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    • 8. 发明授权
    • Process for the preparation of 2-(imidazolin-2-yl)-3-pyridine- and
-3-quinolinecarboxylic acids
    • 制备2-(咪唑啉-2-基)-3-吡啶 - 和-3-喹啉羧酸的方法
    • US4758667A
    • 1988-07-19
    • US11077
    • 1987-02-05
    • Henry SzczepanskiDieter Durr
    • Henry SzczepanskiDieter Durr
    • A01N43/50C07D401/04C07D401/02
    • C07D401/04
    • There is disclosed a process for the preparation of 2-(imidazolin-2-yl)-3-pyridine and -3-quinolinecarboxylic acids of formula ##STR1## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.4 alkoxy, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.2 and R.sub.3 together are 1,3-butadienylene which can be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, nitro, cyano, phenyl, phenoxy, or phenyl or phenoxy, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, and R.sub.4 and R.sub.5 are each independently of the other C.sub.1 -C.sub.4 alkyl. In this process, the 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids of the above formula are obtained by reacting a 2,3-pyridine- or 2,3-quinolinedidicarboxylic acid ester of formula ##STR2## wherein R.sub.1, and R.sub.2 and R.sub.3 are as defined above and R.sub.6 is C.sub.1 -C.sub.8 alkyl, phenyl or C.sub.1 -C.sub.4 phenylalkyl with a 2-aminoalkanecarboxamide of formula ##STR3## wherein R.sub.4 and R.sub.5 are as defined above, in an inert solvent and in the presence of a strong base, direct to a salt of a 2-(imidazolin-2-yl)-3-pyridine- or -3-quinolinecarboxylic acid of the above formula, from which the free 2-(imidazolin-2-yl)-3-pyridine- or -3-quinolinecarboxylic acids of the above formula are obtained by converting said salt into an aqueous solution and adding an acid. The 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids of the above formula have herbicidal properties and can be used for controlling undesired plant growth.
    • 公开了制备式(Ⅰa)的2-(咪唑啉-2-基)-3-吡啶和-3-喹啉羧酸的方法,其中R1是氢或C1-C4烷基,R2是氢,卤素,C1- C 1-4烷基,C 1 -C 4羟烷基,C 1 -C 4烷氧基,苯基或苯基-C 1 -C 4烷基,或苯基或苯基-C 1 -C 4 - 烷基,各自被一个C 1 -C 4烷基,C 1 -C 4烷氧基或卤素取代,R 3是氢,C 1 -C 4烷基 ,苯基,苯基-C 1 -C 4 - 烷基或苯基或苯基-C 1 -C 4 - 烷基,其各自被一个C 1 -C 4烷基,C 1 -C 4烷氧基或卤素,R 2和R 3一起取代为可以被取代的1,3-丁二烯 卤素,C1-C4烷基,C1-C4烷氧基,C1-C4卤代烷基,C1-C4烷基磺酰基,硝基,氰基,苯基,苯氧基或苯基或苯氧基,各自被一个C1-C4烷基,C1-C4烷氧基或卤素取代,R4和 R5各自独立地为C 1 -C 4烷基。 在该方法中,上式的2-(咪唑啉-2-基)-3-吡啶 - 和-3-喹啉羧酸是通过使式(I)的2,3-吡啶 - 或2,3-喹啉二甲酸酯 其中R 1和R 2和R 3如上定义,R 6是C 1 -C 8烷基,苯基或C 1 -C 4苯基烷基,其中R 4和R 5如上所定义,在惰性溶剂中,式 在强碱存在下,直接导入上式的2-(咪唑啉-2-基)-3-吡啶 - 或-3-喹啉羧酸的盐,游离的2-(咪唑啉-2-基) 吡啶-3-基)-3-吡啶 - 或-3-喹啉羧酸是通过将所述盐转化成水溶液并加入酸得到的。 上式的2-(咪唑啉-2-基)-3-吡啶 - 和-3-喹啉羧酸具有除草性质,可用于防治不期望的植物生长。
    • 9. 发明授权
    • Heterocyclylalkyl esters of 2-imidazolinonenicotinic acids
    • 2-咪唑啉基烟酸的杂环烷基酯
    • US4741763A
    • 1988-05-03
    • US902805
    • 1986-09-02
    • Dieter DurrHenry Szczepanski
    • Dieter DurrHenry Szczepanski
    • A01N43/50A01N43/54A01N43/56A01N43/707A01N43/80C07D401/04C07D401/14C07D405/14C07D413/14C07D521/00A01N43/40
    • C07D231/12A01N43/50A01N43/54A01N43/56A01N43/707A01N43/80C07D233/56C07D249/08C07D401/04C07D401/14C07D405/14C07D413/14
    • Novel heterocyclylalkyl esters of 2-imidazolinonenicotinic acids of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth.The novel esters have the formula I ##STR1## wherein A is a straight chain or branched C.sub.1 -C.sub.4 alkylene bridge,X and Y are each independently of the other hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy or halogen, or X and Y together form the butadiene bridge, which may be substituted by halogen, cyano or C.sub.1 -C.sub.4 alkyl, andHet is a 5- or 6-membered heterocycle which contains one to three nitrogen atoms and/or one oxygen or sulfur atom and which may further contain one or two carbonyl groups, which heterocycle may also be fused to benzene rings and/or substituted by halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, nitro, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino.
    • 式I的2-咪唑啉一enic酸的新型杂环基烷基酯在芽前和芽后具有良好的选择性除草性,并且还影响或抑制植物生长。 新的酯具有式I(I)其中A是直链或支链的C 1 -C 4亚烷基桥,X和Y各自独立于另一个氢,C 1 -C 3烷基,C 1 -C 3卤代烷基,C 1 -C 3烷氧基,C 1 -C 3卤代烷氧基或卤素,或X和Y一起形成可被卤素,氰基或C 1 -C 4烷基取代的丁二烯桥,Het是含有1-3个氮原子和/或一个氮原子的5-或6-元杂环 氧或硫原子,并且其还可以含有一个或两个羰基,该杂环还可以与苯环稠合和/或被卤素,C 1 -C 3烷基,C 1 -C 3卤代烷基,C 1 -C 3烷氧基,C 1 -C 3卤代烷氧基,硝基,氨基 ,C 1 -C 3烷基氨基或二(C 1 -C 3)烷基氨基。
    • 10. 发明授权
    • Process of preparing 2-(imidazolin-2-yl)-nicotinic acid compounds
    • 制备2-(咪唑啉-2-基) - 烟酸化合物的方法
    • US4997947A
    • 1991-03-05
    • US426901
    • 1989-10-24
    • Henry SzczepanskiDieter Durr
    • Henry SzczepanskiDieter Durr
    • A01N43/50A01N43/90C07D213/80C07D401/04C07D401/14C07D405/14C07D409/14C07D471/04C07D471/14C07D491/04C07D491/048
    • C07D213/80A01N43/50A01N43/90C07D401/04C07D401/14C07D405/14C07D409/14C07D471/04C07D471/14C07D491/04
    • The invention relates to processes for the preparation of 6-substituted 2-(imidazolin-2-yl)-nicotinic acid derivatives that are distinguished by excellent herbicidal and plant growth-regulating properties, and to intermediates and processes for the preparation of the intermediates. The derivatives correspond to formula I ##STR1## in which R.sub.1 represents hydrogen or a salt, ester or amide radical,each of R.sub.2 and R.sub.3, independently of the other, represents C.sub.1 -C.sub.4 -alkyl or they together represent a C.sub.3 -C.sub.5 -alkylene radical,X represents hydrogen or methyl,Y represents hydrogen, halogen, alkyl, haloalkyl, hydroxyalkyl, alkoxy, alkylthio, phenoxy, nitro, cyano, alkylamino, phenyl, alkenyloxy or alkynyloxy, andZ represents a --CQ.sub.1 Q.sub.2 Q.sub.3 or --CQ.sub.1 Q.sub.4 Q.sub.5 radical in whichQ.sub.1 and Q.sub.2 each represents hydrogen or C.sub.1 -C.sub.4 -alkyl,Q.sub.3 represents C.sub.1 -C.sub.6 -alkoxy or phenoxy that is unsubstituted or substituted, or C.sub.3 -C.sub.6 -alkenyloxy or C.sub.3 -C.sub.6 -alkynyloxy andQ.sub.4 and Q.sub.5, together with the carbon atom to which they are bonded, represent a cycloalkyl, furyl, pyran, dioxan or dioxolan radical, orZ represents a 5- or 6-membered heterocyclic radical.
    • 本发明涉及用优异的除草和植物生长调节特性来区分的6-取代的2-(咪唑啉-2-基) - 烟酸衍生物的方法,以及制备中间体的中间体和方法。 衍生物对应于式I(I)其中R 1表示氢或盐,酯或酰胺基,R 2和R 3各自独立地表示C 1 -C 4 - 烷基,或它们一起表示C 3 -C 4 - C5-亚烷基,X代表氢或甲基,Y代表氢,卤素,烷基,卤代烷基,羟基烷基,烷氧基,烷硫基,苯氧基,硝基,氰基,烷基氨基,苯基,烯氧基或炔氧基,Z代表-CQ1Q2Q3或-CQ1Q4Q5 基团,其中Q1和Q2各自表示氢或C1-C4-烷基,Q3表示未取代或取代的C1-C6-烷氧基或苯氧基,或C3-C6-烯氧基或C3-C6-炔氧基,Q4和Q5连同 它们键合的碳原子代表环烷基,呋喃基,吡喃,二恶烷或二氧戊环,或Z表示5或6元杂环基。