CN1162426C - 噻吩基烷基氨基-1,3,5-三嗪类及其作为除草剂的应用 - Google Patents
噻吩基烷基氨基-1,3,5-三嗪类及其作为除草剂的应用 Download PDFInfo
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- CN1162426C CN1162426C CNB998048119A CN99804811A CN1162426C CN 1162426 C CN1162426 C CN 1162426C CN B998048119 A CNB998048119 A CN B998048119A CN 99804811 A CN99804811 A CN 99804811A CN 1162426 C CN1162426 C CN 1162426C
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
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- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
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- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及新的通式(I)的噻吩烷基氨基-1,3,5-三嗪,其中,A、R1、R2、R3、R4、R5和Z具有说明书中陈述的含义。本发明还涉及所述化合物的制备及其作为除草剂的应用。本发明还涉及新的中间体产物及其应用。
Description
本发明涉及新颖的噻吩基烷基氨基-1,3,5-三嗪类,其制备及其作为除草剂的应用。
美国专利3,753,986和WO 97/08156 A1公开了一些据认为可用作除草剂的三嗪类衍生物。
许多噻吩基烷基氨基三嗪类在(专利)文献中已有报道(参见,JP63222166-引述于化学文摘《Chem.Abstracts》111:97288w)。然而,这些化合物迄今尚未获得任何特别的重要性。
因此,本发明提供新的通式(I)的噻吩基烷基氨基-1,3,5-三嗪类,
其中
A表示亚甲基(-CH2-)或二亚甲基(-CH2CH2-),
R1表示氢或表示任选由氰基-、卤素-或C1-C4-烷氧基取代的具有1至4个碳原子的烷基,
R2表示氢,表示甲酰基或表示均可任选由氰基-、卤素-或C1-C4-烷氧基-取代的各在烷基中具有1至4个碳原子的烷基、烷基羰基、烷氧基羰基或烷基氨基羰基,
R3表示氢或表示任选由氰基-、卤素-或C1-C4-烷氧基-取代的具有1至4个碳原子的烷基,或表示任选由氰基-、卤素-或C1-C4-烷基-取代的具有3至6个碳原子的环烷基,
R4表示硝基、氰基、氨基甲酰基、硫代氨基甲酰基、卤素,表示均可任选由卤素-取代的各具有至多4个碳原子的烷基、烷氧基、烷基羰基或烷氧基羰基,或-在A表示二亚甲基的情况下-还表示氢,
R5表示氢、卤素,或表示均可任选由卤素-取代的各具有1至4个碳原子的烷基或烷氧基,和
Z表示氢,表示卤素,表示均可任选由氰基-、卤素-、羟基-、C1-C4-烷氧基-或C1-C4-烷硫基-取代的各具有1至6个碳原子的烷基或烷氧基,表示均可任选由氰基-、卤素-或C1-C4-烷氧基取代的各在烷基中具有1至6个碳原子的烷基羰基、烷氧基羰基、烷硫基、烷基亚磺酰基或烷基磺酰基,表示均可任选由卤素-取代的具有2至6个碳原子的链烯基或炔基,或表示任选由氰基-、卤素-或C1-C4-烷基取代的具有3至6个碳原子的环烷基。
新的通式(I)的噻吩基烷基氨基三嗪类如下获得:
(a)如果适宜在反应辅助剂存在下,和如果适宜在稀释剂存在下,使通式(II)的双胍
其中
A、R1、R2、R3、R4和R5如上定义,
-和/或通式(II)化合物的酸加合物
与通式(III)的烷氧基羰基化合物反应
Z-CO-OR’ (III)
其中
Z如上定义,和
R’表示烷基,
或
(b)如果适宜在反应辅助剂存在下,和如果适宜在稀释剂存在下,使通式(IV)的取代的卤代三嗪
其中
A、R3、R4、R5和Z如上定义,
X表示卤素,
与通式(V)的含氮化合物反应
其中
R1和R2如上定义,
或
(c)如果适宜在反应辅助剂存在下,和如果适宜在稀释剂存在下,使通式(VI)的取代的氨基三嗪
其中
R1、R2和Z如上定义,和
Y1表示卤素或烷氧基,
与通式(VII)的取代的烷基胺反应
其中
A、R3、R4和R5如上定义,
或
(d)如果适宜在反应辅助剂存在下,和如果适宜在稀释剂存在下,使通式(Ia)的取代的2,4-二氨基-1,3,5-三嗪
其中
A、R1、R3、R4、R5和Z如上定义,
与通式(VIII)的烷基化剂或酰化剂反应
Y2-R2 (VIII)
R2如上定义,氢除外,和
Y2表示卤素、-OR2或-O-CO-R2,
和如果适宜,在取代基上述定义范围内可以通过常规方法进一步转化根据方法(a)、(b)、(c)或(d)获得的通式(I)化合物。
新的通式(I)的取代的2,4-二氨基-1,3,5-三嗪类具有强且有选择性的除草活性。
如果适宜,本发明的通式(I)化合物含有不对称取代的碳原子且因此可以存在不同的对映体(R-和S-构型)和/或非对映体。本发明涉及各种可能的通式(I)化合物的单个对映体或立体异构体,也涉及这些异构化合物的混合物。
在其定义中,烃链如烷基-包括与杂原子的组合如烷氧基或烷硫基-在每一情况下是直链或支链。
卤素通常表示氟、氯、溴或碘,优选表示氟、氯或溴,特别是表示氟或氯。
本发明优选提供式(I)化合物,其中
A表示亚甲基(-CH2-)或二亚甲基(-CH2CH2-),
R1表示氢或表示任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异丙基,
R2表示氢,表示甲酰基或表示均可任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基、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、甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基,
R3表示氢或表示均可任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基,或表示均可任选由氰基-、氟-、氯-、甲基-或乙基-取代的环丙基、环丁基、环戊基或环己基,
R4表示硝基、氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,或表示均可任选由氟和/或氯-取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基和-在A表示二亚甲基的情况下-还表示氢,
R5表示氢、氟、氯、溴,或表示均可任选由氟-和/或氯-取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基,和
Z表示氢,表示氟、氯、溴,表示均可任选由氰基-、氟-、氯-、溴-、羟基-、甲氧基-、乙氧基-、甲硫基-或乙硫基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、正-、异-、仲-或叔丁氧基,表示均可任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的乙酰基、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、甲硫基、乙硫基、正或异丙硫基、正-、异-、仲-或叔丁硫基、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,表示可任选由氟-、氯-和/或溴-取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基或丁炔基,或表示任选由氰基-、氟-、氯-、溴-、甲基-或乙基-取代的环丙基、环丁基、环戊基或环己基。
本发明特别是涉及式(I)化合物,其中
A表示亚甲基(-CH2-)或二亚甲基(-CH2CH2-),
R1表示氢,
R2表示氢、甲酰基、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,
R3表示甲基、乙基、正或异丙基,
R4表示硝基、氰基、氟、氯、溴,或表示均可任选由氟和/或氯-取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基和-在A表示二亚甲基的情况下-还表示氢,
R5表示氢、氟、氯、溴,或表示均可任选由氟-和/或氯-取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基,和
Z表示均可任选由氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基,或表示环丙基。
非常特别优选的一组式(I)化合物是这样的化合物,其中A表示亚甲基且R1、R2、R3、R4、R5和Z具有上文给出的特别优选的含义。特别强调的是,在每一种情况下均可能存在R对映体和S对映体。另外还特别的是,其中Z表示1-氟乙基和1-氟-1-甲基-乙基的化合物。
另外的非常特别优选的一组式(I)化合物是这样的化合物,其中A表示二亚甲基且R1、R2、R3、R4、R5和Z具有上文给出的特别优选的含义。
上面提到的一般或优选的基团定义适合于式(I)终产物,且相应地,也适合于在每一种制备情况下所需的起始原料或中间体。这些基团定义可以按照需要相互结合,即,包括上面提到的优选范围间的组合。
本发明通式(I)化合物的特别优选的实例分组列于下文。
组1
Z具有例如下列含义:
甲基、乙基、正或异丙基、氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、氯氟甲基、氯溴甲基、氯二氟甲基、氟二氯甲基、溴二氟甲基、三氯甲基、1-氟-乙基、2-氟-乙基、1-氯-乙基、2-氯-乙基、1-溴-乙基、1-氯-1-氟-乙基、1-氟-丙基、2-氟-丙基、3-氟-丙基、1-氯-丙基、2-氯-丙基、3-氯-丙基、1-溴-丙基、1-氟-1-甲基-乙基、2-氟-1-甲基-乙基、1-氯-1-甲基-乙基、2-氯-1-甲基-乙基、1,1-二氟-乙基、1,2-二氟-乙基、1,1-二氯-乙基、2,2,2-三氟-乙基、1,2,2,2-四氟乙基、全氟乙基、1,1-二氟-丙基、1,1-二氯-丙基、全氟丙基、1-羟基-乙基、1-羟基-1-甲基-乙基、1-羟基-丙基、甲氧基甲基、乙氧基甲基、二甲氧基-甲基、1-甲氧基乙基、2-甲氧基-乙基、1,1-二甲氧基-乙基、1-乙氧基-乙基、2-乙氧基-乙基、2,2-二甲氧基-乙基、2,2-二乙氧基-乙基、2-甲氧基-1-甲基乙基、2-乙氧基-1-甲基-乙基、2,2-双-甲氧基-甲基、甲硫基甲基、乙硫基甲基、1-甲硫基-乙基、2-甲硫基乙基、1-乙硫基-乙基、2-乙硫基乙基、甲基亚磺酰基甲基、乙基亚磺酰基甲基、甲基磺酰基甲基、乙基磺酰基甲基。
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使用例如1-[1-乙基-4-(噻吩-2-基)-丁基]-双胍和三氟乙酸甲酯作为起始原料,本发明方法(a)之反应途径可以由下列反应式例示说明:
使用例如2-氯-4-[1-乙基-4-(2-氰基-噻吩-3-基)-丙氨基]-6-三氟甲基-1,3,5-三嗪和乙胺作为起始原料,本发明方法(b)之反应途径可以由下列反应式例示说明:
使用例如2-氨基-4-甲氧基-6-三氟甲基-1,3,5-三嗪和1-(3-三氟甲基-噻吩-2-基)-丁-3-胺作为起始原料,本发明方法(c)之反应途径可以由下列反应式例示说明:
使用例如2-氨基-4-[1-乙基-4-(噻吩-3-基)-丁氨基]-6-三氟甲基-1,3,5-三嗪和乙酰氯作为起始原料,本发明方法(d)之反应途径可以由下列反应式例示说明:
式(II)提供在制备式(I)化合物的本发明方法(a)中用作起始原料的双胍的一般定义。在式(II)中,A、R1、R2、R3、R4和R5各优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的A、R1、R2、R3、R4和R5的优选或特别优选的含义。
适合的式(II)化合物的酸加合物是其与质子酸,如与氯化氢(盐酸)、溴化氢(氢溴酸)、硫酸、甲磺酸、苯磺酸和对甲苯磺酸的加成产物。
通式(II)起始原料迄今未在文献中公开;作为新物质,它们同样构成本专利申请的主题。
新的通式(II)双胍如下获得:
如果适合,在反应辅助剂如氯化氢存在下,和如果适宜在稀释剂例如正癸烷或1,2-二氯-苯存在下,在100℃至200℃间的温度下,使通式(VII)噻吩基烷基胺
其中
A、R3、R4和R5如上定义,
-和/或通式(VII)化合物的酸加合物,例如,其盐酸盐-
与通式(IX)氰基胍“双氰二胺“反应。
在其制备后,通式(II)的双胍还可以无需中间分离直接制备本发明的通式(I)化合物(参见,制备实施例)。
需作为中间体的其中A表示亚甲基的通式(VII)的噻吩基烷基胺是已知的和/或可以通过本身已知的方法制备(参见,EP 94595,EP101069)。
其中A表示二亚甲基的通式(VII)的噻吩烷基胺迄今未在文献中公开;作为新物质,它们同样构成本专利申请的主题。
新的通式(VIIa)的噻吩基烷基胺
其中
R3、R4和R5如上定义
-和/或其酸加合物-如下获得:
将通式(X)的N-噻吩基烷基-甲酰胺
其中
R3、R4和R5如上定义
用酸,例如盐酸,在水中于80℃至100℃间的温度下加热(参见,制备实施例)。
通式(X)的N-噻吩基烷基-甲酰胺迄今未在文献中公开;作为新物质,它们同样构成本专利申请的主题。
新的通式(X)的N-噻吩基烷基-甲酰胺如下获得:
使通式(XI)的噻吩基烷基酮
其中
R3、R4和R5如上定义
与甲酰胺和甲酸在140℃至180℃间的温度下反应(参见制备实施例)。
通式(XI)的噻吩基烷基酮是已知的和/或可以通过本身已知的方法制备(参见,《法国化学学会公报》[Bull.Soc.Chim.France]1954,1349-1356;《四面体》[Tetrahedron]35(1979),329-340)。
通式(III)提供在制备式(I)化合物的本发明方法(a)中另一用作起始原料的烷氧基羰基化合物的一般定义。在式(III)中,Z优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的Z的优选或特别优选的含义;R′优选表示具有1至4个碳原子的烷基,特别是甲基或乙基。
式(III)起始原料是合成上已知的有机化学品。
式(IV)提供在制备式(I)化合物的本发明方法(b)中用作起始原料的取代的卤代三嗪的一般定义。在式(IV)中,A、R3、R4、R5和Z各优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的A、R3、R4、R5和Z的优选或特别优选的含义;X优选表示氟或氯,特别是氯。
通式(IV)起始原料迄今未在文献中公开;作为新物质,它们同样构成本专利申请的主题。
通式(IV)的取代的卤代三嗪如下获得:
如果适宜在酸接受体如乙基二异丙胺存在下,和如果适宜在稀释剂如四氢呋喃或二噁烷存在下,在-50℃至+50℃间的温度下,
使相应的通式(XII)的二卤代三嗪
其中
X和Z如上定义,和
X1表示卤素(优选氟或氯)
与通式(VII)的噻吩基烷基胺反应
其中
A、R3、R4和R5如上定义。
式(VI)提供在制备式(I)化合物的本发明方法(c)中用作起始原料的取代的氨基三嗪的一般定义。在式(VI)中,R1、R2和Z各优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的R1、R2和Z的优选或特别优选的含义;Y1优选表示氟、氯、甲氧基或乙氧基,特别是氯或甲氧基。
通式(VI)起始原料是已知的和/或可以通过本身已知的方法制备(参见,WO95/11237)。
式(VII)提供在制备式(I)化合物的本发明方法(c)中另一用作起始原料的噻吩基烷基胺的一般定义。在式(VII)中,A、R3、R4和R5各优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的A、R3、R4和R5的优选或特别优选的含义。
通式(VII)起始原料的制备描述于上文的对本发明方法(a)起始原料的描述中。
式(Ia)提供在制备式(I)化合物的本发明方法(d)中用作起始原料的取代的2,4-二氨基-1,3,5-三嗪的一般定义。在式(VII)中,A、R1、R3、R4、R5和Z各优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的A、R1、R3、R4、R5和Z的优选或特别优选的含义。
作为新物质,通式(Ia)起始原料同样构成本发明申请的主题;它们可以根据本发明方法(a)、(b)或(c)制备(参见制备实施例)。
式(VIII)提供在制备式(I)化合物的本发明方法(d)中另一用作起始原料的烷基化剂或酰化剂的一般定义。在式(VIII)中,R2除氢之外优选或特别是具有在上文有关本发明式(I)化合物的描述中业已提到的R2的优选或特别优选的含义;Y2优选表示氟、氯、溴、甲氧基、乙氧基、乙酰氧基或丙酰氧基,特别是氯、甲氧基或乙酰氧基。
通式(VII)起始原料是合成上已知的化学品。
如果适宜,制备通式(I)化合物的本发明方法是使用反应辅助剂进行的。适合的方法(a)、(b)、(c)和(d)的反应辅助剂通常是常规的无机或有机碱或酸受体。这些物质优选包括碱金属或碱土金属的乙酸盐、氨化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇盐,如乙酸钠、乙酸钾或乙酸钙、氨化锂、氨化钠、氨化钾或氨化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙、氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙,甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇的钠盐或甲醇、乙醇、正-或异丙醇、正-、异-、仲-或叔丁醇的钾盐;另外还有碱性有机氮化合物,如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苄基胺、吡啶、2-甲基-、3-甲基-、4-乙基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、4-二甲基氨基-吡啶、N-甲基-哌啶、1,4-二氮杂二环[2,2,2]-辛烷(DABCO)、1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)或1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)。
除水之外,适合于进行本发明方法(a)、(b)、(c)和(d)的稀释剂特别是惰性有机溶剂。这些物质包括特别是脂肪族、脂环族或芳族的任选卤代的烃,诸如,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,如***、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二***;酮类,如甲基异丙基酮或甲基异丁基酮;腈类,如乙腈、丙腈或丁腈;酰胺类,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酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;醇类,如甲醇、乙醇、正-或异丙醇、乙二醇单甲醚、乙二醇单***、二甘醇单甲醚、二甘醇单***,它们与水的混合物,或纯水。
进行本发明方法(a)、(b)、(c)和(d)时,反应温度可以在相对宽的范围内进行的。通常,反应是在-20℃至+300℃,优选在-10℃至+250℃间的温度下进行。
本发明的方法(a)、(b)、(c)和(d)通常是在常压下进行的。然而,本发明方法也可以在加压或减压下——通常是在0.1巴至10巴间的压力下进行。
进行本发明方法时,通常采用大致等摩尔量的起始原料。然而,也可以相对大地过量采用反应组分之一。反应通常是在适合的稀释剂中,在反应辅助剂存在下进行的,且反应混合物通常在所需的温度下搅拌几小时。后处理是用常规方法进行(参见,制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,和特别是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛茛属、蒲公英属。
下列属的双子叶作物:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属、南瓜属。
下列属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属、风草属。
下列属的单子叶作物:稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属、葱属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(I)化合物特别适合于以芽前和芽后二种方式选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
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,即液体和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,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,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石、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:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是: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;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘结剂如羧甲基纤维素和天然和合成的粉状、颗粒或乳胶形式的聚合物,如***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。
也可以使用着色剂,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,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
为防治杂草,本发明活性化合物,其原样或以其制剂形式,也可以作为与已知除草剂一起的混合物使用,可以是终制剂或桶混物。
混合物的可能的共组分是已知除草剂,例如,乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草特、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、灭草平、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草松、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、双苯唑快、双氟酰草胺、diflufenzopyr、丁唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、epoprodan、茵达灭、禾草畏、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、唑嘧磺黄胺伏草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酯、氟丁酮、氟草烟、调嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamid、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、吡氟氯禾灵(-P-甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻草胺、苯嗪草酮、吡草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、pelargonicacid、二甲戊乐灵、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、炔苯酰草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭草醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcotrione、甲磺草胺、嘧黄隆(甲酯)、草硫磷、sulfosulfuron、牧草胺、丁噻隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵和氟胺黄隆。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用,如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物萌发前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常,使用量在每公顷土表面积用1克至10千克之间,优选每公顷5克至5千克。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例:
实施例1
(方法(a),包括式(II)起始原料制备)
将2.1g(10mmol)2-氨基-5-(噻吩-2-基)-戊烷盐酸盐和0.84g(10mmol)氰基胍的混合物在160℃下加热30分钟。除去热浴,将反应混合物在大约100℃与40ml甲醇混合。之后加入2.8g分子筛,并将混合物冷却至-10℃,依次与1.1g(20mmol)甲醇钠和1.32g(11mmol)2-氟-异丁酸甲酸混合。反应混合物在20℃下搅拌15小时。之后将混合物过滤,滤液在水泵真空下浓缩,残余物进行柱色谱(硅胶,乙酸乙酯/己烷,体积比1∶1)。
由此给出0.7g(理论值的22%)2-氨基-4-(1-氟-1-甲基-乙基)-6-(1-甲基-4-(噻吩-2-基)-丁基氨基)-1,3,5-三嗪,为淡黄色油状物。
类似于制备实施例1,并根据本发明制备方法的一般描述,可以制备出例如列于下文表1中的式(I)化合物。
表1:式(I)化合物的实例
式(VII)起始原料:
实施例(VII-1)
将9.8g(50mmol)N-(1-甲基-4-(噻吩-2-基)-丁基)-甲酰胺、100ml浓盐酸和40ml水加热回流90分钟。之后将混合物在水泵真空下大体上浓缩,残余物用***搅拌。滗析掉醚相,在水泵真空下仔细地将溶剂从残余物中蒸馏掉。
由此给出8.5g(理论值的83%)2-氨基-5-(噻吩-2-基)-戊烷盐酸盐,为暗色油状物。
式(X)起始原料
实施例(X-1)
将10.2g(60mmol)5-(噻吩-2-基)-戊-2-酮和60ml甲酰胺的混合物加热到150℃至160℃,随后加入13.5g甲酸,在160℃下搅拌2小时。在冷却到室温(大约20℃)后,将反应混合物与甲苯/水搅拌,分离出有机相,用硫酸钠干燥并过滤。从滤液中,在水泵真空下仔细地将溶剂蒸馏掉(最终为80℃下2毫巴)。
由此给出9.8g(理论值的83%)N-(1-甲基-4-(噻吩-2-基)-丁基)-甲酰胺,为油状残余物。
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份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,24小时后,土壤按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照的发育相比较,目测定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全损害
在此试验中,例如,制备实施例1、4、5、6、7、19、20、22、25和26对杂草显示出强活性,且能被作物如棉花、玉米、小麦和大麦很好地耐受。
实施例B
芽后试验
溶剂: 5份重量丙酮
乳化剂:1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如,制备实施例1、2、4、5、6和7对杂草显示出强活性,且能被作物如玉米、大麦和小麦很好地耐受。
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 玉米 看麦娘 苋 芥
(g ai./ha)
本发明:
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 小麦 玉米 马唐 藜 茄 婆婆娘 堇菜
(g ai./ha)
本发明:
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 大麦 玉米 狗尾草 藜 婆婆纳 堇菜
(g ai./ha)
本发明:
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 小麦 看麦娘 马唐 狗尾草 藜 茄 婆婆纳 堇菜
(g ai./ha)
本发明:
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 莎草 苋 母菊 婆婆纳
(g ai./ha)
本发明:
500 100 100 100 100
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 棉花 马唐 苋 曼陀罗 茄 婆婆纳
(g ai./ha)
本发明:
500 0 100 100 100 100 100
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 小麦 棉花 苋 母菊 茄 婆婆纳
(g ai./ha)
本发明:
500 0 0 100 100 100 100
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 小麦 玉米 大豆 马唐 苋 茄 婆婆纳 堇菜
(g ai./ha)
本发明:
500 0 0 0 100 100 100 100 100
表A:温室芽前试验
如下实施例号的活性化合物
施用剂量 小麦 玉米 黑麦草 母菊 婆婆纳 堇菜
(g ai./ha)
本发明:
500 0 0 90 95 100 100
表B:温室芽后试验
如下实施例号的活性化合物
施用剂量 玉米 狗尾草 苘麻 苋 芥
(g ai./ha)
本发明:
表B:温室芽后试验
如下实施例号的活性化合物
施用剂量 大麦 小麦 曼陀罗 甘薯 茄 堇菜
(g ai./ha)
本发明:
125 0 0 95 95 100 95
如下实施例号的活性化合物
施用剂量 大麦 小麦 曼陀罗 甘薯 茄 堇菜
(g ai./ha)
表B:温室芽后试验
如下实施例号的活性化合物
施用剂量 大麦 小麦 狗尾草 曼陀罗 甘薯 茄 堇菜
(g ai./ha)
本发明:
500 0 0 80 95 95 95 100
表B:温室芽后试验
如下实施例号的活性化合物
施用剂量 大麦 小麦 马唐 曼陀罗 甘薯 茄 堇菜
(g ai./ha)
本发明:
500 0 0 90 100 100 100 100
Claims (8)
2.根据权利要求1的通式(I)的噻吩基烷基氨基-1,3,5-三嗪,其特征在于,
A表示亚甲基或二亚甲基,
R1表示氢,
R2表示氢,表示甲酰基或表示乙酰基、丙酰基或者正丁酰基或异丁酰基,
R3表示甲基、乙基、正或异丙基,
R4表示氟、氯、溴,或表示甲基、乙基、正丙基或异丙基和,在A表示二亚甲基的情况下,还表示氢,
R5表示氢、氟、氯、溴,或表示甲基、乙基、正丙基或异丙基,和
Z表示未被取代的或由氟-、氯-、溴-、甲氧基-或乙氧基-取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基。
3.根据权利要求1的通式(I)噻吩基烷基氨基-1,3,5-三嗪,其特征在于,
A表示亚甲基或二亚甲基,
R1表示氢,
R2表示氢、甲酰基、乙酰基、丙酰基、正丁酰基或异丁酰基,
R3表示甲基、乙基、正丙基或异丙基,
R4表示氟、氯、溴,或表示甲基、乙基或者正丙基或异丙基和,在A表示二亚甲基的情况下,还表示氢,
R5表示氢、氟、氯、溴,或表示甲基、乙基、正丙基或异丙基,和
Z表示均未被取代或由氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正丙基或异丙基。
4.制备权利要求1的通式(I)的噻吩基烷基氨基-1,3,5-三嗪的方法,
其中
A、R1、R2、R3、R4、R5和Z如权利要求1中定义,其特征在于,
(a)使通式(II)的双胍
其中
A、R1、R2、R3、R4和R5如权利要求1中定义,
或通式(II)化合物的酸加合物与通式(III)的烷氧基羰基化合物反应
Z-CO-OR’ (III)
其中
Z如权利要求1中定义,和
R’表示具有1-4个碳原子的烷基,或
(b)使通式(IV)的取代的卤代三嗪
其中
A、R3、R4、R5和Z如权利要求1中定义,
X表示卤素,与通式(V)的含氮化合物反应
其中
R1和R2如权利要求1中定义,或
(c)使通式(VI)的取代的氨基三嗪
其中
R1、R2和Z如权利要求1中定义,和
Y1表示氟、氯、甲氧基或乙氧基,与通式(VII)的取代的烷基胺反应
其中
A、R3、R4和R5如权利要求1中定义,或
(d)使通式(Ia)的取代的2,4-二氨基-1,3,5-三嗪
其中
A、R1、R3、R4、R5和Z如权利要求1中定义,与通式(VIII)的烷基化剂或酰化剂反应
Y2-R2 (VIII)
其中
R2如权利要求1中定义,氢除外,和
Y2表示卤素、-OR2或-O-CO-R2,其中R2定义如上。
5.除草组合物,其特征在于,它们包含至少一种权利要求1的噻吩基烷基氨基-1,3,5-三嗪。
6.防治单子叶和双子叶作物中的单子叶和双子叶杂草的方法,其特征在于,使权利要求1的噻吩基烷基氨基-1,3,5-三嗪作用于所述杂草或其栖生地。
7.权利要求1的噻吩基烷基氨基-1,3,5-三嗪防治单子叶和双子叶作物中的单子叶和双子叶杂草的应用。
8.制备除草组合物的方法,其特征在于,将权利要求1的噻吩基烷基氨基-1,3,5-三嗪与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19816055.0 | 1998-04-09 | ||
DE19816055A DE19816055A1 (de) | 1998-04-09 | 1998-04-09 | Thienylalkylamino-1,3,5-triazine |
Publications (2)
Publication Number | Publication Date |
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CN1296484A CN1296484A (zh) | 2001-05-23 |
CN1162426C true CN1162426C (zh) | 2004-08-18 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB998048119A Expired - Fee Related CN1162426C (zh) | 1998-04-09 | 1999-03-26 | 噻吩基烷基氨基-1,3,5-三嗪类及其作为除草剂的应用 |
Country Status (11)
Country | Link |
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US (1) | US6420313B1 (zh) |
EP (1) | EP1087965A1 (zh) |
JP (1) | JP2002511468A (zh) |
KR (1) | KR100658483B1 (zh) |
CN (1) | CN1162426C (zh) |
AU (1) | AU743810B2 (zh) |
BR (1) | BR9909913A (zh) |
CA (1) | CA2327793A1 (zh) |
DE (1) | DE19816055A1 (zh) |
MX (1) | MXPA00009827A (zh) |
WO (1) | WO1999052904A1 (zh) |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3753986A (en) * | 1970-04-02 | 1973-08-21 | Exxon Research Engineering Co | Triazine herbicides |
US3816419A (en) * | 1972-10-27 | 1974-06-11 | American Cyanamid Co | Substituted s-triazines |
JPS62222166A (ja) | 1985-12-24 | 1987-09-30 | Toshiba Corp | 交流信号検出装置 |
JPS63222166A (ja) | 1987-03-10 | 1988-09-16 | Idemitsu Kosan Co Ltd | トリアジン誘導体,その製造方法およびそれを含有する除草剤 |
DE19531084A1 (de) | 1995-08-24 | 1997-02-27 | Hoechst Schering Agrevo Gmbh | 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE19641691A1 (de) * | 1996-10-10 | 1998-04-16 | Bayer Ag | Substituierte 2-Amino-4-alkylamino-1,3,5-triazine |
DE19641693A1 (de) * | 1996-10-10 | 1998-04-16 | Bayer Ag | Substituierte 2-Amino-4-alkylamino-1,3,5-triazine |
DE19641694A1 (de) * | 1996-10-10 | 1998-04-16 | Bayer Ag | Substituierte 2,4-Diamino-1,3,5-triazine |
DE19744711A1 (de) | 1997-10-10 | 1999-04-15 | Bayer Ag | Substituierte 2,4-Diamino-1,3,5-triazine |
-
1998
- 1998-04-09 DE DE19816055A patent/DE19816055A1/de not_active Withdrawn
-
1999
- 1999-03-26 EP EP99919148A patent/EP1087965A1/de active Pending
- 1999-03-26 MX MXPA00009827A patent/MXPA00009827A/es unknown
- 1999-03-26 CA CA002327793A patent/CA2327793A1/en not_active Abandoned
- 1999-03-26 US US09/647,655 patent/US6420313B1/en not_active Expired - Fee Related
- 1999-03-26 WO PCT/EP1999/002089 patent/WO1999052904A1/de active IP Right Grant
- 1999-03-26 JP JP2000543461A patent/JP2002511468A/ja not_active Withdrawn
- 1999-03-26 BR BR9909913-6A patent/BR9909913A/pt not_active Application Discontinuation
- 1999-03-26 CN CNB998048119A patent/CN1162426C/zh not_active Expired - Fee Related
- 1999-03-26 KR KR1020007010600A patent/KR100658483B1/ko not_active IP Right Cessation
- 1999-03-26 AU AU37027/99A patent/AU743810B2/en not_active Ceased
Also Published As
Publication number | Publication date |
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US6420313B1 (en) | 2002-07-16 |
MXPA00009827A (es) | 2002-05-08 |
EP1087965A1 (de) | 2001-04-04 |
JP2002511468A (ja) | 2002-04-16 |
DE19816055A1 (de) | 1999-10-14 |
CN1296484A (zh) | 2001-05-23 |
AU743810B2 (en) | 2002-02-07 |
KR20010042160A (ko) | 2001-05-25 |
AU3702799A (en) | 1999-11-01 |
KR100658483B1 (ko) | 2007-02-28 |
CA2327793A1 (en) | 1999-10-21 |
BR9909913A (pt) | 2000-12-26 |
WO1999052904A1 (de) | 1999-10-21 |
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