CN1025186C - 含取代的二环庚二酮衍生物的除草剂 - Google Patents

含取代的二环庚二酮衍生物的除草剂 Download PDF

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CN1025186C
CN1025186C CN90103422A CN90103422A CN1025186C CN 1025186 C CN1025186 C CN 1025186C CN 90103422 A CN90103422 A CN 90103422A CN 90103422 A CN90103422 A CN 90103422A CN 1025186 C CN1025186 C CN 1025186C
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alkoxy
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植田昭嘉
菅繁已
阿达弘之
相原利男
富田和之
山岸秀树
保坂秀夫
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Nippon Soda Co Ltd
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Abstract

本发明涉及一些具高效除草活性，由通式(I)所代表的，取代的二环庚二酮衍生物，
(式中，R1为低级烷基，可被取代的苯基，可被取代的芳烷基，或可被取代的杂环基)；
R2为相同或不同的，卤素、烷氧基、烷基硫代，烷基磺酰基，烷基，烷氧基烷基，或烷氧基羰基，n为0到4；
R3和R4为相同或不同的，卤素或低级烷基)。

Description

本发明涉及新的取代的二环庚二酮衍生物，它们的制备方法和含所说的衍生物作为有效成分的除草剂。
在很多情况下，为减少田间除草时所耗的劳动力，农业垦种或园艺栽培都要将多种大量的除草剂用于杂草控制。然而，有时，除草剂的植物毒性会伤害植物，或者，留在田中的除草剂可能带来环境污染问题。
从而，人们期待一些化学药品的开发，它们拥有优越的药效，又对哺乳动物具较高的安全性。
已知的，揭示了与本发明的化合物类似的化合物的专利有：EP-137963，EP-135191，EP-186118，EP-186119，EP-186120，日本特公昭62-123145，EP-278907，EP-268795和EP-264737。
本发明的化合物被包含于DE3902818的权利要求中（相应于GB2215333和日本公开专利号平2-1422）。在它们的说明书中，没有关于本发明的化合物的描述。
本发明的目的是，提供一些在工业规模便于合成的除草剂，它们以较低的剂量即显示一定的药效，对作物很安全并具良好的选择性。
本发明为具有结构式（Ⅰ）的取代的二环庚二酮的衍生物或其盐类：
Figure 901034223_IMG2
（Ⅰ）
（式中，R1为低级烷基，可被取代的苯基，可被取代的芳烷基，或可被取代的杂环基;
R2为一个相同或不同的，卤素，烷氧基，烷基硫代，烷基磺酰基，烷基，烷氧基烷基，或一个烷氧基羰基，n为0到4;
R3和R4为相同或不同的，氢或低级烷基）。
所说的R1的苯基、芳烷基和杂环基的取代基为相同或不同的，卤素，羟基、硝基、氰基、烷基、链烯基、卤代烷基、卤代链烷基、烷氧基、卤烷氧基、卤链烯氧基、烷基硫代，链烯基硫代、炔基硫代、卤烷基硫代、卤链烯基硫代、单烷基氨基、二烷基氨基、烷氧基烷基硫代、烷基硫代烷氧基硫代、烷氧基羰基、烷基羰基烷氧基、烷基羰基、烷氧基氨基、烷基磺酰基、链烯基磺酰基、炔基磺酰基、烷氧基烷基磺酰基、烷基硫代烷基磺酰基、烷基磺酰基烷基磺酰基、卤烷基磺酰基、烷氧基羰基烷基硫代，烷氧基羰基烷基亚磺酰基和烷氧基羰基烷基磺酰基，可被取代的苯基，可被取代的芳烷基，或被取代的杂环基，和以可被取代的杂环基取代的烷基。
所说的杂环基包括：吡啶基，嘧啶基，噻吩基，呋喃基，吡唑基，吡咯基，咪唑基，哒嗪基， 吡嗪基，吲哚基及其它。
本发明的化合物展示了在高地条件下以土壤处理或小块地叶面处理的高的除草活性。特别是将此药物直接喷施于植物叶面上时，它对蟋蟀草（crabgrass）、碎米莎草（rice    flatsedge）、绒毛草（velvetheaf）、红根藜（redroot    pigweed）等高地杂草非常有效。其中一些化合物对小麦和大豆具选择性。
其中另一些化合物对作物，观赏植物和果树显示了植物生长抑制作用。
有些化合物也显示了对于稻类作物的高选择性和对于稗子，异型莎草、野慈菇和日本蔗草等的高除草活性。
此外，本发明的化合物可被用于果园、草坪、铁路沿线和空地等的杂草控制。
本发明的最佳实施模式：
本发明的化合物由下述方法制备。
制备方法（a）
Figure 901034223_IMG3
（R1、R2、R3、R4和n如上定义，Q为一离去基团）。
在此过程中，化合物（Ⅰ）由化合物（Ⅱ）在有2摩尔或过量碱的存在下于一溶剂中反应制得，温度从-20°到所用溶剂的沸点，最好是0-50℃，时间从30分钟到数十小时。
Q的离去基团包括卤素，烷基磺酸盐和苯基磺酸盐。
所用的碱包括：碱金属氢氧化物如KOH和NaOH，碱土金属的氢氧化物，三（C1-C
Figure 901034223_IMG4
烷基）胺，吡啶，DBU，t-BuOK，Triton B，碳酸钠，磷酸钠等。所用溶剂包括：水，醇，二氧甲烷，苯，甲苯，乙酸乙酯，二甲基甲酰胺，THF，二甲氧基乙烷，乙腈或此类溶剂。
制备方法（b）
本发明的化合物中，除了那些烷氧基羰基是在双环的5位上的化合物以外，单取代化合物可根据下述反应制得。
Figure 901034223_IMG5
（式中，r为烷基）。
如果这些化合物在5位上有不同的取代基如（Ⅰ）′，或在5位上有一个取代基如（Ⅰ）″，则立体异构体相对于环丙烷环而存在。
在（Ⅰ）″是根据上述制备方法（a）直接得出时，通常产生反式结构。在此制备方法中，可能在（Ⅰ）′阶段分离出顺，反式结构，适当地选择这些方法可制备得（Ⅰ）″的顺式或反式化合物。
本发明的原料化合物和化合物（Ⅰ）具有旋光异构体，且大量的互变异构体可能存在于下式中：
Figure 901034223_IMG6
（式中，R1、R2、R3、R4和n如上定义）。如此形式的化合物皆包括于本发明。
如果，以上述方法制备时，化合物（Ⅰ）包含一个自由羟基基团，则该化合物的盐（农业上或园艺上可用的盐）、烯胺及其类似物、丙烯酸盐（或酯）磺酸盐（或酯）、氨基甲酸盐（或酯）或醚可从所说的化合物衍生。
农业上或园艺上可用的适当的盐包括，钠盐，钾盐，钙盐，铵盐等。
铵盐举例有，用结构式N+RaRbRcRd（其中，Ra，Rb，Rc和Rd分别从氢和C1-10的烷基基团中选出，某些情况下，例如，烷基由羟基取代）所表示的带离子的盐。如果，在一些情况下，Ra、Rb、Rc和Rd之任一个为取代的烷基，则可指望其基团具有1到4个碳原子。
适当的烯胺和它们的类似物为，OH基团分别被转化为由结构式-NReRf表示的基团的化合物 （其中，例如R1为烷基或具有1到6个碳原子的某些情况下可被取代的芳基，或例如苯基，而R1为氢，或例如烷基或具有1到6个碳原子的某些情况下可被取代的芳基，或例如苯基），卤素或SRh（其中，Rg为如上述基团Ro同样的基团）。
适当的丙烯酸盐或醚衍生物是，其OH基团分别被转化为由结构式-OCORh或-ORh（其中，R为如上述基团R9同样的基团）所表示的基团的化合物。
适当的氨基甲酸盐衍生物是，其OH基团被转化为由结构式-OC（O）NRiRi（其中，Ri和Ri分别为氢或与上述R同样的基团）所表示的基团的化合物。
这些衍生物可由通常的方法制得。
本发明的化合物的结构由如IR，NMR和MS这类手段确定。
参照以下实施例，本发明将一步得以详细说明。
实施例1
3-（2-硝基-4-氯苯甲酰基）二环[4，1，0]庚烷-2，4-二酮（化合物（Ⅰ-97）。
Figure 901034223_IMG7
将0.5g（1.44mmol）的5-甲磺酰基羟甲基-2-（2-硝基-4-氯苯甲酰基）环己烷-1，3-二酮溶于15ml的乙醇中，在室温下搅拌加入2ml的氢氧化钠水溶液（氢氧化钠：0.17g，4.31mmol），再在室温下搅拌生成的混合液2小时。反应完成后，蒸馏去除溶剂。向所得残余物加入50ml乙酸乙酯和10ml的水，使其溶解。加入稀盐酸，直至水层呈酸性。有机层以饱和盐水洗涤后用硫酸镁干燥。蒸馏去除溶剂。所得残余物以硅胶柱色谱法提纯（洗脱液∶氯仿），给出0.38g（产率：86%）的预期的浅黄色晶体产品，其熔点为132-134℃。
实施例2
3-（2-氯-4-甲基磺酰基-3-甲氧基苯甲酰基）-顺式-5-甲基-顺式-二环[4，1，0]庚烷-2，4-二酮（化合物（Ⅰ-195）。
将1.19g（2.6mmol）的3-（2-氯-4-甲烷磺酰基-3-甲氧基苯甲酰基）-反式-5-乙氧基羰基-顺式-5-甲基-顺式-二环[4，1，0]庚烷-2，4-二酮溶解于7.8ml（7.8mmol）的1N NaOH中，同时以冰水冷却，随后，在室温下反应4小时。反应完成后，加入20ml冰水和20ml的乙酸乙酯，在以冰水冷却的同时，用1N HCl中和，然后脱去羧基。有机层先后经水和饱和盐水洗涤后，用MgSO4干燥。蒸馏去除溶剂。残余物以柱色谱法提纯（苯∶乙酸乙酯＝5∶1），给出0.29g的预期的白色晶体产品，熔点为132-135°。所得的顺式形式和如实施例1所用相同方式合成的反式形式都用NMR表征之。
本发明的化合物的代表性例子，包括上述实施例中所得的化合物，示于表1到3。
Rx、Ry和Rz为分别列于表中的下述取代基。其物理性能栏内的反式和顺式为二环环和环丙烷环5位上的取代基的空间构型。
Figure 901034223_IMG9
（表见文后）
如上所述，这些化合物具有优越的除草活性。这些化合物可作为芽前处理而直接施于土壤，或作为芽后处理直接施于植物叶面，或者与土壤紧密混合。这些化合物可以1g或1g以上/每10公亩的 量施于土壤或植物叶面。
具有本发明的化合物作为其活性成分的除草剂组合物，可通过混合物以合适的载体配制成通常用于农业的化学药品形式，如可湿性粉剂、水溶性粉剂、颗粒剂、乳油和流动剂。作为固体载体，可使用滑石粉、白碳（二氧化硅）、膨润土、粘土、硅藻土或类似物。作为液体载体，可使用水、乙醇、苯，二甲苯，煤油，矿物油，环己烷、环己酮，二甲基甲酰胺或类似物。需要的话，可添加表面活性剂，以使剂型均匀、稳定。
这些化合物也可掺合其它用于农业和园艺管理中，且可与这些化合物相容的化学药品一起使用。
此类化学药品可以（但并不限定这些）是：通常熟知的杀菌剂、杀虫剂、杀螨剂、除草剂和植物生长调节剂等化学药品。特别是，通过将上述化合物与其它除草剂混合，可减少其使用剂量和人力，且可进一步期望由于两种化学药品的协合功能而发挥更高的效应。
为了以已知除草剂掺合此化合物，可介绍应用：杀草丹、草达灭，My-93（S-（2，2-二甲基苯偶酰）1-哌啶硫代羧酸盐）或其它氨基甲酸盐型除草剂;硫代氨基甲酸盐型除草剂，去草胺、pretila-chlor、mefenacet、或其它酸性酰胺类除草剂;chtormethoxynil、治草醚、或其它二苯醚类除草剂;阿特拉津，草净津或其它敌菌灵类除草剂;chlorsulfurnon、sulfometuron-methyl或其它磺酰脲类除草剂;MCP、MCPB或其它苯氧基烷烃羧酸类除草剂;diclo-fopmethyl或其它苯氧基丙酸类除草剂;新燕灵，flamprop-ethyl或其它苯甲酰氨基丙酸类除草剂;另外，piperophos    dymron，噻草平，difenzoquart，naproanilid，HW-52（4-乙氧基甲氧基苯并-2′，3′-二氯酰苯胺），KNW-242（1-（3-甲基苯基）-5-苯基-1H-1，2，4-三唑-3-羧酰胺），quinclorac（3，7-二氯-8-喹啉羧酸），再有，sethoxydim，alloxydim-sodium和其它环己烷二酮类除草剂。这些处于各种混合形式的除草剂也可以与植物油或乳油掺合。
除草剂组合物中活性成分的浓度根据剂型可有变化，例如，在配制可湿性粉剂时，其浓度范围为5-70%（重量），最好是10-30%（重量）;在配制乳油时，其浓度为3-70%（重量），最好为5-20%（重量），在颗粒剂场合，其浓度为0.01-30%（重量），最好为0.05-10%（重量）。
上述所得可湿性粉剂，或乳油，可被水稀释成规定的浓度，并被用作液体悬浮液或液体乳化液来处理土壤或植物叶面。另外，也可直接将颗粒剂施于土壤或与土壤混合。
下述实施例说明了除草剂的组成，但并无限定之意：
实施例3    可湿性粉剂
重量份
本发明的化合物    20
白碳    20
硅藻土    52
烷基硫酸钠    8
均匀混合以上组分，使其成细小颗粒，以提供含20%活性成分的可湿性粉剂。使用时，用水稀释成所需浓度，以悬浮液喷施。
实施例4    乳油
重量份
本发明的化合物    20
二甲苯    55
二甲基甲酰胺    15
聚氧乙烯苯基醚    10
将上述组分混合、溶解，以提供含20%活性成分的乳油。使用时，将其用水稀释成所需浓度，以乳状液喷施。
实施例5    颗粒剂
重量份
本发明的化合物    5
滑石    40
粘土    38
膨润土    10
烷基硫酸钠    7
均匀混合上述组分，以提供含5%活性成分的颗粒剂。
工业上的可应用性：
下述试验说明了此化合物的除草效果。
试验1：芽后处理试验
将Henry蟋蟀草，长狗尾草（giant foxtail），碎米莎草（rice flatsedge），绒毛草（veluet leaf），红根藜（redroot pigweed）和玉米的种子植入含粘壤土的粘土钵（200cm2）中，并使其在温室中生 长。当植株长至5-10cm高，把以水稀释乳油至规定浓度（250ppm）制备的水悬浮液，按100升/10公亩之比率，用一微喷雾器，喷施于植物叶面上。
处理后三周，观测每棵植株受损程度，并以下述定义的0-10标值予以评定：
指数    受损程度
0    0%
2    20-29%
4/    40-49%
6    60-69%
8    80-89%
10    100%
指数1，3，5，7和9分别表示0和2，2和4，4和6，6和8，8和10的中间值。
受损程度（%）＝ (（未处理钵中鲜重）-（处理过钵中鲜重量）)/(未处理钵中鲜重) ×100%
其结果列于表4（表4见文后）
Figure 901034223_IMG10
Figure 901034223_IMG12
Figure 901034223_IMG15
Figure 901034223_IMG16
Figure 901034223_IMG17
Figure 901034223_IMG18
Figure 901034223_IMG19
Figure 901034223_IMG20
Figure 901034223_IMG21
Figure 901034223_IMG23
Figure 901034223_IMG24
Figure 901034223_IMG25
Figure 901034223_IMG26
Figure 901034223_IMG27
Figure 901034223_IMG28
Figure 901034223_IMG29
表3
结构式
Figure 901034223_IMG30
Figure 901034223_IMG31
表4
损坏程度（指数）
化合物    蟋蟀草    长狗尾草    绒毛草    红根藜    碎米莎草    玉米
编号
Ⅰ-10    10    10    10    10    10    3
Ⅰ-20    10    10    10    10    10    0
Ⅰ-21    10    10    10    10    10    0
Ⅰ-35    10    10    10    10    10    0
Ⅰ-36    10    10    10    10    10    0
Ⅰ-48    10    10    10    10    10    0
Ⅰ-49    10    10    10    10    10    0
Ⅰ-50    10    10    10    10    10    0
Ⅰ-54    10    10    10    10    10    0
Ⅰ-55    10    10    10    10    10    0
Ⅰ-56    10    10    10    10    10    0
Ⅰ-57    10    10    10    10    10    0
Ⅰ-65    10    10    10    10    10    0
Ⅰ-81    10    10    10    10    10    0
Ⅰ-85    10    10    10    10    10    1
Ⅰ-97    10    10    10    10    10    2
Ⅰ-98    10    10    10    10    10    2
Ⅰ-99    10    10    10    10    10    0
Ⅰ-100    10    10    10    10    10    0
Ⅰ-101    10    10    10    10    10    3
Ⅰ-109    10    10    10    10    10    0
Ⅰ-133    10    10    10    10    10    0
Ⅰ-143    10    10    10    10    10    0
Ⅰ-144    10    10    10    10    10    1
Ⅰ-145    10    10    10    10    10    0
Ⅰ-146    10    10    10    10    10    0
Ⅰ-168    10    10    10    10    10    0
Ⅰ-169    10    10    10    10    10    0
Ⅰ-170    10    10    10    10    10    2
Ⅰ-172    10    10    10    10    10    0
Ⅰ-173    10    10    10    10    10    2
Ⅰ-176    10    10    10    10    10    0
Ⅰ-177    10    10    10    10    10    0
Ⅰ-178    10    10    10    10    10    0
Ⅰ-179    10    10    10    10    10    3
Ⅰ-180    10    10    10    10    10    2
Ⅰ-181    10    10    10    10    10    3
Ⅰ-183    10    10    10    10    10    3
Ⅰ-184    10    10    10    10    10    3
Ⅰ-185    10    10    10    10    10    0
Ⅰ-186    10    10    10    10    10    0
Ⅰ-187    10    10    10    10    10    2
Ⅰ-188    10    10    10    10    10    3
Ⅰ-189    10    10    10    10    10    0
Ⅰ-190  10    10    10    10    10    2
Ⅰ-191    10    10    10    10    10    0
Ⅰ-192    10    10    10    10    10    0
Ⅰ-193    10    10    10    10    10    0
Ⅰ-195    10    10    10    10    10    0
Ⅰ-196    10    10    10    10    10    0
Ⅰ-197    10    10    10    10    10    3
Ⅰ-198    10    10    10    10    10    0
Ⅰ-200    10    10    10    10    10    0
Ⅰ-201    10    10    10    10    10    0
Ⅰ-202    10    10    10    10    10    0
Ⅰ-203    10    10    10    10    10    0
Ⅰ-204    10    10    10    10    10    1
Ⅰ-205    10    10    10    10    10    1
Ⅰ-207    10    10    10    10    10    2
Ⅰ-208    10    10    10    10    10    0
Ⅰ-209    10    10    10    10    10    0
Ⅰ-210    10    10    10    10    10    2
Ⅰ-211    10    10    10    10    10    0
Ⅰ-212    10    10    10    10    10    2
Ⅰ-214    10    10    10    10    10    0
Ⅰ-215    10    10    10    10    10    3
Ⅰ-216    10    10    10    10    10    0
Ⅰ-217    10    10    10    10    10    0
Ⅰ-218    10    10    10    10    10    0
Ⅰ-219    10    10    10    10    10    0
Ⅰ-220    10    10    10    10    10    0
Ⅰ-222    10    10    10    10    10    0
Ⅰ-224    10    10    10    10    10    3
Ⅰ-225    10    10    10    10    10    3
Ⅰ-228    10    10    10    10    10    0
Ⅰ-229    10    10    10    10    10    0
Ⅰ-230    10    10    10    10    10    0
Ⅰ-231    10    10    10    10    10    0
Ⅰ-232    10    10    10    10    10    0
Ⅰ-233    10    10    10    10    10    0
Ⅰ-234    10    10    10    10    10    0
Ⅰ-237    10    10    10    10    10    3
Ⅰ-238    10    10    10    10    10    0
Ⅰ-240    10    10    10    10    10    0
Ⅰ-241    10    10    10    10    10    0
Ⅰ-244    10    10    10    10    10    2
Ⅰ-245    10    10    10    10    10    2
Ⅰ-249    10    10    10    10    10    3
Ⅰ-250    10    10    10    10    10    0
Ⅰ-251    10    10    10    10    10    0
Ⅰ-254    10    10    10    10    10    0
Ⅱ-102    10    10    10    10    10    3
Ⅱ-109    10    10    10    10    10    0
Ⅱ-130    10    10    10    10    10    0
Ⅱ-137    10    10    10    10    10    0
Ⅱ-277    10    10    10    10    10    3
对照
化合物A    6    7    8    4    5    7
对照
化合物B    6    5    8    2    8    6
对照化合物A
Figure 901034223_IMG32
（DE 3902818）
对照化合物B
Figure 901034223_IMG33
（DE 3902818）

Claims (3)

1、一种除草剂，其特征在于，所述的除草剂由载体及作为其有效成分的0.01-70%(重量)的一种或一种以上的由式(Ⅰ)代表的取代的二环庚二酮化合物或其盐组成：
(Ⅰ)
式中，R1为C1-5的烷基，可被卤素、C1-6烷氧基、C1-4烷基、C1-4卤代烷基、C1-4烷基磺酰基、C1-4烷氧基-C1-4烷基、C1-4烷基硫代-C1-4烷基硫代、C1-4烷基硫代、C1-4烷基硫代、C1-4烷氧基-C1-4烷基硫代、硝基、C1-4烷基羰基氨基、C1-4烷基硫代-C1-4烷氧基、C2-4链烯氧基、C2-4炔氧基C1-4卤代烷氧基、C1-4二烷基氨基磺酰基、C2-4链烯基硫代、C1-4卤代烷基磺酰基、C2-4卤代链烯氧基、C1-4烷基羰基、C1-4烷氧基-C1-4烷基磺酰基、C1-4烷氧基-C1-4烷氧基、羟基、卤代苯氧基、或苄氧基取代的苯基，可被卤素取代的苄基、或可被C1-4烷基、卤素或C1-4烷基磺酰基取代的吡啶基；R2为卤素，C1-4烷氧基，C1-4烷基硫代，C1-4烷基磺酰基，C1-4烷基，C1-4烷氧基烷基或C1-4烷氧基羰基；n为0到4；R3和R4可相同或不同地，为氢或C1-3烷基。
CN90103422A 1989-07-04 1990-07-03 含取代的二环庚二酮衍生物的除草剂 Expired - Fee Related CN1025186C (zh)

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JP89-257157 1989-10-03
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JPH04247052A (ja) * 1991-01-31 1992-09-03 Nippon Soda Co Ltd ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法
WO1993020037A1 (en) * 1992-03-27 1993-10-14 Nippon Soda Co., Ltd. Cyclohexenone compound and production thereof
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BR9509624A (pt) * 1994-11-07 1997-09-16 Nippon Soda Co Derivados de biciclo-heptanodiona substituída e herbicidas
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