CN1090847A - 取代的三唑啉酮 - Google Patents
取代的三唑啉酮 Download PDFInfo
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- CN1090847A CN1090847A CN93114409A CN93114409A CN1090847A CN 1090847 A CN1090847 A CN 1090847A CN 93114409 A CN93114409 A CN 93114409A CN 93114409 A CN93114409 A CN 93114409A CN 1090847 A CN1090847 A CN 1090847A
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 96
- 229910052799 carbon Inorganic materials 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 67
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- 239000011737 fluorine Substances 0.000 claims description 55
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 54
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
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- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 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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- 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
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical compound [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Abstract
本发明涉及通式(I)的新的取代的三唑啉酮及
它们的多种制备方法和作为除莠剂、杀虫剂和杀螨剂
的用途。
其中R1、R2、R3、R4,R5,X意义详见说明书。
Description
本发明涉及新的取代的三唑啉酮、它们的多种制备方法及它们作为除莠剂、杀虫剂和杀瞒剂的用途。
已公开了某些取代的三唑啉酮,如化合物3,4-二甲基-1-(3-氟-4-氰基苯基)-1,2,4-三唑啉-5-酮或化合物3-甲基-4-炔丙基-1-(2,5-二氟-4-氰基苯基)-1,2,4-三唑啉-5-酮,具有除莠作用(参见如DE 3,839,480)。
然而,这些现有化合物在应用的所用领域对抗难对付的杂草的除莠活性及其与重要农作物的兼容性并不完全令人满意。
现已发现通式(Ⅰ)的新的取代的三唑啉酮:
式中:
R1代表卤代烷基,
R2代表氢、氨基、氰基、烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基、亚烷基亚氨基、或者各自任意取代的环烷基或环烷基烷基。
R3代表氢或卤素;
R4代表氰基或硝基;
R5代表硝基、氰基、卤素、杂环基烷氧基,或下式的基团
R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,
-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,
-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,
-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7),
或下式的基团
X代表氧或硫,其中
R6和R7各自独立地代表氢或直链或支链并被任意取代的烷基、链烯基、链炔基、环烷基、环烷基烷基、芳基烷基或芳基。
适当情况下依据取代基的性质,式(Ⅰ)化合物可以以几何异构体和/或旋光异构体形式或以不同组成的异构体混合物形式存在。本发明包括纯的异构体及异构体混合物。
另外还发现了制备通式(Ⅰ)的新的取代的三唑啉酮的方法:
式中:
R1代表卤代烷基,
R2代表氢、氨基、氰基、烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基、亚烷基亚氨基、或者各自任意取代的环烷基或环烷基烷基。
R3代表氢或卤素;
R4代表氰基或硝基;
R5代表硝基、氰基、卤素、杂环基烷氧基,或下式的基团
R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,
-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,
-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,
-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7),
或下式的基团
X代表氧或硫,其中
R6和R7各自独立地代表氢或直链或支链并被任意取代的烷基、链烯基、链炔基、环烷基、环烷基烷基、芳基烷基或芳基;所述方法包括:
a)适宜时,在稀释剂和反应助剂存在下,
式(Ⅱ)的1H-三唑啉酮
(其中R1、R2和X的定义同前),与式(Ⅲ)的卤代苯衍生物反应,
(其中R3、R4和R5定义同前,Hal代表卤素);或
b)适宜时,在稀释剂和反应助剂存在下,式(Ⅰa)的取代的三唑啉酮
(其中R1、R2、R3、R4和X定义同前,R5-1代表卤素)与式(Ⅳ)的亲核试剂反应,
R6-1-Z-H (Ⅳ)
其中Z代表氧或硫,并且
R6-1代表各自情况下的直链或支链、任意取代的烷基、链烯基、链炔基、环烷基或芳基;另外,如Z代表氧、R6-1也代表杂环基;或
c)在酸存在下并在适宜时有稀释剂存在下,式(Ⅰb)的取代的三唑啉酮与亚硝酸钠反应,
(其中R1,R3,R4,R5和X定义同前,R2-1代表氨基);或
d)适宜时,在稀释剂和反应助剂存在下,或(Ⅰc)的取代的三唑啉酮
(其中R1,R3,R4,R5和X定义如前,R2-2代表氢,与式(Ⅴ)的烷基化试剂反应,
其中R2-3代表烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基或任意取代的环烷基,以及
E代表一种吸电子离去基团。
最后还发现,通式(Ⅰ)的新的取代的三唑啉酮具有除莠、杀虫和杀螨性质。
令人惊奇的是,本发明的通式(Ⅰ)的取代的三唑啉酮,与现有技术已知的取代的三唑啉酮相比,如与化合物3,4-二甲基-1-(3-氟-4-氰基苯基)-1,2,4-三唑啉-5-酮或化合物3-甲基-4-炔丙基-1-(2,5-二氟-4-氰基苯基)-1,2,4-三唑啉-5-酮比较,对于难对付的杂草具有好得多的除莠活性,同时出乎意料地具有好得多的杀螨活性。这些取代的三唑啉酮在化学上和其作用方式上都是相似的。
式(Ⅰ)提供了本发明取代的三唑啉酮的一般定义。式(Ⅰ)的优选化合物是下述化合物,其中:
R1代表直链或支链的卤代烷基,所述基团含1至6个碳原子,1至13个相同或不同的卤素原子,特别是氟、氯、溴或碘;
R2代表氢;氨基;氰基;含1至8个碳原子的直链或支链烷基;含2至6个碳原子的直链或支链的链烯基或链炔基;直链或支链的卤代烷基,所述基团含有1至6个碳原子和1至13个相同的或不同的卤素原子,特别是氟、氯、溴或碘;直链或支链的卤代链烯基或卤代链炔基,所述基团含有2至6个碳原子和1至11个相同的或不同的卤素原子,特别是氟、氯、溴或碘;直链或支链的烷氧基烷基,其中每个单个的烷基部分含有1至4个碳原子;含1至8个碳原子的直链或支链亚烷基亚氨基;或者环烷基或环烷基烷基,其中的环烷基部分含3~8个碳原子,并在适宜时直链或支链烷基部分含有1~4个碳原子,且环烷基部分可任意被相同的或不同的卤素取代基(特别是氟、氯、溴和/或碘)单取代或多取代;
R3代表氢、氟、氯、溴或碘;
R4代表氰基或硝基;
R5代表硝基;氰基;氟;氯;溴;碘;或杂环基-C1-C4-烷氧基,杂环基团表示一个3-至7-元,任意苯并的、饱和或不饱和杂环,并含1至3个相同或不同的杂原子,特别是氮、氧和/或硫;或下式的基团:R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,
-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7)或下式的基团:
X代表氧或硫;其中
R6和R7各自独立地代表氢或者直链或支链的烷基,所述烷基含1至8个碳原子并任意被相同或不同的取代基单取代或多取代,适宜的取代基为:
卤素,特别是氟、氯、溴和/或碘;氰基;羧基;氨基甲酰基;直链或支链的烷氧基、烷氧基烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氧基羰基、烷氧基羰基烷基、N-烷基氨基羰基、环烷基氨基羰基、N,N-二烷基氨基羰基、三烷基甲硅烷基或烷基磺酰基氨基羰基,每个上述基团的单个烷基部分都含有1~8个碳原子;或杂环基、杂环基为一种5-至7元的、任意苯并的、饱和或不饱和的杂环,含1至3个相同的或不同的杂原子,特别是氮、氧和/或硫;
R6和R7还代表链烯基或链炔基,各含2至8个碳原子,并可任意被相同或不同的卤素取代基(特别是氟、氯、溴和/或碘)单取代或多取代;
R6和R7还代表含3至7个碳原子的环烷基,它可任意被相同或不同的卤素取代基(特别是氟、氯、溴和/或碘)和/或含1至4个碳原子的直链或支链烷基单取代或多取代;或代表C3-C7-环烷基-C1-C3-烷基;或;
R6和R7代表芳基烷基或芳基,各自的芳基部分含有6至10个碳原子,适宜时在直链或支链烷基部分含有1至4个碳原子,各自的芳基部分可任意被相同或不同的取代基单取代或多取代,各自适宜的芳基的取代基为:
卤素,氰基,硝基,含1至6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,含1至6个碳原子和1至13个相同或不同的卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,在单个的烷基部分有1至6个碳原子的直链或支链烷氧基羰基或烷氧基亚氨基烷基,和苯基,该苯基任意被相同或不同的卤素取代基和/或被含1至6个碳原子的直链或支链烷基或烷氧基和/或被含1至6个碳原子和1至13个相同或不同卤素原子的直链或支链卤代烷基或卤代烷氧基单取代或多取代。
特别优选的式(Ⅰ)化合物是下述化合物,其中:
R1代表含1至4个碳原子和1至9个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代烷基;
R2代表氢,氨基,氰基,含1至6个碳原子的直链或支链烷基,含2至4个碳原子的直链或支链链烯基或链炔基,含1至4
其中:
Z代表氧或硫,且
R6-1代表任意取代的直链或支链烷基、链烯基、链炔基、环烷基或芳基,而且,如果Z代表氧时,则R6-1也代表杂环基。
或在于:
c)适宜时,在酸和稀释剂存在下,式(Ⅰb)的取代的三唑啉酮和亚硝酸钠反应:
其中:
R1、R3、R4、R5和X具有前述意义,且
R2-1代表氨基。
或在于:
d)适宜时,在稀释剂和反应助剂存在下,式(Ⅰc)的取代的三唑啉酮和式(Ⅴ)的烷基化试剂反应:
的直链或支链烷基,适宜的取代基为:
氰基,羧基,氨基甲酰基,各烷基部分含1至6个碳原子的直链或支链烷氧基、烷氧基烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氧基羰基、烷氧基羰基烷基,N-烷基氨基羰基、N,N-二烷基氨基羰基、三烷基甲硅烷基或烷基磺酰基氨基羰基;或5元或6元的、含1至3个相同或不同杂原子(特别是氮、氧和/或硫)的饱和或不饱和的杂环基;
R6和R7还代表含有1至4个碳原子和1至9个相同或不同的卤素原子(特别是氟、氯或溴)的、并可进一步任意被C1-2烷氧基羰基、C1-5环烷基氨基羰基或氰基取代的直链或支链卤代烷基;
R6和R7还代表含2至6个碳原子,并任意被相同或不同的卤素取代基(特别是氟、氯或溴)单取代至三取代的链烯基或链炔基;
R6和R7还代表含3至6个碳原子并任意被相同或不同的卤素取代基(特别是氟、氯或溴)和/或被含1至3个碳原子的直链或支链烷基单取代至四取代的环烷基,或代表C3-6环烷基-C1-C2-烷基,或
代表苯基烷基或苯基(前者的直链或支链烷基部分含1至3个碳原子),两者的苯基部分任意被相同或不相同的取代基单取代至三取代,各自苯基的适宜取代基为:
卤素,氰基,硝基,含1至4个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,含1至4个碳原子和1至9个相同或不同卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基;在单个烷基部分中含1至4个碳原子的直链或支链烷氧基羰基或烷氧基亚氨基烷基,和苯基,该苯基任意被相同或不同卤素取代基和/或被含1至4个碳原子的直链或支链烷基或烷氧基和/或被含1至4个碳原子和1至9个相同或不同的卤素原子的直链或支链卤代烷基或卤代烷氧基单取代或多取代。
更特别优选的式(Ⅰ)化合物是下述化合物,其中:
R1代表含1至2个碳原子和1至5个相同或不同卤素原子(特别是氟或氯)的卤代烷基;
R2代表氢,氨基,氰基,含1至4个碳原子的直链或支链烷基,含2至3个碳原子的直链或支链链烯基或链炔基,含1至2个碳原子和1至5个相同或不同卤素原子(特别是氟、氯或溴)的卤代烷基,含2至3个碳原子和1至3个相同或不同卤素原子(特别是氟或氯)的直链或支链卤代链烯基或卤代链炔基,各烷基部分含1或2个碳原子的直链或支链烷氧基烷基,含1至6个碳原子的直链或支链亚烷基亚氨基,或环丙基、环丙基甲基、环己基或环己基甲基,各自的环烷基部分任意被相同或不同的卤素取代基(特别是氟或氯)单取代或二取代;
R3代表氢、氟或氯;
R4代表氰基或硝基;
R5代表硝基、氰基、氟、氯、溴或杂环基甲氧基,其中杂环基团为5或6元环,含1至3个相同或不同杂原子(特别是氮、氧和/或硫)的饱和或不饱和杂环;或代表下式的基团:
R6、-O-R6、-S-R6、-S(O)-R6,-SO2-R6,
-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,
-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,
-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7)或下式的基团:
X代表氧或硫;其中
R6和R7各自独立地代表氢或含1至4个碳原子的任意单取代的直链或支链烷基,适宜的取代基为:
氰基,羧基,氨基甲酰基,各烷基部分含1至3个碳原子的直链或支链烷氧基、烷氧基烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氧基羰基、烷基羰基烷基、N-烷基氨基羰基、N,N-二烷基氨基羰基、三烷基甲硅烷基或烷基磺酰基氨基羰基,或含有1至3个相同或不同的杂原子(特别是氮、氧和/或硫)的5元或6元饱和或不饱和杂环基团;
R6和R7还代表含1或2个碳原子和1至5个相同或不同卤素原子(特别是氟或氯),并还任意被甲氧基羰基、乙氧基羰基、氰基或环丙基氨基羰基取代的卤代烷基;
R6和R7还代表含2至5个碳原子并任意被卤素(特别是氟或氯)单取代的链烯基和链炔基;
R6和R7还代表任意被选自氟、氯、甲基和/或乙基的相同或不同取代基单取代或二取代的环丙基或环己基,或代表环丙基甲基、环戊基甲基或环己基甲基;或
R6和R7代表苯基烷基或苯基(前者烷基部分含1至2个碳原子),各自的苯基部分任意被相同或不同的取代基单取代或二取代,适宜的苯基的取代基为:
氟,氯,溴,氰基,硝基,甲基,乙基,n-或i-丙基,n-、i-、s-或t-丁基,甲氧基,乙氧基,n-或i-丙氧基,n-、i-、s-或t-丁氧基,甲硫基,乙硫基甲基亚磺酰基,甲基磺酰基,三氟甲基,二氟甲基,三氟甲氧基,二氟甲氧基,三氟甲硫基,三氟甲基亚磺酰基,三氟甲基磺酰基,甲氧基羰基,乙氧基羰基,甲氧基亚氨基甲基,甲氧基亚氨基乙基,乙氧基亚氨基甲基,乙氧基亚氨基乙基,或任意被选自氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基和/或三氟甲氧基的相同或不同取代基单取代或二取代的苯基。
除了在制备实施例中给出的化合物外,还可逐一给出下述式(Ⅰ)的取代的三唑啉酮:
R1R2R3R4R5X
CF3CH3F CN OH O
CF3CH3Cl CN OH O
CF3CH3F NO2OH O
CF3CH3Cl NO2OH O
CF3CH3Cl CN CH3O O
CF3CH3Cl NO2CH3O O
CF3CH3F NO2CH3O O
CF3CH3F CN -O-CH2-C≡CH O
CF3CH3Cl CN -O-CH2-C≡CH O
CF3CH3F NO2-O-CH2-C≡CH O
CF3CH3Cl NO2-O-CH2-C≡CH O
CF3CH3F CN O
CF3CH3Cl CN O
CF3CH3F NO2O
CF3CH3Cl NO2O
R1R2R3R4R5X
CF3CH3F CN O
CF3CH3Cl CN O
CF3CH3F NO2O
CF3CH3Cl NO2O
CF3CH3F CN -O-CH2-CN O
CF3CH3Cl CN -O-CH2-CN O
CF3CH3F NO2-O-CH2-CN O
CF3CH3Cl NO2-O-CH2-CN O
CF3CH3F CN O
CF3CH3Cl CN O
R1R2R3R4R5X
CF3CH3F NO2O
CF3CH3Cl NO2O
CF3CH3F CN O
CF3CH3Cl CN O
CF3CH3Cl NO2O
CF3CH3F NO2O
CF3CH3F CN -O-SO2-CH3O
CF3CH3Cl CN -O-SO2-CH3O
CF3CH3F NO2-O-SO2-CH3O
CF3CH3Cl NO2-O-SO2-CH3O
CF3CH3F CN -O-CH2-COOCH3O
R1R2R3R4R5X
CF3CH3Cl CN -O-CH2-COOCH3O
CF3CH3F NO2-O-CH2-COOCH3O
CF3CH3Cl NO2-O-CH2-COOCH3O
CF3CH3F NO2F O
CF3CH3Cl NO2F O
CF3CH3F NO2Cl O
CF3CH3Cl NO2Cl O
CF3CH3F CN -O-CHF2O
CF3CH3Cl CN -O-CHF2O
CF3CH3F NO2-O-CHF2O
CF3CH3Cl NO2-O-CHF2O
CF3CH3F CN -S-CH3O
CF3CH3Cl CN -S-CH3O
CF3CH3F NO2-S-CH3O
CF3CH3Cl NO2-S-CH3O
R1R2R3R4R5X
CF3CH3F CN -S-C2H5O
CF3CH3Cl CN -S-C2H5O
CF3CH3F NO2-S-C2H5O
CF3CH3Cl NO2-S-C2H5O
CF3CH3F CN O
CF3CH3Cl CN O
CF3CH3F NO2O
CF3CH3Cl NO2O
CF3CH3F CN O
CF3CH3Cl CN O
CF3CH3F NO2O
CF3CH3Cl NO2O
R1R2R3R4R5X
CF3CH3Cl CN -S-CH2-COOCH3O
CF3CH3F CN -S-CH2-COOCH3O
CF3CH3Cl NO2-S-CH2-COOCH3O
CF3CH3F NO2-S-CH2-COOCH3O
CF3CH3F CN CH3O
CF3CH3F CN -S(O)-CH3O
CF3CH3F CN ′-SO2-CH3O
CF3CH3F CN -SO2-O-CH3O
CF3CH3F CN -SO2-NH-CH3O
CF3CH3F CN -NH-CH3O
CF3CH3F CN -N(CH3)2O
CF3CH3F CN -COOCH3O
CF3CH3F CN -COOC2H5O
CF3CH3Cl NO2-COOCH3O
CF3CH3Cl NO2-COOC2H5O
CF3CH3F CN -CO-NH-CH3O
CF3CH3F CN -CO-N(CH3)-CH3O
R1R2R3R4R5X
CF3CH3F CN O
CF3CH3F CN O
CF3C2H5F CN OH O
CF3C2H5F CN OCH3O
CF3C2H5F CN -O-CH2-CH=CH2O
CF3C2H5F CN -O-CH2-C≡CH O
CF3C2H5F CN -O-CH2-COOCH3O
CF3C2H5F CN -S-CH3O
CF3C2H5F CN -S-C2H5O
CF3C2H5F CN F O
R1R2R3R4R5X
CF3C2H5F CN O
CF3C2H5F CN O
CF3C2H5Cl CN OCH3O
CF3C2H5Cl CN -S-C2H5O
CF3C2H5F NO2OCH3O
CF3C2H5Cl NO2-O-CH2-C≡CH O
CF3C2H5Cl CN O
CF3C2H5F NO2O
CF3C2H5Cl NO2O
CF3C2H5F CN O
CF3C2H5F CN -O-CH2-C6H5O
CF3-CH2-CH=CH2F CN OH O
CF3-CH2-CH=CH2F CN OCH3O
R1R2R3R4R5X
CF3-CH2-CH=CH2F CN -O-CH2-CH=CH2O
CF3-CH2-CH=CH2F CN -O-CH2-C≡CH- O
CF3-CH2-CH=CH2F CN
O
CF3-CH2-CH=CH2F CN -O-CH2-COOCH3O
CF3-CH2-CH=CH2F CN -S-CH3O
CF3-CH2-CH=CH2F CN -S-C2H5O
CF3-CH2-CH=CH2F CN F O
CF3-CH2-CH=CH2F CN
O
CF3-CH2-CH=CH2Cl CN OCH3O
CF3-CH2-CH=CH2Cl CN -S-C2H5O
CF3-CH2-CH=CH2F NO2OCH3O
CF3-CH2-CH=CH2Cl NO2-O-CH2O≡CH O
R1R2R3R4R5X
CF3-CH2-CH=CH2Cl CN O
CF3-CH2-CH=CH2F NO2O
CF3-CH2-CH=CH2Cl NO2O
CF3-CH2-CH=CH2F CN O
CF3-CH2-CH=CH2F CN -O-CH2-C6H5O
CF3-CHF2F CN OH O
CF3-CHF2F CN OCH3O
CF3-CHF2F CN -O-CH2-CH=CH2O
CF3-CHF2F CN -O-CH2-C≡CH O
CF3-CHF2F CN -O-CH2-COOCH3O
CF3-CHF2F CN -S-CH3O
CF3-CHF2F CN -S-C2H5O
R1R2R3R4R5X
CF3-CHF2F CN
O
CF3-CHF2F CN F O
CF3-CHF2Cl CN OCH3O
CF3-CHF2Cl CN -S-C2H5O
CF3-CHF2F NO2OCH3O
CF3-CHF2Cl NO2-O-CH2-C≡CH O
CF3-CHF2Cl CN O
CF3-CHF2F NO2O
CF3-CHF2Cl NO2O
CF3-CHF2F CN O
R1R2R3R4R5X
CF3-CHF2F CN -O-CH2-C6H5O
CF3F CN OH O
CF3F CN OCH3O
CF3F CN -O-CH2-CH=CH2O
CF3F CN -O-CH2-C≡CH O
CF3F CN
O
CF3F CN -O-CH2-COOCH3O
CF3F CN -S-CH3O
CF3F CN -S-C2H5O
CF3F CN F O
R1R2R3R4R5X
CF3Cl CN OCH3O
CF3Cl CN -S-C2H5O
CF3F NO2OCH3O
CF3Cl NO2-O-CH2-C≡CH O
CF3F NO2 O
R1R2R3R4R5X
-CHF2CH3F CN OH O
-CHF2CH3F CN OCH3O
-CHF2CH3F CN -O-CH2-CH=CH2O
-CHF2CH3F CN -O-CH2-O=OH O
-CHF2CH3F CN -O-CH2-COOCH3O
-CHF2CH3F CN -S-CH3O
-CHF2CH3F CN -S-C2H5O
-CHF2CH3F CN
O
-CHF2CH3F CN F O
-CHF2CH3F CN O
-CHF2CH3F CN O
R1R2R3R4R5X
-CHF2CH3Cl CN OCH3O
-CHF2CH3Cl CN -S-C2H5O
-CHF2CH3F NO2OCH3O
-CHF2CH3Cl NO2-O-CH2-C≡CH O
-CHF2CH3Cl CN O
-CHF2CH3F NO2O
-CHF2CH3Cl NO2O
-CHF2CH3F CN O
-CHF2CH3F CN -O-CH2-C6H5O
-CF2Cl CH3F CN OH O
-CF2Cl CH3F CN OCH3O
-CF2Cl CH3F CN -O-CH2-CH=CH2O
-CF2Cl CH3F CN -O-CH2-C≡CH O
R1R2R3R4R5X
-CF2Cl CH3F CN -O-CH2-COOCH3O
-CF2Cl CH3F CN -S-CH3O
-CF2Cl CH3F CN -S-C2H5O
-CF2Cl CH3F CN F O
-CF2Cl CH3F CN O
-CF2Cl CH3F CN O
-CF2Cl CH3Cl CN OCH3O
-CF2Cl CH3Cl CN -S-C2H5O
-CF2Cl CH3F NO2OCH3O
-CF2Cl CH3Cl NO2-O-CH2-C≡CH O
R1R2R3R4R5X
-CF2Cl CH3F NO2O
-CF2Cl CH3Cl NO2O
-CF2Cl CH3F CN O
-CF2Cl CH3F CN -O-CH2-C6H5O
-CCl3CH3F CN OH O
-CCl3CH3F CN OCH3O
-CCl3CH3F CN -O-CH2-CH=CH2O
-CCl3CH3F CN -O-CH2-C≡CH O
-CCl3CH3F CN -O-CH2-COOCH3O
-CCl3CH3F CN -S-CH3O
-CCl3CH3F CN -S-C2H5O
R1R2R3R4R5X
-CCl3CH3F CN F O
-CCl3CH3F CN O
-CCl3CH3F CN O
-CCl3CH3Cl CN OCH3O
-CCl3CH3Cl CN -S-C2H5O
-CCl3CH3F NO2OCH3O
-CCl3CH3Cl NO2-O-CH2-C≡CH O
-CCl3CH3Cl CN O
-CCl3CH3F NO2O
-CCl3CH3Cl NO2O
-CCl3CH3F CN O
-CCl3CH3F CN -O-CH2-C6H5O
CF3CH3F CN OH S
R1R2R3R4R5X
CF3CH3F CN -O-i-C3H7S
CF3CH3F CN -O-CH2-CH=CH2S
CF3CH3F CN -O-CH2-C≡CH S
CF3CH3F CN -O-CH2-COOCH3S
CF3CH3F CN -S-CH3S
CF3CH3F CN -S-C2H5S
CF3CH3F CN F S
CF3CH3F CN S
CF3CH3F CN S
CF3CH3Cl CN OCH3S
CF3CH3Cl CN -S-C2H5S
CF3CH3F NO2OCH3S
R1R2R3R4R5X
CF3CH3Cl NO2-O-CH2-C≡CH S
CF3CH3Cl CN S
CF3CH3F NO2S
CF3CH3Cl NO2S
CF3CH3F CN S
CF3CH3F CN -O-CH2-C6H5S
CF3-CHF2F CN OH S
CF3-CHF2F CN OCH3S
CF3-CHF2F CN -O-CH2-CH=CH2S
CF3-CHF2F CN -O-CH2-C≡CH S
R1R2R3R4R5X
CF3-CHF2F CN -O-CH2-COOCH3S
CF3-CHF2F CN -S-CH3S
CF3-CHF2F CN -S-C2H5S
CF3-CHF2F CN F S
CF3-CHF2F CN S
CF3-CHF2F CN S
CF3-CHF2Cl CN OCH3S
CF3-CHF2Cl CN -S-C2H5S
CF3-CHF2F NO2OCH3S
CF3-CHF2Cl NO2-O-CH2-C≡CH S
R1R2R3R4R5X
CF3-CHF2F NO2S
CF3-CHF2Cl NO2S
CF3-CHF2F CN S
CF3-CHF2F CN -O-CH2-C6H5S
例如,如果用4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮和2,4,5-三氟苄腈为原料,本发明的方法(a)的反应过程可以用下述反应式表示:
例如,如果用1-(4-氰基-2,5-二氟苯基)-4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮和3-丁炔-2-醇为原料,本发明的方法(b)的反应过程可以用下述反应式表示:
例如,如果用1-(4-氰基-2,5-二氟苯基)-4-氨基-3-三氟甲基-1,2,4-三唑啉-5-酮和亚硝酸钠为原料,本发明的方法(c)的反应过程可以用下述反应式表示:
例如,如果用1-(4-氰基-2,5-二氟苯基)-3-三氟甲基-(4H)-1,2,4-三唑啉-5-酮和一氯二氟甲烷为原料,本发明的方法(d)的反应过程可以用下述反应式表示:
式(Ⅱ)给出了用于实施本发明方法(a)所需原料1H-三唑啉酮的一般定义。在式(Ⅱ)中,R1、R2和X优选且特别优选代表在本发明的式(Ⅰ)化合物的描述中已叙述过的作为优选和特别优选取代基的那些基团。
式(Ⅲ)的1H-三唑啉酮是已知化合物,或可按类似于已知的方法制得,参见如:EP399,294;US4,477,459;DE2,716,707;US3,780,052;J.Med.Chem.14期,335-338页(1971年);DE2,029,375。化合物4-氨基-3-三氟甲基-1H-1,2,4-三唑啉-5-酮迄今尚未为人所知,它也是本发明的主题之一。它以下述方式获得:在-20℃至+200℃温度下,水合肼先和碳酸二苯酯反应,然后和三氟乙酸反应(对照本说明书的制备实施例)。
式(Ⅲ)给出了用于实施本发明方法(a)的还需要的原料卤代苯衍生物的一般定义,在式(Ⅲ)中,R3、R4和R5优选并特别优选代表在本发明的式(Ⅰ)化合物中的描述中已叙述过的作为优选和特别优选取代基的那些基团。Hal代表氟、氯或溴,特别是氟或氯。
式(Ⅲ)的卤代苯衍生物已经公开或可以按类似于已知的方法获得(参见如EP191,181;EP441,004;EP431,373)。化合物5-氯-2,4-二氟苄腈迄今为止尚未为人所知,它也是本发明的主题之一。它以下述方式获得:适宜时,在100℃至200℃间温度下,在有稀释剂(如四氢噻吩砜)存在下,已知化合物2,4,5-三氯苄腈(参照如EP441,004)和氟化钾反应(参照本说明书的制备实施例)。
式(Ⅰa)给出了用于实施本发明的方法(b)所需的离析物取代的三唑啉酮的一般定义。在式(Ⅰa)中,R1、R2、R3、R4和X优选并特别优选代表在本发明的式(Ⅰ)物质中描述中叙述过的作为优选和特别优选的那些取代基。R5-1优选代表氟、氯或溴,特别是氟或氯。
式(Ⅰa)的取代的三唑啉酮为依本发明定义的化合物并可借助于本发明的方法(a),(c)和/或(d)获得。
式(Ⅳ)给出了用于实施本发明的方法(b)所需要的离析物亲核试剂的一般定义。在式(Ⅳ)中,Z优选代表氧或硫。R6-1优选并特别优选代表在本发明式(Ⅰ)物质的描述中叙述过的作为优选和特别优选的取代基R2的那些基团(氢除外)。如果Z代表氧,则R6-1还优选代表杂环基,它有5-至7-元的,任意苯并,含1至3个相同或不同的杂原子(特别是氮、氧和/或硫)的饱和或不饱和的杂环,优选称作杂环基。
式(Ⅳ)的亲核试剂为一般已知的有机化合物。
式(Ⅰb)给出了用于实施本发明的方法(c)所需的离析物取代的三唑啉酮的一般定义。在式(Ⅰb)中。R1、R3、R4、R5和X优选且特别优选代表在本发明式(Ⅰ)物质的描述中叙述过的作为优选和特别优选的取代基的那些基团。R2-1优选代表氨基。
式(Ⅰb)的取代的三唑啉酮为依据本发明定义的化合物并可借助于本发明的方法(a)、(b)和/或(d)而获得。
式(Ⅰc)给出了用于实施本发明的方法(d)所需的离析物取代的三唑啉酮的一般定义。在式(Ⅰc)中,R1、R3、R4、R5和X优选和特别优选代表在本发明的式(Ⅰ)化合物描述中叙述过的作为优选和特别优选的取代基的那些基团。R2-2优选代表氢。
式(Ⅰc)的取代的三唑啉酮为依据本发明定义的化合物,并可借助于本发明的方法(a),(b)和/或(c)获得。
式(Ⅴ)给出了用于实施本发明的方法(d)还需的离析物烷基化试剂的一般定义。在式(Ⅴ)中,R2-3优选并特别优选代表在本发明的式(Ⅰ)物质的描述中叙述过的作为优选和特别优选的取代基R2的那些基团(只是氢、氨基、氰基和亚烷基亚氨基除外)。E优选代表离去基团,它在烷基化试剂中(如卤素,特别是氟、氯或碘)是常见的,或任意取代的烷基磺酰基氧基,烷氧基磺酰基氧基,或芳基磺酰基氧基,如特别是甲基磺酰基氧基,三氟甲基磺酰基氧基,甲氧基磺酰基氧基,乙氧基磺酰基氧基或P-甲苯磺酰基氧基。
式(Ⅴ)的烷基化试剂为一般已知的有机化合物。
本发明的方法(a)适用稀释剂为惰性有机溶剂。它们特别包括脂族的、脂环族的、芳族的任意卤化的烃,如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳;醚,如二乙醚、二异丙基醚、二噁烷、四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮,如丙酮、丁酮或甲基-异丁基酮;腈,如乙腈、丙腈或苄腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷三酰胺;或酯,如乙酸甲酯或乙酸乙酯。
本发明的方法(a)优选在一种适宜的反应助剂存在下进行。可用的反应助剂为所有常见的无机或有机碱。这些碱优选包括碱土金属氢氧化物或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾或氢氧化铵;碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵;碱金属乙酸盐或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙或乙酸铵;或叔胺,如三甲基胺、三乙基胺、三丁基胺、N,N-二甲基苯胺、吡啶、哌啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
在实施本发明的方法(a)时,反应温度可在一个相当大的范围内变化。一般地,反应在0℃和+180℃之间,优选在+20℃和+120℃之间的温度下进行。
本发明的方法(a)一般在大气压下实施。本方法也可能在加压或减压条件下实施。
在实施本发明的方法(a)时,每摩尔式(Ⅱ)的1H-三唑啉酮一般用1.0至3.0摩尔,优选1.0至1.5摩尔的式(Ⅲ)的卤代苯衍生物,以及适宜时1.0至3.0摩尔,优选1.0至1.5摩尔的作反应助剂的碱。用已知的方法进行反应并加工,分离反应产物(参照制备实施例)。
实施本发明的方法(b)时可能的稀释剂为惰性有机溶剂。优选使用的溶剂列于本发明的方法(a)的说明中。
本发明的方法(b)优选在一种适宜的反应助剂存在下实施。可用的助剂为所有常见的无机或有机碱。它们包括如碱土金属或碱金属的氢化物:氢氧化物、氨化铵、醇化物、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨基钠、甲醇钠、乙醇钠、t-丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,及叔胺如三甲基胺、三乙基胺、三丁基胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DNB)或二氮杂双环十一碳烯(DBU)。
实施本发明的方法(b)时,反应温度可在一个较大范围变化。一般在-20℃至+150℃范围,优选0℃至+120℃范围实施该方法。
本发明的方法(b)通常在大气压下实施。但也可能在减压或加压下实施。
在实施本发明的方法(b)时,每摩尔式(Ⅰa)取代的三唑啉酮一般用1.0至3.0摩尔,优选1.0至1.5摩尔式(Ⅰv)的亲核试剂及适宜时,0.1至3.0摩尔,优选1.0至1.5摩尔的作为反应助剂的碱。
用已知方法进行反应并对反应产物加工和分离(参照制备实施例)。
本发明的方法(c)一般在一种适宜的酸存在下实施。适用的酸(特别)是无机酸水溶液。特别优选用稀盐酸。
实施本发明的方法(C)时,适宜的稀释剂为所有常用于这种重氮化反应的稀释剂。优选采用适当过量的用作试剂的无机酸水溶液,同时用它作为稀释剂,如盐酸。
实施本发明的方法(c)时,反应温度可在一较大范围变化。一般地,该方法在-20℃至+100℃。优选在-10℃至+80℃温度间实施。
本发明的方法(c)一般在大气压下实施。但也可能在加压或减压条件下实施。
实施本发明的方法(c)时,每摩尔式(Ⅰb)的取代的三唑啉酮用1.0至3.0摩尔,优选1.0至2.0摩尔的亚硝酸钠和1.0至10.0摩尔,优选1.0至5.0摩尔的酸。
用已知方法实施本反应并对反应产物加工和分离(参照制备实施例)。
实施本发明的方法(d)可用的稀释剂为隋性有机溶剂。它们(特别)包括脂族的、脂环族的、芳香族的任意卤代的烃,如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚,如二乙基醚、二异丙基醚、二噁烷、四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮,如丙酮,丁酮或甲基异丁基酮;腈,如乙腈、丙腈或苄腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷三酰胺;酯,如乙酸甲酯或乙酸乙酯,或亚砜,如二甲基亚砜。
适宜时,本发明的方法(d)还可在一个两相体系(如水/甲苯或水/二氯甲烷)及在适宜时在一种适宜的相转移催化剂存在下实施。这种可列举的催化剂的例子有:碘化四丁铵、溴化四丁铵、氯化四丁铵、溴化三丁基甲基鏻、氯化三甲基-C13/C15-烷基铵、溴化三甲基-C13/C15-烷基铵、硫酸甲酯二苄基二甲基铵、氯化二甲基-C12/14-烷基苄基铵、溴化二甲基-C12/C14-烷基苄基铵、氢氧化四丁铵、氯化三乙基苄基铵,氯化甲基三辛基铵、氯化三甲基苄基铵、15-冠-5、18-冠-6或三-[2-(2-甲氧基乙氧基)乙基]胺。
本发明的方法(d)优选在一种适宜的反应助剂存在下实施。适宜的反应助剂包括所有常见的无机或有机碱。它们包括如碱土金属和碱金属的氢化物、氢氧化物,氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,如三甲基胺、三乙基胺、三丁基胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
实施本发明的方法(d)时,反应温度可在较大范围变化。一般在-20℃至+150℃,优选在0℃至+120℃范围实施本方法。
本发明的方法(d)一般在大气压下实施。但也可能在加压或减压条件下实施。
实施本发明的方法(d)时,每摩尔式(Ⅰc)的取代的三唑啉酮用1.0至3.0摩尔,优选1.0至2.0摩尔的式(Ⅴ)的烷基化试剂,并在适宜时用1.0至3.0摩尔,优选1.0至2.0摩尔的作为反应助剂的碱。
用已知的方法进行该反应并加工、分离反应产物(参照制备实施例)。
式(Ⅰ)的最终产物用常规方法(如柱色谱或重结晶)提纯。
它们以熔点法表征,而当化合物不结晶时,则用核磁共振氢谱(1H NMR)表征。
本发明的活性化合物可用作脱叶剂、干燥剂、除阔叶植物剂,特别是可用作除杂草剂。所谓杂草,从最广泛的意义上来说,所有的植物,只要是生长在人们所不希望它生长的地方,都可以称之为杂草。使用本发明的化合物除去所有的杂草,还是有选择地除去某些种类的杂草,主要取决于所用的量。
本发明的活性化合物可用于除去下列植物:
以下各属的双子叶杂草:
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,番诸属,蓼属,田菁属,脉草属,蓟属,飞廉属,苦苣菜属,茄属,焊菜属,水松叶属,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,车轴草属,毛莨属和蒲公英属。
以下各属的双子叶栽培作物:
棉属,大豆属,胡罗卜属,菜豆属,豌豆属,茄属,亚麻属,番诸属,巢菜属,菸草属,番茄属,落花生属,芸苔属,莴苣属,甜瓜属和南瓜属。
以下各属的单子叶杂草:
稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,参属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,蜀黍属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,莞草属,雀稗属,鸭嘴草属,密穗桔梗属,龙爪茅属,翦股颖属,看麦娘属和豚鼠草属。
以下各属的单子叶栽培作物:
稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,蜀麦属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
但本发明的活性化合物决不局限用于上述各属的植物,它们也可以同样方式用于其它植物。
本发明的化合物,按照使用的浓度不同,适用于清除工业场地、铁路轨道、有树或无树的小路和场院的所有杂草。同样,这些化合物也可用于清除多年生栽培作物(如人工林、装饰林带、果园、葡萄园、柑桔园、坚果林、香蕉林、咖啡园、茶园、橡胶林、油棕榈林、可可林、浆果园和蛇麻草田)中的杂草,以及选择性地清除一年生栽培作物中的杂草。
本发明的活性化合物还可特别有效地用于清除单子叶和双子叶杂草。
此活性化合物还适用于清除害虫。优选节肢动物和线虫,特别是在农业,森林、贮存产品的保护及卫生领域中遇到的昆虫和蜘蛛。它们对于通常敏感和有抗性的物种及其全部或部分发育阶段均有活性。上述害虫包括:
等足目,例如潮虫、平甲虫和鼠妇。
倍足目,例如具斑马陆。
唇足目,例如食果地蜈蚣和蚰蜒属。
扁肩象目,例如庭院么蚰。
缨尾目,例如西洋衣鱼。
弹尾目,例如具刺跳虫。
直翅目,例如东方蜚蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼姑属,热带飞蝗,殊种蚱蜢和沙漠蝗。
革翅目,例如欧洲球螋。
等翅目,例如犀白蚁属。
虱目,例如葡萄瘤蚜,绵蚜属,体虱,血虱属和长颚虱属。
食毛目,例如嚼虱属和畜虱属。
缨翅目,例如温室条蓟马和葱蓟马。
异翅亚目,例如扁盾蝽属,红蝽属,方背皮蝽,温带臭虫,长红蜡蝽和蜡蝽属。
半翅目,例如甘蓝粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶蔗隐瘤蚜,Doralis fabae,Doralis Pomi,苹果绵蚜,桃大尾蚜,稠李溢管蚜,微叶蝉属,双叶叶蝉,黑尾时蝉,麦长管蚜,瘤蚜属,忽布疣蚜,李蜡蚧,油榄黑盔蚧,灰飞虱、稻褐飞虱,红圆蚧,夹竹桃圆蚧,粉蚧属和木虱属。
鳞刺目,例如棉红铃虫,松天蚜,冬天蛾,苹细蛾,苹果巢蛾,小菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾属,棉潜蛾,桔叶潜蛾,地虎属,刀根虫属,夜蛾属,棉斑实蛾,实夜蛾属,甜菜夜蛾,甘蓝夜蛾,小眼夜蛾,斜纹夜蛾,粘虫属,粉纹夜蛾,苹蠹蛾,粉蝶属,螟属,玉米螟,地中海粉螟,大蜡螟,负袋衣蛾,织网衣蛾,褐织衣蛾,亚麻黄卷蛾,具网卷叶蛾,云松卷蛾,葡萄果蠹蛾,茶长卷蛾,栋绿卷叶蛾。
鞘翅目,例如具斑窃蠹、谷蠹,豆象,大豆象,家天牛,赤杨紫跳甲,马铃薯甲虫,辣根猿叶虫,叶甲属,油菜蓝跳甲,墨西哥豆飘虫,隐金甲属,锯谷盗,花象甲属,谷象属,葡萄黑象甲,香蕉根象甲,甘蓝荚象甲,苜蓿叶象甲,皮蠹属,斑皮蠹属,圆皮蠹属,毛皮蠹属,粉蠹属,油菜花露尾甲、蛛甲属,金黄蛛甲,麦蛛甲,拟谷盗属,大黄粉虫,叩甲属,金针虫属,西方五月鳃角金龟,六月金龟和褐新西兰肋翅鳃角金龟。
膜刺目,例如锯角叶蜂属,叶蜂尾,蚁尾,厨蚁和胡蜂属。
双翅目,如伊蚊属,按蚊属,库蚊属,黄猩猩果蝇,家蝇属,厕蝇属,红头丽蝇,绿蝇属,金蝇属,疽蝇属,胃蝇属,虱蝇属,厩螯蝇属,狂蝇属,皮蝇属,虻属,螗蜩属,花圆毛蚊,瑞典麦杆蝇,麦花蝇属,菠菜潜叶花蝇,地中海实蝇,油榄实蝇,欧洲大蚊。
蚤目,如印度客蚤和毛列蚤属。
蛛形纲,如蝎和盗蛛。
蜱螨目,如粗脚粉螨,锐缘蜱属,钝缘蜱属,鸡皮刺螨,茶蔗瘿螨,桔芸锈螨,牛蜱属,扁头蜱属,花蜱属,璃眼蜱属,硬蜱属,痒螨属,皮痒螨属,疥螨属,附线螨属,苜蓿苔螨,全爪螨属和叶螨属。
本发明的活性化合物具有突出的高效杀虫和杀螨活性。它们特别成功地用于对付棉红蜘蛛(叶螨属urticae)。另外,该活性化合物特别具有叶面作用的杀虫特性。
根据它们具体的物理和/或化学性质,活性化合物可调制成常规的制剂,如溶液,乳液、悬浮液、粉末、泡沫、糊剂、颗粒、气雾剂、浸泡活性化合物的天然或合成材料,用于种子的在高分子物质和涂料组合物中的细小囊剂,以及在与燃烧设备(如熏蒸筒、熏蒸罐、熏蒸盘管等)一起使用的制剂中的细小囊剂。以及超低容量(VLV)的冷雾(Cold mist)和热雾(Warm mist)制剂。
这些制剂用已知方法制成,例如通过下述方法:活性化合物和稀释剂(即液体溶剂,压力下液化的气体和/或固体载体)任意使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)混合。如果采用水作稀释剂,则也可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);氯化芳族化合物或氯化脂肪烃(如氯苯,氯乙烯或二氯甲烷);脂肪烃(如环己烷或链烷烃,例如矿物油馏分);醇(如丁醇或乙二醇)以及它们的醚和酯;酮(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、二甲基亚砜以及水);所谓液化的气体稀释剂和载体指在环境温度和大气压下为气态的液体(如气溶胶抛射剂,例如卤代烃和丁烷,丙烷和二氧化碳,氮);适用的固体载体有:如研碎的天然矿物(例如高岭土,粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱石或硅藻土)和研碎的合成矿物(如高分散度硅石、三氧化二铝和硅酸盐);适用的颗粒固体载体有: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)及合成的无机颗粒和有机粉,和有机材料颗粒(如锯末、椰壳、玉米棒碎块和烟叶杆);适用的乳化剂和/或起泡剂有:如非离子和阴离子乳化剂(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、芳基磺酸盐及蛋清水解产物);适用的分散剂有:如亚硫酸纸浆废液和甲基纤维素。
在制剂中可采用的粘合剂有:羧甲基纤维素和粉状、颗粒状或胶乳状的天然和合成高分子(如阿拉伯树胶、聚乙烯醇,聚乙酸乙烯酯)以及天然磷脂(如脑磷脂、卵磷脂)和合成磷脂。其它可能的添加剂为矿物油和植物油。
可能采用着色剂,如无机颜料(例如氧化铁、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)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌和盐)。
制剂中一般含有0.1至95%(重量),优选0.5至90%的活性化合物。
本发明的活性化合物用作除草剂时,可直接或以制剂形式,也可与已知除草剂形成混合物使用;用作除草剂时,可能是成品制剂或罐装的混合物。
用于这类混合物的适宜除草剂为下述已知的除草剂:例如N-酰苯胺类,如二氟酚(diflufenican)和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏或毒莠定;芳氧基链烷酸类,如2,4-D(2,4-滴)、2,4-DB(2,4-滴丁酸)、2,4-DP(2,4-滴丙酸)、氟氧吡啶(fluroxpyr)、MCPA(2甲4氯)、MCPP(2甲4氯丙酸)和木草畏(triclopyr);芳氧基-苯氧基链烷酸酯,如禾草灵(diclofop-methyl);乙基酚丙酸(fenoxapropethyl),禾草枯(fulazifop-buryl),甲基海酚丙(haloxyfop-methyl)和2-[4-[6-氯-2-喹喔啉基)氧]苯氧基]丙酸乙酯(quizalofop-ethyl),azinone类,例如5-氨基-4-氯-2-苯基哒嗪-3(2H)-酮(Chloridazon)和哒草灭;氨基甲酸酯类,例如氯苯胺灵、异苯敌、苯敌草和苯胺灵;氯乙酰替苯胺类,例如草不绿、灭草胺、去草胺、甲吡唑安(metazachlor),甲代隆、氯苯胺和毒草胺;二硝基苯胺类,例如黄草消、芽草平和氟乐灵;二苯醚类,例如氟草灭,治草醚,氟糖酚(fluoroglycofen),虎威,halosafen,乳酚(lactofen)和氟草胺;脲类,例如绿麦隆,敌草隆,伏草隆,异丙隆,利谷隆和噻唑隆;羟胺类,例如枯杀达,乙氧定(clethodim)环氧定(cycloxydim),禾莠净和烷氧定(tralkoxydim);咪唑啉酮类,例如咪唑乙畏(imazethapyr),咪唑甲苯(imazamethabenz)咪唑吡啶(imazapyr)和咪唑喹啉(imazaquin);腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如mefenacet磺酰脲类,例如amidosulfuron,甲基苯磺隆(bensulfurob-methyl),乙基氯默隆(chlorimuron-ethyl),阔草脲,cinosulfuron,甲基甲磺隆(metoulfuron-methyl),nicosulfuron,primisulfuron,乙基吡唑杀隆(pyrazosulfuron-ethyl),甲基西酚杀隆(thifensulfuron-methyl),三硫隆(triasulfuron)和甲三苯隆(tribenuron-methyl);硫代氨基甲酸酯类,例如苏灭达,草灭特,燕麦敌,扑草灭,esprocarb,草达灭,扑硫威(prosulphocayb),杀草丹和野麦畏;三嗪类,例如阿特拉津,草净津,西玛津,西草净,去草净和特丁津(terbuthylazin e);三嗪酮类,例如敌草灵(hexazinone),灭它通(metamitron)和赛克津;及其它除草剂,例如氨基三唑,benfuresate,噻草平,辛甲灵(cinmethylin),氯马腙(clomazone),氯吡啶(clopyralid),燕麦清(difenzoquat),dithiopyr,草定完,卤吡咯酮(fluorochloridone),glufosinate,草甘膦,异恶苯(isoxaben),草利达(pyridate),quinchlorac,quinmerac,sulphosate和2-(3,5-二氯(苯基)-2-(2,2,2-三氯乙基)环氧乙烷(tridiphane)。
与其它已知活性化合物如杀真菌剂,杀虫剂,杀螨剂、杀线虫剂、驱鸟剂、植物营养剂及土壤结构改良剂的混合物也可以使用。
用作除草剂时,这些活性化合物可以原药形式、其制剂形式、或通过进一步稀释例如可直接使用的溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂而制备的使用形式加以使用。它们是以浇水、喷雾、雾化或喷洒等习用方式使用的。
用作除草剂时,本发明的活性化合物既可以在植物发芽前也可在植物发芽后施用。
它们也可以在播种前混入土壤中。
用作除草剂时,活性化合物的用量可以在一个很大的范围内变化。这基本上取决于所需效果的性质。一般地说,用量是每公顷土壤表面为0.01-10千克活性化合物,优选0.05-5千克/公顷。
本发明的活性化合物用作杀虫剂和杀螨剂时,也可存在于市售制剂中和存在于由这些制剂制得的使用形式中,如和其它活性化合物(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂)的混合物。这些杀虫剂包括,例如,磷酸盐、氨基甲酸酯、羧化物、氯代烃、苯脲和微生物产出的物质。
本发明的活性化合物用作杀虫剂和杀螨剂时,还可存在于市售制剂和由这些制剂制得的使用形式中,如和增效剂的混合物。增效剂为强化活性化合物作用的化合物。而加入的增效剂本身不一定是活性的。
由市售制剂制得的使用形式中的活性化合物的含量在一个很宽的限度内变化。活性化合物在使用形式中的浓度为0.0000001%至95%(重量)活性化合物,优选0.0001%至1%(重量)。
本化合物用作杀虫剂和杀螨剂时,以适于使用形式的常用方法进行使用。
本发明的活性化合物的制备和用途可从后述实施例中看出。
制备实施例
实施例1:
方法(a)
在室温下,5.3克(0.038摩尔)碳酸钾加入到5.3克(0.032摩尔)4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮(例如参照US3,780,052)和5.5克(0.032摩尔)5-氯-2,4-二氟苄腈的100毫升二甲基亚砜溶液中,混合液接着在100℃加热36小时。进行如下处理,冷却的反应混合液倒入水中,用稀盐酸把pH调至2,用二氯甲烷萃取混合液数次。合并有机相,用硫酸钠干燥并真空浓缩。残留物在硅胶上进行色谱分离(洗出液:二氯甲烷)。
获得1.8克(理论值的18%)熔点为105℃的1-(2-氯-4-氰基-5-氟苯基)-4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮。
实施例2:
方法(b)
在室温下,0.6克(0.014摩尔)的氢化钠(60%的矿物油溶液)在搅拌条件下加入到1.0克(0.014摩尔)的3-丁炔-2-醇的50毫升乙腈溶液中,在室温下搅拌混合液15分钟,然后加入2.9克(0.01摩尔)的1-(2,5-二氟-4-氰基苯基)-4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮,接着再在室温下搅拌混合液2小时。进行如下处理,反应混合液在真空中浓缩,残留物在二氯甲烷和水之间分配,有机相用硫酸钠干燥并在真空中由溶剂中分出。
得到1.8克(理论值的54%)熔点为41℃的1-[2-氟-4-氰基-5-(3-(1-丁炔基)-氧基)苯基]-4-甲基-3-三氟甲基-1,2,4-三唑啉-5-酮。
实施例3:
方法(c)
在室温下,1.7克(0.012摩尔)碳酸钾加入到1.7克(0.01摩尔)4-氨基-3-三氟甲基-1,2,4-三唑啉-5-酮和1.6克(0.01摩尔)2,4,5-三氟苄腈(例如,参照EP191,181)的30毫升二甲基亚砜溶液中,室温下,再继续搅拌混合液14小时。进行如下处理,反应混合物转移到水中,用稀盐酸把pH值调至2,并用二氯甲烷萃取混合液数次。合并有机相,用硫酸钠干燥,并在真空中浓缩,残留物和水一起搅拌,空吸过滤并干燥。
得到2.6克(理论值的87%)熔点为141℃的1-(2,5-二氟-4-氰基苯基)-4-氨基-3-三氟甲基-1,2,4-三唑啉-5-酮。
实施例4
方法(c)
在-5℃至0℃温度下,在15分钟时间内把1.4克(0.02摩尔)亚硝酸钠的饱和水溶液在搅拌下加到3.0克(0.01摩尔)1-(2,5-二氟-4-氰基苯基)-4-氨基-3-三氟甲基-1,2,4-三唑啉-5-酮的40毫升10%盐酸溶液中,接着撤掉冷却浴,在室温下搅拌混合液1小时,然后再冷却到-5℃至0℃温度并过滤,残留物用水洗涤并干燥。
得到1.8克(理论值的62%)熔点为51℃的1-(2,5-二氟-4-氰基苯基)-3-三氟甲基-1,2,4-三唑啉-5-酮。
实施例5
方法(d)
在0℃至10℃温度下,在5小时过程中,把15克(0.17摩尔)氯二氟甲烷加到2.5克(0.009摩尔)1-(2,5-二氟-4-氰基苯基)-3-三氟甲基-4H-1,2,4-三唑啉-5-酮,1.0克(0.017摩尔)氢氧化钾和0.25克溴化四丁基铵在50毫升四氢呋喃的悬浮液中,并在此期间的1,2和3小时各补加1.0克(0.017摩尔)氢氧化钾用用于补充消耗的碱。处理时,反应混合液倒入水中,然后用乙酸乙酯萃取数次,合并有机相,用硫酸钠干燥,在真空条件下除去溶剂。残留物在硅胶上进行色谱分离(洗出液:二氯甲烷)。
得到2.2克(理论值的75%)熔点为68℃的1-(2,5-二氟-4-氰基苯基)-3-三氟甲基-4-二氟甲基-1,2,4-三唑啉-5-酮。
起始化合物的制备
实施例Ⅱ-1
在搅拌和用冰进行冷却条件下,将2782克(13摩尔)碳酸二苯酯在2小时过程中分批加到1300克(26摩尔)水合肼中,加入过程中反应混合液温度不要高于30℃,接着混合液在80℃搅拌2小时,然后再冷却,并分批加入总计为3164克(26摩尔)的三氟乙酸。混合液在80℃再搅拌2小时,接着蒸出水直至残留物达到180℃,冷却后,加入1100克(16.2摩尔)氨水(25%浓度),在回流温度下加热混合液3小时。进行如下处理,在逐渐降低的压力下(直至20毫巴)蒸出所有挥发成分直至残留物达到180℃,残留物由2000毫升水中重结晶,空吸过滤并干燥。
得到702克(理论值的32%)熔点为163℃的3-三氟甲基-4-氨基-1H-1,2,4-三唑啉-5-酮。
实施例Ⅲ-1
在室温和搅拌下,220克(1.06摩尔)2,4,5-三氯苄腈(参照EP441,004)加入到250克(4.31摩尔)氟化钾在400毫升蒸馏的四氢噻吩砜的溶液中,接着在195℃至200℃间搅拌混合液10小时。处理时,冷却混合液,加入500毫升水,对混合液进行蒸汽蒸馏。有机相溶于二氯甲烷,混合液用硫酸钠干燥,并在真空中浓缩,然后蒸馏。
得到108克(理论值的58%)熔点48-50℃,在30毫巴时沸点为105~107℃的2,4-二氟-5-氯苄腈。
下面通式(Ⅰ)的取代的三唑啉酮以相应的方式,并按照制备的一般知识获得:
6
F CN F1H NMR*):
1.45-1.55;
4.22-4.3;
7.58-7.62
9 Cl CN H m.p.108℃
10 F CN H m.p.96℃
11 F CN F m.p.103℃
12 F CN CH3-O- m.p.56℃
13 H CN F m.p.82℃
14 H CN F m.p.125℃
15 F CN CH3-O- m.p.131℃
16 H CN
m.p.190℃
17 H CN CH3-O- m.p.215℃
18 H CN CH3-O- m.p.187℃
19 F CN C2H5-O- m.p.126℃
20 H CN F m.p.130℃
实施例编号
R3R4R5物理性质
22 F CN F m.p.68℃
23 Cl CN H m.p.145℃
24 F CN H m.p.204℃
1.75-1.78;2.6;
3.9-4.0
26 F CN CH3-O- m.p.133-135℃
27 F CN -NH-CH3m.p.143℃
28 F CN F m.p.148℃
29 F CN F m.p.74℃
31 F CN F1H NMR*):
1.38-1.5;
1.73-1.83;
3.82-3.88
32 F CN F m.p.177℃
实施例编号
R3R4R5物理性质
34
F CN -(O-CH2-CH2)2-OCH3 1H NMR*):
3.48;
3.55-3.6;
3.9-3.97
35
F CN -O-C2H5 1H NMR*):
1.4-1.46;1.5-
1.55;3.9-3.98;
4.14-4.2
3.9-3.98;4.6-
4.68;7.2-7.23;
7.42-7.45
1.72-1.8;
3.8-3.87;
7.45-7.5
38 F CN F m.p.90℃
39 F NO2F m.p.99℃
40 F CN
m.p.95℃
1.75-1.8;2.08-
2.18;3.85-3.92;
7.03-7.18
1.75-1.8;4.33-
4.42;4.9-4.98;
7.45-7.5
43 F CN -O-CH2-Si(CH3)3m.p.101℃
44 F CN -O-CH2-CH=CH2m.p.76℃
1.18-1.22;1.4-
1.45;3.8-3.85;
4.22-4.25
1.85;3.9-
3.98;4.15-
4.2;7.2-7.23
3.4;
3.9-3.98;
7.1-7.13;
7.38-7.42
50
F CN -N(CH3)2 1H NMR*):
3.17;3.9-3.98;
7.1-7.13;
7.38-7.42
1.75-1.8;3.9-
3.98;4.9-5.0;
7.35;7.75
实施例编号
R3R4R5物理性质
53 F CN -O-n-C3H7m.p.71℃
54 F CN -O-CH2-C≡CH1H NMR*):
2.53;3.9-3.98;
4.85;7.4-7.42
2.67-2.78;3.9-
3.98;4.22-4.3;
7.23-7.25
56
Cl CN Cl m.p.97℃
实施例编号
R3R4R5物理性质
1.45-1.65;3.9-
3.98;3.95-4.05;
7.25-7.28
59 F CN -S-C2H5 1H NMR*):
3.05-3.1;3.9-
3.98;7.5-7.55;
7.67-7.7
60 F CN F1H NMR*):
4.48-4.5;5.35-
5.4;5.87-5.97;
7.5-7.56
*)1H NMR谱在以四甲基甲硅烷(TMS)为内标的氘氯仿中记录。所给数据代表以δ值(ppm)计的化学位移。
用途实施例:
在下述用途实施例中,下列化合物用作比较物质:
3-甲基-4-炔丙基-1-(2,5-二氟-4-氰基苯基)-1,2,4-三唑啉-5-酮。
3,4-二甲基-1-(3-氟-4-氰基苯基)-1,2,4-三唑啉-5-酮(二者均在DE3,839,480中公开)。
实施例A
杂草出现前处理试验
溶液:5份重量的丙酮
乳化剂:1份重量的烷基芳基聚乙二醇醚
制活性化合物的一种适用预制剂时,一份重量的活性化合物和上述量的溶剂混合,再加入上述量的乳化剂,并用水稀释至所需浓度。
实验植物的种子播种到一般土壤中,24小时后,用活性化合物的预制剂浇灌。维持单位面积的水量相同较为有利。预制剂中活性化合物的浓度不重要,关键的是施到单位面积上的活性化合物的量。三星期之后,通过与未经处理的对照样植物生长情况比较来评估对所试植物的损害程度(以%表示)
数据表示:
0%=无作用(如未加处理的对照样)
100%=完全消灭
比较实施例(A)在使用量为250克/公顷时对杂草(如狗尾
草属、苋属、牛藤菊属,藜属,母菊属,茄属和堇菜属)无活性,而在本试验中,用此使用量,用制备实施例7,9,17和29的化合物可得到40%至100%的活性,用制备实施例10、11、12、15和19的化合物可得到95%至100%的活性。
实施例B
叶螨试验(抗OP)
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷基芳基聚乙二醇醚
制备活性化合物的一种适用预制剂时,1份重量的活性化合物和所述量的溶剂以及所述量的乳化剂混合,用水稀释该浓液至所需浓度。
受到各种发育阶段的二点叶螨(叶螨属urticae)严重侵害的豆类植物(普通云扁豆)浸入一种所需浓度的活性化合物预制剂中。
经过一定时间后,确定死亡率(以%计)。100%表示所有叶螨被杀死,0%表示没有叶螨被杀死。
在本实验中,发现明显优于实施例(B)(在现有技术中已知)的杀螨活性,例如,用制备实施例13的化合物。
实施例C
猿叶虫-试验
溶剂:31份重量的丙酮
乳化剂:1份重量的烷基芳基聚乙二醇醚
制备活性化合物的一种适用预制剂时,1份重量的活性化合物和所述量的溶剂混合,加入所述量的乳化剂,该浓液用水稀释至所需浓度。
卷心菜叶子用该适用的活性化合物预制剂处理,这样处理过的叶
子和两只发育阶段的辣根猿叶虫一起放到一个塑料盒中。3天后加入一片未处理的叶子。在指定时间后,确定死亡率(以%计)。100%表示全部辣根猿叶虫都被杀死;0%表示无辣根猿叶虫被杀死。
在本实验中,发现明显优于现有技术的杀螨活性,例如用化合物20和62。
实施例D
瘤蚜-实验
溶剂:31份重量的丙酮
乳化剂:1份重量的烷基芳基聚乙二醇醚
制备活性化合物的一种适用预制剂时,1份重量的活性化合物和所述量的溶剂混合,加入所述量的乳化剂,该浓液用水稀释至所需浓度。
用适当浓度的活性化合物预制剂处理受桃蚜侵害的蚕虫蚜,并将它放入塑料盒中。
指定时间后,确定死亡率(以%计)。100%表示所有桃蚜被杀死;0%表示无桃蚜被杀死。
在本实验中,发现用实施例57和62的化合物可得到明显优于现有技术的杀螨活性。
Claims (14)
1、通式(Ⅰ)的新的取代的三唑啉酮,其中
R1代表卤代烷基,
R2代表氢、氨基、氰基、烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基、亚烷基亚氨基或任意取代的环烷基或环烷基烷基;
R3代表氢或卤素;
R4代表氰基或硝基;
R5代表硝基、氰基、氢、杂环基烷氧基,下式的基团:R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7),或下式的基团
R6,-O-R6、-S-R6、-S(O)-R6,-SO2-R6,-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7)或下式的基团:
且
X代表氧或硫;其中
R 6 和R 7 各自独立地代表氢或含1到8个碳原子、并任意被相同或不同取代基单取代或多取代的直链或支链烷基,适宜的取代基为:
卤素(特别是氟、氯、溴和/或碘),氰基,羧基,氨基甲酰基,直链或支链的烷氧基、烷氧基烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氧基羰基、烷氧基羰基烷基、N-烷基氨基羰基、环烷基氨基羰基、N,N-二烷基氨基羰基、三烷基甲硅烷基或烷基磺酰基氨基羰基,它们在各自的单个烷基部分有1至8个碳原子;或含1至3个相同或不同杂原子(特别是氮、氧和/或硫)的5元至7元的、任意苯并的饱和或不饱和杂环基;
R 6 和R 7 还代表2至8个碳原子的,任意被相同或不同卤素取代基(特别是氟、氯、溴和/或碘)单取代或多取
且
X代表氧或硫,其中
R6和R7各自独立地代表氢或任意取代的直链或支链烷基、链烯基、链炔基、环烷基、环烷基烷基、芳烷基或芳基。
2、按权利要求1的通式(Ⅰ)的取代三唑啉酮,其特征在于:
R1代表含1至6个碳原子和1至13个相同或不同卤素原子,(特别是氟、氯、溴或碘)的直链或支链卤代烷基;
R2代表氢,氨基,氰基,含1至8个碳原子的直链或支链烷基,含2至6个碳原子的直链或支链链烯基或链炔基,含1至6个碳原子和1至13个相同或不同卤素原子(特别是氟、氯、溴或碘)的直链或支链卤代烷基,含2至6个碳原子和1至11个相同或不同卤素原子(特别是氟、氯、溴或碘)的直链或支链卤代链烯基或卤代链炔基,各个烷基部分含1至4个碳原子的直链或支链烷氧基烷基,含1至8个碳原子的直链或支链亚烷基亚氨基,或在环烷基部分含有3至8个碳原子、适宜时在直链或支链亚烷基部分含有1至4个碳原子的环烷基或环烷基烷基,它们各自在环烷基部分任意被相同或不同的卤素取代基(特别是氟、氯、溴和/或碘)单取代或多取代;
R3代表氢、氟、氯、溴或碘;
R4代表氰基或硝基;
R5代表硝基,氰基,氟,氯,溴,碘或杂环基-C1-C4-烷氧基,含1至3个杂原子(特别是氮、氧和/或硫)的3至7元的任意苯并的饱和或不饱和的杂环基,或下式的基团:代的链烯基或链炔基;
R6和R7还代表3至7个碳原子、被相同或不同卤素取代基(特别是氟、氯、溴和/或碘)和/或被含1至4个碳原子的直链或支链烷基任意单取代或多取代的环烷基或代表C3-C7-环烷基-C1-C3-烷基,或
R6和R7还代表芳烷基或芳基,它们各自的芳基部分含6至10个碳原子,适宜时,在直链或支链烷基部分含1至4个碳原子,所述芳烷基和芳基的芳基部分被相同或不同的取代基任意单取代或多取代,适宜的芳基的取代基为:
卤素,氰基,硝基,含1至6个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚碘酰基或烷基磺酰基,含1至6个碳原子和1至13个相同或不同卤素原子的直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,各自的单个烷基部分含1至6个碳原子的直链或支链烷氧基羰基或烷氧基亚氨基烷基,和被相同或不同的卤素取代基和/或被含1至6个碳原子的直链或支链烷基或烷氧基和/或被含1至6个碳原子和1至13个相同或不同卤素原子的直链或支链卤代烷基或卤代烷氧基任意单取代或多取代的苯基。
3、按权利要求1的通式(Ⅰ)的取代的三唑啉酮,其特征在于:
R1代表含1至4个碳原子的1至9个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代烷基;
R2代表氢,氨基,氰基,含1至6个碳原子的直链或支链烷基,含2至4个碳原子的直链或支链链烯基或链炔基,含1至4个碳原子和1至9个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代烷基,含2至4个碳原子和1至7个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代链烯基或卤代链炔基,各自单个烷基部分含1至3个碳原子的直链或支链烷氧基烷基,含1至6个碳原子的直链或支链亚烷基亚氨基,或环烷基部分含3至7个碳原子,并在适宜时在直链或支链烷基部分含1至3个碳原子的环烷基或环烷基烷基,所述基团的环烷基部分被相同或不同的卤素取代基(特别是氟、氯和/或溴)任意单取代至四取代;
R3代表氢、氟、氯或溴;
R4代表氰基或硝基;
R5代表硝基、氰基、氟、氯,溴或杂环基-C1-C3-烷氧基,其中杂环基为含1至3个相同或不同杂原子(特别是氮、氧和/或硫)的4或6元的饱和或不饱和杂环基团,或下述基团:R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)-(OR6)(OR7)或下式的基团:
且
X代表氧或硫;其中
R6和R7各自独立地代表氢或含1至6个碳原子任意单取代的直链或支链烷基,适宜的取代基如下:
氰基,羧基,氨基甲酰基,各自单个烷基部分含1至6个碳原子的直链或支链烷氧基、烷氧基烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷氧基羰基、烷氧基羰基烷基,N-烷基氨基羰基、N,N-二烷基氨基羰基、三烷基甲硅烷基或烷基磺酰基氨基羰基,含1至3个相同或不同杂原子(特别是氮、氧和/或硫)的5元或6元的饱和或不饱和的杂环基;
R6和R7还代表含有1至4个碳原子和1至9个相同或不同的卤素原子(特别是氟、氯或溴)并进一步被C1-2烷氧基羰基、C1-5环烷基氨基羰基或氰基任意取代的直链或支链卤代烷基;
R6和R7还代表含2至6个碳原子并被相同或不同卤素取代基(特别是氟、氯或溴)任意单取代至三取代的链烯基或链炔基;
R6和R7还代表含3至6个碳原子,被相同或不同的卤素取代基(特别是氟、氯或溴)和/或被含1至3个碳原子的直链或支链烷基任意单取代至四取代的环烷基,或代表C3-5-环烷基-C1-2-烷基,或代表苯基烷基或苯基(前者的直链或支链烷基部分含1至3个碳原子),所述基团的苯基部分被相同或不相同的取代基任意单取代至三取代,适宜的苯的取代基为:
卤素,氰基,硝基,含1至4个碳原子的直链或支链烷基、烷氧基、烷硫基、烷基亚碘酰基或烷基碘酰基,含1至4个碳原子和1至9个相同或不同卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚碘酰基或卤代烷基磺酰基,各自烷基部分含1至4个碳原子的直链或支链烷氧基羰基或烷氧基亚氨基烷基,以及被相同或不同的卤素取代基和/或被含1至4个碳原子的直链或支链烷基或烷氧基和/或被含1至4个碳原子和1至9个相同或不同卤素原子的直链或支链卤代烷基或卤代烷氧基任意单取代或多取代的苯基。
4、制备通式(Ⅰ)的新的取代的三唑啉酮的方法,
其中:
R1代表卤代烷基,
R2代表氢、氨基、氰基、烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基、亚烷基亚氨基、或任意取代的环烷基或环烷基烷基;
R3代表氢或卤素;
R4代表氰基或硝基;
R5代表硝基、氰基、卤素、杂环基烷氧基,或下述的基团
R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,
-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,
-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)(OR6)(OR7),
或下式的基团
且
X代表氧或硫,其中
R6和R7各自独立地代表氢或任意取代的直链或支链烷基、链烯基、链炔基、环烷基、环烷基烷基、芳烷基或芳基。
所述方法的特征在于:
a)适宜时,在稀释剂和反应助剂存在下,式(Ⅱ)的1H-三唑啉酮和式(Ⅲ)的卤代苯衍生物反应:
其中:
R1,R2和X具有前述意义。
其中:
R3、R4和R5具有前述意义,Hal代表卤素。
或在于:
b)适宜时,在稀释剂和反应助剂存在下,式(Ⅰa)的取代的三唑啉酮和式(Ⅳ)的亲核试剂反应:
其中:
R1、R2、R3、R4和X具有前述意义,且
R5-1代表卤素;
R6-1-Z-H (Ⅳ)
个碳原子和1至9个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代烷基,含2至4个碳原子和1至7个相同或不同卤素原子(特别是氟、氯或溴)的直链或支链卤代链烯基或卤代链炔基,在单个烷基部分有1至3个碳原子的直链或支链烷氧基烷基,含1至6个碳原子的直链或支链亚烷基亚氨基,或者环烷基或环烷基烷基,其中在环烷基部分含3至7个碳原子,适宜时,直链或支链烷基部分含1至3个碳原子,各自的环烷基部分可任意被相同或不同的卤素取代基(特别是氟、氯和/或溴)单取代至四取代;
R3代表氢、氟、氯或溴;
R4代表氰基或硝基;
R5代表硝基、氰基、氟、氯、溴或杂环基-C1-C3-烷氧基(杂环基团为4或6元的饱和或不饱和的,含1至3个相同或不同的杂原子,特别是氮、氧和/或硫的杂环),或下式的基团:R6,-O-R6,-S-R6,-S(O)-R6,-SO2-R6,-SO2-O-R6,-O-SO2-R6,-C(O)-O-R6,-NR6R7,-SO2-NR6R7,-C(O)-NR6R7,-NH-P(O)(OR6)(R7)或-NH-P(O)-(OR6)(OR7)或下式的基团:
X代表氧或硫;其中
R6和R7各自独立地代表氢或含1至6个碳原子并任意单取代
其中:
R1、R3、R4、R5和X具有前述意义,且
R2-2代表氢;
R2-3-E (Ⅴ)
其中:
R2-3代表烷基、链烯基、链炔基、卤代烷基、卤代链烯基、卤代链炔基、烷氧基烷基或任意取代的环烷基,且
E代表吸电子离去基团。
5、对付不需要的植物的方法,其特征在于使按权利要求1至4的通式(Ⅰ)的取代的三唑啉酮作用于植物和/或它们的环境。
6、按权利要求1至4的通式(Ⅰ)的取代的三唑啉酮对付不需要的植物的用途。
7、制备除莠剂和杀螨剂的方法,其特征在于按权利要求1至4的通式(Ⅰ)的取代的三唑啉酮和稀释剂和/或表面活性剂混合。
8、对付蜘蛛的方法,其特征在于使按权利要求1至4的通式(Ⅰ)的取代的三唑啉酮作用于蜘蛛和/或它们的环境。
9、按权利要求1至4的通式(Ⅰ)的取代的三唑啉酮对付蜘蛛的用途。
10、4-氨基-3-三氟甲基-1H-1,2,4-三唑啉-5-酮。
11、2,4-二氟-5-氯苄腈
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DE3839480A1 (de) * | 1988-11-23 | 1990-05-31 | Bayer Ag | N-aryl-stickstoffheterocyclen, verfahren sowie neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren |
US4980480A (en) * | 1989-09-08 | 1990-12-25 | Fmc Corporation | Production of triazolinones |
IE72169B1 (en) * | 1989-11-17 | 1997-03-26 | Asahi Glass Co Ltd | Processes for producing 5-fluorobenzoic acids and their intermediates |
IT1238084B (it) * | 1990-02-07 | 1993-07-05 | Enichem Sintesi | Procedimento per la preparazione di nitrili aromatici |
JPH04321644A (ja) * | 1991-04-17 | 1992-11-11 | Asahi Glass Co Ltd | 2,4,5−トリフルオロ安息香酸の製造方法 |
-
1992
- 1992-11-12 DE DE4238125A patent/DE4238125A1/de not_active Withdrawn
-
1993
- 1993-10-19 TW TW082108655A patent/TWI230035B/zh not_active IP Right Cessation
- 1993-11-02 EP EP93117748A patent/EP0597360B1/de not_active Expired - Lifetime
- 1993-11-02 DK DK93117748T patent/DK0597360T3/da active
- 1993-11-02 DE DE59310225T patent/DE59310225D1/de not_active Expired - Fee Related
- 1993-11-02 ES ES93117748T patent/ES2165846T3/es not_active Expired - Lifetime
- 1993-11-09 CA CA002102750A patent/CA2102750C/en not_active Expired - Fee Related
- 1993-11-09 KR KR1019930023730A patent/KR100314350B1/ko not_active IP Right Cessation
- 1993-11-10 JP JP30330193A patent/JP3621122B2/ja not_active Expired - Fee Related
- 1993-11-11 BR BR9304702A patent/BR9304702A/pt not_active IP Right Cessation
- 1993-11-12 CN CN93114409A patent/CN1036994C/zh not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110072853A (zh) * | 2016-12-16 | 2019-07-30 | 巴斯夫欧洲公司 | 除草的苯基三唑啉酮类 |
CN110072853B (zh) * | 2016-12-16 | 2023-07-25 | 巴斯夫欧洲公司 | 除草的苯基三唑啉酮类 |
Also Published As
Publication number | Publication date |
---|---|
ES2165846T3 (es) | 2002-04-01 |
DK0597360T3 (da) | 2002-02-11 |
JP3621122B2 (ja) | 2005-02-16 |
KR940011454A (ko) | 1994-06-21 |
BR9304702A (pt) | 1994-05-17 |
EP0597360A1 (de) | 1994-05-18 |
TWI230035B (en) | 2005-04-01 |
JPH0776578A (ja) | 1995-03-20 |
CA2102750A1 (en) | 1994-05-13 |
EP0597360B1 (de) | 2001-10-17 |
KR100314350B1 (ko) | 2002-02-28 |
DE59310225D1 (de) | 2001-11-22 |
CA2102750C (en) | 2005-03-29 |
CN1036994C (zh) | 1998-01-14 |
DE4238125A1 (de) | 1994-05-19 |
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