CN1933731A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
- Publication number
- CN1933731A CN1933731A CNA2005800092002A CN200580009200A CN1933731A CN 1933731 A CN1933731 A CN 1933731A CN A2005800092002 A CNA2005800092002 A CN A2005800092002A CN 200580009200 A CN200580009200 A CN 200580009200A CN 1933731 A CN1933731 A CN 1933731A
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- CN
- China
- Prior art keywords
- compound
- mixture
- alkyl
- formula
- methyl
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
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- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 1
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- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
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- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
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- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229910001432 tin ion Inorganic materials 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明涉及杀真菌混合物,该混合物含有协同有效量的1)式I的三唑并嘧啶衍生物和2)式II的酰替苯胺作为活性组分,其中各变量具有下列含义:Ar为苯基或含有1-4个选自O、N和S的杂原子的5或6员芳族杂环,其中该环未被取代或可以被1-3个基团R1取代;R1为卤素、烷基或卤代烷基;R为苯基、烷基、卤代烷基、烷氧基、卤代烷氧基;Q为氢、烷基、卤代烷基、烷氧基、卤代烷氧基。本发明还涉及使用化合物I和化合物II的混合物防治病原性真菌的方法、化合物I和化合物II在生产该类混合物中的用途以及含有该类混合物的组合物。
Description
本发明涉及杀真菌混合物,所述混合物包含协同有效量的如下化合物作为活性组分:
1)式I的三唑并嘧啶衍生物:
和
2)式II的酰替苯胺(anilide):
其中各变量如下所定义:
Ar为苯基或含有1-4个选自O、N和S的杂原子的5或6员芳族杂环,其中该环未被取代或可以被1-3个基团R1取代:
R1为卤素、C1-C4烷基或C1-C4卤代烷基;
R为苯基、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基;
Q为氢、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基。
此外,本发明还涉及一种使用化合物I与化合物II的混合物防治有害真菌的方法,化合物I和化合物II在制备该类混合物中的用途以及包含这些混合物的组合物。
化合物I,即5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,其制备及其对有害真菌的作用由文献(WO 98/46607)已知。
化合物II,其制备及其对有害真菌的作用同样由文献(JP 10130268)已知。
三唑并嘧啶与其他活性化合物的混合物以一般方式由EP-A 988 790和US 6 268 371已知。
化合物II与其他活性化合物的混合物例如由JP 11228309、JP2000053506和JP 2001072513已知。
为了降低已知化合物的施用率并拓宽其活性谱,本发明的目的是提供在活性化合物的施用总量降低下对有害真菌具有改进活性的混合物(协同增效混合物)。
我们发现该目的通过开头定义的混合物实现。此外,我们发现与施用单一化合物可能产生的效果相比,同时,即联合或分开施用化合物I和化合物II之一或者依次施用化合物I和化合物II之一能够更好地防治有害真菌。
化合物I和化合物II的混合物或化合物I和化合物II的同时,即联合或分开使用对宽范围的植物病原性真菌,尤其是选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、卵菌纲(Oomycetes)和担子菌纲(Basidiomycetes)的真菌具有高度活性。它们可以作为叶面作用杀真菌剂和土壤作用杀真菌剂用于作物保护中。
它们对在各种栽培植物如香蕉、棉花、蔬菜品种(例如黄瓜、豆类和葫芦科植物)、大麦、禾草、燕麦、咖啡、土豆、玉米、水果品种、稻、黑麦、大豆、西红柿、葡萄藤、小麦、观赏植物、甘蔗以及大量种子中防治大量真菌尤其重要。
它们特别适于防治下列植物病原性真菌:禾谷类上的禾白粉菌(Blumeria graminis)(白粉病),葫芦科植物上的二孢白粉菌(Erysiphecichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),苹果上的苹果白粉病菌(Podosphaera leucotricha),葡萄藤上的葡萄钩丝壳(Uncinula necator),禾谷类上的柄锈菌(Puccinia)属,棉花、稻和草坪上的丝核菌(Rhizoctonia)属,禾谷类和甘蔗上的黑粉菌(Ustilago)属,苹果上的黑星病菌(Venturiainaequalis),禾谷类、稻和草坪中的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属,小麦上的颖枯壳针孢(Septoria nodorum),草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea),香蕉、花生和禾谷类上的球腔菌(Mycosphaerella)属,小麦和大麦上的眼斑病菌(Pseudocercosporellaherpotrichoides),稻上的稻瘟病菌(Pyricularia oryzae),土豆和西红柿上的致病疫霉(Phytophthora infestans),葫芦科植物和啤酒花上的假霜霉(Pseudoperonospora)属,葡萄藤上的葡萄生单轴霉(Plasmopara viticola),蔬菜和水果上的链格孢(Alternaria)属,以及链孢霉(Fusarium)属和轮枝孢(Verticillium)属。
它们还可用于保护材料(如保护木材)以例如防治拟青霉(Paecilomycesvariotii)。
化合物I和化合物II可以同时,即联合或分开施用,或依次施用,在分开施用的情况下,施用顺序通常对防治措施的结果没有任何影响。
在对式II所给变量的定义中,使用通常为下列取代基的代表的集合性术语:
卤素:氟、氯、溴和碘;
烷基:具有1-4、1-6或1-8个碳原子的饱和直链或支化烃基,例如C1-C6烷基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基;
卤代烷基:具有1-2、1-4、1-6或1-8个碳原子的直链或支化烷基(如上所述),其中这些基团中的部分或所有氢原子可以被上述卤原子替换,尤其是C1-C2卤代烷基如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基或1,1,1-三氟丙-2-基;
-含有1-4个氮原子或1-3个氮原子和1个硫或氧原子的5员杂芳基:除了碳原子外可以含有1-4个氮原子或1-3个氮原子和1个硫或氧原子作为环成员的5员杂芳基,例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基和1,3,4-三唑-2-基;
-含有1-3或1-4个氮原子的6员杂芳基:除了碳原子外可以含有1-3或1-4个氮原子作为环成员的6员杂芳基,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基和2-吡嗪基。
本发明的范围包括具有手性中心的式I化合物的(R)和(S)异构体以及外消旋体。
考虑到化合物II的意欲用途,特别优选取代基的下列含义,在每种情况下单独或结合:
Ar优选为苯基或5员芳族杂环,尤其是未取代或被1或2个基团R1取代的5员杂芳基。
此外,Ar优选为下列基团之一:苯基、吡啶基、吡嗪基、呋喃基、噻吩基、吡唑基和噻唑基。特别优选的基团Ar为3-吡啶基、吡嗪基、3-呋喃基、3-噻吩基、4-吡唑基、5-噻唑基。
基团R1特别优选位于酰胺基团的邻位。
优选的基团R1为卤素,尤其是氯,烷基,尤其是甲基,以及卤代甲基,尤其是氟甲基、二氟甲基或三氟甲基。
优选的基团R为烷基,尤其是支化C3-C8烷基,尤其是4-甲基戊-2-基。
适于与化合物I混合使用的尤其是下列式II化合物:
若在式中存在两个基团R1,则这些基团可以相同或不同。
特别优选的是化合物IIA,尤其是式IIA.1和IIB.1化合物,其中R1可以相同或不同且为甲基和卤代甲基以及R为烷基,如支化C3-C8烷基,尤其是4-甲基戊-2-基:
尤其优选以其R和S异构体形式存在的化合物IIA.11(通用名:吡噻菌胺(penthiopyrad))和IIB.11:
由于其氮原子的碱性特征,化合物I和II能够与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例是氢卤酸,如氟化氢、氯化氢、溴化氢和碘化氢,硫酸,磷酸和硝酸。
合适的有机酸例如为甲酸,碳酸和链烷酸,如乙酸、三氟乙酸、三氯乙酸和丙酸,还有羟基乙酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸和2-乙酰氧基苯甲酸。
合适的金属离子尤其是第1-8过渡族元素的离子,尤其是铬离子、锰离子、铁离子、钴离子、镍离子、铜离子、锌离子,此外还有第2主族元素的离子,尤其是钙离子和镁离子,以及第3和4主族元素的离子,尤其是铝离子、锡离子和铅离子。合适的话,金属离子可以它们可能呈现的各种价态存在。
当制备混合物时,优选使用纯活性化合物I和II,可以根据需要向其中加入其它对抗有害真菌或其它害虫如昆虫、蜘蛛或线虫的活性化合物,或除草或生长调节活性化合物或肥料。
其它在上述意义上合适的活性化合物尤其为选自如下的杀真菌剂:
·酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、霜灵(oxadixyl),
·胺衍生物,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺茂胺(spifoxamine)、克啉菌(tridemorph),
·苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil),
·抗菌素,例如放线菌酮(cycloheximid)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin),
·唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、烯菌灵(enilconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizol)、戊叉唑菌(triticonazole),
·二羧酰亚胺类,如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)、烯菌酮(vinclozolin),
·二硫代氨基甲酸盐类,如福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)、代森锌(zineb),
·杂环化合物,如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolan)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、picobenzamid、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamid)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine),
·铜杀真菌剂,如波尔多液(Bordeaux混合物)、醋酸铜、王铜、碱式硫酸铜,
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthal-isopropyl),
·苯基吡咯类,如拌种咯(fenpiclonil)或氟菌(fludioxonil),
·硫,
·其它杀真菌剂,如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、哒菌清(diclomezin)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、亚磷酸、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenon)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)、苯酰菌胺(zoxamid),
·嗜球果伞素类(strobilurin),如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)或肟菌酯(trifloxystrobin),
·次磺酸衍生物,如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)、对甲抑菌灵(tolylfluanid),
·肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
在本发明混合物的一个实施方案中,向化合物I和II中加入另一杀真菌剂III或两种杀真菌剂III和IV。
优选化合物I和II以及组分III的混合物。特别优选化合物I和II的混合物。
化合物I和化合物II通常以100∶1-1∶100,优选20∶1-1∶20,尤其是10∶1-1∶10的重量比使用。
需要的话,组分III以及合适的话组分IV以20∶1-1∶20的比例加入化合物I中。
取决于化合物的种类和所需效果,本发明混合物的施用率为5-1000g/ha,优选50-900g/ha,尤其是50-750g/ha。
相应地,化合物I的施用率通常为1-1000g/ha,优选10-900g/ha,尤其是20-750g/ha。
相应地,化合物II的施用率通常为1-1000g/ha,优选10-500g/ha,尤其是40-350g/ha。
在种子处理中,混合物的施用率通常为1-1000g/100kg种子,优选1-200g/100kg,尤其是5-100g/100kg。
防治有害真菌的方法通过在植物播种之前或之后或在植物出苗之前或之后对种子、植物或土壤喷雾或撒粉而分开或联合施用化合物I和化合物II或化合物I和化合物II的混合物而进行。它们优选通过喷雾叶子而施用。
可将本发明的混合物或化合物I和II转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的目的;在每种情况下,应确保本发明化合物精细且均匀地分布。
配制剂以已知方式制备,例如通过将活性化合物与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。适于该目的的溶剂/助剂主要为:
-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
所用的合适表面活性剂为木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化异辛基酚,辛基酚,壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质为中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或一起研磨来制备。
颗粒如涂敷颗粒、浸渍颗粒和均质颗粒可以通过使活性化合物与固体载体粘附而制备。固体载体实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。活性化合物以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.用水稀释的产品
A)水溶性浓缩物(SL)
将10重量份活性化合物溶于水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于环己酮中并加入分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。
C)乳油(EC)
将15重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。用水稀释得到乳液。
D)乳液(EW,EO)
将40重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。借助乳化机(Ultraturrax)将该混合物引入水中并制成均相乳液。用水稀释得到乳液。
E)悬浮液(SC,OD)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入分散剂、湿润剂和水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。
F)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份活性化合物细碎研磨并加入分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。
G)水分散性粉末和水溶性粉末(WP,SP)
将75重量份活性化合物在转子-定子磨机中研磨并加入分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。
2.不经稀释而施用的产品
H)可撒粉粉末(DP)
将5重量份活性化合物细碎研磨并与95%的细碎高岭土充分混合。这得到可撒粉产品。
I)颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合95.5%载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的颗粒。
J)ULV溶液(UL)
将10重量份活性化合物溶于有机溶剂如二甲苯中。这得到不经稀释而施用的产品。
活性化合物可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒形式),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;它们意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物也可成功用于超低容量法(ULV),其中可以施用包含超过95重量%活性化合物的配制剂,或甚至施用不含添加剂的活性化合物。
各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂都可加入活性化合物中,若合适的话,恰在紧邻使用前加入(桶混合)。这些试剂通常与本发明组合物以1∶10-10∶1的重量比混合。
化合物I和II或混合物或对应的配制剂通过用杀真菌有效量的混合物,或在分开施用的情况下化合物I和II处理有害真菌或需要防治它们的植物、种子、土壤、区域、材料或空间而施用。施用可以在有害真菌侵染之前或之后进行。
化合物和混合物的杀真菌作用可以通过下列试验证实:
使用溶剂/乳化剂体积比为99∶1的丙酮和/或DMSO和乳化剂Uniperol EL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)的混合物将活性化合物单独或联合制备成10ml包含25mg活性化合物的储备溶液。然后将该混合物用水配成100ml。将该储备溶液用所述溶剂/乳化剂/水混合物稀释至下述活性化合物浓度。或者将活性化合物以市售的最终配制剂使用并用水稀释至给定的活性化合物浓度。
应用实施例—对由网斑病菌(Pyrenophora teres)引起的大麦网斑病的活性,5天保护性施用
将盆栽大麦秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。施用5天后,将试验植物用网斑病菌(Pyrenophora[同义词Drechslera]teres)—网斑病病原体的含水孢子悬浮液接种。然后将试验植物放入温度为20-24℃且相对大气湿度为95-100%的温室中。6天后以整个叶面积的侵染%肉眼测定病害的发展程度。
将肉眼测定的侵染叶面积百分数转化为效力,以相对于未处理对照的百分数表示:
使用Abbot公式按如下计算效力(E):
E=(1-α/β)·100
α对应于处理植物的真菌侵染百分数,和
β对应于未处理(对照)植物的真菌侵染百分数。
效力为0表示处理植物的侵染水平相当于未处理的对照植物;效力为100表示处理植物未受侵染。
活性化合物的混合物的预期效力使用Colby公式(Colby S.R.,“计算除草剂组合的协同增效和拮抗响应”,Weeds(杂草),15,20-22,1967)确定并与观察到的效力比较。
Colby公式:E=x+y-x·y/100
E使用浓度为a和b的活性化合物A和B的混合物时的预期效力,以相对于未处理对照的%表示,
x使用浓度为a的活性化合物A时的效力,以相对于未处理对照的%表示,y使用浓度为b的活性化合物B时的效力,以相对于未处理对照的%表示。
表A-单独的活性化合物
实施例 | 活性化合物/混合比 | 活性化合物在喷雾液中的浓度[ppm] | 效力,相对于未处理对照的% |
1 | 对照(未处理) | - | (90%侵染) |
2 | I | 410.25 | 3300 |
3 | IIA.11 | 410.25 | 56330 |
表B-本发明混合物
实施例 | 活性化合物的混合物浓度混合比 | 观察的效力 | 计算的效力*) |
4 | I+II.A.114+1ppm4∶1 | 94 | 56 |
5 | I+II.A.114+4ppm1∶1 | 97 | 70 |
6 | I+II.A.111+1ppm1∶1 | 78 | 33 |
7 | I+II.A.111+4ppm1∶4 | 94 | 56 |
8 | I+II.A.110.25+1ppm1∶4 | 56 | 33 |
*)使用Colby公式计算的效力
试验结果表明,由于强协同增效作用,本发明混合物在所有混合比下的活性显著高于使用Colby公式预测的活性。
Claims (11)
1.一种用于防治植物病原性有害真菌的杀真菌混合物,该混合物包含协同有效量的如下化合物:
1)式I的三唑并嘧啶衍生物:
和
2)式II的酰替苯胺:
其中各变量如下所定义:
Ar为苯基或含有1-4个选自O、N和S的杂原子的5或6员芳族杂环,其中该环未被取代或可以被1-3个基团R1取代:
R1为卤素、C1-C4烷基或C1-C4卤代烷基;
R为苯基、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基;
Q为氢、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基。
2.根据权利要求1的杀真菌混合物,包含式IIA.1或IIB.1化合物作为酰替苯胺:
其中R1在每种情况下可以相同或不同且为甲基或卤代甲基以及R为烷基。
4.根据权利要求1-3中任一项的杀真菌混合物,以100∶1-1∶100的重量比包含式I化合物和式II化合物。
5.一种组合物,包含液体或固体载体和根据权利要求1-4中任一项的混合物。
6.一种防治植物病原性有害真菌的方法,其包括用有效量的根据权利要求1的化合物I和化合物II处理真菌、其栖息地或需要防止真菌侵袭的植物、土壤或种子。
7.根据权利要求6的方法,其中同时,即联合或分开,或依次施用根据权利要求1的化合物I和II。
8.根据权利要求6或7的方法,其中以5-1000g/ha的量施用根据权利要求1的化合物I和II或根据权利要求1-4中任一项的混合物。
9.根据权利要求5-7中任一项的方法,其中以1-1000g/100kg种子的量施用根据权利要求1的化合物I和II或根据权利要求1-4中任一项的混合物。
10.种子,包含1-1000g/100kg根据权利要求1-4中任一项的混合物。
11.根据权利要求1的化合物I和II在制备适于防治有害真菌的组合物中的用途。
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