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    • 4. 发明授权
    • Oxazole- and thiazolecarboxamides
    • 恶唑和噻唑甲酰胺
    • US5284821A
    • 1994-02-08
    • US919457
    • 1992-07-27
    • Klaus DitrichVolker MaywaldGerhard HamprechtAlbrecht HarreusBruno WuerzerKarl-Otto Westphalen
    • Klaus DitrichVolker MaywaldGerhard HamprechtAlbrecht HarreusBruno WuerzerKarl-Otto Westphalen
    • A01N43/74C07D263/34C07D277/56C07D417/04A01N43/76
    • C07D263/34A01N43/74C07D277/56C07D417/04
    • Oxazole- and thiazolecarboxamides of the formulae Ia and Ib ##STR1## where the substituents have the following meanings: X oxygen or sulfur;R.sup.1 hydrogen; halogen; substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, benzyl, cycloalkyl, alkenyl, alkynyl, phenyl, phenoxy or phenylthio; alkoxy; alkylthio; haloalkoxy; haloalkylthio; or a substituted or unsubstituted 5- or 6-membered heterocyclic radical;R.sup.2 formyl, 4,5-dihydrooxazol-2-yl or --COYR.sup.5 ;Y oxygen or sulfur;R.sup.5 hydrogen; cycloalkyl; substituted or unsubstituted alkyl, phenyl, benzyl, alkenyl, cycloalkenyl or alkynyl; a substituted or unsubstituted 5- or 6-membered heterocyclic radical; phthalimido; tetrahydrophthalimido; succinimido; maleiimido; one equivalent of a cation; or--N.dbd.CR.sup.6 R.sup.7 ; R.sup.6, R.sup.7 hydrogen; alkyl; cycloalkyl; phenyl; furyl or together a methylene chain of 4 to 7 members;R.sup.3 hydrogen or substituted or unsubstituted alkyl or cycloalkyl;R.sup.4 hydroxy; alkoxy; substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or naphthyl; a substituted or unsubstituted 5- or 6-membered heterocyclic radical; or R.sup.3 and R.sup.4 together are --(CH.sub.2).sub.n --Y.sub.p --(CH.sub.2).sub.q --, where n and q are 1, 2 or 3, p is 0 or 1 and Y is oxygen, sulfur or N-methyl, or form a radical of the formula --(CH.sub.2).sub.3 --CO--, and their environmentally tolerated salts,X in formula Ib not being sulfur when R.sup.1 is 3-pyridyl, R.sup.2 is CO.sub.2 CH.sub.2 CH.sub.3 or R.sup.3 is hydrogen, and X in formula Ia X not being sulfur and R.sup.1 not being thien-2-yl when YR.sup.5 is OH, R.sup.3 is hydrogen and R.sup.4 is methyl, processes for manufacturing such compounds and herbicidal agents containing compounds of the formulae Ia or Ib as active ingredients.
    • 式Ia和Ib的恶唑和噻唑甲酰胺其中取代基具有以下含义:X氧或硫; R1氢; 卤素; 取代或未取代的C 1 -C 6烷基,苄基,环烷基,烯基,炔基,苯基,苯氧基或苯硫基; 烷氧基 烷硫基 卤代烷氧基 卤代烷硫基; 或取代或未取代的五元或六元杂环基; R2甲酰基,4,5-二氢恶唑-2-基或-COYR 5; Y氧或硫; R5氢; 环烷基 取代或未取代的烷基,苯基,苄基,烯基,环烯基或炔基; 取代或未取代的5或6元杂环基; 邻苯二甲酰亚氨基 四氢邻苯二甲酰亚胺 琥珀酰亚胺 马来西亚 一个阳离子; 或-N = CR 6 R 7; R6,R7氢; 烷基; 环烷基 苯基; 呋喃基或一起形成4至7个成员的亚甲基链; R3氢或取代或未取代的烷基或环烷基; R4羟基 烷氧基 取代或未取代的烷基,环烷基,烯基,炔基,苯基或萘基; 取代或未取代的5或6元杂环基; 或者R 3和R 4一起是 - (CH 2)n -Yp-(CH 2)q - ,其中n和q是1,2或3,p是0或1,Y是氧,硫或N-甲基,或形成 式((CH2)3-CO-)及其环境耐受盐的基团,当R1为3-吡啶基时,式Ib中的X不为硫,R2为CO2CH2CH3或R3为氢,式Ia中的X为硫, 并且当YR 5是OH时,R 1不是噻吩-2-基,R 3是氢,R 4是甲基,制备这种化合物的方法和含有式Ia或Ib化合物的除草剂作为活性成分。
    • 5. 发明授权
    • O-benzyloxime ethers and crop protection agents containing these compounds
    • O-苄氧基肟醚和含有这些化合物的作物保护剂
    • US06316459B1
    • 2001-11-13
    • US08328516
    • 1994-10-25
    • Siegbert BrandUwe KardorffReinhard KirstgenBernd MuellerKlaus OberdorfHubert SauterGisela LorenzEberhard AmmermannChristoph KuenastAlbrecht Harreus
    • Siegbert BrandUwe KardorffReinhard KirstgenBernd MuellerKlaus OberdorfHubert SauterGisela LorenzEberhard AmmermannChristoph KuenastAlbrecht Harreus
    • A01N4348
    • C07D209/48A01N37/36A01N37/38A01N37/50A01N43/16C07C251/60C07C255/64C07C257/06C07C323/47C07C323/56C07C323/60C07C327/22C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07D309/04C07D309/12
    • O-Benzyloxime ethers of the formula I where X is substituted or unsubstituted CH2, NOalkyl Y is O, S, NR5 R1, R2, R5 are H, alkyl Z1, Z2 are H, halogen, methyl, methoxy, cyano R3, R4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, N(R6)2, where R6 is H, alkyl, substituted or unsubstituted phenyl, —CO—N(R7)2, where R7 is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy, R3 and R4 together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, and R3 or R4 may be halogen, or  may be  where n is an integer from 1 to 4, and R8 is, or, when n>1, the R8's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy. and crop protection agents containing these compounds.
    • 式I的O-苄氧基肟醚是取代或未取代的CH 2,N 2烷基Y是O,S,NR 5 R 1,R 2,R 5是H,烷基Z 1,Z 2是H,卤素,甲基,甲氧基,氰基R 3,R 4是氢,氰基, 未取代的烷基,烯基,环烷基,环烯基,炔基,烷氧基,卤代烷氧基,烷硫基,苄硫基,烷基羰基,取代或未取代的苯基羰基,取代或未取代的苄基羰基,烷氧基羰基,取代或未取代的苯氧基羰基,取代或未取代的苄氧羰基,N(R6) R6是H,烷基,取代或未取代的苯基,-CO-N(R7)2,其中R7是H,取代或未取代的烷基,取代或未取代的芳基,取代或未取代的芳氧基,取代或未取代的芳硫基,取代或未取代的杂芳基, 取代或未取代的杂芳氧基,取代或未取代的杂芳硫基,取代或未取代的杂环基,取代或未取代的杂环氧基,R3和R4至 可以形成被取代或未取代的碳环或杂环,R 3或R 4可以是卤素,或者可以是1〜4的整数,R 8是,或者当n> 1时,R 8相同或不同, C 1 -C 4烷氧基,C 1 -C 4卤代烷基,C 1 -C 4卤代烷氧基,芳基,芳氧基,苄氧基,杂芳基或杂环氧基和作物 含有这些化合物的保护剂。
    • 6. 发明授权
    • Oxazole-and thiazolecarboxyamides as herbicides
    • 恶唑和噻唑酰胺作为除草剂
    • US5256633A
    • 1993-10-26
    • US870386
    • 1992-04-17
    • Klaus DitrichVolker MaywaldGerhard HamprechtAlbrecht HarreusBruno WuerzerKarl-Otto Westphalen
    • Klaus DitrichVolker MaywaldGerhard HamprechtAlbrecht HarreusBruno WuerzerKarl-Otto Westphalen
    • A01N43/74C07D263/34C07D277/56C07D417/04A01N43/78
    • C07D263/34A01N43/74C07D277/56C07D417/04
    • Oxazole- and thiazolecarboxamides of the formulae Ia and Ib ##STR1## where the substituents have the following meanings: oxygen or sulfur;hydrogen; halogen; substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, benzyl, cycloalkyl, alkenyl, alkynyl, phenyl, phenoxy or phenylthio; alkoxy; alkylthio; haloalkoxy; haloalkylthio; or a substituted or unsubstituted 5- or 6-membered heterocyclic radical;formyl, 4,5-dihydrooxazol-2-yl or --COYR.sup.5 ;oxygen or sulfur;hydrogen; cycloalkyl; substituted or unsubstituted alkyl, phenyl, benzyl, alkenyl, cycloalkenyl or alkynyl; a substituted or unsubstituted 5- or 6-membered heterocyclic radical; phthalimido; tetrahydrophthalimido; succinimido; maleiimido; one equivalent of a cation; or--N.dbd.CR.sup.6 R.sup.7 ; R.sup.6, R.sup.7 hydrogen; alkyl; cycloalkyl; phenyl; furyl or together a methylene chain or 4 to 7 members;hydrogen or substituted or unsubstituted alkyl or cycloalkyl;R.sup.4 hydroxy; alkoxy; substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or naphthyl; a substituted or unsubstituted 5- or 6-membered heterocyclic radical; or R.sup.3 and R.sup.4 together are --(CH.sub.2).sub.n --Y.sub.p --(CH.sub.2).sub.q --, where n and q are 1, 2 or 3, p is 0 or 1 and Y is oxygen, sulfur or N-methyl, or form a radical of the formula --(CH.sub.2).sub.3 --CO--, and their environmentally tolerated salts,X is formula Ib not being sulfur when R.sup.1 is 3-pyridyl, R.sup.2 is CO.sub.2 CH.sub.2 CH.sub.3 or R.sup.3 is hydrogen, and X in formula Ia X not being sulfur and R.sup.1 not being thien-2-yl when YR.sup.5 is OH, R.sup.3 is hydrogen and R.sup.4 is methyl, processes for manufacturing such compounds and herbicidal agents containing compounds of the formula Ia or Ib as active ingredients.
    • 式Ia和Ib的恶唑和噻唑甲酰胺其中取代基具有以下含义:氧或硫; 氢; 卤素; 取代或未取代的C 1 -C 6烷基,苄基,环烷基,烯基,炔基,苯基,苯氧基或苯硫基; 烷氧基 烷硫基 卤代烷氧基 卤代烷硫基; 或取代或未取代的五元或六元杂环基; 甲酰基,4,5-二氢恶唑-2-基或-COYR 5; 氧或硫; 氢; 环烷基 取代或未取代的烷基,苯基,苄基,烯基,环烯基或炔基; 取代或未取代的5或6元杂环基; 邻苯二甲酰亚氨基; 四氢邻苯二甲酰亚胺 琥珀酰亚胺 马来西亚 一个阳离子; 或-N = CR 6 R 7; R6,R7氢; 烷基; 环烷基 苯基; 呋喃基或亚甲基链或4至7个成员; 氢或取代或未取代的烷基或环烷基; R4羟基; 烷氧基 取代或未取代的烷基,环烷基,烯基,炔基,苯基或萘基; 取代或未取代的5或6元杂环基; 或者R 3和R 4一起是 - (CH 2)n -Yp-(CH 2)q - ,其中n和q是1,2或3,p是0或1,Y是氧,硫或N-甲基,或形成 式(CH 2)3 -CO-的基团及其环境耐受的盐,X是当R1是3-吡啶基时R2不是硫,R2是CO2CH2 CH3或R3是氢,式Ia中的X不是 硫和R1不是噻吩-2-基,当YR5是OH时,R3是氢,R4是甲基,制备这种化合物的方法和除草剂,其含有式Ia或Ib的化合物作为活性成分。
    • 8. 发明授权
    • Process for the preparation of hydroxylamine ethers and their salts and
intermediates for this purpose
    • 为此目的制备羟胺醚及其盐和中间体的方法
    • US5684200A
    • 1997-11-04
    • US454371
    • 1995-06-06
    • Albrecht HarreusNorbert GoetzVolker MaywaldHarald RangUlf MisslitzUlrich Klein
    • Albrecht HarreusNorbert GoetzVolker MaywaldHarald RangUlf MisslitzUlrich Klein
    • C07C239/20C07C251/54C07C253/30C07C255/54C07C259/06C07C209/62C07C255/62
    • C07C251/54
    • Hydroxylamine ethers I ##STR1## (where X is NO.sub.2, CN, halogen, alkyl or haloalkyl, Y is H, NO.sub.2, CN, halogen, alkyl or haloalkyl, n is 0-2 or 1-4 where Y and all radicals X are halogen and Alk is unsubstituted or substituted alkylene) and their salts with mineral acids or strong organic acids are prepared by reacting either a hydroximino compound II ##STR2## (where R.sup.1 is alkyl, R.sup.2 is alkyl or alkoxy or R.sup.1 +R.sup.2 form an alkylene chain) in the presence of an alkali metal hydroxide, alkali metal alcoholate, alkali metal bicarbonate or alkali metal carbonate as the base, or the corresponding anion II directly, with an alkylating agent III ##STR3## (where R.sup.3 is unsubstituted or substituted alkyl or unsubstituted or substituted phenyl) to give an oximino derivative IV ##STR4## said derivative is cleaved by means of a mineral acid or a strong organic acid to give the salt of I and, if desired, the latter is converted by means of a base into the free compound I. The hydroxylamine ethers I are intermediates for crop protection agents and drugs.
    • PCT No.PCT / EP93 / 03597 371日期:1995年6月6日 102(e)日期1995年6月6日PCT提交1993年12月17日PCT公布。 第WO94 / 14757号公报 日期:1994年7月7日羟胺醚I(其中X为NO 2,CN,卤素,烷基或卤代烷基,Y为H,NO 2,CN,卤素,烷基或卤代烷基,n为0-2或1-4) Y和所有基团X是卤素,Alk是未取代的或取代的亚烷基),并且它们与无机酸或强有机酸的盐通过氢肟基化合物II(其中R 1是烷基,R 2是烷基或烷氧基或 R1 + R2形成亚烷基链)在碱金属氢氧化物,碱金属醇盐,碱金属碳酸氢盐或作为碱的碱金属碳酸盐或相应的阴离子II的存在下,与烷基化剂III(III R3是未取代或取代的烷基或未取代或取代的苯基),得到肟基衍生物IV所述衍生物通过无机酸或强有机酸裂解,得到I的盐,如果需要,将后者 通过碱转化为游离化合物I.羟基 氯胺醚我是作物保护剂和药物的中间体。