CN1150421A - 取代的三唑啉酮及其作为除草剂的用途 - Google Patents
取代的三唑啉酮及其作为除草剂的用途 Download PDFInfo
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- CN1150421A CN1150421A CN95191743A CN95191743A CN1150421A CN 1150421 A CN1150421 A CN 1150421A CN 95191743 A CN95191743 A CN 95191743A CN 95191743 A CN95191743 A CN 95191743A CN 1150421 A CN1150421 A CN 1150421A
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- alkyl
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- 239000004009 herbicide Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005864 Sulphur Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- 150000001721 carbon Chemical group 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- -1 triazole quinoline ketone Chemical class 0.000 claims description 57
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 239000011737 fluorine Substances 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 47
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 46
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000003368 amide group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000005001 aminoaryl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 4
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- MJYGPNBYCMSMFL-UHFFFAOYSA-N [O].C1CCOC1 Chemical compound [O].C1CCOC1 MJYGPNBYCMSMFL-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- OYGQPOAFJKEAFN-UHFFFAOYSA-N [O].C1CCOCC1 Chemical compound [O].C1CCOCC1 OYGQPOAFJKEAFN-UHFFFAOYSA-N 0.000 claims 2
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 43
- 239000002585 base Substances 0.000 description 31
- 239000000126 substance Substances 0.000 description 29
- 235000017168 chlorine Nutrition 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
具有通式(I)的新的取代三唑啉酮，其中Q代表氧或硫，R1代表卤代烷基，R3代表氢或卤素，R4代表氰基或硝基，R2代表氢或各种取代基，R5代表各种取代基。还公开了制备这些三唑啉酮的方法以及它们作为除草剂的用途。
Description
本发明涉及新的取代三唑啉酮，它们的制备方法以及作为除草剂的用途。
有些取代三唑啉酮已经公开，如化合物2-(4-氰基-2，5-二氟-苯基)-5-甲基-4-炔丙基-2，4-二氢-3H-1，2，4-三唑-3-酮，具有除草性质(参见EP-A370332)。
然而，这些已知化合物不能在所有方面满足要求。
现在发现了具有通式I的新的取代三唑啉酮，
其中：Q代表氧或硫，R1代表卤代烷基，R2代表氢，氨基，氰基，烷基，烯基，炔基，卤代烷基，卤代烯基，卤代炔基，烷氧基烷基，亚烷基亚氨基，或各种情况下任意被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，及R5代表异氰基，氰硫基，磺基，卤代磺酰基，烷基氨基氧基，二烷基氨基氧基，亚烷基氨基氧基，亚环烷基氨基氧基，或各种情况下被任意取代的环烯基氧基或杂环基氧基，或下列通过氮或氧键合的基团之一：-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，其中：R6代表氢，或代表烷基，烯基或炔基，其中每一个可任意被卤素取代，或代表-CO-R13，其中：
R13代表氢，或代表烷基或烷氧基，它们可以任意被卤素或烷氧
基取代，或代表氨基，烷基氨基或二烷基氨基，或代表任意被取
代的环烷基，环烷基烷基，芳基，芳烷基或杂环基烷基，R7代表-(CO)n-R13基团，其中：
R13如上定义，
n代表数字1或2，R8代表氢，烷基或烷氧基，R9代表烷氧基，烷基氨基或二烷基氨基，R10代表任意被卤素取代的烷基，或代表烷氧基，或代表烷基氨基，或代表二烷基氨基或代表任意取代的芳基，R11代表任意被卤素取代的烷基或环烷基，或各种任意取代的芳基或杂环基，及R12代表烷基。而且发现，通式(I)的新的取代三唑啉酮可通过下列反应得到：(a)通式(II)氨基芳基三唑啉酮
其中，Q，R1，R2，R3，R4和R6定义如上，与通式(III)的酰卤反应，
X1-(CO)n-R13 (III)其中，n和R13定义如上，X1代表卤素，或与通式(IV)的原酸酯反应，
R8-C(OR9)3 (IV)，其中，R8和9定义如上，如果需要，在反应助剂和稀释剂存在下进行，或(b)通式(V)羟基芳基三唑啉酮
其中，Q，R1，R2，R3和R4定义如上，与通式(VI)的酰卤反应，
X2-CO-R10 (VI)其中，R10定义如上，X2代表卤素，如果需要，在酸受体和稀释剂存在下进行，或(c)通式(VII)卤代芳基三唑啉酮
其中，Q，R1，R2，R3和R4定义如上，X3代表卤素，
与通式(VIII)的羟基烷基膦酸酯反应，
HO-CHR11-P(O)(OR12)2 (VIII)
其中，R11和R12定义如上，
如果需要，在酸受体和稀释剂存在下进行。
我们发现，通式(I)新的取代三唑啉酮具有令人感兴趣的除草性质。
惊奇的是，本发明通式(I)的取代三唑啉酮比现有技术中已知的取代三唑啉酮，如化合物2-(4-氰基-2，5-二氟-苯基)-5-甲基-4-炔丙基-2，4-二氢-3H-1，2，4-三唑-3-酮，有更好的除草活性。
本发明优选的式(I)化合物为其中
Q代表氧或硫，R1 代表有1-6个碳原子和1-13个相同或不同卤原子，尤其是氟，
氯，溴或碘的直链或支链卤代烷基，R2 代表氢，氨基，氰基，有1-8个碳原子的直链或支链烷基，有2
-6个碳原子的直链或支链烯基或炔基，有1-6个碳原子和1
-13个相同或不同卤原子，尤其是氟，氯，溴或碘的直链或支链
卤代烷基，或代表有2-6个碳原子和1-11个相同或不同卤原
子，尤其是氟，氯，溴或碘的直链或支链卤代烯基或卤代炔基，
或代表在各烷基部分有1-4个碳原子的直链或支链烷氧基烷
基，或代表有1-8个碳原子的直链或支链亚烷基亚氨基，或代
表在各环烷基部分有3-8个碳原子的环烷基或环烷基烷基，而
且如果可能，在直链或支链烷基部分有1-4个碳原子，并在环
烷基部分被相同或不同的卤素取代基，尤其是氟，氯，溴和/或碘
单一的或多重的取代，R3 代表氢，氟，氯，溴或碘，R4 代表氰基或硝基，及R5 代表异氰基，氰硫基，磺基，卤代磺酰基，C1-C6-烷基氨基氧基，
二(C1-C4-烷基)-氨基氧基，C1-C6-亚烷基氨基氧基或C5-C6-亚
环烷基氨基氧基，或任意被卤素，C1-C4-烷基或C1-C4-烷氧基取代
的C5-C6-环烯基氧基，全氢化呋喃基氧基，或全氢化吡喃基氧基，
或代表通过氮或氧键合的下列基团之一：
-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，
其中：
R6 代表氢，或代表烷基，烯基或燥基，其中每个基团具有至多
6个碳原子并任意被氟和/或氯取代，或代表-CO-R13，
其中：
R13 代表氢，或代表烷基或烷氧基，它们具有1-6个碳原
子，并且可以任意被氟，氯或C1-C4-烷氧基取代，或代
表氨基，或代表在烷基部分有1-6个碳原子的烷基
氨基或二烷基氨基，或代表任意被取代的C3-C6-环烷
基，C3-C6-环烷基C1-C4-烷基，苯基，萘基，苯基-
C1-C4-烷基，呋喃基，噻吩基或吡啶基，适当的取代基
包括：
卤素，氰基，硝基，有1-4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，
有1-4个碳原子且有1-9个相同或不同卤原子的
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，在各烷基部分有
1-4个碳原子的直链或支链烷氧羧基或烷氧基亚氨基
烷基，以及任意被相同或不同的取代基单取代或多取
代的苯基，这些取代基包括卤素和/或有1-4个碳原
子的直链或支链烷基或烷氧基，和/或有1-4个碳原
子和1-9个相同或不同卤原子的直链或支链卤代烷
基或卤代烷氧基；R7代表-(CO)n-R13基团，其中：
R13 具有上面定义且作为优选，
n 代表数字1或2，R8 代表氢，或代表有1-6个碳原子的烷基或烷氧基，R9 代表烷基部分有1-6个碳原子的烷氧基，烷基氨基或二烷
基氨基，R10 代表任意被氟和/或氯取代的有1-6个碳原子的烷基，或
代表在烷基部分有1-6个碳原子的烷氧基或烷基氨基或
二烷基氨基，或代表任意取代的苯基，在上述R6中的那些
作为优选的苯基取代基，在这里也可以作为优选考虑，R11 代表任意被氟和/或氯取代的有1-6个碳原子的烷基或有3
-6个碳原子的环烷基，或任意取代的苯基，萘基，呋喃
基，噻吩基或吡啶基，在上述R6中作为优选的那些苯基取
代基在这里也可以作为优选考虑，R12 代表有1-6个碳原子的烷基。本发明特别优选的式(I)化合物为：Q 代表氧或硫，R1 代表有1-4个碳原子和1-9个相同或不同卤原子，尤其是氟，
氯，溴或碘的直链或支链卤代烷基，R2 代表氢，氨基，氰基，有1-4个碳原子的直链或支链烷基，有3
-4个碳原子的直链或支链烯基或炔基，有1-4个碳原子和1
-9个相同或不同卤原子，尤其是氟或氯的直链或支链卤代烷基，
有3-4个碳原子和1-5个相同或不同卤原子，尤其是氟或氯
的直链或支链卤代烯基或卤代炔基，或代表在各烷基部分有1-3
个碳原子的直链或支链烷氧基烷基，或代表有1-4个碳原子的
直链或支链亚烷基亚氨基，或代表在各环烷基部分有3-6个碳
原子的环烷基或环烷基烷基，而且如果可能，在直链或支链烷基
部分有1-3个碳原子，并在环烷基部分被相同或不同的卤素取
代，尤其是氟或氯取代，R3 代表氢，氟或氯，R4 代表氰基或硝基，及R5 代表异氰基，氰硫基，磺基，氯代磺酰基，C1-C4-烷基氨基氧基，
二(C1-C3-烷基)-氨基氧基，C1-C4-亚烷基氨基氧基，C5-C6-亚环
烷基氨基氧基，C5-C6-环烯基氧基，四氢呋喃氧基，全氢吡喃基氧
基，或代表通过氮或氧键合的下列基团之一：
-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，其中：R6 代表氢，或代表任意被氟取代的有1-4个碳原子的烷基，或代
表-CO-R13基团，
其中：
R13 代表氢，或代表有1-4个碳原子的烷基或烷氧基，而且任
意被氟，氯，甲氧基或乙氧基取代，或代表氨基，或代表
在烷基部分有1-4个碳原子的烷基氨基或二烷基氨基，
或代表任意被取代的环丙基，环戊基，环己基，环丙基甲
基，环戊基甲基，环己基甲基，苯基，苄基，苯乙基，呋
喃基，噻吩基或吡啶基，适当的取代基包括：
氟，氯，溴，氰基，硝基，有1-4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，
有1-4个碳原子且有1-9个相同或不同卤原子，特别
是氟和/或氯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，在各烷
基部分有1-4个碳原子的直链或支链烷氧羰基或烷氧基
亚氨基烷基，以及任意被相同或不同的取代基单取代或多
取代的苯基，这些取代基包括氟，氯，溴和/或有1-4个
碳原子的直链或支链烷基或烷氧基，和/或有1-4个碳原
子和1-9个相同或不同卤原子，特别是氟和/或氯原子的
直链或支链卤代烷基或卤代烷氧基：
R7 代表-(CO)n-R13基团，
其中：
R13 具有上面定义且作为特别优选的，
n 代表数字1或2，
R8 代表氢，或代表有1-4个碳原子的烷基或烷氧基，
R9 代表烷基部分有1-4个碳原子的烷氧基，烷基氨基或二烷
基氨基，
R10 代表任意被氟和/氯取代的有1-4个碳原子的烷基，或代
表在烷基部分有1-4个碳原子的烷氧基或烷基氨基或二烷
基氨基，或代表任意取代的苯基，在上述R6中作为特别优选
的那些苯基取代基在这里也可以作为优选的考虑，
R11 代表任意被氟和/或氯取代的有1-4个碳原子的烷基或有3
-6个碳原子的环烷基，或代表任意取代的苯基，萘基，呋
喃基，噻吩基或吡啶基，在上述R6中作为特别优选的那些
苯基取代基在这里也可以作为优选的考虑，和
R12 代表有1-4个碳原子的烷基。
上面给出的一般或优选定义的基团，不但适用于式(I)化合物的最终产物，而且也类似地，适用于制备过程中的起始物质和中间体。
这些定义的基团可以和其它任何所需的基团结合，也就是说，结合上述范围内的优选化合物是可能的。
例如，如果2-(5-氨基-4-氰基-2-氟-苯基)-5-二氟甲基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和二氯乙酰氯被用作本发明方法(a)的起始物质，该反应过程可以用下列反应式概括：
例如，如果2-(2-氯-4-氰基-5-羟基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-硫酮和氯甲酸乙酯被用作本发明方法(b)的起始物质，该反应过程可以用下列反应式概括。
例如，如果2-(2，5-二氟-4-硝基-苯基)-5-二氯甲基-4-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和羟基甲烷-膦酸二乙酯被用作本发明方法(c)的起始物质，该反应过程可以用下列反应式概括。式(II)提供了为制备通式(I)化合物而在本发明方法(a)中被用作起始物质的氨基芳基三唑啉酮的一般定义。在式(II)中，Q，R1，R2，R3，R4和R6有优选或特别优选的含义，这一含义在上面对式(I)化合物的描述中，对优选的或特别优选的Q，R1，R2，R3，R4和R6已作规定。
式(II)的起始物质至今在文献中还没有记载；然而，它们是未公开的专利申请早期的研究课题。
通式(II)的氨基芳基三唑啉酮是上述通式(VIII)的卤代芳基三唑啉酮与氨在0-150℃温度范围内，如果需要，在一种稀释剂如二甲基亚砜存在下反应后得到(参见制备实施例)。
式(III)提供了酰卤的一般定义，而且它任意被用作本发明方法(a)的起始物质。在式(III)中，n和R13有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的n和R13已作规定。
X1优选氟，氯或溴，特别是氯。
式(III)的起始物质是用于有机合成的已知化学物质。
式(IV)提供了原酸酯的一般定义，而且它任意被用作本发明方法(a)的起始物质。在式(IV)中，R8和R9有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的R8和R9已作规定。
式(IV)的起始物质是用于有机合成的已知化学物质。
式(V)提供了羟基芳基三唑啉酮的一般定义，而且被用作本发明制备通式(I)化合物的方法(b)的起始物质。在式(V)中，Q，R1，R2，R3和R4有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的Q，R1，R2，R3和R4已作规定。
式(V)的起始物质至今在文献中还没有记载；然而，它们是未公开的专利申请早期的研究课题(参见DE-P4238125/LeA 29445日期：12.11.1992)。
通式(V)的羟基芳基三唑啉酮是通式(IX)的烷氧基芳基三唑啉酮
其中
Q，R1，R3，R3和R4定义如上，且
R 代表烷基(优选甲基或乙基)
与脱烷基化剂，如溴化硼(III)，在0-50℃温度范围内，在一种稀释剂如二氯甲烷存在下反应后得到，产物用常规方法处理(参见制备实施例)。
式(VI)提供了酰卤的一般定义，而且被用作本发明方法(b)的起始物质。在式(VI)中，R10有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的R10已作规定。
X2优选氟，氯或溴，特别优选氯。
式(VI)的起始物质是用于有机合成的已知化学物质。
式(VII)提供了卤代芳基三唑啉酮的一般定义，而且被用作本发明制备通过(I)化合物的方法(c)的起始物质。在式(VII)中，Q，R1，R2，R3和R4有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的Q，R1，R2，R3和R4已作规定。
X3优选氟或氯，特别优选氟。
式(VII)的起始物质至今在文献中还没有记载；然而，它们是未公开的专利申请早期的研究课题。
通式(VII)的卤代芳基三唑啉酮是通式(X)的三唑啉酮其中Q，R1和R2定义如上与通式(XI)的卤代芳烃
其中
R3，R4和R5定义如上，且
X4代表卤素，优选氟或氯，特别优选氟
在0-150℃温度范围内，在一种稀释剂如二甲基亚砜和酸性受体如碳酸钾存在下反应后得到，产物用常规方法处理(参见制备实施例)。
式(VIII)提供了羟基烷基膦酸酯的一般定义，而且被用作本发明方法(c)的起始物质。在式(VIII)中，R11和R12有优选或特别优选的含义，这一点在上面对式(I)化合物的描述中对优选的或特别优选的R11和R12已作规定。
式(VIII)的起始物质是用于有机合成的已知化学物质。
本发明方法(a)，(b)和(c)中所用的适当稀释剂为常规有机溶剂，特别是包括脂族，脂环族或芳香族和任意的卤代烃，例如，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，四氯甲烷；醚，例如，乙醚，二异丙醚，二噁烷，四氢呋喃，乙二醇二甲醚或乙二醇二乙醚；酮，例如，丙酮，丁酮或甲基异丁酮；腈，例如，乙腈，丙腈或苄腈；酰胺，例如，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酸三酰胺；酯如乙酸甲酯或乙酸乙酯，亚砜如二甲基亚砜，醇如甲醇，乙醇，正或异丙醇，乙二醇单甲醚，乙二醇单乙醚，甘二醇单甲醚，甘二醇单乙醚，它们与水的混合物，或纯水。
本发明方法(a)优选在适当反应助剂存在下进行。适于与式(III)酰卤反应的反应助剂都是常用的无机或有机碱，例如包括，碱土金属或碱金属氢化物、氢氧化物、氨化物、醇盐、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，以及碱性有机氮化合物，如三甲胺，三乙胺，三丁胺，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(DBN)或二氮杂双环十一碳烯(DBU)。
通常用于与式(IV)原酸酯反应的反应助剂是酸性催化剂。优选的适当催化剂是强质子酸，如盐酸或氢氯酸，硫酸，甲磺酸，苯磺酸和对甲苯磺酸。
本发明方法(a)的反应温度可以在较大范围内变化。一般，该方法在0-150℃范围内进行，优选温度范围为10-100℃。
本发明方法(a)一般在大气压力下进行。但是，在高于或低于大气压力下进行也是可以的，一般在0.1-10bar之间。
为了进行本发明方法(a)，各种情况下需要的起始物质一般是近似等摩尔的。但两种成分之一的用量大于另一种也是可以的。一般地，反应是在适当稀释剂中，在反应助剂存在下进行，而且，反应混合物在要求的温度中搅拌数小时。本发明方法采用的处理方法是常规方法(参见制备实施例)。
本发明方法(b)和(c)优选在适当酸受体存在下进行。适当酸受体都是常用的无机或有机碱，例如包括，碱土金属或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐，如氢化钠，氨基钠，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，以及碱有机氮化合物，如三甲胺，三乙胺，三丁胺，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(DBN)或二氮杂双环十一碳烯(DBU)。
本发明方法(b)和(c)的反应温度可以在较大范围内变化。一般，该方法在0-100℃范围内进行，优选温度范围为10-80℃。
本发明方法(b)和(c)一般在常压下进行。但是，在高于或低于该压力下进行也是可以的，一般在0.1-10bar之间。
为了进行本发明方法(b)和(c)，各种情况下需要的起始物质一般是近似等摩尔的。但两种成分之一使用较大的用量也是可以的。一般地，反应是在适当稀释剂中和酸受体存在下进行，而且，反应混合物在要求的温度中搅拌数小时。在本发明方法中每一种后处理用常规方法进行(参见制备实施例)。
本发明的活性化合物可用作破坏阔叶植物的脱叶剂，干燥剂，尤其是除草剂。广义地说，杂草可认为是在不需要生成的地方的所有植物。本发明物质是作为全部还是选择性除草剂基本上取决于其用量。
例如，本发明活性化合物可用于下列植物：
双子叶杂草属：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，昂天莲属，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，罂栗属，矢车菊属，车轴草属，毛茛属和蒲公英属。
双子叶种植植物属：棉属，大豆属，甜菜属，胡萝卜属，菜豆属，豌豆属，茄属，亚麻属，番薯属，野豌豆属，烟草属，番茄属，落花生属，芸苔属，莴苣属，香瓜属和南瓜属。
单子叶杂草属：稗属，狗尾草属，黍属，马唐属，梯牧草属，早熟禾属，羊茅属，禾参属，臂形草属，黑麦草属，雀麦属，燕麦属，莎草属，高粱属，冰草属，狗牙草属，雨久花属，飘拂草属，慈姑草属，荸荠属，鹿单属，雀稗属，鸭嘴草属，尖瓣草属，龙爪茅属，剪股颍属，看麦娘属和Aera。
单子叶种植植物属：稻属，玉蜀黍属，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。
但是，本发明活性化合物的使用并不仅限于这些植物，它们可以相同的方式用于其它植物。
这些化合物由浓度决定它们是适于全面消除如工业区和铁路旁，以及种植或未种树木的道路和广场的杂草。同样，这些化合物可用于消除多年生种植地，如绿化带，装饰树种植地，果园，葡萄园，柑橘园，干果园，香蕉种植园，咖啡种植园，茶叶种植园，橡胶种植园，油棕种植园，可可种植园，软水果种植园和飞地，及草坪，草皮和牧场中的杂草，以及有选择地消除一年生种植地的杂草。
本发明化合物(I)特别适于在单子叶植物和双子叶植物种植地，例如在小麦和大麦地里，以苗前和苗后方式，有选择地消除单子叶和双子叶杂草。
为扩展用途，式(I)化合物还具有杀真菌活性，例如，杀pyicularia oryzae，蔓延疫霉和苹果黑星菌。
这些化合物还可以被转化成常用制剂形式，如溶液，乳液，可湿粉剂，悬浮液，粉末，粉尘剂，糊剂，可溶性粉剂，粒剂，浓悬浮乳液，用活性化合物浸渍的天然和合成材料，以及在非常精细的聚合物胶囊中。
这些制剂可用已知方法制备，例如，用活性化合物与增量剂如液体溶剂和/或固体载体混合，或任意与表面活性剂如乳化剂和/或分散剂和/或发泡剂混合。
在用水作为增量剂时，例如，有机溶剂也可以用作辅助溶剂。作为液体溶剂，主要适合的有：芳香族如二甲苯，甲苯或烷基萘，氯代芳香族或氯代脂肪族烃，如氯苯，氯乙烯或二氯甲烷，脂肪族烃如环己烷或石蜡，例如，石油馏分，矿物和植物油，醇如丁醇或甘二醇，以及它们的醚和酯，酮如丙酮，甲乙酮，甲基异丁酮或环己酮，强极性溶剂如二甲基甲酰胺和二甲基亚砜，以及水。
适宜的固体载体有，例如，铵盐和研碎的天然矿，如高岭土，陶土，滑石，石膏，石英，活性白土(attapulgite)，蒙脱土或硅藻土，及研碎的合成矿物质，如高分散性二氧化硅，氧化铝和硅酸盐。颗粒状固体载体最为适合，例如，粉碎和研细的天然岩石如方解石，大理石，浮石，海泡石和白云石，以及无机和有机粉的合成颗粒和有机材料的颗粒，如锯末，椰子壳，玉米芯和烟梗。
适宜的乳化剂和/或发泡剂有，例如，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，以及蛋清水解产物。
适宜的分散剂有，例如，木素亚硫酸盐废水溶液和甲基纤维素。
粉末、颗粒或乳汁形式的粘合剂如羧甲基纤维素和天然或人工合成的聚合物，例如，阿拉伯胶，聚乙烯醇和聚乙酸乙烯酯，以及天然磷脂如脑磷脂和卵磷脂及合成磷脂都可以用于制剂。另外还可以添加矿物油和植物油。
也可以使用着色剂如无机颜料，例如，氧化铁，氧化钛，普鲁士蓝，及有机染料，例如，茜素染料，偶氮染料和金属酞菁染料，以及痕量营养素如铁、镁、硼、铜、钴、钼和锌盐。
制剂中一般含有0.1-95重量百分比的活性化合物，优选0.5-90wt％。
为了消除杂草，本发明活性化合物也可以其本身或其制剂形式与已知除草剂混合制成制剂或罐中混合使用。
用于混合的适当除草剂是已知除草剂，例如，N-酰苯胺如diflufenican和敌稗；芳基羧酸和二氯吡啶甲酸，麦草畏和毒莠定；芳基氧基链烷酸和2，4D，2，4DB，2，4DP，fluroxypyr，MCPA，MCPP和定草酯；芳氧基-苯氧基链烷酸酯和氯甲草，fenoxaprop-ethyl，fluazifop-butyl，haloxyfop-methyl和quizalofop-ethyl；azinones如chloridazon和达草灭；氨基甲酸酯如氯苯胺灵，异苯敌草，苯敌草和苯胺灵；乙酰氯苯胺如草不绿，刈草胺，去草胺，metazachlor，丙草安，pretilachlor和毒草安；二硝基苯胺如黄草消，胺硝草和氟乐灵；二苯基醚如氟锁草醚，治草醚，fluoroglycofen，fomesafen，halosafen，lactofen和氟硝草醚；尿素如绿麦隆，敌草隆，伏草隆，异丙隆，利谷隆和噻唑隆；羟基胺如枯杀达clethodim，cycloxydim，sethoxydim和tralkoxydim；咪唑啉酮如imazethapyr，imazamethabenz，imazapyr和imazaquin；腈如溴苯腈，敌草腈和碘苯腈；氧基乙酰氨如mefenacet；磺酰脲类如amidosulfuron，bensulfuron-methyl，chlorimuron-ethyl，chlorsulfuron，cinosulfuron，metsulfuron-methyl，nicosulfuron，primisulfurron，pyrazosulfuron-ethyl，thifenssulfuron-methyl，triasulfuron和tributuron-methyl；硫代氨基甲酸酯如苏达灭，草灭特，燕麦敌，EPTC，esprocarb，草达灭，prosulfocarb，米草丹和野麦畏；三嗪如阿特拉津，草净津，西玛津，西草净，去草净和terbutylazine；三嗪酮(triazinones)如六嗪同，苯嗪草和赛克津；其它的还有如杀草强，benfuresate，噻草平，cinmethylin，clomazone，clopyralid，苯敌快，dithiopyr，灭草呋喃，fluorochloridone，glufosinate，草甘膦，isoxaben，达草止，quinchlorac，quinmerac，sulphosate和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，鸟类拒斥剂，植物营养剂及可改善土壤结构的药剂一起混合使用也是可以的。
这些活性化合物可以本身或制剂形式或用前稀释的形式如随时可用的溶液，悬浮液，乳液，粉末，糊剂和颗粒形式使用。可采用常规方法施用，例如，浇灌，喷洒，喷雾或播撒。
本发明化合物既可以在植物苗前使用，也可以在苗后使用。它们可以在播种前混入土壤。活性化合物的用量可以在较大范围内变化，这主要取决于所要达到的效果。一般来说，每公顷土壤表面活性化合物的用量为10g到10Kg，优选50g-5Kg。
本发明活性化合物的制备和用途用下列实施例说明。
制备实施例
实施例1
方法(a)
将1.01g(0.01mol)三乙胺与3.15g(0.01mol)2-(2-氟-4-氰基-5-氨基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的50ml乙腈一起放入反应容器。搅拌的混合物用1.21g(0.01mol)三甲基乙酰氯处理，在室温(20℃)搅拌5小时并浓缩。剩余物用水搅拌，吸滤并用硅胶[lacuna]纯化(洗脱剂：环己烷/乙酸乙酯3∶1)。得到1.7g(43％理论值)2-[2-氟-4-氰基-5-(叔丁基-羰基氨基)-苯基]-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点149℃。
实施例2
方法(a)
将3.15g(0.01mol)2-(2-氟-4-氰基-5-氨基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和0.01g对甲苯磺酸的20ml原甲酸三乙酯在回流温度搅拌20分钟。冷却后，将溶液浓缩并从少量异丙醇中重结晶。得到2g(54％理论值)2-(2-氟-4-氰基-5-乙氧基亚甲基氨基苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点91℃。
实施例3
方法(b)
将2g(0.007mol)2-(2-氟-4-氰基-5-羟基-苯基)-4-甲基-5-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的50ml乙腈用0.23g(0.0077mol)氢化钠(80％于石蜡中)处理，并将混合物在20℃搅拌20分钟。接着加入0.84g(0.0077mol)氯甲酸乙酯，并将混合物在室温(20℃)搅拌8小时。浓缩后，将混合物用水搅拌，用浓盐酸酸化，用二氯甲烷萃取三次，有机相用硫酸钠干燥并浓缩。在硅胶上用色谱法纯化(洗脱剂：环己烷、乙酸乙酯1∶1)。得到0.8g(32％理论值)2-[2-氟-4-氰基-5-(乙氧基-羰基氧基)-苯基]-4-甲基-5-二氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮为油。
1H NMR(CDCl3)：3.50；4.354.43；7.55-7.58ppm
实施例4
方法(c)
将6.3g(0.03mol)1-羟基-异丁基膦酸二乙酯的100ml乙腈用0.9g(0.03mol)氢化钠(80％于石蜡中)处理，并将混合物在20℃搅拌20分钟。加入3.15g(0.01mol)2-(2，5-二氟-4-氰基苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮后将混合物在室温(20℃)搅拌12小时。混合物用水搅拌，吸滤沉淀产物并从环己烷重结晶。
得到3g(59％理论值)2-[2-氟-4-氰基-5-(1-二乙氧基磷酰基-异丁氧基)-苯基]-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点113℃。
可用类似实施例1-4方法和按照本发明一般描述的制备方法制备其它实施例的式(I)化合物并列于下面表1。
表I：式(I)化合物的实施例 
式(II)的起始物质：
实施例(II-I)：
将9.54g(0.03mol)2-(2，5-二氟-4-氰基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的150ml二甲基亚砜加热至120℃，然后通入20小时氨气。冷却后，将溶液在冰水中搅拌，吸滤出沉淀的产物用水洗涤，剩余物从异丙醇重结晶。得到5.8(61％理论值)2-(2-氟-4-氰基-5-氨基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点193℃。
式(V)的起始物质：
实施例(V-I)：
将4.95g(0.015mol)2-(2-氟-4-氰基-5-甲氧基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的200ml二氯甲烷倒入10℃的反应容器，滴加45g(0.045mol)溴化硼(III)的二氯甲烷的1摩尔溶液。将反应混合物在20℃搅拌12小时，然后用100ml水处理。搅拌混合物10分钟后，分离有机相，用水洗涤，硫酸钠干燥和过滤。在水泵真空下通过蒸馏从滤液中小心除去溶剂。得到3.1g(65％理论值)2-(2-氟-4-氰基-5-羟基-苯基)-4-乙基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点195℃。
式(VII)的起始物质：
实施例(VII-I)：
将5.3g(0.038mol)碳酸钾在室温下加到5.3g(0.032mol)4-甲基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮(例如，参见US3,780,052)和5.5g(0.032mol)5-氯-2，4-二氟苄腈的100ml二甲基亚砜中，并将混合物在100℃加热36小时。为了后处理，冷却的混合物被倒入水中，用稀盐酸将pH调至2。反复用二氯甲烷萃取混合物，合并的有机相用硫酸钠干燥，并真空浓缩。剩余物在硅胶上进行色谱分离(洗脱剂：二氯甲烷)。得到1.8g(18％理论值)2-(2-氯-4-氰基-5-氟-苯基)-4-甲基-5-三氟甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点105℃。
应用实施例
在应用实施例中，下列化合物(A)被用作对比物。
2-(4-氰基-2，5-二氟-苯基)-5-甲基-4-炔丙基-2，4-二氢-3H-1，2，4-三唑-3-酮(公开于EP-A370332)。
实施例A
苗前试验
溶剂：5份重量丙酮
乳化剂：1份重量烷基芳基聚乙二醚
为了制备适用的制剂，将1份重量的活性化合物与上述分量的溶剂和上述分量的乳化剂混合，并用水稀释到所需浓度。
将试验植物的种子播种到常规土壤中，24小时后，浇灌含活性化合物的制剂。每单位面积浇灌的量应保持常数。活性化合物在制剂中的浓度并不重要，关键是活性化合物在单位面积内的用量必须精确。三星期后，植物的破坏程度用相对于未作处理的对照组破坏程度之比的百分数表示。这些数字表示：
0％＝无作用(同未作处理的对照组)
100％＝完全破坏
在本试验中，比如，制备实施例4，13，17，25，26，37和41的化合物的活性对大麦和小麦田中的杂草如马唐属(80-95％)，苘麻属(100％)，藜属(95-100％)，牛膝菊属(70-100％)，母菊属(60-100％)，马齿苋属(70-100％)，茄属(80-100％)和堇菜属(80-100％)除草能力明显高于现有技术中化合物(大麦田0-10％，小麦田0％)。
Claims (8)
1、通式(I)新的取代三唑啉酮
其中：Q 代表氧或硫R1 代表卤代烷基，R2 代表氢，氨基，氰基，烷基，烯基，炔基，卤代烷基，卤代烯基，
卤代炔基，烷氧基烷基，亚烷基亚氨基，或各种情况下任意被取
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，及R5 代表异氰基，氰硫基，磺基，卤代磺酰基，烷基氨基氧基，二烷
基氨基氧基，亚烷基氨基氧基，亚环烷基氨基氧基，或各种情况
下被任意取代的环烯基氧基或杂环基氧基，或下列通过氮或氧键
合的基团之一：
-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，
其中：
R6代表氢，或代表烷基，烯基或炔基，其中每一个可任意被卤素
取代，或代表-CO-R13，
其中：
R13代表氢，或代表烷基或烷氧基，它们可以任意被卤素或烷
氧基取代，或代表氨基，烷基氨基或二烷基氨基，或代表任意
被取代的环烷基，环烷基烷基，芳基，芳烷基或杂环基烷基，
R7代表-(CO)n-R13基团，
其中：
R13如上定义，
n 代表数字1或2，
R8 代表氢，烷基或烷氧基，
R9 代表烷氧基，烷基氨基或二烷基氨基，
R10 代表任意被卤素取代的烷基，或代表烷氧基，或代表烷基氨
基，或代表二烷基氨基或代表任意取代的芳基，
R11 代表任意被卤素取代的烷基或环烷基，或各种任意取代的芳
基或杂环基，及
R12 代表烷基。
2、根据权利要求1的通式(I)的新的取代三唑啉酮，其特征在于Q 代表氧或硫，R1 代表有1-6个碳原子和1-13个相同或不同卤原子，尤其是
氟，氯，溴或碘的直链或支链卤代烷基，R2 代表氢，氨基，氰基，有1-8个碳原子的直链或支链烷基，
有2-6个碳原子的直链或支链烯基或炔基，有1-6个碳原
子和1-13个相同或不同卤原子，尤其是氟，氯，溴或碘的直
链或支链卤代烷基，或代表有2-6个碳原子和1-11个相同
或不同卤原子，尤其是氟，氯，溴或碘的直链或支链卤代烯基
或卤代炔基，或代表在各烷基部分有1-4个碳原子的直链或
支链烷氧基烷基，或代表有1-8个碳原子的直链或支链亚烷
基亚氨基，或代表在各环烷基部分有3-8个碳原子的环烷基
或环烷基烷基，而且如果可能，在直链或支链烷基部分有1-4
个碳原子，并在环烷基部分被相同或不同的卤素取代基，尤其
是氟，氯，溴和/或碘单一的或多重的取代。R3 代表氢，氟，氯，溴或碘，R4 代表氰基或硝基，及R5 代表异氰基，氰硫基，磺基，卤代磺酰基，C1-C6-烷基氨基氧基，
二(C1-C4-烷基)-氨基氧基，C1-C6-亚烷基氨基氧基或C5-C6-亚
环烷基氨基氧基，或任意被卤素，C1-C4-烷基或C1-C4-烷氧基取
代的C5-C6-环烯氧基，全氢呋喃氧基或全氢吡喃氧基，或代表通
过氮或氧键合的下列基团之一：
-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，
其中：R6 代表氢，或代表烷基，烯基或炔基，其中每个基团具有至多
6个碳原子并任意被氟和/或氯取代，或代表-CO-R13，
其中：
R13 代表氢，或代表烷基或烷氧基，它们具有1-6个碳原
子，并且可以任意被氟，氯或C1-C4-烷氧基取代，或代
表氨基，或代表在烷基部分有1-6个碳原子的烷基
氨基或二烷基氨基，或代表任意被取代的C3-C6-环烷
基，C3-C6-环烷基C1-C4-烷基，苯基，萘基，苯基-
C1-C4-烷基，呋喃基，噻吩基或吡啶基，适当的取代基
包括：
卤素，氰基，硝基，有1-4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，
有1-4个碳原子且有1-9个相同或不同卤原子的
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，在各烷基部分有1
-4个碳原子的直链或支链烷氧羰基或烷氧基亚氨基
烷基，以及任意被相同或不同的取代基单取代或多取
代的苯基，这些取代基包括卤素和/或有1-4个碳原
子的直链或支链烷基或烷氧基，和/或有1-4个碳原
子和1-9个相同或不同卤原子的直链或支链卤代烷
基或卤代烷氧基；R7 代表-(CO)n-R13基团，其中：
R13 具有上面定义且作为优选，
n 代表数字1或2，R8 代表氢，或代表有1-6个碳原子的烷基或烷氧基，R9 代表烷基部分有1-6个碳原子的烷氧基，烷基氨基或二烷
基氨基，R10 代表任意被氟和/或氯取代的有1-6个碳原子的烷基，或
代表在烷基部分有1-6个碳原子的烷氧基，烷基氨基或
二烷基氨基，或代表任意取代的苯基，优选在上述优选R6
中的那些苯基取代基，
R11 代表任意被氟和/或氯取代的有1-6个碳原子的烷基或有3
-6个碳原子的环烷基，或任意取代的苯基，萘基，呋喃
基，噻吩基或吡啶基，优选在上述优选R6中的那些苯基取
代基，及
R12 代表有1-6个碳原子的烷基。
3、根据权利要求1的通式(I)新的取代三唑啉酮，其特征在于Q 代表氧或硫，R1 代表有1-4个碳原子和1-9个相同或不同卤原子，尤其是
氟，氯，溴或碘的直链或支链卤代烷基，R2 代表氢，氨基，氰基，有1-4个碳原子的直链或支链烷基，
有3-4个碳原子的直链或支链烯基或炔基，有1-4个碳原
子和1-9个相同或不同卤原子，尤其是氟或氯的直链或支链
卤代烷基，有3-4个碳原子和1-5个相同或不同卤原子，尤
其是氟或氯的直链或支链卤代烯基或卤代炔基，或代表在各烷
基部分有1-3个碳原子的直链或支链烷氧基烷基，或代表有1
-4个碳原子的直链或支链亚烷基亚氨基，或代表在各环烷基
部分有3-6个碳原子的环烷基或环烷基烷基，而且如果可能，
在直链或支链烷基部分有1-3个碳原子，并在环烷基部分单
一或多重被相同或不同的卤素取代基，尤其是氟或氯取代，R3 代表氢，氟或氯，R4 代表氰基或硝基，及R5 代表异氰基，氰硫基，磺基，卤代磺酰基，C1-C4-烷基氨基氧基，
二(C1-C3-烷基)-氨基氧基，C1-C4-亚烷基氨基氧基，C5-C6-亚环
烷基氨基氧基，C5-C6-环烯基氧基，四氢呋喃氧基，全氢吡喃氧
基，或代表通过氮或氧键合的下列基团之一：
-NR6R7，-N＝CR8R9，-O-CO-R10，-O-CS-R10，-O-CHR11-P(O)(OR12)2，
其中：
R6 代表氢，或代表任意被氟取代的有1-4个碳原子的烷基，
或代表-CO-R13基团，
其中：
R13 代表氢，或代表有1-4个碳原子的烷基或烷氧基，而
且任意被氟，氯，甲氧基或乙氧基取代，或代表氨基，
或代表在烷基部分有1-4个碳原子的烷基氨基或二
烷基氨基，或代表任意被取代的环丙基，环戊基，
环己基，环丙基甲基，环戊基甲基，环己基甲基，苯
基，苄基，苯乙基，呋喃基，噻吩基或吡啶基，适当
的取代基包括：
氟，氯，溴，氰基，硝基，有1-4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，有1-4个碳原子且有1-9个相同或不同
卤原子，特别是氟和/或氯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，在各烷基部分有1-4个碳原子的
直链或支链烷氧羰基或烷氧基亚氨基烷基，以及任意
被相同或不同的取代基单取代或多取代的苯基，这些
取代基包括氟，氯，溴和/或有1-4个碳原子的直链
或支链烷基或烷氧基，和/或有1-4个碳原子和1-9
个相同或不同卤原子，特别是氟和/或氯原子的直链或
支链卤代烷基或卤代烷氧基；R7 代表-(CO)n-R13基团，其中：
R13 具有上面定义且作为特别优选的，
n 代表数字1或2，R8 代表氢，或代表有1-4个碳原子的烷基或烷氧基，R9 代表烷基部分有1-4个碳原子的烷氧基，烷基氨基或
二烷基氨基，R10 代表任意被氟和/氯取代的有1-4个碳原子的烷基，
或代表在烷基部分有1-4个碳原子的烷氧基或烷基
氨基或二烷基氨基，或代表任意取代的苯基，特别优
选在上述优选R6中的那些苯基取代基，R11 代表任意被氟和/或氯取代的有1-4个碳原子的烷基
或有3-6个碳原子的环烷基，或代表任意取代的苯
基，萘基，呋喃基，噻吩基或吡啶基，特别优选在上
述优选R6中的那些苯基取代基，及
R12 代表有1-4个碳原子的烷基。
4、通式(I)新的取代三唑啉酮的制备方法，其中：R1，R2，R3，R4，R5和Q的定义同权利要求1，其特征在于(a)通式(II)氨基芳基三唑啉酮其中，Q，R1，R2，R3，R4和R6定义如上，与通式(III)酰卤反应，
X1-(CO)n-R13 (III)其中，n和R13定义如上，X1代表卤素，或与通式(IV)的原酸酯反应，
R8-C(OR9)3 (IV)其中，R8和R9定义如上，如果需要，在反应助剂和稀释剂存在下进行，或(b)通式(V)羟基芳基三唑啉酮
其中，Q，R1，R2，R3和R4定义如上，与通式(VI)的酰基卤反应，
X2-COR10 (VI)其中，R10定义如上，X2代表卤素，如果需要，在酸受体和稀释剂存在下进行，或(c)通式(VII)卤代芳基三唑啉酮
其中，Q，R1，R2，R3和R4定义如上，X3代表卤素，
与通式(VIII)的羟基烷基膦酸酯反应，
HO-CHR11-P(O)(OR12)2(VIII)
其中，R11和R12定义如上。
如果需要，在酸受体和稀释剂存在下进行。
5、除草组合物，其特征在于它们含有至少一种权利要求1-5中的通式(I)的取代的三唑啉酮。
6、除去不需要植物的方法，其特征在于将权利要求1-5通式(I)的取代的三唑啉酮施用到植物上和/或它们的周围环基中。
7、使用权利要求1-5通式(I)的取代的三唑啉酮除去不需要的植物。
8、除草组合物的制备方法，其特征在于将权利要求1-5通式(I)的取代的三唑啉酮与增量剂和/或表面活性物混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4405614A DE4405614A1 (de) | 1994-02-22 | 1994-02-22 | Substituierte Triazolinone |
| DEP4405614.1 | 1994-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1150421A true CN1150421A (zh) | 1997-05-21 |
Family
ID=6510856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95191743A Pending CN1150421A (zh) | 1994-02-22 | 1995-02-09 | 取代的三唑啉酮及其作为除草剂的用途 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0746550A1 (zh) |
| JP (1) | JPH09509923A (zh) |
| CN (1) | CN1150421A (zh) |
| AU (1) | AU1808495A (zh) |
| BR (1) | BR9506928A (zh) |
| CA (1) | CA2183641A1 (zh) |
| DE (1) | DE4405614A1 (zh) |
| HU (1) | HU9602306D0 (zh) |
| PL (1) | PL315970A1 (zh) |
| WO (1) | WO1995022532A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020063756A1 (en) * | 2018-09-27 | 2020-04-02 | Dongguan HEC Pesticides R&D Co., Ltd. | Triazole compound and use thereof in agriculture |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1100789T3 (da) * | 1998-07-24 | 2005-05-23 | Bayer Cropscience Ag | Substituerede benzoylcyclohexandioner |
| GB9902592D0 (en) | 1999-02-06 | 1999-03-24 | Hoechst Schering Agrevo Gmbh | Fungicides |
| DE19914140A1 (de) | 1999-03-27 | 2000-09-28 | Bayer Ag | Substituierte Benzoylpyrazole |
| DE19920791A1 (de) | 1999-05-06 | 2000-11-09 | Bayer Ag | Substituierte Benzoylisoxazole |
| DE19921424A1 (de) | 1999-05-08 | 2000-11-09 | Bayer Ag | Substituierte Benzoylketone |
| EP1178036A1 (en) * | 2000-08-04 | 2002-02-06 | Aventis Cropscience S.A. | Fungicidal phenylimidate derivatives |
| PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| MXPA05007130A (es) * | 2002-12-31 | 2005-08-26 | Pfizer Prod Inc | Inhibidores benzamida del receptor p2x7. |
| US7071223B1 (en) | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
| PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
| EP1776352A1 (en) | 2004-06-29 | 2007-04-25 | Pfizer Products Inc. | Method for preparing 5-[4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h[1,2,4]triazin-2-yl]-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
| EP1926718B1 (en) | 2005-09-13 | 2012-09-05 | Bayer CropScience AG | Pesticide thiazolyloxy substituted phenylamidine derivatives |
| WO2021193410A1 (ja) * | 2020-03-23 | 2021-09-30 | 日本曹達株式会社 | ベンズアミド化合物および除草剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE4238125A1 (de) * | 1992-11-12 | 1994-05-19 | Bayer Ag | Substituierte Triazolinone |
| DE4303376A1 (de) * | 1993-02-05 | 1994-08-11 | Bayer Ag | Substituierte Triazolinone |
| DE4309966A1 (de) * | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte 1-Aryltriazolinone |
-
1994
- 1994-02-22 DE DE4405614A patent/DE4405614A1/de not_active Withdrawn
-
1995
- 1995-02-09 WO PCT/EP1995/000466 patent/WO1995022532A1/de not_active Application Discontinuation
- 1995-02-09 PL PL95315970A patent/PL315970A1/xx unknown
- 1995-02-09 EP EP95909695A patent/EP0746550A1/de not_active Withdrawn
- 1995-02-09 CA CA002183641A patent/CA2183641A1/en not_active Abandoned
- 1995-02-09 HU HU9602306A patent/HU9602306D0/hu unknown
- 1995-02-09 CN CN95191743A patent/CN1150421A/zh active Pending
- 1995-02-09 BR BR9506928A patent/BR9506928A/pt not_active Application Discontinuation
- 1995-02-09 AU AU18084/95A patent/AU1808495A/en not_active Abandoned
- 1995-02-09 JP JP7521556A patent/JPH09509923A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020063756A1 (en) * | 2018-09-27 | 2020-04-02 | Dongguan HEC Pesticides R&D Co., Ltd. | Triazole compound and use thereof in agriculture |
| CN110950812A (zh) * | 2018-09-27 | 2020-04-03 | 东莞市东阳光农药研发有限公司 | 三氮唑化合物及其在农业中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4405614A1 (de) | 1995-08-24 |
| WO1995022532A1 (de) | 1995-08-24 |
| HU9602306D0 (en) | 1996-10-28 |
| BR9506928A (pt) | 1997-09-09 |
| EP0746550A1 (de) | 1996-12-11 |
| JPH09509923A (ja) | 1997-10-07 |
| AU1808495A (en) | 1995-09-04 |
| CA2183641A1 (en) | 1995-08-24 |
| PL315970A1 (en) | 1996-12-23 |
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