CN107787184B - 由四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺制备的壳的农药微胶囊 - Google Patents
由四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺制备的壳的农药微胶囊 Download PDFInfo
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- CN107787184B CN107787184B CN201680035472.8A CN201680035472A CN107787184B CN 107787184 B CN107787184 B CN 107787184B CN 201680035472 A CN201680035472 A CN 201680035472A CN 107787184 B CN107787184 B CN 107787184B
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- diisocyanate
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- tetramethylxylylene diisocyanate
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Classifications
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- A01G7/00—Botany in general
- A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
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- 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
- A01N25/26—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 in coated particulate form
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- 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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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
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- A—HUMAN NECESSITIES
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- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/72—Polyisocyanates or polyisothiocyanates
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
Abstract
本发明涉及一种包含微胶囊的组合物，其包含聚脲壳和核，其中所述核包含水不溶性农药且所述壳包含四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺的聚合产物；包括使水、农药、四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺接触的步骤的制备所述组合物的方法；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，其中使所述组合物作用于相应有害物或待保护以防相应有害物的作物植物上，作用于土壤上和/或作用于不希望的植物上和/或作用于作物植物和/或其环境。
Description
本发明涉及一种包含微胶囊的组合物，所述微胶囊包含聚脲壳和核，其中所述核包含水不溶性农药且所述壳包含四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺的聚合产物；包括使水、农药、四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺接触的步骤的制备所述组合物的方法；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，其中使所述组合物作用于相应有害物、其环境或待保护以防相应有害物的作物植物上，作用于土壤上和/或作用于不希望的植物上和/或作用于作物植物和/或其环境。本发明包括优选特征与其他优选特征的组合。
已知包含聚脲壳和农药核的农化微胶囊，但仍需要一些改进。US2003/119675公开了一种微胶囊悬浮液，其包含：A)微胶囊，其壳由甲苯二异氰酸酯和亚甲基双(环己基-4-异氰酸酯)与一种二胺和/或聚胺的混合物制备的壳，且核包含固体农药，液体脂族烃和油溶性聚合物分散剂，和B)水相，其可含有添加剂和未包封形式的其他农药。US 5925595公开了一种具有如下的微胶囊：(a)由如下组成的胶囊壁：(i)三异氰酸酯，其为线性脂族异氰酸酯的加合物；(ii)脂族二异氰酸酯，其含有脂环族或芳族环结构部分，和(iii)聚胺；和(b)包含两种不同核材料的核。US 2012/245027公开了一种包含含有在水中具有低溶解度的微包封材料(例如农药)的微胶囊的组合物，其中微胶囊壁借助芳族异氰酸酯、脂族异氰酸酯和乙炔脲衍生物的界面聚合反应形成。
该目的通过包含微胶囊的组合物实现，所述微胶囊包含聚脲壳和核，其中所述核包含水不溶性农药且所述壳包含a)四甲基苯二亚甲基二异氰酸酯、b)脂环族二异氰酸酯和c)脂族二胺的聚合产物。
合适的四甲基苯二亚甲基二异氰酸酯可以是间位或对位取代的四甲基苯二亚甲基二异氰酸酯。优选四甲基苯二亚甲基二异氰酸酯为式(II)化合物：
合适脂环族二异氰酸酯为1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(异佛尔酮二异氰酸酯，IPDI)、1,4-和/或1,3-双(异氰酸酯基甲基)环己烷(HXDI)、环己烷-1,4-二异氰酸酯、1-甲基-2,6-环己烷二异氰酸酯、1-甲基-2,4-环己烷二异氰酸酯、2,2'-二环己基甲烷二异氰酸酯、2,4'-二环己基甲烷二异氰酸酯或4,4'-二环己基甲烷二异氰酸酯。脂环族二异氰酸酯优选为4,4'-二环己基甲烷二异氰酸酯，其对应于式(I)化合物：
合适的脂族二胺具有式H2N-(CH2)n-NH2，其中n为2-8(优选4-6)的整数。该类二胺的实例是乙二胺、丙-1,3-二胺、四亚甲基二胺、五亚甲基二胺和六亚甲基二胺。优选的脂族二胺是六亚甲基二胺。
四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯(例如式(I)化合物)的重量比为通常25:1-2:1，优选15:1-4:1，特别是12:1-7:1。
聚脲壳包含通常至少35重量％，优选至少45重量％，特别是至少55重量％的四甲基苯二亚甲基二异氰酸酯。聚脲壳包含通常35-85重量％，优选45-80重量％，特别是55-75重量％的四甲基苯二亚甲基二异氰酸酯。聚脲壳中四甲基苯二亚甲基二异氰酸酯的重量％可涉及单体的总量。
聚脲壳包含通常至多50重量％，优选至多40重量％，特别是至多35重量％的脂环族二异氰酸酯(例如式(I)化合物)。聚脲壳包含通常1-30重量％，优选2-20重量％，特别是4-12重量％的脂环族二异氰酸酯(例如式(I)化合物)。聚脲壳中脂环族二异氰酸酯的重量％可涉及单体的总量。
聚脲壳包含通常至多50重量％，优选至多35重量％，特别是至多30重量％的脂族二胺(例如具有式H2N-(CH2)n-NH2，其中n为2-8的整数)。聚脲壳包含通常1-50重量％，1-30重量％，优选2-20重量％或15-35重量％，尤其是25-35重量％的脂族二胺(例如具有式H2N-(CH2)n-NH2，其中n为2-8的整数)。聚脲壳中脂族二胺的重量％可涉及单体的总量。
聚脲壳可包含其他多异氰酸酯，其具有至少两个异氰酸酯基团且其与四甲基苯二亚甲基二异氰酸酯和脂环族二异氰酸酯不同。聚脲壳包含通常至多10重量％，优选至多5重量％，特别是至多1重量％其他多异氰酸酯。聚脲壳中其他多异氰酸酯的重量％可涉及单体的总量。
聚脲壳可包含其他聚胺，其具有至少两个胺基团且其与脂族二胺不同。聚脲壳包含通常至多10重量％，优选至多5重量％，特别是至多1重量％其他聚胺。聚脲壳中其他聚胺的重量％可涉及单体的总量。
核与聚脲壳的重量比为通常50:1-5:1，优选40:1-10:1，特别是30:1-15:1。核的重量可基于农药、任选地水不混溶性有机溶剂和任选地其他溶剂的量。聚脲壳的重量可基于四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯、脂族二胺和任选地其他多异氰酸酯和其他聚胺的量。
在一个优选形式中，聚脲壳包含35-85重量％四甲基苯二亚甲基二异氰酸酯、1-30重量％脂环族二异氰酸酯(例如式(I)化合物)、1-30重量％脂族二胺(例如具有式H2N-(CH2)n-NH2，其中n为2-8的整数)、至多10重量％其他多异氰酸酯、至多10重量％其他聚铵，且四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯(例如式(I)化合物)的重量比为25:1-2:1，核与聚脲壳的重量比为50:1-5:1。
在另外的优选形式中，聚脲壳包含45-80重量％四甲基苯二亚甲基二异氰酸酯、2-20重量％脂环族二异氰酸酯(例如式(I)化合物)、15-35重量％脂族二胺(例如具有式H2N-(CH2)n-NH2，其中n为2-8的整数)、至多5重量％其他多异氰酸酯、至多5重量％其他聚铵，且四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯(例如式(I)化合物)的重量比为15:1-4:1，核与聚脲壳的重量比为40:1-10:1。
在另外的优选形式中，聚脲壳包含55-75重量％四甲基苯二亚甲基二异氰酸酯、4-12重量％脂环族二异氰酸酯(例如式(I)化合物)、25-35重量％脂族二胺(例如具有式H2N-(CH2)n-NH2，其中n为4-8的整数)、至多1重量％其他多异氰酸酯、至多1重量％其他聚铵，且四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯(例如式(I)化合物)的重量比为12:1-7:1，核与聚脲壳的重量比为30:1-15:1。
具有聚脲壳的微胶囊可类似于现有技术制备。它们优选通过合适的聚合物壁形成材料(如二异氰酸酯和二胺)的界面聚合方法制备。界面聚合通常在包含溶解在其中的至少一部分聚合物壁形成材料的核材料的水包油含水乳液或悬浮液中进行。在聚合期间，聚合物从核材料分离到核材料和水之间的边界表面，由此形成微胶囊的壁。由此可得到微胶囊材料的含水悬浮液。在现有技术中已经公开合适的制备含有农药化合物的微胶囊的界面聚合方法。通常，聚脲通过使至少一种二异氰酸酯与至少一种二胺反应形成，以形成聚脲壳。
微胶囊的平均尺寸(借助光散射的z-平均值；优选D4,3平均值)为0.5-50μm，优选0.5-20μm，更优选1-15μm，尤其是2-10μm。
微胶囊的核可包含水不混溶性有机溶剂。水不混溶性有机溶剂的合适实例是
-烃溶剂如脂族、环状和芳族烃(例如甲苯、二甲苯、链烷烃、四氢化萘、烷基化萘或其衍生物，中至高沸点的矿物油馏分(如煤油、柴油、煤焦油))；
-植物油如玉米油、菜籽油；
-脂肪酸酯如C10-C22脂肪酸的C1-C10烷基酯；或
-植物油的甲基或乙基酯如菜籽油甲基酯或玉米油甲基酯；
-部分皂化的脂肪和油类；
-松香和松香油。
上述水不混溶性有机溶剂的混合物也是可能的。水不混溶性有机溶剂通常可市购，例如烃以商品名
200、
200或
28市购。芳族烃可以贫萘品质的形式使用。优选的水不混溶性有机溶剂为烃类，特别是芳族烃类。
优选地，水不混溶性有机溶剂在水中在20℃下具有至多20g/l，更优选至多5g/l，特别是至多0.5g/l的溶解度。
通常，水不混溶性有机溶剂具有100℃以上，优选150℃以上，特别是180℃以上的沸点。
在一个优选形式中，微胶囊的核可包含至多10重量％，优选至多5重量％，特别是至多1重量％的水不混溶性有机溶剂。
微胶囊的核可包含其他溶剂，例如至多30重量％，优选至多15重量％，基于核中所有溶剂的总量。
微胶囊的核可包含至少90重量％，优选至少95重量％，特别是至少99重量％的农药、任选地水不混溶性有机溶剂和任选地其他溶剂的总和。在另外的形式中，微胶囊的核可由农药、任选地水不混溶性有机溶剂和任选地其他溶剂组成。
在一个优选形式中，微胶囊的核可包含至少90重量％，优选至少95重量％，特别是至少99重量％的农药。
该组合物可为含水组合物，其可包含水相(例如连续水相)。含水组合物可包含至少10重量％，优选至少25重量％，特别是至少35重量％的水。通常，微胶囊悬浮于含水组合物的水相中。
优选地，该组合物为含水组合物，且水相包含木素磺酸盐。合适的木素磺酸盐是碱金属盐和/或碱土金属盐和/或铵盐，例如木素磺酸的铵盐、钠盐、钾盐、钙盐或镁盐。非常特别优选使用钠盐、钾盐和/或钙盐。当然术语木素磺酸盐也包括不同离子的混合盐，例如木素磺酸钾/钠、木素磺酸钾/钙等，特别是木素磺酸钠/钙。
木素磺酸盐可基于硫酸盐浆木素。硫酸盐浆木素在使用氢氧化钠和硫化钠的木质素制浆方法中获得。可将硫酸盐浆木素磺化而获得木素磺酸盐。
木素磺酸盐的分子量可以为500-20000g/mol。优选地，木素磺酸盐的分子量为700-10000g/mol，更优选900-7000g/mol，特别是1000-5000g/mol。
木素磺酸盐通常可溶于水(例如在20℃下)，例如以至少5重量％，优选至少10重量％，特别是至少20重量％溶于水。
含水组合物包含通常0.1-5.0重量％，优选0.3-3.0重量％，特别是0.5-2.0重量％的木素磺酸盐。
术语“农药”通常是指至少一种选自杀真菌剂、杀虫剂、杀线虫剂、除草剂、安全剂、生物农药和/或生长调节剂的活性物质。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。也可使用两种或更多种上述类别的农药的混合物。本领域技术人员熟知该类农药，其可参见例如Pesticide Manual，第16版(2013)，The BritishCrop Protection Council，London。合适的杀虫剂为选自如下类别的杀虫剂：氨基甲酸酯类、有机磷酸酯类、有机氯杀虫剂、苯基吡唑类、拟除虫菊酯类、新烟碱类、斯皮诺素(spinosin)类、阿维菌素(avermectin)类、米尔贝霉素(milbemycin)类、保幼激素类似物、烷基卤、有机锡化合物、沙蚕毒素类似物、苯甲酰脲类、双酰肼类、METI杀螨剂；以及杀虫剂如氯化苦(chloropicrin)、拒嗪酮(pymetrozin)、氟啶虫酰胺(flonicamid)、四螨嗪(clofentezin)、噻螨酮(hexythiazox)、特苯
唑(etoxazole)、杀螨硫隆(diafenthiuron)、克螨特(propargite)、三氯杀螨砜(tetradifon)、氟唑虫清(chlorfenapyr)、二硝甲酚(DNOC)、噻嗪酮(buprofezine)、灭蝇胺(cyromazine)、虫螨脒(amitraz)、灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)、鱼藤酮(rotenone)或其衍生物。合适的杀真菌剂为如下类别的杀真菌剂：二硝基苯胺类、烯丙基胺类、苯胺基嘧啶类、抗生素、芳族烃类、苯磺酰胺类、苯并咪唑类、苯并异噻唑类、二苯甲酮类、苯并噻二唑类、苯并三嗪类、苄基氨基甲酸酯类、氨基甲酸酯类、羧酰胺类、羧酸二酰胺类、氯腈类、氰基乙酰胺肟类、氰基咪唑类、环丙烷羧酰胺类、二羧酰亚胺类、二氢二
嗪类、二硝基苯基巴豆酸酯类、二硫代氨基甲酸酯类、二硫戊环类、乙基膦酸酯类、乙基氨基噻唑羧酰胺类、胍类、羟基-(2-氨基)嘧啶类、羟基苯胺类、咪唑类、咪唑啉酮类、无机物质、异苯并呋喃酮类、甲氧基丙烯酸酯类、甲氧基氨基甲酸酯类、吗啉类、N-苯基氨基甲酸酯类、
唑烷二酮类、肟基乙酸酯类、肟基乙酰胺类、肽基嘧啶核苷类、苯基乙酰胺类、苯基酰胺类、苯基吡咯类、苯基脲类、膦酸酯类、硫代磷酸酯类、邻氨甲酰苯甲酸类、苯邻二甲酰亚胺类、哌嗪类、哌啶类、丙酰胺类、哒嗪酮类、吡啶类、吡啶基甲基苯甲酰胺类、嘧啶胺类、嘧啶类、嘧啶酮腙类、吡咯并喹啉酮类、喹唑啉酮类、喹啉类、醌类、磺酰胺类、氨磺酰基三唑类、噻唑羧酰胺类、硫代氨基甲酸酯类、苯硫脲酯类(thiophanate)、噻吩羧酰胺类、甲苯甲酰胺类、三苯基锡化合物、三嗪类、三唑类。合适的除草剂为如下类别的除草剂：乙酰胺类、酰胺类、芳氧基苯氧基丙酸酯类、苯甲酰胺类、苯并呋喃类、苯甲酸类、苯并噻二嗪酮类、联吡啶
类、氨基甲酸酯类、氯乙酰胺类、氯羧酸类、环己烷二酮类、二硝基苯胺类、二硝基苯酚、二苯醚、甘氨酸类、咪唑啉酮类、异
唑类、异
唑烷二酮类、腈类、N-苯基苯邻二甲酰亚胺类、
二唑类、
唑烷二酮类、氧基乙酰胺类、苯氧基羧酸类、苯基氨基甲酸酯类、苯基吡唑类、苯基吡唑啉类、苯基哒嗪类、次膦酸类、氨基磷酸酯类、二硫代磷酸酯类、邻氨甲酰苯甲酸酯类、吡唑类、哒嗪酮类、吡啶类、吡啶羧酸类、吡啶羧酰胺类、嘧啶二酮类、嘧啶基(硫代)苯甲酸酯类、喹啉羧酸类、缩氨基脲类、磺酰氨基羰基三唑啉酮类、磺酰脲类、四唑啉酮类、噻二唑类、硫代氨基甲酸酯类、三嗪类、三嗪酮类、三唑类、三唑啉酮类、三唑羧酰胺类、三唑并嘧啶类、三酮类、尿嘧啶类、脲类。优选农药是除草剂如胺硝草(pendimethalin)。
农药是水不溶性的。农药在水中在20℃下具有至多10g/l，优选至多1g/l，特别是至多0.5g/l的溶解度。
农药可在20℃下是液体或固体，其中优选液体形式。在一个形式中，农药具有0-120℃，优选20-90℃，特别是35-70℃的熔点。
核通常包含液体形式(例如当核不含水不混溶性有机溶剂时；或当核由农药组成时)，或溶解在水不混溶性有机溶剂中的农药。优选核包含液体形式的农药(例如当核不含水不混溶性有机溶剂时；或当核由农药组成时)。
该组合物(例如含水组合物)通常包含至少1重量％，优选至少3重量％，特别是至少10重量％的包封农药。
该组合物可包含未包封农药。该未包封农药可以以溶解形式存在，或作为悬浮液、乳液或悬浮乳液存在。它可能与核中的农药相同或不同。含水组合物可在水相中包含未包封农药。含水组合物通常包含至少1重量％，优选至少3重量％，特别是至少10重量％的未包封农药。
该组合物还可含有水溶性无机盐，其可由微胶凝的制备得到或其可在此后加入。如果存在，则水溶性无机盐的浓度可为1-200g/l，优选2-150g/l，尤其是10-130g/l。盐的水溶性意指在水中的溶解度在20℃下为至少50g/l，尤其是至少100g/l或甚至至少200g/l。
该类无机盐优选选自碱金属的硫酸盐、氯化物、硝酸盐、磷酸单氢盐和磷酸二氢盐，氨的硫酸盐、氯化物、硝酸盐、磷酸单氢盐和磷酸二氢盐，碱土金属的氯化物和硝酸盐以及硫酸镁。实例包括氯化锂、氯化钠、氯化钾、硝酸锂、硝酸钠、硝酸钾、硫酸锂、硫酸钠、硫酸钾、磷酸单氢钠、磷酸单氢钾、磷酸二氢钠、磷酸二氢钾、氯化镁、氯化钙、硝酸镁、硝酸钙、硫酸镁、氯化铵、硫酸铵、磷酸单氢铵和磷酸二氢铵等。优选的无机盐为氯化钠、氯化钾、氯化钙、硫酸铵和硫酸镁，其中特别优选硫酸铵和硫酸镁。
在另外的实施方案中，该组合物不含或含有小于10g/l，尤其是小于1g/l的水溶性无机盐。
该组合物可包含二醇，例如乙二醇、丙二醇。该组合物可包含1-250g/l，优选10-150g/l，尤其是30-100g/l二醇。
该组合物可在微胶囊外侧，例如在含水组合物的水相中包含其他辅助剂。合适辅助剂的实例为表面活性剂、分散剂、乳化剂、润湿剂、助剂、加溶剂、渗透提高剂、保护性胶体、粘合剂、增稠剂、保湿剂、趋避剂、引诱剂、进食刺激剂、增容剂、杀菌剂、消泡剂、防冻剂、着色剂、增粘剂和粘结剂。
合适的表面活性剂为表面活性化合物，例如阴离子、阳离子、非离子和两性表面活性剂、嵌段聚合物、聚电解质及其混合物。该类表面活性剂可用作乳化剂、分散剂、加溶剂、润湿剂、渗透提高剂、保护性胶体或助剂。表面活性剂的实例列于McCutcheon’s，第1卷：Emulsifiers&Detergents，McCutcheon’s Directories，Glen Rock，USA，2008(国际版或北美版)中。
合适的阴离子表面活性剂为磺酸、硫酸、磷酸、羧酸及其混合物的碱金属、碱土金属或铵盐。磺酸盐的实例为烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、烷氧基化芳基酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例为脂肪酸和油的硫酸酯盐、乙氧基化烷基酚的硫酸酯盐、醇的硫酸酯盐、乙氧基化醇的硫酸酯盐、脂肪酸酯的硫酸盐。磷酸盐的实例为磷酸酯盐。羧酸盐的实例为烷基羧酸盐和羧化醇或烷基酚乙氧基化物。术语磺酸盐是指与木素磺酸盐不同的化合物。
合适的非离子表面活性剂为烷氧基化物，N-取代的脂肪酸酰胺，胺氧化物，酯，糖基表面活性剂，聚合物表面活性剂及其混合物。烷氧基化物的实例为诸如已经被1-50当量烷氧基化的醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯的化合物。可将氧化乙烯和/或氧化丙烯用于烷氧基化，优选氧化乙烯。N-取代的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。酯的实例为脂肪酸酯，甘油酯或甘油单酯。糖基表面活性剂的实例为脱水山梨醇、乙氧基化脱水山梨醇、蔗糖和葡萄糖酯或烷基多葡糖苷。聚合物表面活性剂的实例为乙烯基吡咯烷酮、乙烯醇或乙酸乙烯酯的均聚物或共聚物。
合适的阳离子表面活性剂为季型表面活性剂，例如具有1或2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为烷基甜菜碱和咪唑啉类。合适的嵌段聚合物为包含聚氧化乙烯和聚氧化丙烯嵌段的A-B或A-B-A型嵌段聚合物，或包含链烷醇、聚氧化乙烯和聚氧化丙烯的A-B-C型嵌段聚合物。合适的聚电解质为聚酸或聚碱。聚酸的实例为聚丙烯酸的碱金属盐或聚酸梳状聚合物。聚碱的实例是聚乙烯基胺或聚乙烯胺。
合适的助剂是本身具有可忽略的农药活性或者本身甚至没有农药活性且改善化合物I对目标物的生物学性能的化合物。实例为表面活性剂，矿物油或植物油以及其他辅助剂。其他实例由Knowles，Adjuvants and Additives，Agrow Reports DS256，T&F InformaUK，2006，第5章列出。
合适的增稠剂为多糖(例如黄原胶、羧甲基纤维素)、无机粘土(有机改性的或未改性的)、聚羧酸盐和硅酸盐。
合适的杀菌剂为拌棉醇(bronopol)和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。
合适的消泡剂为聚硅氧烷、长链醇和脂肪酸的盐。
合适的防冻剂为脲、乙二醇、丙二醇、甘油和甲酸钾。
本发明还涉及一种制备该组合物的方法，该方法包括使水、所述农药、四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺接触的步骤。接触可通过混合各组分，例如在20-100℃的温度下进行。
此外，本发明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，其中使本发明的组合物作用于相应有害物、其环境或待保护以防该相应有害物的作物植物上、作用于土壤上和/或作用于不希望的植物和/或作物植物和/或其环境。
合适作物的实例为禾谷类，例如小麦、黑麦、大麦、小黑麦、燕麦或稻；甜菜，例如糖用甜菜或饲用甜菜；仁果、核果和浆果，例如苹果、梨、李、桃、杏仁、樱桃、草莓、悬钩子、黑莓或鹅莓；豆科植物，例如蚕豆、兵豆、豌豆、苜蓿或大豆；油料作物，例如油菜籽油菜、芥菜、橄榄、向日葵、椰子、可可豆、蓖麻豆、油棕、花生或大豆；葫芦科植物，例如南瓜、黄瓜或甜瓜；纤维作物，例如棉花、亚麻、大麻或黄麻；柑桔类水果，例如橙子、柠檬、葡萄柚或橘；蔬菜植物，例如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、西红柿、土豆、南瓜或或柿子椒；月桂科植物，例如鳄梨、肉桂或樟脑；能量作物和工业原料作物，例如玉米、大豆、小麦、油菜籽油菜、甘蔗或油棕；玉米；烟草；坚果；咖啡；茶；香蕉；葡萄(食用葡萄和酿酒用葡萄)；啤酒花；禾草，例如草坪；甜叶菊(Stevia rebaudania)；橡胶植物和森林植物，例如花卉、灌木、落叶树和针叶树；和植物繁殖材料，例如种子；以及这些植物的收获产品。
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，包括上市销售或处于开发过程中的农业生物技术产品。基因修饰植物是其基因材料以在自然条件下无法通过杂交、突变或自然重组(即基因材料的重组)进行的方式修饰的植物。此时，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。该类重组修饰还包括蛋白质、寡肽或多肽的翻译后修饰，例如通过糖基化或连接聚合物，例如异戊二烯化、乙酰化或法呢基化基团或PEG基团。
用户通常由预剂量装置、背包式喷雾器、喷雾桶、喷雾飞机或灌溉系统施用本发明的组合物。通常用水、缓冲剂和/或其他辅助剂将所述农业化学组合物配制至所需的施用浓度，由此获得即用喷雾液或本发明的农业化学组合物。每公顷农业利用区通常施用20-2000升，优选50-400升即用喷雾液。
可向包含它们作为预混物的农化组合物中加入各种类型的油、润湿剂、助剂、肥料或微量营养素和其他农药(例如除草剂、杀虫剂、杀真菌剂、生长调节剂、安全剂)，或者合适的话在紧临使用前加入(桶混)。这些试剂可以以1:100-100:1，优选1:10-10:1的重量比与本发明的组合物混合。
当用于植物保护中时，活性物质的施用量取决于所需的效果类型为0.001-2kg/ha，优选0.005-2kg/ha，更优选0.05-0.9kg/ha，特别是0.1-0.75kg/ha。在植物繁殖材料如种子的处理(例如通过撒粉、包衣或浸泡种子)中，通常要求活性物质的量为0.1-1000g/100kg，优选1-1000g/100kg，更优选1-100g/100kg，最优选5-100g/100kg繁殖材料(优选种子)。
本发明具有各种优点：该组合物在长时间的储存期间稳定，例如甚至在宽温度范围；该组合物可用水稀释之后施加而不堵塞喷嘴；该组合物在用水稀释之后稳定；该组合物可与各种其他作物保护产品混合；存在由有色农药导致的设备、农夫或作物的染色降低；降低农药的挥发性；降低UV敏感性；农药在施用至作物之后更稳定。
下文实施例进一步阐述了本发明，而不限于这些实施例。
实施例
TMXDI：四甲基间苯二亚甲基二异氰酸酯，CAS 2778-42-9。
环状二异氰酸酯：双(4-异氰酸酯基环己基)甲烷(式(I)化合物)。
添加剂A：萘磺酸盐缩合物的钠盐。
添加剂B：疏水改性的聚丙烯酸酯、阴离子聚合物分散剂、粉状、分子量为1-20kDa，pH为7-8.5(1重量％，在水中)。
木素磺酸盐：木素磺酸的钠盐，基于硫酸盐浆木素，分子量约3000g/mol，水溶性，CAS 68512-34-5。
实施例1
在65℃下将包含农药、TMXDI和环状二异氰酸酯的油相加入水相(包含木素磺酸盐、硫酸镁七水合物)且使用高剪切设备乳化。在乳化之后，乳化设备由低剪切搅拌器替换且加入六亚甲基二胺。随后，将分散体在60℃下平稳搅拌30-60分钟。在搅拌下，将包含添加剂A、黄原胶、硅消泡剂和生物杀伤剂的处理水溶液(aqueous finish solution)加入胶囊分散体，并通过加入乙酸将pH调节至pH 6-8。微胶囊的平均尺寸为6.5μm.
表1:
| 量[g/l] | |
| 胺硝草 | 455 |
| TMXDI | 15,05 |
| 环状二异氰酸酯 | 1,67 |
| 六亚甲基二胺 | 6,6 |
| 木素磺酸盐 | 12,5 |
| 添加剂A | 4,7 |
| 硫酸镁 | 114 |
| 黄原胶 | 0,45 |
| 硅消泡剂 | 0,6 |
| 生物杀伤剂 | 2 |
| 水 | 加至1,0升 |
实施例2
微胶囊如实施例1制备。各组分的量列于表2中。微胶囊的平均尺寸为7μm。
表2:
实施例3
微胶囊如实施例1制备。各组分的量列于表3中。微胶囊的平均尺寸为6.9μm。
表3:
| 量[g/l] | |
| 胺硝草 | 455 |
| TMXDI | 15,05 |
| 环状二异氰酸酯 | 1,67 |
| 六亚甲基二胺 | 6,6 |
| 木素磺酸盐 | 12,5 |
| 添加剂B | 5 |
| 硫酸镁 | 114 |
| 黄原胶 | 0,45 |
| 硅消泡剂 | 0,6 |
| 生物杀伤剂 | 2 |
| 水 | 加至1,0升 |
实施例4
测试按照如实施例1所述的程序在实施例1、2和3中制备的微胶囊的样品的稀释稳定性和堵塞喷嘴。将样品用水稀释以制备适用于3L/ha产品与200L/ha水的施用率的喷雾桶混物。使喷雾桶混物在泵回路中在金属筛(150μm)上循环。在1h、2h、2,5h和4h之后，将回路再填充新鲜喷雾桶混物。然后，停止循环过夜且在室温下保持。第二天，将回路再填充并循环另外一小时。在结束时，使回路出料，并评价筛上的残留物。观察到较少量的橙色残余物，其未堵塞筛。
因此，这证实实施例1、2和3的组合物可在用水稀释之后施加而不堵塞喷嘴，且该组合物在用水稀释之后稳定。
实施例5(对比)
按照如实施例1所述的程序制备对比微胶囊。各组分的量列于表4中。基本上，该对比例与实施例1的组合物相同但不含环状二异氰酸酯。
如实施例4所述测试在该实施例5中制备的微胶囊的样品的稀释稳定性和堵塞喷嘴。在前2个小时之后，由于大量橙色残留物，堵塞泵回路中金属筛。循环不能继续。
因此，这证实该对比组合物由于堵塞喷嘴不能在用水稀释之后施加，且该对比组合物在用水稀释之后不稳定。
表4:
| 量[g/l] | |
| 胺硝草 | 455 |
| TMXDI | 15 |
| 环状二异氰酸酯 | --- |
| 六亚甲基二胺 | 6 |
| 木素磺酸盐 | 11 |
| 添加剂A | 4 |
| 硫酸镁 | 100 |
| 黄原胶 | 0,4 |
| 硅消泡剂 | 0,5 |
| 生物杀伤剂 | 2 |
| 水 | 加至1,0升 |
实施例6(对比)
按照如实施例1所述的程序制备微胶囊，得到相似评价尺寸的微胶囊。各组分的量列于表5中。
为了对比，表5中配方的变化在于基于摩尔由2,4-和2,6-甲苯二异氰酸酯(TDI)的可市购异构体混合物替换TMXDI。以如实施例1所述的方式实现包封的尝试失败。在加入六亚甲基二胺之后，所得水溶液的粘度增加且得到包含规则微胶囊以及大量聚合物颗粒的粘性浆料。浆料不能进一步加工且丢弃。表5:
| 量[g/l] | |
| 胺硝草 | 455 |
| TMXDI | 15,05 |
| 环状二异氰酸酯 | 1,67 |
| 六亚甲基二胺 | 6,6 |
| 木素磺酸盐 | 15 |
| 添加剂A | 12 |
| 添加剂B | 15 |
| 硫酸镁 | 120 |
| 黄原胶 | 0,45 |
| 硅消泡剂 | 1 |
| 生物杀伤剂 | 2 |
| 水 | 加至1,0升 |
Claims (17)
1.一种包含微胶囊的组合物，所述微胶囊包含聚脲壳和核，其中所述核包含农药且所述壳包含d)四甲基苯二亚甲基二异氰酸酯、e)脂环族二异氰酸酯和f)脂族二胺的聚合产物，其中所述农药在水中在20℃下具有至多10g/l的溶解度，其中所述四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯的重量比为15:1-4:1，其中所述脂族二胺具有式H2N-(CH2)n-NH2，其中n为2-8的整数。
2.根据权利要求1的组合物，其中所述脂环族二异氰酸酯为式(I)化合物：
3.根据权利要求1的组合物，其中所述四甲基苯二亚甲基二异氰酸酯为式(II)化合物：
4.根据权利要求2的组合物，其中所述四甲基苯二亚甲基二异氰酸酯为式(II)化合物：
5.根据权利要求1-4中任一项的组合物，其中所述核与聚脲壳的重量比为50:1-5:1。
6.根据权利要求1-4中任一项的组合物，其中所述核与聚脲壳的重量比为40:1-10:1。
7.根据权利要求1-4中任一项的组合物，其中所述核与聚脲壳的重量比为30:1-15:1。
8.根据权利要求1-4中任一项的组合物，其中所述四甲基苯二亚甲基二异氰酸酯与脂环族二异氰酸酯的重量比为12:1-7:1。
9.根据权利要求1-4中任一项的组合物，其中所述聚脲壳包含至少45 重量％的四甲基苯二亚甲基二异氰酸酯。
10.根据权利要求1-4中任一项的组合物，其中所述聚脲壳包含至多20重量％的脂环族二异氰酸酯。
11.根据权利要求1-4中任一项的组合物，其中所述聚脲壳包含至多10重量％的其他多异氰酸酯，其具有至少两个异氰酸酯基团，且其与四甲基苯二亚甲基二异氰酸酯和脂环族二异氰酸酯不同。
12.根据权利要求1-4中任一项的组合物，其中所述聚脲壳包含至多10重量％的其他聚胺，其具有至少两个胺基团且其与脂族二胺不同。
13.根据权利要求1-4中任一项的组合物，其中所述组合物为含水组合物，且水相包含木素磺酸盐。
14.根据权利要求1-4中任一项的组合物，其中所述组合物包含0. 3-3. 0重量％的木素磺酸盐。
15.根据权利要求1-4中任一项的组合物，其中所述核包含水不混溶性有机溶剂。
16.一种制备如权利要求1-15中任一项所定义的组合物的方法，包括使水、农药、四甲基苯二亚甲基二异氰酸酯、脂环族二异氰酸酯和脂族二胺接触的步骤。
17.一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/或调节植物生长的非治疗方法，其中使如权利要求1-15中任一项所定义的组合物作用于相应有害物或待保护以防相应有害物的作物植物上，作用于土壤上和/或作用于不希望的植物上和/或作用于作物植物和/或其环境。
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| WO2021055314A1 (en) * | 2019-09-16 | 2021-03-25 | Eastman Chemical Company | Substantially non-phytotoxic formulation containing a sulfopolymer |
| UY39016A (es) * | 2020-01-17 | 2021-08-31 | Monsanto Technology Llc | Composiciones herbicidas con sales de monoetanolamina de herbicidas de auxina con propiedades mejoradas |
| KR20230115486A (ko) * | 2022-01-27 | 2023-08-03 | 주식회사 다우테크 | 방충 성능이 우수한 농업용 멀칭비닐 및 이의 제조방법 |
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| US10765112B2 (en) | 2020-09-08 |
| AU2016278591A1 (en) | 2017-12-14 |
| KR20180019207A (ko) | 2018-02-23 |
| ES2760562T3 (es) | 2020-05-14 |
| WO2016202500A1 (en) | 2016-12-22 |
| EP3310165A1 (en) | 2018-04-25 |
| MX2017016854A (es) | 2018-05-28 |
| CO2017013052A2 (es) | 2018-05-10 |
| EA201890088A1 (ru) | 2018-05-31 |
| CA2987317C (en) | 2021-09-14 |
| EP3310165B1 (en) | 2019-09-11 |
| CL2017003117A1 (es) | 2018-04-02 |
| JP6749947B2 (ja) | 2020-09-02 |
| BR112017025494B1 (pt) | 2021-10-19 |
| AR105041A1 (es) | 2017-08-30 |
| AU2016278591B2 (en) | 2020-12-17 |
| EA035541B1 (ru) | 2020-07-01 |
| CR20180046A (es) | 2018-04-30 |
| CN107787184A (zh) | 2018-03-09 |
| CA2987317A1 (en) | 2016-12-22 |
| IL256090B (en) | 2020-04-30 |
| ECSP18004165A (es) | 2018-03-31 |
| IL256090A (en) | 2018-02-28 |
| ZA201800230B (en) | 2019-06-26 |
| HUE046882T2 (hu) | 2020-03-30 |
| BR112017025494A2 (pt) | 2018-08-07 |
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