |
| 2-23 | CH3 | SO2CH3 | H | CH3 | 苯甲酰甲基 | CH3 | CH3 | |
| 2-24 | CH3 | SO2CH3 | H | CH3 | 苯甲基 | CH3 | CH3 | |
| 2-25 | CH3 | SO2CH3 | H | C2H5 | H | CH3 | H | |
| 2-26 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | CH3 | H | |
| 2-27 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | CH3 | H | |
| 2-28 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | CH3 | H | |
| 2-29 | CH3 | SO2CH3 | H | C2H5 | H | H | CH3 | |
| 2-30 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | H | CH3 | |
| 2-31 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | H | CH3 | |
| 2-32 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | H | CH3 | |
| 2-33 | CH3 | SO2CH3 | H | C2H5 | H | CH3 | CH3 | |
| 2-34 | CH3 | SO2CH3 | H | C2H5 | 甲苯磺酰基 | CH3 | CH3 | |
| 2-35 | CH3 | SO2CH3 | H | C2H5 | 苯甲酰甲基 | CH3 | CH3 | |
| 2-36 | CH3 | SO2CH3 | H | C2H5 | 苯甲基 | CH3 | CH3 | |
| 2-37 | CH3 | SO2CH3 | CH3 | CH3 | H | CH3 | CH3 | |
| 2-38 | CH3 | SO2CH3 | CH3 | CH3 | 甲苯磺酰基 | CH3 | CH3 | |
| 2-39 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲酰甲基 | CH3 | CH3 | |
| 2-40 | CH3 | SO2CH3 | CH3 | CH3 | 苯甲基 | CH3 | CH3 | |
| 2-41 | CH3 | SO2CH3 | CH3 | CH3 | H | H | i-Pr |
表3(续)
| 化合物序 号 | R1 | R2 | R3 | R4 | R5 | R7(R8) | R9(R10) | 融点(℃) |
| 2-42 | C2H5 | SO2CH3 | H | CH3 | H | H | H | |
| 2-43 | C2H5 | SO2CH3 | H | CH3 | 甲苯磺酰基 | H | H | |
| 2-44 | C2H5 | SO2CH3 | H | CH3 | 苯甲酰甲基 | H | H | |
| 2-45 | C2H5 | SO2C2H5 | H | CH3 | 苯甲基 | H | H | |
| 2-46 | CH3 | SO2C2H5 | H | CH3 | H | H | H | |
| 2-47 | CH3 | SO2C2H5 | H | CH3 | 甲苯磺酰基 | H | H | |
| 2-48 | CH3 | SO2C2H5 | CH3 | CH3 | 苯甲酰甲基 | H | H | |
| 2-49 | CH3 | SO2C2H5 | CH3 | CH3 | 苯甲基 | H | H | |
| 2-50 | CH3 | SO2C3H7 | H | CH3 | H | H | CH3 | |
| 2-51 | CH3 | SO2C3H7 | H | CH3 | 甲苯磺酰基 | H | CH3 | |
| 2-52 | CH3 | SO2C3H7 | H | CH3 | 苯甲酰甲基 | H | CH3 | |
| 2-53 | CH3 | SO2C3H7 | H | CH3 | 苯甲基 | H | CH3 | |
| 2-54 | CH3 | SO2i-Pr | H | CH3 | H | CH3 | H | |
| 2-55 | CH3 | SO2i-Pr | H | CH3 | 甲苯磺酰基 | CH3 | H | |
| 2-56 | CH3 | SO2i-Pr | H | CH3 | 苯甲酰甲基 | CH3 | H | |
| 2-57 | CH3 | SO2i-Pr | H | CH3 | 苯甲基 | CH3 | H | |
| 2-58 | CH3 | SO2t-Bu | H | CH3 | H | H | H | |
| 2-59 | CH3 | SO2CH3 | H | Pr | H | H | H | |
| 2-60 | CH3 | SO2CH3 | H | i-Pr | 甲苯磺酰基 | H | H | |
| 2-61 | CH3 | SO2CH3 | H | t-Bu | 苯甲酰甲基 | H | H | |
| 2-62 | CH3 | SO2CH3 | H | Pr | 苯甲基 | H | H | |
| 2-63 | CH3 | SO2CH3 | H | CH3 | 2-Cl-苯甲基 | H | H | |
| 2-64 | CH3 | SO2CH3 | H | CH3 | 4-Me-苯甲基 | H | H | |
| 2-65 | CH3 | SO2CH3 | H | CH3 | 3-OMe-苯甲酰甲基 | H | H |
(除草剂)
以下，举出几个涉及本发明除草剂的制剂例，活性成份化合物、添加剂及添加比例并不只限定于本实施例，可以在很宽的范围内变化。制剂实施例中的份数表示重量份。
实施例10水合剂
本发明的化合物 20份
胶态氧化硅 20份
硅藻土 52份
烷基硫酸苏打 8份
将以上成份均匀混合，粉碎成细末，得到活性成份为20％的水合剂。
实施例11乳剂
本发明的化合物 20份
二甲苯 55份
二甲基甲酰胺 15份
聚氧乙烯苯基醚 10份
混合、溶解以上成份，得到活性成份为20％的乳剂。
实施例12颗粒剂
本发明的化合物 5份
滑石粉 40份
粘土 38份
膨润土 10份
烷基硫酸钠 7份
将以上成份均匀混合，粉碎成细末后，造粒成直径为0.5～1.0的颗粒，得到活性成份为5％的颗粒剂。
以下列出与本发明除草剂的效果有关的实验例。
除草效果按照下述考察标准进行考察，用除草指数表示。
考察标准
除草率 除草指数
0％ 0
20～29％ 2
40～49％ 4
60～69％ 6
80～89％ 8
100％ 10
另外，1，3，5，7，9的数值分别表示0和2、2和4、4和6、6和8、8和10中间的数值。
实验例1茎叶洒布处理
在200cm2的盆中装入土壤，在表层分别播种青麻、野苋、苍耳、大狗尾草和玉米的种子，轻轻翻动土后，使之在室温下生长。各植物生长到5～25cm高时，以1000升/Ha洒布量当量，用小型喷雾器将实施例11所示乳剂的水稀释液洒布到茎叶部，使活性成份达到规定的药量。3周后，按照上述标准考察对农作物的药害和对杂草的除草效果，其结果如表4所示。
表4
化合物A：
| 化合物序号 | 药量(g/Ha) | 青麻 | 野苋 | 苍耳 | 大狗尾草 | 玉米 |
| I-1 | 63 | 10 | 10 | 10 | 10 | 0 |
| I-9 | 63 | 9 | 10 | 10 | 10 | 0 |
| I-17 | 63 | 9 | 10 | 10 | 10 | 0 |
| A | 63 | 9 | 10 | 8 | 10 | 9 |
(WO97/26206号公报记载的No.5.3化合物)
工业实用性
如上所述，本发明的化合物可以用作玉米等的选择性除草剂，是工业上有用的化合物。
Claims (3)
1.通式[I]所示的化合物或其盐，
式中，R1表示C1-6烷基；
R2表示C1-6烷基磺酰基；
R3和R4各自独立地表示氢原子或C1-6烷基；
R5表示氢原子、苯甲基或苯甲酰甲基；
R7、R8、R9、R10各自独立地表示氢原子或C1-6烷基。
2.除草剂，含有通式[I]所示化合物或其盐中的一种或多种作为活性成份：
式中，R1～R5、R7～R10与上述含义相同。
3.通式(1)所示化合物，
式中，R1、R2、R7～R10与上述含义相同，R表示氢原子或C1-6烷基。
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| EP (1) | EP1031573B2 (zh) |
| JP (2) | JP4441003B2 (zh) |
| CN (1) | CN1141306C (zh) |
| AU (1) | AU9650598A (zh) |
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| CN103788083A (zh) * | 2014-03-10 | 2014-05-14 | 中国药科大学 | 一种制备除草剂苯唑草酮的方法 |
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| EP0958291B1 (de) | 1997-01-17 | 2009-01-21 | Basf Se | 3-heteroxyclyl-substituierte benzoylderivate |
| CN1141306C (zh) * | 1997-10-30 | 2004-03-10 | 日本曹达株式会社 | 新型苯甲酰基吡唑化合物、制备中间体和除草剂 |
| PL219088B1 (pl) * | 1998-05-11 | 2015-03-31 | Basf Ag | Oksymy, sposób wytwarzania oksymów i sposób wytwarzania tioeterów |
| ES2191435T3 (es) * | 1998-06-09 | 2003-09-01 | Basf Ag | Mezcla herbicida que contiene un derivado de benzoilo 3-heterociclil-substituido. |
| JP4646403B2 (ja) * | 1998-06-16 | 2011-03-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 相乗効果を有する除草剤混合物 |
| CA2353569C (en) | 1998-12-04 | 2009-07-21 | Basf Aktiengesellschaft | 3-(heterocyclyl)-substituted benzoylpyrazoles |
| DE59903358D1 (de) | 1998-12-04 | 2002-12-12 | Basf Ag | 3-(heterocyclyl)-benzoylpyrazol-derivate |
| AR024845A1 (es) | 1999-08-06 | 2002-10-30 | Basf Ag | Derivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicida |
| JP2003520206A (ja) | 1999-12-02 | 2003-07-02 | ビーエーエスエフ アクチェンゲゼルシャフト | シクロプロピル縮合３−（４，５−ジヒドロイソオキサゾール−３−イル）置換ベンゾイルピラゾール |
| HUP0203536A3 (en) * | 1999-12-02 | 2005-03-29 | Basf Ag | 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles as herbicides |
| JP4465133B2 (ja) * | 2001-02-08 | 2010-05-19 | クミアイ化学工業株式会社 | イソオキサゾリン誘導体及びこれを有効成分とする除草剤 |
| DE10127328A1 (de) * | 2001-06-06 | 2002-12-19 | Bayer Cropscience Gmbh | Herbizide Mittel enthaltend Benzoylpyrazole und Safener |
| WO2003010165A1 (fr) * | 2001-07-24 | 2003-02-06 | Kumiai Chemical Industry Co., Ltd. | Derives d'isoxazoline et herbicides destines a un usage agricole ou horticole |
| GB0505645D0 (en) | 2005-03-18 | 2005-04-27 | Syngenta Participations Ag | Herbicidal composition |
| AR056889A1 (es) | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | Compuestos benzoilpirazol y herbicidas que los contienen |
| EP1976383A2 (en) * | 2005-12-23 | 2008-10-08 | Basf Se | A method for controlling aquatic weeds |
| PL2173742T3 (pl) * | 2007-07-06 | 2012-04-30 | Basf Se | Krystaliczna postać [3-(4,5-dihydro-3-izoksazolilo)-2-metylo-4-(metylo-sulfonylo)fenylo]-(5-hydroksy-1-metylo-1h-pirazol-4-ilo)metanonu |
| MX2010005231A (es) * | 2007-11-12 | 2010-05-27 | Du Pont | Mezcla herbicida. |
| AU2012335980C1 (en) * | 2011-11-07 | 2017-12-14 | Sunovion Pharmaceuticals Inc. | Modulators of opioid receptors and methods of use thereof |
| CN104521983A (zh) * | 2014-12-22 | 2015-04-22 | 京博农化科技股份有限公司 | 一种苯唑草酮与呋草酮的除草组合物 |
| CN104876920A (zh) * | 2015-05-06 | 2015-09-02 | 河南大学 | 异噁唑类化合物、中间体及其制备方法和应用 |
| CN105399674B (zh) * | 2015-12-31 | 2017-02-15 | 青岛清原化合物有限公司 | 吡唑类化合物或其盐、制备方法、除草剂组合物及用途 |
| CN107652247B (zh) * | 2017-11-15 | 2020-11-03 | 黄河三角洲京博化工研究院有限公司 | 一种2-甲基-3-[4,5-二氢异噁唑]-4-甲磺酰基苯甲酸乙酯的制备方法 |
| CN111285863B (zh) * | 2018-12-07 | 2022-04-26 | 青岛清原化合物有限公司 | 4-(3-杂环基-1-苯甲酰基)吡唑类化合物或其盐、制备方法、除草剂组合物及用途 |
| CN114057715A (zh) * | 2021-11-22 | 2022-02-18 | 安徽宁亿泰科技有限公司 | 一种苯唑草酮的制备方法 |
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| IL85659A (en) * | 1987-03-17 | 1992-03-29 | Nissan Chemical Ind Ltd | 4-benzoylpyrazole derivatives,method for their preparation and herbicidal compositions containing them |
| ATE180257T1 (de) | 1992-03-03 | 1999-06-15 | Idemitsu Kosan Co | Pyrazolderivate |
| GEP20002093B (en) * | 1995-02-24 | 2000-05-10 | Basf Ag | Pyrazol-4-yl-Benzoyl Derivatives and Herbicides Containing Them |
| CA2211534C (en) * | 1995-02-24 | 2004-10-26 | Basf Aktiengesellschaft | Isoxazolyl-benzoyl derivatives |
| CN1216534A (zh) * | 1996-04-26 | 1999-05-12 | 日本曹达株式会社 | 杂环取代的新颖苯衍生物和除草剂 |
| EP0958291B1 (de) * | 1997-01-17 | 2009-01-21 | Basf Se | 3-heteroxyclyl-substituierte benzoylderivate |
| US6165944A (en) * | 1997-01-17 | 2000-12-26 | Basf Aktiengesellschaft | 4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides |
| CN1141306C (zh) * | 1997-10-30 | 2004-03-10 | 日本曹达株式会社 | 新型苯甲酰基吡唑化合物、制备中间体和除草剂 |
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| CN103788083A (zh) * | 2014-03-10 | 2014-05-14 | 中国药科大学 | 一种制备除草剂苯唑草酮的方法 |
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| Publication number | Publication date |
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| EP1031573A1 (en) | 2000-08-30 |
| JPH11240872A (ja) | 1999-09-07 |
| US6147031A (en) | 2000-11-14 |
| BR9814832A (pt) | 2000-10-03 |
| EP1031573A4 (en) | 2001-08-29 |
| JP2009263395A (ja) | 2009-11-12 |
| WO1999023094A1 (fr) | 1999-05-14 |
| JP4441003B2 (ja) | 2010-03-31 |
| CN1278259A (zh) | 2000-12-27 |
| JP5102253B2 (ja) | 2012-12-19 |
| DE69839310T2 (de) | 2009-04-09 |
| DE69839310D1 (de) | 2008-05-08 |
| DE69839310T3 (de) | 2015-08-06 |
| AU9650598A (en) | 1999-05-24 |
| EP1031573B2 (en) | 2015-05-27 |
| EP1031573B1 (en) | 2008-03-26 |
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