CN105325406A - 包含农业活性成分的经稳定的水包油乳液 - Google Patents
包含农业活性成分的经稳定的水包油乳液 Download PDFInfo
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- CN105325406A CN105325406A CN201510883968.8A CN201510883968A CN105325406A CN 105325406 A CN105325406 A CN 105325406A CN 201510883968 A CN201510883968 A CN 201510883968A CN 105325406 A CN105325406 A CN 105325406A
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- surfactant
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- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
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- 238000006386 neutralization reaction Methods 0.000 description 1
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
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- 238000010186 staining Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002424 termiticide Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
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- 230000010148 water-pollination Effects 0.000 description 1
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及稳定的农业水包油乳液组合物。
Description
本申请是中国申请号为200980111607.4、发明名称为“包含农业活性成分的经稳定的水包油乳液”且申请日为2009年2月4日的专利申请(PCT申请号为PCT/US2009/033098)的分案申请。
相关申请的交叉参考
本申请要求2008年2月4日提交的美国临时专利申请61/063,492和2008年3月7日提交的美国临时专利申请61/068,529的权益，将61/063,492和61/068,529具体引入本申请作为参考。
技术领域
本发明涉及稳定的农业水包油乳液组合物(stable,agriculturaloil-in-wateremulsioncompositions)。
背景技术
液体活性成分或活性成分溶解在溶剂中的浓缩水包油乳液，由于其具有优于其它类型制剂的一些优点，因而通常用于农业组合物(agriculturalcompositions)中。乳液是水基的(water-based)，含有很少或不含有溶剂，并且所述乳液允许活性成分的混合物结合在单一制剂中并与宽范围的包装材料相容。然而，所述农业乳液也具有一些缺点，即它们通常为复合制剂(complexformulation)，该复合制剂需要大量的表面活性剂用于起稳定作用，并且所述复合制剂通常非常粘稠，具有乳滴(emulsionglobule)奥斯特瓦尔德熟化(Oswaldripening)的倾向并随时间而分离。因此，农业领域需要对所述乳液制剂进行改进。
在如下专利中已经描述了用于美容和皮肤病学应用的数种水包油乳液组合物：美国专利5,658,575；5,925,364；5,753,241；5,925,341；6,066,328；6,120,778；6,126,948；6,689,371；6,419,946；6,541,018；6,335,022；6,274,150；6,375,960；6,464,990；6,413,527；6,461,625；和6,902,737；将所有这些专利具体引入本申请作为参考。然而，尽管已经发现这些类型的乳液在个人护理产品具有有益的用途，但这些类型的乳液目前还没有与农业活性化合物一起使用，这是因为农业活性化合物在乳液中通常以比美容活性成分更高的水平存在。
适于如下农业活性成分的农业水包油乳液组合物的一个实例在美国专利申请11/495,228中披露，所述农业活性成分在相关储藏温度为液体或可溶于合适的溶剂中，将11/495,228具体引入本申请作为参考。
本发明涉及包含水包油乳液的农业组合物，所述水包油乳液组合物具有油相和水相，所述水包油乳液组合物包含适于形成平均粒径小于800纳米的油滴(oilyglobule)的油、与油相相容的聚合物改性剂、至少一种农业活性化合物、至少一种非离子亲脂性表面活性剂、至少一种非离子亲水表面活性剂、至少一种离子表面活性剂和水。
发明内容
本发明的一个实施方案为新水包油乳液组合物，其具有油相和水相，所述水包油乳液组合物包含:
适于形成平均粒径小于800纳米的油滴的油；
与所述油相相容的聚合物改性剂；
至少一种农业活性化合物；
至少一种非离子亲脂性表面活性剂；
至少一种非离子亲水性表面活性剂；
至少一种离子表面活性剂；和
水。
本发明水包油乳液的油相使用呈油形式的农业活性化合物，或可选择地，使用溶解在油中或混合在油中的农业活性化合物，由此形成油滴。将油定义为不与水混溶的液体。任意与农业活性化合物相容的油可用在本发明的水包油乳液中。术语“相容的”是指所述油会溶解所述农业活性化合物或与农业活性化合物均匀混合并容许形成本发明水包油乳液的油滴。示例性油包括但不限于短链脂肪酸甘油三酯、硅油、石油馏分或烃例如重质芳族石脑油溶剂(heavyaromaticnaphthasolvents)、轻质芳族石脑油溶剂(lightaromaticnaphthasolvents)、加氢处理的轻质石油馏出物(hydrotreatedlightpetroleumdistillates)、石蜡烃族溶剂、矿物油、烷基苯、石蜡油等；植物油例如豆油(soyoil)、菜籽油、椰子油、棉籽油、棕榈油、大豆油(soybeanoil)等；烷基化植物油和脂肪酸的烷基酯例如油酸甲酯等。
在本申请中，将农业活性化合物定义为显示出某种杀虫或杀生物活性的任意油溶性化合物、疏水性化合物或熔点低于约95℃或更低的固体化合物。当所述活性化合物为油时，或可选择地，当所述活性化合物溶解在合适的聚合物改性剂的油中时，应当将所述活性化合物理解为是指活性化合物本身。所述化合物或杀虫剂包括杀真菌剂(fungicide)、杀昆虫剂(insecticide)、杀线虫剂(nematocide)、杀螨剂(miticide)、驱蚁剂(termiticide)、杀啮齿动物剂(rodenticide)、杀节肢动物剂(arthropodicide)、除草剂(herbicide)、杀生物剂(biocide)等。所述农业活性成分的实例可在ThePesticideManual(第12版)中找到。可用在本发明水包油乳液中的示例性杀虫剂包括但不限于苯并呋喃基甲基氨基甲酸酯类杀虫剂(benzofuranylmethylcarbamateinsecticide)例如丙硫克拜威(benfuracarb)和丁硫克百威(carbosulfan)；肟氨基甲酸酯类杀虫剂(oximecarbamateinsecticide)例如涕灭威(aldicarb)；熏蒸杀虫剂(fumigantinsecticide)例如氯化苦(chloropicrin)、1,3-二氯丙烯(1,3-dichloropropene)和溴甲烷(methylbromide)；保幼激素模拟物(juvenilehormonemimic)例如双氧威(fenoxycarb)；有机磷酸酯杀虫剂(organophosphateinsecticide)例如敌敌畏(dichlorvos)；脂肪族有机硫代磷酸酯杀虫剂(aliphaticorganothiophosphateinsecticide)例如马拉硫磷(malathion)和特丁磷(terbufos)；脂肪族酰胺有机硫代磷酸酯杀虫剂(aliphaticamideorganothiophosphateinsecticide)例如乐果(dimethoate)；苯并三嗪有机硫代磷酸酯杀虫剂(benzotriazineorganothiophosphateinsecticide)例如益棉磷(azinphos-ethyl)和保棉磷(azinphos-methyl)；吡啶有机硫代磷酸酯杀虫剂(pyridineorganothiophosphateinsecticide)例如毒死蜱(chlorpyrifos)和甲基毒死蜱(chlorpyrifos-methyl)；嘧啶有机硫代磷酸酯杀虫剂(pyrimidineorganothiophosphateinsecticide)例如二嗪农(diazinon)；苯基有机硫代磷酸酯杀虫剂(phenylorganothiophosphateinsecticide)例如对硫磷(parathion)和甲基对硫磷(parathion-methyl)；合成除虫菊酯杀虫剂(pyrethroidesterinsecticide)例如联苯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、β-氯氰菊酯(beta-cypermethrin)、氰戊菊酯(fenvalerate)和苄氯菊脂(permethrin)；等等。
可用在本发明水包油乳液中的示例性除草剂包括但不限于:酰胺类除草剂(amideherbicide)例如二甲吩草胺(dimethenamid)和精二甲吩草胺(dimethenamid-P)；酰替苯胺类除草剂(anilideherbicide)例如敌稗(propanil)；氯代乙酰苯胺类除草剂(chloroacetanilideherbicide)例如刈草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、异丙甲草胺(metolachlor)和S-异丙甲草胺(S-metolachlor)；环己烯肟类除草剂(cyclohexeneoximeherbicide)例如稀禾定(sethoxydim)；二硝基苯胺类除草剂(dinitroanilineherbicide)例如氟草胺(benfluralin)、丁氟消草(ethalfluralin)、胺硝草(pendimethalin)和氟乐灵(trifluralin)；腈类除草剂(nitrileherbicide)例如溴苯腈辛酸酯(bromoxyniloctanoate)；苯氧基乙酸类除草剂(phenoxyaceticherbicide)例如促生灵(4-CPA)、2,4-滴(2,4-D)、3,4-滴胺(3,4-DA)、2甲4氯(MCPA)和酚硫杀(MCPA-thioethyl)；苯氧基丁酸类除草剂(phenoxybutyricherbicide)例如氯苯氧丁酸(4-CPB)、2,4-滴丁酸(2,4-DB)、3,4-滴丁酸(3,4-DB)和2甲4氯丁酸(MCPB)；苯氧基丙酸类除草剂(phenoxypropionicherbicide)例如调果酸(cloprop)、氯苯氧丙酸(4-CPP)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、3,4-滴丙酸(3,4-DP)、2,4,5-涕丙酸(fenoprop)、2甲4氯丙酸(mecoprop)和精2甲4氯丙酸(mecoprop-P)；芳氧基苯氧基丙酸类除草剂(aryloxyphenoxypropionicherbicide)例如氰氟草酯(cyhalofop)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-R)；吡啶基类除草剂(pyridineherbicide)例如氯氨基吡啶酸(animopyralid)、二氯吡啶酸(clopyralid)、氟草烟(fluroxypyr)、毒莠定(picloram)和绿草定(triclopyr)；三唑类除草剂(triazoleherbicide)例如氟酮唑草-乙基(carfentrazoneethyl)；等等。
所述除草剂也通常可与已知的除草剂安全剂(herbicidesafener)结合使用，所述除草剂安全剂为例如:解草嗪(benoxacor)、解草酯(cloquintocet)、解草胺腈(cyometrinil)、香草隆(daimuron)、烯丙酰草胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草唑-乙基(fenchlorazole-ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草唑(furilazole)、isoxadifen、双苯唑酸乙酯(isoxadifen-ethyl)、mefenpyr、吡唑解草酯(mefenpyr-diethyl)、MG191、MON4660、R29148、mephenate、萘酸酐(naphthalicanhydride)、N-苯基磺酰基苯甲酸酰胺(N-phenylsulfonylbenzoicacidamides)和解草腈(oxabetrinil)。
可用在本发明水包油乳液中的示例性杀真菌剂包括但不限于苯醚甲环唑(difenoconazole)、烯酰吗啉(dimethomorph)、二硝巴豆酸酯(dinocap)、二苯胺(diphenylamine)、十二环吗啉(dodemorph)、敌瘟磷(edifenphos)、氯苯嘧啶醇(fenarimol)、腈苯唑(fenbuconazole)、丁苯吗啉(fenpropimorph)、腈菌唑(myclobutanil)、油酸(脂肪酸)(oleicacid(fattyacid))、丙环唑(propiconazole)、戊唑醇(tebuconazole)等。
本领域技术技术人员理解的是，只要仍能得到稳定和有效的乳液，则也可在本发明水包油乳液中使用农业活性化合物的任意组合。
水包油乳液内的农业活性成分的量会随实际的活性成分、农业活性成分的应用和本领域技术人员公知的合适应用水平而变化。通常，以水包油乳液的总重量计，所述农业活性成分在水包油乳液中的总量为从约1wt％，通常从约5wt％，优选从约10wt％，更优选从约15wt％和最优选从约20wt％至约45wt％，通常至约40wt％，优选至约35wt％和最优选至约30wt％。
聚合物改性剂可包括在油相中以阻止农业活性成分的结晶。所述聚合物改性剂容许使用熔点低于约95℃的农业活性成分。可用在本发明水包油乳液组合物中的所述农业活性成分的实例包括氟草烟甲基庚基酯(FluroxpyrMeptyl)、毒死蜱、甲基毒死蜱、氟乐灵、氰氟草丁酯(Cyhalofopbutyl)、丁氟消草、氟草胺、腈菌唑、灭螨醌(Acequinocyl)、α-氯氰菊酯、虫螨脒、杀虫磺、β-氟氯氰菊酯、β-氯氰菊酯、治草醚、联苯菊酯、生物苄呋菊酯、溴苯腈辛酸酯、地乐胺、环氟苄酰胺、氟氯氰菊酯、氯氰菊酯、氯甲草(Diclofop-methyl)、三氯杀螨醇(Dicofol)、高氰戊菊酯、丁氟消草、醚菊酯、喹螨醚(Fenazaquin)、高唑禾草灵-乙基(Fenoxaprop-P-ethyl)、甲氰菊酯、氰戊菊酯、氟烯草酸-戊基酯(Flumiclorac-pentyl)、乙羧氟草醚-乙基(Fluoroglycofen-ethyl)、解草胺、氟吡禾灵-etotyl、茚虫威、λ-三氟氯氰菊酯、唑酰草胺、甲氧氯(Methoxychlor)、乙氧氟草醚、胺硝草、苄氯菊脂、喔草酯、稗草畏、精喹禾灵-乙基(Quizalofop-P-ethyl)、肟菌酯、溴硫磷、高唑禾草灵-乙基(Fenoxaprop-ethyl)、异丙吡草酯、除草醚和环丙氟灵。
用于加到油相中的合适的聚合物改性剂具有非常低的水溶性和于熔融状态的活性成分混合物(具有或不具有额外的溶剂)中的良好的溶解性。合适的聚合物改性剂的实例可包括乙基纤维素例如Ethocel10StdFP、EthocelStd4、EthocelStd7、Ethocel45、Ethocel100FP和Ethocel300；聚丙烯酸酯、胶乳(Latex)、聚碳酸酯、聚乙酸乙烯酯均聚物和共聚物、聚烯烃、聚氨酯、聚异丁烯、聚丁烯、乙烯基聚合物、聚酯、聚醚和聚丙烯腈。
使用下述方法结合水包油乳液的组分以产生具有层状液体晶体涂层(lamellarliquidcrystalcoating)的油滴。所述层状液体晶体涂层是非常精细的单-或寡层状(oligolamellar)层。寡层状层被理解为是指包含2至5层脂质薄层的层。该层状液体晶体涂层可通过如下方法检测：在低温断裂(cryofracture)或阴性染色后通过透射电子显微镜检测、通过X射线衍射检测或在偏振光条件下通过光学显微镜检测。层状晶体液体相的术语和结构在"TheColloidalDomain"(第二版),D.FennellEvans和H.Wennerstrom,Wiley-VCH(1999)，第295-296页和306-307页中被很好地定义。所述寡层状层由前述的非离子亲脂性表面活性剂、非离子亲水性表面活性剂和离子表面活性剂组成。优选地，所述亲脂性表面活性剂和所述亲水性表面活性剂各自含有至少一种任选饱和的和/或支链的具有多于12个碳原子，优选具有16至22个碳原子的脂肪族烃链。
优选地，所述亲脂性表面活性剂具有约2至约5的HLB。HLB是本领域技术人员已知的标准术语，其是指亲水亲油平衡值，所述亲水亲油平衡值鉴别乳化剂于水或油中的溶解度。
亲脂性描述了物质溶解在脂肪样溶剂或脂质中的能力。所述亲脂性表面活性剂通常选自甘油或聚甘油的任选乙氧基化的单-或多烷基醚或酯、脱水山梨糖醇(任选乙氧基化)的单-或多烷基醚或酯、季戊四醇的单-或多烷基醚或酯、聚氧乙烯的单-或多烷基醚或酯和糖的单-或多烷基醚或酯。亲脂性表面活性剂的实例包括但不限于蔗糖二硬脂酸酯(sucrosedistearate)、二硬脂酸二甘油酯(diglyceryldistearate)、三硬脂酸四甘油酯(tetraglyceryltristearate)、十硬脂酸十甘油酯(decaglyceryldecastearate)、单硬脂酸二甘油酯(diglycerylmonostearate)、三硬脂酸六甘油酯(hexaglyceryltristearate)、五硬脂酸十甘油酯(decaglycerylpentastearate)、脱水山梨糖醇单硬脂酸酯(sorbitanmonostearate)、脱水山梨糖醇三硬脂酸酯(sorbitantristearate)、单硬脂酸二甘醇酯(diethyleneglycolmonostearate)、甘油与棕榈酸和硬脂酸的酯(theesterofglycerolandpalmiticandstearicacids)、聚氧乙烯化的单硬脂酸酯2EO(含有2个环氧乙烷单元)、山嵛酸甘油单酯和山嵛酸甘油二酯(glycerylmono-anddibehenate)和季戊四醇四硬脂酸酯(pentaerythritoltetrastearate)。
亲水性描述了物质与水缔合的亲和性。所述亲水性表面活性剂通常具有约8至约12的HLB，并且通常选自聚乙氧基化脱水山梨糖醇的单-或多烷基醚或酯、聚氧乙烯的单-或多烷基醚或酯、聚甘油的单-或多烷基醚或酯、聚氧乙烯与聚氧丙烯或聚氧丁烯的嵌段共聚物和任选乙氧基化的糖的单-或多烷基醚或酯。亲水性表面活性剂的实例包括但不限于聚氧乙烯化的脱水山梨糖醇单硬脂酸酯4EO、聚氧乙烯化的脱水山梨糖醇三硬脂酸酯20EO、聚氧乙烯化的脱水山梨糖醇三硬脂酸酯20EO、聚氧乙烯化单硬脂酸酯8EO、单硬脂酸六甘油酯、聚氧乙烯化的单硬脂酸酯10EO、聚氧乙烯化的二硬脂酸酯12EO和聚氧乙烯化的甲基葡萄糖二硬脂酸酯20EO。
除了所述亲脂性表面活性剂和亲水性表面活性剂，离子表面活性剂也包含在层状液体晶体涂层的寡层状层中。
可用在本发明水包油乳液中的离子表面活性剂包括(a)中和的阴离子表面活性剂(neutralizedanionicsurface-activeagents)，(b)两性表面活性剂(amphotericsurface-activeagents)，(c)烷基磺酸衍生物，和(d)阳离子表面活性剂(cationicsurface-activeagents)。
中和的阴离子表面活性剂(a)包括但不限于例如:
-磷酸二鲸蜡基酯的碱金属盐和磷酸二肉豆蔻基酯的碱金属盐，特别是钠盐和钾盐；
-胆甾醇硫酸酯和胆甾醇磷酸酯的碱金属盐，特别是钠盐；
-脂氨基酸和它们的盐例如酰基谷氨酸一钠和酰基谷氨酸二钠例如N-硬脂酰基-L-谷氨酸的二钠盐和磷脂酸的钠盐；
-磷脂；和
-酰基谷氨酸特别是N-硬脂酰基谷氨酸的一钠盐和二钠盐。
可用在本发明水包油乳液中的选自烷基醚柠檬酸酯及其混合物的阴离子表面活性剂披露在美国专利6,413,527中，将该专利引入本申请作为参考。烷基醚柠檬酸酯包括由柠檬酸与至少一种氧乙烯化脂肪醇形成的单酯或二酯及它们的混合物，所述氧乙烯化脂肪醇包括具有8至22个碳原子和包括3至9个氧乙烯基的饱和或不饱和、直链或支链烷基链。这些柠檬酸酯可选自例如柠檬酸与包括3至9个氧乙烯基的乙氧基化月桂醇形成的单-和二酯。所述烷基醚柠檬酸酯优选以中和形式(即pH约7)使用。中和剂可选自无机碱和有机碱，所述无机碱为例如氢氧化钠、氢氧化钾或氨，所述有机碱为例如单-、二-和三乙醇胺、氨甲基-1,3-丙二醇、N-甲基葡糖胺、碱性氨基酸例如精氨酸和赖氨酸及它们的混合物。
两性表面活性剂(b)包括但不限于磷脂，特别是来自纯大豆(puresoya)的磷脂酰乙醇胺。
烷基磺酸衍生物(c)包括但不限于下式化合物:
其中R表示基团C16H33和C18H37，采取混合的形式或单独的形式，以及M为碱金属优选为钠。
阳离子表面活性剂(d)包括但不限于美国专利6,464,990披露的表面活性剂，将该专利引入本申请作为参考。它们通常选自季铵盐、脂肪胺及其盐。季铵盐包括例如具有下式的那些季铵盐：
其中所述R1至R4基团可相同或不同，表示含有1至30个碳原子的直链或直链脂肪族基团，或芳族基团例如芳基或烷基芳基。所述脂肪族基团可包含杂原子例如氧、氮、硫和卤素。所述脂肪族基团包括烷基、烷氧基、聚氧化(C2-C6)烯、烷基酰氨基、(C12-C22)烷基-酰氨基(C2-C6)烷基、(C12-C22)烷基乙酸酯基和包含约1至30个碳原子的羟烷基基团；X为选自如下的阴离子：卤素离子、磷酸根离子、乙酸根离子、乳酸根离子、(C2-C6)烷基硫酸根离子和烷基磺酸根离子或烷基芳基磺酸根离子。优选的季铵盐为四烷基氯化铵例如二烷基二甲基氯化铵和烷基三甲基氯化铵，其中烷基包含约12至22个碳原子，特别是山嵛基三甲基氯化铵、二硬脂基二甲基氯化铵、十六烷基三甲基氯化铵和苄基二甲基硬脂基氯化铵，或者可选择地，硬脂酰氨基丙基二甲基(肉豆蔻基氧基羰基甲基)氯化铵(stearamidopropyl-dimethyl(myristylacetate)ammoniumchloride)；咪唑鎓季铵盐，例如下式的那些：
其中R5表示含有8至30个碳原子的烯基或烷基，例如源自牛油脂肪酸的那些；R6表示氢原子、含有1至4个碳原子的烷基或含有8至30个碳原子的烯基或烷基；R7表示含有1至4个碳原子的烷基；R8表示氢原子或含有1至4个碳原子的烷基；以及，X为选自如下的阴离子：卤素离子、磷酸根离子、乙酸根离子、乳酸根离子、烷基硫酸根离子或烷基磺酸根离子和烷基芳基磺酸根离子。R5和R6优选表示含有12至21个碳原子的烯基或烷基的组合，例如源自牛油脂肪酸的那些，R7优选表示甲基，以及R8优选表示氢。也考虑使用季二铵盐(Quaternarydiammoniumsalts)例如丙烷牛脂基二氯化二铵。
脂肪胺包括但不限于下式的那些:
R9(CONH)n(CH2)mN(R11)R10
其中R9为任选饱和和/或支链烃链，具有8至30个碳原子，优选10至24个碳原子；R10和R11选自H和任选饱和和/或支链烃链，具有1至10个碳原子，优选1至4个碳原子；m为1至10的整数，优选为1至5的整数；n为0或1。
脂肪胺的实例包括但不限于硬脂胺、氨基乙基-硬脂酸乙醇酰胺(aminoethyl-ethanolamidestearate)、二亚乙基三胺硬脂酸盐(diethylenetriaminestearate)、棕榈酰氨基二甲基胺、棕榈酰氨基丙基二乙基胺、棕榈酰氨基乙基二乙基胺、棕榈酰氨基乙基二甲基胺。商购的脂肪胺包括但不限于购自Croda的IncromineTMBB、购自Nikkol的AmidoamineTMMSP和购自Inolex的LexamineTM系列，购自KaoCorp的Acetamine系列；Berol380、390、453和455，和购自AkzoNobel的EthomeenTM系列和购自CondeaChemie的MarlazinTML10、OL2、OL20、T15/2、T50。
如上所述，所述表面活性剂形成悬浮在本发明水包油乳液的水相中的油滴的层状液体晶体涂层。以表面活性剂的总组合重量计，用在本发明水包油乳液中的三种表面活性剂的量通常为：从约20wt％，优选从约35wt％至约65wt％，优选至约55wt％非离子亲脂性表面活性剂；从约15wt％，优选从约25wt％至约50wt％，优选至约40wt％非离子亲水性表面活性剂；和从约5wt％,优选从约10wt％至约45wt％，优选至约35wt％离子表面活性剂。以水包油乳液的总重量计，油滴涂层包含的亲水性表面活性剂、亲脂性表面活性剂和离子表面活性剂的总量为约2wt％至约20wt％。优选地，以水包油乳液的总重量计，总量为约2.5wt％，更优选为从约3wt％至约10wt％，更优选至约6wt％。
表面活性化合物的总重量与油的总重量的比例通常为1:2.5至1:25。
以水包油乳液的总重量计，用在本发明水包油乳液中的聚合物改性剂的量通常从约0.2wt％，优选从约2wt％至约40wt％，优选至约20wt％。
水相通常为水，例如去离子水。水相也可含有其它添加剂例如降低凝固点(freezingpoint)的化合物例如醇类，例如异丙醇和丙二醇；pH缓冲剂，例如碱金属磷酸盐例如磷酸二氢钠一水合物、磷酸氢二钠；杀生物剂例如ProxelGXL；和消泡剂例如八甲环四硅氧烷(来自DowCorning的消泡剂A)。水相中也可存在其它添加剂和/或助剂，只要仍保持水包油乳液的稳定性。其它添加剂也包括水溶性农业活性化合物。
以水包油乳液组合物的总重量计，油相或被涂覆的油滴为从5wt％，优选从8wt％和更优选从10wt％至50wt％，优选至45wt％，以及最优选至40wt％。油/水比通常小于或等于1。
在本发明水包油乳液中也可存在其它添加剂和/或助剂，只要仍获得水包油乳液的稳定性和活性。本发明的水包油乳液可额外含有辅助表面活性剂以提高农业活性成分沉积、润湿和渗透到目标位点上，所述目标位点为例如作物、杂草或生物。这些辅助表面活性剂可任选用作于油相或水相中的所述乳液的组分，或作为桶混组分(tankmixcomponent)；所需用量是本领域技术人员熟知的。合适的辅助表面活性剂包括但不限于壬基酚、乙氧基化合成醇或天然醇、磺基琥珀酸的盐或磺基琥珀酸酯的盐、乙氧基化有机硅氧烷、乙氧基化脂肪胺和表面活性剂与矿物油或植物油的共混物。
本发明的水包油乳液可根据美国专利5,925,364中描述的方法制备，将所述专利教导的内容引入本申请作为参考。首先将农业活性成分或农业活性成分的组合熔化或溶解在聚合物改性剂中(如果需要加入溶剂)，然后将非离子表面活性剂溶解在混合物中。接着使用高压均化器通过空化作用使混合物均化，得到小粒径的油滴。被涂覆的油滴的平均粒径通常小于800纳米，优选小于500纳米，以及最优选为约200纳米，如使用激光衍射粒径分析和扫描电子显微镜所确定的。
在一个实施方案中，通过如下方式制备所述水包油乳液:
1)将一种或多种农业活性成分熔化或溶解在聚合物改性剂和任选的合适溶剂中；
2)混合物油相和水相(B)得到混合物，所述油相包含亲脂性表面活性剂、含有被溶解的农业活性成分的聚合物改性剂、亲水性表面活性剂、离子表面活性剂农业活性化合物和任选的溶剂；和
3)通过使所述混合物经受空化作用而对其进行均化。
在第一步中，可通过常规搅拌例如使用高剪切均化器形成混合物，所述均化器以约2000至7000rpm的速度旋转约5至60分钟并且温度为约20℃至95℃。
可通过使用在约200至1000巴操作的高压均化器进行均化，这一点是本领域技术人员公知的。所述方法在所选择的压力通过连续道次(通常为2至12个道次)进行；在每个道次(passage)之间使混合物恢复到常压。第二步的均化也可在超声的作用下进行，或可选择地，可通过装备有转子-定子型头的均化器进行。
本发明另一实施方案为水包油乳液在农业应用中控制、预防或消灭不希望的活生物体的用途，所述活生物体为例如真菌、杂草、昆虫、细菌或其它微生物和其它害虫。这包括所述水包油乳液用于保护植物免受致植物病生物(phytopathogenicorganism)侵袭的用途或治疗已经受致植物病生物侵害的植物的用途，所述用途包括将所述水包油乳液组合物以病害抑制和植物学可接受的量施用至土壤、植物、植物部分、叶子、花朵、果实和/或种子。术语"病害抑制和植物学可接受的量"是指化合物杀死或抑制需要对其进行控制的植物病害的量，但对植物不是显著毒性的。所需要的活性化合物的确切浓度随要控制的真菌病害、所使用的制剂类型、应用方法、具体的植物种类、气候条件等变化，这一点是本领域已知的。
此外，本发明的水包油乳液用于控制昆虫或其它害虫，例如啮齿类动物。因此，本发明还涉及抑制昆虫或害虫的方法，包括向昆虫或害虫位点(locus)施用水包油乳液，所述水包油乳液含有用于所述用途的昆虫抑制量的农业活性化合物。所述昆虫或害虫的"位点"是本文使用的术语，其是指昆虫或害虫生活的环境或它们的卵存在的地方，包括围绕它们的空气、它们吃的食物或它们接触的物体。例如，可通过如下方式控制食用或接触可食用植物或观赏植物的昆虫：将活性化合物施用至植物部分例如种子、苗或所种植的插条、叶子、茎、果实、谷粒或根，或将活性化合物施用至所述根在其中生长的土壤。预期的是，农业活性化合物和含有所述化合物的水包油乳液也可通过将活性化合物施用至织物、纸、贮藏的谷物、种子、家畜、建筑物或人类或所述物体的附近而用于保护所述物体。术语"抑制昆虫或害虫"是指减少活昆虫或害虫的数目，或减少可繁殖的昆虫卵的数目。当然，化合物能实现的减少程度依赖于化合物的施用率、所使用的具体化合物和目标昆虫或害虫种类。应当使用至少一个失活量(inacticvatingamount)。术语"昆虫或害虫失活量"用于描述如下量，所述量足以造成被处理昆虫或害虫种群的可测量的降低，这是本领域所公知的。
化合物或组合物所施用的位点可以是昆虫、螨虫或害虫栖息的任意位点，例如蔬菜作物、水果树和坚果树、葡萄藤、观赏植物、家畜、建筑物的内外表面和建筑物周围的土壤。
由于昆虫卵抗毒性作用的独特能力，因此可能需要反复施用以控制新出现的幼虫，其它已知杀昆虫剂和杀壁虱剂(acaricide)就是这种情况。
此外，本发明涉及含有农业活性化合物的水包油乳液的用途，所述农业活性化合物为除草剂。本文使用的术语“除草剂”是指杀死、控制或不利地改变植物生长的活性成分。除草有效量或植被控制量是下述活性成分的量，所述活性成分的量造成不利的改变作用，并包括偏离自然发育、杀死、调节、脱水(desiccation)、阻滞等。术语“植物(plant)”和“植被(vegetation)”包括正在出土的幼苗和已经长成的植被。
当在杂草生长的任意阶段或在杂草出土前将农业活性成分或组合物直接施用至不希望植物的位点而表现出除草活性。观察到的作用依赖于所控制的植物种类、植物的生长阶段、固体组分的粒径、使用时的环境条件、所采用的具体助剂和载体、土壤类型等，以及所施用的化学品的量。
如本领域所知，可对这些和其它因素进行调整以提高选择性除草作用。通常，优选的是将所述除草剂苗后施用至相对不成熟的不期望的植被以实现对杂草的最大控制。
本发明另一个具体方面是预防或控制害虫例如线虫、螨虫、节肢动物、啮齿动物、白蚁(termite)、细菌或其它微生物的方法，包括向需要控制或预防的位点施用本发明组合物，所述组合物包含合适的活性化合物例如杀线虫剂、杀螨剂、杀节肢动物剂、杀啮齿动物剂、驱蚁剂或杀生物剂。
施用至病害、昆虫和螨虫、杂草或其它害虫的位点的农业活性化合物的确切量是本领域公知的并可容易地由本领域技术人员根据上述教导进行确定。
本发明组合物出人意料地提供稳定的、具有低粘度和长储存期限的农业水包油乳液。此外，本发明稳定的农业水包油乳液可提供其它出人意料的改进，例如效力。提供如下实施例来说明本发明。
所述实施例不是意欲限制本发明的范围并且不应对它们进行这样的解释。除非另有说明，量的单位为重量份或重量百分比。
具体实施方式
实施例
提供这些实施例来进一步说明本发明，并且不意指被理解为进行限制。
如本文所披露，除非另有说明，所有温度以摄氏度为单位给出并且所有百分比为重量百分比。所有实施例中的活性成分为过饱和的。
在这些实施例中，使用如下操作进行所述方法:
将固体农业活性成分熔化或溶解在聚合物改性剂中。然后将所述聚合物改性剂混合在油相A中。将油相A和水相B分别加热至所需温度。伴随着4000-8000rpm的搅拌，将相B倒入相A中，所述搅拌由安装有方孔高剪切筛的SilversonL4RT高剪切均化器提供。搅拌和温度条件保持10分钟。
然后将混合物引入到Panda2K类型的NiroSoavi高压2-阶段均化器中，将所述均化器调整至1000巴压力，持续2至12个连续道次。
由此得到经稳定的水包油乳液，所述水包油乳液的油滴具有通常约200nm的平均粒径。
实施例1:氟草烟甲基庚基酯(Fluroxypyrmethylheptylester)水包油乳液
油相
水相B
所述样品在0℃和室温10周后没有显示晶体形成、分出乳油(creaming)或沉降的迹象。由MalvernZetasizer所确定的水包油乳液的油滴的大小为242nm。在冷冻/解冻(温度每天从-10℃至40℃循环)和在54℃，所述水包油乳液在10周的加速储存试验条件下为稳定的，油滴的大小没有变化，并且没有沉降或脱水收缩。
实施例2:氟草烟甲基庚基酯水包油乳液
水相B
由MalvernZetasizer所确定的水包油乳液的油滴的大小为410nm。所述样品在0℃和室温10周后没有显示晶体形成、分出乳油或沉降的迹象。在冷冻/解冻(温度每天从-10℃至40℃循环)和在54℃，所述水包油乳液在10周的加速储存试验条件下为稳定的，油滴的大小没有变化，并且没有沉降或脱水收缩。
实施例3:氟草烟甲基庚基酯水包油乳液
水相B
所述样品在室温2周后没有显示晶体形成、分出乳油或沉降的迹象。由MalvernZetasizer所确定的水包油乳液的油滴的大小为190nm。在室温、40℃和54℃，所述水包油乳液在2周的加速储存试验条件下为稳定的，油滴的大小没有变化，并且没有沉降或脱水收缩。
实施例4:氟乐灵水包油乳液
水相B
所述样品在室温2周后没有显示晶体形成、分出乳油或沉降的迹象。由MalvernZetasizer所确定的水包油乳液的油滴的大小为185nm。在40℃和54℃，所述水包油乳液在2周的加速储存试验条件下为稳定的，油滴的大小没有变化，并且没有沉降或脱水收缩。
实施例5:毒死蜱水包油乳液
水相B
去离子水82.6
N-硬脂酰基谷氨酸二钠盐0.5
(由AjinomotoAmisoft提供的HS-21P)
所述样品在室温2周后没有显示晶体形成、分出乳油或沉降的迹象。由MalvernZetasizer所确定的水包油乳液的油滴的大小为190nm。在40℃和54℃，所述水包油乳液在2周的加速储存试验条件下为稳定的，油滴的大小没有变化，并且没有沉降或脱水收缩。
实施例6:毒死蜱水包油乳液
水相B
所述样品在室温2周后没有显示晶体形成、分出乳油或沉降的迹象。由MalvernZetasizer所确定的水包油乳液的油滴的大小为190nm。在40℃，2周的加速储存试验条件导致油滴的大小轻微增加至200nm。
Claims (24)
1.一种水包油乳液组合物，其具有油相和水相，所述油相包含:
与所述油相相容的聚合物改性剂；
至少一种农业活性化合物；
至少一种非离子亲脂性表面活性剂；
至少一种非离子亲水性表面活性剂；
至少一种离子表面活性剂。
2.权利要求1的组合物，其中所述非离子亲脂性表面活性剂具有2至5的亲水亲油平衡值。
3.权利要求2的组合物，其中所述非离子亲脂性表面活性剂选自甘油或聚甘油的任选乙氧基化的单-或多烷基醚或酯、脱水山梨糖醇任选乙氧基化的单-或多烷基醚或酯、季戊四醇的单-或多烷基醚或酯、聚氧乙烯的单-或多烷基醚或酯和糖的单-或多烷基醚或酯。
4.权利要求3的组合物，其中所述非离子亲脂性表面活性剂选自蔗糖二硬脂酸酯、二硬脂酸二甘油酯、三硬脂酸四甘油酯、十硬脂酸十甘油酯、单硬脂酸二甘油酯、三硬脂酸六甘油酯、五硬脂酸十甘油酯、脱水山梨糖醇单硬脂酸酯、脱水山梨糖醇三硬脂酸酯、单硬脂酸二甘醇酯、甘油与棕榈酸和硬脂酸的酯、聚氧乙烯化的单硬脂酸酯2EO(含有2个环氧乙烷单元)、山嵛酸甘油单酯和山嵛酸甘油二酯和季戊四醇四硬脂酸酯。
5.权利要求1的组合物，其中所述非离子亲水性表面活性剂具有8至12的亲水亲油平衡值。
6.权利要求5的组合物，其中所述非离子亲水性表面活性剂选自聚乙氧基化脱水山梨糖醇的单-或多烷基醚或酯、聚氧乙烯的单-或多烷基醚或酯、聚甘油的单-或多烷基醚或酯、聚氧乙烯与聚氧丙烯或聚氧丁烯的嵌段共聚物和任选乙氧基化的糖的单-或多烷基醚或酯。
7.权利要求6的组合物，其中所述非离子亲水性表面活性剂选自聚氧乙烯化的脱水山梨糖醇单硬脂酸酯4EO、聚氧乙烯化的脱水山梨糖醇三硬脂酸酯20EO、聚氧乙烯化的脱水山梨糖醇三硬脂酸酯20EO、聚氧乙烯化单硬脂酸酯8EO、单硬脂酸六甘油酯、聚氧乙烯化的单硬脂酸酯10EO、聚氧乙烯化的二硬脂酸酯12EO和聚氧乙烯化的甲基葡萄糖二硬脂酸酯20EO。
8.权利要求1的组合物，其中所述离子表面活性剂选自(a)中和的阴离子表面活性剂，(b)两性表面活性剂，(c)烷基磺酸衍生物，和(d)阳离子表面活性剂。
9.权利要求8的组合物，其中所述离子表面活性剂选自:
-磷酸二鲸蜡基酯的碱金属盐和磷酸二肉豆蔻基酯的碱金属盐，特别是钠盐和钾盐；
-胆甾醇硫酸酯和胆甾醇磷酸酯的碱金属盐，特别是钠盐；
-脂氨基酸和它们的盐例如酰基谷氨酸一钠和酰基谷氨酸二钠例如N-硬脂酰基-L-谷氨酸的二钠盐和磷脂酸的钠盐；
-磷脂；
-酰基谷氨酸特别是N-硬脂酰基谷氨酸的一钠盐和二钠盐；和
-烷基醚柠檬酸酯。
10.权利要求8的组合物，其中所述离子表面活性剂为磷脂.
11.权利要求8的组合物，其中所述离子表面活性剂为烷基磺酸衍生物。
12.权利要求8的组合物，其中所述离子表面活性剂选自季铵盐、脂肪胺及其盐。
13.权利要求1的组合物，其中农业活性化合物选自杀真菌剂、杀昆虫剂、杀线虫剂、杀螨剂、杀生物剂、驱蚁剂、杀啮齿动物剂、杀节肢动物剂和除草剂。
14.一种用于控制或预防真菌侵袭的方法，包括将权利要求13的组合物施用至真菌、土壤、植物、根、叶子、种子或即将对侵袭进行预防或控制的位点。
15.一种抑制昆虫的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
16.一种预防或控制不期望的植被的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
17.一种预防或预防线虫的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
18.一种预防或控制螨虫的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
19.一种预防或控制节肢动物的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
20.一种预防或控制细菌和其它微生物的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
21.一种预防或控制啮齿动物的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
22.一种预防或控制白蚁的方法，包括向需要控制或预防的位点施用权利要求13的组合物。
23.权利要求1的组合物，其中所述聚合物改性剂选自乙基纤维素、Ethocel10StdFP、EthocelStd4、EthocelStd7、Ethocel45、Ethocel100FP、Ethocel300；聚丙烯酸酯、胶乳、聚碳酸酯、聚乙酸乙烯酯均聚物和共聚物、聚烯烃、聚氨酯、聚异丁烯、聚丁烯、乙烯基聚合物、聚酯、聚醚和聚丙烯腈。
24.权利要求1的组合物，其中以水包油乳液组合物的总重量计，所述水包油乳液组合物包括约1至约60wt％的总油相，约0.2至约40wt％的聚合物改性剂，约1至约45wt％的农业活性化合物，约0.4至约13wt％的非离子亲脂性表面活性剂，约0.3至约10wt％的非离子亲水性表面活性剂，以及约0.1至约9wt％离子表面活性剂。
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| CN2009801116074A CN101980599A (zh) | 2008-02-04 | 2009-02-04 | 包含农业活性成分的经稳定的水包油乳液 |
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| WO2009145959A1 (en) * | 2008-03-07 | 2009-12-03 | University Of Toledo | High throughput carbon nanotube growth system, and carbon nanotubes and carbon nanofibers formed thereby |
| EP2278876B1 (en) * | 2008-03-25 | 2015-12-23 | Dow AgroSciences LLC | Stabilized oil-in-water emulsions including agriculturally active ingredients |
| UA111167C2 (uk) * | 2010-08-05 | 2016-04-11 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Пестицидні композиції мезорозмірних частинок з підсиленою дією |
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| BR102014027711A2 (pt) * | 2013-11-08 | 2015-09-15 | Dow Agrosciences Llc | concentrados de emulsão pesticida contendo óleos naturais ou derivados do petróleo e métodos de uso |
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| CN104054709A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与氟啶胺的杀菌组合物 |
| CN104054708A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与螺环菌胺的杀菌组合物 |
| CN104054711A (zh) * | 2014-06-30 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与氟菌唑的杀菌组合物 |
| CN107660122A (zh) * | 2015-05-12 | 2018-02-02 | 禾大公司 | 农业化学乳液 |
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| HK1221868A1 (zh) | 2017-06-16 |
| JP5995945B2 (ja) | 2016-09-21 |
| US20090197768A1 (en) | 2009-08-06 |
| PL2252145T3 (pl) | 2016-10-31 |
| JP2011511010A (ja) | 2011-04-07 |
| DK2252145T3 (en) | 2016-07-18 |
| WO2009100144A1 (en) | 2009-08-13 |
| JP5972530B2 (ja) | 2016-08-17 |
| WO2009100145A1 (en) | 2009-08-13 |
| BRPI0907480B1 (pt) | 2019-09-03 |
| EP2240014A1 (en) | 2010-10-20 |
| BRPI0907480A2 (pt) | 2019-01-15 |
| EP2252145B1 (en) | 2016-04-06 |
| CO6280437A2 (es) | 2011-05-20 |
| RU2504956C2 (ru) | 2014-01-27 |
| US20090203528A1 (en) | 2009-08-13 |
| KR20100114513A (ko) | 2010-10-25 |
| MX338895B (es) | 2016-05-04 |
| ES2567297T3 (es) | 2016-04-21 |
| JP5701065B2 (ja) | 2015-04-15 |
| EP2252145A1 (en) | 2010-11-24 |
| US9426982B2 (en) | 2016-08-30 |
| KR101846543B1 (ko) | 2018-04-06 |
| US8999893B2 (en) | 2015-04-07 |
| MX2010008610A (es) | 2010-09-07 |
| JP2011511009A (ja) | 2011-04-07 |
| CA2713717C (en) | 2016-07-26 |
| AU2009212477A1 (en) | 2009-08-13 |
| RU2010136928A (ru) | 2012-03-20 |
| JP2015078219A (ja) | 2015-04-23 |
| AU2009212477B2 (en) | 2014-11-13 |
| CA2713717A1 (en) | 2009-08-13 |
| CN101980599A (zh) | 2011-02-23 |
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