CN101400259B - 引发植物对细菌病害耐受性的方法 - Google Patents
引发植物对细菌病害耐受性的方法 Download PDFInfo
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- CN101400259B CN101400259B CN2007800092270A CN200780009227A CN101400259B CN 101400259 B CN101400259 B CN 101400259B CN 2007800092270 A CN2007800092270 A CN 2007800092270A CN 200780009227 A CN200780009227 A CN 200780009227A CN 101400259 B CN101400259 B CN 101400259B
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- 235000011941 Tilia x europaea Nutrition 0.000 description 1
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- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
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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
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-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
- A01N37/36—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
- 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
- A01N37/38—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 having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
-
- 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
- A01N43/34—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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Cultivation Of Plants (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及一种引发植物对细菌病害耐受性的方法,其包括用有效量的式I化合物,其中变量具有说明书所述的含义,与如说明书所定义的第二种活性化合物的组合处理植物、土壤或种子,其被植物或种子吸收。
Description
本发明涉及一种引发植物对细菌病害耐受性的方法,其包括用有效量的如下化合物处理植物、土壤或种子:
1)式I化合物:
其中:
X为卤素、C1-C4烷基或三氟甲基;
m为0或1;
Q为C(=CH-CH3)-COOCH3、C(=CH-OCH3)-COOCH3、C(=N-OCH3)-CONHCH3、C(=N-OCH3)-COOCH3、N(-OCH3)-COOCH3或基团Q1:
其中#表示与苯环相连的键;
A为-O-B、-CH2O-B、-OCH2-B、-CH=CH-B、-C≡C-B、-CH2O-N=C(R1)-B、-CH2O-N=C(R1)-CH=CH-B或-CH2O-N=C(R1)-C(R2)=N-OR3,其中:
B为苯基、萘基、含1-3个N原子和/或1个O或S原子或1或2个O和/或S原子的5元或6元杂芳基或5元或6元杂环基,其中环体系未被取代或由1-3个基团Ra取代:
Ra为氰基、硝基、氨基、氨基羰基、氨基硫代羰基、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基羰基、C1-C6烷基磺酰基、C1-C6烷基亚磺酰基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧羰基、C1-C6烷硫基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基、C1-C6烷基氨基硫代羰基、二-C1-C6烷基氨基硫代羰基、C2-C6链烯基、C2-C6链烯氧基、苯基、苯氧基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基、C(=NORa)-Rb或OC(Ra)2-C(Rb)=NORb,
其中环状基团也未被取代或由1-3个基团Rb取代:
Rb为氰基、硝基、卤素、氨基、氨基羰基、氨基硫代羰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基磺酰基、C1-C6烷基亚磺酰基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧羰基、C1-C6烷硫基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基、C1-C6烷基氨基硫代羰基、二-C1-C6烷基氨基硫代羰基、C2-C6链烯基、C2-C6链烯氧基、C3-C6环烷基、C3-C6环烯基、苯基、苯氧基、苯硫基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基或C(=NORA)-RB;RA、RB为氢或C1-C6烷基;
R1为氢、氰基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C1-C4烷氧基;
R2为苯基、苯基羰基、苯基磺酰基、5或6元杂芳基、5或6元杂芳基羰基或5或6元杂芳基磺酰基,其中环体系未被取代或由1-3个基团Ra取代,
C1-C10烷基、C3-C6环烷基、C2-C10链烯基、C2-C10炔基、C1-C10烷基羰基、C2-C10链烯基羰基、C3-C10炔基羰基、C1-C10烷基磺酰基或C(=NORA)-RB,其中这些基团的烃基未被取代或由1-3个基团Rc取代:
Rc为氰基、硝基、氨基、氨基羰基、氨基硫代羰基、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基磺酰基、C1-C6烷基亚磺酰基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧羰基、C1-C6烷硫基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷基氨基羰基、二-C1-C6烷基氨基羰基、C1-C6烷基氨基硫代羰基、二-C1-C6烷基氨基硫代羰基、C2-C6链烯基、C2-C6链烯氧基、C3-C6环烷基、C3-C6环烷氧基、5或6元杂环基、5或6元杂环基氧基、苄基、苄氧基、苯基、苯氧基、苯硫基、5或6元杂芳基、5或6元杂芳氧基和杂芳基硫基,环状基团也可部分或完全被卤化或1-3个基团Ra连在其上;和
R3为氢、C1-C6烷基、C2-C6链烯基、C2-C6炔基,其中这些基团的烃基未被取代或由1-3个基团Rc取代;
和
2)选自组A)-M)的化合物:
A)酰基丙氨酸类:苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl);
B)胺衍生物: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)、螺噁茂胺(spiroxamine)、克啉菌(tridemorph);
C)苯胺基嘧啶类:二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil);
D)唑类:双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、噁醚唑(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(triflumizole)、戊叉唑菌(triticonazole),
E)二羧酰亚胺类:异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)、烯菌酮(vinclozolin),
F)二硫代氨基甲酸盐类: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),
G)杂环化合物: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)、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(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、吡噻菌胺(penthiopyrad)、氟吡菌胺(picobenzamid)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquiln)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine)、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、4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-溴-联苯-2-基)-酰胺、4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-三氟甲基-联苯-2-基)-酰胺、4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-氯-3’-氟-联苯-2-基)-酰胺、3-二氟甲基-1-甲基-吡唑-4-甲酸-(3’,4’-二氯-4-氟-联苯-2-基)-酰胺、3-二氟甲基-1-甲基-吡唑-4-甲酸-(3’,4’-二氯-5-氟-联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′-二氯联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,5′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,5′-二氯联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,5′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,5′-二氯联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′-氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′-氯联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′-氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′-氯联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,4′,5′-三氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′,5′-三氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸[2-(1,1,2,3,3,3-六氟丙氧基)-苯基]-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸[2-(1,1,2,2-四氟乙氧基)-苯基]-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(4′-三氟甲基硫代联苯-2-基)-酰胺、N-(2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺、3,4-二氯-异噻唑-5-甲酸(2-氰基-苯基)酰胺、3-[5-(4-氯-苯基)-2,3-二甲基-异噁唑烷-3-基]-吡啶、2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮、3-(3-溴-6-氟-2-甲基-吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酸二甲基酰胺、(2-氯-5-[1-(3-甲基-苄基氧基亚氨基)-乙基]-苄基)-氨基甲酸甲基酯、(2-氯-5-[1-(6-甲基-吡啶-2-基甲氧基亚氨基)-乙基]-苄基)-氨基甲酸甲基酯,
H)硫,
I)硝基苯基衍生物:乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthal-isopropyl),
J)苯基吡咯类:拌种咯(fenpiclonil)或氟噁菌(fludioxonil),
K)其它杀真菌剂,选自噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、哒菌清(diclomezine)、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)、亚磷酸及其盐、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、双炔酰菌胺(mandipropamid)、苯菌酮(metrafenone)、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(zoxamide)、乙酰基水杨酸(acetyl salic acid)、N-(2-(4-[3-(4-氯-苯基)-丙-2-炔基氧基]-3-甲氧基-苯基)-乙基)-2-甲烷磺酰基氨基-3-甲基-丁酰胺、N-(2-(4-[3-(4-氯-苯基)-丙-2-炔基氧基]-3-甲氧基-苯基)-乙基)-2-乙烷磺酰基氨基-3-甲基-丁酰胺、3-(4-氯-苯基)-3-(2-异丙氧基羰基氨基-3-甲基-丁酰基氨基)-丙酸甲基酯,
L)次磺酸衍生物:敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)、对甲抑菌灵(tolylfluanid),和
M)肉桂酰胺及类似化合物:烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
其中组分1)和2)被植物或种子吸收。另外,本发明通常涉及式I化合物与组A)-M)的化合物的组合在使植物对细菌病害免疫中的用途。
细菌作为大量作物植物病害的病原体(细菌病害)主要发现于温和和潮湿温暖气候区中。有时这些病害导致极大经济损害。通常已知的实例为由欧文氏菌(Erwinia)属变体导致的整个水果种植园的死亡(梨和苹果的“梨火疫病”),马铃薯和许多其他植物的细菌性软腐病,农杆菌(agrobacteria)引发的各种植物瘤,由黄单孢菌(Xanthomonas)属导致的各种蔬菜、稻、小麦和柑橘果实的坏死。蔬菜、顶果属和烟草中由假单胞菌(Pseudomonas)属导致的细菌病害尤其可怕。
如可预期的,参加真菌特异性代谢过程的常规杀真菌剂对细菌病害不具有活性。因此,目前为止,可能防治它们的仅有途径是使用抗生素(例如链霉素(streptomycin)、稻瘟散S(Blasticidin S)或春雷霉素(Kasugamicin)),但此方法很少实践:由于原则上这些抗生素依赖与人类和兽医学中对抗细菌性病原体相同的作用机理,在农业中广泛应用抗生素受到争论。它们可因此有利于抗性的建立。此外,由于它们的分子结构(其大多数复杂),抗生素价格昂贵并且仅可通过生物技术方法生产。因此,本发明的目的是减少在农业中使用抗生素的需要。
防止植物中细菌性病害的可选择方法在WO03/075663中教导:嗜球果伞素(strobilurin)类型杀真菌剂对植物内部免疫系统对抗细菌具有刺激作用。然而,此作用不总完全令人满意。
本发明的目的是提供一种可广泛使用的高度有效的方法,其不损害植物并以降低的活性化合物施用总量产生提高的植物对植物细菌病害的耐受性。
我们发现此目的通过开头定义的方法实现。上述式I的嗜球果伞素作为杀真菌剂并且在一些情况下还作为杀虫剂(EP-A178826;EP-A253213;WO93/15046;WO95/18789;WO95/21153;WO95/21154;WO95/24396;WO96/01256;WO97/15552)已知。
现有技术没有教导以上作为组分2)提到的化合物对细菌的预防性作用,或当与嗜球果伞素组合施用时,已知活性化合物2)可影响植物对植物细菌病害的免疫系统。
上述组A)-M)的活性化合物,其制备方法及其对有害真菌的作用通常为本领域已知的(参见:http://www.hclrss.demon.co.uk/index.html;ThePecticide Manual,第10版,BCPC,1995);
4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-溴-联苯-2-基)-酰胺、4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-三氟甲基-联苯-2-基)-酰胺、4-二氟甲基-2-甲基-噻唑-5-甲酸-(4’-氯-3’-氟-联苯-2-基)-酰胺、3-二氟甲基-1-甲基-吡唑-4-甲酸-(3’,4’-二氯-4-氟-联苯-2-基)-酰胺(WO03/066610),
3,4-二氯-异噻唑-5-甲酸(2-氰基-苯基)酰胺(WO99/24413),
N-(2-(4-[3-(4-氯-苯基)-丙-2-炔基氧基]-3-甲氧基-苯基)-乙基)-2-甲烷磺酰基氨基-3-甲基-丁酰胺、N-(2-(4-[3-(4-氯-苯基)-丙-2-炔基氧基]-3-甲氧基-苯基)-乙基)-2-乙烷磺酰基氨基-3-甲基-丁酰胺(WO04/049804),
3-[5-(4-氯-苯基)-2,3-二甲基-异噁唑烷-3-基]-吡啶(EP-A1035122),
2-丁氧基-6-碘-3-丙基-苯并呋喃-4-酮(WO03/14103),
3-(3-溴-6-氟-2-甲基-吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酸二甲基酰胺(EP-A1031571),
(2-氯-5-[1-(3-甲基-苄基氧基亚氨基)-乙基]-苄基)-氨基甲酸甲基酯、(2-氯-5-[1-(6-甲基-吡啶-2-基甲氧基亚氨基)-乙基]-苄基)-氨基甲酸甲基酯(EP-A1201648)、
3-(4-氯-苯基)-3-(2-异丙氧基羰基氨基-3-甲基-丁酰氨基)-丙酸甲基酯(EP-A1028125)、
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′-二氯联苯-2-基)-酰胺(WO2007/000462);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,5′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,5′-二氯联苯-2-基)-酰胺(WO2007/003540);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,5′-二氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,5′-二氯联苯-2-基)-酰胺(WO2007/003564);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′-氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′-氯联苯-2-基)-酰胺(WO2007/003603);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′-氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′-氯联苯-2-基)-酰胺(WO2007/006806);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3′,4′,5′-三氟联苯-2-基)-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(2′,4′,5′-三氟联苯-2-基)-酰胺(PCT/EP2006/064907);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸[2-(1,1,2,3,3,3-六氟丙氧基)-苯基]-酰胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸[2-(1,1,2,2-四氟乙氧基)-苯基]-酰胺(PCT/EP2006/064988);
3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(4′-三氟甲基硫代联苯-2-基)-酰胺(EP申请号06123463.9);
N-(2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺(WO03/074491)。
以上引用的出版物描述了制备用于本发明方法的活性成分的合成路线。
由它们的通用名表示的化合物为市售的。
防治植物病害所需浓度的式I活性成分与植物的良好相容性容许气生植物部分的处理以及繁殖材料和种子和土壤的处理。
在本发明方法中,活性成分通过叶表面或通过根由植物吸收并在整个植物内分布汁液中。
因此,在进行本发明方法以后的保护作用不仅发现于直接喷雾的那些植物部分中,而且整个植物的细菌性病害耐受性提高。
在本方法的优选实施方案中,将气生植物部分用配制剂或用活性成分1)和2)的桶混物处理。
对于本发明方法,特别优选取代基每种情况下单独或组合具有如下含义的活性成分,将引用的出版物的公开内容在此引入:
对于本发明方法,特别优选式II-VIII的活性成分作为组分1,其中:
V为OCH3和NHCH3,
Y为CH和N,和
T和Z相互独立地为CH和N。
其中Q为N(-OCH3)-COOCH3的优选式I活性成分为出版物WO93/15046和WO96/01256所述的化合物。
其中Q为C(=CH-OCH3)-COOCH3的优选式I活性成分为出版物EP-A178 826和EP-A 278 595所述的化合物。
其中Q为C(=N-OCH3)-COOCH3的优选式I活性成分为出版物EP-A253 213和EP-A 254 426所述的化合物。
其中Q为C(=N-OCH3)-CONHCH3的优选式I活性成分为出版物EP-A398 692、EP-A 477 631和EP-A 628 540所述的化合物。
其中Q为C(=CH-CH3)-COOCH3的优选式I活性成分为出版物EP-A280 185和EP-A 350 691所述的化合物。
其中Q为-CH2O-N=C(R1)-B的优选式I活性成分为出版物EP-A 460575和EP-A 463 488所述的化合物。
其中A为-O-B的优选式I活性成分为出版物EP-A 382 375和EP-A 398692所述的化合物。
其中A为-CH2O-N=C(R1)-C(R2)=N-OR3的优选式I活性成分为出版物WO95/18789、WO95/21153、WO95/21154、WO97/05103和WO97/06133所述的化合物。
尤其优选其中变量如下的式I活性成分:
Q为N(-OCH3)-COOCH3,
A为CH2-O-和
B为3-吡唑基或1,2,4-三唑基,其中B上已连有一个或两个选自如下的取代基:
·卤素、甲基和三氟甲基,和
·由1-3个基团Rb取代的苯基和吡啶基,尤其是2-吡啶基。
这些活性成分由式II描述:
其中T为碳或氮原子,Ra’为卤素、甲基和三氟甲基,y为0、1或2,Rb如式I定义,x为0、1、2、3或4。
更优选的活性成分为式II’的那些:
其中Rb如式I定义。
关于它们的用途,尤其优选如下表中汇编的化合物。
表I
编号 | T | (Ra’)y | 基团苯基-(Rb)x的位置 | (Rb)x | 参考 |
I-1 | N | - | 1 | 2,4-Cl2 | WO96/01256 |
I-2 | N | - | 1 | 4-Cl | WO96/01256 |
I-3 | CH | - | 1 | 2-Cl | WO96/01256 |
I-4 | CH | - | 1 | 3-Cl | WO96/01256 |
I-5 | CH | - | 1 | 4-Cl | WO96/01256 |
I-6 | CH | - | 1 | 4-CH3 | WO96/01256 |
I-7 | CH | - | 1 | H | WO96/01256 |
编号 | T | (Ra’)y | 基团苯基-(Rb)x的位置 | (Rb)x | 参考 |
I-8 | CH | - | 1 | 3-CH3 | WO96/01256 |
I-9 | CH | 5-CH3 | 1 | 3-CF3 | WO96/01256 |
I-10 | CH | 1-CH3 | 5 | 3-CF3 | WO99/33812 |
I-11 | CH | 1-CH3 | 5 | 4-Cl | WO99/33812 |
I-12 | CH | 1-CH3 | 5 | - | WO99/33812 |
表II
编号 | V | Y | Ra | 参考 |
II-1 | OCH3 | N | 2-CH3 | EP-A 253 213 |
II-2 | OCH3 | N | 2,5-(CH3)2 | EP-A 253 213 |
II-3 | NHCH3 | N | 2,5-(CH3)2 | EP-A 477 631 |
II-4 | NHCH3 | N | 2-Cl | EP-A 398 692 |
II-5 | NHCH3 | N | 2-CH3 | EP-A 398 692 |
II-6 | NHCH3 | N | 2-CH3,4-OCF3 | EP-A 628 540 |
II-7 | NHCH3 | N | 2-Cl,4-OCF3 | EP-A 628 540 |
II-8 | NHCH3 | N | 2-CH3,4-OCH(CH3)-C(CH3)=NOCH3 | EP-A 11 18 609 |
II-9 | NHCH3 | N | 2-Cl,4-OCH(CH3)-C(CH3)=NOCH3 | EP-A 11 18 609 |
II-10 | NHCH3 | N | 2-CH3,4-OCH(CH3)-C(CH2CH3)=NOCH3 | EP-A 11 18 609 |
II-11 | OCH3 | CH | 2,5-(CH3)2 | EP-A 226 917 |
表III
编号 | V | Y | T | Ra | 参考 |
III-1 | OCH3 | CH | N | 2-OCH3,4-CF3 | WO96/16047 |
III-2 | OCH3 | CH | N | 2-OCH(CH3)2,4-CF3 | WO96/16047 |
III-3 | OCH3 | CH | CH | 2-CF3 | EP-A 278 595 |
III-4 | OCH3 | CH | CH | 4-CF3 | EP-A 278 595 |
III-5 | NHCH3 | N | CH | 2-Cl | EP-A 398 692 |
III-6 | NHCH3 | N | CH | 2-CF3 | EP-A 398 692 |
III-7 | NHCH3 | N | CH | 2-CF3,4-Cl | EP-A 398 692 |
III-8 | NHCH3 | N | CH | 2-Cl,4-CF3 | EP-A 398 692 |
表IV
编号 | V | Y | R1 | B | 参考 |
IV-1 | OCH3 | CH | CH3 | (3-CF3)C6H4 | EP-A 370 629 |
IV-2 | OCH3 | CH | CH3 | (3,5-Cl2)C6H3 | EP-A 370 629 |
IV-3 | NHCH3 | N | CH3 | (3-CF3)C6H4 | WO92/13830 |
IV-4 | NHCH3 | N | CH3 | (3-OCF3)C6H4 | WO92/13830 |
IV-5 | OCH3 | N | CH3 | (3-OCF3)C6H4 | EP-A 460 575 |
IV-6 | OCH3 | N | CH3 | (3-CF3)C6H4 | EP-A 460 575 |
IV-7 | OCH3 | N | CH3 | (3,4-Cl2)C6H3 | EP-A 460 575 |
IV-8 | OCH3 | N | CH3 | (3,5-Cl2)C6H3 | EP-A 463 488 |
IV-9 | OCH3 | CH | CH3 | CH=CH-(4-Cl)C6H4 | EP-A 936 213 |
表V
编号 | V | R1 | R2 | R3 | 参考 |
V-1 | OCH3 | CH3 | CH3 | CH3 | WO95/18789 |
V-2 | OCH3 | CH3 | CH(CH3)2 | CH3 | WO95/18789 |
V-3 | OCH3 | CH3 | CH2CH3 | CH3 | WO95/18789 |
V-4 | NHCH3 | CH3 | CH3 | CH3 | WO95/18789 |
V-5 | NHCH3 | CH3 | 4-F-C6H4 | CH3 | WO95/18789 |
V-6 | NHCH3 | CH3 | 4-Cl-C6H4 | CH3 | WO95/18789 |
V-7 | NHCH3 | CH3 | 2,4-C6H3 | CH3 | WO95/18789 |
V-8 | NHCH3 | Cl | 4-F-C6H4 | CH3 | WO98/38857 |
V-9 | NHCH3 | Cl | 4-Cl-C6H4 | CH2CH3 | WO98/38857 |
V-10 | NHCH3 | CH3 | CH2C(=CH2)CH3 | CH3 | WO97/05103 |
V-11 | NHCH3 | CH3 | CH=C(CH3)2 | CH3 | WO97/05103 |
V-12 | NHCH3 | CH3 | CH=C(CH3)2 | CH2CH3 | WO97/05103 |
V-13 | NHCH3 | CH3 | CH=C(CH3)CH2CH3 | CH3 | WO97/05103 |
V-14 | NHCH3 | CH3 | O-CH(CH3)2 | CH3 | WO97/06133 |
V-15 | NHCH3 | CH3 | O-CH2CH(CH3)2 | CH3 | WO97/06133 |
V-16 | NHCH3 | CH3 | C(CH3)=NOCH3 | CH3 | WO97/15552 |
表VI
编号 | V | Y | Ra | 参考 |
VI-1 | NHCH3 | N | H | EP-A 398 692 |
编号 | V | Y | Ra | 参考 |
VI-2 | NHCH3 | N | 3-CH3 | EP-A 398 692 |
VI-3 | NHCH3 | N | 2-NO2 | EP-A 398 692 |
VI-4 | NHCH3 | N | 4-NO2 | EP-A 398 692 |
VI-5 | NHCH3 | N | 4-Cl | EP-A 398 692 |
VI-6 | NHCH3 | N | 4-Br | EP-A 398 692 |
表VII
编号 | Q | Ra | 参考 |
VII-1 | C(=CH-OCH3)COOCH3 | 5-O-(2-CN-C6H4) | EP-A 382 375 |
VII-2 | C(=CH-OCH3)COOCH3 | 5-O-(2-Cl-C6H4) | EP-A 382 375 |
VII-3 | C(=CH-OCH3)COOCH3 | 5-O-(2-CH3-C6H4) | EP-A 382 375 |
VII-4 | C(=N-OCH3)CONHCH3 | 5-O-(2-Cl-C6H4) | GB-A 2253624 |
VII-5 | C(=N-OCH3)CONHCH3 | 5-O-(2,4-Cl2-C6H3) | GB-A2253624 |
VII-6 | C(=N-OCH3)CONHCH3 | 5-O-(2-CH3-C6H4) | GB-A2253624 |
VII-7 | C(=N-OCH3)CONHCH3 | 5-O-(2-CH3,3-Cl-C6H3) | GB-A2253624 |
VII-8 | C(=N-OCH3)CONHCH3 | 4-F,5-O-(2-CH3-C6H4) | WO98/21189 |
VII-9 | C(=N-OCH3)CONHCH3 | 4-F,5-O-(2-Cl-C6H4) | WO98/21189 |
VII-10 | C(=N-OCH3)CONHCH3 | 4-F,5-O-(2-CH3,3-Cl-C6H3) | WO98/21189 |
VII-11 | Q1 | 4-F,5-O-(2-Cl-C6H4) | WO97/27189 |
VII-12 | Q1 | 4-F,5-O-(2-CH3,3-Cl-C6H3) | WO97/27189 |
VII-13 | Q1 | 4-F,5-O-(2,4-Cl2-C6H3) | WO97/27189 |
特别优选一种如下组分1与一种选自组A)-M)的化合物的组合:化合物I-5(唑菌胺酯(pyraclostrobin))、II-1(亚胺菌(kresoxim-methyl))、II-3(醚菌胺(dimoxystrobin))、II-11(ZJ0712)、III-3(啶氧菌酯(picoxystrobin))、IV-6(肟菌酯(trifloxystrobin))、IV-9(烯肟菌酯(enestroburin))、V-16(肟醚菌胺(orysastrobin))、VI-1(叉氨苯酰胺(metominostrobin))、VII-1(腈嘧菌酯(azoxystrobin))和VII-11(氟嘧菌酯(fluoxastrobin))。
在本发明一个实施方案中,使用唑菌胺酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用亚胺菌与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用醚菌胺与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用ZJ0712与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用啶氧菌酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用肟菌酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用烯肟菌酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用肟醚菌胺与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用叉氨苯酰胺与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用腈嘧菌酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用氟嘧菌酯与一种选自组A)-M)的化合物的组合。
在本发明另一个实施方案中,使用一种式I化合物与一种如下化合物的组合:
A)酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl);
B)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)、螺噁茂胺(spiroxamine)、克啉菌(tridemorph);
C)苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil);
D)唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、噁醚唑(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(triflumizole)、戊叉唑菌(triticonazole),
E)二羧酰亚胺类,例如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)、烯菌酮(vinclozolin),
F)二硫代氨基甲酸盐类,例如福美铁(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),
G)杂环化合物,例如敌菌灵(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)、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(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、吡噻菌胺(penthiopyrad)、氟吡菌胺(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(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine)、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,
H)硫,
I)硝基苯基衍生物,例如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthal-isopropyl),
J)苯基吡咯类,例如拌种咯(fenpiclonil)或氟噁菌(fludioxonil),
K)其它杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、哒菌清(diclomezine)、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)、亚磷酸及其盐、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、双炔酰菌胺(mandipropamid)、苯菌酮(metrafenone)、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(zoxamide)、乙酰基水杨酸,
L)次磺酸衍生物,例如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)、对甲抑菌灵(tolylfluanid),和
M)肉桂酰胺及类似化合物,例如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
更优选用上述式I化合物与选自下组的化合物进行本方法:
A)酰基丙氨酸类,尤其是苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl);
B)胺衍生物,尤其是多果定(dodine)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
D)唑类,尤其是氧唑菌(epoxiconazole)、喹唑菌酮(fluquinconazole)、粉唑醇(flutriafol)、烯菌灵(imazalil)、环戊唑菌(metconazole)、丙氯灵(prochloraz)、戊唑醇(tebuconazole)、戊叉唑菌(triticonazole),
F)二硫代氨基甲酸盐类,尤其是福美铁(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),
G)杂环化合物,尤其是敌菌灵(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)、二噻农(dithianon)、氟酰胺(flutolanil)、涕必灵(thiabendazole)、甲基托布津(thiophanate-methyl)、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,
K)其它杀真菌剂,尤其是噻二唑素(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)、噻唑菌胺(ethaboxam)、亚磷酸及其盐、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、苯菌酮(metrafenone),
L)次磺酸衍生物,尤其是灭菌丹(folpet),和
M)肉桂酰胺及类似化合物,尤其是烯酰吗啉(dimethomorph)。
特别优选含一种如下化合物作为组分2)的组合:
F)二硫代氨基甲酸盐类,尤其是代森锰锌(mancozeb)、代森联(metiram),
G)杂环化合物,尤其是多菌灵(carbendazim)、二噻农(dithianon)、甲基托布津(thiophanate-methyl),
K)其它杀真菌剂,尤其是噻二唑素(acibenzolar-S-methyl)、亚磷酸及其盐。
在本发明一个实施方案中,使用式I化合物与二硫代氨基甲酸盐类,尤其是代森锰锌(mancozeb)或代森联(metiram)的组合。
此外特别有用的是式I化合物与杂环化合物,尤其是多菌灵(carbendazim)、二噻农(dithianon)或甲基托布津(thiophanate-methyl)的组合。
还特别有用的是式I化合物与噻二唑素(acibenzolar-S-methyl)或亚磷酸及其碱金属和碱土金属盐的组合。
活性成分1)和2)的组合提高植物对细菌病害的耐受性。它们在防治各种作物植物如蔬菜、顶果属和烟草,和所有这些植物种子上的细菌中尤其重要。
具体而言,它们适于防治如下植物病害:
烟草、马铃薯、西红柿和豆类上的假单胞菌(Pseudomonas)属,以及尤其是水果、蔬菜和马铃薯上的欧文氏菌(Erwinia)属。
化合物通过以有效量的活性成分处理土壤或待保护以防细菌侵袭的种子或植物而施用。施用可在细菌侵染植物或种子以前和以后进行。
优选化合物1)和2)的施用在通常第一次对于真菌保护性施用很久以前,在植物生长周期的第一个六周,优选四周期间进行。
将植物在侵袭发生以前,优选在预期细菌侵袭以前几周至一周处理。在该时间范围内,进行1-10次施用。观察到植物对细菌病害显著减低的敏感性。
在蔬菜和田间作物的情况下,优选将活性成分在植物发芽以后,尤其是发芽以后第一个四周内立刻施用。在水果和其他多年生植物的情况下,第一次施用在植物生长周期开始或第一个四周内进行。在所有情况下,当施用每10-20天重复时,观察到最佳效率。
当施用于水果和蔬菜如马铃薯、西红柿、葫芦,优选黄瓜、甜瓜、西瓜、大蒜、洋葱和莴苣时,本发明方法优选作为叶面施用进行。在一季内,优选进行多于两次施用,至多10次施用。
当施用于水果如苹果、核果和柑橘时,本发明方法优选作为叶面施用进行。在一季内,优选进行多于两次施用,至多5次施用。
本发明方法也可施用于田间作物如大豆、玉米、棉花、烟草、菜豆、小麦、大麦、豌豆及其他。对于这些作物,本方法优选通过处理种子或植物而施用。优选将植物以2-3次施用处理。
组分1)和组分2)可同时,即联合或分开,或依次地施用,在分开施用的情况下,顺序通常对防治措施的结果不具有任何影响。
在本发明混合物的一个实施方案中,将其他活性化合物3)或两种活性化合物3)和4)加入组分1)和2)中。适合的化合物3)和4)选自作为组分2)提到的化合物。
优选组分1)和2)与组分3)的混合物。特别优选组分1)和2)的混合物。
组分1)和组分2)的施用比取决于具体化合物1)和化合物2),通常它们以1000:1-1:1000,优选100:1-1:100,更优选20:1-1:20,尤其是10:1-1:10的重量比施用。
如果需要的话,组分3)和如果合适的话4)以20:1-1:20的比加入组分1)中。
在优选实施方案中,观察到对细菌病害的协同增加的预防性效力。
取决于化合物类型和所需效力,本发明混合物的施用率为5-2000g/ha,优选50-1000g/ha,尤其是50-750g/ha。
相应地,组分1)的施用率通常为1-1000g/ha,优选10-900g/ha,尤其是20-750g/ha。
相应地,组分2)的施用率通常为1-2000g/ha,优选10-1000g/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种子,尤其是5-100g/100kg种子。
对于作物保护中的使用,取决于病原体类型和植物品种,施用率为每公顷0.01-2.0kg,优选至多1.0kg活性成分。
在种子处理中,每kg种子通常需要0.001-0.1g,优选0.01-0.05g活性成分。
如果二氟吡隆(diflufenzopyr)用作组分2),则它以非常低的剂量使用,在这种情况下,重量比优选1000:1-30:1,优选1000:1-50:1,尤其是500:1-100:1。
取决于待保护的植物类型,二氟吡隆(diflufenzopyr)的施用率为50mg至10g/ha,优选100mg至2g/ha。
就保护单子叶植物而言,100mg-10g/ha,优选100mg-5g/ha的二氟吡隆(diflufenzopyr)足以增强植物的抵抗力。
就保护双子叶植物而言,使用50mg-5g/ha,优选100mg-2g/ha的二氟吡隆(diflufenzopyr)。
可将本发明混合物或组分1)和2)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意欲目的;在每种情况下,应确保本发明化合物精细且均匀地分布。
当使用支持活性化合物输入植物中并且在整个植物中分布于汁液中的配制剂时,得到最好结果。这种尤其适合的配制剂例如为EC、DC和SE。
化合物1)和2)可以直接、以其配制剂形式或由其制备的使用形式,例如可直接喷雾溶液、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、撒播或浇灌而使用。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,也可制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂和如果合适的话溶剂或油组成的浓缩物且这种浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可在相对宽范围内变化。它们通常为0.0001-10%,优选0.01-1重量%。
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。
配制剂以已知方式制备,例如通过将活性化合物与适于配制农用化学品的助剂如溶剂和/或载体,需要的话乳化剂、表面活性剂和分散剂,防腐剂,消泡剂,防冻剂混合而制备(例如参见评论US3,060,084、EP-A707 445(对于液体浓缩物),Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,147-48,Perry’s Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57页及随后各页,WO91/13546、US4,172,714、US4,144,050、US3,920,442、US5,180,587、US5,232,701、US5,208,030、GB2,095,558、US3,299,566,Klingman,Weed Control asa Science,John Wiley and Sons,Inc.,New York,1961,Hance等,WeedControl Handbook,第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCHVerlag GmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistry andTechnology of Agrochemical Formulations,Kluwer Academic Publishers,Dordrecht,1998(ISBN0-7514-0443-8)。
适合的溶剂的实例为水、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。
适合的乳化剂为非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)。
分散剂的实例为木素亚硫酸盐废液和甲基纤维素。
适合的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,聚氧乙烯辛基苯酚醚,乙氧基化的异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,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是中至高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如甲苯、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,例如二甲亚砜、N-甲基吡咯烷酮或水。
也可例如将防冻剂如甘油、乙二醇、丙二醇和杀菌剂加入配制剂中。
适合的消泡剂例如为基于硅酮或硬脂酸镁的消泡剂。
适合的防腐剂例如为双氯酚和烯醇半缩甲醛(enzylalkoholhemiformal)。
种子处理配制剂可额外包含粘合剂和任选着色剂。
可加入粘合剂以改善处理以后活性材料在种子上的附着力。适合的粘合剂为嵌段共聚物EO/PO表面活性剂,以及聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺( )、聚醚、聚氨酯、聚乙酸乙烯酯、纤基乙酸钠和衍生于这些聚合物的共聚物。
粉末、撒播用材料和可撒粉产品可通过将活性物质和固体载体混合或一起研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性成分与固体载体粘附而制备。
固体载体的实例是矿土如硅胶、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,和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。在这种情况下,活性化合物以90-100重量%,优选95-100重量%的纯度(根据NMR谱)使用。
对于种子处理,各种配制剂可稀释2-10倍,导致即用制剂的浓度为0.01-60重量%,优选0.1-40重量%活性化合物。
下列为配制剂实例:
1.用水稀释而叶面施用的产品。对于种子处理而言,这种产品可经稀释或不经稀释而施用于种子。
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。作为选择,加入湿润剂或其它助剂。活性化合物经水稀释溶解,由此得到具有10%(w/w)活性化合物的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物随着加入10重量份分散剂如聚乙烯基吡咯烷酮而溶于70重量份环己酮中。用水稀释得到分散体,由此得到具有20%(w/w)活性化合物的配制剂。
C)可乳化浓缩物(EC)
将15重量份活性化合物随着加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(每种情况下5重量份)而溶于7重量份二甲苯中。用水稀释得到乳液,由此得到具有15%(w/w)活性化合物的配制剂。
D)乳液(EW、EO、ES)
将25重量份活性化合物随着加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(每种情况下5重量份)而溶于35重量份二甲苯中。通过乳化机(例如Ultraturrax)将该混合物引入30重量份水中并制成均匀乳液。用水稀释得到乳液,由此得到具有25%(w/w)活性化合物的配制剂。
E)悬浮液(SC、OD、FS)
在搅拌球磨机中,将20重量份活性化合物随着加入10重量份分散剂和润湿剂以及70重量份水或有机溶剂而粉碎以得到细活性化合物悬浮液。用水稀释得到活性化合物的稳定悬浮液,由此得到具有20%(w/w)活性化合物的配制剂。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物随着加入50重量份分散剂和润湿剂而精细磨碎并通过工业装置(例如挤出机、喷雾塔、流化床)而制得水分散性或水溶性颗粒。用水稀释得到活性化合物的稳定分散体或溶液,由此得到具有50%(w/w)活性化合物的配制剂。
G)水分散性或水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子研磨机中随着加入25重量份分散剂、润湿剂和硅胶而磨碎。用水稀释得到活性化合物的稳定分散体或溶液,由此得到具有75%(w/w)活性化合物的配制剂。
2.不经稀释而叶面施用的产品。就种子处理而言,这种产品可经稀释而施用于种子。
I)可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到具有5%(w/w)活性化合物的可撒粉产品。
J)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重量份载体,由此得到具有0.5%(w/w)活性化合物的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而叶面使用的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到具有10%(w/w)活性化合物的不经稀释而叶面使用的产品。
常规种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS以及乳液ES和EC和凝胶配制剂GF。这些配制剂可经稀释或未经稀释而施用于种子。施用于种子在撒播以前,或直接在种子上进行。
在优选实施方案中,FS配制剂用于种子处理。FS配制剂通常可包含1-800g/l活性成分、1-200g/l表面活性剂、0-200g/l防冻剂、0-400g/l粘合剂、0-200g/l颜料和至多1升溶剂,优选水。
各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂可加入活性化合物中,甚至如果合适的话在紧邻使用前加入(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。
提及活性成分1)和2)在引发对细菌耐受性中的效力的注释可作为包装上的标签存在或存在于产品数据表中。在制剂的情况下,也可存在注释,其可与活性成分1)和2)组合使用。
耐受性的引发也可构成可以为活性化合物1)和2)组合正式批准主题的说明。
生物学实施例
西红柿上对黄单孢菌属(Xathomonas ssp.)的预防性作用
试验在田间条件下进行。种植约10cm高的品种Carmen的西红柿植物并在具有水和养分充分供应的标准条件下生长。18天以后,进行第一次活性化合物施用,每5-8天重复五次。不施用其他化合物以防治病原体。用天然存在的病原体侵染。每次处理由无规则区组设计的4个平行组成。在第一次施用以后第46天计算病害发生率(黄单孢菌属)。所用剂量和得到的结果在以下显示:
将目测的侵染叶面积百分数转化成以未处理对照的%表示的效力:
使用Abbot公式按如下计算效力(E):
E=(1-α/β)·100
α对应于%表示的处理植物的真菌侵染百分数,和
β对应于%表示的未处理(对照)植物的真菌侵染百分数。
效力为0意指处理植物的侵染水平相当于未处理对照植物的;效力为100意指处理植物未受侵染。
活性化合物混合物的预期效力使用Colby公式(Colby,S.R.“Calculating synergistic and antagonistic responses of herbicidecombinations”,Weeds(杂草),15,第20-22页,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,以未处理对照的%表示。
Claims (13)
1.一种引发植物对细菌病害耐受性的方法,其包括用有效量的如下化合物的组合处理植物、土壤或种子:
1)选自唑菌胺酯的化合物;和
2)选自代森联的化合物;
其中活性化合物1)和2)被植物或种子吸收,
其中组分1)和2)以100:1-1:100的比使用,
所述植物选自马铃薯和西红柿。
2.权利要求1的方法,其中组分1)和2)以协同增效有效量施用。
3.权利要求1的方法,其中组分1)和2)以20:1-1:20的比使用。
4.权利要求2的方法,其中组分1)和2)以20:1-1:20的比使用。
5.权利要求1-4中任一项的方法,其中组分1)和2)的施用在植物生长周期的第一个六周期间进行。
6.权利要求1-4中任一项的方法,其中组分1)和2)的施用在植物发芽以后的第一个四周内进行。
7.权利要求1-4中任一项的方法,其中组分1)和2)的施用在预期细菌侵袭以前进行1-10次。
8.权利要求6的方法,其中组分1)和2)的施用在预期细菌侵袭以前进行1-10次。
9.权利要求1-4中任一项的方法,其中将组分1)和2)施用于马铃薯或西红柿植物。
10.权利要求8的方法,其中将组分1)和2)施用于马铃薯或西红柿植物。
11.权利要求1-4中任一项的方法,其中将组分1)和2)施用于种子。
12.权利要求10的方法,其中将组分1)和2)施用于种子。
13.如权利要求1-4任一项中定义的组合在引发植物细菌耐受性中的用途,其中组分1)和2)以100:1-1:100的比使用,所述植物选自马铃薯和西红柿。
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US (1) | US20090011935A1 (zh) |
EP (1) | EP1996018A2 (zh) |
JP (1) | JP2009529565A (zh) |
KR (1) | KR20080111058A (zh) |
CN (1) | CN101400259B (zh) |
AR (1) | AR059892A1 (zh) |
AU (1) | AU2007224576A1 (zh) |
BR (1) | BRPI0708283A2 (zh) |
CA (1) | CA2640963A1 (zh) |
CL (1) | CL2007000658A1 (zh) |
EA (1) | EA015354B1 (zh) |
PE (1) | PE20071285A1 (zh) |
TW (1) | TW200806178A (zh) |
WO (1) | WO2007104658A2 (zh) |
ZA (1) | ZA200808667B (zh) |
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TWI335218B (en) | 2003-02-19 | 2011-01-01 | Panion & Bf Biotech Inc | Ferric organic compounds, uses thereof and methods of making same |
US20070196474A1 (en) * | 2004-04-30 | 2007-08-23 | Withiam Michael C | Rapidly disintegrating low friability tablets comprising calcium carbonate |
EA015449B1 (ru) | 2006-03-24 | 2011-08-30 | Басф Се | Способ борьбы с фитопатогенными грибами |
WO2007110173A2 (de) * | 2006-03-24 | 2007-10-04 | Bayer Cropscience Ag | Fungizide wirkstoffkombinationen |
US20110105579A1 (en) | 2008-02-05 | 2011-05-05 | Ronald Wilhelm | Plant Health Composition |
CN101700026B (zh) * | 2009-11-11 | 2013-02-27 | 陕西上格之路生物科学有限公司 | 一种含有环丙唑醇的杀菌组合物 |
CN102283228B (zh) * | 2010-06-19 | 2013-05-15 | 海利尔药业集团股份有限公司 | 一种含有吡唑醚菌酯和丙森锌的杀菌组合物 |
CN103140766B (zh) | 2010-07-26 | 2016-02-03 | 普睿司曼股份公司 | 用于通过部分放电分析监视电力传输系统的装置和方法 |
CN103749459A (zh) * | 2010-12-30 | 2014-04-30 | 陕西美邦农药有限公司 | 一种含氰霜唑与甲氧基丙烯酸酯类化合物的杀菌组合物 |
CN102197820A (zh) * | 2011-04-08 | 2011-09-28 | 陕西汤普森生物科技有限公司 | 一种含有啶氧菌酯与苯并咪唑类的杀菌组合物 |
CN103858883B (zh) * | 2011-04-27 | 2016-01-20 | 陕西汤普森生物科技有限公司 | 一种含有啶氧菌酯与酰胺类的农药组合物 |
CN103444744A (zh) * | 2012-06-02 | 2013-12-18 | 陕西美邦农药有限公司 | 一种含咪唑菌酮与甲氧基丙烯酸酯类的杀菌组合物 |
CN103444738B (zh) * | 2012-06-05 | 2016-06-08 | 陕西美邦农药有限公司 | 一种含咪唑菌酮与硫代氨基甲酸酯类的杀菌组合物 |
CN103563920B (zh) * | 2012-08-04 | 2015-06-03 | 南京华洲药业有限公司 | 一种含噻呋酰胺和啶氧菌酯的杀菌组合物及其应用 |
CN102907447A (zh) * | 2012-11-20 | 2013-02-06 | 河北三农农用化工有限公司 | 一种农用杀菌组合物 |
CN102986692A (zh) * | 2012-12-28 | 2013-03-27 | 江苏龙灯化学有限公司 | 一种含有噻呋酰胺和烯肟菌酯的杀菌组合物及其用途 |
CN103053560B (zh) * | 2012-12-29 | 2015-01-28 | 广东中迅农科股份有限公司 | 苯噻菌胺和醚菌酯杀菌组合物 |
CN103109831A (zh) * | 2013-03-09 | 2013-05-22 | 海利尔药业集团股份有限公司 | 一种含有吡唑醚菌酯与咪唑菌酮的杀菌组合物 |
CN103798237B (zh) * | 2013-11-19 | 2015-09-09 | 广西田园生化股份有限公司 | 一种含有啶酰菌胺的超低容量液剂 |
CN103734163A (zh) * | 2013-12-27 | 2014-04-23 | 江苏绿叶农化有限公司 | 一种含肟菌酯的杀菌组合物及其应用 |
CN105052958B (zh) * | 2015-07-19 | 2018-08-14 | 广东中迅农科股份有限公司 | 一种多功能水稻杀菌组合物 |
CN105766919A (zh) * | 2016-04-22 | 2016-07-20 | 广东中迅农科股份有限公司 | 含有氟菌唑和苯醚菌酯的杀菌组合物 |
CN106879599B (zh) * | 2017-03-24 | 2018-08-03 | 浙江博仕达作物科技有限公司 | 三氮唑磺酸酯类化合物在防治水稻细菌性病害中的应用 |
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- 2007-03-02 KR KR1020087024924A patent/KR20080111058A/ko not_active Application Discontinuation
- 2007-03-02 WO PCT/EP2007/051986 patent/WO2007104658A2/en active Application Filing
- 2007-03-02 BR BRPI0708283-5A patent/BRPI0708283A2/pt not_active Application Discontinuation
- 2007-03-02 EA EA200801902A patent/EA015354B1/ru not_active IP Right Cessation
- 2007-03-02 CN CN2007800092270A patent/CN101400259B/zh not_active Expired - Fee Related
- 2007-03-02 US US12/279,309 patent/US20090011935A1/en not_active Abandoned
- 2007-03-02 EP EP07726584A patent/EP1996018A2/en not_active Withdrawn
- 2007-03-02 AU AU2007224576A patent/AU2007224576A1/en not_active Abandoned
- 2007-03-13 CL CL2007000658A patent/CL2007000658A1/es unknown
- 2007-03-13 AR ARP070101021A patent/AR059892A1/es not_active Application Discontinuation
- 2007-03-13 PE PE2007000270A patent/PE20071285A1/es not_active Application Discontinuation
- 2007-03-13 TW TW096108604A patent/TW200806178A/zh unknown
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2008
- 2008-10-10 ZA ZA200808667A patent/ZA200808667B/xx unknown
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Also Published As
Publication number | Publication date |
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AR059892A1 (es) | 2008-05-07 |
EP1996018A2 (en) | 2008-12-03 |
PE20071285A1 (es) | 2008-03-02 |
BRPI0708283A2 (pt) | 2011-05-24 |
CA2640963A1 (en) | 2007-09-20 |
AU2007224576A1 (en) | 2007-09-20 |
CN101400259A (zh) | 2009-04-01 |
ZA200808667B (en) | 2009-12-30 |
KR20080111058A (ko) | 2008-12-22 |
EA200801902A1 (ru) | 2009-02-27 |
WO2007104658A3 (en) | 2008-02-28 |
WO2007104658A2 (en) | 2007-09-20 |
TW200806178A (en) | 2008-02-01 |
JP2009529565A (ja) | 2009-08-20 |
US20090011935A1 (en) | 2009-01-08 |
CL2007000658A1 (es) | 2008-01-18 |
EA015354B1 (ru) | 2011-06-30 |
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