CN102781231A - 用于农业中的peham树枝状化合物 - Google Patents
用于农业中的peham树枝状化合物 Download PDFInfo
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- CN102781231A CN102781231A CN2010800562901A CN201080056290A CN102781231A CN 102781231 A CN102781231 A CN 102781231A CN 2010800562901 A CN2010800562901 A CN 2010800562901A CN 201080056290 A CN201080056290 A CN 201080056290A CN 102781231 A CN102781231 A CN 102781231A
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- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 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
- 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
- A01N25/22—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 ingredients stabilising the active ingredients
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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
- A01N25/24—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 ingredients to enhance the sticking of the active ingredients
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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
- A01N25/30—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/005—Dendritic macromolecules
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- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Abstract
用于含活性剂的配制剂中的特定的PEHAM树枝状化合物,其用于农业意图,特别用于以各种方式增加活性剂的效力,比如通过改善活性剂在配制剂中的溶解度,通过改善活性剂对植物表面的粘着和穿透,通过改善活性剂对植物或种子的耐水牢度,通过提供对活性剂的保护避免UV损害,通过增加活性剂的土壤穿透以到达植物根部或土壤下部分,或者通过降低活性剂的土壤粘着以到达植物根部或土壤下部分,或者降低植物或种子或土壤中的微生物对活性剂的酶促降解。
Description
相关申请
本发明涉及共同未决的2005年4月20日提交的US Serial No.10/594,776和2005年12月21日提交的US 11/630,044。上述这些专利申请通过援引全部并入本文。
发明背景
发明领域
本发明宽泛地涉及PEHAM树枝状化合物在农业应用中的用途,但是更特别用于使用特定的PEHAM树枝状化合物保护和处理植物和种子。
背景技术
树枝状化合物是高度支化的、常为球形的分子,其中分支可以终止于自中央核心分子辐射的带电氨基。胺终止的树枝状化合物在表面具有高密度带正电的胺基团,比如PAMAM树枝状化合物。由于受控化学合成,树枝状化合物具有很精确的尺寸和经限定的形状。
PEHAM树枝状化合物与PAMAM树枝状化合物有关,但是区别于下述特征中的至少一个或多个:PEHAM树枝状化合物显示增加的热稳定性,更快速的表面官能团形成,在较低代具有增加的分子量,由此降低制备成分,窄多分散性,增加的内部空间体积,在支化臂中具有内部官能团和/或延伸物(extender)基团。这些PEHAM树枝状化合物描述于2005年4月20日提交的US Serial No.10/594,776和2005年12月21日提交的US 11/630,044。
已知的是,农业中使用的各种希望的活性部分由于各种环境条件失去有效性或需要重复施用。下述参考文献讨论这些问题中的某些。在植物用载体中的活性部分处理的情况下,比如将其喷雾于植物叶子上,观察到的问题是希望活性部分的吸收和转移或活性物的光降解。已采用各种尝试来最小化上述结果,比如加入表面活性剂比如EthylanTMTU[Baker,Edward A.,等人,Pestic.Sci.34,167-182(1992)],或有机硅表面活性剂[Stevens,Peter J.G.,等人Pestic.Sci.38,237-245(1993)],或TinopalTM[Reddy,N.P.,等人,Pest Manag.Sci.64,909-915(2008)]。其它途径涉及通过用分散剂加入氧化亚铜和王铜来改善叶保留[Large,E.C.等人,Annals of Applied Biol.,33(1),54-63(1945),通过水来改善叶上局部分布[Hislop,E.C.等人,Ann.Appl.Biol.66,89-101(1970)],各种除草剂对完好叶角质层的穿透得以测量并发现对于数种活性物较低[Baker,Edward A.,Pestic.Sci.29,187-196(1990)],而咪唑喹啉酸的喷雾保留、叶面淋洗和在降雨条件下的流失经测定非常高[Reddy,Krishna N.,等人,Pestic.Sci.48,179-187(1996)]。
额外地,已研究紫外光导致的活性物光降解以试图通过数种基团最小化这种活性效力损失的效果,比如保护两性霉素B[Tufteland,Megan L.等人,Pest Manag.Sci.65,624-628(2009)],砜嘧磺隆[Scrano,Laura等人,Pestic.Sci.55,995-961(1999)],氯苯嘧啶醇[Sur,Nivedita等人,Pest Manag.Sci.56,289-292(2000)],氟氰戊菊酯[ChattopadhyhyaS.等人,Pestic.Sci.31,163-173(1991)],伏杀硫磷[Walia,S.等人,Pestic.Sci.25,1-9(1989)],氯乙氟灵[Saha,Tapas等人,Pest Manag.Sci.58,179-182(2001)],丙炔氟草胺[Kwon,Jeong-Wook,等人,Pest Manag.Sci.60,939-943(2004)],苄嘧磺隆-甲酯[Si,You-Bin,等人,Pest Manag.Sci.60,286-290(2003)],苯甲酰基苯脲[Marsella,Adam,等人,PestManag.Sci.56,789-794(2000)],和乙烯菌核利[Schick,Bernhard等人,Pestic.Sci.55,1116-1122(1999)]。一种方法是为活性物质屏蔽UV,比如通过中空二氧化硅纳米粒子的纳米粒子载体[Li,Zhu-Zhu等人,PestManag.Sci.63,241-246(2007)],用吸收剂化合物[Hussain,Manzoor等人,Pestic.Sci.28,345-355(1990)],草铵膦酸(glufosinate)[Kocher,Helmut等人,Pestic.Sci.37,155-158(1993)],和2-丙醇和12-羟基硬脂酸甲酯[Schwack,Wolfgang等人,Pestic.Sci.40,279-284(1994)]。
US专利6,939,831描述一种具有2-20,000亚磷酸/氮键的树枝状化合物与农业活性部分的用途。该组合物总是凝胶组合物,这限制其施用方法。
这些已知的农业活性部分有用性降低导致需要向植物重复施用活性部分,导致这些重复施用成本增加和所述农业活性部分的流失或土壤保留的环境问题。
明显地,希望的是向植物提供活性部分的方法,其降低UV降解效果,增加活性部分的溶解度和穿透,减少活性物的施用量或者避免重复施用以降低环境影响。
发明概要
本发明提供经挑选的预先已知的PEHAM树枝状聚合物。本发明的这些PEHAM树枝状聚合物包含至少一种下式的PEHAM树枝状化合物
式(I)
其中:
(C)意指由PETGE、PETriGE或TMPTGE组成的核心;
(FF)意指核心的焦点官能团组分(focal point functionalitycomponent),选自Et,OH,SH,NH2,CO2H,羧酸酯,直链或支链C1-C18烷基,芳基,芳基杂环部分,C1-C3烷氧基,三唑,C1-C18烷基酯,聚乙二醇和多氟化部分;
x独立地是0或1;
(BR)意指支化单元,如果p大于1,则(BR)可以是相同或不同的部分,选自DBA,DEA,DEIDA,DETA,DIA,IDA,TREN,TRIS,甲基丙烯酸酯,和PETriGE;
p是树枝状化合物中支化单元(BR)的总数并且是下述公式推演出的整数
其中:G是围绕核心的同心支化单元壳(代)数,其是1、2或3;
i是最终代G;
Nb是支化单元多重度;和
Nc是核心多重度且是1至4的整数;
条件是在x是1的情况下,Nc-x必须是1至3的整数;
(IF)意指内部官能团,其是OH;
q独立地是0或1至64的整数;
(EX)意指延伸物,如果m大于1,则(EX)可以是相同或不同的部分,选自氨基酸比如赖氨酸,聚(氨基酸)比如聚赖氨酸,寡聚乙二醇,二亚乙基四胺和高级胺类似物,作为5-元咪唑烷基衍生物保护的寡聚烷基烯胺,具有二个或更多不同或相同官能团的脂肪酸,不饱和的脂族和芳族二官能或多官能部分,EA,吗啉,二羧酸,EPC,IMAE,芳基二硫醇,二巯基烷烃,三唑类,DMI,二叠氮化物,联乙炔,吡咯烷酮,吡咯烷酮酯,氨基烷基咪唑啉,咪唑烷,聚(亚烷基咪唑烷),巯基烷基胺,羟基烷基胺或异质不饱和的脂族和芳族二官能或多官能部分;
m独立地是0或1至64的整数;
在q和m均大于1的情况下,(BR)和(EX)可以与另一部分交替出现或者按顺序与(BR)或(EX)的多个基团相继出现;
(TF)意指末端官能团,如果z大于1,则(TF)可以是相同或不同的部分,选自氨基,甲基氨基,乙基氨基,羟基乙基氨基,苄基氨基,巯基乙基氨基,二甲基氨基,二乙基氨基,二(羟基甲基)氨基,N-烷基化的氨基衍生物,N-芳基化的氨基衍生物,N-酰化的氨基衍生物,CO2-N(C1-C6烷基),羟基,巯基,羧基,羧酸盐,羧基C1-C18烷基,直链或支链C2-C18烯基,甲代烯丙基(methalkyl),酰胺基,卤代,脲,环氧乙烷基,氮丙啶基,噁唑啉基,咪唑啉基,吡咯烷酮,苄基,苯基,磺酸基,膦酸盐/酯,异氰酸盐/酯,异硫氰酸基,哌嗪基,乙基哌嗪基,丙烯酸盐/酯,甲基丙烯酸盐/酯,丙烯酰胺,叠氮化物,环氧化物,乙基亚胺,直链或支链C1-C18烷基,C1-C3烷氧基,C1-C18烷基酯,硫杂环丙烷(thiorane),吗啉基,保护的DETA,聚乙二醇,多氟化部分,和树枝状物;
z意指对于给定代G,1至(C)和(BR)可能的理论数的表面基团数,且由下述公式推演
z=NcNb G;
其中:G,Nb和Nc如上述定义;和
条件是存在(EX)或(IF)中至少一个;
与至少一种农业活性物质结合;和
存在至少一种农业上可接受的稀释剂或载体;和
其中农业活性物质的效力或活性持续时间得以增加。
这些特定的式(I)的PEHAM树枝状化合物与至少一种农业活性物质用于配制剂中,其用于农业意图,特别用于以各种方式增加农业活性物质效力。特别是,这些配制剂可用于:改善农业活性物质在配制剂中的溶解度,改善农业活性物质对植物表面的粘着和穿透,改善农业活性物质对植物或种子的耐水牢度,提供保护农业活性物质免于UV损害,增加农业活性物质的土壤穿透以到达植物根部或土壤下部分,或者降低农业活性物质的土壤粘着以到达植物根部或土壤下部分,或者降低植物或种子或土壤中的微生物对农业活性物质的酶促降解。配制剂的这些改善使得可以降低待施用农业活性物质的量或者减少配制剂重复施用的次数,其降低配制剂和农业活性物质的环境影响。
发明详述
术语定义
本申请中使用的下述术语如下文所定义,并且对于这些术语,单数包括复数。
amu意指原子质量单元
BR或(BR)意指支化单元
C或(C)意指树枝状化合物或树枝状物的核心
间-CPBA意指间-氯过氧苯甲酸
DCM意指二氯甲烷
DEA意指二乙醇胺
DEIDA意指亚氨基二乙酸二乙酯
DETA意指二亚乙基三胺
DBA意指二苄胺
DI意指去离子水
DMI意指衣康酸二甲酯
DMSO意指二甲亚砜
EA意指乙醇胺
EDA意指乙二胺
EPC意指N-哌嗪羧酸乙酯
EPI意指表氯醇,通常在使用前进一步蒸馏
Et意指乙基
EtOH意指乙醇
EX或(EX)意指延伸物(extender)
FF或(FF)意指核心的焦点官能团组分
G意指树枝状化合物代,其由围绕核心的同心支化单元壳数代表(通常自核心按顺序计数)
g意指克
h意指小时
HPLC意指高压液体色谱法
IDADS意指亚胺基二乙酸二钠盐
IDA意指亚胺基二乙酸
IF或(IF)意指内部官能团
IMAE意指2-咪唑烷基-1-氨基乙烷
IR(或FTIR)意指红外光谱测定法
L意指升
MeOH意指甲醇
mg意指毫克
min意指分钟
mL意指毫升
MWA意指微波辅助
N-SIS意指纳米尺度立体诱导的化学计量
PAMAM意指聚(酰胺基胺),包括线性和支化的聚合物或具伯胺端基的树枝状化合物
PEHAM意指聚(醚羟胺)树枝状化合物
PEI意指聚(乙烯亚胺)
PETAE意指季戊四醇四烯丙基醚
PETGE意指季戊四醇四缩水甘油基醚
百分比或%意指重量,除非另有说明比如重量/体积(w/v)等
PIPZ意指哌嗪
POPAM意指PAMAM树枝状物围绕的PPI核心
PPI意指聚(丙烯亚胺)
RT意指环境温度或室温,约20-25℃
SEC意指体积排阻色谱法
SIS意指立体诱导(sterically induced)的化学计量
TF意指末端官能团
TLC意指薄层色谱法
TMPTGE意指三羟甲基丙烷三缩水甘油基醚
TREN意指三(2-氨基乙基)胺
TRIS意指三(羟基甲基)氨基甲烷
UF意指超滤分离
UV-vis意指紫外可见光谱
常常需要特别优化农业化学品生物利用度以确保最低可能施用率下的最佳生物学效力和对环境的最低影响。配制剂施用还必须具有在作物上的均匀分布,容易用水稀释(农业人员优选溶剂),最佳生物学效力,操作者容易且安全的处理,和最低的可能环境影响。该被证明是难以实现的,因为气候、作物、病虫害和土壤在生长区域广泛地变化。
农业中使用的配制剂包含:活性成分(其特性大大影响配制剂能够采取何种形式,比如溶解度、亲脂性、水解稳定性、光降解等),其它成分比如表面活性剂,载体,赋形剂(目前树枝状化合物充当活性物载体,但其除该功能还具有其他功能)。配制剂类型取决于期望的生物学靶标和需要的施用方法。一般配制剂类型是:WG-水分散粒剂;SC-浓悬浮剂;EC-乳油;和OD-油分散剂。
本发明描述PEHAM树枝状化合物配制剂,其用于农业施用比如调节和控制植物、种子、昆虫、微生物或动物病虫害的发展。
本发明的某些方面涉及以各种方式增加农业活性物质效力,比如通过改善农业活性物质在配制剂中的溶解度,通过改善农业活性物质对植物表面的粘着,通过改善农业活性物质对植物或种子的耐水牢度(包括活性物质被雨水自植物洗去的耐雨牢度),通过改善农业活性物质向植物组织中的穿透(吸收),通过提供保护农业活性物质免受UV损害,通过增加农业活性物质的土壤穿透以到达植物根部或土壤下部分,或者通过降低农业活性物质的土壤粘着以到达植物根部或土壤下部分,或者降低植物或种子或土壤中的微生物对农业活性物质的酶促降解。
PEHAM树枝状聚合物的化学结构
PEHAM树枝状聚合物结构可以是树枝状化合物,树枝状物,树枝状接枝物,屋顶(tecto)(树枝状)聚合物或其它树枝状结构。所述树枝状聚合物的许多实例存在于文献中,比如描述于Dendrimers and otherDendritic Polymers,编著J.M.J.Fréchet,D.A.Tomalia,John Wiley和Sons出版,(2001)和其它类似来源中的那些。
这些PEHAM树枝状聚合物能够是任意物理形状,比如例如球、棒、管或者可能的任意其它形状。内部结构可以具有内部可裂解的键(比如二硫化物),用于包囊的空隙体积,或内部官能团(IF)比如氢氧化物或其它基团以与活性成分结合。额外地,PEHAM树枝状聚合物能够是树枝状物。该树枝状物能够具有希望的任意树枝状聚合物组分。
本发明树枝状聚合物是PEHAM树枝状化合物,其包括PEHAM树枝状物。这些PEHAM树枝状化合物具有如上文所讨论的结构,并进一步描述如下。
用来制备PEHAM树枝状聚合物的一般合成
本发明的PEHAM树枝状聚合物具有下述通式:
式(I)
其中:
(C)意指由PETGE、PETriGE或TMPTGE组成的核心;
(FF)意指核心的焦点官能团组分,选自Et,OH,SH,NH2,CO2H,羧酸酯,直链或支链C1-C18烷基,芳基,芳基杂环部分,C1-C3烷氧基,三唑,C1-C18烷基酯,聚乙二醇和多氟化部分;
x独立地是0或1;
(BR)意指支化单元,如果p大于1,则(BR)可以是相同或不同的部分,选自DBA,DEA,DEIDA,DETA,DIA,IDA,TREN,TRIS,甲基丙烯酸盐/酯,和PETriGE;
p是树枝状化合物中的支化单元(BR)的总数且是下述公式推演出的整数
其中:G是围绕核心的同心支化单元壳(代)数,其是1、2或3;
i是最终代G;
Nb是支化单元多重度;和
Nc是核心多重度和是1至4的整数;
条件是在x是1的情况下,Nc-x必须是1至3的整数;
(IF)意指内部官能团,其是OH;
q独立地是0或1至64的整数;
(EX)意指延伸物,如果m大于1,则(EX)可以是相同或不同的部分,选自氨基酸比如赖氨酸,聚(氨基酸)比如聚赖氨酸,寡聚乙二醇,二亚乙基四胺和高级胺类似物,作为5-元咪唑烷基衍生物保护的寡聚烷基烯胺,具有二个或更多不同或相同官能团的脂肪酸,不饱和的脂族和芳族二官能或多官能部分,EA,吗啉,二羧酸,EPC,IMAE,芳基二硫醇,二巯基烷烃,三唑类,DMI,二叠氮化物,联乙炔,吡咯烷酮,吡咯烷酮酯,氨基烷基咪唑啉,咪唑烷,聚(亚烷基咪唑烷),巯基烷基胺,羟基烷基胺或异质不饱和的脂族和芳族二官能或多官能部分;
m独立地是0或1至64的整数;
在q和m均大于1的情况下,(BR)和(EX)可以与另一部分交替出现或者按顺序与(BR)或(EX)的多个基团相继出现;
(TF)意指末端官能团,如果z大于1,则(TF)可以是相同或不同的部分,选自氨基,甲基氨基,乙基氨基,羟基乙基氨基,苄基氨基,巯基乙基氨基,二甲基氨基,二乙基氨基,二(羟基甲基)氨基,N-烷基化的氨基衍生物,N-芳基化的氨基衍生物,N-酰化的氨基衍生物,CO2-N(C1-C6烷基),羟基,巯基,羧基,羧酸盐,羧基C1-C18烷基,直链或支链C2-C18烯基,甲代烯丙基,酰胺基,卤代,脲,环氧乙烷基,氮丙啶基,噁唑啉基,咪唑啉基,吡咯烷酮,苄基,苯基,磺酸基,膦酸盐/酯,异氰酸盐/酯,异硫氰酸基,哌嗪基,乙基哌嗪基,丙烯酸盐/酯,甲基丙烯酸盐/酯,丙烯酰胺,叠氮化物,环氧化物,乙基亚胺,直链或支链C1-C18烷基,C1-C3烷氧基,C1-C18烷基酯,硫杂环丙烷,吗啉基,保护的DETA,聚乙二醇,多氟化部分,和树枝状物;
z意指对于给定代G,1至(C)和(BR)可能的理论数的表面基团数,且由下述公式推演
z=NcNb G;
其中:G,Nb和Nc如上述定义;和
条件是存在(EX)或(IF)中至少一种;
与至少一种农业活性物质结合;和
存在至少一种农业上可接受的稀释剂或载体;和
其中农业活性物质的效力或活性持续时间得以增加。
从而,本发明的任意PEHAM树枝状化合物的G是0、1、2或3,优选0、1和2。(EX)基团能够下面所列那些中任意种,但是特别优选的是不饱和的脂族和芳族二官能或多官能部分,EA,吗啉,二羧酸,EPC,IMAE,芳基二硫醇,二巯基烷烃,三唑类,DMI,二叠氮化物,联乙炔,吡咯烷酮,吡咯烷酮酯,氨基烷基咪唑啉,咪唑烷,聚(亚烷基咪唑烷),巯基烷基胺,和羟基烷基胺;且更优选的是三唑,哌嗪或吗啉。(TF)基团能够是上述中任意种,但是优选OH,CO2Et,羧基盐,CO2-N(四烷基)和NH2。(BR)基团是上述那些,但是优选DEA,DEIDA,DETA,TREN,和TRIS。(FF)基团是Et和OH。优选存在一个或多个(IF)基团,其中(IF)是OH。
式(I)的PEHAM能够通过丙烯酸-胺反应体系制备,其包括:
A.将丙烯酸官能核心与胺官能延伸物反应,比如如下所示:
(C)+(EX)→(C)(EX)(TF)
其中(C)=丙烯酸官能核心比如TMPTA;(EX)=胺官能延伸物比如PIPZ;和(TF)=胺;和
B.将(C)(EX)(TF1)的胺官能延伸核心试剂与丙烯酸官能支化单元试剂(BR)反应,如下所示:
(C)(EX)(TF1)+(BR)→(C)(EX)(BR)(TF2)
其中(C)=TMPTA;(EX)=PIPZ;(TF1)=胺;(BR)=TMPTA;和(TF2)=丙烯酸盐/酯;和
其中对于步骤A和B
将延伸物(EX)基团加至核心,(EX)/(C)的摩尔比定义为延伸物分子(EX)摩尔与简单核心、骨架核心、超级核心或者目前代结构(也即Nc)的反应性官能团的摩尔的比例,在希望的完全覆盖的情况下使用过量的(EX);
将支化单元(BR)加至简单核心、骨架核心、超级核心或目前代结构,(BR)/(C)定义为支化单元分子(BR)的摩尔与简单核心、骨架核心、超级核心或目前代结构(也即Nc)上反应性官能团的摩尔的比例,其中在希望完全覆盖的情况下使用过量(BR);和
将支化单元(BR)或延伸物(EX)加至核心、骨架核心、超级核心或目前代产品的水平能够通过添加摩尔比或通过N-SIS得以控制。
制备式(I)的树枝状聚合物的方法可以是开环反应体系,其包括:
A.将环氧官能核心与胺官能延伸物反应,比如如下所示:
(C)+(EX)→(C)(IF1)(EX)(TF1)
其中(C)=环氧官能核心比如PETGE;(IF1)=内部羟基(OH);(EX)=哌嗪(PIPZ);(TF1)=胺;和
B.将胺官能扩展核心试剂(C)(IF1)(EX)(TF1)与环氧官能支化单元试剂反应,比如如下所示:
(C)(IF1)(EX)(TF1)+(BR)→(C)(IF1)(EX)(IF2)(BR)(TF2)
其中(C)=PETGE;(IF1)=如权利要求1所定义的内部官能团部分,比如OH;(EX)=如权利要求1所定义的延伸物部分,比如PIPZ;(TF1)=胺;(BR)=环氧官能支化单元试剂比如PETGE;和(IF2)=如权利要求1所定义的内部官能团部分,比如OH;(TF2)=胺;和
其中对于两种步骤A和B
将延伸物(EX)基团加至核心,(EX)/(C)的摩尔比定义为延伸物分子(EX)摩尔与简单核心、骨架核心、超级核心或目前代结构(也即Nc)上反应性官能团摩尔的比例,其中在希望完全覆盖的情况下使用过量(EX);
将支化单元(BR)加至简单核心、骨架核心、超级核心或目前代结构,(BR)/(C)定义为支化单元分子(BR)摩尔与简单核心、骨架核心、超级核心或目前代结构(也即Nc)上反应性官能团摩尔的比例,在希望完全覆盖的情况下使用过量的(BR);和
将支化单元(BR)或延伸物(EX)加至核心、骨架核心、超级核心或目前代产品的的水平,能够通过添加摩尔比或通过N-SIS得以控制。
正交化学途径是将含叠氮化物的(C)和(BR)加成至含炔的(C)和(BR)的1,3-偶极环-加成。含炔(C)可以具有1至Nc个炔部分,而含炔(BR)可以具有1至Nb-1个炔部分。(C)或(BR)中存在的其它反应性基团能够前文所列的(BR)基团中的任意种。含叠氮化物的(C)和(BR)通过具有叠氮化阴离子的环氧环亲核开环产生。这些反应性基团的后续反应能够提供对新(BR)或(TF)部分的三唑连接,使用Michael Malkoch等人,在J.Am.Chem.Soc.127,14942-14949(2005)中描述的"click"化学。
WO 2007/149501教导MWA合成,与热处理相比,其展示出乎意料的且显著的优势。观察到,MWA在更温和的条件下产生更高纯度的树枝状聚合物产品(也即,树枝状化合物/树枝状物),反应时间更短(分相对天),并且需要仅化学计量的量或稍微过量的反应试剂。将作为原料的树枝状聚合物或者希望的(C)与BR或EX反应,获得所希望的树枝状聚合物产品。如果反应物不充当溶剂,则能够使用适宜的溶剂。与在先的热反应相比更温和的反应条件导致更少的副产物,所希望的树枝状聚合物产品的较少的纯化步骤。与在先的热过程比较,反应时间显著减少。从而,对于制备希望的产品来说,该MWA合成运行成本更低。
上述过程中的任意种能够用来制备式(I)的PEHAM树枝状化合物。
作为2005年4月20日提交的US Serial No.10/594,776和2005年12月21日提交的US 11/630,044的PEHAM树枝状化合物的选择发明,该式(I)令人惊讶地有效用于这些农业配制剂中。它们的尺寸、对于它们的低G的较高(TF)保持成本更低,更易制备,且为配制剂赋予希望特性。
包囊的或与这些树枝状化合物结合的农业活性物质可以选自很大范围的符合所希望意图的可能部分。所述物质包括但不限于体内或体外或离体地用于植物或其种子、或植物病虫害、生长激素类(growthhormones)或微生物、病毒和任意生命体系中,该物质能够与这些PEHAM树枝状化合物结合,而并不可察觉地干扰树枝状化合物的物理完整性。
本发明配制剂的农业活性物质是任意物质,其可用于施用至植物或其种子以增加作物产量、减少竞争性植物、矮化或灭除杂草,或者用于预防或处理病虫害,并且该农业活性物质能够与PEHAM树枝状化合物结合,而并不可察觉地干扰PEHAM树枝状化合物的物理完整性。例如,Fe,Gd,或Mn;激素类;生物学应答调节剂,比如白细胞介素,干扰素类,病毒和病毒片段;农药,包括杀微生物剂,杀藻剂,驱蠕虫剂,杀螨剂,杀昆虫剂,吸引剂,驱避剂;除草剂和/或杀真菌剂,比如阿维菌素,乙酰甲胺磷,乙草胺,三氟羧草醚,甲草胺,莠去津,氟草胺,苯菌灵,灭草松,克菌丹,克百威,氯化苦,甲萘威,百菌清,百菌清,毒死蜱,氯磺隆氰草津,氢氧化铜,硫酸铜,三环锡,氯氰菊酯,茅草枯,2,4-二氯苯氧基乙酸(2,4-D),DCPA,二嗪磷,麦草畏,禾草灵,二甲吩草胺,除虫脲,地乐酚,敌草隆,茵多酸,茵草敌,乙烯利,福美铁,吡氟禾草灵,草甘膦,氟吡禾灵,马拉硫磷,代森锰锌,MCPP,甲霜灵,精甲霜灵,异丙甲草胺,精异丙甲草胺,嗪草酮,甲基砷酸钠,萘草胺;二甲戊灵,氯菊酯,氨氯吡啶酸,毒草胺,敌稗,烯禾啶,西玛津,精异丙甲草胺,甲磺草胺,sulfosate,双硫磷,特丁硫磷,三氯吡氧乙酸,氟乐灵,嗪氨灵,和代森锌。
通常,可以作为农业活性物质加入本发明配制剂的农药和/或生长调节活性物质是列于任意植保手册的那些,例如L'Index Phytosanitaire(Technical Directorate of the Association de Coordination TechniqueAgricole或A.C.T.A.出版)或The Pesticide Manual(the British CropProtection Council)或The Electronic Pesticide Manual(the British CropProtection Council)。在本发明配制剂中能够,单独或与其它活性物质组合,用作农业活性物质的一些植物生长调节剂是:S-诱抗素;ACC;环丙嘧啶醇;aviglycine;benzofluor;苄基腺嘌呤;芸苔素内酯;buminafos;仲丁灵;氰氨化钙;甲萘威;香芹酮;氯芴羧酸(chlorfluren);整形醇;矮壮素;三丁氯苄膦(chlorphonium);氯苯胺灵;ciobutide;苯哒嗪(clofencet);氯贝酸;座果酸;氯苯氧乙酸;单氰胺;环丙酰胺酸;放线菌酮;环丙磺草胺(cyprosulfamide);2,4-D;丁酰肼;2,4-滴丁酸;伐草磷;dichlorflurenol;2,4-滴丙酸;调呋酸;噻节因;茵多酸;epocholeone;乙烯硅;乙烯利;吲熟酯;乙烯;2,4,5-涕丙酸;杀雄嗪(fenridazon);氟节胺;增糖胺;芴丁酯;呋嘧醇;氯吡脲;杀木膦;赤霉酸;赤霉素;乙二肟;增甘膦;增产肟;holosulf;噁霉灵;IAA;IBA;抗倒胺;isopyrimol;茉莉酸;karetazan;糠氨基嘌呤;砷酸铅;抑芽丹;氟磺酰草胺;mepiquat;脱叶亚磷(merphos);磺菌威;1-甲基环丙烯;甲氧隆;α-萘乙酸;萘乙酰胺(naphthaleneacetamide);1-萘酚;萘氧乙酸;烯腺嘌呤;多效唑;五氯苯酚;哌壮素(piproctanyl);环烷酸钾;调环酸;prohydrojasmon;苯胺灵;pydanon;杀雄啉;环烷酸钠;2,4,5-涕;四环唑;噻苯隆;抑芽唑;tribufos;2,3,5-三碘苯甲酸;抗倒酸(trinexapac);烯效唑;和玉米素。
在本发明配制剂中能够,单独或与其它活性物质组合,用作农业活性物质的某些杀真菌剂物质是:邻苯基苯酚;8-羟基喹啉;AC 382042;Ampelomyces quisqualis;活化酸(acibenzolar);acypetacs;aldimorph;烯丙醇;ametoctradin;吲唑磺菌胺(amisulbrom);ampropylfos;敌菌灵;金色制霉素(aureofungin);氧环唑;嘧菌酯;氧化福美双(azithiram);嘧菌酯;枯草芽孢杆菌(Bacillus subtilis);多硫化钡;苯霜灵;精苯霜灵;麦锈灵;苯菌灵;醌肟腙;bentaluron;苯噻菌胺(benthiavalicarb);苯扎氯铵;benzamacril;benzamorf;苯甲羟肟酸;bethoxazin;乐杀螨;联苯;联苯三唑醇;硫氯酚;联苯唑酰胺(bixafen);灭瘟素;硼砂;波尔多液;啶酰菌胺;糠菌唑;乙嘧酚磺酸酯;苏打波尔多液;丁硫啶;丁胺;萎锈灵;石硫合剂;敌菌丹;克菌丹;吗菌威;多菌灵;萎锈灵;环丙酰菌胺(KTU 3616);香芹酮;Cheshunt混合物;CGA 279202;灭螨猛;chlobenthiazone;chloraniformethan;四氯对醌;chlorfenazole;氯代二硝基萘;氯苯甲醚;氯化苦;百菌清;四氯喹喔啉;乙菌利;咪菌酮;克霉唑;乙酸铜;碱式碳酸铜;氢氧化铜;环烷酸铜;油酸铜;王铜;硅酸铜;硫酸铜;硫酸铜-碱性;铬酸铜锌;甲酚;硫杂灵(cufraneb);cuprobam;氧化亚铜;氰霜唑;环菌胺;放线菌酮;环氟苄酰胺;霜脲氰;氰菌灵;环丙唑醇;嘧菌环胺;棉隆;二溴氯丙烷;咪菌威;癸磷锡(decafentin);保果鲜(dehydroacetic acid);苯氟磺胺;二氯萘醌;双氯酚;菌核利;苄氯三唑醇;双氯氰菌胺;哒菌酮;氯硝胺;双氯酚;双氯氰菌胺;乙霉威;焦碳酸二乙基酯;苯醚甲环唑;野燕枯;野燕枯硫酸甲酯盐;氟嘧菌胺;二甲嘧酚;烯酰吗啉;二甲苯氧菌胺;烯唑醇;R-烯唑醇;消螨通;二硝基巴豆酸酯;二硝基巴豆酸酯-4;二硝基巴豆酸酯-6;敌菌死(dinocton);硝戊酯(dinopenton);硝辛酯(dinosulfon);硝丁酯(dinoterbon);二苯胺;双硫氧吡啶(dipyrithione);双硫仑;灭菌磷;灭菌磷;二氰蒽醌;二硝酚;十二环吗啉;十二环吗啉乙酸盐;多果定;多果定游离碱;肼菌酮;敌瘟磷;氟环唑(BAS 480F);乙环唑;代森硫磺;噻唑菌胺;磺菌威(ethasulfocarb);乙嘧酚;乙氧喹啉;2,3-二羟基丙基硫醇乙基汞;乙酸乙基汞;溴化乙基汞;氯化乙基汞;磷酸乙基汞;溴化(3-乙氧基丙基)汞;土菌灵;噁唑菌酮;咪唑菌酮;敌磺钠;咪菌腈;氯苯嘧啶醇;腈苯唑;三苯锡(fenfin);甲呋酰胺;环酰菌胺;种衣酯;稻瘟酰胺;拌种咯;苯锈啶;丁苯吗啉;三苯锡;三苯基乙酸锡;三苯基氢氧化锡;福美铁;嘧菌腙;氟啶胺;咯菌腈;氟酰菌胺;氟吗啉;氟吡菌胺;氟吡菌酰胺;氟氯菌核利;三氟苯唑;氟嘧菌酯;氟喹唑;氟硅唑;磺菌胺;氟噻菌灵(flutianil);氟酰胺;粉唑醇;灭菌丹;甲醛;乙膦酸;三乙膦酸铝;麦穗宁;呋霜灵;呋吡菌胺;二甲呋酰胺;呋菌唑;呋醚唑;糠醛;拌种胺;呋甲硫菌灵;尖孢镰孢(Fusariumoxysporum);绿粘帚霉(Gliocladium virens);果绿啶;灰黄霉素;双胍辛;双胍辛乙酸盐;GY-81;丙烯酸喹啉酯;六氯苯;六氯丁二烯;己唑醇;环菌磷(hexylthiofos);汞加芬;8-羟基喹啉;噁霉灵;ICIA0858;IKF-916;抑霉唑;抑霉唑硫酸盐;亚胺唑;双胍辛胺;双胍辛胺乙酸盐;双胍三辛烷基苯磺酸盐(双胍辛胺三[Albesilate]);碘甲烷;种菌唑;异稻瘟净;异菌脲;缬霉威;稻瘟灵;吡酰菌胺(isopyrazam);异噻菌胺(isotianil);isovaledione;春雷霉素;春雷霉素盐酸盐水合物;醚菌酯;代森锰铜;代森锰锌;双炔酰菌胺;代森锰;邻酰胺;甲威苯咪(mecarbinzid);嘧菌胺;灭锈胺;meptyldinocap;氯化汞;氧化汞;氯化亚汞;甲霜灵;精甲霜灵;百亩酸(metam);威百亩;metazoxolon;叶菌唑;磺菌威;呋菌胺;氯化2-甲氧基乙基汞;溴甲烷;异硫氰酸甲酯;苯甲酸甲基汞盐;双氰胺化甲基汞(methylmercury dicyandiamide);五氯苯酚甲基汞盐;代森联;苯氧菌胺(SSF-126);苯菌酮(metrafenone);噻菌胺;代森环;MON65500;腈菌唑;腈菌唑;甲菌利;N-(乙基汞)-对-甲苯磺酰基苯胺;代森钠;环烷酸;那他霉素(natamycin);二(二甲基二硫代氨基甲酸)镍;硝基苯乙烯;酞菌酯;氟苯嘧啶醇;OCH;辛噻酮;呋酰胺;油酸(脂肪酸);肟醚菌胺;噁霜灵;喹啉铜;噁咪唑(oxpoconazole);氧化萎锈灵;稻瘟酯;戊菌唑;戊菌隆;己唑菌胺(penflufen);五氯苯酚;月桂酸五氯苯酯;吡噻菌胺(penthiopyrad);perfurazoate;8-苯基-汞氧基喹啉;苯基汞脲;乙酸苯汞;氯化苯汞;邻苯二酚苯基汞衍生物;苯基汞硝酸盐;苯基汞水杨酸盐;邻苯基苯酚;Phlebiopsis gigantea;氯瘟磷;四氯苯酞;啶氧菌酯;哌丙灵;代森福美锌;多抗霉素B;多抗霉素;polyoxorim;叠氮化钾;羟基喹啉硫酸钾;多硫化钾;硫氰化钾;烯丙苯噻唑;咪鲜胺;腐霉利;霜霉威;霜霉威盐酸盐;丙环唑;丙森锌;丙氧喹啉;硫菌威;丙硫菌唑;吡喃灵;吡唑醚菌酯;唑胺菌酯;唑菌酯;吡菌磷;吡菌苯威(pyribencarb);稗草丹;啶菌腈;啶斑肟;嘧霉胺;咯喹酮;甲氧氯吡啶(pyroxychlor);氯吡呋醚;羟基喹啉基乙酮(quinacetol);醌菌腙(quinazamid);quinconazole;苯氧喹啉(quinoxyfen);五氯硝基苯;rabenzazole;RH-7281;防霉胺(防霉胺(salicylanilide));仲丁胺;环丙唑菌胺(sedaxane);硅噻菌胺;硅氟唑;叠氮化钠;邻苯基苯酚钠;五氯苯酚钠;2-苯基苯氧化钠;五氯苯酚钠;多硫化钠;螺环菌胺(KWG 4168);Streptomyces griseoviridis;链霉素;硫磺;戊苯砜(sultropen);焦油;TCMTB;戊唑醇;tebufloquin;叶枯酞;四氯硝基苯;tecoram;四氟醚唑;噻菌灵;thiadifluor;噻菌腈;噻氟菌胺;thiochlorfenphim;硫柳汞;硫菌灵;甲基硫菌灵;克杀螨;福美双;噻唑菌酰胺;tioxymid;甲基立枯磷;甲苯氟磺胺;甲苯基汞乙酸盐(tolylmercury acetate);三唑酮;三唑醇;威菌磷;嘧菌醇(triarimol);叶锈特;咪唑嗪;三丁基锡氧化物(tributyltin oxide);水杨菌胺;哈茨木霉(Trichoderma harzianum);三环唑;十三吗啉;肟菌酯;氟菌唑;嗪氨灵;灭菌唑;烯效唑;精烯效唑;有效霉素;缬氨菌酯(valifenalate);乙烯菌核利;氰菌胺;环烷酸锌;代森锌;福美锌;苯酰菌胺;具有(E,E)-2-(2-(1-(1-(2-吡啶基)丙基氧基亚氨基)-1-环丙基甲基氧基-甲基)苯基)-3-乙氧基丙烯酸甲基酯的化学命名的化合物;和3-(3,5-二氯苯基)-4-氯吡唑。
在本发明配制剂中,可以单独或与其它活性物质尤其是农药组合使用,用作农业活性物质的杀昆虫剂、杀螨剂和杀线虫剂活性物质的实例是:阿维菌素;乙酰甲胺磷;啶虫脒;家蝇磷;acetoprole;氟丙菊酯;丙烯腈;涕灭威;棉铃威;涕灭砜威;艾氏剂;烯丙菊酯[(1R)异构体];α-氯氰菊酯;allosamidin;除害威;α-氯氰菊酯;α-硫丹;赛硫磷;灭害威;三乙胺硫磷(amiton);双甲脒;新烟碱;athidathion;阿维菌素(avermectin)B1及其衍生物;印楝素;甲基吡噁磷;益棉磷;保棉磷;保棉磷;偶氮硫磷(azothoate);苏云金杆菌;氟硅酸钡;熏虫菊酯(barthrin);噁虫威;丙硫克百威;杀虫磺;高效氟氯氰菊酯;高效氯氰菊酯;联苯肼酯;联苯菊酯;生物烯丙菊酯;生物烯丙菊酯(S-环戊烯基异构体);bioethanomethrin;生物氯菊酯;生物苄呋菊酯;双三氟虫脲;硼砂;硼酸;bromfenvinfos;溴西克林;溴滴滴涕(bromo-DDT);溴硫磷;乙基溴硫磷;合杀威;噻嗪酮;畜虫威;butathiofos;丁酮威;丁酯膦;丁酮砜威;硫线磷;砷酸钙;石硫合剂;毒杀芬;氯苯虫威(carbanolate);甲萘威;克百威;二硫化碳;四氯化碳;三硫磷;丁硫克百威;杀螟丹;杀螟丹盐酸盐;氯虫苯甲酰胺;chlorbicyclen;氯丹;开蓬;杀虫脒;氯氧磷;虫螨腈;毒虫畏;氟啶脲;氯甲硫磷;氯仿;氯化苦;氯辛硫磷;chlorprazophos;毒死蜱;甲基毒死蜱;虫螨磷;环虫酰肼;瓜叶菊素I;瓜叶菊素Ⅱ;瓜叶菊素;顺式苄呋菊酯(cismethrin);除线威;氯生太尔;噻虫胺;噻虫胺;乙酰亚砷酸铜;砷酸铜;环烷酸铜;油酸铜;蝇毒磷;冰晶石;Cryomazine;杀螟腈;氰化钙;氰化钠;畜虫磷;克罗米通;巴毒磷;育畜磷;冰晶石;苯腈膦;杀螟腈;果虫磷;氰虫苯甲酰胺(cyantraniliprole);氰虫苯甲酰胺(cyantraniliprole);环虫菊酯;乙氰菊酯;氟氯氰菊酯;氯氟氰菊酯;氯氰菊酯;苯醚氰菊酯[(1R)反式异构体];13-氟氯氰菊酯;13-氯氰菊酯;灭蝇胺;畜蜱磷;棉隆;滴滴涕;decarbofuran;溴氰菊酯;田乐磷;田乐磷-O;田乐磷-S;内吸磷;甲基内吸磷;内吸磷-O;甲基内吸磷-O;内吸磷-S;甲基内吸磷-S;砜吸磷;丁醚脲;氯亚胺硫磷;硅藻土;二嗪磷;异氯磷;除线磷;1,2-二氯丙烷;敌敌畏;三氯杀螨醇;dicresyl;百治磷;环虫腈;狄氏剂;除虫脲;dilor;四氟甲醚菊酯;甲氟磷;地麦威;乐果;苄菊酯;甲基毒虫畏;敌蝇威;敌蝇威;消螨酚;硝丙酚(dinoprop);戊硝酚;呋虫胺;苯虫醚;蔬果磷;二氧威;敌噁磷;乙拌磷;dithicrofos;d-柠檬烯;多拉克丁;二硝酚;DPXJW062和DP;α-蜕皮素;蜕皮甾酮;甲氨基阿维菌素;多杀威;右旋烯炔菊酯[(EZ)-(1R)异构体];硫丹;ENT 8184;苯硫膦;因毒磷;异狄氏剂;苯硫膦;epofenonane;依立诺克丁;S-氰戊菊酯;etaphos;乙硫苯威;乙硫磷;益硫磷;灭线磷;甲酸乙酯;乙基-DDD;二溴乙烷;二氯乙烷;乙虫腈[化学名:5-氨基-3-氰基-1-(2,6-二氯-4-三氟甲基苯基)-4-乙基亚磺酰基吡唑];环氧乙烷;醚菊酯;乙螨唑;乙嘧硫磷;EXD;伐灭磷;苯线磷;抗螨唑;皮蝇磷;二乙基苯酚甲基氨基甲酸酯(fenethacarb);五氟苯菊酯;杀螟硫磷;仲丁威;fenoxacrim;苯氧威;吡氯氰菊酯;甲氰菊酯;丰索磷;倍硫磷;倍硫磷-乙酯;氰戊菊酯;氟虫腈和芳基吡唑类化合物;氟啶虫酰胺;氟苯虫酰胺;flucofuron;氟环脲;氟氰戊菊酯;flufenerim;氟虫脲;三氟醚菊酯;氟氯苯菊酯;三氟醚菊酯;氟胺氰菊酯(fluvalinate);地虫硫膦;伐虫脒;formparanate;伐虫脒盐酸盐;安硫磷;丁苯硫磷;磷吡酯(fospirate);丁硫环磷;呋线威;抗虫菊酯(furethrin);精高效氯氟氰菊酯;林丹;GY-81;苄螨醚;氯虫酰肼;六六六;狄氏剂;七氯;庚烯磷;速杀硫磷;氟铃脲;六氟硅酸钠;艾氏剂;氟蚁腙;氰化氢;烯虫乙酯;hyquincarb;吡虫啉;炔咪菊酯;茚虫威;碘甲烷;丰丙磷;氯唑磷;碳氯灵;水胺硫磷;异艾氏剂;异柳磷;甲基异柳磷;异丙威;稻瘟灵;异拌磷;异硫氰酸甲酯;噁唑磷;依维菌素;茉酮菊素I;茉酮菊素Ⅱ;碘硫磷;保幼激素I;保幼激素II;保幼激素III;克来范(kelevan);烯虫炔酯;高效氯氟氰菊酯;月桂酸五氯苯酯;砷酸铅;lepimectin;溴苯膦;林丹;lirimfos;虱螨脲;噻唑磷;马拉硫磷;MB-599;特螨腈;叠氮磷(mazidox);灭蚜磷;四甲磷;灭蚜硫磷;地胺磷;氯化亚汞;mesulfenfos;氰氟虫腙;虫螨畏;甲胺磷;杀扑磷;甲硫威;methocrotophos;灭多威;烯虫酯;甲氧滴滴涕;甲氧虫酰肼;溴甲烷;三氯乙烷;二氯甲烷;甲氧苄氟菊酯;速灭威;噁虫酮;速灭磷;兹克威;milbemectin及其衍生物;密比霉素肟;丙胺氟磷;灭蚁灵;久效磷;茂硫磷;莫昔克丁(moxidectin);萘肽磷;二溴磷;萘;烟碱;氟蚁灵;烯啶虫胺;nithiazine;戊氰威;氟酰脲;多氟脲;石油;焦油;油酸;氧乐果;杀线威;亚砜磷;异亚砜磷;砜拌磷;玫烟色拟青霉(Paecilomyces fumosoroseus);对-二氯苯;对硫磷;甲基对硫磷;氟幼脲;五氯苯酚;五氯苯酚钠;氯菊酯;芬硫磷;苯醚菊酯[(1R)-反式异构体];稻丰散;甲拌磷;伏杀硫磷;硫环磷;亚胺硫磷;磷胺;增效醚;膦;磷化铝;磷化镁;磷化锌;氯硫磷(phosnichlor);磷胺;膦;辛硫磷;甲基辛硫磷;pirimetaphos;抗蚜威;嘧啶磷;甲基嘧啶磷;石硫合剂;三氯杀虫酯;亚砷酸钾;硫氰化钾;精滴滴涕(pp′-滴滴涕);炔丙菊酯;早熟素I;早熟素II;早熟素III;primidophos;丙溴磷;profluthrin;蜱虱威;猛杀威;丙虫磷;胺丙畏;残杀威;乙噻唑磷(prothidathion);丙硫磷;发硫磷;protrifenbute;吡唑硫磷;pyrafluprole;吡菌磷;pyresmethrin;除虫菊素I;除虫菊素Ⅱ;除虫菊素(菊酯、除虫菊酯、除虫菊);吡蚜酮;哒螨灵;三氟甲吡醚;哒嗪硫磷;七氟虫酰胺(pyrifluquinazon);嘧螨醚;嘧啶磷(pyrimitate);pyriprole;吡丙醚;苦木提取物(quassia);喹硫磷;喹硫磷-甲酯;quinothion;雷复沙奈(rafoxanide);苄呋菊酯;RH-2485;鱼藤酮;RU 15525;鱼尼汀(ryania);赛藜芦;八甲磷;司拉克丁(selamectin);氟硅菊酯;硅胶;亚砷酸钠;氟化钠;六氟硅酸钠;硫氰化钠;苏硫磷;乙基多杀菌素;多杀霉素;螺特杀(spiromesifen);螺虫乙酯;sulcofuron;sulcofuron-钠盐;氟虫胺;治螟磷;氟啶虫胺腈(sulfoxaflor);硫酰氟;硫丙磷;氟胺氰菊酯;噻螨威;TDE;虫酰肼;吡螨胺;tebupirimfos;氟苯脲;七氟菊酯;双硫磷;TEPP;环戊烯丙菊酯;特丁硫磷;四氯乙烷;杀虫畏;胺菊酯;胺菊酯[(1R)异构体];四氟醚菊酯;高效反式氯氰菊酯;0-氯氰菊酯;噻虫啉;噻虫嗪;硫色硫磷(thicrofos);氰乙肟威(thiocarboxime);杀虫环;杀虫环草酸氢盐;硫双威;久效威;甲基乙拌磷;杀虫酸(thiosultap);苏云金素;唑虫酰胺;四溴菊酯;四氟苯菊酯;反式氯菊酯;苯螨噻;唑蚜威;三唑磷;敌百虫;trichlormetaphos-3;毒壤膦;三氯丙磷(trifenofos);杀铃脲;混杀威;烯虫硫酯;蚜灭磷;酚氟虫腈(vaniliprole);XDE-105;灭除威;灭杀威;zeta-氯氰菊酯;zolaprofos;和ZXI 8901;化学名是3-乙酰基-5-氨基-142,6-二氯-4-(三氟甲基)苯基]-2-甲基亚磺酰基吡唑的化合物。
在本发明配制剂中,可以使用单独或与其它活性物质尤其是农药组合,用作农业活性物质的某些除草剂活性物质是:草芽畏;2,4-D;2,4-D-2-乙基己基;2,4-滴丁酸;2,4-滴丁酸-丁酯;2,4-滴丁酸二甲铵;2,4-滴丁酸-异辛酯;2,4-滴丁酸-钾盐;2,4-滴丁酸-钠盐;2,4-滴-丁氧基乙酯(2,4-滴-丁氧基乙酯(2,4-D丁氧基乙基酯));2,4-滴丁酯;2,4-滴-二甲铵盐;2,4-滴-二乙醇胺;2,4-滴-异辛酯;2,4D-异丙基;2,4-滴-钠盐;2,4-滴-三乙醇胺;乙草胺;三氟羧草醚;苯草醚;三氟羧草醚-钠盐;丙烯醛;AKH-7088;甲草胺;二丙烯草胺;禾草灭;禾草灭-钠盐;烯丙醇;alorac;ametridione;莠灭净;amibuzin;氨唑草酮;氨唑草酮;酰嘧磺隆;环丙嘧啶酸(aminocyclopyrachlor);氯氨吡啶酸(aminopyralid);氯氨吡啶酸(aminopyralid);甲基胺草磷;杀草强;氨基磺酸铵;莎稗磷;甲氧平草隆(anisuron);磺草灵;磺草灵-钠盐;atraton;莠去津;唑啶草酮;四唑嘧磺隆;四唑嘧磺隆;叠氮津(aziprotryne);燕麦灵;BCPC;氟丁酰草胺;草除灵;草除灵;bencarbazone;bencarbazone;乙丁氟灵;呋草黄;解草嗪;苄嘧磺隆;苄嘧磺隆-甲酯;地散磷;灭草松;灭草松-钠盐;吡草酮;毒苯安(benzadox);双苯嘧草酮;benzipram;双环磺草酮;吡草酮;benzofluor;新燕灵;苯噻隆;苯噻隆;bicyclopyrone;甲羧除草醚;双丙氨膦;双丙氨膦-钠盐;双草醚;双草醚-钠盐;硼砂;除草定;糠溴草腈(bromobonil);溴丁酰草胺;溴莠敏;溴酚肟;溴苯腈;溴苯腈-庚酸盐/酯;溴苯腈-辛酸盐/酯;溴苯腈-钾盐;丁草胺;氟丙嘧草酯;抑草磷;丁烯草胺;丁硫咪唑酮(buthidazole);丁磺隆(buthiuron);仲丁灵;丁苯草酮;炔草隆;丁草敌;二甲胂酸;唑草胺;氯酸钙;氰氨化钙;cambendichlor;威磺灵(carbasulam);威磺灵(carbasulam);双酰草胺;carboxazole;carboxazole;唑草酸(carfentrazone);唑草酯;CDEA;CEPC;甲氧除草醚;草灭畏;丁酰草胺;炔禾灵(chlorazifop);可乐津(chlorazine);氯溴隆;氯炔灵;乙氧隆(chloreturon);伐草克;燕麦酸(chlorfenprop);氟咪杀(chlorflurazole);整形醇;氯草敏;氯嘧磺隆;氯嘧磺隆-乙酯;氯乙酸;草枯醚;三氯丙酸(chloropon);绿麦隆;枯草隆;羟敌草腈(chloroxynil);chlorprocarb;氯苯胺灵;氯磺隆;氯酞酸;氯酞酸-二甲酯;氯硫酰草胺;吲哚酮草酯;环庚草醚;醚磺隆;咯草隆;烯草酮;cliodinate;炔草酸(clodinafop);氯醚氧丙酸(clofop);炔草酯;异噁草酮;氯甲酰草胺;氯甲酰草胺;调果酸;cloproxydim;二氯吡啶酸;二氯吡啶酸-乙醇胺;解草酸(cloquintocet);解草酯;氯酯磺草酸(cloransulam);氯酯磺草酸-甲酯;CMA;硫酸铜;CPA;CPA-二甲基铵;CPA-异辛基;CPA-乙硫酯;氯苯氧乙酸;4-CPB;CPMF;4-CPP;CPPC;醚草敏;甲酚;苄草隆;单氰胺;氰草净;氰草津;环草敌;环丙嘧磺隆;噻草酮;环莠隆;氰氟草酸(cyhalofop);氰氟草酯;
苯草快(cyperquat);环丙津;环茂安(cyprazole);环酰草胺;2,4-D;3,4-DA;杀草隆;茅草枯;茅草枯-钠盐;棉隆;甜菜安;2,4-滴丁酸;3,4-DB;2,4-DEB;异丁草胺;伐草磷;甜菜安;敌草净;燕麦敌;麦草畏;麦草畏-二甲基铵盐;麦草畏-钾盐;麦草畏-钠盐;麦草畏-三乙醇胺;敌草腈;dichloralurea;烯丙酰草胺;苄胺灵;2,4-滴丙酸;2,4-滴丙酸-丁氧基乙酯;2,4-滴丙酸-二甲基铵盐;2,4-滴丙酸-异辛酯;精2,4-滴丙酸;2,4-滴丙酸-钾盐;禾草灵(diclofop);禾草灵;双氯磺草胺;双氯磺草胺;二乙除草快(diethamquat);乙酰甲草胺;difenopenten;枯莠隆;野燕枯;野燕枯硫酸甲酯盐;吡氟酰草胺;吡氟酰草胺;氟吡草腙(BAS 65400H);噁唑隆;哌草丹;二甲草胺;异戊乙净;二甲吩草胺;精二甲酚草胺;噻节因;二甲基次胂酸;敌灭生;dimidazon;氨氟灵;dinofenate;硝丙酚(dinoprop);戊硝酚;地乐酚;特乐酚;特乐酯;特乐酚-铵盐;特乐酚-二乙醇胺;双苯酰草胺;异丙净;敌草快;二溴化敌草快;赛松;氟硫草定;敌草隆;DMPA;二硝酚;3,4-DP;DSMA;EBEP;甘草津(eglinazine);茵多酸;三唑磺;三唑磺;茵草敌;抑草蓬;戊草丹;乙丁烯氟灵;胺苯磺隆;胺苯磺隆-甲酯;磺噻隆;硫草敌;乙氧呋草黄;氟乳醚(ethoxyfen);乙氧磺隆;硝草酚(etinofen);etnipromid;etnipromid;etnipromid;乙氧苯草胺;EXD;fenasulam;fenasulam;fenasulam;解草唑-乙酯;解草啶;2,4,5-涕丙酸;噁唑禾草灵;精噁唑禾草灵;精噁唑禾草灵-乙酯;fenoxasulfone;fenteracol;噻唑禾草灵;噻唑禾草灵;四唑酰草胺;非草隆;非草隆-三氯乙酸;硫酸亚铁;麦草氟;高效麦草氟;精麦草氟-异丙酯;精麦草氟-甲酯;啶嘧磺隆;双氟磺草胺;双氟磺草胺;吡氟禾草灵;吡氟禾草灵-丁酯;精吡氟禾草灵;精吡氟禾草灵-丁酯;异丙吡草酯;氟唑磺隆;氟唑磺隆;氟吡磺隆;氯乙氟灵;氟噻草胺(BAS FOE 5043);flufenican;flufenican;氟哒嗪草酸(flufenpyr);唑嘧磺草胺;伏草噁(flumezin);氟烯草酸;氟烯草酸-戊酯;丙炔氟草胺;炔草胺;氟草隆;三氟硝草醚;乙羧氟草醚;乙羧氟草醚-乙酯;氟定咪(fluoromidine);氟除草醚;氟硫隆;氟胺草唑;氟胺草唑;flupropacil;四氟丙酸;四氟丙酸-钠盐;氟啶嘧磺隆(flupyrsulfuron);氟啶嘧磺隆-甲酯钠盐;解草胺;芴丁酯;芴丁酯-丁酯;氟啶草酮;氟咯草酮;氯氟吡氧乙酸;氯氟吡氧乙酸-2-丁氧基-1-甲基乙基;氯氟吡氧乙酸-甲酯;呋草酮;嗪草酸;嗪草酸甲酯;氟草肟;氟磺胺草醚;氟磺胺草醚-钠盐;甲酰氨基嘧磺隆;杀木膦;杀木膦-铵盐;解草噁唑;呋氧草醚;草甘膦;草铵膦酸(glufosinate);草铵膦;精草铵膦酸(glufosinate-P);草甘膦铵盐;草甘膦-异丙基铵盐;草甘膦钠盐;草甘膦-三甲基锍盐;halosafen;halosafen;氯吡嘧磺隆;氯吡嘧磺隆-甲酯;氟啶草;氟吡禾灵;高效氟吡禾灵;高效氟吡甲禾灵;氟吡乙禾灵;氟吡甲禾灵;六氯丙酮;六氟砷酸钾;环嗪酮;双丙氨膦;咪唑喹啉酸;咪草酸;甲氧咪草烟;甲咪唑烟酸;咪唑烟酸;咪唑烟酸-异丙基铵盐;咪唑喹啉酸;咪唑喹啉酸-铵盐;咪草酸-甲酯;咪唑乙烟酸;咪唑乙烟酸-铵盐;唑吡嘧磺隆;甲咪唑烟酸(AC 263,222);茚草酮;indaziflam;碳烯碘草腈(iodobonil);碘甲烷;碘磺隆(iodosulfuron);碘苯腈;辛酰碘苯腈;碘苯腈-钠盐;草怕津(ipazine);ipfencarbazone;ipfencarbazone;异草啶(iprymidam);丁咪酰胺;异草定;丁嗪草酮;异草完隆;isopolinate;异丙乐灵;异丙隆;异噁隆;异噁酰草胺;异噁氯草酮;异噁唑草酮;异噁草醚;特胺灵;乳氟禾草灵;碘苯腈辛酸盐/酯;碘苯腈-钠盐;环草定;利谷隆;MAA;MAMA;2甲4氯;2甲4氯-丁氧基乙酯;2甲4氯-二甲基铵盐;2甲4氯异辛酯;2甲4氯-钾盐;2甲4氯钠;2甲4氯乙硫酯;2甲4氯丁酸;2甲4氯丁酸乙酯;2甲4氯丁酸-钠盐;2甲4氯丙酸;精2甲4氯丙酸;甲基特乐酯(medinoterb);苯噻酰草胺;吡唑解草酯;氟磺酰草胺;甲氧扑灭津(mesoprazine);mesosulfuron;甲磺隆-甲酯;硝磺草酮;百亩酸(metam);噁唑酰草胺;噁唑酰草胺;苯嗪草酮;威百亩;吡唑草胺;methalpropalin;灭草唑;metazosulfuron;甲氟哒酮(metflurazon);甲基苯噻隆;methiobencarb;methiozolin;灭草恒(methiuron);醚草通(methometon);甲氧丙净;溴甲烷;异硫氰酸甲酯;甲基胂酸;甲基杀草隆;吡喃隆;溴谷隆;异丙甲草胺;磺草唑胺;甲氧隆;嗪草酮;甲磺隆;禾草敌;庚酰草胺;monisouron;monisouron;一氯乙酸;绿谷隆;灭草隆;伐草快;MPB-钠;甲基砷酸钠;敌草胺;萘草胺;抑草生钠;草不隆;烟嘧磺隆;壬酸;氟氯草胺;甲磺乐灵;除草醚;nitrofluorfen;氟草敏;草完隆;OCH;油酸(脂肪酸);坪草丹;邻-二氯苯;嘧苯胺磺隆(orthosulfamuron);氨磺乐灵;解草腈;丙炔噁草酮;oxapyrazon;环氧嘧磺隆;噁嗪草酮;噁草酮;乙氧氟草醚;对伏草隆(parafluron);百草枯;百草枯二氯化物;克草敌;二甲戊灵;五氟磺草胺;五氟磺草胺;五氯苯酚;月桂酸五氯苯酯;甲氯酰草胺;环戊噁草酮;石油;苯氟磺胺(perfluidone);pethoxamid;棉胺宁;甜菜宁;甜菜宁-乙酯;酰草隆;乙酸苯汞;氨氯吡啶酸;氨氯吡啶酸钾;氯吡酰草胺;氯吡酰草胺;唑啉草酯;哌草磷;亚砷酸钾;叠氮化钾;氰酸钾;丙草胺;氟嘧磺隆;氟嘧磺隆-甲酯;环腈津(procyazine);氨氟乐灵;氟唑草胺;环丙氟灵;环苯草酮;甘扑津;扑灭通;扑草净;毒草胺;敌稗;噁草酸;扑灭津;苯胺灵;异丙草胺;丙氧基缩二氨基脲;propyrisulfuron;炔苯酰草胺;甲硫基磺乐灵(prosulfalin);苄草丹;氟磺隆;吡草醚-乙酯;扑灭生(proxan);丙炔草胺;pydanon;pyraclonil;吡草醚(pyraflufen);氟苯唑草酮(pyrasulfotole);吡唑特;吡嘧磺隆;吡嘧磺隆;苄草唑;吡唑特;吡嘧磺隆-乙酯;苄草唑;嘧啶肟草醚;稗草丹;氯草定(pyriclor);pyridafol;哒草特;环酯草醚;嘧草醚;嘧草醚-甲酯;pyrimisulfan;嘧草硫醚(pyrithiobac);嘧草硫醚-钠盐;pyroxasulfone;pyroxasulfone;啶磺草胺;啶磺草胺;啶磺草胺;二氯喹啉酸;氯甲喹啉酸;灭藻醌;灭藻醌;quinonamid;喹禾灵;喹禾灵-乙酯;精喹禾灵;精喹禾灵-乙酯;喹禾糠酯;砜嘧磺隆;硫氰苯胺(rhodethanil);苯嘧磺草胺;苯嘧磺草胺;另丁津(sebuthylazine);仲丁通;烯禾啶;环草隆;西玛津;simeton;西草净;氯乙酸钠(SMA);精异丙甲草胺;亚砷酸钠;叠氮化钠;氯酸钠;氯乙酸钠;五氯苯酚钠;二甲次胂酸钠;磺草酮;菜草畏;甲磺草胺;甲嘧磺隆;甲嘧磺隆-甲酯;磺酰磺隆;硫酸;sulglycapin;灭草灵;焦油;三氯乙酸钠;牧草胺;丁噻隆;吡喃草酮;吡喃草酮(BAS620H);特草定;特草灵;特丁草胺;特丁通;特丁津;特丁净;tetrafluron;噻吩草胺;噻氟隆;噻唑烟酸;噻二唑草胺;噻苯隆;噻苯隆;thiencarbazone;噻吩磺隆;噻吩磺隆-甲酯;禾草丹;仲草丹;tioclorim;苯唑草酮(topramezone);苯唑草酮(topramezone);三甲苯草酮;野麦畏;醚苯磺隆;三嗪氟草胺;苯磺隆;苯磺隆-甲酯;苯磺隆-甲酯;杀草畏;三氯乙酸;三氯吡氧乙酸;三氯吡氧乙酸-丁氧基乙酯;三氯吡氧乙酸-三乙铵盐;灭草环;草达津;三氟啶磺隆(trifloxysulfuron);氟乐灵;氟胺磺隆;氟胺磺隆-甲酯;trifop;trifopsime;三羟基三嗪;三甲隆(trimeturon);茚草酰(tripropindan);草达克(tritac);三氟甲磺隆;2,4,5-涕;2,4,5-涕丁酸;草芽畏;三氯乙酸;牧草胺;丁噻隆;糠氧磺草酮(tefuryltrione);乙氧磺草酮(tembotrione);灭草敌:YRC 2388;和二甲苯草胺。
优选的农业活性物质是可商购的那些,并且需要使用这些树枝状化合物比如使得它们溶剂化或者使得可以较少施用即有效或者预防环境问题。这些包括但不限于草甘膦或氟乐灵。
式(I)的PEHAM树枝状聚合物能够用作:表面缀合的或表面结合的载体(比如可能自它们的椭圆、球、棒的形状变种,随机高支化的树枝状接枝物,核心-壳屋顶树枝状化合物),其能够通过存在的表面基团(TF)类型进一步修饰;用于时间释放式农业活性配制剂的包囊载体(无论农业活性物质是与内部(IF)结合还是简单包埋),其在树枝状聚合物结构中具有可裂解连接用于一旦施用的时间释放和pH或其它希望变化,在树枝状聚合物内部与其表面间的溶解度差异,因为代或形状的可能的农业活性物质量/PEHAM树枝状聚合物;和它们尺寸的精度使得可以用作分子尺寸标准、校准试剂,和用于穿透植物比如叶子或种子比如其包衣的成孔模板。
农业活性物质与这些PEHAM树枝状化合物的内部、表面结合或者与内部和表面均结合,并且基团可以是相同或不同的。如本文所用"与……结合"意指农业活性物质能够物理上包囊或包埋在树枝状化合物内部,部分或完全分散在树枝状化合物中,或者附着或连接至树枝状化合物或其任意组合,其中通过成共价键、成氢键、吸附、吸收、成进行键,成范德华力或离子键,或其任意组合进行附着或连接。农业活性物质和树枝状化合物的结合可以任选采用连接物和/或间隔物或螯合剂以使得便于制备或使用这些配制剂。适宜的连接基团是将靶向导向物(director)(也即T)连接至树枝状化合物(也即D)而不显著损害导向物有效性或者农业活性物质和在经合并的树枝状化合物中的农业活性物质有效性的基团。这些连接基团可以是可裂解的或不可裂解的并且一般地使用以避免在靶向导向物与树枝状化合物之间的立体位阻;优选所述连接基团是稳定的(也即非可裂解的),除非递送场所具有裂解所存在的连接体的能力(例如,酸可裂解的连接体,用于在细胞表面上或在核内体腔内释放)。由于这些树枝状化合物的尺寸、形状和官能团密度能够得到严格控制,存在农业活性物质能够与树枝状化合物结合的许多方式。例如,(a)在农业活性物质与一般是位于树枝状化合物表面或在其附近的官能团的物质之间,能够存在共价、库仑、疏水或螯合类结合;(b)在农业活性物质与位于树枝状化合物内部的部分之间,能够存在共价、库仑、疏水或螯合类结合;(c)能够制备树枝状化合物,其具有大部分中空的内部(也即,溶剂填充的空隙空间),这允许将农业活性物质物理捕集于内部(空隙体积),在此情况下农业活性物质的释放能够任选地通过将树枝状化合物表面充塞扩散控制部分来控制,(d)其中树枝状化合物具有内部官能团基团(IF),其还能够与农业活性物质结合,具有可裂解的(IF),其可以允许自树枝状化合物内部的受控(也即依赖pH)释出;或者(e)能够采用前述现象的各种组合。
本发明配制剂包含与至少一种农业活性物质结合的至少一种PEHAM树枝状化合物。这些组分均能具有多于一种类型;从而多于一种PEHAM树枝状化合物和多于一种农业活性物质能够存在于配制剂中。
配制剂常常具有至少一种农业上可接受的稀释剂或载体。使用何种农业上可接受的稀释剂或载体取决于最终用途或气候和/或土壤条件。相应于农业用途可接受的一般配制剂技术,这些稀释剂或载体中的某些是任意固体或液体添加剂,且能够配制为液剂、喷雾剂、油剂、乳剂、悬浮剂、颗粒剂、散剂、粉剂和其它常规配制剂。
还可以存在其它常规添加剂比如助剂,抗结剂;着色剂,增稠剂,表面活性剂,消泡化合物,清洁剂比如碱土金属盐,分散剂,碱化剂比如碱,成键试剂,乳化剂,氧化剂比如自由基捕获剂或过氧化氢类的催化性破坏剂,防腐剂,吸引剂和/或尤其是制备杀昆虫剂饵料的食品物质。这些添加剂可以以0至75%所述配制剂重量的量存在于根据本发明的配制剂。
另外,根据待处理疾病以及待防治、消灭或根除的昆虫和/或动物病虫害和/或杂草植物的需要、性质,这些病虫害的侵染水平,气候和/或土壤条件,根据本发明的配制剂可以含有一种或多种类型的农业活性物质,包括杀真菌剂和/或杀昆虫剂和/或杀螨剂和/或杀啮齿类剂和/或杀线虫剂和/或昆虫和/或动物病虫害驱避剂和/或调节植物和/或昆虫发展的试剂和/或一种或多种除草剂活性物质。
该配制剂用于处理植物或种子的方法中,使用上述配制剂,优选为了施用方便使用助剂和/或载体,用于改善农业活性物质对植物表面的粘着,改善农业活性物质对植物或种子的耐水牢度,保护农业活性物质免于使用配制剂导致的UV损害,保护植物或种子免于使用配制剂导致的UV损害,增加农业活性物质的土壤穿透或降低农业活性物质的土壤粘着使其能够到达植物根部或土壤下部分,或者降低植物或种子或土壤中的微生物对农业活性物质的酶促降解。这些方法使得可以降低农业活性物质向环境中的损失比如水流失,降低所需要的农业活性物质施用量同时保持农业活性物质的有效性,并且允许更佳的分散和降低配制剂的粘度从而更有效地使用农业活性物质。
不期望受理论所限,据信PEHAM树枝状化合物提供农业活性物质的增加的溶剂化,和/或降低粘度和/或通过各种方法更佳地分散,比如通过树枝状大分子吸收UV光子以降低农业活性物质的光降解,通过包囊更不可溶的农业活性物质而树枝状化合物表面在所希望环境中更高度可溶来增加溶解度,利用PEHAM树枝状化合物的表面化学,其能够穿透土壤、根、叶子和种子比如包衣以到达细胞或处理病虫害从而农业活性物质的淋洗流失得以减少。在树枝状化合物的表面基团修饰为(TF)或通过农业活性物质修饰的情况下,提供对叶子、种子表面和其它表面的粘着。
不期望受理论所限,据信式(I)的PEHAM树枝状化合物与农业活性物质结合或者充当增强配制剂所述特性的赋形剂。
设备和方法
体积排阻色谱法(SEC)
蒸发的SephadexTM(Pharmacia)纯化树枝状化合物的甲醇溶液,并用SEC实验所用的流动相重构(1mg/mL浓度)。对于SEC,全部样品新鲜制备并立即使用。
树枝状化合物通过SEC系统(Waters 1515)定量分析,其在等度模式操作,配有折光率检测器(Waters 2400和Waters 717Plus自动采样器)。在RT与两个串联TSK凝胶柱上(Supelco)进行分析,所述柱为G3000PW和G2500PW,颗粒尺寸10μm,30cm×7.5mm。乙酸缓冲剂流动相(0.5M)以1mL/min流速泵送。据观察树枝状化合物的洗脱体积是11-16mL,取决于树枝状化合物的代。
高压/高效液体色谱法(HPLC)
高压液体色谱法(HPLC)用Perkin ElmerTM系列200设备进行,其配有折光率和紫外光检测器和Waters(5μm)柱(4.6mm直径,150mm长度)。典型分离方案包括0.1%含水乙酸和乙腈(75:25%v/v)作为洗脱液,紫外光(λ=480nm)作为检测器。
薄层色谱法(TLC)
用薄层色谱法来监测化学反应进程。将一滴物质,一般是0.05M至0.4M有机溶剂中的溶液,加至硅胶板并置于溶剂室,让其进展一般10-15分钟。在已洗脱溶剂之后,一般将TLC板干燥,然后染色(如下描述)。因为硅胶是极性聚合物支持物,极性较低的分子在板上移动最远。"Rf"值用来确定物质在TLC板上的移动远近。改变溶剂条件将随后改变Rf值。该Rf通过产品移动长度与溶剂移动长度的比值来测量。
物质:所用TLC板是(1)"薄层色谱法板-硅胶玻璃背衬,尺寸20x 20cm,层厚:250μm;或者是(2)"薄层色谱法板塑料板-EM Science"氧化铝背衬,尺寸20x 20cm,层厚200μm。
染色条件:(1)茚三酮:用1.5g的茚三酮、5mL乙酸和500mL的95%乙醇制备溶液。将板浸没于茚三酮溶液中,用热气枪干燥和加热直至发生颜色变化(粉色或紫色斑点表示存在胺)。(2)碘室:将2-3g的I2置于封闭容器中。将TLC板置于该室中15分钟,产品斑点染为褐色。(3)KMnO4染色:用1.5g的KMnO4、10g的K2CO3、2.5mL的5%NaOH和150mL的水制备溶液。将TLC板浸没于KMnO4溶液中,产品斑点变黄。(4)UV检查:用紫外(UV)灯来照亮产品斑点。短波(254nm)和长波(365nm)均用于产品鉴定。
MALDI-TOF质谱
在配有Pulsed Ion Extraction的Bruker AutoflexTMLRFMALDI-TOF质谱上获得质谱图。在反射器模式中用19kV样品电压和20kV反射电压,获得低于20kDa的质量范围。聚环氧乙烷用于校准。在线性模式中用20kV样品电压获得较高的质量范围。较高质量范围用牛血清白蛋白校准。
一般地,样品这样制备:将1μL等分试样的5mg/mL分析物溶液与10μL基质溶液组合。除非另有指明,基质溶液是10mg/mL的2,5-二羟基苯甲酸,在3:7乙腈:水中。将等分试样(2μL)的样品/基质溶液点染于靶标板上,让其在RT空气干燥。
超滤分离(UF)
典型的超滤分离方案如下:将产品和不希望的化合物的混合物溶于适当体积的用于该混合物的溶剂(例如,125mL的MeOH),并在切向流UF装置上进行超滤,所述装置包括3K截断的再生纤维素膜,工作压力为20psi(137.9kPa),温度为25℃。在UF收集1500mL渗透物(~5小时)期间,在烧瓶中标注的渗余物体积保持在100-125mL。第一升渗透物在旋转式蒸发仪上反萃取挥发物,随后抽高真空提供纯化产品。取决于具体分离问题,膜的截断尺寸(例如3K、2K或1K)和渗透物和渗余物体积会变化。
SephadexTM分离
将产品溶于最小量的溶剂(水、PBS或MeOH),并经过SephadexTMLH-20(Pharmacia)在溶剂中纯化。在洗脱柱的空隙体积之后,以约2-20mL等分试样收集级分,取决于各自所涉及的分离。用上述的用适当溶剂的TLC来鉴定含有相似产品混合物的级分。组合相似级分,蒸发溶剂,提供固体产品。
核磁共振(NMR)-1H和13C
样品制备:
向50-100mg无水样品加入800-900μL的氘化溶剂使其溶解。使用典型参比标准即三甲基硅烷。典型的溶剂是CDCl3,CD3OD,D2O,DMSO-d6,和丙酮-d6。将溶解样品转移至NMR管,达到~5.5cm的管中高度。
设备:(1)在300MHz 2-通道VarianTMMercury Plus NMR光谱仪系统上获得300MHz NMR数据,其使用Automation Triple ResonanceBroadband(ATB)探针,H/X(其中X是从15N至31P可调)。SolarisTM9操作系统的在Sun BladeTM150计算机进行数据采集。所用软件是VNMRv6.1C。(2)在500MHz 3-通道VarianTMInova 500MHz NMR光谱仪系统获得500MHz NMR数据,其使用可转换探针,H/X(X是自15N至31P可调的)。在SolarisTM9操作系统的Sun BladeTM150计算机上进行数据采集。所用软件是VNMR v6.1C。
红外光谱测定法(IR或FTIR)
在Nicolet FourierTMTransform红外光谱仪,模型G系列Omnic,系统20DXB上获得红外光谱数据。用溴化钾板(Aldrich)处理纯样品。
紫外/可见光谱测定法(UV/Vis)
在Perkin ElmerTMLambda 2UV/VIS分光光度计上获得UV-VIS光谱数据,其采用各自样品的高吸收光波长例如480或320nm。
本发明通过下述实施例进一步阐明,其意在仅仅示范本发明。
实施例1:将季戊四醇四缩水甘油基醚1与三(2-氨基乙基)胺(TREN)2反应,产生伯胺表面
[(C)=PETGE;(IF1)=OH;(BR1)=TREN;(TF)=伯NH2;G=1]
向50-mL含有搅拌子的圆底烧瓶加入TREN 2(16.0g,109mmol,10当量/环氧化物)和4mL的MeOH,冷却至~25℃。向该搅拌混合物滴加PETGE 1(1.0g,2.78mmol,11.1mmol环氧化物)的2mL MeOH溶液。在25℃在N2气氛下,将该混合物搅拌24小时。挥发性物质通过旋转式蒸发进行蒸馏,提供粗制残余物,用Kugelrohr设备在200-230℃在高真空下将其瓶-对-瓶蒸馏,提供2.4g残余物。该物质的MALDI-TOF质谱显示在967amu[M+Na]+质量的所希望4:1加合物的清楚光谱,和于799amu[M+Na]+的3:1加合物的较小信号。TLC(50%NH4OH,MeOH中)显示不存在TREN。13C NMR光谱显示纯净产品3的期望峰(2.4g,92%收率)。其谱图如下:
13C NMR:(125MHz,CDCl3)δ39.63,35.36,47.30,52.64,54.01,57.24,68.10,70.33,74.64;和
MALDI-TOF MS:C42H101N16O8;计算944.3,实测967[M+Na]+amu。
下述方案1说明该反应。
方案1
实施例2:用二羟基氨基支化单元试剂开环:羟基封端的PEHAM树枝状化合物(G=1),来自三羟甲基丙烷三缩水甘油基醚和二乙醇胺[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=DEA;(TF)=OH;G=1]
将DEA 5(7.82g,74.47mmol)(Aldrich)和120mL的无水MeOH(Aldrich),均不加进一步纯化地置于炉干的250-mL单颈圆底烧瓶。该烧瓶配有搅拌子和隔膜。将TMPTGE 4(5g,16.55mmol)溶于40mL的无水MeOH,在1小时期间内于RT通过压力平衡漏斗滴加至上述搅拌中的溶液。将漏斗用回流冷凝器替换,在N2气氛下在60℃加热60小时。用旋转式蒸发仪减压除去溶剂,提供无色透明的液体。将全部反应混合物转移至100-mL单颈圆底烧瓶。在180-190℃,通过Kugelrohr蒸馏减压分离过量DEA 5。回收产品,6(9.76g;95.53%收率),是透明的粘稠液体。其谱图如下:
1H NMR:(300MHz,CD3OD):δ0.87(t,J=7.50Hz,3H,CH3),1.43(q,CH2,J=7.20Hz,2H),2.52-2.79(m,18H),3.32(s,3H,3xOH),3.50(s,6H),3.40(d,J=5.10Hz,6H),3.54-3.67(m,12H),3.93(六重,J=5.10Hz,3H),4.85(s,6H,6x OH);和
13C NMR:(75MHz,CD3OD):δ6.93,22.76,43.43,57.42,58.51,59.47,68.32,71.56,73.72;和
IR(纯):λmax 3354,2939,2817,1454,1408,1367,1321,1280,1111,1081,1070,871,778cm-1;和
MALDI-TOF MS:C27H59N3O12计算617;实测641(M+Na)amu。
下述方案2说明该反应:
方案2
实施例3:将季戊四醇四缩水甘油基醚与亚氨基二乙酸二乙酯反应(DEIDA)
[(C)=PETGE;(IF1)=OH;(BR1)=DEIDA;(TF)=乙基酯;
G=1.5]
在30分钟期间内,通过加液漏斗,向DEIDA,7(5.67g,30mmol)(Aldrich)的35mL的EtOH(Aldrich)溶液逐滴加入PETGE,1(1.8g,5mmol,20环氧mmol)的20mL的EtOH(Aldrich)溶液。烧瓶配备回流冷凝器、N2气体入口,并置于预先加热的60℃油浴中。在加热1天之后,MALDI-TOF MS分析显示完美结构和三取代产品的计算质量。继续加热36小时,然后在旋转式蒸发仪上除去溶剂,提供浅褐色液体。在175℃,通过Kugelrohr蒸馏设备将过量DEIDA蒸除,提供粘稠液体,其确认为所希望的产品,8(4.99g,89.4%)。其谱图如下:
1H NMR(300MHz,CD3OD):δ1.24-1.29(24H,t,J=7.20Hz),3.03-3.09(4H,dd,J=3.60Hz),2.78-2.85(4H,bt,J=9.0Hz),3.41(12H,s),3.45(8H,s),3.61(8H,d,J=5.40Hz),4.14-4.21(16H,q,J=6.60Hz),4.61-4.67(4H,六重,J=4.20Hz);和
13C NMR(75MHz,CD3OD):δ13.41,13.45,45.89,49.79,53.65,55.77,56.21,57.97,60.57,60.69,68.71,69.79,69.93,71.31,73.55,78.43,78.46,168.62,170.26,172.30;和
IR(纯):νmax3457,2980,2934,2904,2868,1741,1675,1460,1378,1250,1198,1163,1106,1065,1029,927,860,819,732cm-1;和
MALDI-TOF MS:C49H88N4O24计算1117.2;实测1117.7[M]+,1139.7[M+Na]+amu。
下述方案3说明该反应。
方案3
实施例4:来自伯胺的酯衍生物
A.自季戊四醇和表氯醇(EPI)合成季戊四醇四缩水甘油基醚[(C)=PETGE;(TF)=环氧]
该过程根据Mitsuo等人,Synthesis,487(1993)进行。将季戊四醇9(13.6g,400mmol)和100mL DMSO加入1-L 3-颈圆底烧瓶,然后一次将KOH(52.7g,800mmol,2当量/OH)全部加入。用机械搅拌器激烈地搅拌反应混合物,用冰浴冷却至15-20℃。在150分钟期间内,在压力平衡漏斗中滴加EPI 10(110.4g或93.55mL,1.2mol,3当量/OH)。在加入EPI 10期间,将温度保持在15-20℃。反应混合物的颜色从无色变为淡黄色。在完成加入之后,将反应混合物温热至RT,继续搅拌过夜。通过TLC监测反应进程。在3小时之后,TLC指出PETGE 1和季戊四醇三缩水甘油基醚11的斑点。通过继续反应,三缩水甘油基醚11期望转化为产品1;然而,观察到1的某些二聚体化,其提供产品12。
反应混合物过滤通过布氏漏斗,固体用100mL的DCM洗涤。在旋转式蒸发仪上除去挥发性级分DCM。将粗制反应混合物用饱和盐水(2x 100mL)处理,用二乙醚(2x 100mL)萃取。经合并的醚层在Na2SO4上干燥,在旋转式蒸发仪上浓缩,提供深黄色/浅褐色液体。将粗制品划分为两个相等部分,使其经受硅胶上的柱色谱法。将硅胶(300g)加载至柱上(25cm高度x 5.5cm宽度)。在洗脱500mL的溶剂之后,收集40mL级分。第一级分是EPI 10,随后是PETGE 1(Rf=0.62),然后是二聚体12(Rf=0.44),和最终是三缩水甘油基醚11(Rf=0.33)。分离的纯的PETGE 1收率是45-60%(一些量被其它副产品污染)。光谱分析符合1的报告数据,而对产品11 & 12的分析也令人满意。
下述方案4说明该反应。
方案4
B.保护二亚乙基三胺的伯胺,用仲胺封盖四官能环氧化物:两种伯胺
[(C)=PETGE;(IF1)=OH;(BR1)=DIA;(TF)=伯NH2;G=1]
在氩气氛下,将DETA 13(6.56g,63.6mmol)(Acros)和125mL的4-甲基-2-戊酮14(Aldrich)加入250-mL圆底烧瓶,配有Dean-Stark捕集器,加热至140℃。在恒沸蒸出理论量水(2.2mL)之后,将反应冷却至RT。混合物的重量是77.37g,含有63.6mmol仲胺15。将混合物(12.16g)转移至50-mL圆底烧瓶。通过旋转式蒸发除去溶剂,提供油状物。向该油状物加入PETGE 1(360mg,1.0mmol)(实施例4A制得)的5.5mL的无水MeOH溶液。将反应加热至75℃,持续23小时。除去溶剂,提供16,将25mL的2-丙醇和3.0mL的水加入残余物。将混合物加热至50℃持续2小时。用旋转式蒸发仪除去溶剂。通过Kugelrohr蒸馏(150℃)除去过量DETA 13,提供产品17,是稍带黄色的粘性油状物,其具有下述谱图:
MALDI-TOF:计算773;实测795.784(M+Na)amu。
下述方案5说明该反应:
方案5
C.[(C)=PETGE;(IF1)=OH;(BR1)=DETA;(BR2)原位=甲基丙烯酸盐/酯;(TF)=甲基酯;G=2.5]
在0℃,将八胺17(实施例4B制得)的MeOH溶液逐滴加入丙烯酸甲酯18(Acros)的MeOH溶液(1.5当量/NH)。在加入之后,让反应温热至RT。然后,将混合物加热至40℃持续24小时。然后,除去溶剂提供产品19,是黄色油状物,具有下述谱图:
MALDI-TOF:计算2146;实测2169.662(M+Na)amu。
方案6说明该反应:
方案6
实施例5:用预先形成的三(羟基甲胺)(TRIS)支化单元试剂开环:九-羟基表面树枝状化合物,G=1,来自TMPTGE和TRIS[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=TRIS;(TF)=OH;G=1]
将TMPTGE 4(2.66g,8.8mmol)和50mL的MeOH加入炉干的100-mL圆底烧瓶。烧瓶配有搅拌子和塞子。在RT,将TRIS 20(4.79g,39.6mmol)(Fisher Scientific)一批加入上述搅拌中的反应混合物。烧瓶配有回流冷凝器,在60℃在N2气氛下加热60小时。在加热约15分钟之后,TRIS 20完全溶解。将反应混合物冷却至RT,转移至500-mLErlenmeyer烧瓶。然后加入第一120mL的氯仿,随后在用药刀稳定搅拌下缓慢加入300mL的己烷。在己烷加入期间,观察到形成白色沉淀。再次彻底混合混合物,让其在RT静置过夜。观察到烧瓶壁上和底部的沉淀,是片状固体。温和地混合溶液,将固体自玻璃分开,随后经过布氏漏斗过滤混合物,提供所希望的产品21(1.7g)。在烧瓶底部余留无色糊状物,即使在分开固体之后。该糊状物重5.2g,(1H和13C NMR的信号显示树枝状化合物21,以及痕量量的TRIS 20)。将糊状物溶于5mL的MeOH,随后用MeOH(2x 2mL)冲洗烧瓶。将甲醇溶液加载至SephadexTMLH-20柱。在洗脱600mL的MeOH之后,收集15mL等分试样的级分。所希望的树枝状化合物21存在于级分18-47中;另外,TRIS20存在于级分48-58中。合并级分18-47,在旋转式蒸发仪减压蒸发溶剂,提供吸湿性固体(4.2g;71.82%),(G=1)PEHAM树枝状化合物21。自48-58蒸发溶剂,提供TRIS 20(0.592g),是无色固体。其谱图如下:
1H NMR:(300MHz,CD3OD):δ0.86(t,J=7.20Hz,3H),1.42(q,J=6.90Hz,2H),2.64(dd,J=7.80&8.10Hz,3H),2.78(dd,J=3.60& 3.60Hz,3H),3.34(s,6H),3.35(s,6H),3.41(d,5.10Hz,6H),3.48(s,1H,OH),3.50(s,1H,OH),3.53(d,J=3.00Hz,12H),3.58(s,1H,OH),3.67(bt,J=3.00Hz3H,3x NH),3.79(六重,J=3.60Hz,3H),4.81(s,9H,9x OH);和
13C NMR:(75MHz,CD3OD):δ6.91,22.72,43.41,44.34,59.83,61.49,70.07,71.57,74.27;和
IR(纯):vmax 3354,2919,2873,1460,1424,1408,1367,1296,1234,1106,1029,866,773cm-1;和
MALDI-TOF MS:C27H59N3O15计算665;实测689(M+Na)amu。
下述方案7说明该反应:
方案7
实施例6:将季戊四醇四缩水甘油基醚(PETGE)与三(羟基甲基)氨基甲烷(TRIS)反应
[(C)=PETGE;(IF1)=OH;(BR1)=TRIS;(TF)=OH;G=1]
在250-mL圆底烧瓶中,在机械搅拌下,将PETGE 1(3.16g,8.78mmol)溶于70mL的MeOH。将溶液置于60℃油浴中,经由粉末漏斗加入TRIS 20(6.41g,52.8mmol,1.50当量/环氧化物)(Fisher Scientific)。然后,将烧瓶配备回流冷凝器,让其反应48小时。通过TLC(3:1CH2Cl2:MeOH)监测反应,在此时间之后未观察到PETGE 1(Rf=0.80)。将混合物用120mL的氯仿稀释,然后在搅拌下缓慢加入300mL的己烷。形成白色沉淀,让混合物静置16小时。将溶液过滤通过布氏漏斗,在烧瓶底部产生透明、白色糊状物。在真空下干燥糊状物,产生6.98g的粗制产品22。将产品重新溶于40mL的MeOH和60mL的氯仿,通过结晶自300mL的己烷分离剩余的TRIS 20。过滤混合物,剩余的半固体在高真空下干燥24小时,产生5.35g产品22(72.0%收率,7.43g理论质量)。为了进一步纯化,将该物质加载于36"x 4"(91cm x 10cm)LH-20SephadexTM柱。在收集575mL空隙体积之后,收集48个各12mL MeOH的级分,通过TLC(7:3MeOH:NH4OH)分析。回收2.29g纯化产品22(31%收率)。其谱图如下:
1H NMR(500MHz,D2O):δ2.644(1H,q,J=4.88Hz),2.76(1H,q,J=3.625),3.34(2H,s)3.44(2H,d,J=9.0Hz),3.54(2H,q,J=6.75Hz),3.79(1H,s),4.80(4H,s);和
13C NMR(75MHz,D2O):δ45.43,46.91,49.85,61.01,62.69,71.14,75.43,79.42;和
MALDI-TOF:C33H72N4O20计算845;实测867[M+Na]+amu。
下述方案8说明该反应。
方案8
实施例7:
A.将季戊四醇三烯丙基醚(PETriAE)与间-氯过氧苯甲酸(间-CPBA)反应
[(C)=PETriGE;(FF)=OH;(TF)=环氧化物]
向100-mL圆底烧瓶加入PETriAE 23(2.56g,10.0mmol,30烯烃mmol)(Aldrich)和50mL氯仿(Fisher Scientific)。在机械搅拌下,在RT分批向该溶液加入间-CPBA 24(8.84g,36.0mmol)(Acros Organics)。将混合物搅拌3天,然后首先用3%焦亚硫酸钠(Na2S2O5)水溶液(3x 100mL)(Aldrich),随后3%碳酸氢钠(NaHCO3)水溶液(3x 100mL)洗涤。有机层在硫酸钠上干燥,通过旋转式蒸发浓缩,提供淡黄色的液体25(2.58g,84.8%收率)。其谱图如下:
1H NMR(300MHz,CDCl3):δ2.57(q,J=2.70Hz,3H),2.76(t,J=4.50Hz,4H),3.07-3.12(m,3H),3.33(dd,J=1.50&1.20Hz,2H),3.37(dd,J=1.50 & 1.20Hz,2H),3.51(q,J=9.00Hz,6H),3.66(s,H),3.69(d,J=2.70Hz,2H),3.73(d,J=2.40Hz,2H);和
13C NMR(75MHz,CDCl3):δ44.34,45.51,50.97,65.33,71.61,71.67,71.73,72.18,72.20,72.23;和
IR(纯):3507,3056,2999,2922,2870,1476,1450,1424,1336,1248,1160,1098,1051,953,901,855,834,751cm-1;和
MALDI-TOF MS:C14H24O7;计算304.3;实测327.05[M+Na]+amu。
下述方案9说明该反应。
方案9
B.将季戊四醇三缩水甘油基醚(PETriGE)与炔丙基溴反应
[(C)=季戊四醇三缩水甘油基醚(PETriGE);(FF)=炔;(TF)=环氧化物]
向250-mL炉干圆底烧瓶加入PETriGE产品25(实施例7A制得)和120mL无水DMF(Aldrich)。将反应烧瓶用N2气体冲洗,用隔膜封闭,用冰浴冷却至0℃。在机械搅拌下,在20分钟期间内分批向该溶液加入氢化钠(1.35g,33.8mmol,60%矿物油分散液)(Aldrich)。在0℃额外搅拌40分钟之后,加入炔丙基溴26(3.73mL,90%重量%,甲苯中)。继续冷却90分钟,然后让混合物逐渐温热至RT。在该温度搅拌混合物过夜。然后,将反应混合物用冰浴冷却至10℃,用70mL水稀释,用乙酸乙酯(3x 70mL)萃取,用饱和盐水溶液(2x 50mL)洗涤。经合并的提取物在硫酸钠上干燥,通过旋转式蒸发浓缩,提供深褐色液体,将其通过柱色谱法在硅胶上纯化,最初用乙酸乙酯/己烷(20:80%v/v)洗脱,其逐渐变为乙酸乙酯/己烷(40:60%v/v)。合并在Rf=0.31提供TLC(乙酸乙酯:己烷1:1)斑的级分,发现其是纯的炔丙基化季戊四醇三缩水甘油基醚27(3.79g,82%收率)。其谱图如下:
1H NMR(300MHz,CDCl3):δ2.43(t,J=2.10Hz,1H),2.61(q,J=2.70Hz,3H),2.79(t,J=4.20Hz,3H),3.13(六重,J=3.00Hz,3H),3.37(d,J=6.00Hz,1H),3.41(d,J=5.70Hz,1H),3.51(d,J=3.90Hz,6H),3.54(s,2H),3.70(d,J=3.00Hz,2H),3.74(d,J=2.70Hz,2H),4.13(dd,J=2.10 & 0.30Hz,2H);和
13C NMR(75MHz,CDCl3):δ44.44,45.69,51.06,58.84,69.05,70.15,72.24,74.34,80.25;和
IR(纯):3267,3057,2991,2924,2878,2755,1480,1434,1367,1337,1260,1168,1096,1014,963,906,840,758,666cm-1。
下述方案10说明该反应。
方案10
C:自季戊四醇用烯丙基溴和间-氯过氧基苯甲酸(间-CPBA)合成季戊四醇四缩水甘油基醚
[(C)=PETGE;(TF)=环氧]
在1-L圆底烧瓶中,将季戊四醇9(15.03g,110mmol)(AcrosOrganics)和250mL的THF混合。经由粉末漏斗加入KOH(85.93g 1.35mol 3.0当量/OH),和溴化四丁基铵(TBAB)(0.460g,1.23% mol)(AcrosOrganics),随后经由125-mL加液漏斗在10分钟内加入烯丙基溴28(106.6g,1.35mol,3.0当量/OH)。然后,立即将反应置于70℃的油浴中,持续24小时。通过TLC(10:1己烷:乙酸乙酯)监测反应,显示Rf=0.4的产品斑点,而对三、二或一烯丙基取代的季戊四醇则无斑点。将反应混合物通过150-mL粗多孔玻璃的布氏漏斗真空过滤。有机层用二乙醚(2x 250mL)稀释。有机层用5% K2CO3(5x 300mL)洗涤,在MgSO4上干燥。通过旋转式蒸发仪除去挥发物(40℃浴温),产生季戊四醇四烯丙基醚29(PETAE)(30.07g;92%收率);其具有下述谱图:
IR(纯):vmax 3080,2867,1646,1478,1422,1350,1264,1137,992,922cm-1;和
13C NMR:(75MHz,CDCL3):δ45.33,69.25,72.15,115.95,135.16;和
1H NMR:(300MHz,CDCL3):δ3.39(4H,s),3.84(4H,q,J=2.3Hz),5.04(2H,q,J=13.8Hz),5.80(1H,七重,J=7.78Hz)。
将PETAE 29(3.29g,11.0mmol)和50mL的氯仿加入配有磁力搅拌子的500-mL圆底烧瓶。然后,在10分钟内经由加液漏斗加入间-CPBA24(70%)(12.51g,51.0mmol,1.14当量每烯烃)(Acros Organics)。反应烧瓶在过氧酸加入的30分钟内变得温热。在22℃搅拌反应72小时,然后用100mL DCM稀释,转移至500-mL分液漏斗。有机层用3%Na2S2O5(3x150mL)和3%NaHCO3(3x150mL)洗涤。有机层用Na2SO4干燥,过滤,通过旋转式蒸发仪(40℃浴温)除去挥发性物质。二氧化硅上的TLC(7:3甲苯:丙酮)显示Rf=0.48的一个斑点。在高真空下进一步干燥产品过夜产生PETGE 1,是透明无色粘稠液体(3.86g;92%收率);和具有下述谱图:
IR(纯):vmax 3055,2997,2876,1724,1480,1340,1258,1163,1018,908,845,799,760cm-1;和
13C NMR(75MHz,CDCl3):δ43.96,45.5450.62,69.80,71.90;和
1H NMR:(300MHz,CDCl3):δ2.55(1H,q,J=2.05Hz),2.72(1H,t,J=2.33Hz),3.09(1H,q,J=3.06Hz)3.32(1H,q,J=4.43Hz),3.45(2H,d,J=1.65Hz),3.64(1H,q,J=3.675Hz);和
MALDI-TOF:383[M+Na]+amu。
这些反应示于方案11。
方案11
D.将PETGE与叠氮化钠反应;修饰的核心
[(C)=季戊四醇四叠氮化物(PETAZ);(IF)=OH;(TF)=叠氮化物]
向50-mL圆底烧瓶加入PETGE 1(3.6g,10mmol)(实施例7C制得),27mL DMF和3mL水。向该溶液加入叠氮化钠(7.8g,120mmol,3当量/环氧化物),随后氯化铵(6.36g,3当量)。反应烧瓶配有搅拌子和回流冷凝器,在50℃加热过夜。通过TLC监测反应进程。在该时间之后,让反应混合物冷却至RT,然后经过布氏漏斗滤出固体物质,固体用乙酸乙酯(1x 50mL)洗涤。滤液用70mL水稀释,用乙酸乙酯(3x 50mL)萃取。经合并的有机层用饱和盐水洗涤,在硫酸钠上干燥,过滤通过硅胶床。通过旋转式蒸发浓缩滤液,提供无色液体30(5.1g,95%收率)。其谱图如下。
1H NMR(300MHz,CDCl3):δ3.04(bs,4H,OH),3.33(t,J=5.70Hz,8H),3.47(s,8H),3.49(t,J=2.40Hz,8H),3.93(五重峰,J=5.10Hz,4H);和
13C NMR(75MHz,CDCl3):δ45.75,53.52,69.68,71.09,73.12;和
MALDI-TOF MS:C17H32N12O8;计算532.5,实测555.3[M+Na]+amu。
下述方案12说明该反应。
方案12
E.将炔丙基季戊四醇三缩水甘油基醚与季戊四醇四叠氮化物(PETAZ)反应,产生PEHAM树枝状化合物G=1,其具有四臂核心和环氧化物表面
[(C)=PETGE;(IF1)=OH;(EX1)=三唑;(BR1)=PETriGE;(TF)=环氧化物;G=1]
向炉干50-mL圆底烧瓶加入炔丙基季戊四醇三缩水甘油基醚27(0.39g,1.14mmol,1.05当量/N3;从实施例7B制得),季戊四醇四叠氮化物30(0.144g,0.271mmol;从实施例7D制得),1.2g的叔丁醇和1.2g的水。烧瓶配有搅拌子,用塞子密封。向该混合物加入抗坏血酸钠(0.026g,0.114mmol,0.10当量),随后五水硫酸铜(II)(CuSO4.5H2O)(0.014g,0.057mmol,0.05当量)。通过TLC监测反应进程。在RT搅拌3天之后,发现反应完成。产品31不加分离地用于实施例7F中的后续反应,原因是环氧化物基团的高反应性。
下述方案13说明该反应。
方案13
F.将实施例7E的产品与二乙醇胺(DEA)反应,产生PEHAM树枝状化合物G=2,其具有四臂核心和羟基表面
[(C)=PETGE;(IF1)=OH;(EX1)=三唑;(BR1)=PETriGE;(IF2)=OH;(BR2)=DEA;(TF)=OH;G=2]
粗制产品31用DEA 5(1.07g,10.26mmol,3当量/环氧化物)(Aldrich)的3mL的叔丁醇溶液淬灭。在RT搅拌反应混合物1天,然后在45℃加热3天。冷却至RT之后,反应混合物用300mL的MeOH稀释,滤出一些不溶于的无机固体。滤液进一步通过UF经由1K体积排阻膜纯化。在收集900mL的渗透物之后,从UF抽取渗余物,UF用MeOH(3x 50mL)洗涤。旋转式蒸发除去溶剂,提供小麦色液体,在高真空下干燥提供所希望的G=2树枝状化合物32,是沫状固体(850mg,99%收率)。其谱图如下:
1H NMR(300MHz,CD3OD):δ2.49-2.80(m,H),3.40-3.50(m,H),3.52-3.70(m,H),3.81(bs,H),4.10-4.20(m,H),4.38-4.50(m,H),4.588(bs,H),7.99(s,4H);和
13C NMR(75MHz,CD3OD):δ29.99,45.51,45.68,53.39,57.47,58.46,59.63,64.32,68.44,69.03,69.35,70.12,72.85,73.84,125.04,144.82。
下述方案14说明该反应。
方案14
实施例8:
A.用二酯氨基支化单元试剂前体开环:酯封端的PEHAM树枝状化合物,G=1,来自三羟甲基丙烷三缩水甘油基醚(TMPTGE)和亚氨基二乙酸二乙酯(DEIDA)
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=DEIDA;(TF)=乙基酯;G=1.5]
将DEIDA 7(14.07g,74.47mmol)(Aldrich)和120mL的无水MeOH加入炉干的250-mL单颈圆底烧瓶。烧瓶配有搅拌子和隔膜。将TMPTGE 4(5.0g,16.55mmol)(Aldrich)溶于40mL的无水MeOH,然后在RT通过压力平衡漏斗逐滴在1小时期间内加入上述搅拌溶液。漏斗用回流冷凝器替换,在60℃在N2气氛下加热烧瓶60小时。在旋转式蒸发仪上减压除去溶剂,提供无色透明的液体。将全部反应混合物转移至100-mL单颈圆底烧瓶。在150-160℃,通过Kugelrohr蒸馏减压除去过量DEIDA 7。回收未蒸出的产品33(12.59g;87.5%收率),是淡黄色粘稠液体。在0℃,在乙醇中储存化合物33。其谱图如下:
1H NMR:(300MHz,CD3OD):δ4.65(六重,J=4.20Hz,3H),4.16(m,12H),3.59(s,12H),3.36(s,6H),3.30(s,6H),3.05(dd,J=3.60Hz,3H),2.95(dd,J=3.90Hz,2H),2.81(dt,J=1.80Hz & 9.90Hz,3H),2.67(dd,J=8.40 & 8.10Hz,2H),1.37(q,J=7.50Hz,2H),1.26(t,J=7.20Hz,6H,2x CH3),1.25(J=7.20Hz,12H,6x CH3),0.85(t,J=7.50Hz,3H,CH3);和
13C NMR:(75MHz,CD3OD):δ6.81,13.36,13.40,22.66,43.48,49.85,53.62,55.76,56.21,58.00,60.55,60.68,68.72,71.17,71.33,71.50,73.40,78.43,78.48,168.67,170.25,172.31;和
IR(纯):λmax 2980,2934,2904,2868,1741,1460,1408,1378,1342,1250,1198,1111,1065,1024,983,927,860,784cm-1;和
MALDI-TOF MS:C39H71N3O18计算869;实测893(M+Na)和847,801,779,775amu。(质谱显示消除OC2H5基团的典型碎裂方式。)
下述方案15说明该反应:
方案15
B.将来自与亚氨基二乙酸二乙酯(DEIDA)和三羟甲基丙烷三缩水甘油基醚反应的产品与三(2-氨基乙基)胺(TREN)反应,产生PEHAM树枝状化合物G=2,其具有三臂核心和伯胺表面
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=DEIDA;(BR2)=TREN;(TF)=伯NH2;G=2]
向100-mL圆底烧瓶加入TREN 2(17.05g,116.82mmol,60NH2当量/酯)和40mL的MeOH(Fisher Scientific)和磁力搅拌子。在放热混合反应停止之后(20分钟),在RT在1小时期间内滴加G=1酯33(0.846g,0.97mmol,5.84酯mmol;从实施例8A制得)的10mL的MeOH溶液。然后,将混合物置于油浴,在50℃加热3天。通过IR光谱监测反应进程,也即酯振动于1740cm-1消失,于1567cm-1出现酰胺振动。MALDI-TOF MS分析指出于1348[M+Na]+和1201[M+Na]+(1和2环)的伴随环路化合物(looped compounds)的所希望的G=2.0产品34的质量。反应混合物用700mL的MeOH稀释,并用1K体积排阻膜进行UF。在收集1.8升渗透物之后,自UF抽取渗余物,通过旋转式蒸发除去溶剂,提供淡黄色粘稠液体,将其进一步在高真空下干燥,提供所希望的G=2树枝状化合物34(1.41g,98.94%收率)。其谱图如下:
1H NMR(300MHz,CD3OD):δ0.86(3H,bt),1.38(2H,bs),2.32-2.60(H,m),2.67-2.76(H,m),3.29-3.34(H,m),3.82(3H,bs);和
13C NMR(125MHz,CD3OD):δ8.14,24.06,38.57,38.63,39.98,40.16,44.59,54.00,55.09,55.28,57.21,58.02,60.19,63.05,63.28,69.38,69.94,72.52,72.96,75.00,173.76,173.86,174.03;和
IR(纯):νmax 3298,2934,2842,1659,1572,1536,1470,1388,1357,1311,1116,973,819cm-1;和
MALDI-TOF MS:C63H143N27O12计算1470.9843;实测1494.2270[M+Na]+,1348.022[M+Na]+(1环路),1201.0970[M+Na]+(2环路)amu。下述方案16说明该反应。
方案16
实施例9:将得自季戊四醇四缩水甘油基醚和亚氨基二乙酸二乙酯(DEIDA)反应的产品与三(2-氨基乙基)胺(TREN)反应,产生PEHAM树枝状化合物G=2,其具有四臂核心和伯胺表面,用于DNA紧缩和抗菌活性
[(C)=PETGE;(IF1)=OH;(BR1)=DEIDA;(BR2)=TREN;(TF)=伯NH2;G=2]
向250-mL圆底烧瓶加入TREN 2(52.26g,358.0mmol,120NH2当量每酯),50mL的MeOH(Fisher Scientific)和搅拌子。在放热混合反应停止之后(30分钟),在RT在1小时期间内滴加G=1酯8(1.25g,1.12mmol,8.95酯mmol;从实施例3制得)的10mL的MeOH溶液,搅拌混合物过夜。MALDI-TOF MS分析显示所希望产品的期望的质量峰以及具有1和2环的副产物的质量峰。记录IR光谱,显示存在于1575cm-1的酰胺振动,不存在于1740cm-1的酯振动。继续搅拌额外36小时。然后,将反应混合物稀释至5%w/w MeOH溶液,用1K体积排阻膜进行UF。在收集3.5升渗透物之后,自UF抽取渗余物,旋转式蒸发除去溶剂,剩余的产品在高真空下干燥提供淡黄色沫状固体35(2.02g,94%收率)。其谱图如下:
1H NMR(500MHz,CD3OD):δ2.49-2.59(H,m),2.62(H,bt),2.66(H,s),2.68(H,s),2.69(H,s),2.70(H,s),2.73-2.82(H,m),3.29-3.47(H,m),3.82(H,bs);和
13C NMR(125MHz,CD3OD):δ38.64,40.19,48.48,49.85,53.94,55.10,55.29,57.66,58.10,60.23,63.06,69.33,71.41,75.11,173.70,173.80,173.97;和
IR(纯):νmax 3313,3078,2934,2868,1649,1557,1541,1475,1449,1362,1306,1163,1101,978,818cm-1;和
MALDI-TOF MS:C81H184N36O16;计算1918.6,实测1941.8[M+Na]+amu。
下述方案17说明该反应。
方案17
实施例10:将来自三羟甲基丙烷缩水甘油基醚(TMPTGE)的产品与亚胺基二乙酸二钠盐(IDADS)反应
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=IDA;(TF)=CO2Na;G=1]
在1000mL玻璃圆底烧瓶中,将39g的NaOH(片状)溶于100mL的H2O。向搅拌中的溶液加入IDADS 36(91.5g,0.69mol),激烈搅拌直至完全溶解。在20分钟期间内缓慢地将TMPTGE 4(65.77,0.22mol)的100mL的MeOH溶液加入混合物,进一步用100mL的MeOH冲洗。于80℃,搅拌反应24小时。然后,将于60℃反应用40-100mm Hg干燥直至产品变为固体,用高真空设备进一步干燥为恒定重量,产生白色固体37(160g,88%收率)。其谱图如下:
1H NMR(300MHz,D2O):δ0.8(m,3H),1.31(m,2H),3.25-4.1(br,30H),4.2(m,3H)。
下述方案18说明该反应。
方案18
实施例11:将来自三羟甲基丙烷缩水甘油基醚(TMPTGE)的产品与亚胺基二乙酸(IDA)反应
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=IDA;(TF)=CO2H;G=1]
向100mL MeOH溶液,加入IDA 36(91.5g,0.69mol),激烈搅拌直至完全溶解。在20分钟期间内缓慢地将TMPTGE 4(65.77,0.22mol)的100mL的MeOH溶液加入混合物,进一步用100mL的MeOH冲洗。于80℃搅拌反应24小时。然后,于60℃用40-100mm Hg干燥反应直至产品变为固体,用高真空设备进一步干燥至恒定重量,产生白色固体38(160g,88%收率)。其谱图如下:
1H NMR(300MHz,D2O):δ0.8(m,3H),1.31(m,2H),3.25-4.1(br,30H),4.2(m,3H),
下述方案19说明该反应。
方案19
实施例12:将实施例10的钠盐产品3离子交换为四丁基铵盐
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=IDA;(TF)=CO2NBu4;G=1]
将化合物37(来自实施例10)(2g,2.4mmol)溶于5mL的水,将其通过H形式的离子-交换树脂(IRC-50)。所述过程重复4次(2g的物质经过离子交换;总质量8g),提供pH 3的产品39。冻干经合并的级分,提供白色固体39(6.39g,84%收率)。将2g的化合物39溶于水(40mL),用大约5mL的0.86M氢氧化四丁基铵滴定至pH 8。再次用3.75g的化合物40重复滴定过程。合并溶液,冻干,产生白色固体40(7.95g)。其谱图如下:
1H NMR(300MHz,D2O):δ0.7-0.95(m,27H),1.31(m,18H),1.6(m,16H),3.1-3.85(br,46H),4.13(m,3H)
下述方案20说明该反应。
方案20
实施例13:将来自三羟甲基丙烷缩水甘油基醚(TMPTGE)产品与二苄胺(DBA)反应
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=DBA;(TF)=苄基;G=1]
向10mL MeOH溶液加入二苄胺41(1.18g,6.0mmol),进行搅拌。将TMPTGE 4(500mg,1.66mmol)的10mL的MeOH溶液缓慢地加入混合物,于45℃搅拌24小时。通过LCMS监测反应,其指出反应已完成。将反应混合物的样品通过HPLC在C18XTerra柱上纯化,用0.1%TFA/5-60%ACN梯度洗脱。减压除去反应溶剂,得到粗品的剩余物质42(1.53g)。其谱图如下:
1H NMR(300MHz,MeOD):δ0.65(t,3H),1.05(q,2H),2.98(br s,6H),3.05-3.3(br,12H),4.09(m,3H),4.47(m,12H),7.5(ArH,30H),和LCMS(亲水):Rf(min)9.8,(ESI+ve)实测894.31[M+H]+,计算C57H72N3O6。
下述方案21说明该反应。
方案21
实施例14:保护二亚乙基三胺的伯胺,用仲胺封盖三官能环氧化物
[(C)=TMPTGE;(IF1)=OH;(BR1)=DETA;(TF)=伯NH2;G=1]
将DETA 13(260.75g,2.5mol)和MIBK 43(1110g,11.1mol)加入2L圆底烧瓶,其配有Barrett疏水器和水冷回流冷凝器,在N2气氛下加热至110℃。随着水恒沸蒸出,反应温度增加至110℃,继续蒸馏直至Barrett疏水器底部不再收集到更多水。在N2下将反应混合物冷却至RT。旋转式蒸发除去最后的痕量MIBK 43,得到所希望的化合物44,是透明橙色液体,将其继续用于后续步骤。
在N2下,将亚胺保护的DETA 44(806g,3mol)与异丙醇(100mL)混合,搅拌,最终温热至60-70℃。将TMPTGE 4(302,1mol)溶于异丙醇(200mL),缓慢地加入(1.5-2小时)至温热的DETA-MIBK 44溶液,提供45。烧瓶用异丙醇(50mL)冲洗,加入反应混合物。在80℃搅拌反应混合物48小时。加入DI水(300mL),在80℃再搅拌16小时。反应温度增加至110℃,水恒沸蒸出。该步骤用600mL的DI水重复两次。将反应混合物冷却至RT,加水700mL。溶液用己烷(3x 300mL)萃取,然后将其弃去。将水溶液过滤通过粗滤器,减压除去溶剂。然后,对该物质进行Kugelrohr蒸馏(205℃和5mm Hg),产生产品46,是粘稠透明橙色半固体(498g,81.6%)。其谱图如下:
1H NMR(300MHz,MeOD):δ0.86(m,3H),1.14(m,2H),2.4-2.9(br,20H),3.2-3.75(br,16H),3.85(br s,3H)。ESI+ve实测612.16[M+H]+,计算C27H66N9O6。
下述方案22说明该反应。
方案22
实施例15:式(I)的PEHAM树枝状化合物的含农业活性物质的配制剂,其中所述活性物质的溶解度得以增加
向溶于适宜的挥发性有机溶剂(例如MeOH、DCM、EtOH、丙酮或其它适当的溶剂)的农业化学活性物的10%w/w溶液加入树枝状化合物在水或上述相同有机溶剂中的10%w/w溶液。搅拌混合物2-4小时,在此时间之后减压除去挥发性有机溶剂,提供活性物和树枝状化合物的1:1混合物。然后,将该油性溶液溶于水,过滤。通过HPLC或GLC测试分析水溶液中的活性物含量,提供对加入树枝状化合物引起的溶解度增加的估计。
将上述一般方法用于氟乐灵(已知具有极差水溶解度的农业化学品),展示两种不同的树枝状化合物显示显著增加了其水溶解度。
实施例16:式(I)的PEHAM树枝状化合物的含农业活性物质的配制剂,其中所述活性物质的溶解度得以增加
向溶于适宜的挥发性可与水混合的有机溶剂例如MeOH、EtOH、乙腈或丙酮的10%w/w农业化学活性物溶液加入PEHAM树枝状化合物的10%w/w水溶液。搅拌混合物2-4小时。然后调节至水溶液的水平以确保挥发性有机组分小于总体积的10%。在干冰丙酮浴中冷冻样品,冻干除去溶剂,产生无定形固体。将无定形固体溶于水,过滤,产生储备溶液。通过HPLC或GLC测试分析水溶液中的活性物含量,提供对加入树枝状化合物引起的溶解度增加的估计。测试了实施例2和14的PEHAM树枝状化合物,获得的结果类似实施例15的那些。
实施例17:在PEHAM树枝状化合物存在下农业活性物草甘膦的叶面穿透和效力的改善
样品制备:
用商业产品-(基于草甘膦IPA-盐)和(基于草甘膦钾盐)之一(各自为典型大田用量10mL/L或5mL/L(1%或0.5%))以及共五种PEHAM树枝状化合物制备5mL基质标准溶液,制备以使得各自提供0.05%或0.1%的最终浓度(这些是桶混中可能包括的助剂的典型浓度)。还制备相同用量和的两种对照溶液,不加任意树枝状化合物溶液。
表1
生物学评价:在温室中,使用蓟类植物
将上述各制备配制剂的单个5μl微滴通过微注射器施用至第三片叶子的近轴(上)表面的主脉一侧。于5天评价植物健康。继续试验,于14和21天间隔进行评价。下表2显示植物在5天之后(2=Touchdown对照,11=溶液4C)的状态。
表2
这些结果在5天的初步指征说明,相比其它溶液,溶液1A和4C显示中心边缘更高的"褐化(brown-out)"(得分10%,而对照为5%)。不期望受理论所限,据信使用本发明的树枝状化合物配制剂带来较高的损害百分比(也即树枝状化合物使得活性物更加有效),其原因可能是将更多活性物引入植物中、更快地灭除植物或者较低用量有较高活性。
观察结果的总结:
1.实质上不可能鉴定两种对照溶液的最初施用场所。
2.溶液5、6、7和10、11、12的施用场所有坏死损害的证据。
3.上述%损害得分主要是对出现的新生长物的"褐化"程度的评价。
4.掺入PEHAM树枝状化合物的处理组3和11显示显著更高的百分比损害,这清楚地指明树枝状化合物-草甘膦溶液穿透叶子表面并提供更高的效力。
实施例18:确定在PEHAM树枝状化合物存在下改善的农业化学品的叶面穿透
用上述实施例14所述的相同配制剂程序,用14C放射标记的农业化学品溶液[I4C-标记的莠去津1mCi/mmol,和草甘膦-一(异丙基铵)盐10-30mCi/mmol]制备一系列的农业化学品和PEHAM树枝状化合物的1:1混合物。将该油状混合物用水稀释至1%活性物水平,用于施用至植物。还制备对照溶液,其采用相同水平的农业化学品但不加入树枝状化合物。用微喷雾器,将14C-标记的除草剂的均匀微滴施用至豌豆植物的21天龄植株的第四片叶的背轴面相邻于主脉的圆形区域(10mm直径)。各处理组重复4次。让样品经历设定的摄取时间段(1-48小时),然后除下叶子,将背轴面依次用自注射器递送的MeOH+水(1mL;1+1体积)、随后MeOH(1mL)洗涤各20秒的持续时间。合并表面洗涤物,通过闪烁计数用Lumagel(Lumac)闪烁器测定放射性。随后,通过用氯仿(1mL)洗涤叶碟回收角质层蜡中保留的同位素标记。在氮气流中除去氯仿,然后通过液体闪烁计数(LSC)在加入'Hisafe 3'闪烁剂(4mL)之后测定在蜡提取物和表面洗涤物中的放射性。各样品间的相对放射性水平构成洗下的活性物量的直接比较。摄取定义为MeOH洗涤物中未回收的化学品的比例。
通过HPLC-UV光谱用Perkin ElmerTMLambda 2UV/VIS分光光度计和Waters HPLC能够测定较高水平的活性物。将树枝状化合物类配制剂的莠去津含量与莠去津对照(不含树枝状化合物)进行比较,以比较叶面穿透。
不期望受理论所限,据信本发明的含树枝状化合物的活性物质配制剂显示较高百分比的活性物质的叶上保留。
实施例19:用PEHAM树枝状化合物来增强在暴露于日光的情况下活性物质的稳定性
将上述农业化学活性物和PEHAM树枝状化合物(实施例15制备)的标准配制剂的5mL溶液置于玻璃培养皿中,暴露于日光2、4和8小时。在ARPANSA网站实时监测UV辐射。根据ARPANSA记录,将8小时的UV通量定为100%,计算2和4小时暴露的百分比。
在适当的时间间隔(2、4、8小时)之后,除下相应培养皿,冲洗并通过HPLC分析残余的活性成分和分解产品。
不期望受理论所限,据信本发明的含树枝状化合物的活性物质配制剂显示存在较高百分比的活性物;从而其受到保护免于UV损害。尽管一种活性物质经测试未显示有利结果,据信该配制剂应与其它活性物质同样有效。测试的活性物是嘧菌酯、氟虫腈、氟乐灵和戊唑醇。
实施例20:在PEHAM树枝状化合物存在下的农业活性物质土壤粘附/土壤穿透测试
作为初始试验,用10mL的含水活性物和1mL的5%树枝状化合物处理含10%水分的细砂测试柱体(大约8cm直径,10cm长度)。还制备不含树枝状化合物的对照柱体。
用含活性物的溶液对各柱体进行1天的淋洗。在该时间之后,将各柱体用额外的10mL的水处理以促进活性物在土壤柱中的运动。在三天之后,将各柱体切为三个水平部分,各部分通过HPLC或GLC测试活性物含量,从而能够构建土壤柱的垂直特征。将水洗脱液中的活性物质水平与土壤中的保留量比较,提供对于在含和不含PEHAM树枝状化合物情况下土壤粘附与穿透的相对水平的评价。
不期望受理论所限,据信本发明的含树枝状化合物和活性物质的配制剂会增加土壤穿透,从而活性物质将达到植物根部或植物的土壤下部分。
实施例21:树枝状化合物-铜配合物形成和增加的叶子保留/耐水牢度
储备1%硫酸铜溶液通过将10g的硫酸铜溶于1L水来制备。制备一系列的四种溶液:将0mg(0.0%w/v)、25mg(0.1%w/v)、50mg(1.0%w/v)或500mg(10.0%w/v)的PEHAM树枝状化合物加入5mL的如上制备的储备硫酸铜溶液。这些配合物短暂地暴露于超声,然后在37℃和100rpm振摇水浴中温育过夜,在RT平衡1小时。将树枝状化合物-硫酸铜活性物悬浮液过滤通过Whatman滤器以除去任意固体内容物。用标准过程分析样品中的铜。
将上述制备的各种PEHAM树枝状化合物-硫酸铜配制剂施用至植物叶子(3-5周龄),在温室中温育24小时。在24小时之后,将叶子轻柔地用10mL的水洗涤,收集全部洗涤水。通过UV光谱用PerkinElmerTMLambda 2UV/VIS分光光度计分析经合并的洗涤水的铜含量。另选地,低水平铜能够通过感应偶合等离子体原子发射光谱来检测。比较树枝状化合物类配制剂和对照(仅加铜)的铜含量。
不期望受理论所限,在本发明配制剂中将铜与树枝状化合物一起使用使得更少的铜从叶子洗去,从而较高百分比的活性铜保留在叶子上。铜用作葡萄上的杀真菌剂。从而,对于环境希望更低的铜施用(量和频率),同时仍可作为用于葡萄的杀真菌剂提供保护。
尽管本发明已参照优选实施方式进行描述,在阅读和理解其公开内容的基础上,本领域普通技术人员可以理解能够对其进行变化和修饰,而这不超出前文描述的或要求保护的本发明范围和主旨。
Claims (24)
1.用于农业的配制剂,其包含至少一种下式的PEHAM树枝状化合物
式(I)
其中:
(C)意指由PETGE、PETriGE或TMPTGE组成的核心;
(FF)意指核心的焦点官能团组分,其选自Et,OH,SH,NH2,CO2H,羧酸酯,直链或支链C1-C18烷基,芳基,芳基杂环部分,C1-C3烷氧基,三唑,C1-C18烷基酯,聚乙二醇和多氟化部分;
x独立地是0或1;
(BR)意指支化单元,如果p大于1,则(BR)可以是相同或不同的选自DBA,DEA,DEIDA,DETA,DIA,IDA,TREN,TRIS,甲基丙烯酸酯,和PETriGE的部分;
p是树枝状化合物中支化单元(BR)的总数并且是下述公式推演出的整数
其中:G是围绕核心的同心支化单元壳(代)的数目,其是1、2或3;
i是最终代G;
Nb是支化单元多重度;和
Nc是核心多重度并且是1至4的整数;
条件是在x是1的情况下,Nc-x必须是1至3的整数;
(IF)意指内部官能团,其是OH;
q独立地是0或1至64的整数;
(EX)意指延伸物,如果m大于1,则(EX)可以是相同或不同的部分,其选自氨基酸比如赖氨酸,聚(氨基酸)比如聚赖氨酸,寡聚乙二醇,二亚乙基四胺和高级胺类似物,作为5-元咪唑烷基衍生物保护的寡聚烷基烯胺,具有二个或更多不同或相同官能团的脂肪酸,不饱和的脂族和芳族二官能或多官能部分,EA,吗啉,二羧酸,EPC,IMAE,芳基二硫醇,二巯基烷烃,三唑类,DMI,二叠氮化物,联乙炔,吡咯烷酮,吡咯烷酮酯,氨基烷基咪唑啉,咪唑烷,聚(亚烷基咪唑烷),巯基烷基胺,羟基烷基胺或异质不饱和的脂族和芳族二官能或多官能部分;
m独立地是0或1至64的整数;
在q和m均大于1的情况下,(BR)和(EX)可以与另一部分交替出现或者按顺序与(BR)或(EX)的多个基团相继出现;
(TF)意指末端官能团,如果z大于1,则(TF)可以是相同或不同的部分,选自氨基,甲基氨基,乙基氨基,羟基乙基氨基,苄基氨基,巯基乙基氨基,二甲基氨基,二乙基氨基,二(羟基甲基)氨基,N-烷基化的氨基衍生物,N-芳基化的氨基衍生物,N-酰化的氨基衍生物,CO2-N(C1-C6烷基),羟基,巯基,羧基,羧酸盐,羧基C1-C18烷基,直链或支链C2-C18烯基,甲代烯丙基,酰胺基,卤代,脲,环氧乙烷基,氮丙啶基,噁唑啉基,咪唑啉基,吡咯烷酮,苄基,苯基,磺酸基,膦酸酯,异氰酸酯,异硫氰酸基,哌嗪基,乙基哌嗪基,丙烯酸酯,甲基丙烯酸酯,丙烯酰胺,叠氮化物,环氧化物,乙基亚胺,直链或支链C1-C18烷基,C1-C3烷氧基,C1-C18烷基酯,硫杂环丙烷,吗啉基,保护的DETA,聚乙二醇,多氟化部分,和树枝状物;
z意指,对于给定代G,1至(C)和(BR)可能的理论数的表面基团数,且由下述公式推演
z=NcNb G;
其中:G,Nb和Nc如上述定义;和
条件是存在(EX)或(IF)中至少一种;
与至少一种农业活性物质结合;和
存在至少一种农业上可接受的稀释剂或载体;和
其中农业活性物质的效力或活性持续时间得以增加。
2.权利要求1的配制剂,其中G=0,1或2。
3.权利要求1的配制剂,其中所述式(I)的PEHAM树枝状化合物是下述中任一:
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=DEA;(TF)=OH;G=1];
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=TRIS;(TF)=OH;G=1];
[(C)=PETGE;(IF1)=OH;(EX1)=三唑;(BR1)=PETriGE;(IF2)=OH;(BR2)=DEA;(TF)=OH;G=2];
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=IDA;(TF)=CO2Na;G=1];
[(C)=TMPTGE;(FF)=Et;(IF1)=OH;(BR1)=IDA;(TF)=CO2NBu4;G=1];或
[(C)=TMPTGE;(IF1)=OH;(BR1)=DETA;(TF)=伯NH2;G=1]。
4.权利要求1的配制剂,其中所述(EX)是三唑,哌嗪或吗啉。
5.权利要求1的配制剂,其中所述(BR)是DEA,DEIDA,DETA,TREN,和TRIS。
6.权利要求1的配制剂,其中所述(FF)是Et和OH。
7.权利要求1的配制剂,其中(TF)是氨基,羟基,羧基,羧酸盐,羧基乙基,CO2-N(四烷基),和氨基。
8.权利要求1的配制剂,其中q是1至64且存在至少一个(IF),其是OH。
9.权利要求1的配制剂,其中所述农业活性物质是杀虫剂,除草剂,杀真菌剂,或植物激素。
10.权利要求9的配制剂,其中所述农业活性物质是阿维菌素,乙酰甲胺磷,乙草胺,三氟羧草醚,甲草胺,莠去津,氟草胺,苯菌灵,灭草松,克菌丹,克百威,氯化苦,甲萘威,百菌清,百菌清,毒死蜱,氯磺隆氰草津,氢氧化铜,硫酸铜,三环锡,氯氰菊酯,茅草枯,2,4-二氯苯氧基乙酸(2,4-D),DCPA,二嗪磷,麦草畏,禾草灵,二甲吩草胺,除虫脲,地乐酚,敌草隆,茵多酸,茵草敌,乙烯利,福美铁,吡氟禾草灵,草甘膦,氟吡禾灵,马拉硫磷,代森锰锌,MCPP,甲霜灵,精甲霜灵,异丙甲草胺,精异丙甲草胺,嗪草酮,甲基砷酸钠,萘草胺;二甲戊灵,氯菊酯,氨氯吡啶酸,毒草胺,敌稗,烯禾啶,西玛津,精异丙甲草胺,甲磺草胺,sulfosate,双硫磷,特丁硫磷,三氯吡氧乙酸,氟乐灵,嗪氨灵,或代森锌。
11.权利要求9的配制剂,其中所述杀真菌剂是铜盐。
12.权利要求1的配制剂,其中所述配制剂为农业上可接受的粉剂,尘剂,颗粒剂,液剂,浓缩剂,悬浮剂,乳剂,喷雾剂,凝胶剂,或气雾剂的形式。
13.权利要求1的配制剂,其中使得农业活性物质可以自配制剂受控释放。
14.权利要求12或13的配制剂,其中对植物或种子的施用次数得以减少。
15.用权利要求1的配制剂处理植物或种子的方法,其中农业活性物质的效力或活性持续时间得以增加。
16.权利要求15的方法,其中所述配制剂增加农业活性物质的溶解度。
17.权利要求15的方法,其中所述配制剂改善农业活性物质对植物表面的粘着。
18.权利要求15的方法,其中所述配制剂改善农业活性物质对植物或种子的耐水牢度。
19.权利要求15的方法,其中所述配制剂改善农业活性物质向植物或种子的植物组织中的穿透(吸收)。
20.权利要求15的方法,其中所述配制剂增加农业活性物质的土壤穿透。
21.权利要求15的方法,其中所述配制剂减少农业活性物质的土壤粘着从而使得农业活性物质可以到达植物根部或土壤下部分。
22.权利要求15的方法,其中所述配制剂保护植物或种子免于使用配制剂导致的UV损害。
23.权利要求15的方法,其中所述配制剂在植物UV暴露期间保护农业活性物质免受UV损害。
24.权利要求15的方法,其中所述配制剂减少植物或种子或土壤中的微生物对农业活性物质的酶促降解。
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- 2010-10-26 DK DK10827405.1T patent/DK2493291T3/da active
- 2010-10-26 EP EP10827405.1A patent/EP2493291B1/en not_active Not-in-force
- 2010-10-26 BR BR112012009847-0A patent/BR112012009847B1/pt active IP Right Grant
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CN103992235A (zh) * | 2014-03-17 | 2014-08-20 | 香港应用科技研究院有限公司 | 用于电沉积的添加剂 |
CN108884018A (zh) * | 2015-12-16 | 2018-11-23 | 优星私人有限公司 | 树枝状聚合物和其制剂 |
US10981858B2 (en) | 2015-12-16 | 2021-04-20 | Priostar Pty Ltd | Dendrimer and formulations thereof |
CN108884018B (zh) * | 2015-12-16 | 2021-08-31 | 优星私人有限公司 | 树枝状聚合物和其制剂 |
CN111995536A (zh) * | 2018-06-25 | 2020-11-27 | 上海龙灯环保科技有限公司 | 季戊四醇四((n,n-二(2-氨基乙基))-3-氨基丙酸酯)的制备方法 |
CN111100094A (zh) * | 2019-12-31 | 2020-05-05 | 安徽新远科技有限公司 | 一种季戊四醇四缩水甘油醚合成方法 |
CN114878727A (zh) * | 2022-05-06 | 2022-08-09 | 合肥高尔生命健康科学研究院有限公司 | 一种测定烟草中噁霉灵残留物的方法 |
CN115299445A (zh) * | 2022-10-08 | 2022-11-08 | 云南省烟草公司昆明市公司 | 提升香菇多糖对植物诱导抗病性的复合溶液和配制方法、方法及植物田间防治病毒方法 |
CN115299445B (zh) * | 2022-10-08 | 2023-02-03 | 云南省烟草公司昆明市公司 | 提升香菇多糖对植物诱导抗病性的复合溶液和配制方法、方法及植物田间防治病毒方法 |
Also Published As
Publication number | Publication date |
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ES2731624T3 (es) | 2019-11-18 |
EP2493291B1 (en) | 2019-05-22 |
WO2011053605A1 (en) | 2011-05-05 |
BR112012009847B1 (pt) | 2021-04-13 |
US20110230348A1 (en) | 2011-09-22 |
EP2493291A1 (en) | 2012-09-05 |
JP5997050B2 (ja) | 2016-09-21 |
DK2493291T3 (da) | 2019-07-01 |
JP2013508460A (ja) | 2013-03-07 |
BR112012009847A2 (pt) | 2020-09-24 |
CN102781231B (zh) | 2014-12-24 |
EP2493291A4 (en) | 2013-08-21 |
AU2010313485A1 (en) | 2012-05-17 |
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