CN1088063C - 磺酰氨基(硫代)羰基-1,2,4-三唑啉(硫)酮衍生物及制备方法和作为除草剂的应用 - Google Patents
磺酰氨基(硫代)羰基-1,2,4-三唑啉(硫)酮衍生物及制备方法和作为除草剂的应用 Download PDFInfo
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- CN1088063C CN1088063C CN96191629A CN96191629A CN1088063C CN 1088063 C CN1088063 C CN 1088063C CN 96191629 A CN96191629 A CN 96191629A CN 96191629 A CN96191629 A CN 96191629A CN 1088063 C CN1088063 C CN 1088063C
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- -1 Sulfamidyl (thio) carbonyl-1,2,4-triazolineone Chemical class 0.000 title claims abstract description 196
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 29
- 229940124530 sulfonamide Drugs 0.000 title description 3
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 39
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 27
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 96
- 239000000460 chlorine Substances 0.000 claims description 96
- 229910052801 chlorine Inorganic materials 0.000 claims description 96
- 229910052731 fluorine Inorganic materials 0.000 claims description 94
- 239000011737 fluorine Substances 0.000 claims description 94
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 55
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 55
- 229910052794 bromium Inorganic materials 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 241000196324 Embryophyta Species 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
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- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 5
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
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- 150000003818 basic metals Chemical group 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 16
- POPRCUFMXZJTQI-UHFFFAOYSA-N oxomethanedisulfonic acid Chemical compound OS(=O)(=O)C(=O)S(O)(=O)=O POPRCUFMXZJTQI-UHFFFAOYSA-N 0.000 claims 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 241000405414 Rehmannia Species 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 150000001913 cyanates Chemical class 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 5
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- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 4
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- 125000005110 aryl thio group Chemical group 0.000 abstract description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 abstract description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 2
- 125000006323 alkenyl amino group Chemical group 0.000 abstract 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 76
- 125000004093 cyano group Chemical group *C#N 0.000 description 30
- 239000002585 base Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- 239000003999 initiator Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229950001891 iprotiazem Drugs 0.000 description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 239000008096 xylene Substances 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
本发明涉及通式(I)的磺酰氨基(硫代)羰基三唑啉(硫)酮及式(I)化合物的盐,还涉及多种制备式(I)新化合物及其盐的方法和这些化合物作为除草剂的用途及其中Z是卤素,烷氧基,芳氧基或芳烷氧基的式(IV)化合物的中间体其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢、羟基、氨基、亚烷基氨基或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、烷氨基、二烷氨基、烷酰氨基、环烷基、环烷氨基、环烷基烷基、芳基和芳烷基,R2代表氢、羟基、巯基、氨基、卤素或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、炔氧基、烷硫基、烯硫基、炔硫基、烷氨基、烯氨基、炔氨基、二烷氨基、烷酰氨基、吖丙啶基、吡咯烷基、哌啶基、吗啉基、环烷基、环烯基、环烷氧基、环烷硫基、环烷氨基、环烷基烷基、环烷基烷氧基、环烷基烷硫基、环烷基烷氨基、芳基、芳烷基、芳氧基、芳基烷氧基、芳硫基、芳基烷硫基、芳氨基和芳基烷氨基,或者R1和R2一起代表可任选支化的链烷二基,R3代表可任选取代的芳基、芳烷基或杂芳基,条件是,Q1或Q2之一代表硫或者二者均为硫。
Description
本发明涉及含至少一个硫代羰基[-C(=S)-]的磺酰氨基(硫代)羰基三唑啉(硫)酮,它们的多种制备方法以及作为除草剂的应用。
已知某些磺酰氨基羰基三唑啉酮具有除草剂性能(参见EP-A341489,EP-A422469,EP-A425948,EP-A431291)。但是,带有至少一个硫代羰基的磺酰基氨基(硫代)羰基三唑啉(硫)酮至今尚未公开。
Q1代表氧或硫,
Q2代表氧或硫,
R1代表氢、羟基、氨基、亚烷基氨基或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、烷氨基、二烷氨基、烷酰氨基、环烷基、环烷氨基、环烷基烷基、芳基和芳烷基,
R2代表氢、羟基、巯基、氨基、卤素或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、炔氧基、烷硫基、烯硫基、炔硫基、烷氨基、烯氨基、炔氨基、二烷氨基、烷酰氨基、吖丙啶基、吡咯烷基、哌啶基、吗啉基、环烷基、环烯基、环烷氧基、环烷硫基、环烷氨基、环烷基烷基、环烷基烷氧基、环烷基烷硫基、环烷基烷氨基、芳基、芳烷基、芳氧基、芳基烷氧基、芳硫基、芳基烷硫基、芳氨基和芳基烷氨基,或者
R1和R2一起代表可任选支化的链烷二基,
R3代表均可被任选取代的芳基、芳烷基或杂芳基,
条件是,Q1或Q2中的一个代表硫或者二者均为硫。
通式(I)的新的磺酰氨基(硫代)羰基三唑啉(硫)酮按以下方式得到:
(a)通式(II)的三唑啉(硫)酮与通式(III)的磺酰基异(硫代)氰酸酯反应其中Q1、R1和R2各自定义如上,
R3-SO2-N=C=Q2 (III)其中Q2和R3各自定义如上,
如果合适,反应在有反应助剂和稀释剂存在下进行,或者
(b)通式(IV)的三唑啉(硫)酮衍生物与通式(V)的磺酰胺反应,其中Q1、Q2、R1和R2各自定义如上,Z代表卤素、烷氧基、芳氧基或芳基烷氧基,
R3-SO2-NH2 (V)其中R3的定义如上,
如果合适,反应在酸受体和稀释剂存在下进行,或者
R3-SO2-NH-CQ2-Z (VI)其中Q2和R3各自定义如上,Z代表卤素、烷氧基、芳氧基或芳基烷氧基,
如果合适,反应在酸受体或稀释剂存在下进行,或者
R3-SO2-X (VII)其中R3的定义如上,X代表卤素,
MQ2CN (VIII)其中Q2的定义如上,M代表碱金属或碱土金属等效物,
如果合适,反应在反应助剂和稀释剂存在下进行;
如果需要,按方法(a)、(b)、(c)或(d)得到的式(I)化合物可以用常见方法转化成盐。
通式(I)的新的磺酰氨基(硫代)羰基三唑啉(硫)酮是有强的除草作用。
本发明优选涉及这样的式(I)化合物,其中:
Q1代表氧或硫,
Q2代表氧或硫,
R1代表氢、羟基或氨基,或者代表C2-C10亚烷基氨基,或代表可任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷基羰基或C1-C4烷氧基羰基取代的C1-C6烷基,或代表均可任选地被氟、氯和/或溴取代的C2-C6链烯基或C2-C6炔基,或代表均可任选地被氟、氯、氰基、C1-C4烷氧基或C1-C4烷氧羰基取代的C1-C6烷氧基、C1-C6烷氨基或C1-C6烷酰氨基,或代表C3-C6烯氧基,或代表二(C1-C4烷基)氨基,或代表均可任选地被氟、氯、溴、氰基和/或C1-C4烷基取代的C3-C6环烷基、C3-C6环烷氨基或C3-C6环烷基-C1-C4烷基,或代表均可任选地被氟、氯、溴、氰基、硝基、C1-C4烷基、三氟甲基和/或C1-C4烷氧基取代的苯基或苯基-C1-C4烷基,
R2代表氢、羟基、巯基、氨基、氟、氯、溴或碘,或代表任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷基羰基或C1-C4烷氧羰基取代的C1-C6烷基,或代表均可任选地被氟、氯和/或溴取代的C2-C6链烯基或C2-C6炔基,或代表均可任选地被氟、氯、氰基、C1-C4烷氧基或C1-C4烷氧基羰基取代的C1-C6烷氧基、C1-C6烷硫基、C1-C6烷氨基或C1-C6烷酰氨基,或代表C3-C6烯氧基、C3-C6炔氧基、C3-C6烯硫基、C3-C6炔硫基、C3-C6烯氨基或C3-C6炔氨基,或代表二(C1-C4烷基)氨基,或代表均可任选被甲基和/或乙基取代的吖丙啶基、吡咯烷基、哌啶基或吗啉基,或代表均可被氟、氯、溴、氰基和/或C1-C4烷基取代的C3-C6环烷基、C5-C6环烯基、C3-C6环烷氧基、C3-C6环烷硫基、C3-C6环烷氨基、C3-C6环烷基C1-C4烷基、C3-C6环烷基C1-C4烷氧基、C3-C6环烷基-C1-C4烷硫基或C3-C6环烷基C1-C4烷氨基,或代表均可任选被氟、氯、溴、氰基、硝基、C1-C4烷基、三氟甲基和/或C1-C4烷氧基取代的苯基、苯基-C1-C4烷基、苯氧基、苯基-C1-C4烷氧基、苯硫基、苯基-C1-C4烷硫基、苯氨基或苯基-C1-C4烷氨基,或者
R1与R2一起代表可任选支化的3-11个碳原子的链烷二基,
R3代表以下基团其中R4和R5相同或不同,各自代表氢、氟、氯、溴、碘、硝基、C1-C6烷基(它可任选地被以下基团取代:氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基、C1-C4烷基羰氧基、C1-C4烷氧基羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、二(C1-C4烷基)氨基磺酰基、C3-C6环烷基或苯基),或代表C2-C6链烯基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或代表C2-C6炔基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或代表C1-C4烷氧基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧基羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或代表C1-C4烷硫基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或代表C2-C6烯氧基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),或代表C2-C6烯硫基(它可任选地被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基取代)、C3-C6炔氧基、C3-C6炔硫基,或代表基团-S(O)p-R6,其中
p代表数字1或2,和
R6代表C1-C4烷基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代)、C3-C6链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氨基、C1-C4烷氨基、二(C1-C4烷基)氨基或苯基,或代表基团-NHOR7,其中
R7代表C1-C12烷基(它可任选地被氟、氯、氰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基羰基、C1-C4烷氧羰基、C1-C4烷氨基羰基或二(C1-C4烷基)氨基羰基取代),或代表C3-C6链烯基(它可任选地被氟、氯或溴取代)、C3-C6炔基、C3-C6环烷基、C3-C6环烷基-C1-C2烷基或苯基-C1-C2烷基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧羰基取代),或代表二苯甲基或代表苯基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、三氟甲基、C1-C4烷氧基、C1-C2氟烷氧基、C1-C4烷硫基、三氟甲硫基或C1-C4烷氧羰基取代),
R4和R5还表示苯基或苯氧基,或者代表C1-C4烷基羰基氨基、C1-C4烷氧羰基氨基、C1-C4烷氨基羰基氨基或二(C1-C4烷基)氨基羰基氨基,或代表基团-CO-R8,其中
R8代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6环烷氧基、C3-C6烯氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基-C1-C4烷氨基或二(C1-C4烷基)氨基(它们均可任选地被氟和/或氯取代),
R4和/或R5还代表三甲硅烷基、噻唑啉基、C1-C4烷基磺酰氧基或二(C1-C4烷基)氨基磺酰氨基,或代表基团-CH=N-R9,其中
R9代表可任选被氟、氯、氰基、羧基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代的C1-C6烷基,或代表任选被氟或氯取代的苄基,或代表任选被氟或氯取代的C3-C6链烯基或C3-C6炔基,或代表任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基或三氟甲硫基取代的苯基,或代表可任选被氟和/或氯取代的C1-C6烷氧基、C3-C6烯氧基、C3-C6炔氧基或苄氧基,或代表氨基、C1-C4烷氨基、二(C1-C4烷基)氨基、苯氨基、C1-C4烷基羰基氨基、C1-C4烷氧羰基氨基或C1-C4烷基磺酰氨基,或代表可任选被氟、氯、溴或甲基取代的苯基磺酰氨基,
或者,
R11和R12相同或不同,各代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、羧基、C1-C4烷氧羰基、二甲氨基羰基、C1-C4烷基磺酰基或二(C1-C4烷基)氨基磺酰基;
或者,
或者,
R3代表以下基团其中R15和R16相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或代表C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代),或代表氨基磺酰基或一(C1-C4烷基)氨基磺酰基,或代表二(C1-C4烷基)氨基磺酰基或C1-C4烷氧羰基或二甲氨基羰基;
或者,
R3代表以下基团其中R17和R18相同或不同,各自代表氢、氟、氯、溴、C1-C4烷基(它可任选地被氟和/或溴取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或代表C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代),或代表二(C1-C4烷基)氨基磺酰基;
或者,
R3代表以下基团其中R19和R20相同或不同,各自代表氢、氟、氯、溴、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代)、二(C1-C4烷基)氨基磺酰基、C1-C4烷氧羰基或二甲氨基羰基,
A代表氧、硫或基团N-Z1,其中
Z1代表氢、C1-C4烷基(它可任选地被氟、氯、溴或氰基取代)、C3-C6环烷基、苄基、苯基(它可任选地被氟、氯、溴或硝基取代)、C1-C4烷基羰基、C1-C4烷氧羰基或二(C1-C4烷基)氨基羰基;
或者,
R3代表以下基团其中R21和R22相同或不同,各自代表氢、C1-C4烷基、卤素、C1-C4烷氧羰基、C1-C4烷氧基或C1-C4卤代烷氧基,
Y1代表硫或基团N-R23,其中
R23代表氢或C1-C4烷基;
或者,
R25代表氢、卤素、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、二氧戊环基或C1-C4烷氧羰基,
R26代表氢、卤素或C1-C4烷基;
或者,
本发明更优选地涉及式(I)化合物的钠、钾、镁、钙、铵、C1-C4烷基铵、二(C1-C4烷基)铵、三(C1-C4烷基)铵、四(C1-C4烷基)铵、三(C1-C4烷基)锍、C5或C6环烷基铵和二(C1-C2烷基)苄基铵盐,其中Q1、Q2、R1、R2和R3优选定义如上。
本发明特别涉及这样的式(I)化合物,其中
Q1代表氧或硫,
Q2代表氧或硫,
R1代表氢、羟基或氨基,或代表C3-C8亚烷基氨基或代表均可被氟、氯、氰基、甲氧基或乙氧基任选取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表均可被氟、氯或溴任选取代的丙烯基、丁烯基、丙炔基或丁炔基,或代表均可任选地被氟、氯、氰基、甲氧基或乙氧基取代的甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲氨基、乙氨基、正或异丙氨基、正、异、仲或叔丁氨基、或代表丙烯氧基或丁烯氧基,或代表二甲氨基或二乙氨基,或代表均可任选地被氟、氯、甲基和/或乙基取代的环丙基、环丁基、环戊基、环己基、环丙氨基、环丁氨基、环戊氨基、环己氨基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,或代表均可任选地被氟、氯、甲基、三氟甲基和/或甲氧基取代的苯基或苄基,
R2代表氢、羟基、巯基、氨基、氟、氯或溴,或代表均可任选地被氟、氯、氰基、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表均可任选地被氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或代表均可任选地被氟、氯、溴、氰基、甲氧基或乙氧基取代的甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、甲硫基、乙硫基、正或异丙硫基、正、异、仲或叔丁硫基、甲氨基、乙氨基、正或异丙氨基、正、异、仲或叔丁氨基,或代表丙烯氧基、丁烯氧基、丙炔氧基、丁炔氧基、丙烯硫基、丁烯硫基、丙炔硫基、丁炔硫基、丙烯氨基、丁烯氨基、丙炔氨基或丁炔氨基,或代表二甲氨基、二乙氨基或二丙氨基,或代表均可任选地被氟、氯、甲基和/或乙基取代的环丙基、环丁基、环戊基、环己基、环戊烯基、环己烯基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙氨基、环丁氨基、环戊氨基、环己氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲氨基、环丁基甲氨基、环戊基甲氨基或环己基甲氨基,或代表均可任选地被氟、氯、甲基、三氟甲基和/或甲氧基取代的苯基、苄基、苯氧基、苄氧基、苯硫基、苄硫基、苯氨基或苄氨基,或者
R1和R2一起代表有3-11个碳原子的任选支化的链烷二基,同时
R3代表基团其中R4代表氟、氯或溴,或代表均可任选地被氟和/或氯取代的甲基、乙基、正或异丙基,或代表均可任选地被氟、氯、甲氧基或乙氧基取代的甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、N-甲氧基-N-甲氨基磺酰基、甲氧氨基磺酰基、苯基或苯氧基,或代表均可任选地被氟、氯、甲氧基或乙氧基取代的甲氧羰基、乙氧羰基、正或异丙氧羰基,和
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R3代表以下基团其中R10代表氢,
R11代表氟、氯、溴、甲基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基、乙氧基、甲氧羰基、乙氧羰基、甲基磺酰基或二甲氨基磺酰基,
R12代表氢;
或者,
R3代表以下基团其中R代表甲基、乙基、正或异丙基,
或者,
R25代表氢、氟、氯或溴,
R26代表氟、氯、溴、甲氧羰基或乙氧羰基;
条件是,Q1或Q2中的一个代表硫,或者二者均代表硫。
以上列出的基团定义,不管是一般定义或是优选范围内的定义,都不仅适用于式(I)的最终产物,而且也相应地适用于在各处制备中所要求的起始物和/或中间体。这些基团定义可以根据需要彼此结合,从而包括在所示优选范围之间的组合。
在这些基团的定义中,诸如烷基、链烯基或炔基等烃基,即使在与杂原子的组合中,例如在烷氧基、烷硫基或烷氨基中,均可是直链的或支链的,虽然这并未明确说明。
卤素一般代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
本发明式(I)化合物中基团R1、R2和R3的含意的实例分成以下几组列出。第一组
R1具有例如以下列出的含意:
氨基,正或异亚丙基氨基,甲基,乙基,正或异丙基,正、异、仲或叔丁基,二氯丙基,二溴丙基,甲氧基丙基,丙烯基,丁烯基,丙炔基,丁炔基,甲氧基,乙氧基,正或异丙氧基,甲氨基,乙氨基,正或异丙氨基,丙烯氧基,二甲氨基,环丙基,环丁基,环戊基,环己基,甲基环丙基或环丙基甲基。
R2具有例如以下列出的含意:
氢,氯,溴,甲基,乙基,正或异丙基,正、异、仲或叔丁基,三氟甲基,甲氧甲基,乙氧甲基,丙烯基,丁烯基,丙炔基,丁炔基,甲氧基,乙氧基,正或异丙氧基,正、异、仲或叔丁氧基,甲硫基,乙硫基,正或异丙硫基,正、异、仲或叔丁硫基,氟甲硫基,氯甲硫基,氟乙硫基,氯乙硫基,二氟乙硫基,三氟乙硫基,三氟丙硫基,甲氨基,乙氨基,正或异丙氨基,正、异、仲或丁氨基,丙烯氧基,丁烯氧基,丙炔氧基,丁炔氧基,丙烯硫基,丁烯硫基,丙烯氨基,丁烯氨基,丙炔氨基,丁炔氨基,二甲氨基,二乙氨基,N-甲基乙氨基,N-甲基丙氨基,N-乙基丙氨基,环丙基,环丙氧基,环丙氨基,环丙基甲基,环丙基甲氧基,环丙基甲硫基,苯基,苯氧基,苯硫基,苯氨基,苯甲基,苯基甲氧基,苯基甲硫基或苯基甲氨基。
另外,R1和R2一起具有例如以下的含意:
丙-1,3-二基,丁-1,4-二基,戊-1,5-二基,己-1,6-二基,庚-1,7-二基和十一烷-1,11-二基。
R3具有例如以下列出的含意:
2-氟苯基,2-氯苯基,2-溴苯基,2,6-二氟苯基,2,6-二氯苯基,2-甲基苯基,2-氯-6-甲基苯基,2-三氟甲基苯基,2-(2-氟乙基)苯基,2-(2-氯乙基)苯基,2-(3-氟丙基)苯基,2-(3-氯丙基)苯基,2-(3,3,3-三氟丙基)苯基,2-(3,3,3-三氟-1-丙烯基)苯基,2-甲氧基苯基,2-乙氧基苯基,2-二氟甲氧基苯基,2-三氟甲氧基苯基,2-(2-氟乙氧基)苯基,2-(2-氯乙氧基)苯基,2-(2-甲氧乙氧基)苯基,2-甲硫基苯基,2-乙硫基苯基,2-甲基亚磺酰苯基,2-乙基亚磺酰苯基,2-甲磺酰苯基,2-乙磺酰苯基,2-二甲氨基磺酰苯基,2-苯基苯基,2-甲氧羰基苯基,2-乙氧羰基苯基,2-氯苯基甲基,2,6-二氯苯基甲基,2-二氟甲氧基苯基甲基,2-三氟甲氧基苯基甲基,2-甲氧羰基苯基甲基,2-乙氧羰基苯基甲基,2-甲氧羰基-3-噻吩基,2-乙氧羰基-3-噻吩基,4-甲氧羰基-1-甲基-5-吡唑基,4-乙氧羰基-1-甲基-5-吡唑基,3-氯-4-甲氧羰基-1-甲基-5-吡唑基,3-氯-4-乙氧羰基-1-甲基-5-吡唑基,3-甲氧羰基-2-吡啶基,3-乙氧羰基-2-吡啶基,3-二甲氨基羰基-2-吡啶基,3-甲磺酰-2-吡啶基或3-乙磺酰-2-吡啶基。第二组
R1、R2和R3具有上面在第1组中式(IA)下列出的含意。第三组
R1、R2和R3具有上面在第1组中式(IA)下列出的含意。
使用例如2,6-二氟苯基异氰酸酯和5-乙基-4-甲氧基-2,4-二氢-3H-1,2,4-三唑-3-硫酮作为起始物,本发明方法(a)的反应过程可以用以下反应式说明:
使用例如N-甲氧基硫代羰基-2-甲氧基苯磺酰胺和5-乙氧基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮作为起始物,本发明方法(c)的反应过程可用以下反应式说明:
在根据本发明制备式(I)化合物的方法(a)、(c)和(d)中作为起始物使用的三唑啉(硫)酮的一般定义由式(II)给出。
在式(II)中,Q1、R1和R2优选或特别是具有上面与本发明式(I)化合物的描述相关的作为优选或特别优选的Q1、R1和R2已经指出的那些含意。
通式(II)的三唑啉(硫)酮是已知化合物和/或可以用本身已知的方法制备(参见:药物文献(Arch.Pharm.)301(1968),827;同上文献307(1974),889;法国化学学会通报(Bull.Soc.Chin.France)1962,1365;同上文献,1975,1191;化学报告(Chem.Ber.)90(1957)909-921;同上文献98(1965),3025-3099;同上文献102(1969),755;杂环化学杂志(J.Heterocycl.Chem.)15(1978),237-240;印度化学会志(J.Indian Chem.soc.)6(1929),565;李比希化学记事(Liebigs Ann.Chem.)637(1960),135;化学及其它有关科学月刊(Monatshefte Chemie)123(1992),257;四面体(Tetrahedron)32(1976),2347-2352;瑞士化学学报(Helv.Chem.Acta)63(1980),841-859;英国化学会志C辑(J.Chem.Soc.C)1967,746-751;同上文献,1970,26-34;英国化学会志Perkin汇刊I(J.Chem.soc.Perkin I)1973,2644;土耳其Ege大学科学学院杂志(Fen Fak.Derg.,Seri A(Ege Univ.))7(1984),1-6,引自化学文摘CA101:90846m;EP-A283876;EP-A294666;EP-A298371;EP-A301946;EP-A305844;EP-A341489;EP-A362633;EP-A370293;EP-A391187;EP-A398096;EP-A398097;EP-A399294;EP-A415196;EP-A422469;EP-A425948;EP-A431291;EP-A477646;EP-A502307;EP-A503437;EP-A505819;EP-A511569;EP-A513621;DE-A2336827;DE-A3839206;DE-A3916208;DE-A3916930;DD-P64970;WO-A93/04050;制备实施例)。
在本发明制备式(I)化合物的方法(a)中也作为起始物使用的磺酰基异(硫)氰酸酯的一般定义由式(III)给出。
在式(III)中,Q2和R3各自优选或特别是具有上面与本发明式(I)化合物的描述相关的作为优选或特别优选的Q2和R3已经指出的那些含意。
式(III)起始物是已知的,和/或者可以用本身已知的方法制备(参见US-P4127405,US-P4169719,US-P4371391,EP-A7687,EP-A13480,EP-A21641,EP-A23141,EP-A23422,EP-A30139,EP-A35893,EP-A44808,EP-A44809,EP-A48143,EP-A51466,EP-A64322,EP-A70041,EP-A173312)。
在本发明制备通式(I)化合物的方法(b)中作为起始物使用的三唑啉(硫)酮衍生物的一般定义由式(IV)给出。在式(IV)中,Q1、Q2、R1和R2各自优选或特别具有此前与式(I)化合物的描述相关的作为优选或特别优选的Q1、Q2、R1和R2已经提出的那些含意;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基、苯氧基、卤代基或硝基苯氧基,特别是代表甲氧基、苯氧基或4-硝基苯氧基。
式(IV)的起始物文献中尚未报道;作为新物质,它们也是本申请的主题的一部分。通式(IV)新化合物的制备方法是,使通式(II)的三唑(硫)酮与通式(IX)的(硫代)碳酸衍生物反应其中Q1、R1和R2各自定义如上,
Z-CQ2-Z1 (IX)其中Z和Q2各自定义如上,Z1代表卤素、烷氧基、芳烷氧基或芳氧基,
如果合适,反应在酸受体(例如氢氧化钠或氢氧化钾、叔丁醇钠或叔丁醇钾)和稀释剂(例如二氯甲烷、四氢呋喃或二甲氧基乙烷和/或水)存在下于0-100℃的温度下进行。
在本发明制备式(I)化合物的方法(b)中也作为起始物使用的磺酰胺的一般定义由式(V)给出。在式(V)中,R3优选或者特别是具有上面与式(I)化合物的描述相关的作为优选或特别优选的R3已经指出的那些含意。
式(V)起始物是已知的和/或可以用本身已知的方法制备(参见
US-P4127405,US-P4169719,US-P4371391,EP-A7687,EP-A13480,EP-A21641,EP-A23141,EP-A23422,EP-A30139,EP-A35893,EP-A44808,EP-A44809,EP-A48143,EP-A51466,EP-A64322,EP-A70041,EP-A173312)。
在本发明制备通式(I)化合物的方法(c)中作为起始物使用的磺酰胺衍生物的一般定义由式(VI)给出。在式(VI)中,Q2和R3各自优选或者特别具有上面与式(I)化合物的描述相关的作为优选或特别优选的Q2和R3已经指出的那些含意;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基或苯氧基,特别是代表甲氧基或苯氧基。
式(VI)起始物是已知的和/或可以用本身已知的方法制备。
在本发明制备式(I)化合物的方法(d)中作为起始物使用的磺酰卤的一般定义由式(VII)给出。在式(VII)中,R3优选或特别具有上面与式(I)化合物的描述相关的作为优选或特别优选的R3已经指出的那些含意;X优选代表氟、氯或溴,特别是代表氯。
式(VII)的起始物是已知的和/或可以用本身已知的方法制备。
本发明制备式(I)新化合物的方法(a)、(b)、(c)和(d)优选用稀释剂进行。这方面合适的稀释剂是基本上所有的惰性有机溶剂。这些溶剂优选包括可任选卤化的脂族和芳族烃类,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯甲烷、氯苯和间二氯苯;醚类,例如乙醚和二丁醚、乙二醇二甲醚和二乙二醇二甲醚、四氢呋喃和二噁烷;酮类,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮;酯类;例如乙酸甲酯和乙酸乙酯;腈类,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,还包括二甲基亚砜,四亚甲基砜和六甲基磷酸三酰胺。
作为在本发明方法(a)、(b)、(c)和(d)中的反应助剂和/或酸受体,可以使用通常能用于这类反应的任何酸结合剂。优选使用碱金属氢氧化物,例如氢氧化钠和氢氧化钾;碱土金属氢氧化物,例如氢氧化钙;碱金属碳酸盐和醇盐,例如碳酸钠和碳酸钾,叔丁醇钠和叔丁醇钾;以及碱性氮化合物,例如三甲胺、三乙胺、三丙胺、三丁胺、二异丁胺、二环己烷、乙基二异丙胺、乙基二环己胺、N,N-二甲基苄胺、N,N-二甲基苯胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基-吡啶,1,5-二氮杂双环[4.3.0]壬-5-烯(DBN),1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)和1,4-二氮杂双环[2.2.2]辛烷(DABCO)。
本发明方法(a)、(b)、(c)和(d)中的反应温度可以在相对较宽的范围内变化。反应一般在-20℃至+150℃的温度范围内进行,优选在0℃至+100℃之间进行。
本发明方法(a)、(b)、(c)和(d)通常在大气压下进行。但是它也可以在升压或减压下操作。
为进行本发明方法(a)、(b)、(c)和(d),每种情形里所需的起始物一般以近似等摩尔量使用。但是也可以使在各个情形中使用的组分之一有较大的过剩。反应通常在合适的稀释剂中于酸受体存在下进行,在所要求的特定温度下将反应混合物搅拌几小时。在本发明方法(a)、(b)、(c)和(d)中,后处理均按常用方法进行(参见制备实施例)。
本发明通式(I)化合物的盐可以根据需要制备。这类盐是以简单的方式用常用的成盐方法得到,例如将式(I)化合物溶解或分散在适当的溶剂中,例如二氯甲烷、丙酮、叔丁基甲基醚或甲苯中,并加入合适的碱。盐可以随后(如果需要,在长期搅拌之后)用浓缩或抽气过滤的方法分离。
本发明活性化合物可以作为落叶剂、干燥剂、杀基杆剂,尤其是作为除杂草剂使用。所谓杂草,在最广泛的意义上应理解为生长在不应生长的地区的所有植物。本发明物质是作为灭生除草剂还是作为选择性除草剂起作用,主要取决于所用的数量。
本发明活性化合物可用于例如以下植物:
以下各属双子叶杂草:欧白芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,焊菜属,节节菜属,母草属,野芝麻属,婆婆纳属,苘麻属,刺酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,三叶草属,毛茛属和蒲公英属。
以下各属双子叶栽培作用: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,花生属,芸苔属,莴苣属,香瓜属和南瓜属。
以下各属单子叶杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,高粱属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,藨草属,雀稗属,鸭嘴草属,尖瓣花属,龙爪茅属,剪股颖属,看麦娘属和风草属。
以下各属单子叶栽培作用:稻属,壬蜀黍属,小麦属,大麦属,燕麦属,黑麦属,高粱属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
然而,本发明活性化合物的用途绝对不仅限于以上各属,而是以同样的方式也扩展到其它植物。
因浓度而异,这类化合物适合于诸如工业场地和铁路线上以及有或无树林的道路和广场上作灭生性除草。同样,这类化合物也可用于多年生栽培植物如造林带、装饰性园林、果园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶场、橡胶园、油棕园、可可园、浆果园和啤酒花田除草,草坪、草地和牧场除草,以及一年生栽培植物的选择性除草。
本发明式(I)化合物优选适合于单子叶和双子叶栽培作用中选择性去除单子叶和双子叶杂草,可以是苗前或是苗后。
活性化合物可以转化成常用的制剂,例如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、糊剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然与合成物质,以及在聚合物中的很细小的胶囊。
这些制剂用已知方法制成,例如可通过下述方法,任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物与填充量剂(即液体溶剂和/或固体载体)混合。
如果采用水作为填充剂,则也可以用例如有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘),氯化芳族化合物和氯化脂族烃类(如氯苯、氯乙烯或二氯乙烯),脂族烃类(如环己烷或链烷烃,例如石油馏分),矿物和植物油,醇类(如丁醇或乙二醇以及它们的醚和酯),酮类(如丙酮、甲乙酮、甲基异丁基酮或环己酮),强极性溶剂(如二甲基甲酰胺和二甲基亚砜,以及水)。
合适的固体载体有:如铵盐和磨碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、硅镁土、蒙脱土或硅藻土)及磨碎的合成矿物(如高度分散的二氧化硅、氧化铝和硅酸盐);适合颗粒剂的固体载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及无机合成颗粒和有机粉的合成颗粒以及有机材料(如锯末、椰壳、玉米芯和烟草杆)的颗粒;适用的乳化剂和/或起泡剂有: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(如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物;合适的分散剂有:木素亚硫酸废液和甲基纤维素。
在制剂中可以使用粘合剂,例如羧甲基纤维素和粉末、颗粒或胶乳形式的天然及合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其它添加剂可以是矿物和植物油。
可以使用着色剂,例如无机颜料(如氧化铁、二氧化钛和普鲁士兰)和有机染料(如茜素染料、偶氮染料和金属酞菁染料),以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1-95%重量的活性化合物,最好是0.5-90%。
为防治杂草,本发明的活性化合物本身或其制剂形式,也可以与已知的除草剂、配好备用的制剂或桶混物一起以混合物的形式使用。
可用于混合物中的组分是已知的除草剂,例如N-酰苯胺类,如吡氟草胺和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸,如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和定草酯;芳氧苯氧基链烷酸酯,如禾草灵、噁唑禾草灵、吡氯禾草灵、吡氟禾草灵和喹禾灵;连氮酮类,如杀草敏和达草灭;氨基甲酸酯类,如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;乙酰氯苯胺类,如甲草胺、乙草安、丁草胺、吡草胺、异丙甲草安、丙草胺和毒草安;二硝基苯胺类,如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类,如三氟羧草醚、甲羧除草醚、乙羧除草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类,如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆;羟胺类,如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类,如咪草烟、咪草酯、灭草烟和灭草喹;腈类,如溴苯腈、敌草腈和碘草腈;氧乙酰胺类,如苯噻草胺;磺酰脲类,如amidosulfuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类,如阿特拉津、草净津、西玛津、西草净、去草净和特丁津;三嗪酮类,如环嗪酮、苯嗪草酮和嗪草酮;其它,例如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵磷、草甘膦、isoxaben、哒草灭、二氯喹啉酸、喹草酸、草硫膦和灭草环。
也可以与已知的其它活性化合物混合,例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂和改进土壤结构的试剂。
活性化合物可以照原样,以制剂形式或者以通过进一步稀释形式的使用形式(例如配好备用的溶液、悬浮液、乳液、粉末、糊和颗粒)使用。它们可以按常用方式使用,例如浇灌、喷雾、弥雾或撒布。
本发明化合物可以在植物出苗之前或之后施用。它们也可以在播种前掺加到土壤中。
活性化合物的用量可以在相当大的范围内变化。这主要取决于所要求的效果。一般来说,用量为每公顷地表面用1g-10kg活性化合物,优选每公顷10g-5kg。
由以下实施例可以看到本发明活性化合物的制备及用途。制备实施例
将3.0g(20.7mmol)4-甲基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮、4.8g(20.7mmol)3-氯苯基磺酰基异硫氰酸酯、0.3g三乙胺和60ml乙腈的混合物回流加热12小时,然后用水泵抽气浓缩。残余物与乙醚一起搅拌,抽气过滤分离出结晶产物。
得到2.1g(理论值的27%)2-(3-氯苯磺酰氨基硫代羰基)-4-甲基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点141℃。
将3.2g(12mmol)5-甲氧基-4-甲基-2-苯氧基硫羰基-2,4-二氢-3H-1,2,4-三唑-3-酮、2.9g(12mmol)2-三氟甲氧基苯磺酰胺、1.9g(12.5mmol)1,8-二氮杂二环[5.4.0]十一碳-7-烯(DBU)和30ml二噁烷的混合物在20℃下搅拌12小时。然后用二氯甲烷和水稀释该混合物,用2N盐酸将pH调节到3。分离出有机相,用Na2SO4干燥,过滤。将滤液用水泵抽气浓缩,残余物用乙醚消化结晶,抽气过滤分离出产物。
在20℃下将28.1g(0.125mol)2-三氟甲基苯磺酰胺和19g 1,8-二氮杂二环[5.4.0]十一碳-7-烯(DBU)在50ml乙腈中的溶液依次加入到28.1g(0.10mol)4-甲基-5-甲硫基-2-苯氧硫羰基-2,4-二氢-3H-1,2,4-三唑-3-酮在300ml乙腈中的溶液里。将反应混合物在20℃下搅拌,直到形成透明的溶液。然后用水泵抽气将溶液浓缩,残余物与水和二氯甲烷混合(各300ml),用2N盐酸酸化。分离出有机层,水相用100ml二氯甲烷萃取一次,合并的有机相用硫酸镁干燥,过滤。将滤液用水泵抽气浓缩,残余物自异丙醇中结晶。
得到29.6g(理论值的72%)4-甲基-5-甲硫基-2-(2-三氟甲基苯磺酰氨基硫羰基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点154℃。
表1:(续)
表1:(续)
表1:(续)
表1:(续)
表1:(续)
将4.0g(20mmol)4-乙氧基-5-巯基-2,4-二氢-3H-1,2,4-三唑-3-酮的钾盐,4.3g(30mmol)甲基碘和50m1甲醇的混合物在20℃下搅拌16小时,然后浓缩。残余物用二氯甲烷/水萃取,分离出有机相,用硫酸镁干燥,过滤。将滤液浓缩,残余物用乙醚消化,抽气过滤分离出结晶产物。
得到1.8g(理论值的51%6+1)4-乙氧基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点99℃。
利用实施例(II-1)的方法和/或其它已知方法(参见上述出版物),可以制备出例如以下式(II)化合物:
4-甲基-,4,5-二甲基-,4-甲基-5-乙基-,4-甲基-5-正丙基-,4-甲基-5-异丙基-,4-甲基-5-正丁基-,4-甲基-5-苯氧基-,4-甲基-5-甲硫基-,4-甲基-5-乙硫基-,4-甲基-5-正丙硫基-,4-甲基-5-异丙硫基-,4-甲基-5-烯丙硫基-,4-甲基-5-炔丙硫基-,4-甲基-5-环丙基-,4-甲基-5-氯-,4-甲基-5-溴-,4-甲基-5-甲氧基-,4-甲基-5-乙氧基-,4-甲基-5-正丙氧基-,4-甲基-5-异丙氧基-,4-甲基-5-正丁氧基-,4-甲基-5-环丙基甲氧基-,4-甲基-5-环丙硫基-,4-甲基-5-三氟乙氧基-,4-甲基-5-二甲氨基-和4-甲基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-硫酮;
4-乙基-,4,5-二乙基-,4-乙基-5-甲基-,4-乙基-5-正丙基-,4-乙基-5-异丙基-,4-乙基-5-正丁基-,4-乙基-5-苯氧基-,4-乙基-5-甲硫基-,4-乙基-5-乙硫基-,4-乙基-5-正丙硫基-,4-乙基-5-异丙硫基-,4-乙基-5-烯丙硫基-,4-乙基-5-炔丙硫基-,4-乙基-5-环丙基-,4-乙基-5-氯-,4-乙基-5-溴,4-乙基-5-甲氧基-,4-乙基-5-乙氧基-,4-乙基-5-正丙氧基-,4-乙基-5-异丙氧基-,4-乙基-5-正丁氧基-,4-乙基-5-环丙基甲氧基-,4-乙基-5-环丙硫基-,4-乙基-5-三氟乙氧基-,4-乙基-5-二甲氨基-和4-乙基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-酮;
4-环丙基-5-甲基-,4-环丙基-5-乙基-,4-环丙基-5-正丙基-,4-环丙基-5-异丙基-,4-环丙基-5-正丁基-,4-环丙基-5-苯氧基-,4-环丙基-5-甲硫基-,4-环丙基-5-乙硫基-,4-环丙基-5-正丙硫基-,4-环丙基-5-异丙硫基-,4-环丙基-5-烯丙硫基-,4-环丙基-5-炔丙硫基-,4-环丙基-5-环丙基-,4-环丙基-5-氯-,4-环丙基-5-溴-,4-环丙基-5-甲氧基-,4-环丙基-5-乙氧基-,4-环丙基-5-正丙氧基-,4-环丙基-5-异丙氧基-,4-环丙基-5-正丁氧基-,4-环丙基-5-环丙基甲氧基-,4-环丙基-5-环丙硫基-,4-环丙基-5-三氟乙氧基-,4-环丙基-5-二甲氨基-和4-环丙基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-硫酮;
4-甲氧基-,4,5-二甲氧基-,4-甲氧基-5-甲基-,4-甲氧基-5-乙基-,4-甲氧基-5-正丙基-,4-甲氧基-5-异丙基-,4-甲氧基-5-正丁基,4-甲氧基-5-苯氧基,4-甲氧基-5-甲硫基-,4-甲氧基-5-乙硫基-,4-甲氧基-5-正丙硫基-,4-甲氧基-5-异丙硫基-,4-甲氧基-5-烯丙硫基-,4-甲氧基-5-炔丙硫基-,4-甲氧基-5-环丙基-,4-甲氧基-5-氯-,4-甲氧基-5-溴-,4-甲氧基-5-乙氧基-,4-甲氧基-5-正丙氧基-,4-甲氧基-5-异丙氧基-,4-甲氧基-5-正丁氧基-,4-甲氧基-5-环丙基甲氧基-,4-甲氧基-5-环丙硫基-,4-甲氧基-5-三氟乙氧基-,4-甲氧基-5-二甲氨基-和4-甲氧基-5-甲氨基-2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-硫酮;
4-乙氧基-,4,5-二乙氧基-,4-乙氧基-5-甲基-,4-乙氧基-5-乙基-,4-乙氧基-5-正丙基-,4-乙氧基-5-异丙基-,4-乙氧基-5-正丁基-,4-乙氧基-5-苯氧基-,4-乙氧基-5-甲硫基-,4-乙氧基-5-乙硫基-,4-乙氧基-5-正丙硫基-,4-乙氧基-5-异丙硫基-,4-乙氧基-5-烯丙硫基-,4-乙氧基-5-炔丙硫基-,4-乙氧基-5-环丙基-,4-乙氧基-5-氯-,4-乙氧基-5-溴-,4-乙氧基-5-甲氧基-,4-乙氧基-5-正丙氧基-,4-乙氧基-5-异丙氧基-,4-乙氧基-5-正丁氧基,4-乙氧基-5-环丙基甲氧基-,4-乙氧基-5-环丙硫基-,4-乙氧基-5-三氟乙氧基-,4-乙氧基-5-二甲氨基-和4-乙氧基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-酮;
4-氨基-,4-氨基-5-甲基-,4-氨基-5-乙基-,4-氨基-5-正丙基-,4-氨基-5-异丙基-,4-氨基-5-正丁基-,4-氨基-5-苯氧基-,4-氨基-5-甲硫基-,4-氨基-5-乙硫基-,4-氨基-5-正丙硫基-,4-氨基-5-异丙硫基-,4-氨基-5-烯丙硫基-,4-氨基-5-炔丙硫基-,4-氨基-5-环丙基-,4-氨基-5-氯-,4-氨基-5-溴-,4-氨基-5-甲氧基-,4-氨基-5-乙氧基-,4-氨基-5-正丙氧基-,4-氨基-5-异丙氧基-,4-氨基-5-正丁氧基-,4-氨基-5-环丙基甲氧基-,4-氨基-5-环丙硫基-,4-氨基-5-三氟乙氧基-,4-氨基-5-二甲氨基-和4-氨基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-硫酮;
4-甲氨基-,4-甲氨基-5-甲基-,4-甲氨基-5-乙基-,4-甲氨基-5-正丙基-,4-甲氨基-5-异丙基-,4-甲氨基-5-正丁基,4-甲氨基-5-苯氧基-,4-甲氨基-5-甲硫基-,4-甲氨基-5-乙硫基-,4-甲氨基-5-正丙硫基-,4-甲氨基-5-异丙硫基-,4-甲氨基-5-烯丙硫基-,4-甲氨基-5-炔丙硫基-,4-甲氨基-5-环丙基-,4-甲氨基-5-氯-,4-甲氨基-5-溴-,4-甲氨基-5-甲氧基-,4-甲氨基-5-乙氧基-,4-甲氨基-5-正丙氧基-,4-甲氨基-5-异丙氧基-,4-甲氨基-5-正丁氧基-,4-甲氨基-5-环丙基甲氧基-,4-甲氨基-5-环丙硫基-,4-甲氨基-5-三氟乙氧基-,4-甲氨基-5-二甲氨基-和4-甲氨基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和-2,4-二氢-3H-1,2,4-三唑-3-硫酮;
4-二甲氨基- 4-二甲氨基-5-甲基-,4-二甲氨基-5-乙基-,4-二甲氨基-5-正丙基-,4-二甲氨基-5-异丙基-,4-二甲氨基-5-正丁基-,4-二甲氨基-5-苯氧基-,4-二甲氨基-5-甲硫基-,4-二甲氨基-5-乙硫基-,4-二甲氨基-5-正丙硫基-,4-二甲氨基-5-异丙硫基-,4-二甲氨基-5-烯丙硫基-,4-二甲氨基-5-炔丙硫基-,4-二甲氨基-5-环丙基-,4-二甲氨基-5-氯-,4-二甲氨基-5-溴-,4-二甲氨基-5-甲氧基-,4-二甲氨基-5-乙氧基-,4-二甲氨基-5-丙氧基-,4-二甲氨基-5-异丙氧基-,4-二甲氨基-5-正丁氧基-,4-二甲氨基-5-环丙基甲氧基-,4-二甲氨基-5-环丙硫基-,4-二甲氨基-5-三氟乙氧基-,4-二甲氨基-5-二甲氨基-和4-二甲氨基-5-甲氨基- -2,4-二氢-3H-1,2,4-三唑-3-酮和2,4-二氢-3H-1,2,4-三唑-3-硫酮。式(IV)起始物:
实施例(IV-1)
在20℃下将15.0g(103mmol)4-甲基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮在120ml二氯甲烷中的溶液与4.6g氢氧化钠和0.5g溴化四丁铵在120ml水中的溶液混合。然后在20℃下向此混合物中逐滴加入19.6g(114mmol)O-苯基氯硫代甲酸酯在100ml二氯甲烷中的溶液,将此反应混合物在20℃下再搅拌12小时。抽气过滤,分离出结晶产物。
得到25.6g(理论值的88%)4-甲基-5-甲硫基-2-苯氧硫羰基-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点242℃。
在20℃下将29.6g(206mmol)4-甲基-5-乙氧基-2,4-二氢-3H-1,2,4-三唑-3-酮在240ml二氯甲烷中的溶液与9.2g氢氧化钾和1g溴化四丁铵在240ml水中的溶液混合。然后在20℃向此混合物中逐滴加入39.2g(228mmol)O-苯基氯硫代甲酸酯在200ml二氯甲烷中的溶液,将此反应混合物在20℃下再搅拌12小时。分离出有机相,水相用100ml二氯甲烷再萃取一次。合并的有机相用200ml水洗,用硫酸镁干燥,过滤。将滤液用水泵抽气浓缩,残余物与乙醚一起搅拌,抽气过滤,分离出结晶产物。
得到44.3g(理论值的77%)4-甲基-5-乙氧基-2-苯氧硫羰基-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点123℃。
表2:(续)应用实施例:
实施例A苗前试验
溶剂:5重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,浓缩物用水稀释至所要的浓度。
将试验植物的种子播种在普通土壤中。24小时后,用活性化合物制剂浇灌土壤。最好是保持每单位面积的水量恒定。制剂中活性化合物的浓度并不重要,起决定作用的只是每单位面积上施加的活性化合物数量。
三周后,与未处理对照的发育情况作比较,将植物的损伤程度按损伤%分级。
数字表示:
0%=无作用(与未处理对照相同)
100%=完全破坏
溶剂:5重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水将浓缩物稀释至所要的浓度。
将高度为5-15cm的试验植物用活性化合物制剂喷雾,以便在每单位面积上施用特定数量的所需活性化合物。选择喷雾液的浓度,使得特定数量的所需活性化合物以每公顷1000升水的方式使用。
三周后,与未处理的对照的发育情况比较,将植物的损伤程度按损伤%分级。
数字表示:
0%=无作用(与未处理对照相同)
100%=全部破坏
Claims (6)
Q1代表氧或硫,
Q2代表氧或硫,
R1代表可任选被C1-C4烷氧基取代的C1-C6烷基,或代表C2-C6链烯基,或代表C1-C6烷氧基,或代表二(C1-C4烷基)氨基,或代表C3-C6环烷基,
R2代表氟、氯或溴,或代表任选被C1-C4烷氧基取代的C1-C6烷基,或代表均可任选地被氟或氯取代的C1-C6烷氧基或C1-C6烷硫基,或代表二(C1-C4烷基)氨基,或代表C3-C6环烷基,或者
R1与R2一起代表3-11个碳原子的链烷二基,
R3代表以下基团其中R4和R5相同或不同,各自代表氢、氟、氯、溴、可任选地被氟、氯或溴取代的C1-C6烷基,或代表可任选地被氟、氯或溴取代的C2-C6链烯基,或代表可任选地被氟、氯或溴取代的C1-C4烷氧基,或代表C1-C4烷硫基,或代表基团-S(O)p-R6,其中
p代表数字2,
R6代表C1-C4烷基或二(C1-C4烷基)氨基,
R4和R5还代表苯基,
R4和/或R5还代表C1-C4烷基磺酰氧基,
或者,
R3代表以下基团其中R10代表氢,
R11和R12相同或不同,各代表氟、氯、溴、可任选地被氟和/或氯取代的C1-C4烷基或可任选地被氟和/或氯取代的C1-C4烷氧基,
或者,
A代表硫,
条件是,Q1或Q2中的一个代表硫或者二者均代表硫。
2.根据权利要求1的式(I)化合物及其钠或钾盐,其特征在于:
Q1代表氧或硫,
Q2代表氧或硫,
R1代表均可被甲氧基或乙氧基任选取代的甲基或乙基,或代表丙烯基,或代表甲氧基或乙氧基,或代表二甲氨基,或代表环丙基,
R2代表氟、氯或溴,或代表均可任选地被甲氧基或乙氧基取代的甲基、乙基、正或异丙基,或代表均可任选地被氟或氯取代的乙氧基、正或异丙氧基、甲硫基、乙硫基,或代表二甲氨基,或代表环丙基,或者
R1和R2一起代表有3-11个碳原子的链烷二基,
R3代表基团其中R4代表氟、氯或溴,或代表均可任选地被氟和/或氯取代的甲基或乙基,或代表均可任选地被氟或氯取代的甲氧基、乙氧基、甲硫基、乙硫基、乙基磺酰基或二甲氨基磺酰基,
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R3代表以下基团其中R10代表氢,
R11代表氟、氯、溴、三氟甲基、二氟甲氧基或三氟甲氧基,
R12代表氢;
或者,
条件是,Q1或Q2中的一个代表硫,或者二者均代表硫。
3.制备权利要求1的磺酰氨基羰基或硫代羰基三唑啉酮或硫代酮及其盐的方法,其特征在于:
R3-SO2-N=C=Q2 (III)其中Q2和R3各自如权利要求1中所定义,
如果合适,反应在反应助剂或稀释剂存在下进行,或者
(b)通式(IV)的三唑啉酮或硫代酮衍生物与通式(V)的磺酰胺反应,其中Q1、Q2、R1和R2各自如权利要求1所定义,Z代表卤素、烷氧基、芳氧基或芳基烷氧基,
R3-SO2-NH2 (V)其中R3如权利要求1中所定义,
如果合适,反应在酸受体或稀释剂存在下进行,或者
R3-SO2-NH-CQ2-Z (VI)其中Q2和R3各自如权利要求1中所定义,Z代表卤素、烷氧基、芳氧基或芳基烷氧基,
如果合适,反应在酸受体或稀释剂存在下进行,或者
(d)通式(II)的三唑啉酮或硫代酮与通式(VII)的磺酰卤及通式(VIII)的金属氰酸盐或硫代氰酸盐反应其中Q1、R1和R2各自如权利要求1中所定义,
R3-SO2-X (VII)其中R3如权利要求1中所定义,X代表卤素,
MQ2CN (VIII)其中Q2如权利要求1中所定义,M代表碱金属或碱土金属等效物,
如果合适,反应在反应助剂或稀释剂存在下进行;
如果需要,按方法(a)、(b)、(c)或(d)得到的式(I)化合物可以用常见方法转化成盐。
4.除草组合物,其特征在于,含有至少一种权利要求1的式(I)化合物或其盐。
5.权利要求1的通式(I)化合物或其盐为了防治不良植物生长的应用。
6.防治杂草的方法,其特征在于,使权利要求1的通式(I)化合物作用于杂草上或其栖生地上。
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AU2007267852A1 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate Hsp90 activity and methods for identifying same |
DE102007011561B4 (de) * | 2007-03-02 | 2016-03-17 | Seereal Technologies S.A. | Einrichtung zur Korrektur der Wellenlängenabhängigkeit in beugungsbasierten optischen Systemen |
WO2011133520A1 (en) | 2010-04-19 | 2011-10-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
AU2012332424A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Combination therapy of Hsp90 inhibitors with platinum-containing agents |
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EP0625515A1 (de) * | 1993-05-17 | 1994-11-23 | Bayer Ag | Substituierte Triazolinone sowie ihre Verwendung als Herbizide |
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DE3936623A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber schwefel gebundenen substituenten |
DE3936622A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Halogenierte sulfonylaminocarbonyltriazolinone |
DE3934081A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
DE3815765A1 (de) * | 1988-05-09 | 1989-11-23 | Bayer Ag | 2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel |
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DE4110795A1 (de) * | 1991-04-04 | 1992-10-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber sauerstoff gebundenen substituenten |
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DE4131842A1 (de) * | 1991-09-25 | 1993-04-01 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten |
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- 1995-01-27 DE DE19502579A patent/DE19502579A1/de not_active Withdrawn
-
1996
- 1996-01-15 EP EP96900955A patent/EP0805804B1/de not_active Expired - Lifetime
- 1996-01-15 CN CN96191629A patent/CN1088063C/zh not_active Expired - Fee Related
- 1996-01-15 ES ES96900955T patent/ES2231803T3/es not_active Expired - Lifetime
- 1996-01-15 JP JP52258596A patent/JP4086208B2/ja not_active Expired - Lifetime
- 1996-01-15 DE DE59611101T patent/DE59611101D1/de not_active Expired - Lifetime
- 1996-01-15 AU AU44866/96A patent/AU702564B2/en not_active Ceased
- 1996-01-15 US US08/875,221 patent/US5972844A/en not_active Expired - Lifetime
- 1996-01-15 WO PCT/EP1996/000141 patent/WO1996022982A1/de active IP Right Grant
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EP0294666A2 (de) * | 1987-06-12 | 1988-12-14 | Bayer Ag | Substituierte Triazolinone |
EP0415196A2 (de) * | 1989-08-30 | 1991-03-06 | Bayer Ag | Substituierte 4,5-Diamino-1,2,4-triazol-3-(thi)one |
EP0625515A1 (de) * | 1993-05-17 | 1994-11-23 | Bayer Ag | Substituierte Triazolinone sowie ihre Verwendung als Herbizide |
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Also Published As
Publication number | Publication date |
---|---|
WO1996022982A1 (de) | 1996-08-01 |
DE19502579A1 (de) | 1996-08-01 |
EP0805804A1 (de) | 1997-11-12 |
CN1169723A (zh) | 1998-01-07 |
US5972844A (en) | 1999-10-26 |
AU702564B2 (en) | 1999-02-25 |
DE59611101D1 (de) | 2004-11-04 |
AU4486696A (en) | 1996-08-14 |
JPH10512577A (ja) | 1998-12-02 |
ES2231803T3 (es) | 2005-05-16 |
JP4086208B2 (ja) | 2008-05-14 |
EP0805804B1 (de) | 2004-09-29 |
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