CN103945691B - 具有酰胺和酰基吗啉的农业配制剂 - Google Patents
具有酰胺和酰基吗啉的农业配制剂 Download PDFInfo
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- CN103945691B CN103945691B CN201280056440.8A CN201280056440A CN103945691B CN 103945691 B CN103945691 B CN 103945691B CN 201280056440 A CN201280056440 A CN 201280056440A CN 103945691 B CN103945691 B CN 103945691B
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- acyl group
- carbon atom
- morpholine
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 36
- 150000001408 amides Chemical class 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 title claims description 29
- 239000004480 active ingredient Substances 0.000 claims abstract description 36
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000000839 emulsion Substances 0.000 claims description 28
- 239000003995 emulsifying agent Substances 0.000 claims description 21
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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- 239000004094 surface-active agent Substances 0.000 claims description 9
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 7
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- 150000002431 hydrogen Chemical class 0.000 claims description 5
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- 239000000080 wetting agent Substances 0.000 claims description 4
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical class N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
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- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 2
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
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Abstract
本发明提供了一种配制剂，其包含a)至少一种农业活性成分；b)至少一种式(I)酰胺，其中R1选自具有1-16个碳原子的非芳族烃基和苄基；R2选自具有1-4个碳原子的烃基和苄基；且R3选自氢和具有1-16个碳原子的烃基，和c)至少一种式(II)酰基吗啉，其中R为H、CH3或C2H5。还提供用这类配制剂处理植物或种子的方法。
Description
发明领域
本发明涉及作为农业活性成分的溶剂的包含酰胺、酰基吗啉和任选其它组分的溶剂体系。本发明还涉及包含农业活性成分和这类溶剂体系的配制剂。
发明背景
农业活性成分，例如农药和植物生长调节剂通常以不同的浓缩形式提供给最终使用者，由最终使用者在水或其它合适介质中稀释以形成稀释的即用配制剂。这类浓缩形式包括固体配制剂，例如粉末，和液体配制剂。在许多应用中，液体配制剂由于可避免有毒粉末的粉尘和在稀释剂中缓慢溶解的问题而是优选的。
乳液浓缩物通常包含农业活性成分、水不溶性溶剂和乳化剂，并且在加入水中时它自发地，或者在活性混合如搅拌以后形成水包油乳液，农业活性成分主要以乳液滴存在。这类浓缩配制剂尤其适于水不溶性/具有低水溶性，且其中即用配制剂中推荐的浓度超过农业活性成分的溶解度的农业活性物质。
重要的是农业活性成分稳定地溶于乳液浓缩物中。农业活性成分的沉淀可导致效力损失。如果农业活性成分浓缩成沉淀物，则防止它在喷雾到农田时均匀地分布。
因此，本领域中需要找到用于农业活性成分的新型且改进的溶剂/溶剂体系，其可用于农业配制剂，尤其是乳液浓缩物的形式。
发明概述
本发明的一个目的是满足本领域中的需要和提供可用于农业配制剂中的溶剂。
本发明的另一目的是提供用于农业活性物质的溶剂，其允许用于溶剂和农业活性物质的浓缩配制剂，其中农业活性成分具有降低的形成沉淀物的倾向。
本发明的另一目的是提供用于农业活性成分的溶剂，其允许用于使溶剂和农业活性物质的浓缩配制剂与含水介质混合而不具有或仅具有少量活性成分沉淀。
本发明者现在惊讶地发现包含酰胺和酰基吗啉的某些组合适用作农业活性成分的溶剂体系。这些组合可用于可乳化浓缩配制剂中。
在第一方面中，本发明涉及一种配制剂，所述配制剂包含：
a)农业活性成分，
b)至少一种式(I)酰胺，
其中：
R1选自具有1-16个碳原子的非芳族烃基和苄基；
R2选自具有1-4个碳原子的烃基和苄基；且
R3选自氢和具有1-16个碳原子的烃基，
c)式(II)酰基吗啉：
其中R为H、CH3或C2H5，
d)任选不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂，和
e)任选其它组分。
配制剂可以为完全或基本无水配制剂或者可以为含水配制剂如乳液。
在第二方面中，本发明涉及通过使所述植物与本发明配制剂接触而处理植物的方法。
在第三方面中，本发明涉及包含式(I)酰胺和式(II)酰基吗啉以及任选极性非质子溶剂的溶剂体系作为农业活性物质的溶剂的用途。
现在进一步描述这些和其它方面。
发明详述
预期用于本发明中的农业活性成分，在本领域中也称为农业活性物质，优选选自农药和植物生长调节剂。
农业活性成分优选选自具有低水溶性的那些，最优选选自水不溶的那些。
如本文所用术语“农业活性成分”视为包括为农业活性的任何有机化合物。然而，就如本文所定义的式(I)酰胺、式(II)酰基吗啉或极性非质子助溶剂而言，其具有农业活性，这些不被认为是农业活性成分。
如本文所定义，术语“具有低水溶性的化合物”涉及在水中具有至多5g/l，例如至多1g/l，例如至多0.7g/l的溶解度的化合物。
在本发明上下文中，水溶性应当理解根据ASTM E1148-87“StandardTest Method for Measurements of Aqueous Solubility”测量。
如本文所用，术语“农药”指会防止、破坏、驱逐或减轻任何害虫的化合物。
如本文所用，术语“植物生长调节剂”指通过生理作用加速或减缓生长速率或成熟速率或者改变观赏或农作物或其产物的习性的化合物。
尤其预期用于本发明中的农药和植物生长调节剂为有机化合物，优选合成有机化合物。
预期用于本发明中的农药包括杀真菌剂、除草剂、杀虫剂、杀螨剂、杀线虫剂、杀螨蜱剂和软体动物杀灭剂。
预期用于本发明中的优选农业活性成分包括三唑类、嗜球果伞素类、亚烷基双(二硫代氨基甲酸酯)化合物类、苯并咪唑类、苯氧基羧酸类、苯甲酸类、磺酰脲类、三嗪类、吡啶羧酸类、新烟碱类(neonicotinoids)、脒类、有机磷酸酯类和拟除虫菊酯类的农药和植物生长调节剂。
本发明的合适杀真菌剂的实例包括三唑类(例如戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、环唑醇(cyproconazole)、氧唑菌(epoxiconazole)、苯醚甲环唑(difenconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole))、嗜球果伞素类(例如肟菌酯(trifloxystrobin)、腈嘧菌酯(azoxystrobin)、氟嘧菌酯(fluoxastrobin)、唑菌胺酯(pyraclostrobin))、亚烷基双(二硫代氨基甲酸酯)化合物类(例如代森锰锌(mancozeb))和苯并咪唑类(例如多菌灵(carbendazim))的杀真菌剂。
本发明的合适除草剂的实例包括苯氧基羧酸类(例如2,4-D-酸、MCPA)、苯甲酸类(例如麦草畏酸(Dicamba-acid))、磺酰脲类(例如甲磺隆(methylsulfuron-methyl)、玉嘧黄隆(rimsulfuron))、三嗪类(例如莠去津(atrazine)和西玛津(simazine))、三唑啉酮类(例如氨唑草酮(amicarbazone))和吡啶羧酸类(例如定草酯(triclopyr))。
本发明的合适杀虫剂的实例包括新烟碱类(例如噻虫嗪(thiamethoxam)、噻虫胺(clothianidin)、噻虫啉(thiacloprid)、呋虫胺(dinotefuran)、吡虫清(acetamiprid)、硝胺烯啶(nitenpyram)、吡虫啉(Imidacloprid))、脒(例如虫螨脒(amitraz))、有机磷酸盐(例如毒死蜱(chlorpyrifos))和拟除虫菊酯类(例如氯菊酯(permethrin)、氟氯菊酯(bifenthrin)、溴氰菊酯(deltamethrin))。
关于上述农药和植物生长调节剂各自的详细描述，参考手册，例如CPC Publications Ltd，Alton，Hampshire的“The e-Pesticide Manual v4.0”(ISBN1901396428))。
本发明配制剂包含至少一种式(I)酰胺：
其中：
R1选自具有1-16个碳原子的非芳族烃基和苄基；
R2选自具有1-4个碳原子的烃基和苄基；且
R3选自氢和具有1-16个碳原子的烃基。
优选，当R1为具有1-4个碳原子的烃基或苄基时，则R3为具有5-16个碳原子的非芳族烃基。
优选，当R1为具有5-16个碳原子的烃基时，则R3为氢、甲基或乙基。
在本发明实施方案中，R1和R2独立地甲基或乙基，优选甲基，且R3为烃基，优选具有6-12个碳原子，优选7-10个碳原子的直链或支化烷基或链烯基。实例包括N,N-二甲基癸酰胺和N,N-二甲基辛酰胺。
这类酰胺是已知且市售的，或者可通过使合适有机酸和胺根据本领域熟知的方法反应而制备。
在本发明实施方案中，在式(I)酰胺中，R1为具有6-12，优选8-11个碳原子的烃基，优选直链或支化烷基或链烯基，R2为甲基、乙基或苄基，优选甲基，且R3为氢、甲基或乙基，优选氢。实例包括N-甲基-N-(2-丙基庚基)-甲酰胺、N-甲基-N-(2-丙基庚基)-乙酰胺、N-甲基-N-(正癸基)-乙酰胺、N-甲基-N-(正癸基)-甲酰胺、N-甲基-N-(单甲基取代的C9-10烷基)-乙酰胺和N-甲基-N-(单甲基取代的C9-10烷基)-甲酰胺。
这类酰胺是已知且市售的，或者可根据已知的方法，例如如WO2011/080208A1，Akzo Nobel Chemicals International B.V所述方法合成。
预期用于本发明配制剂中的酰基吗啉包括4-甲酰基吗啉(R＝H，也称为N-甲酰基吗啉或NFM)、4-乙酰基吗啉(R＝CH3，也称为N-乙酰基吗啉或NAM)、4-丙酰基吗啉(R＝C2H5，也称为N-丙酰基吗啉或NPM)及其混合物，优选本发明配制剂包含4-甲酰基吗啉，更优选4-甲酰基吗啉代表存在于配制剂中的式(II)酰基吗啉的至少50重量％，最优选至少90重量％，例如100重量％。然而，对于包含农药N,N’-双-[(1-甲酰氨基-2,2,2-三氯)乙基]哌嗪的配制剂，优选酰基吗啉选自4-乙酰基吗啉和4-丙酰基吗啉。
酰基吗啉本身是熟知的化合物且由标准化学供应商市购。
不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂，本文中称为“极性非质子溶剂”，可包含在本发明配制剂中。
极性非质子溶剂优选选自具有如根据ASTM D93所测量至少65℃的闪点的那些极性非质子溶剂。
极性非质子溶剂优选选自亚砜、酰胺、烃基-或亚烃基碳酸酯及其两种或更多种的混合物。优选的亚砜包括二甲亚砜。优选的碳酸烃基酯包括碳酸二烷基酯，例如具有C1-C8烷基链的那些。优选的碳酸亚烃基酯包括碳酸亚烷基酯，更优选碳酸C2-C4亚烷基酯，最优选碳酸亚丙酯。更优选，极性非质子助溶剂选自二甲亚砜、碳酸亚丙酯及其混合物，最优选碳酸亚丙酯。
其它组分可存在于本发明配制剂中。这类其它组分的实例包括一种或多种辅助剂，例如提高农业活性物质的生物效力的生物效力增强剂、保湿剂、润湿剂、流变改进剂、表面活性剂、乳化剂、粘着剂、漂移节制剂和/或常用于农业组合物中的其它组分。
水不预期用作以上“其它组分”中的一员。本发明配制剂可以为完全或基本无水配制剂，例如包含少于10重量％，优选少于1重量％水，或者可以为通常包含基于本发明配制剂的总重量至少90重量％，例如至少99重量％水的含水配制剂，例如乳液，通常水包油乳液。
本发明配制剂中的该一种或多种农业活性成分的浓度通常在具体化合物在具体溶剂体系中的溶解度范围内。
本发明配制剂中农业活性成分的浓度基于本发明无水配制剂的总体积通常为从约0.1g/l，例如从约10g/l，例如从约20g/l，至约950g/l，例如至约500g/l，例如至约300g/l。
在本发明的典型配制剂中，该组合物中至少一种农业活性成分的浓度为50-250g/l。
本发明配制剂中式(I)酰胺的浓度基于本发明无水配制剂的总体积通常为从25g/l，例如从50g/l，例如从100g/l，至900g/l，例如至700g/l，例如至500g/l。
当存在极性非质子溶剂时，式(II)酰基吗啉与极性非质子溶剂的重量比为从5:95、从30:70、从50:50、从70:30或从75:25，至95:5、至90:10或至85:15。例如，式(II)酰基吗啉与极性非质子溶剂的重量比可以为约80:20。
本发明配制剂可基于本发明无水配制剂的总体积包含总共为从约10g/l，例如从50g/l，例如从100g/l，至约600g/l，例如至约400g/l，例如至约250g/l的c)式(II)酰基吗啉和如果存在的话d)极性非质子助溶剂。
如果存在的话，本发明配制剂中其它组分的浓度基于本发明无水配制剂的总体积通常为从10g/l，例如从20g/l，例如从50g/l，至250g/l，例如至150g/l，例如至100g/l。
本发明配制剂可以以这种方式制备以致将组分以所需比和所需浓度相互混合。通常，配制剂在10-50℃的温度下制备。用于制备农业配制剂的合适设备适用作制备本发明配制剂的设备。
本发明组合物可以为包含如本文所定义的配制剂，包括乳化剂的可乳化浓缩组合物，在下文和本领域中通常称为“可乳化浓缩物”或“EC”。因此，这类可乳化浓缩物包含农业活性成分、式(I)酰胺、式(II)酰基吗啉、任选极性非质子助溶剂和乳化剂。
在可乳化浓缩物中，农业活性成分的浓度对最终使用而言通常太高，并意欲将可乳化浓缩物用含水介质稀释成工作组合物。
本发明可乳化浓缩物优选包含形成水包油乳液的量以下的量的水。优选可乳化浓缩物包含基于可乳化浓缩物的总重量少于约10重量％，更优选少于约1重量％水。最优选，本发明可乳化浓缩物基本不含水，意味着可乳化浓缩物不包含超过与周围氛围平衡不可避免的水的水。
预期用于本发明中的乳化剂包括本领域技术人员称为乳化剂的表面活性剂，例如阴离子表面活性剂、非离子表面活性剂、聚合物及其两种或更多种的混合物，尤其是包含阴离子和非离子表面活性剂的混合物。
预期用作本发明中的乳化剂的非离子表面活性剂的实例包括优选包含8-22个碳原子的烷氧基化，优选乙氧基化和/或丙氧基化醇；烷基(聚)糖苷，例如直链或支化C4-C10烷基(聚)糖苷；烷氧基化，优选乙氧基化脱水山梨糖醇或山梨糖醇酯；蓖麻油乙氧基化物；和三苯乙烯基苯酚烷氧基化物。
优选的乙氧基化醇具有1-50，更优选2-20，最优选3-10的乙氧基化度。预期用于本发明中的一些烷氧基化醇的实例包括基于如下醇的那些：支化醇，例如格尔伯特醇，例如2-丙基庚醇和2-乙基己醇，和C10或C13羰基合成醇，即其主要组分由至少一种支化C10或C13醇形成的醇混合物，和作为Exxal醇由Exxon Mobile Chemicals以及作为Neodol醇由ShellChemicals市购的醇。
预期用作本发明中的乳化剂的阴离子表面活性剂的实例包括磺基琥珀酸酯，烷基苯磺酸盐，例如十二烷基苯磺酸钙或钠，烷基磺酸酯，烷基醚硫酸酯，任选烷氧基化，优选乙氧基化和/或丙氧基化的磷酸酯，醇，二甲苯和异丙苯磺酸盐，和可缩合的萘或烷基萘磺酸酯，或其组合。
单独或组合用作乳化剂的聚合物的实例包括氧化乙烯-氧化丙烯嵌段共聚物、丙烯酸基梳型聚合物和黄原胶。
在本发明可乳化浓缩物中，乳化剂的浓度基于本发明无水配制剂的总体积通常为从10g/l，例如从50g/l，至200g/l，例如至150g/l。
本发明还涉及含水，通常水包油乳液，其包括含水介质、至少一种优选具有低水溶性的农业活性成分、式(I)酰胺、式(II)酰基吗啉、乳化剂以及任选极性非质子溶剂和/或其它组分。
例如，该乳液可通过将含水介质与如本文先前所定义的可乳化浓缩物混合，或者将组分单独地混合而得到。
如本文所用，术语“乳液”应当理解包括大乳液、纳米乳液、微乳液和悬乳液，即微粒固体悬浮于其中的乳液。
为本发明乳液的组分的含水介质通常包含水作为主要组分。优选水构成至少50重量％，例如至少75重量％，例如至少90重量％的含水介质。含水介质可进一步包含其它组分，例如盐、缓冲剂、pH调节剂如酸或碱、肥料等。
当将可乳化浓缩物与含水介质混合时，形成乳液，乳液通常为由最终使用者使用的工作组合物，其优点是最终使用者不需要处理和储存大量工作组合物，而是可现场制备需要的量。
本发明乳液通常通过将本发明可乳化浓缩物与含水介质以从约1:25，优选从约1:50，更优选从约1:100；至约1:1000，优选至约1:500，更优选至约1:300的可乳化浓缩物:含水介质体积比混合而制备。在典型的本发明乳液中，可乳化浓缩物:含水介质体积比为约1:200。
本发明的优点是在配制剂为浓缩形式，即包含少于10重量％水，优选少于1重量％水时，农业活性成分显示出较低或者不显示沉淀或结晶倾向。
本发明的另一优点是甚至在乳液的高稀释下，即在配制剂与含水介质之间的低比值下，农业活性成分沉淀或结晶的倾向是低的，在明显低于室温的温度下，例如在5℃下也是如此。由于许多原因，这是有利的。如果最终使用者在整批乳液用完以前必须停止喷晒，即使该未用完之乳液储存在低温下，该未用完乳液仍有可能在以后，例如隔天使用。
在另一方面中，本发明提供处理植物或种子的方法，其中使植物或种子与本发明配制剂接触。通过该方法与植物或种子接触的农业活性成分的所需量取决于几个参数，例如农业活性物的生物活性，但一般而言，应将量调整至足使该农业活性成分执行其所需活性的用量。
如本文所使用，“植物”包括植物的所有部分，包括根、茎、叶、花和果实。
在处理方法的一个实施方案中，通过喷雾使植物或种子与本发明配制剂，通常水包油乳液接触。
在处理方法的另一实施方案中，通过将植物或种子浸渍或浸泡在配制剂中而使植物或种子，通常种子与本发明配制剂接触。
实验
实验1
为得到表1-3中所公开的配制剂，将农业活性成分(AI)连同N-甲酰基吗啉(NFM)、碳酸亚丙酯(PC)和乳化剂一起加入量瓶中至所述量。然后加入N,N-二甲基癸酰胺或N-癸基-N-甲基甲酰胺使得总混合物合计为1L。乳化剂为5:3重量:重量比的每摩尔醇用35摩尔氧化丙烯和32摩尔氧化乙烯来烷氧基化的2-乙基己醇(2EH+35PO+32EO)和十二烷基苯磺酸钙。
将混合物用磁力搅拌器搅拌直至活性物质溶于配制剂中。将最终配制剂放入0℃的冷冻机中7天。
肉眼判断所有配制剂在储存以后是否包含任何晶体。各配制剂的组成和结果显示于下表1-3中。
表1
*对比实验
表2
*对比实验
表3
| 配制剂 | 农药 | 乳化剂 | NFM | PC | N,N-二甲基癸酰胺 | 形成晶体 |
| 14* | 350g/l氰氟草酯 | 65g/l | 0 | 0 | 至1L | 是 |
| 15 | 350g/l氰氟草酯 | 65g/l | 80 | 20 | 至1L | 否 |
| 16 | 350g/l氰氟草酯 | 65g/l | 60 | 40 | 至1L | 否 |
*对比实验
从结果中看，显然酰基吗啉和任选极性非质子溶剂包含在酰胺溶剂中减少晶体的形成，且省去酰基吗啉不会得到满意的结果。
实验2—乳液稀释
将包含100g/l的腈苯唑(fenbuconazole)的配制剂与65g/l的表面活性剂混合物(47重量％聚氧化丙烯聚氧化乙烯嵌段共聚物，56PO/60EO，20重量％十二烷基苯磺酸盐，33重量％HD油醇(60/65)乙氧基化物，23EO)一起配制并如下稀释：
1)N-甲酰基吗啉：碳酸亚丙酯(重量比4:1)，至1升
2)N-甲酰基吗啉：碳酸亚丙酯(重量比4:1)，100g/l并用N,N二甲基癸酰胺ND稀释至1升
将各配制剂在环境温度(～22℃)下以体积比(配制剂:水)5ml:95ml稀释在水中乳化(342ppm CaCO3-当量)。将乳液倒入100ml玻璃试管中并通过测量2小时以后试管中可见的乳油/油/沉降体积而评估稳定性。通过用肉眼目测检查判断外观，结果可见于表4。
表4
| 配制剂 | 2小时以后的外观 |
| 17* | 5ml油 |
| 18 | 没有乳油/油或沉淀 |
*对比实验
Claims (27)
1.一种配制剂，其包含：
a)至少一种农业活性成分；
b)至少一种式(I)酰胺：
其中：
R1选自具有1-16个碳原子的非芳族烃基和苄基；
R2选自具有1-4个碳原子的烃基和苄基；且
R3选自氢和具有1-16个碳原子的烃基，
其中当R1为具有1-4个碳原子的非芳族烃基或苄基时，则R3为具有5-16个碳原子的非芳族烃基，且当R1为具有5-16个碳原子的非芳族烃基时，则R3为氢、甲基或乙基；
c)至少一种式(II)酰基吗啉：
其中R为H、CH3或C2H5。
2.根据权利要求1的配制剂，其中所述农业活性成分选自农药和植物生长调节剂。
3.根据权利要求1或2的配制剂，其中所述农业活性成分选自三唑类、嗜球果伞素类、亚烷基双(二硫代氨基甲酸酯)化合物类、苯并咪唑类、苯氧基羧酸类、苯甲酸类、磺酰脲类、三嗪类、吡啶羧酸类、新烟碱类、脒类、有机磷酸酯类、拟除虫菊酯类及其混合物。
4.根据权利要求1的配制剂，其中R1和R2独立地为甲基或乙基，且R3为具有6-12个碳原子的烃基。
5.根据权利要求1的配制剂，其中R1为具有8-12个碳原子的非芳族烃基，R2为甲基、乙基或苄基，且R3为氢、甲基或乙基。
6.根据权利要求1或2的配制剂，其进一步包含d)至少一种不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂。
7.根据权利要求6的配制剂，其中所述不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂选自亚砜、酰胺、碳酸烃基酯、碳酸亚烃基酯及其混合物。
8.根据权利要求1、2或7的配制剂，其包含为N-甲酰基吗啉的式(II)酰基吗啉和为碳酸亚丙酯的不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂。
9.根据权利要求6的配制剂，其包含为N-甲酰基吗啉的式(II)酰基吗啉和为碳酸亚丙酯的不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂。
10.根据权利要求6的配制剂，其中式(II)酰基吗啉与不同于式(II)酰基吗啉的极性非质子溶剂之间的重量比为70:30-90:10。
11.根据权利要求7或9的配制剂，其中式(II)酰基吗啉与不同于式(II)酰基吗啉的极性非质子溶剂之间的重量比为70:30-90:10。
12.根据权利要求8的配制剂，其中式(II)酰基吗啉与不同于式(II)酰基吗啉的极性非质子溶剂之间的重量比为70:30-90:10。
13.根据权利要求1或2的配制剂，其进一步包含e)至少一种选自辅助剂的其它组分。
14.根据权利要求7的配制剂，其进一步包含e)至少一种选自辅助剂的其它组分。
15.根据权利要求1或2的配制剂，其进一步包含e)至少一种选自表面活性剂、乳化剂、润湿剂、流变改进剂及其两种或更多种的混合物的其它组分。
16.根据权利要求7的配制剂，其进一步包含e)至少一种选自表面活性剂、乳化剂、润湿剂、流变改进剂及其两种或更多种的混合物的其它组分。
17.根据权利要求6的配制剂，其进一步包含e)至少一种选自辅助剂的其它组分。
18.根据权利要求6的配制剂，其进一步包含e)至少一种选自表面活性剂、乳化剂、润湿剂、流变改进剂及其两种或更多种的混合物的其它组分。
19.根据权利要求14、16、17或18的配制剂，其基于无水配制剂的总体积包含：
10-800g/l的a)；
50-900g/l的b)；
总共为10-600g/l的c)和d)；和
0-250g/l的e)。
20.根据权利要求13的配制剂，其基于无水配制剂的总体积包含10-200g/l的乳化剂。
21.根据权利要求14的配制剂，其基于无水配制剂的总体积包含10-200g/l的乳化剂。
22.根据权利要求17或18的配制剂，其基于无水配制剂的总体积包含10-200g/l的乳化剂。
23.根据权利要求19的配制剂，其基于无水配制剂的总体积包含10-200g/l的乳化剂。
24.根据权利要求1或2的配制剂，其基于配制剂的总重量包含至多10重量％水。
25.根据权利要求1或2的配制剂，其呈基于配制剂的总重量包含至少90重量％水的水包油乳液的形式。
26.处理植物或种子的方法，其包括使所述植物或种子与根据权利要求1-25中任一项的配制剂接触。
27.溶剂体系作为农业活性成分的溶剂的用途，所述溶剂体系包含：(i)至少一种式(I)酰胺：
其中：
R1选自具有1-16个碳原子的非芳族烃基和苄基；
R2选自具有1-4个碳原子的烃基和苄基；且
R3选自氢和具有1-16个碳原子的烃基，
条件是：
当R1为具有1-4个碳原子的非芳族烃基或苄基时，则R3为具有5-16个碳原子的非芳族烃基，且当R1为具有5-16个碳原子的非芳族烃基时，则R3为氢、甲基或乙基；
(ii)式(II)酰基吗啉：
其中R为H、CH3或C2H5，
(iii)任选不同于式(I)酰胺和式(II)酰基吗啉的极性非质子溶剂；和
(iv)任选其它组分。
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| Application Number | Priority Date | Filing Date | Title |
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| EP11190506.3 | 2011-11-24 | ||
| EP11190506 | 2011-11-24 | ||
| US201161563970P | 2011-11-28 | 2011-11-28 | |
| US61/563,970 | 2011-11-28 | ||
| PCT/EP2012/073368 WO2013076200A1 (en) | 2011-11-24 | 2012-11-22 | Agricultural formulations with amides and acyl morpholines |
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| EP (1) | EP2782444B1 (zh) |
| JP (1) | JP2014533712A (zh) |
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| PL (1) | PL2782444T3 (zh) |
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| WO2024018453A1 (en) * | 2022-07-21 | 2024-01-25 | Adama Makhteshim Ltd. | Compositions of triazole fungicides |
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| WO2011080208A1 (en) * | 2009-12-30 | 2011-07-07 | Akzo Nobel Chemicals International B.V. | Amides, use of amides as solvents for organic compounds, compositions and emulsions containing amides, and method for treating a plant |
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| DE19623291A1 (de) | 1996-06-11 | 1997-12-18 | Basf Ag | Verfahren zur Herstellung von schwefelarmen aliphatischen Verbindungen |
| DE102005055739A1 (de) * | 2005-11-23 | 2007-05-24 | Clariant Produkte (Deutschland) Gmbh | Agrochemische Zusammensetzung |
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| ES2581805T3 (es) * | 2010-05-27 | 2016-09-07 | Akzo Nobel Chemicals International B.V. | Formulaciones agrícolas con acilmorfolinas y codisolvenes apróticos polares |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1299044A (en) * | 1970-07-03 | 1972-12-06 | Boehringer Sohn Ingelheim | Method of pest control |
| US4452630A (en) * | 1979-07-27 | 1984-06-05 | Montedison S.P.A. | Stable, heat-resistant solutions of pesticidal carbamates |
| CN101453897A (zh) * | 2006-05-26 | 2009-06-10 | 胡茨曼石油化学公司 | 用于农业化学品的低气味、低挥发性溶剂 |
| CN101616580A (zh) * | 2007-02-22 | 2009-12-30 | 考格尼斯知识产权管理有限责任公司 | 包含基于羟基羧酸的二烷基酰胺的杀生物剂组合物 |
| WO2011080208A1 (en) * | 2009-12-30 | 2011-07-07 | Akzo Nobel Chemicals International B.V. | Amides, use of amides as solvents for organic compounds, compositions and emulsions containing amides, and method for treating a plant |
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| Publication number | Publication date |
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| AU2012342488B2 (en) | 2015-08-13 |
| ZA201403715B (en) | 2015-08-26 |
| UA112454C2 (uk) | 2016-09-12 |
| CN103945691A (zh) | 2014-07-23 |
| AU2012342488A1 (en) | 2014-05-01 |
| NZ623848A (en) | 2015-11-27 |
| EP2782444A1 (en) | 2014-10-01 |
| RU2606800C2 (ru) | 2017-01-10 |
| IN2014DN03142A (zh) | 2015-05-22 |
| WO2013076200A1 (en) | 2013-05-30 |
| RU2014124360A (ru) | 2015-12-27 |
| ES2632586T3 (es) | 2017-09-14 |
| US20140315718A1 (en) | 2014-10-23 |
| JP2014533712A (ja) | 2014-12-15 |
| US10750740B2 (en) | 2020-08-25 |
| EP2782444B1 (en) | 2017-04-19 |
| BR112014011294A2 (pt) | 2017-05-02 |
| PL2782444T3 (pl) | 2017-09-29 |
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