CN1036370C - 含2-(2-苯并噁唑基氧)乙酰胺类衍生物的除草剂及其制法 - Google Patents
含2-(2-苯并噁唑基氧)乙酰胺类衍生物的除草剂及其制法 Download PDFInfo
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- CN1036370C CN1036370C CN92111404A CN92111404A CN1036370C CN 1036370 C CN1036370 C CN 1036370C CN 92111404 A CN92111404 A CN 92111404A CN 92111404 A CN92111404 A CN 92111404A CN 1036370 C CN1036370 C CN 1036370C
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- isopropyl
- compound
- benzoxazolyl
- oxygen
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- CYYHGURRPGNXPM-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)acetamide Chemical class C1=CC=C2OC(OCC(=O)N)=NC2=C1 CYYHGURRPGNXPM-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
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- 238000000034 method Methods 0.000 claims abstract description 16
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- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
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- 238000002360 preparation method Methods 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
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- SUXLFFOTNJAQPN-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzoxazol-2-yl)oxy]-n-phenyl-n-propan-2-ylacetamide Chemical compound N=1C2=CC=C(Cl)C=C2OC=1OCC(=O)N(C(C)C)C1=CC=CC=C1 SUXLFFOTNJAQPN-UHFFFAOYSA-N 0.000 abstract 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(I)的新的2-(2-苯并唑基氧)乙酰胺类衍生物，它们的制备方法以及作为除草剂的应用。本发明还提供了含所述化合物的除草剂和其制法。在式(I)中，各取代基的定义见说明书中。
Description
本发明涉及新的2-(2-苯并噁唑基氧)乙酰胺类衍生物，它们的制备方法以及作为除草剂的应用。
已知某些2-(2-苯并噁唑基氧)乙酰胺类衍生物，例如，化合物N-异丙基-2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺，具有除草性能(参见例如，DE-A 2,903,966；EP-A5,501；US-A 4,509,971；US-A 4,833,243；DE-A 3,038,599；DE-A 3,038,652；DE-A3,418,168；EP-A 161,602；US-A 4,784,682；DE-A 3,724,467)。
但是，这些先前已知的化合物对目标杂草的除草活性和重要农作物对它们的耐受度并非在所有应用领域都完全令人满意。
已经发现了通式(I)的新的2-(2-苯并噁唑基氧)乙酰胺类衍生物
其中，R代表氢、卤素、烷基或卤代烷基，Ar代表可任选取代的芳基，但是化合物N-异丙基-2-(2-苯并噁唑基氧)-N-乙酰苯胺和N-异丙基-2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺除外。
另外还发现，当化学式(II)的苯并噁唑衍生物与化学式(III)的2-羟基乙酰胺反应时(如果合适，在有稀释剂和反应助剂存在下反应)，得到了通式(I)的新的2-(2-苯并噁唑基氧)-乙酰胺类衍生物
式(II)中，X代表卤素或烷基磺酰基，R的意义如上所述；式(III)中，Ar的意义如上所述。
最后，已经发现通式(I)的新2-(2-苯并噁唑基氧)-乙酰胺具有除草性能。
出乎意料的是，本发明的这种通式(I)的新的2-(2-苯并噁唑基氧)乙酰胺，与先有技术中已知的2-(2-苯并噁唑基氧)乙酰胺(例如N-异丙基2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺)相比，对目标杂草显示出好得多的除草活性，而重要作物对它的耐受度同样好。
式(I)提供了本发明的新的2-(2-苯并噁唑基氧)乙酰胺类衍生物的一般定义。在优选的式(I)化合物中，R代表氢、氟、氯、溴、碘、有1到8个碳原子的直链或支链烷基、或是有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基；Ar代表苯基或萘基，各自任选地被相同或不同的取代基单取代或多取代，每种情形的合适取代基为：卤素、氰基、硝基、有1到6个碳原子的直链或支链烷基、烷氧基或烷硫基，有1到6个碳原子和1到13个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基，但是化合物N-异丙基2-(2-苯并噁唑基氧)-N-乙酰苯胺和N-异丙基2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺除外。
特别优选的式(I)化合物中，R代表氢、氟、氯、溴、有1到6个碳原子的直链或支链烷基、或是有1到3个碳原子和1到7个相同或不同卤原子的直链或支链卤代烷基；Ar代表可任选地被相同或不同取代基单取代到三取代的苯基，合适的取代基是：卤素、氰基、硝基，有1到4个碳原子的直链或支链烷基、烷氧基或烷硫基，有1到4个碳原子和1到9个相同或不同卤原子的直链或支链卤代烷基、卤代烷氧基或卤代烷硫基，但是化合物N-异丙基2-(2-苯并噁唑基氧)-N-乙酰苯胺和N-异丙基2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺除外。
在最优选的式(I)化合物中，R代表氢、氯、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基，或是三氟甲基；Ar代表可任选地被相同或不同取代基单取代或双取代的苯基，合适的取代基是：氟、氯、溴、硝基、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、甲硫基、三氟甲基、三氟甲氧基和/或三氟甲硫基，但是化合物N-异丙基2-(2-苯并噁唑基氧)-N-乙酰苯胺和N-异丙基2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺除外。
请参阅在制备实施例中提到的各个化合物。
例如，如果使用2-氯-5-甲基苯并噁唑和N-异丙基2-羟基-N-乙酰苯胺作为起始物，本发明方法的反应过程可以用以下反应式表示：
式(II)提供了实施本发明方法所需的起始物苯并噁唑衍生物的一般定义。在式(II)中，R最好是在对本发明式(I)化合物的说明中已作为优选取代基提到的那些基团。
式(II)中的X最好代表氟、氯或溴，或是有1到4个碳原子的直链或支链烷磺酰基，尤其是氯或甲磺酰基。
式(II)的苯并噁唑衍生物是已知化合物，或者可以用与已知方法类似的方法得到(例如参见欧洲专利141,053；欧洲专利43,573；德国专利3,025,910；Am.Ch em.J.21：111，1899；J.Prakt.Chem.42(2)：445，1890；德国专利1,164,413)。
式(III)提供了实施本发明方法还需要的起始物2-羟基乙酰胺的一般定义。在式(III)中，Ar最好代表在对本发明式(I)化合物的说明中已作为优选取代基提到的那些基团。
式(III)的2-羟基乙酰胺也是已知的(例如参见德国专利3,821,600)。
适于进行本发明方法的稀释剂是惰性有机溶剂。这些溶剂具体包括：可任选卤化的脂族、脂环族或芳族烃类，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、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚；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，例如二甲基亚砜；或醇类，例如甲醇、乙醇、正丙醇或异丙醇、正丁醇、异丁醇、仲丁醇或叔丁醇。
本发明的方法最好在有合适的反应助剂存在下进行。合适的反应助剂都是惯用的无机碱和有机碱。最好使用以下碱：碱金属的氢化物、氢氧化物、氮化物、醇盐、碳酸盐或碳酸氢盐，例如氢化钠、氨基钠、氢氧化钠、甲醇钠、乙醇钠、叔丁醇钾、碳酸钠或碳酸氢钠；或者叔胺，例如三乙胺、N，N-二甲基苯胺、吡啶、N，N 二甲基氨基吡啶、重氮二环辛烷(DABCO)、重氮二环壬烯(DBN)或重氮二环十一碳烯(DBU)。
在进行本发明的方法时，反应温度可以在相当大的范围内变化。一般来说，该方法在-40℃和120℃之间的温度下进行，最好是在-20℃和60℃之间的温度下进行。
为了进行本发明的方法，通常每摩尔式(II)苯并噁唑衍生物使用1.0到2.0摩尔、优选1.0到1.5摩尔的式(III)2-羟基乙酰胺，如果合适的话，使用0.1到2.0摩尔、优选1.0到1.2摩尔的反应助剂。
进行反应，并且用已知方法处理和分离反应产物(在这方面参见例如欧洲专利348,734、欧洲专利5,501、德国专利3,821,600或制备实施例)。
式(I)的最终产物借助惯用的方法纯化，例如用柱色谱法或重结晶法。这些产物借助熔点鉴定，或者在非结晶化合物的情形，借助折射率或核磁共振氢谱(1H-NMR)鉴定。
本发明的活性化合物可以用来作为落叶剂、干燥剂、阔叶植物破坏剂，尤其是杂草杀伤剂。所谓杂草，在最概括的意义上，应理解成在生长地不需要的所有植物。本发明的物质是作为广谱的还是作为选择性的除草剂起作用，主要取决于用量。
本发明的活性化合物可以用于例如以下植物：
以下各属的双子叶杂草：欧白芥属、独行菜属、拉拉藤属、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、番薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节菜属、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、车轴草属、毛茛属和蒲公英属。
以下各属的双子叶作物：棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、野豌豆属、烟草属、番茄属、落花生属、芸苔属、莴苣属、香瓜属、南瓜属。
以下各属的单子叶杂草、稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、_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、慈茹属、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、看麦娘属和Apera。
以下各属的单子叶作物：稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
但是，本发明活性化合物的用途决不限于这些属的植物，而是可以以同样的方式扩展到其它植物。
根据使用浓度，这些化合物适合用来全面防治杂草，例如在工业场所和铁轨上，以及在有树或无树的道路和广场上的杂草。同样，这些化合物可以用来防治多年生作物(例如树林)、观赏树木、果园、葡萄园、柑桔园、坚果园、香蕉种植园、咖啡种植园、茶场、橡胶园、油棕种植园、可可种植园、浆果林和啤酒花栽培地、绿化草地、跑马场和牧场中的杂草，还可用来选择性地防治一年生作物中的杂草。
在这方面，本发明的活性化合物可以特别成功地用来防治单子叶和双子叶作物(例如棉花和稻)中的单子叶杂草。
这些活性化合物可以转化成惯用的制剂，例如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、糊剂、可溶性粉剂、粒剂、悬浮剂-乳剂浓缩物、用活性化合物浸渍的天然和合成物质，以及很细的聚合物胶囊。
这些制剂按已知方式生产，例如，将活性化合物与作为增量剂的液体溶剂和/或固体载体相混合，还可以任选地使用表面活性剂，它们是乳化剂和/或分散剂和/或发泡剂。
在用水作增量剂的情形，也可以用(例如)有机溶剂作为辅助溶剂。合适的液体溶剂大致有：芳族化合物，例如二甲苯、甲苯或烷基萘；氯代芳族化合物和氯代脂族烃，例如氯苯、氯乙烯或二氯甲烷；脂族烃，例如环己烷或链烷烃，如石油馏分、矿物油和植物油；醇类，例如丁醇或二醇，以及它们的醚和酯；酮类，例如丙酮、甲乙酮、甲基异丁基酮或环己酮；强极性溶剂，例如二甲基甲酰胺和二甲基亚砜；以及水。
合适的固体载体包括：例如铵盐和磨细的天然矿物，例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱土或硅藻土；磨细的合成矿物，例如高度分散的二氧化硅、氧化铝和硅酸盐。适合作为粒剂固体载体的包括：例如粉碎和分级的天然岩石，例如方解石、大理石、浮石、海泡石和白云石，以及合成的无机和有机粉粒；有机物颗粒，例如锯末、椰子壳、玉米芯和烟梗等。适合作为乳化剂和/或发泡剂的有：例如非离子型和阴离子型乳化剂，例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚，如烷芳基聚乙二醇醚、烷磺酸盐、烷基硫酸盐、芳磺酸盐和清蛋白水解产物。适合作为分散剂的有：例如木质素亚硫酸盐废液和甲基纤维素。
制剂中可以使用粘合剂，例如羧甲基纤维素和粉状、粒状或胶乳状的天然的与合成的聚合物(例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯)以及天然的磷脂(例如脑磷脂和卵磷脂)和合成的磷脂。还可以加入矿物油和植物油。
可以使用着色剂，例如无机颜料(如氧化铁、二氧化钛和普鲁士蓝)和有机染料(如茜素染料、偶氮染料和金属酞菁染料)，以及微量的营养素，例如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中一般含有0.1％到95％(重量)的活性化合物，优选0.5％到90％。
对防治杂草而言，本发明的活性化合物本身或其制剂，也可以与已知的除草剂、成品制剂或者罐装混合物混合使用。
适合用于混合物的除草剂是已知的除草剂，例如酰替苯胺类，如diflufenican和敌稗；芳基羧酸类，如二氯吡啶甲酸、麦草畏和毒莠定；芳氧基链烷酸类，例如2，4-滴、2，4-滴丁酸、2，4-滴丙酸、fluroxypyr、2甲4氯、2甲4氯丙酸和定草酯；芳氧基苯氧基链烷酸酯，例如，氯甲草、fenoxaprop-ethyl、fluazifop-butyl、holoxyfop-methyl和quizalofop-ethyl；吖嗪酮类，例如Chloridazon和达草灭；氨基甲酸酯类，例如氯苯胺灵、异苯敌草、苯敌草和苯胺灵；乙酰氯苯胺类，例如草不绿、乙基乙草安、丁草锁、metazachlor、丙草安、Pretilachlor和毒草安；二硝基苯胺类，例如黄草消、胺硝草和氟乐灵；二苯醚类，例如氟锁草醚、治草醚、fluoroglycofen、fomesafen、halosafen、lactofen和氟硝草醚；尿素类，例如绿麦隆、磷胺、伏草隆、异丙隆、利谷隆和噻唑隆；羟胺类，例如枯杀达、Clethodim、Cycloxydim、Sethoxydim和tralkoxydim；咪唑啉酮类，例如imazethapyr、imazamethabenz、imazapyr和imazaquin；腈类，例如溴苯腈、敌草腈和碘苯腈；氧代乙酰胺类，例如mefenacet；磺酰脲类，例如amidosulfuron、bensulfuron-methyl、Chlorimuron-ethyl、Chlorsulfuron、Cinosulfuron、metsulfuron-methyl、nicosulfuron、primisulfuron、pyrazosulfuron-ethyl、thifensulfuron-methyl、triasulfuron和tribenuron-methyl；硫代氨基甲酸酯类，例如苏达灭、草灭特、燕麦敌、扑草灭、esprocarb、草达灭、prosulfocarb、杀草丹和野麦畏；三嗪类，例如阿特拉津、草净津、西玛津、西草净、去草净和特丁津；三嗪酮类，例如六嗪酮(hexazinone)、苯嗪草和赛克津；其它除草剂，例如，氨基三唑、benfuresate、噻草平、Cinmethylin、Clomazone、Clopyralid、苯敌快、dithiopyr、唑啶草、氟氯酮、glufosinate、草甘膦、isoxaben、达草止、quinchlorac、quinmerac、Sulphosate和tridiphane。
也可以与其它已知的活性化合物，例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂和土壤结构改良剂等，构成混合物使用。
这些活性化合物可以原样使用、以其制剂形式使用、或是以由其进一步稀释而配制成的使用形式使用，例如备用溶液、悬浮剂、乳剂、粉剂、糊剂和粒剂。它们以惯用的方式使用，例如洒水、喷药、喷雾或撒布。
本发明的活性化合物可以在植物出芽前或出芽后施用，也可以在播种前掺入土壤中。
活性化合物的用量可以在相当大的范围内变化。这主要取决于所要求的效果。一般来说，每公顷土壤表面用量为10克到10千克活性化合物，优选每公顷用量在50克到5千克之间。
以下实施例说明了本发明活性化合物的制备和使用。制备实施例实施例1
在-20℃，于搅拌下将2.4克(0.06摩尔)氢氧化钠在10毫升水中的溶液滴加到含有9.8克(0.05摩尔)N-异丙基-羟基-N-乙酰苯胺和7.6克(0.045摩尔)2-氯-5-甲基-苯并噁唑的100毫升丙酮中，然后将混合物在0到5℃下搅拌3小时。为进行后处理，向混合物中加水，搅拌，直到产物结晶，随后将其抽滤并干燥。
得到13.6克(理论值的85％)的2-(5-甲基苯并噁唑-2-基氧)-N-异丙基-N-乙酰苯胺，熔点108℃。
按照相应的方式和以下的一般制备程序，得到下列通式(I)的2-(2-苯并噁唑基氧)-乙酰胺：
表1
表1
表1
表1
表1
表1
表1
表1
表1
表1
表1
表1
表1应用实施例：
在以下的应用实施例中，使用下面列出的化合物N-异丙基-2-(6-氯苯并噁唑-2-基氧)-N-乙酰苯胺(参见德国专利3,418,168；3,724,467)作为对照物质。
实施例A芽前试验溶剂：5重量份的丙酮乳化剂：1重量份的烷芳基聚乙二醇醚
为制备合适的活性化合物制剂，将1重量份的活性化合物与所述量的溶剂混合，加入所述数量的乳化剂，用水将此浓缩物稀释到所要求的浓度。
将试验植物的种子播种在正常的土壤中，24小时后用活性化合物制剂浇洒。最好是保持单位面积上的水量恒定。制剂中活性化合物的浓度并不重要，起决定作用的只是每单位面积上施用的活性化合物的量。三周后，植物的损伤程度按与未处理对照样相比的损伤百分数定级。其中的数字表示：
0％＝无作用(与未处理的对照样相同)
100％＝完全破坏
在这一试验中，采用(例如)下列制备实施例的化合物：1、2、3、5、6、7、10、12、14、16、17、18、20、22、23、26、43、44、49、51、53、54和58，显示出比先有技术明显优越的活性。
Claims (2)
1.除草剂，其特征在于它含有至少一种通式(I)的2-(2-苯并噁唑基氧)乙酰胺类衍生物其中，R代表氢、卤素、C1-4烷基或C1-4卤代烷基，Ar代表被相同或不同的取代基单取代或二取代的苯基，其中取代基是：卤素、C1-4烷基、C1-4烷氧基、C1-4烷硫基和C1-4卤代烷基。
2.制备除草剂的方法，其特征在于，将根据权利要求1的通式(I)化合物与增量剂和/或表面活性剂混合。
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| JPS56140981A (en) * | 1980-04-07 | 1981-11-04 | Nippon Tokushu Noyaku Seizo Kk | Substituted acetanilide compound, its preparation and herbicide containing the same as active constituent |
| DE3038652A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | 5-chlor-benzoxazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3038599A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Substituierte benzazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3109582A1 (de) * | 1981-03-13 | 1982-10-28 | Bayer Ag, 5090 Leverkusen | N-(2,2,2-trifluorethyl)-n-alkyl- azolyloxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide sowie neue zwischenprodukte zu ihrer herstellung |
| JPS57183764A (en) * | 1981-04-06 | 1982-11-12 | Nippon Tokushu Noyaku Seizo Kk | Substituted acetanilide compound, its preparation, and herbicide |
| US4456466A (en) * | 1982-11-08 | 1984-06-26 | Ppg Industries, Inc. | Herbicidally active benzoxazolyl acetophenone oxime derivatives |
| DE3418168A1 (de) * | 1984-05-16 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | 6-chlorbenzazolyloxyacetamide |
| DE3422861A1 (de) * | 1984-06-20 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von heteroaryloxyacetamiden |
| DE3724467A1 (de) * | 1987-07-24 | 1989-02-02 | Bayer Ag | 6-chlorbenzoxazolyl-oxyacetanilide |
-
1991
- 1991-10-11 DE DE4133673A patent/DE4133673A1/de not_active Withdrawn
-
1992
- 1992-09-28 EP EP92116538A patent/EP0537539A1/de not_active Withdrawn
- 1992-10-02 US US07/956,127 patent/US5328897A/en not_active Expired - Fee Related
- 1992-10-06 JP JP29087592A patent/JP3221936B2/ja not_active Expired - Fee Related
- 1992-10-08 KR KR1019920018517A patent/KR100239580B1/ko not_active IP Right Cessation
- 1992-10-09 BR BR929203936A patent/BR9203936A/pt not_active Application Discontinuation
- 1992-10-10 CN CN92111404A patent/CN1036370C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR930007918A (ko) | 1993-05-20 |
| DE4133673A1 (de) | 1993-04-15 |
| KR100239580B1 (ko) | 2000-02-01 |
| JP3221936B2 (ja) | 2001-10-22 |
| BR9203936A (pt) | 1993-04-27 |
| US5328897A (en) | 1994-07-12 |
| EP0537539A1 (de) | 1993-04-21 |
| CN1071664A (zh) | 1993-05-05 |
| JPH05213912A (ja) | 1993-08-24 |
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