CN1218468A - 作为除草剂的取代的芳基磺酰基氨基(硫代)羰基－三唑啉(硫)酮 - Google Patents
作为除草剂的取代的芳基磺酰基氨基(硫代)羰基－三唑啉(硫)酮 Download PDFInfo
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- CN1218468A CN1218468A CN97194464A CN97194464A CN1218468A CN 1218468 A CN1218468 A CN 1218468A CN 97194464 A CN97194464 A CN 97194464A CN 97194464 A CN97194464 A CN 97194464A CN 1218468 A CN1218468 A CN 1218468A
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- -1 Substituted aryl sulphonyl amino (thio) carbonyl-triazolin Chemical compound 0.000 title claims abstract description 186
- 239000004009 herbicide Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 32
- 239000001301 oxygen Substances 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000005864 Sulphur Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 9
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
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- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 5
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
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- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 18
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 13
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 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 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
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- 239000002184 metal Substances 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical compound CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- TWBIDQDUOXHFSN-UHFFFAOYSA-N C[CH]C=O Chemical compound C[CH]C=O TWBIDQDUOXHFSN-UHFFFAOYSA-N 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 2
- GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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Abstract
本发明涉及新的式(Ⅰ)的取代的芳基磺酰基氨基(硫代)羰基－三唑啉(硫)酮,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,氨基或代表各自任选被取代的烷基,烷氧基,烷基羰基,烷氧羰基,烷硫基,烷基亚磺酰基,烷基磺酰基,链烯基,炔烃基或亚烷基氨基,R2代表氢或代表各自任选被取代的烷基,烷基羰基,烷氧羰基,烷基磺酰基,链烯基或炔烃基,或者与R1一起代表任选插入氧原子和/或任选被取代的链烷二基,R3代表氢,氰基,硝基,卤素或代表各自任选被取代的烷基,烷基羰基或烷氧羰基,R4代表氢,羟基,氨基,亚烷基氨基或者代表各自任选被取代的选自下面的基团:烷基,链烯基,炔烃基,烷氧基,链烯基氧基,烷基氨基,二烷基氨基,环烷基,环烷基烷基,环烷基氨基,芳基,芳基烷基,和R5代表氢,羟基,巯基,氨基,氰基,卤素,或者代表各自任选被取代的选自下面的基团:烷基,烷氧基,烷硫基,烷基氨基,二烷基氨基,链烯基,炔烃基,链烯基氧基,炔烃基氧基,链烯基硫基,炔烃基硫基,链烯基氨基,炔烃基氨基,环烷基,环烷基氧基,环烷基硫基,环烷基氨基,环烷基烷基,芳基,芳基氧基,芳基硫基,芳基氨基,芳基烷基,以及式(Ⅰ)化合物的盐,并且涉及制备这些新的化合物的方法,以及涉及它们作为除草剂的用途。
Description
本发明涉及新的取代的芳基磺酰基氨基(硫代)羰基-三唑啉(硫)酮，涉及其多种制备方法，以及涉及其作为除草剂的用途。
已知一些磺酰基氨基羰基三唑啉酮具有除草性能(参见EP-A341489,EP-A422469,EP-A425948,EP-A431291,EP-A507171)。但是这些化合物的活性不是在所有方面都令人满意。
因此，本发明提供新的通式(Ⅰ)的取代的芳基磺酰基氨基(硫代)羰基-三唑啉(硫)酮，(Ⅰ)
其中
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，氨基或代表各自任选被取代的烷基，烷氧基，烷基羰基，烷氧羰基，烷硫基，烷基亚磺酰基，烷基磺酰基，链烯基，炔烃基或亚烷基氨基，
R2代表氢或代表各自任选被取代的烷基，烷基羰基，烷氧羰基，烷基磺酰基，链烯基或炔烃基，或者与R1一起代表任选插入氧原子和/或任选被取代的链烷二基，
R3代表氢，氰基，硝基，卤素或代表各自任选被取代的烷基，烷基羰基或烷氧羰基，
R4代表氢，羟基，氨基，亚烷基氨基或者代表各自任选被取代的选自下面的基团：烷基，链烯基，炔烃基，烷氧基，链烯基氧基，烷基氨基，二烷基氨基，环烷基，环烷基烷基，环烷基氨基，芳基，芳基烷基，和
R5代表氢，羟基，巯基，氨基，氰基，卤素，或者代表各自任选被取代的选自下面的基团：烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，链烯基，炔烃基，链烯基氧基，炔烃基氧基，链烯基硫基，炔烃基硫基，链烯基氨基，炔烃基氨基，环烷基，环烷基氧基，环烷基硫基，环烷基氨基，环烷基烷基，芳基，芳基氧基，芳基硫基，芳基氨基，芳基烷基，
以及式(Ⅰ)化合物的盐。
当进行下面的反应时得到了新的通式(Ⅰ)的取代的芳基磺酰基氨基(硫代)羰基-三唑啉酮：
(a)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅲ)的异(硫代)氰酸磺酰酯反应，
(Ⅱ)其中Q1,R4和R5各自如上定义，
(Ⅲ)
其中
Q2,R1,R2和R3各自如上定义，
或者
(b)如果适当在酸受体存在下和如果适当在稀释剂存在下，通式(Ⅳ)的三唑啉(硫)酮衍生物与通式(Ⅴ)的磺酰胺反应，
(Ⅳ)其中Q1,Q2,R4和R5各自如上定义，Z代表卤素，烷氧基，芳烷氧基或芳基氧基，(Ⅴ)
其中
R1,R2和R3各自如上定义，
或者
(c)如果适当在酸受体存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅵ)的磺酰胺衍生物反应，
(Ⅱ)其中Q1,R4和R5各自如上定义，
(Ⅵ)
其中
Q2,R1,R2和R3各自如上定义，
Z代表卤素，烷氧基，芳烷氧基或芳基氧基，
(d)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅶ)的磺酰卤和通式(Ⅷ)的(硫代)氰酸金属盐反应，
(Ⅱ)其中Q1,R4和R5各自如上定义，
(Ⅶ)其中R1,R2和R3各自如上定义，X代表卤素，MQ2CN (Ⅷ)其中
Q2如上定义，和
M代表碱金属或碱土金属等价物，
并且如果适当，将由方法(a),(b),(c)或(d)得到的式(Ⅰ)化合物通过常规方法转化为盐。
新的通式(Ⅰ)的取代的芳基磺酰基氨基(硫代)羰基-三唑啉酮具有强的除草活性。
本发明优选提供式(Ⅰ)化合物，
其中
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，氨基，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷氧基，烷基羰基，烷氧羰基，烷硫基，烷基亚磺酰基或烷基磺酰基，或者代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基，炔烃基或亚烷基氨基，
R2代表氢，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷基羰基，烷氧羰基或烷基磺酰基，代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基或炔烃基，或与R1一起代表具有2-6个碳原子的可任选插入氧原子和/或任选被卤素或C1-C4-烷基-取代的链烷二基，
R3代表氢，氰基，硝基，卤素或者代表各自任选被卤素-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷基羰基或烷氧羰基，
R4代表氢，羟基，氨基，C1-C6-亚烷基氨基，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，代表各自任选被氟-，氯-和/或溴-取代的C2-C6-链烯基或C2-C6-炔烃基，代表C1-C6-烷基氧基或C3-C6-链烯基氧基，代表各自任选被氟-和/或氯-取代的C1-C6-烷基氨基，二-(C1-C4-烷基)-氨基或C1-C4-烷酰基氨基，代表各自任选被氟-，氯-，溴-和/或C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基，或者代表各自任选被氟-，氯-，溴-，氰基-，硝基-,C1-C4-烷基-，三氟甲基-,C1-C4-烷氧基-和/或C1-C4-烷氧羰基-取代的苯基或苯基-C1-C4-烷基，和
R5代表氢，羟基，巯基，氨基，氰基，卤素，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基，炔烃基，链烯基氧基，炔烃基氧基，链烯基硫基，炔烃基硫基，链烯基氨基或炔烃基氨基，代表各自任选被氰基-，卤素-或C1-C4-烷基-取代的各种情况下在环烷基中具有3-6个碳原子的环烷基，环烷基氧基，环烷基硫基，环烷基氨基或环烷基-C1-C4-烷基，或者代表各自任选被氰基-，卤素-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-或C1-C4-卤代烷氧基-取代的苯基，苯氧基，苯硫基，苯基氨基或苯基-C1-C4-烷基。
本发明还优选提供其中Q1,Q2,R1,R2,R3,R4和R5各自优选如上文定义的式(Ⅰ)化合物的钠盐，钾盐，镁盐，钙盐，铵盐，C1-C4-烷基-铵盐，二-(C1-C4-烷基)-铵盐，三-(C1-C4-烷基)-铵盐，四-(C1-C4-烷基)-铵盐，三-(C1-C4-烷基)-锍，C5-或C6-环烷基铵盐和二-(C1-C2-烷基)-苄基-铵盐。
本发明特别提供式(Ⅰ)化合物，
其中
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，代表各自任选被氰基-，氟-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，甲氧基，乙氧基，正丙氧基，异丙氧基，乙酰基，丙酰基，正-或异-丁酰基，甲氧羰基，乙氧羰基，正-或异-丙氧羰基，甲基硫基，乙基硫基，正-或异-丙基硫基，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，代表丙烯基，丁烯基，丙炔基或丁炔基或者代表亚丙基氨基，
R2代表氢，代表各自任选被氰基-，氟-，甲氧基-，或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，乙酰基，丙酰基，正-或异-丁酰基，代表甲氧羰基，乙氧羰基，正-或异-丙氧羰基，甲基磺酰基，乙基磺酰基，正-或异-丙基磺酰基，代表丙烯基，丁烯基，丙炔基或丁炔基，或者与R1一起代表任选被甲基-和/或乙基-取代的乙烷-1,2-二基，丙烷-1,3-二基，丁烷-1,4-二基，戊烷-1,5-二基，或3-氧杂-戊烷-1,5-二基，
R3代表氢，代表氰基，硝基，氟，氯，溴，或代表各自任选被氟-取代的甲基，乙基，正丙基或异丙基，
R4代表氢，代表各自任选被氟-，氯-，氰基-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，代表各自任选被氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基或丁炔基，代表甲氧基，乙氧基，正-或异-丙氧基或者代表烯丙基氧基，代表甲基氨基，乙基氨基，正-或异-丙基氨基，正-、异-、仲-或叔-丁基氨基，二甲基氨基或二乙基氨基，代表各自任选被氟-，氯-，溴-，甲基-或乙基-取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，或者代表任选被氟-，氯-，溴-，氰基-，甲基-，三氟甲基或甲氧基-取代的苄基或苯基，和
R5代表氢，羟基，巯基，氨基，氟，氯，溴，代表各自任选被氟-，氯-，氰基-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基、异丙基，正-、异-、仲-或叔-丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲-或叔-丁基氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，正-、异-、仲-或叔-丁基硫基，甲基氨基，乙基氨基，正-或异-丙基氨基，正-、异-、仲-或叔-丁基氨基，二甲基氨基或二乙基氨基，代表各自任选被氰基-，氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基，丁炔基，丙烯基氧基，丁烯基氧基，丙炔基氧基，丁炔基氧基，丙烯基硫基，丁烯基硫基，丙炔基硫基，丁炔基硫基，丙烯基氨基，丁烯基氨基，丙炔基氨基或丁炔基氨基，代表各自任选被氰基-，氟-，氯-，溴-，甲基-或乙基-取代的环丙基，环丁基，环戊基，环己基，环丙基氧基，环丁基氧基，环戊基氧基，环己基氧基，环丙基硫基，环丁基硫基，环戊基硫基，环己基硫基，环丙基氨基，环丁基氨基，环戊基氨基，环己基氨基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，或者代表各自任意被氰基-，氟-，氯-，甲基-，三氟甲基-，甲氧基-或甲氧羰基-取代的苯基，苯氧基，苯基硫基，苯基氨基或苄基。
上述一般或优选基团定义适用于式(Ⅰ)终产物，并相应地适用于每种情况下制备所需要的前体或中间体。这些基团定义可以根据需要相互组合，因此包括指出的优选范围之间的组合。
在基团的定义中，烃基例如烷基，链烯基或炔烃基是直链或支链的，即使没有明确地表明，但是也包括与杂原子的结合，例如烷氧基，烷硫基或烷基氨基中的结合。
卤素一般代表氟，氯，溴或碘，优选氟，氯或溴，特别是氟或氯。
使用例如异氰酸6-氟-2-(N-甲基-N-甲磺酰基-氨基)-苯基磺酰酯和4-乙基-5-乙氧基-2,4-二氢-3H-1,2,4-三唑-3-酮为起始物，则本发明方法(a)的反应过程能通过下面的反应式说明：
使用例如2-乙基氨基-苯磺酰胺和2-苯氧羰基-4-甲氧基-5-乙基-2,4-二氢-3H-1,2,4-三唑-3-酮为起始物，则本发明方法(b)的反应过程能通过下面的反应式说明：
使用例如N-甲氧羰基-2-二甲基氨基-3-甲基-苯磺酰胺和4-甲基-5-甲基硫基-2,4-二氢-3H-1,2,4-三唑-3-酮为起始物，则本发明方法(c)的反应过程能通过下面的反应式说明：
使用例如2-烯丙基氨基-苯磺酰氯，4-甲基氨基-5-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮和氰酸钠为起始物，则本发明方法(d)的反应过程能通过下面的反应式说明：
式(Ⅱ)提供了在制备式(Ⅰ)化合物的本发明方法(a),(c)和(d)中用作起始物的三唑啉(硫)酮的一般定义。在式(Ⅱ)中，Q1,R4和R5各自优选或特别具有上文已经指明的，与描述本发明式(Ⅰ)化合物相关的，作为Q1,R4和R5优选的或特别优选的定义的那些定义。
通式(Ⅱ)的三唑啉(硫)酮是已知的和/或可以通过本身已知的方法制备
(参见Arch.Pharm.301(1963),827；同期刊307(1974),889；BUll.Soc.Chim France 1962,1365；同期刊1975,1191；Chem.Ber.90(1957),909-921；同期刊98(1965),3025-3099；同期刊102(1969),755；J.Heterocycl.Chem.15(1978),237-240；J.IndianChem.Soc.6(1929),565；Liebigs Ann.Chem.637(1960),135；MonatshefteChemie 123(1992),257；Tetrahedron 32(1976),2347-2352；Helv.Chim.Acta 63(1980),841-859；J.Chem.Soc.C1967,746-751；同期刊1970,26-34；J.ChemSoc.Perkin I 1973,2644；Fen Fak.Derg.,Seri A(Ege Univ)7(1984),1-6-化学摘要101:90846m中引用；EP-A283 876；EP-A294 666；EP-A298 371；EP-A301 946；EP-A305 844；EP-A341 489；EP-A362 633,EP-A370 293；EP-A391 187；EP-A398 096；EP-A398 097；EP-A399 294；EP-A415 196；EP-A422 469；EP-A425 948；EP-A431 291；EP-A477 646；EP-A502 307；EP-A503 437；EP-A505 819；EP-A511 569；EP-A513 621；DE-A23 36 827；DE-A38 39 206；DE-A39 16 208；DE-A39 16 930；DD-P64 970；WO-A93/04050).
式(Ⅲ)提供了制备式(Ⅰ)化合物的本发明方法(a)中也用作起始物的异(硫代)氰酸磺酰酯的一般定义。在式(Ⅲ)中,Q2,R1,R2和R3各自优选或特别具有上文已经指明的，与描述本发明式(Ⅰ)化合物相关的，作为Q2,R1,R2和R3优选的或特别优选的定义的那些定义。
式(Ⅲ)的起始物是已知的和/或能通过本身已知的方法制备(参见EP 385775,DE4322067，制备实施例)。
式(Ⅳ)提供了在制备通式(Ⅰ)化合物的本发明方法(b)中用作起始物的三唑啉(硫)酮的一般定义。在式(Ⅳ)中，Q1,Q2,R4和R5各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为Q1,Q2,R4和R5优选的或特别优选的定义的那些定义；Z优选代表氟，氯，溴，甲氧基，乙氧基，苄氧基，苯氧基，卤素-或硝基-苯氧基，特别是甲氧基，苯氧基或4-硝基-苯氧基。
式(Ⅳ)的起始物是已知的和/或能通过本身已知的方法制备(参见EP341489,EP422469,EP425948,EP431291,EP507171,EP534266)。
式(Ⅴ)提供了制备通式(Ⅰ)化合物的本发明方法(b)中也用作起始物的磺酰胺的一般定义。在式(Ⅴ)中，R1,R2和R3各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为R1,R2和R3优选的或特别优选的定义的那些定义。
式(Ⅴ)起始物是已知的和/或能通过本身已知的方法制备
(参见J.Med Chem.15(1971),432-439；J.Chem.Soc.；Perkin Trans I 1974,2451-2458；Justus Liebigs Ann.Chem.1977,1787-1798；Chem.Pharm.Bull.27(1979),1287-1298；Synthesis 1981,35-36；《药物化学杂志》33(1990),1721-1728；EP385775；制备实施例)。
式(Ⅵ)提供了在制备式(Ⅰ)化合物的本发明方法(c)中用作起始物的磺酰胺衍生物的一般定义。在式(Ⅵ)中，Q2,R1,R2和R3各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为Q2,R1,R2和R3优选的或特别优选的定义的那些定义；Z优选代表氟，氯，溴，甲氧基，苯氧基，苄氧基或苯氧基，特别是甲氧基或苯氧基。
式(Ⅵ)起始物是已知的和/或能通过本身已知的方法制备。
式(Ⅶ)提供了在制备式(Ⅰ)化合物的本发明方法(d)中用作起始物的磺酰卤的一般定义。在式(Ⅶ)中，R1,R2和R3各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为R1,R2和R3优选的或特别优选的定义的那些定义；X优选代表氟，氯或溴，特别是氯。
式(Ⅶ)的起始物是已知的和/或能通过本身已知的方法制备。
制备新的式(Ⅰ)化合物的本发明方法(a),(b),(c)和(d)优选使用稀释剂进行。合适的稀释剂实质上是所有惰性有机溶剂。优选包括脂肪族和芳香族的，任选卤化的烃，例如戊烷，己烷，庚烷，环己烷，石油醚，汽油，里格罗因，苯，甲苯，二甲苯，二氯甲烷，氯化乙烯，氯仿，四氯化碳，氯苯和邻二氯苯；醚类，例如乙醚，二丁基醚，乙二醇二甲基醚和二甘醇二甲基醚，四氢呋喃和二噁烷；酮类，例如丙酮，甲基乙基酮，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，还有二甲亚砜，四亚甲基砜和六甲基磷三酰胺。
用于本发明方法(a),(b),(c)和(d)的合适的反应助剂或酸受体是常规用于这样的反应的所有酸结合剂。优选碱金属氢氧化物，例如氢氧化钠或氢氧化钾，碱土金属氢氧化物，例如氢氧化钙，碱金属碳酸盐和烷氧化物，例如碳酸钠和碳酸钾，叔丁醇钠和叔丁醇钾，还有碱性氮化合物例如三甲胺，三乙胺，三丙胺，三丁基胺，二异丁基胺，二环己基胺，乙基二异丙基胺，乙基二环己基胺，N,N-二甲基苄基胺，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]-十一-7-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)的反应温度可以在相当宽的范围内变化。一般情况下，反应在-20℃和+100℃之间的温度下进行，优选在0℃和+80℃之间的温度下进行。
本发明方法(a),(b),(c)和(d)一般在大气压下进行。但是也可以在高压或低压下操作。
在实施本发明方法(a),(b),(c)和(d)时，各种情况下一般以大约等摩尔量使用起始物。但是，各种情况下也可以以相对大的过量使用其中之一起始物成分。反应一般在合适的酸受体的存在下在合适的稀释剂中进行，并且反应混合物在需要的特定温度下搅拌数小时。各种情况下通过常规方法进行本发明方法(a),(b),(c)和(d)的后处理(参见制备实施例)。
如果需要，可以制备本发明通式(Ⅰ)化合物的盐。通过形成盐的常规方法以简单的方式获得这样的盐，例如通过将式(Ⅰ)化合物溶解于或分散于合适的溶剂，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。然后，如果需要，经延长时间的搅拌后，通过浓缩或吸滤分离盐。
本发明活性化合物可以用作脱叶剂，干燥剂，杀稻草剂，特别是作为杀杂草剂。从广义上说，所谓杂草应理解是在其所不期望的地点生长的所有植物。本发明物质是作为灭生性除草剂还是选择性除草剂主要取决于使用的量。
例如与下面的植物相关，可以使用本发明活性化合物：
双子叶杂草种类：芥属(Sinapis)，独行菜属(Lepidium)，猪殃殃属(Galium)，繁缕属(Stellaria)，母菊属(Matricaria)，春黄菊属(Anthemis)，辣子草(Galinsoga)，藜属(Chenopodium)，荨麻属(Urtica)，千里光属(Senecio)，苋属(Amaranthus)，马齿苋属(Portulaca)，苍耳属(Xanthium)，旋花属(Convolvulus)，甘薯属(Ipomoea)，蓼属(Polygonum)，田菁(Sesbania)，豚草属(Ambrosia)，蓟属(Cirsium)，飞廉属(Carduus)，苦苣菜属(Sonchus)，茄属(Solanum)，焊菜属(Rorippa)，水松叶属(Rotala)，母草属(Lindernia)，野芒麻属(Lamium)，婆婆纳属(Veronica)，苘麻属(Abutilon)，刺果(Emex)，曼陀罗属(Datura)，堇菜属(Viola)，鼬瓣花属(Galeopsis)，罂粟属(Papaver)，矢车菊属(Centaurea)，车轴草属(Trifolium)，毛莨属(Ranunculus)和蒲公英属(Taraxacum)。
双子叶作物种类：棉属(Gossypium)，大豆属(Glycine),Beta，胡萝卜属(Daucus)，菜豆属(Phaseolus),Pisum，茄属(Solanum)，亚麻属(Linum)，甘薯属(Ipomoea)，巢菜属(Vicia)，烟草属(Nicotiana)，番茄属(Lycopersicon)，花生(Arachis)，芥属(Brassica)，莴苣属(Lactuca)，香瓜属(Cucumis)，和臭瓜(Cucurbita)。
单子叶杂草种类：稗属(Echinochloa)，狗尾草属(Setaria)，黍属(Panicum)，马唐属(Digitaria)，梯牧属(Phleum)，早熟禾属(Poa)，羊茅属(Festuca)，蟋蟀菜属(Eleusine)，臂形草属(Brachiaria)，黑麦草属(Lolium)，雀麦属(Bromus)，燕麦属(Avena)，莎草属(Cyperus)，蜀黍属(Sorghum)，冰草属(Agropyron),Cycnodon，雨久花属(Monchoria)，飘拂草属(Fimbristylis)，慈姑(Sagittaria)，荸荠属(Eleocharis)，镳草(Scirpus)，雀稗草(Paspalum),Ischaemum，尖瓣花属(Sphenoclea)，龙爪茅属(Dactyloctenium)，剪股颍属(Agrostis)，看麦娘属(Alopecurus)和Apera。
单子叶作物种类：稻属(Oryza)，玉米属(Zea)，小麦属(Triticum)，大麦属(Hordeum)，燕麦属(Avena)，黑麦属(Secale)，蜀黍属(Sorghum)，黍属(Panicum)，甘蔗(Saccharum)，凤梨属(Ananas)，天门冬属(Asparagus)和葱属(Allium)。
但是，本发明活性化合物的用途不受这些种类的限制，而是以相同的方式扩展到其它植物。
根据浓度，本发明化合物适于例如在工业场所和铁道，有或没有树木的路或广场上全部控制杂草。这些化合物同样也被用来在多年生种植作物场所，草坪，运动场和牧场控制杂草，所述多年生种植作物场所例如树林，装饰性种植的树，果园，葡萄园，柠檬园，坚果园，香蕉种植园，咖啡种植园，茶种植园，橡胶种植园，油棕种植园，可可种植园，软果种植植物和蛇麻草田，以及用来在年生种植作物场所选择性控制杂草。
本发明式(Ⅰ)化合物特别适用于在芽前和芽后选择性控制单子叶农作物中单子叶和双子叶杂草。
活性化合物可以配制成常规制剂，例如溶液、乳剂、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、和浸有活性化合物的天然和合成材料以及包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产，例如，将活性化合物与扩充剂即液体溶剂和/或固体载体混合，并任选使用表面活性剂，即乳化剂和/或分散剂和/或起泡剂。
用水作扩充剂的情况下，也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有：芳香族化合物，如二甲苯，甲苯或烷基萘，氯代芳香族化合物和氯代脂肪烃，如氯代苯类、氯乙烯类或二氯甲烷，脂肪烃，如环己烷或石蜡，例如矿物油馏份，矿物油和植物油，醇类，如丁醇或乙二醇以及其醚和酯，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亚砜，以及水。
合适的固体载体是：例如铵盐，磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和磨碎的合成矿物质，如研细的二氧化硅、矾土和硅酸盐；用于颗粒剂的适合的固体载体有：例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石，以及有机和无机粉的合成颗粒，和如下有机物的颗粒：例如锯木屑、椰壳、玉米穗轴和烟茎；适合的乳化剂和/或起泡剂有：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，芳基磺酸盐以及蛋白水解产物；适合的分散剂有：例如，木素亚硫酸废液和甲基纤维素。
制剂中，可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物，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，和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂，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，和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下，制剂含有0.1-95％重量的活性化合物，优选0.5-90％。
对于控制杂草，本发明活性化合物或其制剂形式也可以作为与已知除草剂的混合物使用，可以是即用型制剂或容器混合物。
用于所述混合物的可能成分是已知的除草剂，例如N-酰苯胺类，例如吡氟草胺和敌稗；芳基羧酸类，例如二氯吡啶甲酸，麦草畏和毒莠定；芳基氧基链烷酸类，例如2,4-滴，2,4-滴丁酸，2,4-滴丙酸，氟草烟，2甲4氯，2甲4氯丙酸和绿草定；芳基氧基苯氧基链烷酸酯类，例如禾草灵，噁唑禾草灵，吡氟禾草灵，吡氟氯禾灵和喹禾灵；吖嗪酮类，例如杀草敏和哒草伏；氨基甲酸酯类，例如氯苯胺灵，甜菜安，甜菜宁和苯胺灵；氯代N-乙酰苯胺类，例如甲草胺，乙草安，丁草安，吡草安，异丙甲草胺，丙草安和毒草安；二硝基N-酰苯胺类，例如安磺灵，二甲戊乐灵和氟乐灵；二苯基醚类，例如三氟羧草醚，甲羧除草醚，乙羧氟草醚，氟磺胺草醚，halosafen，乳氟禾草灵和乙氧氟草醚；脲类，例如氯麦隆，敌草隆，伏草隆，异丙隆，利谷隆和甲基苯噻隆；羟胺类，例如禾草灭，烯草酮，噻草隆，稀禾定和肟草酮；咪唑啉酮类，例如咪草烟，咪草酯，灭草烟和灭草喹；腈类，例如溴苯腈，敌草腈和碘苯腈；氧乙酰胺类，例如苯噻草胺；磺酰脲类，例如amidosulfuron，苄嘧黄隆，氯嘧黄隆，氯黄隆，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，例如克草猛，灭草特，燕麦畏，茵达灭，禾草畏，草达灭，苄草丹，杀草丹和野燕畏；三嗪类，例如莠去津，氰草津，西玛津，西草净，特丁净和terbutylazine；三嗪酮类，例如环嗪酮，苯嗪草酮和嗪草酮；其它类，例如氨基三唑，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，草铵膦，草甘膦，isoxaben，哒草特，二氯喹啉酸，喹草酸，草硫磷和灭草环。
也可能是与其它已知活性化合物的混合物，所述其它活性化合物例如杀真菌剂，杀昆虫剂，杀螨剂，杀线虫剂，鸟驱避剂，植物营养剂和改善土壤结构的试剂。
这些活性化合物可以以本身，其制剂形式，或者以通过进一步稀释而从中制备的使用形式使用，例如即用型溶液，混悬剂，乳剂，粉剂，糊剂和颗粒剂。它们可以以常规方式使用，例如通过浇灌，喷雾，弥雾或播撒。
本发明活性化合物可以在植物芽前或芽后施用。其也可以在播种前直接掺合到土壤中。
使用的活性化合物的量可以在一个基本的范围内变化。这主要取决于期望的效果的性质。一般情况下，使用的量在每公顷土壤面积使用1g-10kg活性化合物，优选每公顷土壤面积使用5g-2kg活性化合物。
根据下面的实施例可以明了本发明活性化合物的制备和应用。
制备实施例
实施例1
(方法(b))
首先将3.4g(15mmol)2-吡咯烷子基-苯磺酰胺加入到100ml乙腈中，加入3.9g(15mmol)5-乙氧基-4-甲基-2-苯氧羰基-2,4-二氢-3H-1,2,4-三唑-3-酮，然后加入1.7g(15mmol)叔丁醇钾，接着反应混合物在室温下(大约20℃)搅拌15小时。然后用水泵抽真空浓缩混合物，残余物与50ml水混合。混合物用浓盐酸酸化至pH2，然后每次用50ml二氯甲烷萃取两次。用硫酸镁干燥合并的有机相后过滤。水泵抽真空浓缩滤液，残余物与乙醚搅拌，吸滤分离结晶产物。
得到2.0g(理论量的34％)5-乙氧基-4-甲基-2-(2-吡咯烷子基-苯基-磺酰基氨基羰基)-2,4-二氢-3H-1,2,4-三唑-3-酮，熔点，68℃。
实施例2
(方法(b))
首先将1.4g(6mmol)2-正丁基氨基-苯磺酰胺加入到100ml乙腈中，并与1.6g(6mmol)4-甲基-5-甲基硫基-2-苯氧羰基-2,4-二氢-3H-1,2,4-三唑-3-酮和1.0g(6.6mmol)二氮杂双环十一烯(DBU)混合，混合物在室温下(大约20℃)搅拌15小时，然后用水泵抽真空浓缩，残余物与水混合，用浓盐酸酸化至pH1，并且每次用50ml二氯甲烷萃取两次。用水洗涤合并的有机相，用硫酸镁干燥后过滤。水泵抽真空浓缩滤液，残余物溶解于乙醚，吸滤分离结晶产物。
得到0.8g(理论量的34％)2-(2-正丁基氨基-苯基磺酰基-氨基羰基)-4-甲基-5-甲基硫基-2,4-二氢-3H-1,2,4-三唑-3-酮，熔点120℃。
类似于实施例1或2，并根据本发明制备方法的一般性说明，也能制备例如下面表1中列出的式(Ⅰ)化合物。
(Ⅰ)表1：式(Ⅰ)化合物的实施例(位置)Ex.No. Q1 Q2 R1 R2 R3 R4 R5 熔点(℃)3 O O H H (6-)CH3 CH3 OC2H54 O O H -COCH3 H CH3 OC2H5 1405 O O H -COCH3 H CH3 C2H5 1206 O O H -COCH3 H CH3 SCH3 1227 O O -COC2H5 -COC2H5 H CH3 OC2H5 1208 O O -COC2H5 -COC2H5 H CH3 C2H5 989 O O H H H CH3 SCH3 13310 O O H H H CH3 OC2H5 14211 O O H H H CH3 C2H5 19012 O O H H (5-)Br CH3 OC2H5 12713 O O -(CH2)4- H CH3 SCH3 12014 O O -(CH2)4- H CH3 C2H5 10215 O O -(CH2)4- (5-)NO2 CH3 SCH3 15716 O O -(CH2)4- (5-)NO2 CH3 OC2H5 15617 O O -(CH2)4- (5-)NO2 CH3 C2H5 13818 O O -(CH2)4- (5-)NO2 CH3 CH2OCH3 15019 O O -(CH2)4- (5-)NO2 CH3 SC2H5 12520 O O -(CH2)4- (5-)NO2 CH3 n-C3H7 16021 O O -(CH2)2-O-(CH2)2- H CH3 SCH3 15622 O O -(CH2)2-O-(CH2)2- H CH3 C2H5 15823 O O -(CH2)2-O-(CH2)2- H CH3 OC2H5 19224 O O -(CH2)2-O-(CH2)2- (5-)NO2 CH3 5CH3 17225 O O -(CH2)2-O-(CH2)2- H CH3 n-C3H7 18226 O O -(CH2)2-O-(CH2)2- H CH3 SC2H5 122
表1-续
表1-续
表1-续(位置)Ex.No. Q1 Q2 R1 R2 R3 R4 R5 熔点(℃)67 O O H H H CH3 SCH3
(K盐)68 O O H C2H5 H CH3 OC2H5 13269 O O H C2H5 H CH3 SCH3 15370 O O H H (6-)Cl CH3 C2H5 20871 O O H H (6-)Cl CH3 OCH3 20272 O O H H (6-)CH3CH3 SCH3 198
式(Ⅴ)起始物
实施例(Ⅴ-1)
步骤：
首先将56ml异氰酸氯代磺酰酯加入到250ml硝基乙烷中，并冷却到-10℃。然后滴加93.7g(0.63mol)N-丁基苯胺，同时内部温度保持在-10℃。混合物在-10℃搅拌大约30分钟。然后在大约+15℃，一次加一点地加入93g(0.7mol)三氯化铝，同时用冰浴冷却。接着将混合物倒入冰水，并用浓盐酸调至pH1。吸滤分离结晶产物。
得到102g(理论量的64％)4-正丁基-1,2,3,4-四氢-1,2,4-苯并噻二嗪-3-酮1,1-二氧化物。
步骤2
102g(0.04mol)4-正丁基-1,2,3,4-四氢-1,2,4-苯并噻二嗪-3-酮1,1-二氧化物与500ml 50％强度硫酸混合，混合物在回流下加热直到获得澄清溶液。混合物冷却到室温(大约20℃)，倒入水中，并用浓氢氧化钠水溶液中和。吸滤分离结晶产物，并用甲苯共沸去水。得到55.1g(理论量的60％)2-正丁基氨基-苯磺酰胺。实施例(Ⅴ-2)
将28.2g(0.16mol)2-氟-苯磺酰胺和32g(0.45mol)吡咯烷的混合物在回流下加热3小时。接着用水泵抽真空浓缩混合物，残余物与200ml水搅拌大约15小时。然后加入10ml浓盐酸，吸滤分离结晶产物。
得到20.7g(理论量的61％)2-吡咯烷子基-苯磺酰胺，熔点78℃。
应用实施例
实施例A
芽前试验
溶剂：5份重量丙酮
乳化剂：1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂，将1份重量活性化合物与所述量溶剂混合，加入所述量乳化剂，用水将乳油稀释到需要的浓度。
在正常土壤中播种试验植物的种子。大约24小时后，用活性化合物制剂对土壤喷雾。有益的是，每单位面积用的水的量保持不变。制剂中活性化合物的浓度并不重要，只有每单位面积施用的活性化合物的量是重要的。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。
数据说明：
0％=没有效果(象未处理对照物一样)
100％=完全破坏
在该项试验中，例如本发明制备实施例3,23,49,50,60和68的本发明化合物显示出强的除草活性(参见表A-1至A-5)，并且农作物例如小麦和玉米对其中的一些有好的耐受性。
“ai.”=“活性成分”表A：芽前试验/温室表A-1化合物的制 施用比例 小麦 棉花 看麦 莎草 早熟禾 母菊备实施例 娘属编号 (gai./ha)(3) 60 0 0 95 80 80 80表A-2化合物的制 施用比例 小麦 大豆 莎草 狗尾草 茄属 苍耳备实施例编号 (gai/ha)(23) 125 20 0 90 80 80 90表A-3化合物的制 施用比例 小麦 大豆 向日葵 看麦娘 稗 苋属 藜备实施例编号 (gai/ha)
(50) 125 0 20 - 95 80 80 95
(60) 250 20 - 20 80 80 95 80表A-4化合物的制 施用比例 玉米 棉花 看麦娘 猪殃殃 母菊备实施例编号 (gai./ha)(49) 125 0 0 90 90 95(50) 125 0 20 95 95 90表A-5化合物的制 施用比例 看麦娘 狗尾草 苋属 辣子草 芥属备实施例编号 (gai./ha)(68) 125 95 95 95 95 95
实施例B
芽后试验
溶剂：5份重量丙酮
乳化剂：1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂，将1份重量活性化合物与所述量溶剂混合，加入所述量乳化剂，用水将乳油稀释到需要的浓度。
用活性化合物制剂对高5-15cm的试验植物喷雾，使对每单位面积施用一定量的期望的活性化合物。选择喷雾液的浓度，使在每种情况下以1000L水/公顷施用期望的活性化合物的特定量。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。
数据说明：
0％=没有效果(象未处理对照物一样)
100％=完全破坏
在该项试验中，例如制备实施例71的本发明化合物显示出强的除草活性(参见表B)。表B：芽后试验/温室化合物的制 施用比例 小麦 向日葵 燕麦 蜀黍属 苋属 茄属备实施例编号 (gai./ha)(71) 125 10 10 80 80 90 90
Claims (8)
1．通式(Ⅰ)的取代的芳基磺酰基氨基(硫代)羰基-三唑啉(硫)酮
(Ⅰ)
其中
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，氨基或代表各自任选被取代的烷基，烷氧基，烷基羰基，烷氧羰基，烷硫基，烷基亚磺酰基，烷基磺酰基，链烯基，炔烃基或亚烷基氨基，
R2代表氢或代表各自任选被取代的烷基，烷基羰基，烷氧羰基，烷基磺酰基，链烯基，或炔烃基，或者与R1一起代表任选插入氧原子和/或任选被取代的链烷二基，
R3代表氢，氰基，硝基，卤素或代表各自任选被取代的烷基，烷基羰基或烷氧羰基，
R4代表氢，羟基，氨基，亚烷基氨基或者代表各自任选被取代的选自下面的基团：烷基，链烯基，炔烃基，烷氧基，链烯基氧基，烷基氨基，二烷基氨基，环烷基，环烷基烷基，环烷基氨基，芳基，芳基烷基，和
R5代表氢，羟基，巯基，氨基，氰基，卤素，或者代表各自任选被取代的选自下面的基团：烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，链烯基，炔烃基，链烯基氧基，炔烃基氧基，链烯基硫基，炔烃基硫基，链烯基氨基，炔烃基氨基，环烷基，环烷基氧基，环烷基硫基，环烷基氨基，环烷基烷基，芳基，芳基氧基，芳基硫基，芳基氨基，芳基烷基，
以及式(Ⅰ)化合物的盐。
2．权利要求1的式(Ⅰ)化合物，特征在于
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，氨基，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷氧基，烷基羰基，烷氧羰基，烷硫基，烷基亚磺酰基，或烷基磺酰基，或者代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基，炔烃基或亚烷基氨基，
R2代表氢，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷基羰基，烷氧羰基或烷基磺酰基，代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基或炔烃基，或与R1-起代表具有2-6个碳原子的可任选插入氧原子和/或任选被卤素或C1-C4-烷基-取代的链烷二基，
R3代表氢，氰基，硝基，卤素或者代表各自任选被卤素-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷基羰基或烷氧羰基，
R4代表氢，羟基，氨基，C1-C6-亚烷基氨基，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，代表各自任选被氟-，氯-和/或溴-取代的C2-C6-链烯基或C2-C6-炔烃基，代表C1-C6-烷基氧基或C3-C6-链烯基氧基，代表各自任选被氟-和/或氯-取代的C1-C6-烷基氨基，二-(C1-C4-烷基)-氨基或C1-C4-烷酰基氨基，代表各自任选被氟-，氯-，溴-和/或C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基，或者代表各自任选被氟-，氯-，溴-，氰基-，硝基-，C1-C4-烷基-，三氟甲基-，C1-C4-烷氧基-和/或C1-C4-烷氧羰基-取代的苯基或苯基-C1-C4-烷基，和
R5代表氢，羟基，巯基，氨基，氰基，卤素，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的各种情况下在烷基中具有1-6个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-或卤素-取代的各种情况下具有2-6个碳原子的链烯基，炔烃基，链烯基氧基，炔烃基氧基，链烯基硫基，炔烃基硫基，链烯基氨基或炔烃基氨基，代表各自任选被氰基-，卤素-或C1-C4-烷基-取代的各种情况下在环烷基中具有3-6个碳原子的环烷基，环烷基氧基，环烷基硫基，环烷基氨基或环烷基-C1-C4-烷基，或者代表各自任选被氰基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基-或C1-C4-卤代烷氧基-取代的苯基，苯氧基，苯硫基，苯基氨基或苯基-C1-C4-烷基，
和式(Ⅰ)化合物的钠盐，钾盐，镁盐，钙盐，铵盐，C1-C4-烷基-铵盐，二-(C1-C4-烷基)-铵盐，三-(C1-C4-烷基)-铵盐，四-(C1-C4-烷基)-铵盐，三-(C1-C4-烷基)-锍，C5-或C6-环烷基铵盐和二-(C1-C2-烷基)-苄基-铵盐。
3．权利要求1的式(Ⅰ)化合物，特征在于，
Q1代表氧或硫，
Q2代表氧或硫，
R1代表氢，代表各自任选被氰基-，氟-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，甲氧基，乙氧基，正丙氧基，异丙氧基，乙酰基，丙酰基，正-或异-丁酰基，甲氧羰基，乙氧羰基，正-或异-丙氧羰基，甲基硫基，乙基硫基，正-或异-丙基硫基，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，代表丙烯基，丁烯基，丙炔基或丁炔基或者代表亚丙基氨基，
R2代表氢，代表各自任选被氰基-，氟-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，乙酰基，丙酰基，正-或异-丁酰基，代表甲氧羰基，乙氧羰基，正-或异-丙氧羰基，甲基磺酰基，乙基磺酰基，正-或异-丙基磺酰基，代表丙烯基，丁烯基，丙炔基或丁炔基，或者与R1一起代表任选被甲基-和/或乙基-取代的乙烷-1,2-二基，丙烷-1,3-二基，丁烷-1,4-二基，戊烷-1,5-二基，或3-氧代-戊烷-1,5-二基，
R3代表氢，代表氰基，硝基，氟，氯，溴，或代表各自任选被氟-取代的甲基，乙基，正丙基或异丙基，
R4代表氢，代表各自任选被氟-，氯-，氰基-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，代表各自任选被氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基或丁炔基，代表甲氧基，乙氧基，正-或异-丙氧基或者代表烯丙基氧基，代表甲基氨基，乙基氨基，正-或异-丙基氨基，正-、异-、仲-或叔-丁基氨基，二甲基氨基或二乙基氨基，代表各自任选被氟-，氯-，溴-，甲基-或乙基-取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，或者代表任选被氟-，氯-，溴-，氰基-，甲基-，三氟甲基或甲氧基-取代的苄基或苯基，和
R5代表氢，羟基，巯基，氨基，氟，氯，溴，代表各自任选被氟-，氯-，氰基-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，正-、异-、仲-或叔-丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲-或叔-丁基氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，正-、异-、仲-或叔-丁基硫基，甲基氨基，乙基氨基，正-或异-丙基氨基，正-、异-、仲-或叔-丁基氨基，二甲基氨基或二乙基氨基，代表各自任选被氰基-，氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基，丁炔基，丙烯基氧基，丁烯基氧基，丙炔基氧基，丁炔基氧基，丙烯基硫基，丁烯基硫基，丙炔基硫基，丁炔基硫基，丙烯基氨基，丁烯基氨基，丙炔基氨基或丁炔基氨基，代表各自任选被氰基-，氟-，氯-，溴-，甲基-或乙基-取代的环丙基，环丁基，环戊基，环己基，环丙基氧基，环丁基氧基，环戊基氧基，环己基氧基，环丙基硫基，环丁基硫基，环戊基硫基，环己基硫基，环丙基氨基，环丁基氨基，环戊基氨基，环己基氨基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，或者代表各自任意被氰基-，氟-，氯-，甲基-，三氟甲基-，甲氧基-或甲氧羰基-取代的苯基，苯氧基，苯基硫基，苯基氨基或苄基。
4．制备权利要求1的式(Ⅰ)化合物的方法，特征在于
(a)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅲ)的异(硫代)氰酸磺酰酯反应，
(Ⅱ)其中Q1,R4和R5各自如权利要求1所定义，
(Ⅲ)
其中
Q2,R1,R2和R3各自如权利要求1所定义，
或者
(b)如果适当在酸受体存在下和如果适当在稀释剂存在下，通式(Ⅳ)的三唑啉(硫)酮衍生物与通式(Ⅴ)的磺酰胺反应，
(Ⅳ)其中Q1,Q2,R4和R5各自如上定义，Z代表卤素，烷氧基，芳烷氧基或芳基氧基，
(Ⅴ)
其中
R1,R2和R3各自如上定义，
或者
(c)如果适当在酸受体存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅵ)的磺酰胺衍生物反应，(Ⅱ)其中Q1,R4和R5各自如上定义，
(Ⅵ)
其中
Q2,R1,R2和R3各自如上定义，
Z代表卤素，烷氧基，芳烷氧基或芳基氧基，
(d)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的三唑啉(硫)酮与通式(Ⅶ)的磺酰卤和通式(Ⅷ)的(硫代)氰酸金属盐反应，
(Ⅱ)其中Q1,R4和R5各自如上定义，(Ⅶ)其中R1,R2和R3各自如上定义，X代表卤素，MQ2CN (Ⅷ)其中Q2如上定义，和M代表碱金属或碱土金属等价物，
并且如果适当，将由方法(a),(b),(c)或(d)得到的式(Ⅰ)化合物通过常规方法转化为盐。
5．除草组合物，特征在于其含有至少一种权利要求1的式(Ⅰ)化合物。
6．权利要求1的通式(Ⅰ)化合物控制不期望植物生长的用途。
7．防治杂草的方法，其特征在于使权利要求1的通式(Ⅰ)化合物作用于杂草或其生长地域。
8．制备除草组合物的方法，其特征在于将权利要求1的通式(Ⅰ)化合物与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19609059A DE19609059A1 (de) | 1996-03-08 | 1996-03-08 | Substituierte Arylsulfonylamino(thio)carbonyl-triazolin(thi)one |
| DE19609059.8 | 1996-03-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1218468A true CN1218468A (zh) | 1999-06-02 |
| CN1079398C CN1079398C (zh) | 2002-02-20 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97194464A Expired - Fee Related CN1079398C (zh) | 1996-03-08 | 1997-02-24 | 作为除草剂的取代的芳基磺酰基氨基(硫代)羰基－三唑啉(硫)酮 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6200934B1 (zh) |
| EP (1) | EP0888342A1 (zh) |
| JP (1) | JP2000506147A (zh) |
| KR (1) | KR19990087530A (zh) |
| CN (1) | CN1079398C (zh) |
| AU (1) | AU705366B2 (zh) |
| BR (1) | BR9707850A (zh) |
| CA (1) | CA2248285A1 (zh) |
| DE (1) | DE19609059A1 (zh) |
| HK (1) | HK1020055A1 (zh) |
| WO (1) | WO1997032876A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE1012386A3 (fr) * | 1999-01-15 | 2000-10-03 | Univ Liege | Derives de sulfonamides benzeniques et leurs utilisations. |
| US20070213841A1 (en) * | 2001-03-30 | 2007-09-13 | Townsend Barry W | Prosthetic foot with tunable performance |
| US8574314B2 (en) * | 2003-09-30 | 2013-11-05 | Bioquest Prosthetics Llc | Resilient prosthetic and orthotic components which incorporate a plurality of sagittally oriented struts |
| US7066792B2 (en) * | 2004-08-06 | 2006-06-27 | Micron Technology, Inc. | Shaped polishing pads for beveling microfeature workpiece edges, and associate system and methods |
| ES2594874T3 (es) * | 2004-11-18 | 2016-12-23 | Synta Pharmaceuticals Corp. | Compuestos de triazol que modulan la actividad de HSP90 |
| EP1717228A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Sulfonylamino(thio)carbonylverbindungen als Herbizide oder Pflanzenwachstumsregulatoren |
| JP5118039B2 (ja) | 2005-08-18 | 2013-01-16 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０活性を調節するトリアゾール化合物 |
| AU2007267852A1 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate Hsp90 activity and methods for identifying same |
| 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 |
| AU2012332421A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of Hsp90 inhibitors with topoisomerase I inhibitors |
| US9402831B2 (en) | 2011-11-14 | 2016-08-02 | Synta Pharmaceutical Corp. | Combination therapy of HSP90 inhibitors with BRAF inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5085684A (en) * | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| 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 |
| US5057144A (en) * | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
-
1996
- 1996-03-08 DE DE19609059A patent/DE19609059A1/de not_active Withdrawn
-
1997
- 1997-02-24 BR BR9707850A patent/BR9707850A/pt not_active IP Right Cessation
- 1997-02-24 US US09/142,272 patent/US6200934B1/en not_active Expired - Fee Related
- 1997-02-24 JP JP9531405A patent/JP2000506147A/ja active Pending
- 1997-02-24 KR KR1019980706965A patent/KR19990087530A/ko not_active Application Discontinuation
- 1997-02-24 EP EP97906119A patent/EP0888342A1/de not_active Withdrawn
- 1997-02-24 WO PCT/EP1997/000878 patent/WO1997032876A1/de not_active Application Discontinuation
- 1997-02-24 AU AU20928/97A patent/AU705366B2/en not_active Ceased
- 1997-02-24 CN CN97194464A patent/CN1079398C/zh not_active Expired - Fee Related
- 1997-02-24 CA CA002248285A patent/CA2248285A1/en not_active Abandoned
-
1999
- 1999-11-16 HK HK99105291A patent/HK1020055A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1079398C (zh) | 2002-02-20 |
| EP0888342A1 (de) | 1999-01-07 |
| WO1997032876A1 (de) | 1997-09-12 |
| US6200934B1 (en) | 2001-03-13 |
| KR19990087530A (ko) | 1999-12-27 |
| DE19609059A1 (de) | 1997-09-11 |
| CA2248285A1 (en) | 1997-09-12 |
| JP2000506147A (ja) | 2000-05-23 |
| AU705366B2 (en) | 1999-05-20 |
| BR9707850A (pt) | 1999-07-27 |
| AU2092897A (en) | 1997-09-22 |
| HK1020055A1 (en) | 2000-03-10 |
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