CN103501598B - 包含二甲亚砜和磷酸酯的助剂 - Google Patents
包含二甲亚砜和磷酸酯的助剂 Download PDFInfo
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- CN103501598B CN103501598B CN201280021654.1A CN201280021654A CN103501598B CN 103501598 B CN103501598 B CN 103501598B CN 201280021654 A CN201280021654 A CN 201280021654A CN 103501598 B CN103501598 B CN 103501598B
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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
- 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
-
- 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
-
- 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
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明涉及一种用于提高农药活性的助剂,其包含极性溶剂和式(A)的磷酸酯(如下文描述),其中式(A)的磷酸酯可作为游离酸和/或作为盐存在,并且其中极性溶剂与水以任意比例混溶且具有超过60℃的闪点。此外,本发明涉及一种包含农药和所述助剂的农化组合物;一种制备所述助剂的方法,其中使极性溶剂和式(A)的磷酸酯接触;所述助剂在提高农药活性中的用途;以及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法,其中使该组合物作用于相应有害物、其环境或待防止相应有害物的作物、土壤和/或不希望的植物和/或作物和/或其环境。
Description
本发明涉及一种用于提高农药活性的助剂,其包含极性溶剂和式(A)的磷酸酯(如下文描述),其中式(A)的磷酸酯可作为游离酸和/或作为盐存在,并且其中极性溶剂与水以任意比例混溶且具有超过60℃的闪点。此外,本发明涉及一种包含农药和所述助剂的农化组合物;一种制备所述助剂的方法,其中使极性溶剂和式(A)的磷酸酯接触;所述助剂在提高农药活性中的用途;以及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法,其中使该组合物作用于相应有害物、其环境或待防止相应有害物的作物、土壤和/或不希望的植物和/或作物和/或其环境。本发明包括优选特征与其他优选特征的组合。
包含磷酸酯的助剂和农化配制剂是已知的:
WO2007/115944公开了一种咪唑啉酮除草剂用助剂,其包含单羟基官能的聚烷基醚的磷酸酯。WO2001/67860公开了一种农用配制剂,其包含环己烷多羧酸酯和辅助剂和/或添加剂如聚环氧烷醚的磷酸酯或二甲亚砜(DMSO)。WO2010/040835公开了一种液体配制剂,其包含唑菌胺酯(pyraclostrobin)、在水中溶解度为至少2g/L的有机溶剂LM2(例如DMSO)和阴离子表面活性物质OS1(例如低聚-C2-C3氧化烯C8-C22烷基醚磷酸酯)。
已知助剂和农化配制剂的缺点尤其为对农药的活性提高作用能够改进,活性提高作用大大改变和难以将助剂掺入农化配制剂中(即例如可导致储存稳定性降低)。
本发明目的为提供一种助剂和一种农化组合物,其克服了这些缺点。
该目的通过提高农药活性的助剂实现,其包含极性溶剂和式(A)的磷酸酯:
其中Ra为R1-O-(CnH2nO)x-(CmH2mO)y-,
Rb为R1-O-(CnH2nO)x-(CmH2mO)y-或OH,
R1为C6-C30烷基,
n、m相互独立地为2-6的值,
x、y相互独立地为0-100的值,
x+y给出1-100的值,和
其中式(A)的磷酸酯可作为游离酸和/或作为盐存在,并且其中极性溶剂与水以任意比例混溶且具有超过60℃的闪点。
Rb优选为OH。
在尤其优选的变型中,式(A)的磷酸酯可为其中在混合物的部分T1中Rb为OH且在混合物的其余部分T2中Rb为R1-O-(CnH2nO)x-(CmH2mO)y-的混合物。混合物通常包含0.5-50重量%,优选1-20重量%,尤其优选1-10重量%T2,其中混合物其余部分为T1。
R1可为线性或支化烷基。R1优选为未取代的脂族烷基。R1优选为C8-C18烷基,尤其优选C10-C16烷基,例如癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基或十六烷基。
指数n和m优选相互独立地为2-5的值,尤其优选2-4的值,特别是2或3的值。指数n和m通常呈现不同的值。指数n和m通常呈现为整数的值。
指数x和y优选相互独立地为0-40的值,尤其优选0-25的值,特别是1-20的值。
x+y总和优选给出3-50的值,尤其优选6-30的值,特别是10-25的值。
在优选的实施方案中,n为2,x为3-30,m为3,y为0-20和x+y为4-30。
在基团“R1-O-(CnH2nO)x-(CmH2mO)y-”中,烷氧基单元“(CnH2nO)x”和“(CmH2mO)y”可以任意顺序存在,例如为无规分布的或为嵌段的(例如A-B或A-B-A)。
在另一优选的实施方案中,R1为C8-C18烷基,n和m相互独立地为2-4的值,x和y相互独立地为1-25的值且x+y给出3-50的值。
在尤其优选的实施方案中,R1为C8-C18烷基,n和m相互独立地为2或3的值,x和y相互独立地为1-20的值且x+y给出6-30的值。
式(A)的磷酸酯可作为游离酸(例如RaRbP(O)OH)和/或作为盐(例如RaRbP(O)O-,具有抗衡离子)存在。在盐形式的磷酸酯中,其包含常规抗衡离子,例如碱金属或碱土金属的阳离子、铵、(2-羟乙基)三甲基铵、胍、三乙醇铵、乙醇铵、二甲基铵或二甘醇铵。磷酸酯优选作为游离酸存在。
式(A)的磷酸酯及其制备通常例如由Wasow,SurfactantScienceSeries,第56卷(AnionicSurfactants:OrganicChemistry),1995,第10.2章(Polyoxyalkylenephosphateesters),第560-564页已知。
极性溶剂与水以任意比例混溶且具有超过60℃的闪点。该类溶剂的实例通常是已知的且可由熟练技术人员在教科书中找到。特别好的实例为N-甲基吡咯烷酮或DMSO。
术语“与水以任意比例混溶”意指可在20℃下制备任意重量比的水与极性溶剂而在24小时内不导致相分离。
闪点通常在1013毫巴下测定且优选超过65℃,尤其优选超过70℃,尤其优选超过75℃,特别是超过80℃。闪点可如DIN51758,EN22719所规定测定。
在另一实施方案中,极性溶剂优选具有至少一个(例如一个或两个)亚砜基团或砜基团,其中更优选亚砜基团。实例为二甲亚砜(DMSO)或环丁砜。
最合适的极性溶剂为DMSO。
本发明助剂通常包含至少5重量%,优选至少20重量%,特别是至少30重量%式(A)的磷酸酯。在另一变型中,本发明助剂通常包含至少31重量%,优选至少33重量%,特别是至少35重量%式(A)的磷酸酯。助剂可包含不大于90重量%,优选不大于75重量%,特别是不大于50重量%磷酸酯。
二甲亚砜(DMSO)是通常已知的有机溶剂。本发明助剂通常包含至少5重量%,优选至少30重量%,,特别是至少50重量%极性溶剂(例如二甲亚砜)。在另一变型中,本发明助剂通常包含至少60重量%,优选至少62重量%,,特别是至少65重量%极性溶剂(例如二甲亚砜)。助剂可包含不大于95重量%,优选不大于85重量%,特别是不大于75重量%极性溶剂(例如DMSO)。
助剂中极性溶剂(例如DMSO)与式(A)的磷酸酯的重量比通常为9.7:0.3-1:9,优选9:1-3:7,尤其优选8.5:1.5-4:6,特别是8:2-5:5。
助剂可包含其他常规农化辅助剂,例如其他有机溶剂或表面活性剂。助剂优选包含至少一种阴离子表面活性剂。合适的阴离子表面活性剂为磺酸、硫酸、磷酸或羧酸的碱金属、碱土金属或铵盐,其中优选磺酸盐。磺酸盐的实例是烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、木素磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例是脂肪酸和油的硫酸盐、乙氧基化烷基酚的硫酸盐、醇的硫酸盐、乙氧基化醇的硫酸盐或脂肪酸酯的硫酸盐。磷酸盐的实例是磷酸盐酯。羧酸盐的实例是烷基羧酸盐和羧化醇乙氧基化物或烷基酚乙氧基化物。
本发明助剂通常包含至少0.5重量%,优选至少1重量%,,特别是至少2重量%阴离子表面活性剂。助剂可包含不大于30重量%,优选不大于15重量%,特别是不大于7重量%阴离子表面活性剂。
本发明助剂通常包含不大于20重量%水,优选不大于5重量%,特别是不大于1重量%水。
本发明助剂通常包含不大于5重量%,优选不大于1重量%,特别是不大于0.1重量%农药。在另一优选的变型中,助剂不含农药,例如下文描述的农药。
在优选的实施方案中,助剂包含20-75重量%式(A)的磷酸酯,30-85重量%极性溶剂(例如DMSO)和任选1-15重量%阴离子表面活性剂。在尤其优选的实施方案中,助剂包含30-50重量%式(A)的磷酸酯,50-75重量%极性溶剂(例如DMSO)和任选2-7重量%阴离子表面活性剂。
本发明助剂通常为液体或固体,优选液体。固体配制剂的实例为类似于WO2007/028504或WO2007/028505中的固体配制剂的那些。农化配制剂的固体类型的优选实例在下文描述于项目“vi)水分散性颗粒(WG)”和“vii)水分散性粉末(WP)”下。本发明助剂优选为液体,尤其是溶液、乳液、悬浮液或悬浮乳液。助剂尤其优选为溶液。
本发明另一主题为一种制备本发明助剂的方法,其中使极性溶剂与式(A)的磷酸酯接触,例如通过以任意顺序混合各组分而进行。
本发明另一主题为本发明助剂在提高农药,尤其是除草剂活性中的用途。合适的农药如下文描述。
本发明另一主题涉及包含农药和本发明助剂的农化组合物。
术语农药是指至少一种选自如下的活性物质:杀真菌剂、杀虫剂、杀线虫剂、除草剂、安全剂和/或生长调节剂。优选的农药为杀真菌剂、杀虫剂、除草剂和生长调节剂。尤其优选的农药为除草剂。也可使用来自两个或更多个上述类别的农药的混合物。熟练技术人员熟悉该类农药,其可例如在PesticideManual,第15版(2009),TheBritishCropProtectionCouncil,London中找到。例如以下农药是合适的(农药A)-K)为杀真菌剂):A)呼吸抑制剂
-在Qo位点的配合物III抑制剂(例如嗜球果伞素类):腈嘧菌酯(azoxystrobin)、甲香菌酯(coumethoxylstrobin)、丁香菌酯(coumoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、烯肟菌胺(fenaminstrobin)、fenoxystrobin/氟菌螨酯(flufenoxystrobin)、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、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、肟菌酯(trifloxystrobin)、2-[2-(2,5-二甲基苯氧基甲基)苯基]-3-甲氧基丙烯酸甲酯、2-(2-(3-(2,6-二氯苯基)-1-甲基亚烯丙基氨基氧甲基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺、pyribencarb、氧啶菌酯(triclopyricarb)/chlorodincarb、唑酮菌(famoxadon)、咪唑菌酮(fenamidon);
-在Qi位点的配合物III抑制剂:氰霜唑(cyazofamid)、amisulbrom;
-配合物II抑制剂(例如羧酰胺类):麦锈灵(benodanil)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、氟吡菌酰胺(fluopyram)、氟酰胺(flutolanil)、氟唑菌酰胺(fluxapyroxad)、呋吡唑灵(furametpyr)、isopyrazam、丙氧灭绣胺(mepronil)、氧化萎锈灵(oxycarboxin)、penflufen、吡噻菌胺(penthiopyrad)、sedaxane、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、N-(4'-三氟甲硫基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(2-(1,3,3-三甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-甲酰胺和N-[9-(二氯亚甲基)-1,2,3,4-四氢-1,4-甲撑萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺;
-其他呼吸抑制剂(例如配合物I,去偶剂):二氟林(diflumetorim);硝基苯基衍生物:乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、氟啶胺(fluazinam);嘧菌腙(ferimzone);有机金属化合物:三苯锡基盐,例如薯瘟锡(fentin-acetate)、三苯锡氯(fentinchloride)或毒菌锡(fentinehydroxide);ametoctradin;和硅噻菌胺(silthiofam);
B)甾醇生物合成抑制剂(SBI杀真菌剂)
-C14去甲基化抑制剂(DMI杀真菌剂):三唑类:戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇M(diniconazole-M)、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)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、oxpoconazole、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、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)、戊叉唑菌(triticonazole)、烯效唑(uniconazole);咪唑类:烯菌灵(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole);嘧啶类、吡啶类和哌嗪类:异嘧菌醇(fenarimol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine);
-δ14-还原酶抑制剂:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸酯(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph)、苯锈啶(fenpropidin)、粉病灵(piperalin)、螺茂胺(spiroxamine);
-3-酮基还原酶抑制剂:环酰菌胺(fenhexamid);
C)核酸合成抑制剂
-苯基酰胺或酰基氨基酸杀真菌剂:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-m)、kiralaxyl、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)(mefenoxam)、甲呋酰胺(ofurace)、霜灵(oxadixyl);
-其他:土菌消(hymexazole)、异噻菌酮(octhilinone)、恶喹酸(oxolinicacid)、磺嘧菌灵(bupirimate);
D)细胞分裂和细胞骨架抑制剂
-微管蛋白抑制剂,如苯并咪唑类、托布津类(thiophanate):苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole)、甲基托布津(thiophanate-methyl);三唑并嘧啶类: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;
-其他细胞分裂抑制剂:乙霉威(diethofencarb)、噻唑菌胺(ethaboxam)、戊菌隆(pencycuron)、氟吡菌胺(fluopicolid)、苯酰菌胺(zoxamid)、苯菌酮(metrafenon)、pyriofenon;
E)氨基酸合成和蛋白合成抑制剂
-蛋氨酸合成抑制剂(苯胺基嘧啶类):环丙嘧啶(cyprodinil)、嘧菌胺(mepanipyrim)、二甲嘧菌胺(pyrimethanil);
-蛋白合成抑制剂:灭瘟素(blasticidin-S)、春雷素(kasugamycin)、水合春雷素(kasugamycinhydrochloridehydrate)、米多霉素(mildiomycin)、链霉素(streptomycin)、土霉素(oxytetracyclin)、多氧霉素(polyoxin)、井冈霉素(validamycinA);
F)信号传导抑制剂
-MAP/组胺酸激酶抑制剂:氟菌安(fluoroimide)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin)、拌种咯(fenpiclonil)、氟菌(fludioxonil);
-G蛋白抑制剂:喹氧灵(quinoxyfen);
G)类脂和膜合成抑制剂
-磷脂生物合成抑制剂:克瘟散(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、稻瘟灵(isoprothiolane);
-类脂过氧化:氯硝胺(dicloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl)、联苯、地茂散(chloroneb)、氯唑灵(etridiazole);
-磷脂生物合成和细胞壁附着:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、双炔酰菌胺(mandiproamid)、丁吡吗啉(pyrimorph)、苯噻菌胺(benthiavalicarb)、异丙菌胺(iprovalicarb)、valifenalate和N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸(4-氟苯基)酯;
-影响细胞膜渗透性的化合物和脂肪酸:百维灵(propamocarb)、霜霉威盐酸盐(propamocarbhydrochloride);
H)“多位点”抑制剂
-无机活性物质:波尔多液(Bordeaux混合物),醋酸铜,氢氧化铜,王铜(copperoxychloride),碱式硫酸铜,硫;
-硫代-和二硫代氨基甲酸盐:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-有机氯化合物(例如邻苯二甲酰亚胺类、磺酰胺类、氯代腈类):敌菌灵(anilazine)、百菌清(chlorothalonil)、敌菌丹(captafol)、克菌丹(captan)、灭菌丹(folpet)、抑菌灵(dichlofluanid)、双氯酚(dichlorophen)、磺菌胺(flusulfamide)、六氯苯(hexachlorobenzene)、五氯酚(pentachlorphenol)及其盐、四氯苯酞(phthalid)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
-胍类及其他:胍、多果定(dodine)、多果定游离碱、双胍盐(guazatin)、双胍辛胺(guazatin-acetate)、双胍辛醋酸盐(iminoctadin)、双胍辛胺三乙酸盐(iminoctadintriacetate)、双八胍盐(iminoctadintris(albesilate))、二噻农(dithianon);
I)细胞壁生物合成抑制剂
-葡聚糖合成抑制剂:井冈霉素(validamycin)、多氧霉素(polyoxinB);黑色素合成抑制剂:咯喹酮(pyroquilon)、三环唑(tricyclazole)、氯环丙酰胺(carpropamide)、双氯氰菌胺(dicyclomet)、氰菌胺(fenoxanil);
J)抗性诱导剂
-噻二唑素(acibenzolar-S-methyl)、噻菌灵(probenazol)、异噻菌胺(isotianil)、噻酰菌胺(tiadinil)、调环酸钙(prohexadione-calcium);膦酸酯类:藻菌磷(fosetyl)、乙磷铝(fosetyl-aluminum)、亚磷酸及其盐;
K)未知作用模式:
-拌棉醇(bronopol)、灭螨蜢(quinomethionate)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌清(diclomezin)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)、二苯基胺、胺苯吡菌酮(fenpyrazamine)、氟联苯菌(flumetover)、磺菌胺(flusulfamid)、flutianil、磺菌威(methasulfocarb)、氯草定(nitrapyrin)、异丙消(nitrothal-isopropyl)、喹啉铜(oxine-copper)、丙氧喹啉(proquinazid)、tebufloquin、叶枯酞、唑菌嗪(triazoxide)、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺、N'-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N'-(4-(4-氟-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N'-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、N'-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸N-甲基-(1,2,3,4-四氢萘-1-基)酯、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸N-甲基-(R)-1,2,3,4-四氢萘-1-基酯、1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]甲基酮、甲氧基乙酸6-叔丁基-8-氟-2,3-二甲基喹啉-4-基酯、N-甲基-2-{1-[(5-甲基-3-三氟甲基-1H-吡唑-1-基)乙酰基]哌啶-4-基}-N-[(1R)-1,2,3,4-四氢萘-1-基]-4-噻唑甲酰胺、3-[5-(4-甲基苯基)-2,3-二甲基异唑烷-3-基]吡啶、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶(啶菌唑(pyrisoxazol))、N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺、5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑、2-(4-氯苯基)-N-[4-(3,4-二甲氧基苯基)异唑-5-基]-2-丙-2-炔氧基乙酰胺;
M)生长调节剂
-脱落酸(abscisicacid)、先甲草胺(amidochlor)、嘧啶醇(ancymidole)、苄胺基嘌呤(6-benzylaminopurine)、油菜素内酯(brassinolide)、地乐胺(butralin)、矮壮素阳离子(chlormequat)(矮壮素(chlormequatchloride))、氯化胆碱(cholinechloride)、环丙酸酰胺(cyclanilid)、丁酰肼(daminozide)、敌草克(dikegulac)、噻节因(dimethipin)、2,6-二甲基吡啶(2,6-dimethylpuridine)、乙烯利(ethephon)、抑芽敏(flumetralin)、呋嘧醇(flurprimidol)、达草氟(fluthiacet)、调吡脲(forchlorfenuron)、九二O(gibberellicacid)、抗倒胺(inabenfid)、吲哚-3-乙酸、抑芽丹(maleichydrazide)、氟草磺(mefluidid)、环戊唑菌、助壮素阳离子(mepiquat)(助壮素(mepiquatchloride))、环戊唑菌、萘乙酸、N-6-苄基腺嘌呤、多效唑、调环酸(prohexadione)(调环酸钙)、茉莉酸丙酯(prohydrojasmone)、赛二唑素(thidiazuron)、抑芽唑(triapenthenol)、脱叶磷(tributylphosphorotrithioate)、2,3,5-三碘苯甲酸、抗倒酯(trinexapac-ethyl)和烯效唑;
N)除草剂
-乙酰胺类:乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethenamid)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、异丙甲草胺(metolachlor)、吡草胺(metazachlor)、草萘胺(napropamid)、萘丙胺(naproanilid)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、噻醚草胺(thenylchlor);
-氨基酸类似物:双丙氨酰膦(bilanafos)、草甘膦(glyphosate)、草铵膦(glufosinate)、草硫膦(sulfosate);
-芳氧基苯氧基丙酸酯类:炔草酯(clodinafop)、氰氟草酯(cyhalofop-butyl)、唑禾草灵(fenoxaprop)、吡氟禾草灵(fluazifop)、吡氟氯禾灵(haloxyfop)、恶唑酰草胺(metamifop)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、喹禾灵(四氢糠基酯)(quizalofop-p-tefuryl);
-联吡啶类:敌草快阳离子(diquat)、对草快阳离子(paraquat);
-氨基甲酸酯类和硫代氨基甲酸酯类:黄草灵(asulam)、苏达灭(butylate)、长杀草(carbetamide)、异苯敌草(desmedipham)、哌草丹(dimepiperat)、扑草灭(eptam)(EPTC)、禾草畏(esprocarb)、草达灭(molinate)、坪草丹(orbencarb)、苯敌草(phenmedipham)、苄草丹(prosulfocarb)、稗草畏(pyributicarb)、杀草丹(thiobencarb)、野麦畏(triallate);
-环己二酮类:丁氧环酮(butroxydim)、烯草酮(clethodim)、噻草酮(cycloxydim)、环苯草酮(profoxydim)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)、肟草酮(tralkoxydim);
-二硝基苯胺类:氟草胺(benfluralin)、丁氟消草(ethalfluralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)、氟乐灵(trifluralin);
-二苯基醚类:氟锁草醚(acifluorfen)、苯草醚(aclonifen)、治草醚(bifenox)、氯甲草(diclofop)、氯氟草醚(ethoxyfen)、氟黄胺草醚(fomesafen)、乳氟禾草灵(lactofen)、乙氧氟草醚(oxyfluorfen);
-羟基苄腈类:溴苯腈(bromoxynil)、敌草腈(dichlobenil)、碘苯腈(ioxynil);
-咪唑啉酮类:咪草酯(imazamethabenz)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr);
-苯氧基乙酸类:稗草胺(clomeprop)、2,4-二氯苯氧基乙酸(2,4-D)、2,4-DB、2,4-滴丙酸(dichlorprop)、MCPA、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB、2甲4氯丙酸(mecoprop);
-吡嗪类:杀草敏(chloridazon)、氟哒嗪草酯(flufenpyr-ethyl)、达草氟、达草灭(norflurazon)、达草止(pyridate);
-吡啶类:氨草啶(aminopyralid)、二氯皮考啉酸(clopyralid)、吡氟草胺(diflufenican)、氟硫草定(dithiopyr)、氟草同(fluridone)、氟草烟(fluroxypyr)、毒莠定(picloram)、氟吡酰草胺(picolinafen)、噻氟啶草(thiazopyr);
-磺酰脲类:磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、环丙黄隆(cyclosulfamuron)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟啶黄隆(flupyrsulfuron)、酰胺磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、啶咪黄隆(imazosulfuron)、甲基碘磺隆(iodosulfuron)、甲磺胺磺隆(mesosulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、环丙氧黄隆(oxasulfuron)、氟嘧黄隆(primisulfuron)、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、乙黄黄隆(sulfosulfuron)、噻黄隆(thifensulfuron)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、三氟甲磺隆(tritosulfuron)、1-((2-氯-6-丙基咪唑并[1,2-b]哒嗪-3-基)磺酰基)-3-(4,6-二甲氧基嘧啶-2-基)脲;
-三嗪类:莠灭净(ametryne)、莠去津(atrazine)、草净津(cyanazine)、戊草津(dimethametryne)、乙嗪草酮(ethiozine)、六嗪同(hexazinone)、苯嗪草(metamitron)、赛克津(metribuzine)、扑草净(prometryne)、西玛津(simazine)、特丁津(terbuthylazine)、去草净(terbutryne)、苯氧丙胺津(triaziflam);
-脲类:绿麦隆(chlortoluron)、香草隆(daimuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、利谷隆(linuron)、噻唑隆(methabenzthiazuron)、丁唑隆(tebuthiuron);
-其他乙酰乳酸合成酶抑制剂:双草醚钠盐(bispyribac-sodium)、氯酯磺草胺(cloransulam-methyl)、唑嘧磺胺(diclosulam)、双氟磺草胺(florasulam)、氟酮磺隆(flucarbazone)、氟唑啶草(flumetsulam)、唑草磺胺(metosulam)、嘧苯胺磺隆(orthosulfamuron)、五氟磺草胺(penoxsulam)、丙氧基卡巴腙(propoxycarbazone)、丙酯草醚(pyribambenz-propyl)、嘧苯草肟(pyribenzoxim)、环酯草醚(pyriftalide)、肟啶草(pyriminobac-methyl)、pyrimisulfan、嘧硫苯甲酸(pyrithiobac)、pyroxasulfon、甲氧磺草胺(pyroxsulam);
-其他:胺唑草酮(amicarbazone)、三唑胺(aminotriazole)、莎稗磷(anilofos)、beflubutamid、草除灵(benazolin)、bencarbazone、benfluresate、吡草酮(benzofenap)、噻草平(bentazone)、苯并双环酮(benzobicyclon)、除草定(bromacil)、溴丁酰草胺(bromobutide)、氟丙嘧草酯(butafenacil)、草胺磷(butamifos)、胺草唑(cafenstrole)、氟酮唑草(carfentrazone)、吲哚酮草酯(cinidon-ethyyl)、敌草索(chlorthal)、环庚草醚(cinmethylin)、异恶草酮(clomazone)、苄草隆(cumyluron)、cyprosulfamid、麦草畏(dicamba)、苯敌快(difenzoquat)、二氟吡隆(diflufenzopyr)、稗内脐蠕孢菌(Drechsleramonoceras)、敌草腈(endothal)、乙呋草黄(ethofumesate)、乙苯酰草(etobenzanid)、四唑酰草胺(fentrazamide)、氟烯草酸(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、胺草唑(flupoxam)、氟咯草酮(fluorochloridon)、呋草酮(flurtamon)、茚草酮(indanofan)、异恶草胺(isoxaben)、异氟草(isoxaflutol)、环草定(lenacil)、敌稗(propanil)、拿草特(propyzamide)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、硝草酮(mesotrione)、甲胂酸(methylarsonicacid)、抑草生(naptalam)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazone)、氯嗪草(oxaziclomefon)、戊唑草(pentoxazone)、唑啉草酯(pinoxaden)、双唑草腈(pyraclonil)、吡草醚(pyraflufen-ethyl)、pyrasulfotol、苄草唑(pyrazoxyfen)、吡唑特(pyrazolynate)、灭藻醌(quinoclamin)、嘧啶肟草醚(saflufenacil)、磺草酮(sulcotrione)、磺胺草唑(sulfentrazone)、特草定(terbacil)、tefuryltrione、tembotrione、thiencarbazone、topramezone、4-羟基-3-[2-(2-甲氧基乙氧基甲基)-6-三氟甲基吡啶-3-羰基]双环[3.2.1]辛-3-烯-2-酮、(3-[2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-2H-嘧啶-1-基)苯氧基]吡啶-2-基氧基)乙酸乙酯、6-氨基-5-氯-2-环丙基嘧啶-4-甲酸甲酯、6-氯-3-(2-环丙基-6-甲基苯氧基)哒嗪-4-醇、4-氨基-3-氯-6-(4-氯苯基)-5-氟吡啶-2-甲酸、4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-甲酸甲酯和4-氨基-3-氯-6-(4-氯-3-二甲基氨基-2-氟苯基)吡啶-2-甲酸甲酯;
O)杀虫剂
-有机(硫代)磷酸酯:高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基对硫磷(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、田乐磷(sulprophos)、杀虫威(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
-氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
-合成除虫菊酯类:丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(lambda-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊(pyrethrin)I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
-昆虫生长抑制剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(chlorfluazuron)、灭蝇胺(cyramazin)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、四螨嗪(clofentazin);b)蜕皮激素拮抗剂:特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威;d)类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramate);
-烟碱受体激动剂/拮抗剂:噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、吡虫清(acetamiprid)、噻虫啉(thiacloprid)、1-(2-氯噻唑-5-基甲基)-2-硝酰亚氨基(nitrimino)-3,5-二甲基-[1,3,5]三嗪烷(triazinane);
-GABA拮抗剂:硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、N-5-氨基-1-(2,6-二氯-4-甲基苯基)-4-亚磺酰氨酰基(sulfinamoyl)-1H-吡唑-3-硫代甲酰胺;
-大环内酯:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad)、乙基多杀菌素(spinetoram);
-线粒体电子传输链抑制剂(METI)I杀螨剂:喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、嘧虫胺(flufenerim);
-METIII和III物质:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnone);
-去偶剂:氟唑虫清(chlorfenapyr);
-氧化磷酸化抑制剂:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatinoxide)、克螨特(propargite);
-昆虫蜕皮抑制剂:灭蝇胺(cryomazine);
-‘混合功能氧化酶’抑制剂:增效醚(piperonylbutoxide);
-钠通道阻断剂:二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
-其他:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozin)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、氯虫酰胺(chlorantraniliprole)、cyazypyr(HGW86);cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、imicyafos、双三氟虫脲(bistrifluron)和pyrifluquinazone。
优选的农药包含至少一种N)类除草剂,尤其优选草甘膦、草铵膦、植物生长素类除草剂、ALS抑制剂类除草剂、漂白剂类除草剂或原卟啉原-IX氧化酶抑制剂类除草剂。非常尤其优选的农药包含咪唑啉酮类,例如咪草酯、咪草啶酸、甲基咪草烟、灭草烟、灭草喹和咪草烟。
农药可以固体、溶解、悬浮、乳化或悬浮乳化形式存在。优选至少一种农药以溶解形式存在。
农药可为水溶性的或水不溶性的。优选至少一种农药为水溶性的。水溶性农药通常在水中在20℃以至少0.2重量%,优选至少0.5重量%,尤其优选至少2重量%,特别是至少5重量%可溶。
农化组合物还可包含肥料,例如无机硫酸盐、无机磷酸盐或无机硝酸盐。实例为硫酸铵、硝酸铵或磷酸铵。农化组合物还可包含微量营养素,例如含铜或锌化合物。
本发明农化组合物通常包含至少0.5重量%,优选至少1.0重量%农药。农化组合物可包含不大于99重量%,优选不大于80重量%,特别是不大于60重量%农药。
本发明农化组合物通常包含至少5重量%,优选至少20重量%,特别是至少30重量%式(A)的磷酸酯。在另一变型中,本发明农化组合物通常包含至少31重量%,优选至少35重量%,特别是至少40重量%式(A)的磷酸酯。农化组合物可包含不大于90重量%,优选不大于75重量%,特别是不大于50重量%磷酸酯。
本发明农化组合物通常包含至少5重量%,优选至少30重量%,特别是至少50重量%极性溶剂(例如二甲亚砜)。在另一变型中,本发明农化组合物通常包含至少60重量%,优选至少65重量%,特别是至少70重量%极性溶剂(例如二甲亚砜)。农化组合物可包含不大于95重量%,优选不大于85重量%,特别是不大于75重量%极性溶剂(例如DMSO)。
农化组合物中极性溶剂(例如二甲亚砜)与式(A)的磷酸酯的重量比通常为9.7:0.3-1:9,优选9:1-3:7,尤其优选8.5:1.5-4:6,特别是8:2-5:5。
本发明农化组合物通常为液体或固体,优选液体。固体配制剂的实例为类似于WO2007/028504或WO2007/028505中的固体配制剂的那些。农化配制剂的固体类型的优选实例在下文描述于项目“vi)水分散性颗粒(WG)”和“vii)水分散性粉末(WP)”下。本发明农化组合物优选为液体,尤其是溶液、乳液、悬浮液或悬浮乳液。组合物尤其优选为溶液。
此外,农化组合物也可包含常用于植物保护产品的辅助剂,其中辅助剂的选择取决于特定使用形式或活性物质。合适辅助剂的实例为其他溶剂,固体载体,表面活性物质(例如表面活性剂、增溶剂、保护性胶体、润湿剂和粘合剂),有机和无机增稠剂,杀菌剂,防冻剂,消泡剂,任选着色剂以粘着剂(例如用于处理种子)。
合适的其他溶剂为水,有机溶剂如中沸点到高沸点的矿物油馏分如煤油和柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,二醇类,酮类如环己酮、γ-丁内酯,二甲基脂肪酸酰胺、脂肪酸和脂肪酸酯,和强极性溶剂,例如酰胺类如N-甲基吡咯烷酮。原则上也可以使用溶剂混合物。优选的其他溶剂为有机溶剂。
本发明农化组合物通常包含不大于20重量%水,优选不大于5重量%水,特别是不大于1重量%水。
固体载体为矿土如硅石、硅胶、硅酸盐、沉淀二氧化硅(例如Sipernat类型如Sipernat50S)、滑石、高岭土、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,脲类以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉或其他固体载体。
合适的表面活性物质(助剂、润湿剂、粘合剂、分散剂或乳化剂)是芳族磺酸如木素磺酸(类型,Borregaard,挪威)、苯酚磺酸、萘磺酸(类型,AkzoNobel,美国)和二丁基萘磺酸(类型,BASF,德国)以及脂肪酸的碱金属盐、碱土金属盐、铵盐,烷基-和烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,还有脂肪醇乙二醇醚的盐,磺化萘及其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,聚氧乙烯辛基酚醚,乙氧基化异辛基-、辛基-或壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸盐废液和蛋白质,变性蛋白质,多糖(如甲基纤维素),疏水改性的淀粉,聚乙烯醇(类型,Clariant,瑞士),聚羧酸盐类(类型,BASF,德国),聚烷氧基化物,聚乙烯胺(类型,BASF,德国),聚乙烯亚胺(类型,BASF,德国),聚乙烯基吡咯烷酮及其共聚物。
合适的表面活性剂特别是阴离子、阳离子、非离子和两性表面活性剂,嵌段聚合物和聚电解质。合适的阴离子表面活性剂如上文提及。
合适的非离子表面活性剂是烷氧基化物,N-烷基化脂肪酸酰胺,胺氧化物,酯或糖基表面活性剂。烷氧基化物的实例是诸如已经烷氧基化的醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯的化合物。可以用于烷氧基化的物质为氧化乙烯和/或氧化丙烯,优选氧化乙烯。N-烷基化脂肪酸酰胺的实例是脂肪酸葡糖酰胺或脂肪酸链烷醇酰胺。酯的实例是脂肪酸酯、甘油酯或甘油单酯。糖基表面活性剂的实例是脱水山梨醇、乙氧基化脱水山梨醇、蔗糖酯和葡萄糖酯或烷基聚葡糖苷。
合适的阳离子表面活性剂是季表面活性剂,例如具有一个或两个疏水性基团的季铵化合物,或长链伯胺的盐。合适的两性表面活性剂是烷基甜菜碱和咪唑啉类。合适的嵌段聚合物是包含聚氧乙烯和聚氧丙烯的嵌段的A-B或A-B-A类型嵌段聚合物或包含链烷醇、聚氧乙烯和聚氧丙烯的A-B-C类型嵌段聚合物。合适的聚电解质是聚酸或聚碱。聚酸的实例是聚丙烯酸的碱金属盐。聚碱的实例是聚乙烯基胺或聚乙烯胺。
农化组合物优选包含至少一种阴离子表面活性剂。农化组合物通常包含至少0.5重量%,优选至少1重量%,特别是至少2重量%阴离子表面活性剂。组合物可包含不大于30重量%,优选不大于15重量%,特别是不大于7重量%阴离子表面活性剂。
农化组合物尤其优选包含至少一种阴离子表面活性剂和至少一种非离子表面活性剂。农化组合物通常包含至少3重量%,优选至少10重量%,特别是至少20重量%非离子表面活性剂。组合物可包含不大于50重量%,优选不大于40重量%,特别是不大于30重量%非离子表面活性剂。合适的阴离子和非离子表面活性剂在上文提及。
增稠剂(即赋予该组合物以改变的流动行为,即静止时的高粘度和搅动状态下的低粘度的化合物)的实例是多糖以及有机和无机层状矿物如黄原胶(CPKelco,美国),23(Rhodia,法国)或(R.T.Vanderbilt,美国)或(EngelhardCorp.,NJ,美国)。
可以加入杀菌剂以稳定该组合物。杀菌剂的实例是基于双氯酚和苄醇半缩甲醛的那些(ICI的或ThorChemie的RS以及Rohm&Haas的MK)以及异噻唑啉酮衍生物如烷基异噻唑啉酮类和苯并异噻唑啉酮类的那些(ThorChemie的MBS)。
合适防冻剂的实例是乙二醇、丙二醇、尿素和甘油。
消泡剂的实例是聚硅氧烷乳液(例如SRE,德国Wacker或法国Rhodia),长链醇,脂肪酸,脂肪酸盐,有机氟化合物及其混合物。
着色剂的实例是微水溶性颜料和水溶性染料二者。可以提到的实例是由如下名称已知的染料和颜料:若丹明B、C.I.颜料红112和C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粘着剂的实例是聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤维素醚(,日本Shin-Etsu)。
组合物类型的实例为悬浮液(SC、OD、FS),可乳化浓缩物(EC),乳液(EW、EO、ES),糊,丸剂,可湿性粉末或粉剂(WP、SP、SS、WS、DP、DS)或可溶解或分散(可湿性)于水中的颗粒(GR、FG、GG、MG)以及用于处理植物繁殖材料如种子的凝胶(GF)。农化组合物以已知方式制备(例如Mollet,H.和Grubemann,A.:Formulationtechnology(WileyVCHVerlag,Weinheim,2001)。
农化配制剂类型的实例为:
1.在水中稀释的组合物类型
i)水溶性浓缩物(SL、LS)
将10重量份水溶性活性物质溶于80重量份本发明助剂中并用10%润湿剂处理。这得到活性物质含量为10重量%的组合物。
ii)分散性浓缩物(DC)
将20重量份本发明助剂和任选农药溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。在水中稀释得到分散体。活性物质含量为20重量%。
iii)可乳化浓缩物(FC)
将15重量份本发明助剂和任选农药溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。在水中稀释得到乳液。该组合物的活性物质含量为15重量%。
iv)乳液(EW、EO、ES)
将25重量份本发明助剂和任选农药溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。使用乳化机装置(例如Ultra-Turrax)将该混合物置于30重量份水中并制成均相乳液。在水中稀释得到乳液。该组合物的活性物质含量为25重量%。
v)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份本发明助剂和任选农药粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性物质悬浮液。在水中稀释得到稳定的活性物质悬浮液。该组合物中活性物质含量为20重量%。
vi)水分散性颗粒(WG)
将50重量份本发明助剂在吸收性载体(例如Sipernat50S)上的被吸收物细碎研磨并加入50重量份载体、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。在水中稀释得到稳定的活性物质分散体或溶液。
vii)水分散性粉末(WP)
将50重量份本发明助剂在吸收性载体(例如Sipernat50S)上的被吸收物在转子-定子磨机中研磨并加入25重量份载体、分散剂、湿润剂和硅胶。在水中稀释得到稳定的活性物质分散体或溶液。
viii)凝胶(GF)
在球磨机中研磨20重量份活性物质、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂,得到细悬浮液。在水中稀释得到活性物质含量为20重量%的稳定悬浮液。
2.直接施用的组合物类型
ix)粉剂(DP、DS)
将5重量份本发明助剂和农药在吸收性载体(例如50S)上的被吸收物细碎研磨并与95重量份细碎高岭土充分混合。这得到直接施用的粉剂。
x)颗粒(GR,FG,GG,MG)
将0.5重量本发明助剂和农药在吸收性载体(例如50S)上的被吸收物细碎研磨并结合99.5重量份载体。就此而言的现行方法是挤出、喷雾干燥或流化床方法。这得到直接施用的活性物质含量为0.5重量%的颗粒。
xi)ULV溶液(UL)
将10重量份本发明助剂和农药在吸收性载体(例如50S)上的被吸收物溶于90重量份有机溶剂如二甲苯中。这得到直接施用的活性物质含量为10重量%的组合物。
此外,本发明涉及一种制备本发明农化组合物的方法,其中使农药、极性溶剂(例如二甲亚砜)和式(A)的磷酸酯接触,例如通过以任意顺序混合各组分进行。
为了处理植物繁殖材料,尤其是种子,通常使用水溶性浓缩物(SL)、悬浮液(FS)、粉剂(DS)、水分散性和水溶性粉末(WS、SS)、乳液(ES)、可乳化浓缩物(EC)和凝胶(GF)。这些组合物可以未稀释或优选稀释形式施加至植物繁殖材料,尤其是种子。就此而言,所述组合物可稀释2-10倍,使得待用于拌种混合物的组合物中存在0.01-60重量%,优选0.1-40重量%的活性物质。它们可以在播种之前或期间使用。处理植物繁殖材料,尤其是种子是本领域熟练技术人员已知的且通过将植物繁殖材料撒粉、包衣、造粒、浸泡或浸渍而进行,其中处理优选通过造粒、包衣或撒粉或通过犁沟内处理进行,使得例如种子的早期萌发得以防止。
为了处理种子,优选使用悬浮液。该类组合物通常包含1-800g/L活性物质,1-200g/L表面活性剂,0-200g/L防冻剂,0-400g/L粘合剂,0-200g/L着色剂和溶剂,优选水。
用于植物保护的施用率取决于所需效果的性质为0.001-2kg活性物质/ha,优选0.005-2kg/ha,尤其优选0.05-0.9kg/ha,特别是0.1-0.75kg/ha。当处理植物繁殖材料如种子时,活性物质的用量通常为0.1-1000g/100kg,优选1-1000g/100kg,尤其优选1-100g/100kg,特别是5-100g/100kg植物繁殖材料或种子。当用于保护材料或储存产品中时,活性物质的施用率取决于施用区域和所需效果的性质。在材料保护中常用的施用率例如为0.001g-2kg,优选0.005g-1kg活性物质/立方米被处理材料。
可与农化组合物混合的物质为各种类型的油、润湿剂、除草剂、杀菌剂、其他农药和/或肥料(例如硝酸铵/尿素溶液UAN、硫酸铵AMS),也任选仅在紧临使用前(桶混合)。这些试剂可与本发明组合物以1:100-100:1,优选1:10-10:1的重量比混合。
本发明助剂可与本发明组合物以1:100-100:1,优选1:10-10:1的重量比混合。
本发明还涉及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵袭和/或调节植物生长的方法,其中使该组合物作用于相应有害物、其环境或要防止相应有害物的作物、土壤和/或不希望的植物和/或作物和/或其环境。术语作物还包括已经通过育种、诱变或重组方法修饰的那些植物,包括上市销售或开发中的生物技术农业产品。基因修饰植物是其基因材料已经以在自然条件下不通过杂交、突变或自然重组(即基因材料重组)而发生的方式修饰的植物。这里,通常将一个或多个基因整合到植物的基因材料中以改善植物的性能。这类基因修饰还包括蛋白质、寡肽或多肽的靶向翻译后修饰,例如通过糖基化或结合聚合物如异戊二烯化、乙酰化或法呢基化残基或PEG残基。
本发明优点尤其在于对农药的显著的活性提高作用,活性提高作用在非常窄的限制内这一事实和将助剂掺入农化配制剂中的简单可能性。助剂不仅可非常简单地掺入含水农化配制剂中,而且掺入非水农化配制剂中,所述助剂非常好地被作物耐受,所述助剂具有高的桶混相容性,与所述助剂接触的容器和装置可以简单方式清洁(例如使用水),所述助剂甚至可作为清洁剂用于所用喷雾装置,所述助剂具有低毒性且在环境中可容易地降解。
下列实施例说明本发明而不施加任何限制。
实施例
表面活性剂A:阴离子表面活性剂,pH6-7(5%,在水中),表面张力约29mN/m(0.1%,在水中)。
表面活性剂B:非离子表面活性剂,水溶性,pH5-7(1%,在水中),HLB值15-17。
磷酸酯1:AA270,聚烷氧基化脂肪醇的磷酸酯(游离酸形式),液体,约13重量%水,约10重量%磷酸,酸值200-220mgKOH/g,25℃下动态粘度2.2025mPas,pH(1%,在水中)2.2,表面张力(25℃,0.1%水溶液)28.1达因/cm,由BASFCorporation,美国市购。
实施例1-制备助剂
将350g磷酸酯1和35g表面活性剂A在室温和搅拌下溶解于二甲亚砜(DMSO)中,并将溶液配制成1.0L。溶液为即用型的且为储存稳定的。
实施例2-制备农化配制剂
将如下组分在室温下搅拌至大部分DMSO中并随后用DMSO配制成1.0L:27g/L咪草啶酸、266g/L表面活性剂B、333g/L磷酸酯1和33g/L表面活性剂A。这得到即用型SL配制剂(水溶性浓缩物)的澄清溶液。
实施例3-制备农化配制剂
将如下组分在室温下搅拌至大部分DMSO中并随后用DMSO配制成1.0L:25g/L咪草啶酸、250g/L表面活性剂B、300g/L磷酸酯1和25g/L表面活性剂A。这得到即用型SL配制剂(水溶性浓缩物)的澄清溶液。
实施例4-制备具有噻草酮的桶混物
A)通过将含有10重量%噻草酮的可湿性粉末配制剂(WP)与水混合制备可喷雾桶混物(施用率250L/ha)。制备含有重量比为1:1,6或1,25:1的磷酸酯1和DMSO的助剂并加入桶混物中。噻草酮的施用率为12,5、25、50和100g/ha。DMSO和磷酸酯1的施用率为250和400g/ha或500和400g/ha。
实施例5-制备具有氟锁草醚(acifluorfen-sodium)的桶混物
A)通过将含有100g/L氟锁草醚的水溶性浓缩物配制剂(SL)与水混合制备可喷雾桶混物(施用率250L/ha)。制备含有重量比为1:1,6或1,25:1的磷酸酯1和DMSO的助剂并加入桶混物中。除草剂的施用率为37,5、75、150和300g/ha。DMSO和磷酸酯1的施用率为250和400g/ha或500和400g/ha。
实施例6-制备具有虎威(formesafen-sodium)的桶混物
A)通过将含有100g/L虎威的水溶性浓缩物配制剂(SL)与水混合制备可喷雾桶混物(施用率250L/ha)。制备含有重量比为1:1,6或1,25:1的磷酸酯1和DMSO的助剂并加入桶混物中。除草剂的施用率为35、70、140和280g/ha。DMSO和磷酸酯1的施用率为250和400g/ha或500和400g/ha。
实施例7-制备具有噻草平(bentazone-sodium)的桶混物
A)通过将含有100g/L噻草平的水溶性浓缩物配制剂(SL)与水混合制备可喷雾桶混物(施用率250L/ha)。制备含有重量比为1:1,6或1,25:1的磷酸酯1和DMSO的助剂并加入桶混物中。除草剂的施用率为105、210、420和840g/ha。DMSO和磷酸酯1的施用率为250和400g/ha或500和400g/ha。
实施例8-制备具有topramezone的桶混物
A)通过将含有10重量%topramezon的可湿性粉末配制剂(WP)与水混合制备可喷雾桶混物(施用率250L/ha)。制备含有重量比为1:1,6或1,25:1的磷酸酯1和DMSO的助剂并加入桶混物中。除草剂的施用率为6,25、12,5、25和50g/ha。DMSO和磷酸酯1的施用率为250和400g/ha或500和400g/ha。
实施例9-生物活性
评价对处于生长阶段12-18的藜(Chenopodiumalbum)的生物活性,其在田间试验中生长。在实施例3的SL配制剂的32和40g咪草啶酸/ha的使用率下处理植株并在处理60天后评价效力。
通过相对于未处理对照植株对处理植株评分来评价除草活性。评价等级为0-100%活性。100%活性意指至少植株的地上那些部分完全死亡。相反地,0%活性意指在处理和未处理植株之间不存在区别。表1中结果证实由于添加所述助剂导致活性物质的活性提高。
作为对照,“对照A”含有来自BASFSE的40(含有40g/L咪草啶酸的SL配制剂)和来自BASFSE的(液体助剂)。
表1:活性[%]
使用率(g/ha) | 活性[%] | |
对照A | 32 | 82 |
实施例3 | 32 | 98 |
对照A | 40 | 85 |
实施例3 | 40 | 99 |
实施例10-生物活性
评价对处于生长阶段12-18的豚草(Ambrosiaelatior)、荞麦蔓(Polygonumconvolvulus)、曼陀罗属(Daturaspp.)、苍耳属(Xanthiumsp.)、一年生山靛(Mercurialisannua)和马齿苋(Portulacaoleracea)的生物活性,其在温室中生长。在实施例3的SL配制剂的32和40g咪草啶酸/ha的使用率下处理植株并在处理60天后评价效力。除草活性如实施例9中那样评价并且平均活性由全部植株计算(表2)。
表2:活性[%]
使用率(g/ha) | 活性[%] | |
对照A | 32 | 70 |
实施例3 | 32 | 95 |
对照A | 40 | 77 |
实施例3 | 40 | 95 |
实施例11-生物活性
评价对处于生长阶段12-18的马唐(Digitariasanguinalis)、稗草(Echinochloacrus-galli)、狗尾草(Setariaviridis)和倒刺狗尾草(Setariaverticillata)的生物活性,其在温室中生长。在实施例3的SL配制剂的32和40g咪草啶酸/ha的使用率下处理植株并在处理60天后评价效力。除草活性如实施例9中那样评价并且平均活性由全部植株计算(表3)。
表3:活性[%]
使用率(g/ha) | 活性[%] | |
实施例3 | 32 | 85 |
实施例3 | 40 | 97 |
实施例12-储存稳定性
通过混合25g/L咪草啶酸、助剂A-E和水以得到SL配制剂而制备农化组合物。农化组合物的稳定性以肉眼观察测试。样品A形成澄清溶液(“YES”),而咪草啶酸在B-E中不溶(“NO”),如表4所归纳。仅当样品A-E用水稀释以制备浓度为1重量%咪草啶酸的含水桶混物时,所有桶混物形成溶液。
作为对比,使用助剂DSS15(乙氧基化聚芳基酚硫酸酯的铵盐,CAS59891-11-1,水溶性)或4D384(聚芳基苯基醚硫酸酯的铵盐,水溶性)(均由Rhodia,美国获得)。
表4:
Claims (10)
1.一种农化组合物,其包含农药和助剂,其中所述农药为咪唑啉酮,选自咪草酯、咪草啶酸、甲基咪草烟、灭草烟、灭草喹和咪草烟,并且所述助剂包含极性溶剂和式(A)的磷酸酯:
其中Ra为R1-O-(CnH2nO)x-(CmH2mO)y-,
Rb为R1-O-(CnH2nO)x-(CmH2mO)y-或OH,
R1为C8-C18烷基,
n、m相互独立地为2或3的值,
x、y相互独立地为1-20的值,
x+y给出6-30的值,和
其中式(A)的磷酸酯作为游离酸和/或作为盐存在,并且其中极性溶剂为二甲亚砜或环丁砜。
2.根据权利要求1的组合物,其中农药以溶解形式存在。
3.根据权利要求1的组合物,其包含至少20重量%式(A)的磷酸酯。
4.根据权利要求2的组合物,其包含至少20重量%式(A)的磷酸酯。
5.根据权利要求1-4中任一项的组合物,其包含至少20重量%极性溶剂。
6.根据权利要求1-4中任一项的组合物,其包含不大于20重量%水。
7.根据权利要求5的组合物,其包含不大于20重量%水。
8.根据权利要求1-4中任一项的组合物,其包含非离子表面活性剂。
9.根据权利要求7的组合物,其包含非离子表面活性剂。
10.一种防治不希望的植物生长的方法,其中使根据权利要求1-9中任一项的组合物作用于相应有害物、其环境或待防止相应有害物的作物、土壤和/或不希望的植物和/或作物和/或其环境。
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EP11164529.7 | 2011-05-03 | ||
PCT/EP2012/057579 WO2012150163A1 (en) | 2011-05-03 | 2012-04-25 | Adjuvant comprising dimethylsulfoxide and a phosphate ester |
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CA2939807A1 (en) * | 2014-03-25 | 2015-10-01 | Basf Se | Emulsifiable concentrates comprising topamezone, bromoxynil and a safener |
US20210076670A1 (en) * | 2018-02-23 | 2021-03-18 | Nouryon Chemicals International B.V. | Pesticide suspension concentrate and fertilizer composition therewith |
AR114466A1 (es) * | 2018-04-04 | 2020-09-09 | Fmc Corp | Formulaciones de concentrados emulsionables de fungicidas de sdhi |
CN109644996B (zh) * | 2018-12-10 | 2021-11-16 | 上海惠光环境科技有限公司 | 含井冈霉素a和己唑醇的悬浮剂组合物 |
EA202191652A1 (ru) * | 2018-12-18 | 2022-03-11 | Басф Агрокемикэл Продактс Б.В. | Гербицидные комбинации |
EA202191586A1 (ru) * | 2018-12-18 | 2021-10-19 | Басф Агрокемикэл Продактс Б.В. | Гербицидная композиция |
WO2020126578A1 (en) * | 2018-12-18 | 2020-06-25 | Basf Agrochemical Products B.V. | Herbicidal combinations |
EP3897138A1 (en) * | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal combinations |
EP3897139A1 (en) * | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal combinations |
EA202191655A1 (ru) * | 2018-12-18 | 2021-11-01 | Басф Агрокемикэл Продактс Б.В. | Гербицидные комбинации |
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IL228909A0 (en) | 2013-12-31 |
EA201301228A1 (ru) | 2014-04-30 |
AU2012251751B2 (en) | 2015-06-25 |
AR086247A1 (es) | 2013-11-27 |
EA023255B1 (ru) | 2016-05-31 |
KR101955736B1 (ko) | 2019-03-07 |
GEP20156396B (en) | 2015-11-10 |
ZA201309201B (en) | 2015-04-29 |
RS55172B1 (sr) | 2017-01-31 |
HUE030815T2 (en) | 2017-06-28 |
IL228909A (en) | 2016-09-29 |
JP2014518855A (ja) | 2014-08-07 |
ES2593975T3 (es) | 2016-12-14 |
AU2012251751A1 (en) | 2013-11-28 |
BR112013027964B1 (pt) | 2018-10-09 |
CN103501598A (zh) | 2014-01-08 |
US20140073510A1 (en) | 2014-03-13 |
WO2012150163A1 (en) | 2012-11-08 |
EP2704563B1 (en) | 2016-06-29 |
BR112013027964A2 (pt) | 2016-08-09 |
JP5965475B2 (ja) | 2016-08-03 |
KR20140031277A (ko) | 2014-03-12 |
CA2833503C (en) | 2019-07-16 |
CA2833503A1 (en) | 2012-11-08 |
EP2704563A1 (en) | 2014-03-12 |
PL2704563T3 (pl) | 2016-12-30 |
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