CN105949179A - 一类含呋喃的嘧啶联吡唑甲酰胺类衍生物及其制备方法和用途 - Google Patents
一类含呋喃的嘧啶联吡唑甲酰胺类衍生物及其制备方法和用途 Download PDFInfo
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- CN105949179A CN105949179A CN201610522817.4A CN201610522817A CN105949179A CN 105949179 A CN105949179 A CN 105949179A CN 201610522817 A CN201610522817 A CN 201610522817A CN 105949179 A CN105949179 A CN 105949179A
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Abstract
本发明提供了一类含呋喃的嘧啶联吡唑甲酰胺类衍生物及其制备方法和用途，本发明涉及含呋喃的嘧啶联吡唑甲酰胺类衍生物，它们具有如Ⅴ所示的化学结构通式。
Description
技术领域
本发明的技术方案涉及含酰胺键的酰胺类衍生物，具体涉及含呋喃的嘧啶联吡唑甲酰胺类衍生物。
背景技术
农药在防治农作物病虫草害，提高农产品产量和质量方面发挥着重要作用。在过去的几十年，化学农药在农业发展中发挥了一个重要的作用。然而，随着化学农药的长期、连续和大面积使用，农业有害生物的抗性问题越来越严重。另外，化学农药对环境和人类健康产生的影响也越来越引起人类的重视。因此，研究和开发高活性、低使用量、环境友好型农药迫在眉睫。
目前，新农药创制的热点领域是从天然产物中挖掘和获取低残留、高选择性的绿色农药，然后经结构优化后转变为能够成为进入农药市场的产品。以天然产物为先导化合物，经结构修饰、改造后开发合成的新农药在农药市场中占有越来越重要的地位。此外，以靶标生物体生命过程中某个关键的生理生化作用机制为研究模型，人为设计合成干扰此作用机制的化合物，从中筛选出先导化合物，然后进行结构优化，开发新型农药也是新农药创制的一条重要途径。
本课题组前期以转酮醇酶为靶标进行计算机药物虚拟筛选得到了一种活性较好的酰胺类化合物，其可作为新农药研究的先导化合物。本发明以该化合物为先导化合物，利用农药分子设计的原理将不同具有农药活性的基团引入该化合物中，设计合成了一类含酰胺键的酰胺类衍生物，并进行了系统的生物活性筛选，以期为新农药的创制提供更多高效的侯选化合物。
发明内容
本发明所要解决的技术问题是：提供新的含呋喃的嘧啶联吡唑甲酰胺类衍生物的合成方法，提供这类化合物调控农业、园艺和林业杂草及植物病原物的生物活性及其测定方法，同时提供这些化合物在农业领域、园艺领域、林业领域中的应用。
本发明解决该技术问题所采用的技术方案是：具有农业领域、园艺领域、林业领域除草和 杀菌活性的含呋喃的嘧啶联吡唑甲酰胺类衍生物的化学结构通式见式V：
其中，R选自X选自S和O；R2选自H、CF3、F、Cl；R3选自H、CF3、F、Cl；R4选自H、CF3、F、Cl、NO2、OCH3；R5选自H和F；R6选自H和Cl；R7选自H和Cl；R8选自H和CF3；本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的合成方法如下：
其中，R选自X选自S和O；R2选自H、CF3、F、Cl；R3选自H、CF3、F、Cl；R4选自H、CF3、F、Cl、NO2、OCH3；R5选自H和F；
R6选自H和Cl；R7选自H和Cl；R8选自H和CF3；
化合物V的合成方法具体分为以下步骤：
A中间体III的制备：
在100毫升的两口圆底烧瓶中加入2.00克，即14.8毫摩尔的呋喃甲酰乙腈，用20毫升无水乙醇溶解，后加入14.8毫摩尔的中间体I，加热回流反应，TLC监测反应进程，反应完后减压除去溶剂无水乙醇，残余物经200～300目硅胶柱层析纯化得到中间体III，洗脱剂体积比为二氯甲烷/甲醇＝60/1，收率为87％，中间体III制备的量和反应容器的体积按相应比例扩大或缩小；
B中间体IV的制备：
在100毫升两口圆底烧瓶中加入5.00毫摩尔的中间体II，然后向反应中加入10毫升重蒸过的氯化亚砜和2滴DMF，回流反应5h，反应完后，将回流装置改为蒸馏装置，蒸出过量的氯化亚砜；得到中间体IV，中间体IV不需纯化，直接进行下步反应，收率90-100％；中间体IV制备的量和反应容器的体积按相应比例扩大或缩小；
C含呋喃的嘧啶联吡唑甲酰胺类衍生物V的制备：
在100毫升的两口圆底烧瓶中加入1.78毫摩尔的中间体III，用20毫升重蒸过的二氯甲烷溶解，然后加入0.22克，即2.13毫摩尔的三乙胺，冰盐浴下搅拌，待温度降至0摄氏度以下时，滴加2.13毫摩尔的中间体IV和10毫升重蒸过的二氯甲烷的混合溶液，滴毕，恢复至常温反应，TLC监测反应进程，反应完后先用30毫升3.6％的盐酸水溶液洗三次，以除去未反应完全的中间体III，然后有机层依次用30毫升饱和碳酸氢钠溶液、30毫升饱和氯化钠溶液各洗一次，以除去反应液中的水分，最后有机层用无水硫酸钠干燥过夜，减压除去溶剂二氯甲烷后，残余物经200～300目硅胶柱层析纯化得到化合物V，用所得纯品计算收率，收率42.81-90.35％；化合物V制备的量和反应容器的体积按相应比例扩大或缩小，化合物V的化学结构和理化参数见表1；
D本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的除草活性测定：
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的除草活性采用茎叶处理法，具体步骤为：取50毫克样品溶解在适量二甲基甲酰胺内，然后用含有一定量吐温20乳化剂水溶 液稀释至1000微克/毫升的药剂；待双子叶杂草生长至两叶期，单子叶杂草生长至3～5叶期时，将供试药剂采用定量喷雾装置均匀喷洒在杂草叶片上，以不添加样品的溶液做空白对照，每处理重复3次，将处理后的杂草放在人工气候培养箱内培养，24h后用目测法调查样品对杂草生长的抑制程度，供试植物为我国农业生产中田间实际发生的大部分典型杂草的种属以及模式植物拟南芥，其名称如下：马唐，其拉丁名为：Digitaria sanguinalis L.、狗尾草，其拉丁名为：Setaria viridis L.、反枝苋，其拉丁名为：Amaranthus retroflexus L.、马齿苋，其拉丁名为：Portulaca oleracea L.、拟南芥，其拉丁名为：Arabidopsis thaliana、稗草，其拉丁名为：Echinochloa crus-galli L.
E本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的杀菌活性测定：
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的杀菌或抑菌活性采用菌体生长率测定法，具体步骤为：取2.0毫克样品溶解在适量二甲基甲酰胺内，然后用无菌水稀释至500微克/毫升的药剂，将供试药剂在无菌条件下各吸取1毫升注入培养皿内，再分别加入9毫升PDA培养基，摇匀后制成50微克/毫升含药平板，以添加1毫升灭菌水的平板做空白对照，用直径4毫米的打孔器沿菌丝外缘切取菌盘，移至含药平板上，呈等边三角形摆放，每处理重复3次，将培养皿放在24±1摄氏度恒温培养箱内培养，待对照菌落直径扩展到2-3厘米后调查各处理菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率，供试菌种为我国农业生产中田间实际发生的大部分典型植物病原菌的种属，其代号和名称如下：AS：番茄早疫病菌，其拉丁名为：Alternaria solani、BC：黄瓜灰霉病菌，其拉丁名为：Botrytis cinerea、CA：花生褐斑病菌，其拉丁名为：Cercospora arachidicola、GZ：小麦赤霉病菌，其拉丁名为：Gibberella zeae、PI：马铃薯晚疫病菌，其拉丁名为：Phytophthorainfestans(Mont.)de Bary、PP：苹果轮纹病菌，其拉丁名为：Physalospora piricola、PS：水稻纹枯病菌，其拉丁名为：Pellicularia sasakii、RC：禾谷丝核菌，其拉丁名为：Rhizoctoniacerealis、SS：油菜菌核病菌，其拉丁名为：Sclerotinia sclerotiorum；
本发明的有益效果是：对含呋喃的嘧啶联吡唑甲酰胺类衍生物V进行了衍生合成，并对合成的新化合物进行了除草和杀菌活性的筛选。
本发明通过特定制备和生物活性测定实施例更加具体说明含呋喃的嘧啶联吡唑甲酰胺类衍生物V的合成与生物活性及应用，所述实施例仅用于具体说明本发明而非限制本 发明，尤其是生物活性仅是举例说明，而非限制本专利，具体实施方式如下：
实施例1
中间体III的制备：
在100毫升的两口圆底烧瓶中加入2.00克，即14.8毫摩尔的呋喃甲酰乙腈，用20毫升无水乙醇溶解，后加入1.63克，即14.8毫摩尔的2-肼基嘧啶，加热回流反应，TLC监测反应进程，反应完后减压除去溶剂无水乙醇，残余物经200～300目硅胶柱层析纯化得到中间体III，洗脱剂体积比为二氯甲烷/甲醇＝60/1；用所得纯品计算收率收率87％。1H NMR(400MHz，CDCl3)δ 8.78(d，J＝4.8Hz，2H)，7.49(d，J＝1.0Hz，1H)，7.16(t，J＝4.8Hz，1H)，6.93(d，J＝3.4Hz，1H)，6.49(dd，J＝3.3，1.8Hz，1H)，5.98(s，2H)，5.86(s，1H).
实施例2
中间体IV的制备：
在100毫升两口圆底烧瓶中加入5.00毫摩尔的中间体II，然后向反应中加入10毫升重蒸过的氯化亚砜和2滴DMF，回流反应5h，反应完后，将回流装置改为蒸馏装置，蒸出过量的氯化亚砜。得到中间体IV，中间体IV不需纯化，直接进行下步反应。收率90-100％。
实施例3
含呋喃的嘧啶联吡唑甲酰胺类衍生物V的制备：
在100毫升的两口圆底烧瓶中加入1.78毫摩尔的中间体III，用20毫升重蒸过的二氯甲烷溶解，然后加入0.22克，即2.13毫摩尔的三乙胺，冰盐浴下搅拌，待温度降至0摄氏度以下时，滴加2.13毫摩尔的中间体IV和10毫升重蒸过的二氯甲烷的混合溶液，滴毕，恢复至常温反应。TLC监测反应进程，反应完后先用30毫升3.6％的盐酸水溶液洗三次，以除去未反应完全的中间体III，然后有机层依次用30毫升饱和碳酸氢钠溶液、30毫升饱和氯化钠溶液各洗一次，以除去反应液中的水分，最后有机层用无水硫酸钠干燥过夜。减压除去溶剂二氯甲烷后，残余物经200～300目硅胶柱层析纯化得到化合物V，用所得纯品计算收率，收率42.81-90.35％。
实施例4
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V除草活性测定结果：
本发明测试的常见杂草和模式植物名称如下：马唐，其拉丁名为：Digitaria sanguinalisL.、狗尾草，其拉丁名为：Setaria viridis L.、反枝苋，其拉丁名为：Amaranthus retroflexus
L.、马齿苋，其拉丁名为：Portulaca oleracea L.、稗草，其拉丁名为：Echinochloa crusgalliL.模式植物拟南芥，其拉丁名为：Arabidopsis thaliana。这些杂草种类具有很好的代表性，能够代表农业生产中田间发生的大部分杂草。除草生物活性测定结果见表2，表2表明，在1000微克/毫升时，本发明合成的所有化合物均有不同程度的除草活性。对马唐而言，化合物HUO-XA-a、HUO-XA-9、HUO-XA-17、HUO-XA-19、HUO-XA-21、HUO-XA-55的抑制等级达到3级以上。其中，化合物HUO-XA-17、HUO-XA-19、HUO-XA-21、HUO-XA-55的抑制等级高出中间体HUO-XA-a 1个等级。对狗尾草而言，化合物HUO-XA-9、HUO-XA-14、HUO-XA-17、HUO-XA-19、HUO-XA-21、HUO-XA-55的抑制等级达到3级，高出中间体HUO-XA-a 2个等级，其余衍生物抑制等级与中间体HUO-XA-a相同或高出1个等级。对稗草而言，化合物HUO-XA-14、HUO-XA-17、HUO-XA-19、HUO-XA-21、HUO-XA-55的抑制等级达到3级，高出中间体HUO-XA-a 2个等级。对反枝苋而言，化合物HUO-XA-5、HUO-XA-19、HUO-XA-25、HUO-XA-40、HUO-XA-43、HUO-XA-52、HUO-XA-55、HUO-XA-58、HUO-XA-66的抑制等级达到3级以上。其中，化合物HUO-XA-19的抑制等级达到5级，高出中间体HUO-XA-a 3个等级。对马齿苋而言，化合物HUO-XA-5、HUO-XA-19、HUO-XA-55、HUO-XA-56、HUO-XA-58、HUO-XA-66的抑制等级达到3级以上，这些化合物的抑制等级高出中间体HUO-XA-a 2个或3个等级。对拟南芥而言，化合物HUO-XA-5、HUO-XA-19、HUO-XA-25、HUO-XA-40、HUO-XA-48、HUO-XA-55、HUO-XA-63、HUO-XA-69的抑制等级达到3级以上，其中，化合物HUO-XA-5、HUO-XA-19的抑制等级达到5级，高出中间体HUO-XA-a 4个等级。因此，本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物由于不同除草活性基团的引入使其具有不同程度的除草活性。
实施例5
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V抑菌活性测定结果：
本发明测试的常见植物病原真菌的代号和名称如下：AS：番茄早疫病菌，其拉丁名为：Alternaria solani、BC：黄瓜灰霉病菌，其拉丁名为：Botrytis cinerea、CA：花生褐斑病菌，其拉丁名为：Cercospora arachidicola、GZ：小麦赤霉病菌，其拉丁名为：Gibberellazeae、PI：马铃薯晚疫病菌，其拉丁名为：Phytophthora infestans(Mont.)de Bary、PP：苹 果轮纹病菌，其拉丁名为：Physalospora piricola、PS：水稻纹枯病菌，其拉丁名为：Pellicularia sasakii、RC：禾谷丝核菌，其拉丁名为：Rhizoctonia cerealis、SS：油菜菌核病菌，其拉丁名为：Sclerotinia sclerotiorum，这些菌种具有很好的代表性，能够代表农业生产中田间发生的大部分病原菌的种属。菌体生长率法测定结果见表3，表3表明，在50微克/毫升时，本发明合成的所有化合物均有不同程度的杀菌活性。对马铃薯晚疫病菌而言，化合物HUO-XA-7的抑制率在55％以上，杀菌活性高出对照药剂嘧菌酯在10％以上，高出中间体HUO-XA-a在40％以上。对花生褐斑病菌而言，化合物HUO-XA-43、HUO-XA-54的抑制率在40％以上，杀菌活性高出中间体HUO-XA-a在10％左右。对番茄早疫菌而言，化合物HUO-XA-7、HUO-XA-9、HUO-XA-48、HUO-XA-54、HUO-XA-55、HUO-XA-58、HUO-XA-63、HUO-XA-66、HUO-XA-69的抑制率在40％以上。其中化合物HUO-XA-66的抑制率在60％以上，杀菌活性高出中间体HUO-XA-a在30％左右。对黄瓜灰霉病菌而言，化合物HUO-XA-a、HUO-XA-7、HUO-XA-9、HUO-XA-11、HUO-XA-17、HUO-XA-43、HUO-XA-48、HUO-XA-52、HUO-XA-66的抑制率在40％以上。其中中间体HUO-XA-a的抑制率达75％，所有衍生物的活性均低于该中间体。对小麦赤霉病菌而言，化合物HUO-XA-9、HUO-XA-29、HUO-XA-43、HUO-XA-52、HUO-XA-56、HUO-XA-58、HUO-XA-66的抑制率在40％以上。其中，化合物HUO-XA-66的抑制率达68％，杀菌活性高出中间体HUO-XA-a在30％以上。对苹果轮纹病菌而言，化合物HUO-XA-a、HUO-XA-7、HUO-XA-29的抑制率在50％以上。其中，化合物HUO-XA-a的抑制率达63.04％，所有衍生物的活性均低于该中间体。对油菜菌核病菌而言，所有化合物的抑制率在40％以上，其中化合物HUO-XA-9、HUO-XA-11、HUO-XA-19、HUO-XA-21的抑制率高于85％，杀菌活性高出中间体HUO-XA-a在30％以上。对禾谷丝核菌而言，化合物HUO-XA-7、HUO-XA-43、HUO-XA-52的抑制率在30％以上，杀菌活性高出中间体HUO-XA-a在20％以上。对水稻纹枯病菌而言，化合物HUO-XA-5、、HUO-XA-7、HUO-XA-9、HUO-XA-21、HUO-XA-29的抑制率在40％以上，杀菌活性高出中间体HUO-XA-a在20％左右。因此，本发明设计合成的新化合物由于引入取代基的不同，目标化合物均有不同的杀菌活性。
实施例6
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与农业上可接受的助剂以及如下的商品除草剂中的任意一种或多种组合在制备复配除草剂中的用途：
所述商品除草剂选自烟嘧磺隆、苯磺隆、单醚磺隆、甲嘧磺隆、五氟磺草胺、甲草胺、乙草胺、丁草胺、异丙甲草胺、2甲4氯、氟乐灵、硝磺草酮、甲基磺草酮、苯唑草酮、二甲戊乐灵、莠去津、扑草净、氰草津、莠灭净、嗪草酮、除草醚、乙氧氟草醚、三氟羧草醚、乳氟禾草灵、乙羧氟草醚、吡草醚、异丙吡草酯、咪唑烟酸、咪唑乙烟酸、咪草酸、咪唑喹啉酸、甲氧咪草烟、甲基咪草烟、嘧硫草醚、嘧草醚、双草醚、嘧啶肟草醚、环酯草醚、甜菜宁、甜菜安、燕麦灵、双胺灵、稗草畏、禾草畏、苄草丹、吡氟禾草灵、吡氟氯禾灵、恶唑禾草灵、喹禾灵、噻唑禾草灵、氟草烟、氟硫草定、氟啶酮、噻草啶、氟吡草腙、百草枯、草甘磷、莎草稗、氟烯草酸、丙炔氟草胺、氟噻甲草酯、嗪草酸甲酯、吡唑特、吡草酮、苄草唑、异恶唑草酮、异恶氯草酮、溴苯腈等；本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V在所得复配除草剂中的总的质量百分含量是1％-90％，本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与所述商品除草剂的比例为质量百分比1％∶99％到99％∶1％；所述复配除草剂适用的剂型选自下列剂型中的任意一种：可湿性粉剂、微胶囊悬浮剂、可分散液体制剂、可分散固体制剂、种子处理乳剂、水乳剂、大粒剂、微乳剂、油悬浮剂、水溶性粒剂、可溶性浓剂、水分散性粒剂、毒谷、气雾剂、缓释块、胶囊粒剂、干拌种粉剂、乳油、静电喷雾剂、油包水乳剂、水包油乳剂、烟雾罐、细粒剂、烟雾烛、烟雾筒、烟雾棒、种子处理悬浮剂、烟雾片、烟雾丸、发气剂、漂流粉剂、油膏、热雾剂、固/液混合装剂、液/液混合装剂、冷雾剂、固/固混合装剂、药漆、种子处理液剂、微粒剂、油分散性粉剂、浓胶剂、泼浇剂、涂抹剂、悬浮乳剂、成膜油剂、可溶性粉剂、种子处理水溶性粉剂、超低容量悬浮剂、追踪粉剂、超低容量液剂、蒸汽释放剂、湿拌种水分散性粉剂；所述复配除草剂适用的植物选自稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔、桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景；所述复配除草剂适用的防治杂草选自：禾本科杂草：马唐、狗尾草、牛筋草、稗、千 金子、虎尾草、野燕麦、画眉草、金色狗尾草、长芒棒头草、看麦娘等；阔叶杂草：反枝苋、马齿苋、藜、播娘蒿、铁苋菜、苍耳、豚草、苋属、苘麻、地肤、龙葵、柳叶刺蓼、繁缕、香薷、水棘针、酸模叶蓼、打碗花、田旋花、菟丝子等；莎草科杂草：牛毛毡、异性莎草、水莎草、猪毛菜、水葱等。
实施例7
本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与农业上可接受的助剂以及如下的商品杀菌剂中的任意一种或多种组合在制备复配杀菌剂中的用途：
所述商品杀菌剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1，2，3-噻二唑-5-甲酸、4-甲基-1，2，3-噻二唑-5-甲酸钠、4-甲基-1，2，3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺，其英文通用名为：isotianil、3，4-二氯异噻唑-5-甲酸、3，4-二氯异噻唑-5-甲酸钠、3，4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基 硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑；本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V在所述杀菌组合物中的总的质量百分含量是1％-90％，本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与前述商品杀菌剂的比例为质量百分比1％∶99％到99％∶1％；所述杀菌组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述杀菌组合物防治的植物病害选自：稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病；所述杀菌组合物适用的植物选自：稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
表1本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的化学结构和理化参数
表2本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物的除草活性(1000微克/毫升的抑制等级)
| 序号 | 化合物 | 马唐 | 狗尾草 | 稗草 | 反枝苋 | 马齿苋 | 拟南芥 |
| 1 | HUO-XA-a | 3 | 1 | 1 | 2 | 1 | 1 |
| 2 | HUO-XA-2 | 1 | 1 | 1 | 2 | 1 | 1 |
| 3 | HUO-XA-5 | 2 | 2 | 1 | 4 | 3 | 5 |
| 4 | HUO-XA-7 | 2 | 2 | 1 | 1 | 1 | 1 |
| 5 | HUO-XA-9 | 3 | 3 | 2 | 1 | 1 | 1 |
| 6 | HUO-XA-11 | 0 | 1 | 0 | 1 | 1 | 0 |
| 7 | HUO-XA-14 | 4 | 3 | 3 | 1 | 1 | 0 |
| 8 | HUO-XA-17 | 4 | 3 | 3 | 1 | 1 | 1 |
| 9 | HUO-XA-19 | 4 | 3 | 3 | 5 | 4 | 5 |
| 10 | HUO-XA-21 | 4 | 3 | 3 | 1 | 1 | 1 |
| 11 | HUO-XA-23 | 1 | 1 | 1 | 1 | 1 | 1 |
| 12 | HUO-XA-25 | 1 | 1 | 1 | 3 | 2 | 3 |
| 13 | HUO-XA-27 | 1 | 1 | 2 | 1 | 2 | 2 |
| 14 | HUO-XA-29 | 2 | 2 | 2 | 1 | 2 | 1 |
| 15 | HUO-XA-40 | 1 | 1 | 1 | 3 | 2 | 3 |
| 16 | HUO-XA-43 | 1 | 1 | 1 | 3 | 2 | 2 |
| 17 | HUO-XA-48 | 2 | 1 | 1 | 2 | 2 | 3 |
| 18 | HUO-XA-52 | 2 | 2 | 2 | 3 | 1 | 2 |
| 19 | HUO-XA-54 | 1 | 1 | 1 | 2 | 2 | 2 |
| 20 | HUO-XA-55 | 4 | 3 | 3 | 4 | 4 | 4 |
| 21 | HUO-XA-56 | 2 | 1 | 1 | 2 | 3 | 2 |
| 22 | HUO-XA-58 | 2 | 1 | 2 | 3 | 3 | 2 |
| 23 | HUO-XA-63 | 2 | 2 | 1 | 2 | 2 | 3 |
| 24 | HUO-XA-66 | 1 | 1 | 1 | 3 | 3 | 2 |
| 25 | HUO-XA-69 | 2 | 1 | 2 | 2 | 2 | 3 |
注：0级，生长抑制率同对照；1级，生长抑制率＜25％；2级，生长抑制率在25％～50％之间；3级，生长抑制率在50％～75％之间；4级，生长抑制率75％～95％之间；5级，生长抑制率＞95％。
表3本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物的抑菌活性(50微克/毫升的抑制率/％)
| 序号 | 化合物 | PI | CA | AS | BC | GZ | PP | SS | RC | PS |
| 1 | HUO-XA-a | 15.15 | 31.58 | 33.33 | 75.00 | 35.90 | 63.04 | 54.55 | 8.00 | 22.22 |
| 2 | HUO-XA-2 | 7.69 | 35.29 | 28.57 | 21.43 | 16.13 | 16.67 | 85.00 | 0 | 36.00 |
| 3 | HUO-XA-5 | 11.54 | 23.53 | 33.33 | 35.71 | 22.58 | 16.67 | 73.33 | 7.41 | 40.00 |
| 4 | HUO-XA-7 | 57.69 | 35.29 | 42.86 | 64.29 | 32.26 | 58.33 | 63.33 | 33.33 | 58.00 |
| 5 | HUO-XA-9 | 15.38 | 32.35 | 45.24 | 64.29 | 56.45 | 0 | 86.67 | 14.81 | 48.00 |
| 6 | HUO-XA-11 | 19.23 | 23.53 | 23.81 | 50.00 | 25.81 | 0 | 86.67 | 7.41 | 0 |
| 7 | HUO-XA-14 | 15.38 | 5.88 | 19.05 | 0 | 16.13 | 0 | 83.33 | 7.41 | 28.00 |
| 8 | HUO-XA-17 | 11.54 | 23.53 | 19.05 | 57.14 | 22.58 | 0 | 85.00 | 7.41 | 0 |
| 9 | HUO-XA-19 | 11.54 | 5.88 | 23.81 | 35.71 | 22.58 | 16.67 | 86.67 | 7.41 | 30.00 |
| 10 | HUO-XA-21 | 0 | 17.65 | 19.05 | 21.43 | 12.90 | 4.17 | 86.67 | 3.70 | 40.00 |
| 11 | HUO-XA-23 | 15.38 | 11.76 | 14.29 | 35.71 | 19.35 | 25.00 | 83.33 | 0 | 0 |
| 12 | HUO-XA-25 | 23.08 | 35.29 | 38.10 | 39.29 | 35.48 | 0 | 83.33 | 0 | 30.00 |
| 13 | HUO-XA-27 | 11.54 | 0 | 28.57 | 21.43 | 3.23 | 8.33 | 83.33 | 7.41 | 20.00 |
| 14 | HUO-XA-29 | 19.23 | 23.53 | 33.33 | 35.71 | 51.61 | 50.00 | 81.67 | 7.41 | 48.00 |
| 15 | HUO-XA-40 | 25.93 | 20.00 | 19.23 | 37.50 | 36.00 | 0 | 65.22 | 11.54 | 17.24 |
| 16 | HUO-XA-43 | 22.22 | 40.00 | 38.46 | 41.67 | 40.00 | 12.00 | 56.52 | 30.77 | 27.59 |
| 17 | HUO-XA-48 | 22.22 | 26.67 | 46.15 | 50.00 | 20.00 | 8.00 | 58.70 | 15.38 | 17.24 |
| 18 | HUO-XA-52 | 18.52 | 20.00 | 23.08 | 54.17 | 52.00 | 0 | 45.65 | 30.77 | 10.34 |
| 19 | HUO-XA-54 | 25.93 | 46.67 | 58.33 | 38.46 | 28.00 | 0 | 71.74 | 19.23 | 27.59 |
| 20 | HUO-XA-55 | 18.52 | 13.33 | 54.17 | 19.23 | 24.00 | 0 | 71.74 | 11.54 | 20.69 |
| 21 | HUO-XA-56 | 18.52 | 26.67 | 33.33 | 34.62 | 48.00 | 0 | 84.78 | 19.23 | 20.69 |
| 22 | HUO-XA-58 | 11.11 | 20.00 | 41.67 | 30.77 | 40.00 | 24.00 | 63.04 | 15.38 | 6.90 |
| 23 | HUO-XA-63 | 14.81 | 26.67 | 45.83 | 26.92 | 36.00 | 12.00 | 63.04 | 11.54 | 24.14 |
| 24 | HUO-XA-66 | 33.33 | 33.33 | 62.50 | 42.31 | 68.00 | 0 | 71.74 | 19.23 | 10.34 |
| 25 | HUO-XA-69 | 18.52 | 20.00 | 50.00 | 30.77 | 36.00 | 20.00 | 73.91 | 11.54 | 24.14 |
| 26 | 嘧菌酯 | 46.88 | 55.56 | 75.00 | 91.18 | 71.43 | 100 | 88.10 | 84.06 | 80.77 |
Claims (6)
1.一类含呋喃的嘧啶联吡唑甲酰胺类衍生物，其特征在于具有如式V所示的化学结构通式：
其中，R选自X选自S和O、R2选自H、CF3、F、Cl；R3选自H、CF3、F、Cl；R4选自H、CF3、F、Cl、NO2、OCH3；R5选自H和F、R6选自H和Cl；R7选自H和Cl、R8选自H和CF3；
2.权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V的合成方法，具体合成路线如下：
其中，R选自X选自S和O；R2选自H、CF3、F、Cl；R3 选自H、CF3、F、Cl；R4选自H、CF3、F、Cl、NO2、OCH3；R5选自H和F、R6选自H和Cl；R7选自H和Cl、R8选自H和CF3、
权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物的合成方法分为以下步骤：
A中间体III的制备：
在100毫升的两口圆底烧瓶中加入2.00克，即14.8毫摩尔的呋喃甲酰乙腈，用20毫升无水乙醇溶解，后加入14.8毫摩尔的中间体I，加热回流反应，TLC监测反应进程，反应完后减压除去溶剂无水乙醇，残余物经200～300目硅胶柱层析纯化得到中间体III，洗脱剂体积比为二氯甲烷/甲醇＝60/1，收率为87％；中间体III制备的量和反应容器的体积按相应比例扩大或缩小；
B中间体IV的制备：
在100毫升两口圆底烧瓶中加入5.00毫摩尔的中间体II，然后向反应中加入10毫升重蒸过的氯化亚砜和2滴DMF，回流反应5h，反应完后，将回流装置改为蒸馏装置，蒸出过量的氯化亚砜，得到中间体IV，中间体IV不需纯化，直接进行下步反应，收率90-100％，中间体IV制备的量和反应容器的体积按相应比例扩大或缩小；
C含呋喃的嘧啶联吡唑甲酰胺类衍生物V的制备：
在100毫升的两口圆底烧瓶中加入1.78毫摩尔的中间体III，用20毫升重蒸过的二氯甲烷溶解，然后加入0.22克，即2.13毫摩尔的三乙胺，冰盐浴下搅拌，待温度降至0摄氏度以下时，滴加2.13毫摩尔的中间体IV和10毫升重蒸过的二氯甲烷的混合溶液，滴毕，恢复至常温反应，TLC监测反应进程，反应完后先用30毫升3.6％的盐酸水溶液洗三次，以除去未反应完全的中间体III，然后有机层依次用30毫升饱和碳酸氢钠溶液、30毫升饱和氯化钠溶液各洗一次，以除去反应液中的水分，最后有机层用无水硫酸钠干燥过夜；减压除去溶剂二氯甲烷后，残余物经200～300目硅胶柱层析纯化得到化合物V，用所得纯品计算收率，收率42.81-90.35％，化合物V制备的量和反应容器的体积按相应比例扩大或 缩小。
3.权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与农业上可接受的助剂在制备除草剂中的用途。
4.权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与农业上可接受的助剂在制备杀菌剂中的用途。
5.权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与除草剂组合在防治农业和林业以及园艺杂草中的用途：
权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与商品除草剂中的任意一种或两种组合形成除草组合物用于防治农业和林业以及园艺杂草，所述商品除草剂选自烟嘧磺隆、苯磺隆、单醚磺隆、甲嘧磺隆、五氟磺草胺、甲草胺、乙草胺、丁草胺、异丙甲草胺、2甲4氯、氟乐灵、硝磺草酮、甲基磺草酮、苯唑草酮、二甲戊乐灵、莠去津、扑草净、氰草津、莠灭净、嗪草酮、除草醚、乙氧氟草醚、三氟羧草醚、乳氟禾草灵、乙羧氟草醚、吡草醚、异丙吡草酯、咪唑烟酸、咪唑乙烟酸、咪草酸、咪唑喹啉酸、甲氧咪草烟、甲基咪草烟、嘧硫草醚、嘧草醚、双草醚、嘧啶肟草醚、环酯草醚、甜菜宁、甜菜安、燕麦灵、双胺灵、稗草畏、禾草畏、苄草丹、吡氟禾草灵、吡氟氯禾灵、恶唑禾草灵、喹禾灵、噻唑禾草灵、氟草烟、氟硫草定、氟啶酮、噻草啶、氟吡草腙、百草枯、草甘磷、莎草稗、氟烯草酸、丙炔氟草胺、氟噻甲草酯、嗪草酸甲酯、吡唑特、吡草酮、苄草唑、异恶唑草酮、异恶氯草酮、溴苯腈等；本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V在所得复配除草剂中的总的质量百分含量是1％-90％，本发明的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与所述商品除草剂的比例为质量百分比1％∶99％到99％∶1％；所述复配除草剂适用的剂型选自下列剂型中的任意一种：可湿性粉剂、微胶囊悬浮剂、可分散液体制剂、可分散固体制剂、种子处理乳剂、水乳剂、大粒剂、微乳剂、油悬浮剂、水溶性粒剂、可溶性浓剂、水分散性粒剂、毒谷、气雾剂、缓释块、胶囊粒剂、干拌种粉剂、乳油、静电喷雾剂、油包水乳剂、水包油乳剂、烟雾罐、细粒剂、烟雾烛、烟雾筒、烟雾棒、种子处理悬浮剂、烟雾片、烟雾丸、发气剂、漂流粉剂、油膏、热雾剂、固/液混合装剂、液/液混合装剂、冷雾剂、固/固混合装剂、药漆、种子处理液剂、微粒剂、油分散性粉剂、浓胶剂、泼浇剂、涂抹剂、悬浮乳剂、成膜油剂、可溶性粉剂、种子处理水溶性粉剂、超低容量悬 浮剂、追踪粉剂、超低容量液剂、蒸汽释放剂、湿拌种水分散性粉剂；所述复配除草剂适用的植物选自稻谷、小麦、大麦、燕麦、玉米、高梁、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔、桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景；所述复配除草剂适用的防治杂草选自：禾本科杂草：马唐、狗尾草、牛筋草、稗、千金子、虎尾草、野燕麦、画眉草、金色狗尾草、长芒棒头草、看麦娘等；阔叶杂草：反枝苋、马齿苋、藜、播娘蒿、铁苋菜、苍耳、豚草、苋属、苘麻、地肤、龙葵、柳叶刺蓼、繁缕、香薷、水棘针、酸模叶蓼、打碗花、田旋花、菟丝子等；莎草科杂草：牛毛毡、异性莎草、水莎草、猪毛菜、水葱等。
6.权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与杀菌剂组合在防治农业和林业以及园艺植物病害中的用途：
权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害，所述商品杀菌剂选自：苯并噻二唑、噻酰菌胺，简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1，2，3-噻二唑-5-甲酸、4-甲基-1，2，3-噻二唑-5-甲酸钠、4-甲基-1，2，3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺，其英文通用名为：isotianil、3，4-二氯异噻唑-5-甲酸、3，4-二氯异噻唑-5-甲酸钠、3，4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联 苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑；权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V在所述杀菌组合物中的总的质量百分含量是1％-90％，权利要求1所述的含呋喃的嘧啶联吡唑甲酰胺类衍生物V与前述商品杀菌剂的比例为质量百分比1％∶99％到99％∶1％；所述杀菌组合物加工的剂型选自：种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂；所述杀菌组合物防治的植物病害选自：稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病；所述杀菌组合物适用的植物选自：稻谷、小麦、大麦、燕麦、玉米、高梁、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜 菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
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Application publication date: 20160921 |