CN104470362A - 植物病害防除组合物及其用途 - Google Patents
植物病害防除组合物及其用途 Download PDFInfo
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- CN104470362A CN104470362A CN201380038102.6A CN201380038102A CN104470362A CN 104470362 A CN104470362 A CN 104470362A CN 201380038102 A CN201380038102 A CN 201380038102A CN 104470362 A CN104470362 A CN 104470362A
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Classifications
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
含有式(I)〔式中,R1表示氯原子、溴原子、氰基或甲基,R2表示氢原子或氟原子。〕所示的哒嗪化合物和式(A)所示的化合物的植物病害防除组合物显示出对植物病害的优异的防除效果。式(A):
Description
技术领域
本发明涉及植物病害防除组合物及其用途。
背景技术
以往,为了防除植物病害而开发许了多化合物供于实用(例如,参照专利文献1、专利文献2。)。
现有技术文献
专利文献
专利文献1:国际公开第2005/121104号小册子
专利文献2:国际公开第2006/001175号小册子
发明内容
发明要解决的课题
本发明的课题在于提供对植物病害具有优异的防除效力的组合物。
解决课题的手段
本发明人为了发现对植物病害具有优异的防除效力的组合物而进行了研究,结果发现,含有下述式(I)所示的哒嗪化合物和式(A)所示的化合物的植物病害防除组合物对植物病害具有优异的防除效力,从而完成了本发明。
即,本发明同下。
[1]一种植物病害防除组合物,其含有式(I)所示的哒嗪化合物和下述式(A)所示的化合物,
式(I)中,
R1表示氯原子、溴原子、氰基或甲基,
R2表示氢原子或氟原子,
式(A):
[2]根据[1]所述的植物病害防除组合物,其中,哒嗪化合物与式(A)所示的化合物的重量比为哒嗪化合物/式(A)所示的化合物=0.1/1~10/1。
[3]一种植物病害防除方法,其包含将式(I)所示的哒嗪化合物和下述式(A)所示的化合物的有效量对植物或栽培植物的土壤进行处理的工序,
式(I)中,
R1表示氯原子、溴原子、氰基或甲基,
R2表示氢原子或氟原子,
式(A):
[4]根据[3]所述的植物病害防除方法,其中,哒嗪化合物与式(A)所示的化合物的重量比为哒嗪化合物/式(A)所示的化合物=0.1/1~10/1。
[5]根据[3]或[4]所述的植物病害防除方法,其中,植物或栽培植物的土壤为小麦或栽培小麦的土壤。
具体实施方式
本发明的植物病害防除组合物(以下,记为本发明组合物。)含有式(I)
〔式中,
R1表示氯原子、溴原子、氰基或甲基,
R2表示氢原子或氟原子。〕
所示的哒嗪化合物(以下,记为本哒嗪化合物。)和式(A)
所示的化合物(以下,记为本化合物(A)。)。
作为本发明组合物中使用的本哒嗪化合物的形态,可列举例如以下的哒嗪化合物。
式(I)中,R1为氯原子或甲基的哒嗪化合物;
式(I)中,R1为氯原子的哒嗪化合物;
式(I)中,R1为甲基的哒嗪化合物;
式(I)中,R1为氰基的哒嗪化合物;
式(I)中,R2为氢原子的哒嗪化合物;
式(I)中,R2为氟原子的哒嗪化合物;
式(I)中,R1为氯原子、氰基或甲基,R2为氢原子的哒嗪化合物;
式(I)中,R1为氯原子、氰基或甲基,R2为氟原子的哒嗪化合物。
式(I)中,R1为氯原子,R2为氢原子、或氟原子的哒嗪化合物。
式(I)中,R1为溴原子、氰基或甲基,R2为氢原子的哒嗪化合物。
式(I)中,R1为溴原子、氰基或甲基,R2为氟原子的哒嗪化合物。
作为本哒嗪化合物,可具体列举如下哒嗪化合物。
式(I)中,R1为氯原子、R2为氢原子的哒嗪化合物(以下,记为本哒嗪化合物(1)。);
式(I)中,R1为溴原子、R2为氢原子的哒嗪化合物(以下,记为本哒嗪化合物(2)。);
式(I)中,R1为氰基、R2为氢原子的哒嗪化合物(以下,记为本哒嗪化合物(3)。);
式(I)中,R1为甲基、R2为氢原子的哒嗪化合物(以下,记为本哒嗪化合物(4)。);
式(I)中,R1为氯原子、R2为氟原子的哒嗪化合物(以下,记为本哒嗪化合物(5)。);
式(I)中,R1为溴原子、R2为氟原子的哒嗪化合物(以下,记为本哒嗪化合物(6)。);
式(I)中,R1为氰基、R2为氟原子的哒嗪化合物(以下,记为本哒嗪化合物(7)。);
式(I)中,R1为甲基、R2为氟原子的哒嗪化合物(以下,记为本哒嗪化合物(8)。)。
可以通过例如在国际公开第2005/121104号小册子中记载的方法来制造本哒嗪化合物中,式(I)中R1为氯原子或溴原子的哒嗪化合物。
可以通过在国际公开第2006/001175号小册子中记载的方法来制造本哒嗪化合物中,式(I)中R1为甲基的哒嗪化合物。
可以通过例如使本哒嗪化合物中式(I)中R1为溴原子的化合物(I-1)与氰化铜反应来制造本哒嗪化合物中式(I)中R1为氰基的化合物(I-2)。
〔式中,R2表示与上述相同的意思。〕
通常在溶剂的存在下进行该反应。
作为反应中使用的溶剂,可列举例如N,N-二甲基乙酰胺等非质子性极性溶剂。
该反应中使用的氰化铜的量相对于化合物(I-1)1摩尔通常为1~1.5摩尔的比例。
该反应的反应温度通常为120~180℃的范围,反应时间通常为1~24小时的范围。
反应结束后,例如,将反应混合物与水和有机溶剂混合后过滤,将滤液分液,然后将得到的有机层水洗后进行干燥、浓缩等操作,由此可以分离化合物(I-2)。也可以通过色谱法、重结晶等进一步精制分离出的化合物(I-2)。
可以通过使本哒嗪化合物中R1为氯原子的化合物(I-3)与式(2)
CH3-MgX (2)
〔式中,X表示溴原子或氯原子。〕
所示的格氏试剂在铁催化剂的存在下反应来制造本哒嗪化合物中式(I)中R1为甲基的化合物(I-4)。
〔式中,R2表示与上述相同的意思。〕
通常在溶剂的存在下进行该反应。
作为反应中使用的溶剂,可列举例如四氢呋喃、乙醚及N-甲基吡咯烷酮、以及它们的混合溶剂。反应溶剂为四氢呋喃与N-甲基吡咯烷酮的混合物时,四氢呋喃与N-甲基吡咯烷酮的混合比以容量比计通常为30:1~3:1的范围。
作为该反应中使用的铁催化剂,可列举例如乙酰丙酮铁(III)及氯化铁(III)。使用的铁催化剂的量相对于化合物(I-3)1摩尔通常为0.01~0.3摩尔的比例。
该反应的反应温度通常为-20℃~30℃的范围,反应时间通常为0.1~6时间的范围。
反应结束后,例如,将反应混合物与盐酸混合后进行有机溶剂萃取,水洗得到的有机层后进行干燥、浓缩等操作,由此可以分离化合物(I-4)。也可以通过色谱法、重结晶等进一步精制分离出的化合物(I-4)。
本化合物(A)为公知的化合物,在例如国际公开第02/10101号小册子中记载着。这些化合物可以由市售的制剂获得、或通过公知的方法合成。
需要说明的是,本化合物(A)中存在1个手性碳原子,存在基于该手性碳原子的R体(下述式(A1)
所示。)及S体(下述式(A2)
所示。)的两对映异构体,但在本发明中本化合物(A)可以使用任意的对映异构体比的物质。
可以通过在国际公开第02/10101号小册子中记载的方法来合成该对映异构体。
本发明组合物中的本哒嗪化合物与本化合物(A)的重量比通常为本哒嗪化合物/本化合物(A)=0.01/1~500/1,优选为0.1/1~10/1,更优选为0.1/1~2/1。
本发明组合物可以为本哒嗪化合物与本化合物(A)的混合物本身,但本发明组合物通常将本哒嗪化合物、本化合物(A)及不活泼载体混合,根据需要添加表面活性剂、其他制剂用辅助剂,制剂化为油剂、乳剂、流动剂、水合剂、颗粒水合剂、粉剂、粒剂等。该制剂可以直接或添加其他不活泼成分而作为植物病害防除剂使用。
在本发明组合物中,通常合计含有0.1~99重量%,优选含有0.2~90重量%,更优选含有1~80重量%本哒嗪化合物及本化合物(A)。
作为制剂化时使用的固体载体,可列举例如由高岭土、凹凸棒石粘土、膨润土、蒙脱土、酸性白土、叶蜡石、滑石、硅藻土、方解石等矿物;玉米穗轴粉、核桃壳粉等天然有机物;尿素等合成有机物;碳酸钙、硫酸铵等盐类;合成含水氧化硅等合成无机物等构成的微粉或粒状物等,作为液体载体,可列举例如二甲苯、烷基苯、甲基萘等芳香族烃类;2-丙醇、乙二醇、丙二醇、乙二醇单乙醚等醇类;丙酮、环己酮、异佛尔酮等酮类;大豆油、棉籽油等植物油;石油系脂肪族烃类、酯类、二甲基亚砜、乙腈及水。
作为表面活性剂,可列举例如烷基硫酸酯盐、烷基芳基磺酸盐、二烷基磺基琥珀酸盐、聚氧亚乙基烷基芳基醚磷酸酯盐、木质素磺酸盐、萘磺酸酯甲醛缩聚物等阴离子表面活性剂;及聚氧亚乙基烷基芳基醚、聚氧亚乙基烷基聚氧亚丙基嵌段共聚物、失水山梨醇脂肪酸酯等非离子表面活性剂;及烷基三甲基铵盐等阳离子表面活性剂。
作为其他制剂用辅助剂,可列举例如聚乙烯醇、聚乙烯吡咯烷酮等水溶性高分子;阿拉伯胶;海藻酸及其盐;CMC(羧甲基纤维素)、黄原胶等多糖类;硅酸铝镁盐、氧化铝溶胶等无机物;防腐剂;着色剂及PAP(酸式磷酸异丙酯)、BHT等稳定化剂。
另外,在将本哒嗪化合物和本化合物(A)分别通过上述的方法制剂化的基础上,也可以根据需要用水稀释后将各自的制剂或它们的稀释液混合来制备本发明组合物。
可以为了保护植物免受植物病害而使用本发明组合物。
作为本发明组合物具有防除效力的植物病害,可列举例如下述植物病害。
稻的病害:稻瘟病(Magnaporthe grisea)、芝麻叶斑病(Cochliobolusmiyabeanus)、纹枯病(Rhizoctonia solani)、恶苗病(Gibberella fujikuroi)。
小麦的病害:白粉病(Erysiphe graminis)、赤霉病(Fusariumgraminearum、F.avenacerum、F.culmorum、Microdochium nivale)、条锈病(Puccinia striiformis、P.graminis、P.recondita)、红色雪腐病(Micronectriella nivale)、雪腐小粒菌核病(Typhula sp.)、裸黑穗病(Ustilago tritici)、腥黑穗病(Tilletia caries)、眼纹病(Pseudocercosporellaherpotrichoides)、叶枯病(Mycosphaerella graminicola)、稃枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici-repentis)。
大麦的病害:白粉病(Erysiphe graminis)、赤霉病(Fusariumgraminearum、F.avenacerum、F.culmorum、Microdochium nivale)、条锈病(Puccinia striiformis、P.graminis、P.hordei)、裸黑穗病(Ustilago nuda)、云形病(Rhynchosporium secalis)、网斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑叶病(Pyrenophora graminea)、丝核菌属菌所致的苗立枯病(Rhizoctonia solani)。
玉米的病害:黑穂病(Ustilago maydis)、芝麻叶斑病(Cochliobolusheterostrophus)、豹纹病(Gloeocercospora sorghi)、南方锈病(Pucciniapolysora)、灰斑病(Cercospora zeae-maydis)、丝核菌属菌所致的苗立枯病(Rhizoctonia solani)。
柑橘类的病害:黑点病(Diaporthe citri)、疮痂病(Elsinoe fawcetti)、果实腐败病(Penicillium digitatum,P.italicum)、黑胫病(Phytophthoraparasitica、Phytophthora citrophthora)。
苹果的病害:花腐病(Monilinia mali)、腐乱病(Valsaceratosperma)、白粉病(Podosphaera leucotricha)、斑点落叶病(Alternaria alternata applepathotype)、黑星病(Venturia inaequalis)、炭疽菌(Colletotrichum acutatum)、疫病(Phytophthora cactorum)。
梨的病害:黑星病(Venturianashicola、V.pirina)、黑斑病(Alternariaalternate Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum)、疫病(Phytophthora cactorum);
桃的病害:灰星病(Monilinia fructicola)、黑星病(Cladosporiumcarpophilum)、拟茎点霉腐烂病(Phomopsis sp.)。
葡萄的病害:黑痘病(Elsinoe ampelina)、晩腐病(Glomerella cingulata)、白粉病(Uncinula necator)、条锈病(Phakopsora ampelopsidis)、黑斑病(Guignardia bidwellii)、霜霉病(Plasmopara viticola)。
柿的病害:炭疽菌(Gloeosporium kaki)、落叶病(Cercospora kaki、Mycosphaerella nawae)。
瓜类的病害:炭疽菌(Colletotrichum lagenarium)、白粉病(Sphaerotheca fuliginea)、蔓枯病(Mycosphaerella melonis)、枯萎病(Fusarium oxysporum)、霜霉病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.);
西红柿的病害:轮纹病(Alternaria solani)、叶霉病(Cladosporiumfulvum)、疫病(Phytophthora infestans)。
茄子的病害:褐纹病(Phomopsis vexans)、白粉病(Erysiphecichoracearum)。
十字花科蔬菜的病害:黑斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根肿病(Plasmodiophora brassicae)、霜霉病(Peronospora parasitica)。
葱的病害:条锈病(Puccinia allii)、霜霉病(Peronospora destructor)。
大豆的病害:紫斑病(Cercospora kikuchii)、黑痘病(Elsinoe glycines)、黑点病(Diaporthe phaseolorum var.sojae)、褐纹病(Septoria glycines)、斑点病(Cercospora sojina)、条锈病(Phakopsora pachyrhizi)、茎疫病(Phytophthora sojae)、丝核菌属菌所致的苗立枯病(Rhizoctonia solani)褐色轮纹病(Corynespora casiicola)、菌核病(Sclerotinia sclerotiorum)。
云豆的病害:炭疽菌(Colletotrichum lindemthianum)。
花生的病害:黑斑病(Cercospora personata)、褐斑病(Cercosporaarachidicola)、白绢病(Sclerotium rolfsii)。
豌豆的病害:白粉病(Erysiphe pisi)。
土豆的病害:夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、绯腐病(Phytophthora erythroseptica)、粉状疮痂病(Spongosporasubterranean f.sp.subterranea)。
草莓的病害:白粉病(Sphaerotheca humuli)、炭疽菌(Glomerellacingulata)。
茶的病害:网饼病(Exobasidium reticulatum)、白星病(Elsinoeleucospila)、轮斑病(Pestalotiopsis sp.)、炭疽菌(Colletotrichumtheae-sinensis)。
烟草的病害:赤星病(Alternaria longipes)、白粉病(Erysiphecichoracearum)、炭疽菌(Colletotrichum tabacum)、霜霉病(Peronosporatabacina)、疫病(Phytophthora nicotianae)。
油菜籽的病害:菌核病(Sclerotinia sclerotiorum)、丝核菌属菌所致的苗立枯病(Rhizoctonia solani)。
棉的病害;丝核菌属菌所致的苗立枯病(Rhizoctoniasolani)。
甜菜的病害:褐斑病(Cercospora beticola)、叶腐病(Thanatephoruscucumeris)、根腐病(Thanatephorus cucumeris)、黑根病(Aphanomycescochlioides)。
蔷薇的病害:黑星病(Diplocarpon rosae)、白粉病(Sphaerothecapannosa)、霜霉病(Peronospora sparsa)。
菊及菊科蔬菜的病害:霜霉病(Bremia lactucae)、褐斑病(Septoriachrysanthemi-indici)、白条锈病(Puccinia horiana)。
各种作物的病害:由腐霉属菌引起的病害(Pythium aphanidermatum、Pythium debarianum、Pythium graminicola、Pythium irregulare、Pythiumultimum)、灰霉病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum)。
萝卜的病害:黑斑病(Alternaria brassicicola)。
草的病害:银斑病(Sclerotinia homeocarpa)、叶腐病及纹枯病(Rhizoctonia solani)。
香蕉的病害:黑条叶斑病(Mycosphaerella fijiensis、Mycosphaerellamusicola)。
向日葵的病害:霜霉病(Plasmopara halstedii)。
由曲霉属(Aspergillus属)、青霉菌属(Penicillium属)、镰刀菌属(Fusarium属)、赤霉菌属(Gibberella属)、木霉属(Tricoderma属)、根串珠霉属(Thielaviopsis属)、根霉属菌(Rhizopus属)、毛霉属(Mucor属)、伏革菌属(Corticium属)、茎点霉属(Phoma属)、丝核菌属(Rhizoctonia属)、及色二孢属(Diplodia属)菌等引起的各种作物的种子病害或生长初期的病害。
由杆菌属(Polymixa属)或油壶菌属(Olpidium属)等传播的各种作物的病毒病。
作为可以使用本发明组合物的植物,可列举例如下述植物。
农作物:玉米、稻、小麦、大麦、黑麦、燕麦、高粱、棉花、大豆、花生、荞麦、甜菜、油菜籽、向日葵、甘蔗、烟草等。
蔬菜:茄科蔬菜(茄子、西红柿、胡椒、辣椒、土豆等);葫芦科蔬菜(黄瓜、南瓜、西葫芦、西瓜、甜瓜、南瓜(squash)等);十字花科蔬菜(萝卜、芜菁甘蓝、辣根、球茎甘蓝、大白菜、卷心菜、芥菜、西兰花、菜花等);菊科蔬菜(牛蒡、苘蒿、菊芋、生菜等);百合科蔬菜(葱、洋葱、大蒜、芦笋);伞形科蔬菜(胡萝卜、香菜、芹菜、美国防风等);藜科蔬菜(菠菜、瑞士甜菜等);唇形科蔬菜(紫苏、薄荷、罗勒等);草莓、甘薯、日本薯蓣、芋头等、
花卉、
观叶植物、
草、
果树:梨果类(苹果、西洋梨、日本梨、木瓜、榅桲等);核果类(桃子、李子、油桃、梅子、樱桃、杏子、西梅等);柑橘类(温州蜜柑、橙子、柠檬、酸橙、葡萄柚等);坚果类(栗子、胡桃、榛子、杏仁、开心果、腰果、澳洲坚果等);浆果类(蓝莓、蔓越莓、黑莓、覆盆子等);葡萄、柿子、橄榄、枇杷、香蕉、咖啡、海枣、椰树等、
果树以外的树木:茶树、桑树、花木;行道树(日本白蜡树、桦树、山茱萸、桉树、银杏、丁香、枫树、橡树、白杨、紫荆、枫香树、梧桐、榉树、日本香柏、枞树、铁杉、杜松、松树、云杉、红豆杉等)。
上述植物可以为通过基因重组技术而赋予了耐性的植物。
上述中,特别是对在小麦中发生的植物病害可以期待高的防除效果。
另外,作为在这些作物中发生的植物病害中,可以期待特别高的效力的小麦的病害,可列举白粉病(Erysiphe graminis)、赤霉病(Fusariumgraminearum、F.avenacerum、F.culmorum、Microdochium nivale)、条锈病(Puccinia striiformis、P.graminis、P.recondita)、红色雪腐病(Microdochium nivale)、核瑚菌属病(Typhula sp.)、散黑穗病(Ustilagotritici)、腥黑穗病(Tilletia caries)、眼纹病(Pseudocercosporellaherpotrichoides)、叶枯病(Mycosphaerella graminicola)、稃枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici-repentis);等。
作为本发明组合物的形态,可列举例如以下的形态。
含有本哒嗪化合物(1)和本化合物(A)的组合物;
含有本哒嗪化合物(2)和本化合物(A)的组合物;
含有本哒嗪化合物(3)和本化合物(A)的组合物;
含有本哒嗪化合物(4)和本化合物(A)的组合物;
含有本哒嗪化合物(5)和本化合物(A)的组合物;
含有本哒嗪化合物(6)和本化合物(A)的组合物;
含有本哒嗪化合物(7)和本化合物(A)的组合物;
含有本哒嗪化合物(8)和本化合物(A)的组合物;
以本哒嗪化合物(1)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(1)和本化合物(A)的组合物;
以本哒嗪化合物(2)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(2)和本化合物(A)的组合物;
以本哒嗪化合物(3)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(3)和本化合物(A)的组合物;
以本哒嗪化合物(4)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(4)和本化合物(A)的组合物;
以本哒嗪化合物(5)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(5)和本化合物(A)的组合物;
以本哒嗪化合物(6)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(6)和本化合物(A)的组合物;
以本哒嗪化合物(7)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(7)和本化合物(A)的组合物;
以本哒嗪化合物(8)/本化合物(A)=0.1/1~10/1的重量比含有本哒嗪化合物(8)和本化合物(A)的组合物;
通过用本哒嗪化合物和本化合物(A)的有效量对植物或栽培植物的土壤进行处理来进行本发明的植物病害防除方法(以下,记为本发明防除方法。)。作为该植物,可列举例如植物的茎叶、植物的种子及植物的球根。需要说明的是,此处球根是指鳞茎、球茎、根茎、块茎、块根及根托。
本发明防除方法中,可以在同时期分别在植物或栽培植物的土壤中用本哒嗪化合物及本化合物(A)进行处理,但通常从处理时的简便性的观点出发,以本发明组合物的形式进行处理。
本发明防除方法中,作为本哒嗪化合物及本化合物(A)的处理方法,可列举例如茎叶处理、土壤处理、根部处理及种子处理。
作为该茎叶处理,可列举例如通过茎叶喷洒及树干喷洒,在栽培的植物的表面进行处理的方法。
作为该土壤处理,可列举例如土壤喷洒、土壤混合及向土壤的药液灌注。
作为该根部处理,可列举例如在含有本哒嗪化合物和本化合物(A)的药液中浸渍植物的整体或根部的方法、及使含有本哒嗪化合物和本化合物(A)和固体载体的固体制剂附着于植物的根部的方法。
作为该种子处理,可列举例如本发明组合物对欲进行保护而免受植物病害的植物的种子或球根的处理,详细而言,可列举例如将本发明组合物的悬浊液制成雾状而向种子表面或球根表面喷吹的喷吹处理、在本发明组合物的水合剂、乳剂或流动剂中加入少量的水或直接向种子或球根涂布的涂沫处理、在本发明组合物的溶液中将种子浸渍一定时间的浸渍处理、将本发明组合物和聚合物混合后对种子表面进行膜涂布的膜涂布处理、将本发明组合物和粉体混合并将种子作为核而成形为颗粒状的颗粒涂布处理。
本发明防除方法中的本哒嗪化合物与本化合物(A)的处理量也根据要处理的植物的种类、作为防除对象的植物病害的种类或发生频率、制剂形态、处理时期、处理方法、处理场所、气象条件等变化,但对植物的茎叶处理时或对栽培植物的土壤处理时,本哒嗪化合物与本化合物(A)的合计量每1000m2通常为1~500g,优选为2~200g,更优选为10~100g。另外对种子的处理中的本哒嗪化合物与本化合物(A)的处理量以本哒嗪化合物与本化合物(A)的合计量计,每1kg种子通常为0.001~10g,优选为0.01~1g。
通常通过用水将乳剂、水合剂、流动剂等稀释并喷洒来进行处理。此时,本哒嗪化合物及本化合物(A)的浓度以本哒嗪化合物及本化合物(A)的合计的浓度计通常为0.0005~2重量%,优选为0.005~1重量%。通常不将粉剂、粒剂等稀释而直接进行处理。
实施例
以下,通过制剂例及试验例进一步详细说明本发明,但本发明不仅限于以下的例子。需要说明的是,在以下的例子中,份没有特别说明就表示重量份。
首先,进一步详细说明本发明组合物中使用的本哒嗪化合物的参考制造例,但本发明不限于这些例子。
参考制造例1
在2-溴苯丙酮2.13g、2,6-二氟苯基乙酸1.81g及乙腈25ml的混合物中在水浴下滴入三乙胺1.52g,在室温下搅拌4小时后,静置一晩。在该混合物中在冰浴冷却下滴入1,8-二氮杂双环[5.4.0]-7-十一碳烯(以下,记为DBU)4.57g。将该混合物在室温下搅拌1小时。之后,在得到的混合物中在室温下边搅拌边吹入5小时空气。在反应混合物中加入冰及1摩尔/L盐酸,用乙酸乙酯萃取。用饱和小苏打水溶液及饱和食盐水依次洗涤有机层,用无水硫酸镁干燥后,在减压下浓缩,得到3-(2,6-二氟苯基)-5-羟基-5-甲基-4-苯基-2(5H)-呋喃酮2.83g。
1H-NMR(CDCl3,TMS)δ(ppm):1.78(3H,s),4.07(1H,br s),6.77-6.85(1H,br m),6.96-7.08(1H,m),7.29-7.38(4H,m),7.53-7.55(2H,m)
在3-(2,6-二氟苯基)-5-羟基-5-甲基-4-苯基-2(5H)-呋喃酮2.83g及1-丁醇15ml的混合物中滴入肼一水合物0.60g后,在浴温110℃搅拌2小时30分钟。接着,将反应混合物冷却至0℃。通过过滤得到的固体而进行了收集。将收集的固体用己烷及叔丁基甲基醚的混合溶剂(1:1)洗涤,在减压下干燥,得到4-(2,6-二氟苯基)-6-甲基-5-苯基-2H-哒嗪-3-酮1.70g。
1H-NMR(DMSO-d6,TMS)δ(ppm):2.02(3H,s),6.92-6.98(2H,m),7.11-7.12(2H,m),7.27-7.36(4H,m),13.2(1H,br s)
将4-(2,6-二氟苯基)-6-甲基-5-苯基-2H-吡啶-3-酮1.54g及氧氯化磷10ml混合,在浴温110℃搅拌1小时30分钟。将反应混合物放置冷却至室温后在减压下浓缩。在残渣中加入乙酸乙酯和冰水,分液。用饱和小苏打水溶液及饱和食盐水依次洗涤有机层,用无水硫酸钠干燥后,在减压下浓缩。将得到的残渣1.55g用己烷及乙酸乙酯的混合液(10:1)、再用叔丁基甲基醚洗涤,得到本哒嗪化合物(1)0.85g。
1H-NMR(CDCl3,TMS)δ(ppm):2.55(3H,s),6.79-6.83(2H,m),7.07-7.09(2H,m),7.23-7.30(4H,m)
参考制造例2
将4-(2,6-二氟苯基)-6-甲基-5-苯基-2H-吡啶-3-酮2.09g及氧溴化磷8.0g混合,在90℃搅拌1小时30分钟。将反应混合物放置冷却至室温后使其在乙酸乙酯20ml中悬浊,注加到冰约100g中。用小苏打中和后,用乙酸乙酯萃取残渣,分液。水洗有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(2.00g)供于硅胶柱色谱法,以固体的形式得到本哒嗪化合物(2)1.12g。
1H-NMR(CDCl3,TMS)δ(ppm):2.52(3H,s),6.78-6.84(2H,m),7.06-7.09(2H,m),7.22-7.30(4H,m)
将本哒嗪化合物(2)0.80g、氰化铜0.33g及N,N-二甲基乙酰胺10ml混合,在加热回流下搅拌3小时。将反应混合物放置冷却至室温后加入至乙酸乙酯及水各100ml中,进行celite(注册商标)过滤。将滤液分液,用食盐水洗涤有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(0.61g)供于硅胶柱色谱法,以白色固体的形式得到本哒嗪化合物(3)0.40g。
1H-NMR(CDCl3,TMS)δ(ppm):2.70(3H,s),6.86-6.90(2H,m),7.07-7.09(2H,m),7.30-7.38(4H,m)
参考制造例3
将本哒嗪化合物(1)0.95g、乙酰丙酮铁(III)0.21g、四氢呋喃30ml及N-甲基吡咯烷酮3ml混合,向其中在冰浴冷却下边搅拌边加入甲基溴化镁(3.0摩尔/L乙醚溶液)3ml。在冰浴冷却下,搅拌1小时后,在反应混合物中滴入0.33摩尔/L盐酸水溶液15ml,加入水后,用乙酸乙酯萃取。水洗有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(0.91g)供于硅胶柱色谱法,以白色晶体的形式得到本哒嗪化合物(4)0.82g。
1H-NMR(CDCl3,TMS)δ(ppm):2.51(3H,s),2.52(3H,s),6.74-6.82(2H,m),7.05-7.07(2H,m),7.18-7.30(4H,m)
参考制造例4
将6-甲基-5-苯基-4-(2,4,6-三氟苯基)-2H-吡啶-3-酮2.21g及氧溴化磷8.0g混合,在90℃搅拌1小时30分钟。将反应混合物放置冷却至室温后使其在乙酸乙酯20ml中悬浊,注加到冰100g中。用小苏打中和后,用乙酸乙酯萃取残渣,分液。用食盐水洗涤有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(2.42g)供于硅胶柱色谱法,以白色固体的形式得到本哒嗪化合物(6)1.86g。
1H-NMR(CDCl3,TMS)δ(ppm):2.52(3H,s),6.56-6.64(2H,m),7.05-7.07(2H,m),7.30-7.36(3H,m)
将本哒嗪化合物(6)1.26g、氰化铜0.44g及N,N-二甲基乙酰胺14ml混合,在加热回流下搅拌3小时。将反应混合物放置冷却至室温后加入至乙酸乙酯及水各100ml中,进行celite(注册商标)过滤。
将滤液分液,用食盐水洗涤有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(1.07g)供于硅胶柱色谱法,以淡黄色固体的形式得到本哒嗪化合物(7)0.55g。
1H-NMR(CDCl3,TMS)δ(ppm):2.70(3H,s),6.63-6.69(2H,m),7.06-7.09(2H,m),7.34-7.40(3H,m)
参考制造例5
将按照在国际公开第2005/121104号小册子中记载的方法制造的本哒嗪化合物(5)1.00g、乙酰丙酮铁(III)0.21g、四氢呋喃30ml及N-甲基吡咯烷酮3ml混合,向其中在冰浴冷却下,边搅拌边加入甲基溴化镁(3.0摩尔/L乙醚溶液)3ml。冰浴冷却下,搅拌1小时后,在反应混合物中滴入0.33摩尔/L盐酸水溶液15ml,加入水后,用乙酸乙酯萃取。水洗有机层,用无水硫酸镁干燥后,在减压下浓缩。将得到的残渣(0.98g)供于硅胶柱色谱法,以白色晶体的形式得到本哒嗪化合物(8)0.82g。
1H-NMR数据与在WO2006/001175A1中记载的数据大致一致。
制剂例1
通过将本哒嗪化合物(1)~(8)中任一种2.5份、本化合物(A)1.25份、聚氧亚乙基苯乙烯基苯基醚14份、十二烷基苯磺酸钙6份及二甲苯76.25份充分混合,由此得到各制剂。
制剂例2
通过将本哒嗪化合物(1)~(8)中任一种2份、本化合物(A)8份、白炭与聚氧亚乙基烷基醚硫酸铵盐的混合物(重量比例1:1)35份及水55份混合,用湿式粉碎法微粉碎,由此得到各制剂。
制剂例3
将本哒嗪化合物(1)~(8)中任一种5份、本化合物(A)10份、含有失水山梨醇三油酸酯1.5份及聚乙烯醇2份的水溶液28.5份混合,用湿式粉碎法微粉碎后,在其中加入含有黄原胶0.05份及硅酸铝镁0.1份的水溶液45份,进一步加入丙二醇10份并搅拌混合而得到各制剂。
制剂例4
将本哒嗪化合物(1)~(8)中任一种1份、本化合物(A)4份、合成含水氧化硅1份、木质素磺酸钙2份、膨润土30份及高岭土62份充分粉碎混合,加入水并混炼后,进行造粒干燥,由此得到各制剂。
制剂例5
将本哒嗪化合物(1)~(8)中任一种12.5份、本化合物(A)37.5份、木质素磺酸钙3份、月桂基硫酸钠2份及合成含水氧化硅45份充分粉碎混合,由此得到各制剂。
制剂例6
将本哒嗪化合物(1)~(8)中任一种3份、本化合物(A)2份、高岭土85份及滑石10份充分粉碎混合,由此得到制剂。
下面示出试验例。需要说明的是,在试验例中使用的式(A)所示的化合物使用了外消旋混合物。
试验例1
在塑料盆中装入土壤,播种小麦(品种;Apogee(アポジー)),在温室内使其生长14天。将供试化合物溶解于CEC混合物(环己酮:ソルポール(注册商标)2680X(东邦化学工业制)=5:1(体积比))并制剂后,用水稀释而设置为规定浓度,以将该稀释液充分附着于上述小麦的叶面的方式进行了茎叶喷洒。将喷洒后植物风干,在2天后喷雾接种小麦叶枯病菌(Mycosphaerella graminicola)的分生孢子的水悬浊液(约1,000,000个/ml)。接种后首先在18℃多湿条件下放置3天,从多湿条件下移出后在18℃恒温室中栽培14天(将其作为处理区。)。之后,调查了小麦叶枯病的病斑面积。另一方面,除了不用供试化合物的稀释液进行茎叶喷洒以外与处理区同样地栽培了小麦(将其作为无处理区。)。与处理区同样地调査了小麦叶枯病的病斑面积。
由处理区及无处理区分别的病斑面积通过下述式(1)求出处理区的效力。在表[1]及表[2]中示出其结果。
[表1]
[表2]
试验例2
用旋转式种子处理机(seed dresser,Hans-Ulrich Hege GmbH制)对自然感染了红色雪腐病菌(Microdochium nivale)的孢子的小麦(品种;シロガネ)种子10g涂沫处理了含有规定重量的供试化合物的环己酮溶液100μl。
自上述处理1天后,在塑料盆中装入土壤,播种用供试化合物进行处理后的种子,在玻璃温室下栽培20天(将其作为处理区)。之后,观察从各种子出芽的苗中的红色雪腐病的发病的有无,通过下述式(2)求出发病率。
另一方面,使用未进行上述的涂沫处理的小麦种子,与处理区同样地栽培(将其作为无处理区。)。然后与处理区同样地求出发病率。
由处理区及无处理区各自的发病率,通过下述式(3)求出处理区的效力。
在表[3]及表[4]中显示其结果。
[表3]
[表4]
产业上的可利用性
根据本发明,能防除植物病害。
Claims (5)
1.一种植物病害防除组合物,其含有式(I)所示的哒嗪化合物和下述式(A)所示的化合物,
式(I)中,
R1表示氯原子、溴原子、氰基或甲基,
R2表示氢原子或氟原子,
式(A):
2.根据权利要求1所述的植物病害防除组合物,其中,
哒嗪化合物与式(A)所示的化合物的重量比为哒嗪化合物/式(A)所示的化合物=0.1/1~10/1。
3.一种植物病害防除方法,其包含用式(I)所示的哒嗪化合物和下述式(A)所示的化合物的有效量对植物或栽培植物的土壤进行处理的工序,
式(I)中,
R1表示氯原子、溴原子、氰基或甲基,
R2表示氢原子或氟原子,
式(A):
4.根据权利要求3所述的植物病害防除方法,其中,
哒嗪化合物与式(A)所示的化合物的重量比为哒嗪化合物/式(A)所示的化合物=0.1/1~10/1。
5.根据权利要求3或4所述的植物病害防除方法,其中,
植物或栽培植物的土壤为小麦或栽培小麦的土壤。
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JP2012161708A JP2014019680A (ja) | 2012-07-20 | 2012-07-20 | 植物病害防除組成物およびその用途 |
PCT/JP2013/067158 WO2014013841A1 (ja) | 2012-07-20 | 2013-06-18 | 植物病害防除組成物およびその用途 |
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CN110024793A (zh) * | 2019-05-14 | 2019-07-19 | 东莞东阳光科研发有限公司 | 一种含有Pyridachlometyl和噻菌腈的组合物 |
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CN107920524B (zh) * | 2015-08-11 | 2020-07-24 | 住友化学株式会社 | 植物病害防治组合物和植物病害防治方法 |
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FR3048331B1 (fr) * | 2016-03-04 | 2018-05-04 | Sumitomo Chemical Company, Limited | Pesticide liquide contenant un compose de pyridazine et procede de maitrise des maladies des plantes l'utilisant |
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TWI489941B (zh) * | 2008-09-19 | 2015-07-01 | Sumitomo Chemical Co | 種子處理劑及保護植物的方法 |
AR076696A1 (es) * | 2009-05-25 | 2011-06-29 | Sumitomo Chemical Co | Composicion y metodo para controlar enfermedades de plantas |
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CN1394846A (zh) * | 1994-04-06 | 2003-02-05 | 盐野义制药株式会社 | α-取代苯乙酸衍生物,它的制备及含有该化合物的农用杀菌剂 |
EP1775290A1 (en) * | 2004-06-28 | 2007-04-18 | Sumitomo Chemical Company, Limited | Pyridazine compound and use thereof |
WO2011108763A2 (en) * | 2010-03-03 | 2011-09-09 | Sumitomo Chemical Company, Limited | Plant disease controlling composition and method for controlling plant disease |
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