CN105506002B - 一种化合物及其应用 - Google Patents
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Abstract
本发明涉及一种化合物及其应用，属微生物生物农药技术领域。本发明的化合物用保藏号：CGMCC No.6351的ZKB4‑4菌株，经试管斜面种子培养、液体培养、发酵罐大量培养、及层析分离的制备步骤得到。所述的化合物3甲氧基环丁烷1,2‑二酮在制备毒杀根结线虫制剂中的应用。所述的化合物3甲氧基环丁烷1,2‑二酮0.5mg溶于甲醇，再用Tween‑20水溶液稀释得到甲醇的终浓度不超过5％、Tween‑20的终浓度不超过0.3％的乳浊液，该乳浊液在制备毒杀根结线虫制剂中的应用。本发明与现有的杀植物寄生线虫药相比，具有高效、低毒及低残留的优点。
Description
技术领域：
本发明涉及一种化合物及其应用，属微生物生物农药技术领域。
背景技术：
植物根结线虫危害严重，它不仅给人类和动物带来严重的疾病，而且每年给农作物造成相当于1044亿美元的损失。目前对线虫的防治仍然以化学防治为主，但由于化学杀线虫剂多数是高毒、高残留农药，对人蓄和环境造成严重的威胁。有的化学杀线虫剂，如用作土壤熏蒸剂的溴甲烷类等，已经在全球多数国家禁止使用或已经规定使用的最后期限。随着人们环境意识的增强，化学杀线剂的应用受到限制，因此对根结线虫的生防研究自然成为重点和焦点问题。在线虫的生防研究中，目前已有直接利用菌体的第一代商品生防剂问世，并已有相当范围的大田应用。由于这一代产品是活菌体，土壤存在着不同程度的抑菌作用，导致在不同国家不同土壤中试用的不稳定性和不一致。这是活体生防制剂的共同通病，为克服这一难题，人们更加关注线虫生防第二代产品的开发，即菌株次生代谢产物的研究与开发。
近30年的研究中，已从50多株菌中分离到90多种对根结线虫有活性的化合物，其结构类型多样，主要有醌类、生物碱类、萜类、肽类、吡喃类、脂肪酸类和萘类等。但由于各种原因，在这些化合物中目前具有潜力开发成线虫生防制剂的很少，因此加紧筛选获得对线虫有活性的物质或组分，将其开发成生防制剂是一项具有重要意义。
国内外文献检索表明，3甲氧基环丁烷1,2-二酮用作有机合成的前体，但未见有关活性和天然来源的报道，用于制备杀线虫制剂应用的公开文献报道。
发明内容：
本发明的目的是提供一种化合物及其应用。
本发明是这样实现的：
本发明使用的细菌是假黄色单胞菌(Pseudoxanthomonas sp.ZKB4-4)。ZKB4-4菌株已于2012年7月12日保藏在中国微生物菌种保藏管理委员会普通微生物中心；保藏单位地址：北京市朝阳区北辰西路1号院3号中国科学院微生物研究所；保藏号为CGMCCNo.6351。
假黄色单胞菌为直或稍弯的革兰氏阴性杆菌。大小(0.5～1)×(1.5～4)微米。以极生鞭毛运动，不形成芽孢、孢囊、鞘或突柄。化能有机营养，除单碳有机物外，能以多种有机物为碳源和能源；利用有机氮或无机氮为氮源，但不能固定分子氮；严格好氧，呼吸代谢，从不发酵，有的种在硝酸盐存在时可行厌氧呼吸；生长温度40～43℃；接触酶阳性，氧化酶通常阳性；DNA中的G+C克分子含量为58～71％。
本发明将假黄色单胞菌ZKB4-4通过常规发酵培养，将发酵液低压浓缩后，用甲醇提取。将甲醇提取物经反复硅胶柱，过凝胶,丙酮/水洗脱。再经自然风干过硅胶柱，乙酸乙酯/甲醇梯度洗脱，得到本发明的化合物，化合物经核磁共振波谱，质谱，红外光谱和紫外光谱确定为3甲氧基环丁烷1,2-二酮，结构式为：
实验表明：3甲氧基环丁烷1,2-二酮具有显著的毒杀南方根结线虫的活性，对南方根结线虫的半致死率浓度为0.447mg/ml。
本发明的从假黄色单胞菌ZKB4-4中用现有方法分离得到的3甲氧基环丁烷1,2-二酮在制备杀线虫制剂中的应用。
用本发明的化合物3甲氧基环丁烷1,2-二酮0.5mg溶于甲醇，再用Tween-20水溶液稀释得到甲醇的终浓度不超过5％、Tween-20的终浓度不超过0.3％的乳浊液，该乳浊液在制备毒杀根结线虫制剂中的应用。
本发明与现有的杀植物寄生线虫药相比，具有高效、低毒及低残留的优点。
具体实施方式：
本发明化合物的发酵生产方法：
1、将ZKB4-4菌株接种到试管固体培养基斜面上，培养基配方为NB培养基，35-37℃下培养1-2天，获得试管种。
2、将NB培养基分装到500ml三角瓶中，常规灭菌，再于超净工作台上用接种针从试管斜面上挑取一些菌体接种于其中，然后32-38℃，180-210rpm/min于摇床上培养1-2天备用。
3、用常规方法将含菌体的发酵液将发酵液低压浓缩后，用甲醇反复溶解，把溶解物合并低压浓缩后得甲醇提取物。用甲醇溶解提取物上样，经正相硅胶柱层析，氯仿反复洗脱。活性跟踪检测所分离到的组分，将具有活性的部分合并低压浓缩，过凝胶,丙酮/水洗脱。再经自然风干过硅胶柱，乙酸乙酯/甲醇梯度洗脱，洗脱液经活性检测，活性部分经TLC检测(展开剂：氯仿：甲醇5：1；硫酸显色)，将只具有同一个单点的部位合并得到化合物3甲氧基环丁烷1,2-二酮。
本发明化合物对植物寄生线虫的药效试验：
1、试验用药剂：
将0.5mg-2.5mg的化合物溶于甲醇，用无菌蒸馏水稀释浓度，甲醇的终浓度不超过5％。
将未接种的发酵培养基低压浓缩后，用甲醇提取。将甲醇提取物浓缩后用甲醇溶解，再用无菌蒸馏水稀释为适用浓度作为对照。
2、制备试验用线虫
将温室培养的带有南方根结线虫Meloidogyn incognita的番茄根用无菌水洗净，解剖针挑取根结线虫的卵囊置于0.4M的KCl溶液中，在5ml离心管中依次用4ml无菌水(三次)、1ml无菌青-链霉素双抗溶液、3ml 0.1％的NaClO溶液洗涤和消毒，每一步骤均通过短暂离心(8000转30秒)除去上清液。洗涤好的虫卵置于0.4M的ZnCl2溶液中孵化48小时，二龄幼虫用移液器收集于1.5ml离心管，通过短暂离心(5000转30秒)富集备用。
3、试验方法
将本发明化合物稀释为供试药液，将药液200μl于20孔板中，加入活线虫100-150条，置于25℃下，分别于4小时、12小时、24小时在光学显微镜下检查计算线虫的死亡率。
鉴定死亡的方法为：在处理板孔中加入1-5滴5％Nacl溶液，2分钟后观察，死虫僵直，活虫则卷曲或扭动。
死亡率％＝(死亡线虫数/(死亡线虫数+存活线虫数))×100％
校正死亡率％＝样品死亡率–对照死亡率
实施例1：化合物对线虫的毒杀作用
将0.5mg3甲氧基环丁烷1,2-二酮溶于甲醇，用无菌蒸馏水稀释为0.5mg/ml溶液，甲醇的终浓度不超过5％。
按上述试验方法进行药效试验。列表所示为校正死亡率。
表1 0.5mg/ml的3甲氧基环丁烷1,2-二酮对M.incognita的毒杀作用(％)
结果表明，3甲氧基环丁烷1,2-二酮0.5mg/ml甲醇水溶液对M.incognita线虫的致死率在12小时达到50％以上，36小时达到60％以上，具有明显的杀线虫活性。
实施例2：化合物对线虫的半致死率ED50
实施例2方法同实施例1，不同之处为：将2.5mg 3甲氧基环丁烷1,2-二酮溶于甲醇，配制为1.0mg/ml的水溶液，随后倍半稀释，测定ED50(半致死率)，待测溶液中甲醇的终浓度不超过5％。
表2 3甲氧基环丁烷1,2-二酮对M.incognita线虫的ED5
结果表明，3甲氧基环丁烷1,2-二酮对M.incognita线虫的ED50(半致死率，24hr)为0.447mg/ml。
实施例3：化合物与乳化剂混合对线虫的毒杀作用
实施例3方法同实施例1，不同之处为：将0.5mg 3甲氧基环丁烷1,2-二酮溶于甲醇，再用0.3％浓度的Tween-20水溶液稀释，稀释浓度为500ppm，得具杀线虫活性物质的乳浊液。在该乳浊液中，甲醇的终浓度不超过5％，Tween-20的终浓度不超过0.3％。
表3 3甲氧基环丁烷1,2-二酮乳化制剂对M.incognita的毒杀作用
结果表明，3甲氧基环丁烷1,2-二酮与乳化剂混合后能够提高毒杀M.incognita线虫活性，提高率为10-20％。
Claims (3)
1.一种化合物，由生产菌株和辅料经发酵培养、甲醇提取、反复硅胶柱及乙酸乙酯/甲醇梯度洗脱工序后分离得到，其特征在于：
(1)生产菌株为假黄色单胞菌(Pseudoxanthomonas sp.ZKB4-4)，ZKB4-4菌株的保藏号为CGMCC No.6351；
(2)分离得到的化合物为3甲氧基环丁烷1,2-二酮，结构式为：
。
2.权利要求1所述的化合物3甲氧基环丁烷1,2-二酮在制备毒杀根结线虫制剂中的应用。
3.用权利要求1所述的化合物3甲氧基环丁烷1,2-二酮稀释得到的甲醇终浓度不超过5％、Tween-20终浓度不超过0.3％的乳浊液在制备毒杀根结线虫制剂中的应用。
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| CN1631885A (zh) * | 2004-09-30 | 2005-06-29 | 云南大学 | 一类具有毒杀线虫活性的化合物及其应用 |
| CN1670021A (zh) * | 2005-03-16 | 2005-09-21 | 云南大学 | 一类具有毒杀松材线虫活性的化合物及其应用 |
| CN102532247A (zh) * | 2011-11-08 | 2012-07-04 | 华南农业大学 | 一种来自绿木霉的杀线虫化合物及其制备方法和应用 |
| CN103087947A (zh) * | 2012-12-28 | 2013-05-08 | 云南大学 | 一株假黄色单胞菌zkb4-4及其应用 |
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| CN1670021A (zh) * | 2005-03-16 | 2005-09-21 | 云南大学 | 一类具有毒杀松材线虫活性的化合物及其应用 |
| CN102532247A (zh) * | 2011-11-08 | 2012-07-04 | 华南农业大学 | 一种来自绿木霉的杀线虫化合物及其制备方法和应用 |
| CN103087947A (zh) * | 2012-12-28 | 2013-05-08 | 云南大学 | 一株假黄色单胞菌zkb4-4及其应用 |
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