CN1576274A - 用作除草剂的取代的芳基磺酰基(硫代)脲类 - Google Patents
用作除草剂的取代的芳基磺酰基(硫代)脲类 Download PDFInfo
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- CN1576274A CN1576274A CNA2004100699417A CN200410069941A CN1576274A CN 1576274 A CN1576274 A CN 1576274A CN A2004100699417 A CNA2004100699417 A CN A2004100699417A CN 200410069941 A CN200410069941 A CN 200410069941A CN 1576274 A CN1576274 A CN 1576274A
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- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
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- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A—HUMAN NECESSITIES
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- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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Abstract
本发明涉及新的取代的芳基磺酰基(硫代)脲类及其盐类，其中A代表氮原子或CH基团，Q代表氧原子或硫原子，R1代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，R2代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，R3代表氢原子或者任选被取代的烷基，R4代表各自任选被取代的烷基，烷氧基，链烯基，炔基，链烯基氧基，炔基氧基，环烷基，环烷基氧基或环烷基烷基，和R5代表氢原子，甲酰基或者各自任选被取代的烷基，烷基羰基，烷氧基羰基，烷基磺酰基，链烯基，炔基，环烷基，环烷基羰基，环烷基磺酰基，或杂环基，但排除化合物N－(4，6－二甲基－嘧啶－2－基)－N′－[2－(1，1，2，2－四氟－乙氧基)－6－甲基－苯基磺酰基]－脲，并且涉及制备这些新的化合物的方法，以及涉及其作为除草剂的用途。
Description
本申请是1997年2月20日提交的发明创造名称为“用作除草剂的取代的芳基磺酰基(硫代)脲类”的中国专利申请(国家申请号为No.97192820.7，国际申请号为PCT/EP97/00798)的分案申请。
本发明涉及新的取代的芳基磺酰基(硫代)脲类，其制备方法，以及其作为除草剂的用途。
已知一些取代的磺酰基脲类具有除草性质(参见DE 2715786，EP1514，EP 23422)。但是，这些化合物的除草活性和农作物安全性并不是在所有方面令人满意。
因此，本发明提供通式(I)的新的取代的芳基磺酰基(硫代)脲类：
其中
A代表氮原子或CH基团，
Q代表氧原子或硫原子，
R1代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，
R2代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，
R3代表氢原子或者任选被取代的烷基，
R4代表各自任选被取代的烷基，烷氧基，链烯基，炔基，链烯基氧基，炔基氧基，环烷基，环烷基氧基或环烷基烷基，和
R5代表氢原子，甲酰基或者各自任选被取代的烷基，烷基羰基，烷氧基羰基，烷基磺酰基，链烯基，炔基，环烷基，环烷基羰基，环烷基磺酰基，或杂环基，
以及式(I)化合物的盐，
除了权利要求中已排除的现有技术化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲(参见EP 23422)。
当进行下面的反应时会得到通式(I)新的取代的芳基磺酰基(硫代)脲类：
(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)的氨基吖嗪
其中
A，R1和R2各自如上定义，
与通式(III)的异(硫代)氰酸芳基磺酰基酯反应
其中
Q，R4和R5各自如上定义，
或者
(b)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(IV)的取代的氨基吖嗪
其中
A，Q，R1和R2各自如上定义，
Z代表卤原子，烷氧基或芳氧基，以及
R3如上定义或者代表基团-C(Q)-Z
与通式(V)的芳烃磺酰胺反应
其中
R4和R5各自如上定义，
或者
(c)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)的氨基吖嗪
其中
A，R1和R2各自如上定义，
与通式(VI)的取代的芳烃磺酰胺反应
其中
Q，R4和R5各自如上定义，
Z代表卤原子，烷氧基或芳氧基，以及
如果合适，通过常规方法，将方法(a)，(b)和(c)获得的式(I)化合物转化成盐。
通式(I)的新的取代的芳基磺酰基(硫代)脲类具有强的除草活性。
本发明优选提供下列式(I)化合物，其中
A代表氮原子或CH基团，
Q代表氧原子或硫原子，
R1代表氢原子，卤原子，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-4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，卤原子，C1-C4烷基或C1-C4烷氧基取代的在各种情况下有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基氧基，呋喃基氧基或四氢呋喃基氧基。
R2代表氢原子或卤原子，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-4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，卤原子，C1-C4烷基或C1-C4烷氧基取代的在各种情况下有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基氧基，呋喃基氧基或四氢呋喃基氧基，
R3代表氢原子或任选被C1-C4烷氧基，C1-C4烷基羰基或C1-C4烷氧基羰基取代的具有1-4个碳原子的烷基，
R4代表各自任选被氰基卤原子，或C1-C4烷氧基取代的在各种情况下在烷基部分有1-6个碳原子的烷基或烷氧基，代表各自任选被卤原子取代的在各种情况下链烯基或炔基基团具有2-6个碳原子的链烯基，炔基，链烯基氧基或炔基氧基，或者代表各自任选被氰基，卤原子或C1-C4烷基取代的在各种情况下环烷基基团具有3-6个碳原子并且任选地烷基部分具有1-4个碳原子的环烷基，环烷基氧基或环烷基烷基，
R5代表氢原子，甲酰基，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-6个碳原子的烷基，烷基羰基，烷氧基羰基或烷基磺酰基，代表各自任选被卤原子取代的在各种情况下具有2-6个碳原子的链烯基或炔基，代表各自任选被氰基，卤原子或C1-C4烷基取代的在各种情况下环烷基基团具有3-6个碳原子的环烷基，环烷基羰基或环烷基磺酰基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基，呋喃基或四氢呋喃基，
除了在权利要求中已排除的现有技术化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲(参见EP 23422)。
本发明进一步优选提供其中A，Q，R1，R2，R3，R4和R5各自优选如上定义的式(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)-锍盐，C5或C6环烷基铵盐和二(C1-C2烷基)-苄基-铵盐。
本发明特别提供下列式(I)化合物，其中
A代表氮原子或CH基团，
Q代表氧原子或硫原子，
R1代表氢原子，氟，氯，溴或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，
R2代表氟，氯，溴或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，
R3代表氢原子，或者任选被甲氧基-，乙氧基-，正丙氧基-或异丙氧基-，乙酰基-，丙酰基-，正-或异-丁酰基-，甲氧基羰基-，乙氧基羰基-，正-或异-丙氧基羰基-取代的甲基或乙基，
R4代表各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，正-，异-，仲-或叔丁基，甲氧基，乙氧基，正丙氧基或异丙氧基，正-，异-，仲-或叔丁氧基，代表各自任选被氟-，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，丙炔基氧基或丁炔基氧基，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-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，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，
R5代表氢原子，甲酰基，代表各自任选被氰基-，氟-，氯-，甲氧基-，乙氧基-，正-或异-丙氧基取代的甲基，乙基，正丙基或异丙基，正-异-，仲-或叔丁基，乙酰基，丙酰基，正-或异-丁酰基，甲氧基羰基，乙氧基羰基，正-或异-丙氧基羰基，甲基磺酰基，乙基磺酰基，正-或异-丙基磺酰基，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，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-取代的环丙基，环丁基，环戊基，环己基，环丙基羰基，环丁基羰基，环戊基羰基，环己基羰基，环丙基磺酰基，环丁基磺酰基，环戊基磺酰基或环己基磺酰基，
除了在权利要求中排除的现有技术化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲(参见EP 23422)。
上述一般或优选的基团的定义适用于式(I)终产物和相应的用于制备的各种情况下需要的起始物或中间体。这些基团的定义可以根据需要相互组合，也就是说指出的优选的化合物范围之间的组合也是可能的。
本发明的式(I)化合物的实例在下面的组中列出。
第1组
A，Q，R1，R2和R3具有例如下面的意义：
A Q R1 R2 R3
CH O OCH3 OCH3 H
CH O CH3 OCH3 H
CH O CH3 CH3 H
CH O Cl OCH3 H
CH O H CH3 H
N O CH3 OCH3 CH3
N O OCH3 OCH3 CH3
N O CH3 OCH3 H
N O OCH3 OCH3 H
N O CH3 CH3 H
N O OCHF2 N(CH3)2 H
N O CH3 SCH3 H
N O C2H5 OCH3 H
N O CH3 OC2H5 H
N O H OCH3 H
A Q R1 R2 R3
N O OCH3
H
N O CH3 N(CH3)2 H
CH O OCH3
H
CH O
H
CH O CH3
H
CH O Cl
H
N O
H
N O CH3
H
A Q R1 R2 R3
N O H
H
N S CH3 OCH3 H
第2组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第3组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第4组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第5组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第6组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第7组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第8组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第9组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第10组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第11组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第12组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第13组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
第14组
A，Q，R1，R2和R3具有例如上面第1组给出的意义。
使用例如2-氨基-4-甲氧基-6-甲基嘧啶和异氰酸2-乙氧基-6-三氟甲基-苯基磺酰酯为起始物，本发明的方法(a)的反应过程可以通过下面的反应式来说明：
使用例如2-甲氧基羰基氨基-4-甲氧基-6-三氟甲基-1，3，5-三嗪和2-甲基-6-三氟甲氧基-苯磺酰胺为起始物，本发明的方法(b)的反应过程可以通过下面的反应式来说明：
使用例如2-氨基-4-氯-6-甲氧基嘧啶和N-(2，6-二甲氧基-苯基磺酰基)-O-苯基-尿烷为起始物，本发明的方法(c)的反应过程可以通过下面的反应式来说明：
式(II)提供了为了制备通式(I)的化合物而在方法(a)和(c)中用作起始物的氨基吖嗪的一般定义。在式(II)中，A，R1和R2各自优选地或特别地具有上文已经指出的，与说明式(I)化合物相关的，作为优选的或特别优选的A，R1和R2的定义。
式(II)的氨基吖嗪是已知的用于合成的化学品，其中的一些是可以商购的。
式(III)提供了在本发明方法(a)中也用作起始物的异(硫代)氰酸芳基磺酰酯的一般定义。在式(III)中，Q，R4和R5各自优选地或特别地具有上文已经指出的，与说明式(I)化合物相关的，作为优选的或特别优选的Q，R4和R5的定义。
式(III)起始物是已知的和/或可以通过本身已知的方法制备(参见DE 3208189，EP 23422，EP 64322，EP 44807，EP 216504，制备
实施例)。
如果适当的话在异氰酸烷基酯，例如，异氰酸丁酯存在下，如果适当的话在反应助剂例如二氮杂双环[2.2.2]-辛烷存在下，并且在稀释剂例如甲苯，二甲苯或氯苯存在下，上述通式(V)的芳烃磺酰胺与光气或硫光气在80℃和150℃之间的温度下反应，并且在反应终止后在减压下蒸馏出挥发性成分时，则获得式(III)的异(硫代)氰酸芳基磺酰酯。
式(IV)提供了为了制备通式(I)的化合物而在本发明方法(b)中用作起始物的取代的氨基中文吖嗪的一般定义。在式(IV)中，A，Q，R1和R2各自优选地或特别地具有上文已经指出的，与说明式(I)化合物相关的，作为优选的或特别优选的A，Q，R1和R2的定义；Z优选代表氟，氯，溴，C1-C4烷氧基或苯氧基，特别是氯，甲氧基，乙氧基或苯氧基。
式(IV)起始物是已知的和/或可以通过本身已知的方法制备(参见US 4690707，DE 19501174，制备实施例)。
式(V)提供了在本发明方法(b)中也用作起始物的芳烃磺酰胺的一般定义。在式(V)中，R4和R5各自优选地或特别地具有上文已经指出的，与说明式(I)化合物相关的，作为优选的或特别优选的R4和R5的定义。
式(V)起始物是已知的和/或可以通过本身已知的方法制备(参见DE 3208189，EP 23422，EP 64322，EP 44807，EP 216504，DE 19525162，制备实施例)。
式(VI)提供了为了制备通式(I)的化合物而在本发明方法(c)中用作起始物的取代的芳烃磺酰胺的一般定义。在式(VI)中，Q，R4和R5各自优选地或特别地具有上文已经指出的，与说明式(I)化合物相关的，作为优选的或特别优选的Q，R4和R5的定义；Z优选代表氟，氯，溴，C1-C4烷氧基或苯氧基，特别是氯，甲氧基，乙氧基或苯氧基。
式(VI)起始物是已知的和/或可以通过本身已知的方法制备(参见制备实施例)。
进行本发明方法(a)，(b)和(c)的合适的稀释剂是惰性有机溶剂。特别包括脂肪族，脂环族或芳香族的，任选卤化的烃，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，四氯化碳；醚类，例如乙醚，异丙醚，二恶烷，四氢呋喃或乙二醇二甲基或二乙基醚；酮类，例如丙酮，丁酮或甲基异丁基酮；腈类，例如乙腈，丙腈或苄腈；酰胺类，例如N，N-二甲基甲酰胺，N，N-二甲基乙酰胺，N-甲基-N-甲酰苯胺，N-甲基-吡咯烷酮或六甲基磷酰三胺；酯类，例如乙酸甲酯或乙酸乙酯；亚砜类，例如二甲亚砜；醇类，例如甲醇，乙醇，正-或异-丙醇，乙二醇单甲基醚，乙二醇单乙基醚，二乙二醇单甲基醚，二乙二醇单乙基醚以及它们与水的混合物或纯水。
本发明方法(a)，(b)和(c)优选在合适的反应助剂存在下进行，合适的反应助剂是所有的常规无机碱或有机碱。它们包括例如碱土金属或碱金属氢化物，氢氧化物，氨化物，烷氧化物，乙酸盐，碳酸盐或碳酸氢盐，例如氢化钠，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，以及叔胺类，例如三甲胺，三乙胺，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(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(a)，(b)和(c)时，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+150℃之间的温度下进行，优选在0℃和+120℃的温度下进行。
本发明方法(a)，(b)和(c)一般在大气压下进行。但是也可以在高压或低压下进行本发明方法，一般在0.1至10巴之间进行。
在实施本发明方法(a)，(b)和(c)时，一般以大约等摩尔量使用起始物。但是，也可以以相对大的过量使用其中之一起始物成分。反应一般在合适的反应助剂的存在下在稀释剂中进行，并且反应一般在需要的温度下搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
如果需要，由本发明通式(I)化合物制备盐。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中，例如二氯甲烷，丙酮，叔丁基甲基醚或甲苯，并加入一种合适的碱。然后，如果需要经延长时间的搅拌，通过浓缩或吸滤来分离盐。
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，所谓杂草被理解是在其所不期望的地点生长的所有植物。本发明物质是作为杀灭性除草剂还是选择性除草剂主要取决于使用的量。
对于例如下面的植物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)，毛茛属(Ranunculus)和蒲公英属(Taraxacum)。
双子叶作物种类：棉属(Gossypium)，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)，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)，Zea，Triticum，大麦属(Hordeum)，燕麦属(Avena)，黑麦属(Secale)，蜀黍属(Sorghum)，黍属(Panicum)，甘蔗(Saccharum)，菠萝(Ananas)，Asparagus和葱属(Allium)。
但是本发明活性化合物的用途绝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。这些化合物也被用来在多年生种植植物场所，草坪，运动场和牧场控制杂草，所述多年生种植植物场所例如树林，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植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控制单子叶和双子叶杂草。当对土壤和植物地上部分施用时，其具有强的除草活性和广谱活性。
活性化合物可以配制成常规制剂，例如溶液、乳液、可湿性粉末、悬浮液、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材料的天然和合成材料以及包裹在聚合物中的细微胶囊。
这些制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：芳族化合物，如二甲苯，甲苯或烷基萘，氯代芳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，如高分散二氧化硅、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，芳基磺酸盐以及白蛋白水解产物；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，可以是最终制剂或容器混合物。
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，恶唑禾草灵，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，异恶草酮，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照原样使用，可以以制剂形式使用，或者以通过进一步稀释而由其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大范围内变化。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-5kg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))
大约20℃下，将1.43g(5.6mmol)2-甲氧基-6-三氟甲基-苯磺酰胺，1.24g(5.1mmol)2-苯氧基羰基氨基-4，6-二甲基-嘧啶，0.85g(5.6mmol)二氮杂双环十一碳烯(DBU)和50ml乙腈的混合物搅拌15小时。然后用水泵抽真空来浓缩混合物，并且将残余物与50ml 1N盐酸和50ml二氯甲烷一起搅拌。分离有机相，用水洗涤，硫酸钠干燥并过滤。用水泵抽真空来浓缩滤液，残余物溶解于异丙醇，并且吸滤以分离结晶产物。
得到1.6g(理论值的62％)N-(4，6-二甲基-嘧啶-2-基)-N’-[2-甲氧基-6-三氟甲基-苯基磺酰基]-脲，熔点190℃。
实施例2
(方法(b))
大约20℃下，将2.0g(10mmol)2-甲氧基-6-甲基-苯磺酰胺，4.0g(10mmol)N，N-双-苯氧基羰基2-氨基-4，6-二甲氧基-1，3，5-三嗪，1.1g(10mmol)叔丁醇钾和50ml乙腈搅拌15小时。然后用水泵抽真空来浓缩混合物，并且将残余物与50ml 1N盐酸和50ml二氯甲烷一起搅拌。分离有机相，用水洗涤，硫酸钠干燥并过滤。用水泵抽真空来浓缩滤液，残余物溶解于异丙醇，并且吸滤以分离结晶产物。
得到2.1g(理论值的55％)N-(4，6-二甲氧基-1，3，5-三嗪-2-基)-N’-[2-甲氧基-6-甲基-苯基磺酰基]-脲，熔点163℃。
实施例3
(用前体的方法(c))
大约20℃下，将1.6g(10mmol)氯甲酸苯酯滴加到2.2g(10mmol)2-乙氧基-6-甲基-苯磺酰胺，2.0g(20mmol)三乙胺和30ml乙腈的混合物中，并在所述温度下将混合物搅拌大约30分钟。然后加入1.0g(10mmol)甲磺酸和1.6g(10mmol)2-氨基-4，6-二甲氧基-嘧啶，反应混合物在大约60℃搅拌大约15分钟。混合物冷却到大约20℃并吸滤，用水泵抽真空来浓缩滤液，并且将残余物与30ml 1N盐酸一起搅拌。吸滤并干燥，得到粗产物，其经乙醚漂洗而纯化。
产率：2.2g(理论值的55％)N-(4，6-二甲氧基-嘧啶-2-基)-N’-[2-乙氧基-6-甲基-苯基磺酰基]-脲，熔点184℃。
类似于制备实施例1-3，并且根据本发明关于制备方法的一般描述，也能制备例如下面表1中列出的式(I)化合物。
表1：式(I)化合物的实施例
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
4 N O CH3 OCH3 H CF3 C2H5 115
5 N O CH3 OCH3 H CF3 CH3 214
6 N O OCH3 OCH3 H CF3 CH3 189
7 N O OCH3 OCH3 H CF3 C2H5 176
8 CH O CH3 CH3 H CF3 C2H5 214
9 N O CH3 OCH3 H CF3 C3H7-n 142
10 N O OCH3 OCH3 H CF3 C3H7-n 162
11 CH O CH3 CH3 H CF3 C3H7-n 212
12 N O CH3 OCH3 H CF3 C3H7-i 168
13 N O OCH3 OCH3 H CF3 C3H7-i 200
14 CH O CH3 CH3 H CF3 C3H7-i 221
15 CH O Cl OCH3 H CF3 CH3 224
16 CH O Cl OCH3 H CF3 C2H5 176
17 CH O Cl OCH3 H CF3 C3H7-n 169
18 N O N(CH3)2 OCH2CF3 H CF3 CH3 222
19 N O N(CH3)2 OCH2CF3 H CF3 C2H5 209
20 N O N(CH3)2 OCH2CF3 H CF3 C3H7-n 175
21 N O N(CH3)2 OCH2CF3 H CF3 C3H7-i 204
22 CH O OCH3 OCH3 H CF3 CH3 111
(分解)
表1(续)
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
23 CH O OCH3 OCH3 H CF3 C2H5 99
(分解)
24 CH O OCH3 OCH3 H CF3 C3H7-n 180
25 CH O OCH3 OCH3 H CF3 C3H7-i 98
(分解)
26 CH O CH3 CH3 H CH3 C2H5 217
27 CH O CH3 OCH3 H CH3 C2H5 183
28 CH O H CH3 H CH3 C2H5 190
29 CH O CH3 CH3 H CH3 C3H7-n 194
30 CH O H CH3 H CH3 C3H7-n 176
31 N O OCH3 OCH3 H CH3 C2H5 181
32 N O CH3 OCH3 H CH3 C2H5 170
33 CH O CH3 OCH3 H CH3 C3H7-i 196
341) CH O OCH3 OCH3 H CH3
204
35 CH O CH3 CH3 H CH3 C3H7-i 231
36 CH O OCH3 OCH3 H CH3 C3H7-i 190
37 CH O H CH3 H CH3 C3H7-i 206
38 N O OCH3 OCH3 H CH3 C3H7-i 191
39 N O OCH3 OCH3 H CH3 C3H7-i 205
40 N O CH3 OCH3 H CH3 CH3 193
41 CH O CH3 CH3 H CH3 CH3 220
42 CH O H CH3 H CH3 CH3 206
43 CH O CH3 OCH3 H CH3 CH3 172
44 CH O OCH3 OCH3 H CH3 CH3 142
45 N O N(CH3)2 OCH2CF3H CH3 C2H5 187
表1(续)
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
46 CH O CH3 OCH3 H CH3 C3H7-n 147
47 CH O OCH3 OCH3 H CH3 C3H7-n 164
48 N O OCH3 OCH3 H CH3 C3H7-n 156
49 N O CH3 OCH3 H CH3 C3H7-n 150
50 CH O OCH3 OCH3 H C3H7-i C2H5 184
51 N O OCH3 OCH3 H C3H7-i C2H5 157
52 N O N(CH3)2 OCH2CF3 H CH3 CH3 214
53 N O N(CH3)2 OCH2CF3 H CH3 C3H7-i 202
54 CH O OCH3 OCH3 H CH3
171
55 N O OCH3 OCH3 H CH3
198
56 N O CH3 OCH3 H CH3
183
57 N O OCH3 OCH3 H CH3 C4H9-s 174
58 CH O CH3 OCH3 H CH3 C4H9-s 186
59 N O CH3 OCH3 H CH3 C4H9-s 177
60 CH O CH3 CH3 H CH3 C4H9-s 228
61 CH O OCH3 OCH3 H CH3 C4H9-s 207
62 CH O CH3 CF3 H CH3 C3H7-i 192
63 CH O CH3 CF3 H CH3 CH3 209
64 N O CH3 OCH3 H C3H7-i CH3 136
65 CH O OCH3 OCH3 H CH3 CHF2 170
66 N O CH3 OCH3 H CH3 CHF2 197
67 N O OCH3 OCH3 H OC3H7-n C3H7-n 140
表1(续)
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
68 CH O Cl OCH3 H OCH3 C3H7-i 148
69 N O CH3 OCH3 H OCH3 C3H7-i 152
70 N O CH3 OCH3 H OC4H9-n C4H9-n 90
71 N O CH3 OCH3 H OC3H7-i C3H7-i 80
72 N O CH3 OCH3 H OC2H5 C3H7-i 118
73 N O CH3 OCH3 Na OCH3 CH3 203
74 CH O OCH3 OCH3 H C3H7-i CH3 164
75 CH O OCH3 OCH3 H C3H7-i C3H7-n 157
76 CH O CH3 CF3 H CH3 C2H5 179
77 N O CH3 CH3 H CF3 CH3 155
78 N O CH3 SCH3 H CF3 CH3 178
79 N O CH3 N(CH3)2 H CF3 CH3 213
80 N O CH3 OC2H5 H CF3 CH3 121
81 N O C2H5 OCH3 H CF3 CH3 117
82 N O OCH2CF2CHF2 N(CH3)2 H CF3 CH3 185
83 N O CH3 OCH3 Na C3H7-i CH3 170
84 N O OCH3 OCH3 H C3H7-i C3H7-n 149
85 N O OCH3 OCH3 H C3H7-i CH3 187
86 N O CH3 OCH3 H C3H7-i C2H5 163
87 CH O CH3 OCH3 H C3H7-i CH3 175
88 CH O CH3 OCH3 H C3H7-i C3H7-i 152
89 CH O OCH3 OCH3 H C3H7-i C3H7-i 138
90 N O CH3 OCH3 Na CH3 CH3 149
91 N O CH3 CH3 H
125
表1(续)
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
92 N O CH3 OCH3 Na OC3H7-i C3H7-i 178
93 N O Cl OCH3 Na OCH3 C3H7-i 172
94 N O CH3 OCH3 Na OC2H5 C2H5 145
952) N O CH3 OCH3 Na OCH3 C3H7-n NMR数据
96 N O OCH3 OCH3 H OCH3 C2H5 110
97 N O OCH3 OCH3 H OC2H5 C2H5 142
98 N O OCH3 OCH3 H OCH3 C3H7-n 188
99 N O OCH3 OCH3 H OC2H5 C4H9-s 136
100 CH O Cl OCH3 H OCH3 C2H5 146
101 CH O Cl OCH3 H OCH3 C3H7-n 110
102 CH O Cl OCH3 H OCH3 C4H9-n 117
103 CH O Cl OCH3 H OC4H9-n C4H9-n 135
104 CH O Cl OCH3 H OC2H5 C4H9-n 128
105 N O CH3 OCH3 H OC2H5 C3H7-n 110
106 N O CH3 OCH3 H OCH3 CH3 177
107 N O CH3 OCH3 H OCH3
166
108 N O CH3 OCH3 H OC2H5 C4H9-i 85
109 N O CH3 OCH3 H OCH3 C2H5 148
110 N O CH3 OCH3 H OCH3 C4H9-n 125
111 N O CH3 OCH3 H OC2H5
130
112 CH O OCH3 OCH3 H CH3 CF3 178
113 N O CH3 OCH3 H CH3 CF3 178
114 CH O OCH3 OCH3 H C2H5 CF3 147
表1(续)
实施例 A Q R1 R2 R3 R4 R5 熔点
序号 (℃)
115 N O CH3 OCH3 H C2H5 CF3 140
116 CH O OCH3 OCH3 H CH3 CF2CHF2 169
117 N O CH3 OCH3 H CH3 CF2CHF2 184
118 CH O OCH3 OCH3 H CH3 CH2CF3 184
119 N O CH3 OCH3 H CH3 CH2CF3 178
120 CH O OCH3 OCH3 H C2H5 CHF2 110
121 N O CH3 OCH3 H C2H5 CHF2 157
122 CH O OCH3 OCH3 H C3H7-n CF3 147
123 N O CH3 OCH3 H C3H7-n CF3 77
注：
1)在实施例34中，
是炔丙基＝CH2-C≡CH
2)实施例95的NMR数据：
1H-NMR(300MHz；D2O)：δ＝0.96(t，CH3)；1.77(m，O-CH2-CH2-CH3)；2.42(s，CH3)；3.87(s，OCH3)；3.98(s，OCH3)；4.04(t，O-CH2-)；6.79(brd.d，2芳族.H)；7.48(brd.t，1芳族.H)ppm.
式(III)起始物：
实施例(III-1)
在100ml氯苯中将21.5g(0.1mol)2-乙氧基-6-甲基-苯磺酰胺和10g(0.1mol)异氰酸正丁酯加热到沸腾。回流温度下通入光气4小时。减压浓缩澄清的溶液，并将残余物精馏。在0.8毫巴压力和135-140℃塔顶温度下，精馏出异氰酸2-乙氧基-6-甲基-苯基磺酰酯，并且在接收瓶中固化。
得到7.9g异氰酸2-乙氧基-6-甲基-苯基磺酰酯，为无色产物，熔点40℃。
式(IV)起始物
实施例(IV-1)
搅拌下向31g(0.20mol)2-氨基-4，6-二甲氧基-s-三嗪和100ml吡啶的混合物中滴加70g(0.44mol)氯甲酸苯酯。反应混合物在20℃-25℃搅拌大约15小时后用水泵抽真空浓缩。残余物溶解于水后用浓盐酸酸化。通过吸滤来分离得到的结晶产物。
得到74.2g(理论值的91％)2-(N，N-双-苯氧基羰基-氨基)-4，6-二甲氧基-s-三嗪，熔点125℃。
式(V)起始物：
实施例(V-1)
在20℃，在350ml 25％浓度氨水中将64.6g(0.26mol)2-异丙氧基-6-甲基-苯磺酰氯搅拌12小时。接着通过吸滤来分离产生的结晶产物。
得到54g(理论值的90％)2-异丙氧基-6-甲基-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比例是重要的。
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。
数据表示：
0％＝没有效果(象未处理对照物一样)
100％＝完全杀伤
在该项试验中，例如制备实施例1，2，3，4，5，6，7，8，9，10，11，12，13，14，15，16，22，27，31，32，33，34，38，39，40，41，43，44，46，48，49，56，65和66的化合物在以每公顷用30g-125g活性成分(a.i.)之间的比例施用时，显示出非常强的除草活性。
表A：芽前试验/温室
活性化合物制备 施用比例
看麦娘 黑麦草 蜀黍 苋 藜 繁缕
实施例序号 (g of
ai./ha)
4 60 100 100 100 100 100 95
5 60 100 100 100 100 100 100
6 60 100 100 100 100 100 100
7 60 100 95 100 95 100 95
1 60 100 100 100 100 100 100
8 30 100 100 100 - 80 90
9 30 100 100 90 100 100 100
10 60 100 100 100 100 100 100
11 60 100 100 100 100 100 95
12 30 100 100 100 100 95 100
13 60 100 100 100 100 100 100
14 30 100 100 95 - 95 95
15 60 100 95 95 95 100 95
16 30 100 - 80 - 100 90
22 30 100 - 95 100 100 100
27 60 100 100 100 100 100 100
3 60 95 60 80 80 95 95
31 60 95 100 90 95 100 95
32 60 95 100 95 100 100 100
33 30 100 95 100 - 70 90
34 30 100 - 90 - 90 90
38 30 100 100 100 80 100 100
39 30 100 100 100 100 100 100
40 30 100 100 100 100 100 100
41 30 95 100 100 60 100 80
43 30 100 100 100 100 100 100
44 30 100 100 100 100 100 100
2 30 100 100 100 100 100 100
46 60 100 90 100 90 100 80
48 60 100 100 100 100 100 100
49 30 100 100 100 100 100 100
56 60 100 100 90 100 100 100
65 125 95 70 - 95 95 95
66 60 95 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，以便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。
数据表示：
0％＝没有效果(象未处理对照物一样)
100％＝完全杀伤
在该项试验中，例如制备实施例2，3，4，5，6，7，8，9，12，15，16，17，22，23，24，25，27，31，32，34，38，39，40，41，43，44，48，49，51，65和66的化合物显示出非常强的除草活性。
表B：芽后试验/温室
活性化合物制备 施用比例
看麦娘 稗 苘麻 母菊
实施例序号 (g of ai./ha)
4 30 90 90 100 100
5 30 80 100 100 100
6 30 60 100 90 100
7 30 95 95 95 100
8 30 80 90 90 100
9 8 90 80 100 95
12 30 95 90 95 100
15 60 70 90 95 100
16 30 70 70 100 100
17 30 - 70 90 95
22 30 60 80 95 95
23 30 60 70 95 95
24 30 60 70 95 95
25 30 60 70 95 90
27 60 95 95 100 90
3 60 90 80 100 95
31 60 80 80 100 100
32 60 70 90 100 100
34 30 60 80 90 90
38 30 60 70 95 95
39 30 90 95 100 100
40 30 100 95 95 100
41 30 60 95 90 70
43 30 60 95 100 100
44 30 60 90 100 100
2 30 90 90 95 100
48 60 95 70 100 90
49 30 90 80 100 100
51 60 80 90 100 90
65 125 90 90 100 100
66 60 80 80 100 100
Claims (9)
1.通式(I)取代的芳基磺酰基(硫代)脲：
其中
A代表CH，
Q代表氧原子或硫原子，
R1代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，
R2代表氢原子，卤原子或者各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基或杂环基氧基，
R3代表氢原子或者任选被取代的烷基，
R4代表各自任选被取代的烷基，烷氧基，链烯基，炔基，链烯基氧基，炔基氧基，环烷基，环烷基氧基或环烷基烷基，和
R5代表氢原子，甲酰基或者各自任选被取代的烷基，烷基羰基，烷氧基羰基，烷基磺酰基，链烯基，炔基，环烷基，环烷基羰基，环烷基磺酰基，或杂环基，
以及式(I)化合物的盐，
但排除化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲。
2.根据权利要求1的式(I)化合物，特征在于
A代表CH，
Q代表氧原子或硫原子，
R1代表氢原子，卤原子，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-4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，卤原子，C1-C4烷基或C1-C4烷氧基取代的在各种情况下有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基氧基，呋喃基氧基或四氢呋喃基氧基。
R2代表氢原子或卤原子，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-4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，卤原子，C1-C4烷基或C1-C4烷氧基取代的在各种情况下有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基氧基，呋喃基氧基或四氢呋喃基氧基，
R3代表氢原子或任选被C1-C4烷氧基，C1-C4烷基羰基或C1-C4烷氧基羰基取代的具有1-4个碳原子的烷基，
R4代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-6个碳原子的烷基或烷氧基，代表各自任选被卤原子取代的在各种情况下链烯基或炔基基团具有2-6个碳原子的链烯基，炔基，链烯基氧基或炔基氧基，或者代表各自任选被氰基，卤原子或C1-C4烷基取代的在各种情况下环烷基基团具有3-6个碳原子并且任选地烷基部分具有1-4个碳原子的环烷基，环烷基氧基或环烷基烷基，
R5代表氢原子，甲酰基，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-6个碳原子的烷基，烷基羰基，烷氧基羰基或烷基磺酰基，代表各自任选被卤原子取代的在各种情况下具有2-6个碳原子的链烯基或炔基，代表各自任选被氰基，卤原子或C1-C4烷基取代的在各种情况下环烷基基团具有3-6个碳原子的环烷基，环烷基羰基或环烷基磺酰基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基，呋喃基或四氢呋喃基，
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)-锍盐，C5或C6环烷基铵盐和二(C1-C2烷基)-苄基-铵盐，
但排除化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲。
3.权利要求1的式(I)化合物，特征在于
A代表CH，
Q代表氧原子或硫原子，
R1代表氢原子，氟，氯，溴或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，
R2代表氟，氯，溴或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，
R3代表氢原子，或者任选被甲氧基-，乙氧基-，正丙氧基-或异丙氧基-，乙酰基-，丙酰基-，正-或异-丁酰基-，甲氧基羰基-，乙氧基羰基-，正-或异-丙氧基羰基-取代的甲基或乙基，
R4代表各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，正-，异-，仲-或叔丁基，甲氧基，乙氧基，正丙氧基或异丙氧基，正-，异-，仲-或叔丁氧基，代表各自任选被氟-，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，丙炔基氧基或丁炔基氧基，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-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，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，
R5代表氢原子，甲酰基，代表各自任选被氰基-，氟-，氯-，甲氧基-，乙氧基-，正-或异-丙氧基取代的甲基，乙基，正丙基或异丙基，正-，异-，仲-或叔丁基，乙酰基，丙酰基，正-或异-丁酰基，甲氧基羰基，乙氧基羰基，正-或异-丙氧基羰基，甲基磺酰基，乙基磺酰基，正-或异-丙基磺酰基，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，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-取代的环丙基，环丁基，环戊基，环己基，环丙基羰基，环丁基羰基，环戊基羰基，环己基羰基，环丙基磺酰基，环丁基磺酰基，环戊基磺酰基或环己基磺酰基，
但排除化合物N-(4，6-二甲基-嘧啶-2-基)-N’-[2-(1，1，2，2-四氟-乙氧基)-6-甲基-苯基磺酰基]-脲。
4.权利要求1的式(I)化合物，特征在于
A代表CH，
Q代表氧原子或硫原子，
R1代表氢原子，氯，溴或者各自被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，或乙氧基取代的甲基，乙基，正丙基或异丙基，
R2代表氯，溴或者各自被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲氧基，乙氧基，正丙氧基或异丙氧基，甲硫基，乙硫基，正丙硫基或异丙硫基，甲基氨基，乙基氨基，正丙基氨基或异丙基氨基，二甲基氨基或二乙基氨基，或任选被氰基-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，
R3代表氢原子或任选被C1-C4烷氧基，C1-C4烷基羰基或C1-C4烷氧基羰基取代的C1-C4烷基，
R4代表被卤素取代的C1-C6烷基，
R5代表氢原子，甲酰基，代表各自任选被氰基，卤原子或C1-C4烷氧基取代的在各种情况下在烷基部分有1-6个碳原子的烷基，烷基羰基，烷氧基羰基或烷基磺酰基，代表各自任选被卤原子取代的在各种情况下具有2-6个碳原子的链烯基或炔基，代表各自任选被氰基，卤原子或C1-C4烷基取代的在各种情况下环烷基基团具有3-6个碳原子的环烷基，环烷基羰基或环烷基磺酰基，或者代表各自任选被氰基，卤原子，C1-C4烷基或C1-C4烷氧基取代的氧杂环丁烷基，呋喃基或四氢呋喃基；或上述定义的的化合物的盐。
5.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)的氨基吖嗪
其中
A，R1和R2各自如权利要求1定义，
与通式(III)的异(硫代)氰酸芳基磺酰酯反应
其中
Q，R4和R5各自如权利要求1定义，
或者
(b)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(IV)的取代的氨基吖嗪
其中
A，Q，R1和R2各自如上定义，
Z代表卤原子，烷氧基或芳基氧基，以及
R3如权利要求1定义或者代表基团-C(Q)-Z
与通式(V)的芳烃磺酰胺反应
其中
R4和R5各自如上定义，
或者
(c)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)的氨基吖嗪
其中
A，R1和R2各自如上定义，
与通式(VI)的取代的芳烃磺酰胺反应
其中
Q，R4和R5各自如上定义，
Z代表卤原子，烷氧基或芳基氧基，以及
如果合适，通过常规方法，将通过方法(a)，(b)和(c)获得的式(I)化合物转化成盐。
6.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。
7.权利要求1的通式(I)化合物控制不期望植物生长的用途。
8.控制杂草的方法，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。
9.制备除草组合物的方法，特征在于将权利要求1的通式(I)化合物与增充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19608445A DE19608445A1 (de) | 1996-03-05 | 1996-03-05 | Substituierte Arylsulfonyl(thio)harnstoffe |
| DE19608445.8 | 1996-03-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB971928207A Division CN1165527C (zh) | 1996-03-05 | 1997-02-20 | 用作除草剂的取代的芳基磺酰基(硫代)脲类 |
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| Publication Number | Publication Date |
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| CN1576274A true CN1576274A (zh) | 2005-02-09 |
| CN1293060C CN1293060C (zh) | 2007-01-03 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| CNB971928207A Expired - Fee Related CN1165527C (zh) | 1996-03-05 | 1997-02-20 | 用作除草剂的取代的芳基磺酰基(硫代)脲类 |
| CNB2004100699417A Expired - Fee Related CN1293060C (zh) | 1996-03-05 | 1997-02-20 | 用作除草剂的取代的芳基磺酰基(硫代)脲类 |
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| CNB971928207A Expired - Fee Related CN1165527C (zh) | 1996-03-05 | 1997-02-20 | 用作除草剂的取代的芳基磺酰基(硫代)脲类 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6451737B1 (zh) |
| EP (2) | EP0885200B1 (zh) |
| CN (2) | CN1165527C (zh) |
| AU (1) | AU712363B2 (zh) |
| BR (1) | BR9707917A (zh) |
| DE (2) | DE19608445A1 (zh) |
| DK (1) | DK0885200T3 (zh) |
| ES (1) | ES2303724T3 (zh) |
| HK (1) | HK1074201A1 (zh) |
| WO (1) | WO1997032861A1 (zh) |
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| DE19525162A1 (de) * | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
| DE19608445A1 (de) * | 1996-03-05 | 1997-09-11 | Bayer Ag | Substituierte Arylsulfonyl(thio)harnstoffe |
| DE19963383A1 (de) * | 1999-12-28 | 2001-07-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| DE10111649A1 (de) * | 2001-03-12 | 2002-09-19 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylharnstoffe |
| SE525958C2 (sv) * | 2003-10-10 | 2005-05-31 | Kongsberg Automotive Ab | Säteskonstruktion |
| EP1717232A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Phenylsulfonylharnstoffe mit herbizider Wirkung |
| EP1717228A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Sulfonylamino(thio)carbonylverbindungen als Herbizide oder Pflanzenwachstumsregulatoren |
| KR101031282B1 (ko) | 2009-09-16 | 2011-04-29 | 전남대학교산학협력단 | 하프-브릿지 방식의 dc/dc컨버터 |
| US9962251B2 (en) | 2013-10-17 | 2018-05-08 | Boston Scientific Scimed, Inc. | Devices and methods for delivering implants |
| CN106317348A (zh) * | 2016-08-23 | 2017-01-11 | 无锡市永亿精密铸造有限公司 | 一种用于超声波雾化器的复合材料 |
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| US4169719A (en) | 1976-04-07 | 1979-10-02 | E. I. Du Pont De Nemours And Co. | Herbicidal sulfonamides |
| US4452628A (en) * | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0064322B1 (en) | 1979-07-26 | 1985-05-22 | E.I. Du Pont De Nemours And Company | Benzenesulfonyl isocyanates, isothiocyanates, chlorides, and sulfonamides having a fluorinated substituent |
| AU544382B2 (en) | 1980-07-11 | 1985-05-23 | E.I. Du Pont De Nemours And Company | N-3(n-heterocyclic)-n:-phenyl sulphonyl(thio) ureas |
| US4425153A (en) | 1980-07-11 | 1984-01-10 | E. I. Du Pont De Nemours & Co. | Herbicidal sulfonamides |
| CA1330438C (en) * | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
| US4443243A (en) | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| MA19680A1 (fr) | 1982-01-11 | 1983-10-01 | Novartis Ag | N- arylsulfonyl - n' - pyrimidinylurees. |
| DE3208189A1 (de) | 1982-03-06 | 1983-09-08 | Hoechst Ag, 6230 Frankfurt | 2-aminomethyl-6-sulfamoylphenolderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| BR8302396A (pt) | 1982-05-12 | 1984-01-10 | Du Pont | Composto;composicao e processo adequados para controlar o crescimento de vegetacao indesejada |
| US4537618A (en) * | 1982-05-26 | 1985-08-27 | Ciba Geigy Corporation | N-phenylsulfonyl-N'-pyrimidinylureas |
| US4780126A (en) * | 1984-08-30 | 1988-10-25 | Bayer Aktiengesellschaft | 3-substituted 1-(2-halogenoalkoxy-benzenesulphonyl)-3-heteroaryl-(thio)ureas |
| DE3431917A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | 1-(2-trifluormethoxy-phenylsulfonyl)-3- heteroaryl-(thio)-harnstoffe |
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| DE19608445A1 (de) * | 1996-03-05 | 1997-09-11 | Bayer Ag | Substituierte Arylsulfonyl(thio)harnstoffe |
| DE10111649A1 (de) * | 2001-03-12 | 2002-09-19 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylharnstoffe |
-
1996
- 1996-03-05 DE DE19608445A patent/DE19608445A1/de not_active Withdrawn
-
1997
- 1997-02-20 EP EP97906098A patent/EP0885200B1/de not_active Expired - Lifetime
- 1997-02-20 BR BR9707917A patent/BR9707917A/pt not_active IP Right Cessation
- 1997-02-20 EP EP06009626A patent/EP1683789A1/de not_active Withdrawn
- 1997-02-20 CN CNB971928207A patent/CN1165527C/zh not_active Expired - Fee Related
- 1997-02-20 DE DE59712940T patent/DE59712940D1/de not_active Expired - Lifetime
- 1997-02-20 ES ES97906098T patent/ES2303724T3/es not_active Expired - Lifetime
- 1997-02-20 CN CNB2004100699417A patent/CN1293060C/zh not_active Expired - Fee Related
- 1997-02-20 DK DK97906098T patent/DK0885200T3/da active
- 1997-02-20 US US09/125,997 patent/US6451737B1/en not_active Expired - Fee Related
- 1997-02-20 AU AU20917/97A patent/AU712363B2/en not_active Ceased
- 1997-02-20 WO PCT/EP1997/000798 patent/WO1997032861A1/de active IP Right Grant
-
2002
- 2002-07-16 US US10/195,979 patent/US6838414B2/en not_active Expired - Fee Related
-
2004
- 2004-07-29 US US10/901,780 patent/US7723266B2/en not_active Expired - Fee Related
-
2005
- 2005-08-04 HK HK05106724A patent/HK1074201A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9707917A (pt) | 1999-07-27 |
| US7723266B2 (en) | 2010-05-25 |
| AU2091797A (en) | 1997-09-22 |
| DE59712940D1 (de) | 2008-07-03 |
| US20050004123A1 (en) | 2005-01-06 |
| AU712363B2 (en) | 1999-11-04 |
| CN1212686A (zh) | 1999-03-31 |
| EP0885200B1 (de) | 2008-05-21 |
| HK1074201A1 (en) | 2005-11-04 |
| WO1997032861A1 (de) | 1997-09-12 |
| EP0885200A1 (de) | 1998-12-23 |
| ES2303724T3 (es) | 2008-08-16 |
| DE19608445A1 (de) | 1997-09-11 |
| EP1683789A1 (de) | 2006-07-26 |
| CN1293060C (zh) | 2007-01-03 |
| DK0885200T3 (da) | 2008-09-22 |
| US6451737B1 (en) | 2002-09-17 |
| US20030153463A1 (en) | 2003-08-14 |
| CN1165527C (zh) | 2004-09-08 |
| US6838414B2 (en) | 2005-01-04 |
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