CN1051205C - 有效霉素在制备用于防治细菌性枯萎病的组合物中的用途 - Google Patents
有效霉素在制备用于防治细菌性枯萎病的组合物中的用途 Download PDFInfo
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- CN1051205C CN1051205C CN93119329A CN93119329A CN1051205C CN 1051205 C CN1051205 C CN 1051205C CN 93119329 A CN93119329 A CN 93119329A CN 93119329 A CN93119329 A CN 93119329A CN 1051205 C CN1051205 C CN 1051205C
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Classifications
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- Life Sciences & Earth Sciences (AREA)
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- Pest Control & Pesticides (AREA)
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- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Insects & Arthropods (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及有效霉素在制备用于防治细菌性枯萎病的组合物中的用途。本发明的含有有效霉素的制剂对细菌性枯萎病具有优异的防治效果，而另外还含有其他农用活性组分的组合物取决于所加入的活性组分对各种土壤传播的病害具有优异的防治效果。
Description
本发明涉及有效霉素在制备用于防治细菌性枯萎病的组合物中的用途。
各类植物总是暴露在感染植物病源体的危险之中，这些病源体生活在土壤中，造成诸如细菌性枯萎病和镰刀菌枯萎病之类的植物病害。植物通过土壤感染这些病害。植物一旦受到这些病害的侵袭，就难以用药物加以控制。另外，这些病害使植物体死亡，造成破坏性的损害。
先前用来防治这些病害的杀细菌剂，例如氯化苦和溴甲烷，具有催泪性，需要充分通风。因此，这些杀细菌剂在使用时要花费很多时间和劳动。另外，这些杀细菌剂通常用土壤熏蒸法施用。但是，这种土壤灭菌法本身实际上会产生不均匀性，这常常造成灭菌不彻底。再者，这些杀细菌性是非选择性的，因此它们也杀死腐生的土壤微生物。结果是，土壤中的微生物菌丛变得单一，在很多情形反而造成灭菌后病害的极度猖獗。此外，这些杀细菌剂不能用在种植着植物的农田上，因为它们有很强的植物毒性。因此，目前的情况是没有有效的措施来防治在种植期间侵袭植物的多种土壤病害。
另外，式(I)代表的化合物，例如有效霉素或其盐，已用来防治例如鞘枯病或猝倒病〔“最新农业数据手册”，P.386，1989，Soft Science出版社〕：
其中R1和R3各自代表氢原子或羟基；R2代表氢原子或D-吡喃葡糖基；R4代表氢原子、D-吡喃葡糖基或是D-吡喃葡糖基-D-吡喃葡糖基；R5代表一个由式(II)表示的基团：其中R6和R7各自代表氢原子或D-吡喃葡糖基。但是，已知它对于土壤传染的细菌性枯萎病完全没有防治作用。
本发明的目的之一是提供一种用于防治土壤传播的病害的组合物，它克服了上述常规杀细菌剂的缺点，使之能在作物种植期间也可以使用，並且对各类植物的各种土壤传播的病害和虫害，特别是对细菌性枯萎病，显示出极好的效果。另外，蔬菜和果树的重要病害和虫害传染和散播很快。因此，本发明的另一目的是提供一种在施用后迅速起作用的组合物，它对同时爆发的各种土壤传播的病害和虫害有效，对于种植的植物无植物毒性，而且对人类、驯养的动物、野生动物、鱼类、贝壳类等毒性很低。
为了解决上述的问题，本发明者多方面地研究了包含已知化合物的许多种用来防治土壤传播病害的混合组合物对各种土壤传播的植物病害及虫害的防治效果。结果，本发明发现，已知的长效霉素及其衍生物，即，化合物(I)或其盐，与以前用于土壤传播病害的气态化合物在化学结构和性质上完全不同，已经将其用于防治鞘枯病或猝倒病等，並且对于细菌性枯萎病具有出人意料的优异的控制作用，这种病是一种土壤传播病，但是其目标植物和出现时间与鞘枯病或猝倒病肯定不同。另外，本发明者还发现，化合物(I)或其盐与辅助的农业化学活性组分的混合物对于多种植物病害和虫害出乎意料地显示出广泛的很强控制作用。本发明者还认识到，它们由于容易安全施用而显示出很强的效果，不仅可以用土壤灌药方式施用，而且还可以直接施用，例如施用到叶子和茎上，或者直接在种子上喷粉或涂粉，或是导管内注入，对植物无植物毒性。
根据本发明提供了：
(1)一种防治土壤传播病害的组合物，该组合物包括一种式(I)代表的化合物或其盐：其中R1和R3各自代表氢原子或羟基；R2代表氢原子或D-吡喃葡糖基；R4代表氢原子、D-吡喃葡糖基或D-吡喃葡糖基-D-吡喃葡糖基；R5代表一个由式(II)表示的基团：
其中R6和R7各自代表氢原子或D-吡喃葡糖基，
(2)上述(1)中的组合物，其中土壤传播的病害是细菌性枯萎病，
(3)上述(1)中的组合物，其中式(I)代表的化合物是选自有效霉素A、有效霉素B、有效霉素C、有效霉素D、有效霉素E、有效霉素F、有效霉素G、Validoxylamine A、Validoxyla-mine B和Validoxylamine G的一种化合物，
(4)上述(1)中的化合物，其中由式(I)表示的化合物是选自有效霉素A、有效霉素B、有效霉素D和Validoxylamine A的一种化合物，
(5)上述(1)中的组合物，其中化合物(1)或其盐的含量为整个组合物重量的0.1％至80％，
(6)上述(1)中的组合物，其中还含有至少一种辅助的农业化学活性组分，
(7)上述(6)中的组合物，其中辅助的农业化学活性组分是一种杀虫剂和/或杀真菌剂，
(8)上述(6)中的组合物，其中辅助的农业化学活性组分的含量是整个组合物重量的1％至80％，
(9)上述(6)的组合物，其中辅助的农业化学活性组分选自甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)、3-(3，5-二氯苯基)-N-异丙基-2，4-二氧代咪唑烷-1-甲酰胺(异丙定)、锌离子配位的亚乙基二硫氨基甲酸锰(代森锌)、甲基-N-(氯-5-三氟甲基-2-吡啶基)-DL-丙氨酸酯(氨丙灵)、3-氯-N-(3-氯-5-三氟甲基-2-吡啶基)-α，α，α-三氯-2，6-二硝基-对甲苯胺(fluazinam)、5-乙基-5，6-二氢-8-氧代(1，3)-氧合(4，5-g)喹啉-7-碳酸(噁喹酸)、四氯间苯二腈(百菌清)、O，S-二甲基-N-乙酰基硫代磷酰胺(高灭磷)、1，3-二(硫代氨基甲酰)-2-(N，N-二甲基氨基)丙烷盐酸盐(杀螟丹)，(RS)-α-氰基-3-苯氧苄基-(RS)-2-(4-氯苯基)-3-甲基丁酸酯(fenvalerate)、2-叔丁亚氨基-3-异丙基-5-苯基-3，4，5，6-四氢-2H-1，3，5-噻二嗪-4-酮(buprofezin)、1-〔N-(6-氯-3-吡啶甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)、1-(2-氯-5-噻唑基甲基)-3-甲基-2-硝基胍(imidacloprid)和(RS)-〔O-1-(4-氯苯基)吡唑-4-基-O-乙基-S-丙基硫代磷酸酯(pyraclophos)。
(10)上述(6)的组合物，其中辅助的农业化学活性组分是1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)，
(11)上述(6)的组合物，其中辅助的农业化学活性组分是甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)，
(12)上述(6)的组合物，其中辅助的农业化学活性组分是甲基-N-(氯-5-三氟甲基-2-吡啶基)-DL-丙氨酸酯(氨丙灵)，
(13)上述(6)的组合物，其中辅助的农业化学活性组分是(RS)-2-(2，4-二氯苯基)-1-(1H-1，2，4-三唑-2-基)已-2-醇(hexaconazol)，
(14)上述(6)的组合物，其中包含着有效霉素B、甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)和1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyrum)，
(15)上述(6)的组合物，其中含有有效霉素A、甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)和1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲基氨基-2-硝基乙烯(nitenpyrum)，
(16)上述(6)的组合物，其中含有有效霉素A，锌离子配位的亚乙基二硫代氨基甲酸锰(代森锌)和1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)，
(17)一种控制土壤传播的病害的方法，其中包括使用式(I)代表的化合物或其盐：
其中R1和R3各自代表氢原子或羟基；R2代表氢原子或D-吡喃葡糖基；R4代表氢原子、D-吡喃葡糖基或D-吡喃葡糖基-D-吡喃葡糖基； R5代表由式(II)表示的一个基团：
其中R6和R7各自代表氢原子或D-吡喃葡糖基，
(18)一种用于防治土壤传播病害的液体制剂或水可分散的粉剂，其中含有由式(I)表示的一种化合物或其盐：
其中R1和R3各自代表氢原子或羟基；R2代表氢原子或D-吡喃葡糖基；R4代表氢原子、D-吡喃葡糖基或D-吡喃葡糖基-D-吡喃葡糖基；R5代表由式(II)表示的一个基团：
其中R6和R7各自代表氢原子或D-吡喃葡糖基，
(19)一种制备上述(1)或(6)的组合物的方法，包括将式(I)表示的一种化合物或其盐与辅助的农业化学活性组分及/或农用或园艺用添加剂相混合，
其中R1和R3各自代表氢原子或羟基；R2代表氢原子或D-吡喃葡糖基；R4代表氢原子、D-吡喃葡糖基或D-吡喃葡糖基-D-吡喃葡糖基；R5代表由式(II)表示的一个基团：
其中R6和R7各自代表氢原子或D-吡喃葡糖基。
表1列出了上述式(I)所代表的化合物中的优选实例。
表 1有效霉素及其衍生物 R1 R2 R3 R4 R5 R6 R7有效霉素A H H H β-D-Glc (II) H H有效霉素B H OH H β-D-Glc (II) H H有效霉素C H OH H β-D-Glc (II)α-D-Glc H有效霉素D H α-D-Glc H H (II) H H有效霉素E H H H α-D-Glc- (II) H H
(1-4)-β-
D-Glc有效霉素F H H H β-D-Glc(II) H α-D-Glc有效霉素G OH H H β-D-Glc(II) H HValidoxylamine A H H OH H (II) H HValidoxylamine B H H OH H (II) H HValidoxylamine C OH H H H (II) H H
Glc：吡喃葡糖基
在本发明中，式(I)表示的化合物可以单独使用或者组合使用。
化合物(I)的盐包括与无机酸，例如盐酸、磷酸、氢溴酸、硫酸等所成之盐；或者与有机酸，例如乙酸、甲酸、丙酸、富马酸、马来酸、丁二酸、酒石酸、柠檬酸、苹果酸、草酸、苯甲酸、甲磺酸和苯磺酸等所成之盐。如上所述，本发明的组合物含有式(I)表示的一种化合物，例如有效霉素或其盐，它们对各种土壤传播的病害，尤其是对细菌性枯萎病，有优异的防治作用。
本发明的组合物可以含有一种或者至少两种与上述式(I)化合物不同的辅助的活性组分。这些辅助的活性组分不受限制，只要它们是作为农业化学活性组分使用並且不与式(I)表示的化合物反应。例如，可以使用在“农用化学物手册”(Nippon ShoxubutsuBoeki Kyokai)提到的任何组分。具体地说，优选使用农用化学杀细菌剂和杀虫剂作为活性组分。杀虫剂包括杀螨剂，杀真菌剂包括杀细菌剂。可以在本发明中使用的杀虫剂和杀真菌剂列出如下：
氨基甲酸酯类杀虫剂：残炎威、异丙威、丁苯威、xylylcarb、metolcarbu、二甲威、苯虫威、西维因、抗蚜威、噁虫威、虫螨威、furathiocarb、carbosulfan、aminosulfulan、灭多虫、杀螟丹、fenoxycarb、alanycarb、cloethocarb、benfuracarb和fenothiocarb；
有机磷杀虫剂：倍硫磷、杀螟硫磷、丙虫磷、杀螟腈、丙硫磷、乙丙硫磷、profenofolks、苯硫磷、苯腈磷、甲胺磷、oxydeprofos、乙拌磷、甲基乙拌磷、稻丰散、马拉松、乐果、vamisothion、mecarbam、敌百虫、二溴磷、敌敌畏、chlorofenvinphos、杀虫畏、久效磷、伏杀磷、氯亚磷、甲基毒死蜱、毒死蜱、虫螨磷、二嗪农、氧嘧啶磷、打杀磷、喹噁磷、异噁唑磷、杀扑磷、杀抗松、pyraclophos、氯甲硫磷、fortress、丙胺磷、butathiofos和克瘟散；
合成除虫菊酯类杀虫剂：cyfluthrin、氯菊酯、氯氰菊酯、deltamethrin、cyhalorthrin、phenpropathrin、杀灭菊酯、flucythrinate、flubalinate、ethofenprox、silanophane、分扑菊酯、tralomethrin、cycloprot-hrin和acrinathrin；
尿素类杀虫剂：氟脲杀、chlorfluazuron、tefluben-zuron、hexaflumuron、flufenoxuron、diafenthi-uron、flucycloxuron和hexythiazox；
其它的杀虫剂：硫环杀、buprofezin、bensultap、imidacloprid、蒙五一二、fenazaquin、clofentezine、levamisol、除螨灵、cyromazine、fenpyroximate、pyridben、pyriproxyfen、sulfluramid、thiodica-rb和nitenpyram；
氨基甲酸酯类杀真菌剂：代森锌、代森锰、苯菌灵、甲基托布津、氰菌灵、多菌灵、胺丙威和diethofencarb；
抗菌素类杀真菌剂：有效霉素A、春霉霉素、avermectin和milbemycin；
酰替苯胺类杀真菌剂：mepronil、flutolanil、pency-curon、萎锈灵、氧化萎锈灵、比锈灵、灭锈胺、呋喃甲酰苯胺、环糠酰胺、beodanil、granovax、氨丙灵、ofurace、ben-alaxyl、oxadixyl、cyprofuram、clozulacon、metsulfovax和tecloftalam；
有机磷杀真菌剂：克瘟散、异稻瘟静、定菌磷、藻菌磷和tolclophos-methyl；
吡咯类杀真菌剂：异嘧菌醇、flurprimidol、菌唑灵、唑菌酮、唑菌醇、diclobutratol、paclobutatol、dinicon-azole、triflumizole、propiconazole、flutriafol、flusilazole、penconazole、丙氯灵、triapenthenol、嘧菌醇、异嘧菌醇、bitetanol、烯菌灵、etaconazole、paclobutrazol、phenapronil、viniconazole、dif-enoconazole、bromuconazole、myclobutanil、hex-aconazole、cyproconazole、furconazole-cis、fenerhanlil和tebuconazole；
甲酰亚胺类杀真菌剂：菌核利、异丙定、烯菌酮、杀菌剂、myc-lozolin和fluoroimide；
其它杀真菌剂：fthalide、diclome zin、富士一号、三环唑、噻菌灵、ferimzone、fluazinam、butiobate、pyroquilon、chlobenchiazone、百菌清、克菌丹、敌菌丹、灭菌丹、涕必灵、麦穗宁、克啉菌、fenpropimorph、嗪氨灵、乙菌定、甲菌定、土菌消、ethazol、fenpropidin、pyrifenox、dimethomorph、fenpiclonil、zarila-mid、triclamid、flusulfamide、befran、dimefu-azole、oxolinic acid和proxychlor；
外激素：okimeranolure、cherrythlure和diamol-ure；
其它农用化学活性组分：nitenpyram、fipronil、nov-aluron、flufenprox、fenpyrad或tebufenpyrad、methoxadeazono、benfluthrin、pyriproxyfen、diafenthiuron、dichlorfluanid、ftalaxyl、fla-penazole、pipanipirim、thicyofen、Opus(商品名称)、ipconazole、dimetconazole、myxothiazol、thio-imicanazole和quinconazole。
通过除式(I)代表的化合物之外还掺入辅助的活性组分，本发明的组合物可以不仅对细菌性枯萎病、而且还对于各种土壤传播的病害及虫害，例如镰刀菌枯萎病、晚疫病和黄瓜蚜虫病等，都显示出优异的效果。尤其是含有nitenpyram的组合物、含苯菌灵的组合物、含氨丙灵的组合物和含hexachonazole的组合物，它们分别对黄瓜蚜虫病、镰刀菌枯萎病、晚疫病和黄瓜蚜虫病显示出优异的防治作用。
本发明的组合物可以按照要求含有在农业和园艺组合物中通常使用的添加剂，只要这些添加剂对组合物的作用无干扰。这些添加剂的实例包括表面活性剂，载体(例如稀释剂和增量剂)，抗氧化剂(例如二丁基羟基甲苯和4，4-二硫代-6-叔丁基-3-甲基苯酚)，分散剂(例如乙二醇和甘油)，流化剂(例如白碳黑)，防腐剂(例如山梨酸钾)，增效剂，乳化剂，悬浮剂，铺展剂，渗透剂，润湿剂，增稠剂，稳定剂，粘接剂和吸收剂。
表面活性剂可以是任何阳离子表面活性剂、阴离子表面活性剂和非离子表面活性剂，可以单独使用或组合使用。阳离子表面活性剂的实例包括烷基胺盐和季铵盐。阴离子表面活性剂的实例包括木质素磺酸盐(例如木质素磺酸钙)、烷基苯磺酸盐(例如烷基苯磺酸钠)、烷基萘磺酸盐(例如烷基萘磺酸钠)、高级醇硫酸酯、高级醇醚硫酸酯、二烷基磺化琥珀酸酯和高级脂肪酸的碱金属盐。非离子表面活性剂的实例包括聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚(例如聚氧乙烯壬基苯基醚)、聚氧乙烯聚氧丙烯醚、聚氧乙烯烷基酯、失水山梨醇脂肪酸酯、聚氧乙烯失水山梨醇脂肪酸酯、聚氧乙烯聚氧丙烯嵌段共聚物和高级脂肪酸链烷醇酰胺。在这些表面活性剂之中，优选使用例如木质素磺酸盐(例如木质素磺酸钙)、烷基苯磺酸盐(例如烷基苯磺酸钠)、聚氧乙烯烷基醚、烷基萘磺酸盐(例如烷基萘磺酸钠)和聚氧乙烯壬基苯基醚。
作为载体，使用稀释剂(如液体载体以及固体载体)和增量剂。液体载体(溶剂)的合适实例包括溶剂，例如水、醇(例如甲醇、乙醇、正丙醇、异丙醇和乙二醇)、醚(例如二噁烷、四氢呋喃、乙二醇单甲醚、二乙二醇单甲醚和丙二醇单甲醚)、酮(例如丙酮和甲乙酮)、脂族烃(煤油、燃油和机械油)、芳烃(苯、甲苯、二甲苯、溶剂石脑油和甲基萘)、卤代烃(二氯甲烷、氯仿和四氯化碳)、酰胺(二甲基甲酰胺和二甲基乙酰胺)、酯(乙酸乙酯、乙酸丁酯和脂肪酸的甘油酯)和腈类(乙腈和丙腈)。固体载体的实例包括植物的粉末(例如大豆粉、烟草粉、面粉和木粉)、矿粉(例如粘土，如高岭土、膨润土和酸性粘土；滑石，如滑石粉和寿山石粉；以及二氧化硅，如硅藻土和云因粉)、氧化铝、硫黄粉、活性炭和碳酸钙。可以将这些载体中的一种或至少两种以适当的比例掺混到组合物中。
作为乳化剂、铺展剂、渗透剂、悬浮剂使用的表面活性剂包括非离子型和阴离子型表面活性剂，例如皂、聚氧烷基芳基酯(NonalTM，Takemoto Yushi公司)、烷基硫酸盐(Emal10TM、Emal40TM，Daiich Kogyo Seiyaku公司；Neopelex RTM， Kao Atlas公司)、聚乙二醇醚(Nonipol 85RTM、Nonipol 100RTM，Nonipol160RTM，Sanyo化学工业公司)和多元醇的酯(Tween 20RTM、Tween80RTM，Kao Altas公司)。
本发明的农用和园艺用组合物可以通过将式(I)代表的一种或至少两种化合物与一种或至少两种辅助的活性组分及/或上述的添加剂按着要求以常规方法混合来制备。各种制剂，例如乳液、油溶液、喷雾剂、溶液、水可分散的粉末、粉末、宁剂、粒剂和油膏，可以用本身已知並且通常用来制备农用和园艺用制剂的方法制备，例如将各组分溶解或分散在合适的液体载体中，或是将各组分与适当的固体载体混合或令组分被固体吸附，视其应用目的而定。
在制备膏剂中使用的软膏基料包括聚乙二醇、果胶、高级脂肪酸的多元醇酯(例如甘油单硬脂肪酯)、纤维素衍生物(例如甲基纤维素)、藻酸钠、膨润土、高级醇、多元醇(例如甘油)、凡士林、白凡士林、液体石蜡、猪油、各种植物油、羊毛脂、失山羊毛脂、硬化油和树脂。它们可以单独使用或组合使用，也可以适当地含有非离子型和阴离子型表面活性剂，例如皂、聚氧烷基芳基酯(Nonal，Takemoto Yushi公司)、烷基硫酸盐(Emal 10、Emal40，Daiich Kogyo Seiyaku公司；Neopelex，KaoAltas公司)、聚乙二醇醚(Nonipol 85、Nonipol 100、Nonipol 160，Sanyo化学工业公司)和多元醇的酯(Tween20、Txeen 80， Kao Atlas公司)。
在本发明的农用和园艺用组合物中含有的式(I)化合物的合适含量，对于乳液、溶液和水可分散的粉末，通常约为整个组合物重量的1％至80％，优选约1％至20％；对于油溶液和粉末，常为约0.1％至50％，优选约1％至20％；对于粒剂，常约为5％至50％，优选约1％至20％。辅助的活性组分可以以本身已知的有效数量加入。例如，对于所有各种制剂形式，它们的用量可以为组合物总重量的0.1％至80％。
加到本发明组合物中的辅助的农用化学活性组分(杀虫剂、杀螨剂和/或杀真菌剂)的数量常常是组合物总重量的约1％至80％，优选约1％至20％。
上述各有效成分之外的添加剂的含量常约为1％至50％重量，优选约1％至30％重量，但它随农业化学活性组分的种类或含量或者制剂形式而变。更具体地说，表面活性剂的加入量宜为总重量的约1％至20％，流动助剂宜为约1％至20％，载体宜为约1％至70％。当制备溶液时，表面活性剂的加入量宜为约1％至20％，优选约1％至10％，水量约为20％至90％。乳液和水可分散制剂最好是在使用时用水适当稀释或增量后(例如100-5000倍)使用。
本发明的混合组合物可以用于农用和园艺用的任何制剂。但是，特别优选将它们作为水可分散的粉末、溶液、粉末或粒剂使用。这些组合物的实例包括以下物质：
式(I)表示的化合物： 0.1％至50％重量
农用和园艺用杀真菌剂： 0至80％重量
(优选1％至80％重量)
农用和园艺用杀虫剂： 0至50％重量
(优选1％至50％重量)
表面活性剂： 1％至15％重量
载体： 10％至90％重量
更具体地说，优选使用有效霉素、validoxylamine A等作为式(I)表示的化合物；氨丙灵、fluazinam、百菌清、苯菌灵等作为农用和园艺用杀真菌剂；聚氧乙烯聚酯苯基醚、烷基萘磺酸钠、木质素磺酸钠、甲醛的高度缩合物等作为表面活性剂；粘土、碳酸钙等作为载体。
按照上述得到的含有式(I)化合物或其盐的本发明组合物具有优异的防治细菌性枯萎病的效能。另外，通过与其它农用化学活性组分相组合，本发明的组合物除了细菌性枯萎病之外还可以防治各种土壤传播的病害，例如镰刀菌枯萎病、晚疫病、黄瓜蚜虫病。本发明的组合物可以安全地用于防治各种土壤传播的病害，其慢性毒性低，因为它们是用安全和低毒性的化合物及添加剂制备的。
本发明的组合物当然可以用于植物的种子，也可以在从苗期到收割的任何时期使用。在植物病害和虫害爆发前预先使用本发明的组合物，可以防止病虫害的爆发。另外，本发明的组合物也可以正常地在爆发植物病害和虫害后立即对植物施用。特别是，本发明的组合物优选在植物生长后的收割阶段使用。
当把式(I)化合物作为农用化学物使用时，其数量要根据各种条件适当选择，这些条件包括目标植物的生长阶段和生长状态、病害及虫害的种类、蔓延的状况、化学物的施用时间和施用方法。一般来说，将组合物制备成式(I)化合物的施加量约为每10公顷3到300克，优选10到100克，辅助的农用化学活性组分(杀真菌剂和/或杀虫剂)的施加量约为每10公顷6到600克，优选约20到200克。
将施用浓度调节到式(I)化合物或其衍生物约为1到10000ppm，其它有效组分约为10到1000ppm。
施用方法包括直接向植物施加、撒粉、土壤灌药和在种子上涂粉。另外，施加量、施用浓度或施用方法可以适当变化，只要将化合物安全有效地使用于植物上。
上述的辅助的有效组分包括杀螨剂、杀线虫剂、除草剂、植物激素、植物生长调节剂、诱引剂和驱除剂。它们可以按已知比例适当地掺入。
为提高效力，可以加入金属盐，例如氯化铜和硫酸铜。另外，还可以掺入已知的稳定剂、增效剂、香料、染料、肥料、植物营养素、各种氨基酸以及低分子量或高分子量的磷酸。
此外，可以将以下的杀真菌剂、杀虫剂等掺加到这些组合物中，使其具有更优异的效力。
表2杀细菌剂化合物序号 化学名称(通用名称)F-1 甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸
酯(苯菌灵)F-2 3-(3，5-二氯苯基)-N-异丙基-2，4-二
氧咪唑烷-1-甲酰胺(异丙定)F-3 锌离子配位的亚乙基二硫代氨基甲酸锰(代森锌)F-4 甲基-N-(氯-5-三氟甲基-2-吡啶基)-DL
-丙氨酸酯(氨丙灵)F-5 3-氯-N-(3-氯-5-三氟甲基-2-吡啶基)
-α，α，α-三氟-2，6-二硝基-对甲苯胺
(fluazinam)F-6 5-乙基-5，6-二氢-8-氧(1，3)-氧合
(4，5-g)喹啉-7-碳酸(噁喹酸)F-7 四氯间苯二腈(chlorthalonil)
表3化合物序号 化学名称(通用名称)I-1 O，S-二甲基-N-乙酰基硫代磷酰胺(高灭磷)I-2 1，3-二(硫代氨基甲酰)-2-(N，N-二甲基
氨基)丙烷盐酸盐(杀螟丹)I-3 (RS)-α-氰基-3-苯氧苄基-(RS)-2-
(4-氯苯基)-3-甲基丁酸酯(fenvalerate)I-4 2-叔丁基亚氨基-3-异丙基-5-苯基-3，4，
5，6-四氢-2 H-1，3，5-噻二嗪-4-酮
(buprofezin)I-5 1-〔N-(6-氯-3-吡啶甲基)-N-乙基〕氨
基-1-甲基氨基-2-硝基乙烯(nitenpyram)I-6 1-(2-氯-5-噻唑基甲基)-3-甲基-2-硝
基胍(imidacloprid)I-7 (RS)-〔O-1-(4-氯苯基)吡唑-4-基-
O-乙基-S-丙基硫代磷酸酯(pyraclophos)
本发明的组合物含有式(I)化合物或其盐和农用及园艺用的活性组分，它对于各种土壤传播的病害，例如在烟草、芝麻、番茄、茄子、青椒、辣椒、花生、香蕉、海里康属植物、土豆、姜、streritias、南瓜等上蔓延的细菌性枯萎病，有优异的防治效果。
另外，当施加到植物和土壤上时，组合物显示出快速的防治效果，而且这些化学组分以后不保留在土壤中，因为它们被微生物分解。再者，本发明的组合物对于植物无植物毒性，作为防治土壤病害的组合物，这是有利的。
实施例
本发明将在下面更详细的说明实施例和试验实施例中加以叙述。但是，应该理解这些实施例当然不是用来限制本发明的范围。除非另外指明，实施例中的百分数均指重量。
实施例1
(溶液)有效霉素A 10％烷基萘磺酸钠 3％聚氧乙烯壬基苯基醚 3％木质素磺酸钙 1％水 83％
将上述各组分彼此均匀混合並研磨到形成溶液。使用时用水将溶液稀释1000倍，用于试验。
实施例2
(水可分散的粉末)
有效霉素A 10％
化合物F-1(苯菌灵) 10％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
碳酸钙 58％
将上述各组分彼此均匀混合，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例3
(水可分散的粉末)有效霉素A 10％化合物F-1(苯菌灵) 10％化合物F-7(百菌清) 5％烷基萘磺酸钠 3％聚氧乙烯壬基苯基醚 8％木质素磺酸钙 1％白碳黑 10％
将上述各组分彼此均匀混和，磨细，形成水可分散的粉末。在使用时用水将粉末稀释1000倍，用于试验。
实施例4
(水可分散的粉末)
有效霉素B 10％
化合物F-1(苯菌灵) 10％
化合物F-5(nitenpyram) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此均匀混合，磨细，形成水可分散的粉末。在使用时用水将粉末稀释1000倍，用于试验。
实施例5
(水可分散的粉末)
有效霉素B 10％
化合物F-4(氨丙灵) 10％
化合物I-6(imidacloprid) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此混合均匀，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例6
(水可分散的粉末)
有效霉素D 10％
化合物F-7(百菌清) 10％
化合物I-1(高灭磷) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此均匀混合，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例7
(水可分散的粉末)
Validoxylamine A 10
化合物F-4(氨丙灵) 10％
化合物I-2(杀螟丹) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此均匀混合，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例8
(水可分散的粉末)
Validoxylamine A 10
化合物F-2(异丙定) 10％
化合物I-3(fenvalerate) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此均匀混合，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例9
(水可分散的粉末)
Validoxylamine A 10％
化合物F-3(代森锌) 10％
化合物I-5(nitenpyram) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此混匀，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例10
(水可分散的粉末)
Validoxylamine A 10％
化合物F-5(fluazinam) 10％
化合物I-4(buprofezin) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此混匀，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
实施例11
(水可分散的粉末)
Validoxylamine A 10％
化合物F-1(苯菌灵) 10％
化合物I-6(imidacloprid) 5％
烷基萘磺酸钠 3％
聚氧乙烯壬基苯基醚 8％
木质素磺酸钙 1％
白碳黑 10％
将上述各组分彼此混匀，磨细，形成水可分散的粉末。使用时用水将粉末稀释1000倍，用于试验。
试验实施例1防治番茄细菌性枯萎病的试验(土壤灌药)
受试验的植物：番茄(Lycopersicon esculentumMill，品种：Ogata Fukuju)，出苗2周后移植到5Cm的盆中，在空调室中再培育2周后用于试验。
制剂的施用：将实施例中各种制剂用水稀释1000倍，用土壤灌药法以5毫升/盆的数量施药。
接种方法：用大约3ml含番茄细菌性枯萎病病原体(Pseudomonas solanacearum E.F.Smith，在Takeda化学工业公司分离的菌种)的悬浮液对番茄接种，其浓度为约108CFU/mL(CFU：菌落形成单位)，在施加制剂1天后用灌药法接种。在室温中于30℃下保持2周后，计数枯萎的植物数目，用公式(1)计算防治值。
防治值(％)＝(1-施药地带枯萎植物数/未施药地带枯萎植
物数)×100 ……(1)
试验实施例2防治茄细菌性枯萎病的试验(施加到茎和叶上)
受试验的植物：茄(Solanum melongene L，品种：Senryo No.2)，出苗后2周时移植到5Cm的盆中，在空调室中再培育2周后用于试验。
制剂的施用：用水将实施例中的水可分散粉末稀释1000倍，用喷雾器施加到茎和叶上，直到稀释的粉末从上面滴下。
接种方法：用大约3ml含番茄细菌性枯萎病病原体(pseudo-monas solanacearum E.F.Smith，Takeda化学工业公司分离的菌种)的悬浮液在施加制剂1天后浇灌土壤，其浓度约为108CFU/mL，切除茄子的毛根以进行切根接种。在室温中于30℃下保持2周后，计数枯萎的植物数，按上述公式(1)计算防治值。
试验实施例3防治番茄细菌性枯萎病的试验(导管内注入)
受试验的植物：番茄(Lycopersicon esculentumMill，品种：Ogata Fukuju)，出苗后2周时移植到9Cm的盆中，再在空调室中培育4周后用于试验。
制剂的施用：用水将实施例中的水可分散粉末稀释1000倍，利用滴灌装置向导管中注入400ml。
接种方法：在施加制剂1天后，用大约3毫升浓度约为108CFU/ml的含番茄细菌性枯萎病菌(Pseudomonas solan-acearum E.F.Smith，菌种由Takeda化学公司分离)的悬浮液浇灌土壤，切除番茄的毛根以进行切根接种。在室温中于30℃下保持2周后，计数枯萎的植物数，按上述公式(1)计算防治值。
试验实施例4防治番茄镰刀菌枯萎病的试验(土壤灌药)
受试验的植物：番茄(Lycopersicon esculentumMill，品种：Ogata Fukuju)，出苗2周后移植到5Cm的盆中，再在空调室内培育2周后用于试验。
制剂的施用：用水将实施例中水可分散的粉末稀释1000倍，用土壤灌药法以5ml/盆的数量施用。
接种方法：在施用制剂1天后，用大约3ml含有磨细的番茄镰刀菌枯萎病菌丝体(Fusarium oxysporum f.sp.lycope-rsici，Takeda化学工业公司分离的菌种)的悬浮液浇灌土壤。在室温中于30℃下保持2周后，计数枯萎的植物数目，用上述公式(1)计算防治值。
试验实施例5防治蕃茄晚疫病的试验(土壤灌药)
受试验的植物：蕃茄(Lycopersicon esculentumMill，品种：Ogata Fukuju)，出苗2周后移植到5Cm的盆中，再在空调室中培育2周后用于试验。
制剂的施用：用水将实施例的水可分散性粉末稀释1000倍，用土壤灌药法以5cm/盆的数量施药。
接种方法：在施药1天以后，用番茄晚疫病菌(phytophthorainfestans de Bary，Takeda化学工业公司分离的菌种)游动孢子囊的悬浮液(浓度约为105游动孢子囊/ml)对番茄的茎叶喷洒进行接种，直到悬浮液从茎叶上滴落。在20℃于高湿度条件下保持5天之后，检查发病的面积，防治值按公式(2)计算：
防治值(％)＝(1-施药面积中发病面积率/未施药面积中发
病面积率)×100 ……(2)
试验实施例6对黄瓜蚜虫杀虫效果的试验
在施加制剂1天以前在每株黄瓜幼苗(出苗约3周)上放置10只雌性成年蚜虫，用水将本发明的组合物稀释1000倍后施用。施药2天后，计数存活的蚜虫数以了解死亡的蚜虫数，按公式(3)计算防治值：
防治值(％)＝(1-在施药区内的死亡的蚜虫数/
释放的蚜虫数)×100 ……(3)
试验实施例1至6的结果总结在表4和5中。
表 4
实验1的结果
番茄细菌性枯 茄子细菌性枯 番茄细菌性枯
萎病(土壤灌 萎病(茎叶施 萎病(容器内
药)防治值 药)防治值 喷药)防治值
％ ％ ％实施例1的化合物 100 100 100实施例2的化合物 100 100 100实施例3的化合物 100 100 100实施例4的化合物 100 100 100实施例6的化合物 100 100 100实施例7的化合物 100 100 100实施例8的化合物 100 100 100实施例9的化合物 100 100 100实施例10的化合物 100 100 100实施例11的化合物 100 100 100
表 5
实验2的结果
番茄镰刀菌枯 番茄晚疫 黄瓜蚜虫
萎病防治值 病防治值 防治值
％ ％ ％实施例1的化合物 - - -实施例2的化合物 100 - -实施例3的化合物 100 100 -实施例4的化合物 100 - 100实施例5的化合物 - 100 100实施例6的化合物 - 100 100实施例7的化合物 - 100 -实施例8的化合物 - - 100实施例9的化合物 - 100 100实施例10的化合物 - 100 -实施例11的化合物 100 - 100
-：未试验
上面列出的试验结果说明本发明的含有式(I)化合物或其盐的制剂对于细菌性枯萎病有优异的防治效果，而另外还含有其它农用活性组分的组合物，则除了细菌性枯萎病以外，还根据所加入的活性组分对各种土壤传播的病害，例如镰刀菌枯萎病、晚疫病和黄瓜蚜虫病等，具有优异的防治效果。
Claims (13)
1.有效霉素A、有效霉素B、有效霉素D或validoxylamineA或其盐在制备用于防治细菌性枯萎病的组合物中的用途。
2.根据权利要求1的用途，其中有效霉素A、有效霉素B、有效霉素D和validoxylamine A或其盐的含量为整个组合物重量的0.1％至80％。
3.根据权利要求1的用途，其中所述组合物还含有至少一种辅助的农业化学活性组分。
4.根据权利要求3的用途，其中辅助的农业化学活性组分是一种杀虫剂和/或杀真菌剂。
5.根据权利要求3的用途，其中辅助的农业化学活性组分的含量是整个组合物重量的1％至80％。
6.根据权利要求3的用途，其中辅助的农业化学活性组分选自甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)、3-(3，5-二氯苯基)-N-异丙基-2，4-二氧代咪唑烷-1-甲酰胺(异丙定)、锌离子配位的亚乙基二硫氨基甲酸锰(代森锌)、甲基-N-(氯-5-三氟甲基-2-吡啶基)-DL-丙氨酸酯(氨丙灵)、3-氯-N-(3-氯-5-三氟甲基-2-吡啶基)-2，2，2-三氟-2，6-二硝基-对甲苯胺(fluazinam)、5-乙基-5，6-二氢-8-氧代(1，3)-氧合(4，5-g)喹啉-7-碳酸(恶喹酸)、四氯间苯二腈(百菌清)、O，S-二甲基-N-乙酰基硫代磷酰胺(高灭磷)、1，3-二(硫代氨基甲酰)-2-(N，N-二甲基氨基)丙烷盐酸盐(杀螟丹)、(RS)-α-氰基-3-苯氧苄基-(RS)-2-(4-氯苯基)-3-甲基丁酸酯(fenvalerate)、2-叔丁亚氨基-3-异丙基-5-苯基-3，4，5，6-四氢-2H-1，3，5-噻二嗪-4-酮(buprofezin)、1-〔N-(6-氯-3-吡啶甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)、1-(2-氯-5-噻唑基甲基)-3-甲基-2-硝基胍(imidacloprid)和(RS)-〔O-1-(4-氯苯基)吡唑-4-基-O-乙基-S-丙基硫代磷酸酯(pyraclopbos)。
7.根据权利要求3的用途，其中辅助的农业化学活性组分是1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)。
8.根据权利要求3的用途，其中辅助的农业化学活性组分是甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)。
9.根据权利要求3的用途，其中辅助的农业化学活性组分是甲基-N-(氯-5-三氟甲基-2-吡啶基)-DL-丙氨酸酯(氨丙灵)。
10.根据权利要求3的用途，其中辅助的农业化学活性组分是(RS)-2-(2，4-二氯苯基)-1-(1H-1，2，4三唑-2-基)己-2-醇(hexaconazol)。
11.根据权利要求3的用途，其中所述组合物包含有效霉素B、甲基-1-(丁基氨基甲酰)-2-苯并咪唑氨基甲酸酯(苯菌灵)和1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)。
12.根据权利要求3的用途，其中所述组合物包含有效霉素A，锌离子配位的亚乙基二硫代氨基甲酸锰(代森锌)和1-〔N-(6-氯-3-吡啶基甲基)-N-乙基〕氨基-1-甲氨基-2-硝基乙烯(nitenpyram)。
13.根据权利要求1-12任一项的用途，其中所述组合物为用于防治细菌性枯萎病的液体制剂或水可分散的粉剂。
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| KR100746310B1 (ko) * | 2006-12-07 | 2007-08-06 | 주식회사 파이오니아 | 풋마름병 방제 효과를 갖는 페니바실러스 폴리믹사ｋｐｂ３종 |
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| US4089947A (en) * | 1971-04-20 | 1978-05-16 | Takeda Chemical Industries Ltd. | Antibiotic compositions containing validamycin compounds |
| JPH1025703A (ja) * | 1996-07-12 | 1998-01-27 | Japan Metals & Chem Co Ltd | アーチ型舗装用ブロック |
| JPH1025705A (ja) * | 1996-07-12 | 1998-01-27 | Tateyama Alum Ind Co Ltd | 融雪用発熱マット |
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| JPS5618997A (en) * | 1979-07-24 | 1981-02-23 | Takeda Chem Ind Ltd | Validamycin a derivative, and agricultural and horticultural fungicide containing said derivative |
| JPS6372609A (ja) * | 1986-09-16 | 1988-04-02 | Nippon Tokushu Noyaku Seizo Kk | 農園芸用殺虫殺菌組成物 |
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- 1993-10-20 CN CN93119329A patent/CN1051205C/zh not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089947A (en) * | 1971-04-20 | 1978-05-16 | Takeda Chemical Industries Ltd. | Antibiotic compositions containing validamycin compounds |
| JPH1025703A (ja) * | 1996-07-12 | 1998-01-27 | Japan Metals & Chem Co Ltd | アーチ型舗装用ブロック |
| JPH1025705A (ja) * | 1996-07-12 | 1998-01-27 | Tateyama Alum Ind Co Ltd | 融雪用発熱マット |
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| KR940008571A (ko) | 1994-05-16 |
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