CN1043601A - 低挥发性的盐 - Google Patents

低挥发性的盐 Download PDF

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CN1043601A
CN1043601A CN89109797A CN89109797A CN1043601A CN 1043601 A CN1043601 A CN 1043601A CN 89109797 A CN89109797 A CN 89109797A CN 89109797 A CN89109797 A CN 89109797A CN 1043601 A CN1043601 A CN 1043601A
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约翰尼·李·贝恩斯
理查德·汉塞尔·威尔逊
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Abstract

以胺盐形式存在的农药活性化合物与游离酸形式和其它盐形式存在的农药活性化合物比较，降低了挥发性。

Description

本发明涉及应用几种盐降低生物活性化合物的挥发性。更具体的说，本发明涉及特定盐形态的农药活性化合物，它与游离酸形和其它盐形的农药活性化合物相比降低了挥发性。
根据本发明发现，某些胺以不同的数量在降低农药活性化合物挥发性上有特殊的作用，这些农药活性化合物如除草的，杀虫的和杀菌的活性化合物，它们有一个羧酸基团，这些胺通过简单地加合到其它盐形上可以用于这种降低挥发性的目的。
由于农药的飘移不仅危害敏感的非靶标生物，而且对靶标生物减弱了作用，因此需要低挥发性的农药。
现已发现选自下述的各组胺
a）式Ⅰ表示的氨基丙基吗啉（APM）
b）式Ⅱ表示的Jeff胺D-230
Figure 89109797X_IMG12
其中n是2或3;
c）式Ⅲ表示的甲基二乙醇胺（MDEA）
CH3-N-（CH2-CH2-OH）2Ⅲ;
d）式Ⅳ表示的2-氨基-2-乙基-1，3-丙二醇（AEPD）
Figure 89109797X_IMG13
e）式Ⅴ表示的三（羟甲基）氨基甲烷（Tris    Amino）
Figure 89109797X_IMG14
f）式Ⅵ表示的2，4，6-三（二甲基氨基甲基）苯酚
（Actiron    NX-3）和氢氧化钠
能够显著地降低农药活性化合物的挥发性而对其农药活性没有不利的影响。因此，本发明一方面是提供通过上述胺盐形的农药活性化合物，并且还包括这些化合物的混合物。
根据本发明，降低挥发性的优选的除草化合物种类是含有羧酸的化合物，它包括草甘膦，苯甲酸类化合物，苯氧羧酸类化合物及其它们的混合物。特别优选的化合物包括二甲四氯（2-甲基-4-氯苯氧乙酸），麦草畏（3，6-二氯-2-甲氧基苯甲酸）和2，4-滴（2，4-二氯苯氧乙酸）。一种特别优选的实例是麦草畏和2，4-滴的APM盐及其它们的混合物。此外，特别引人注目的除草剂的羧酸是草甘膦（膦酰-甲基甘氨酸）。
转化成胺盐形的可以例举的具体杀菌剂包括多果定（N-十二烷基胍乙酸酯）和吗菌灵（吗菌灵乙酸酯）。
把前述任意的式Ⅰ到式Ⅵ的胺与一种农药活性化合物化合可以制得本发明的胺盐，该农药活性化合物是一种除草的、杀虫的或杀菌的活性化合物，它可以是纯的或者是含有该化合物的有效制剂。制剂可以是干燥的或固体的剂型，还可以是液剂，如水剂。另外，式Ⅰ到式Ⅵ的胺可以加到已经以其它盐形存在的农药活性化合物上。上述制备反应最好在水介质中进行。例如，在任何适宜的温度，如室温下，在一种水溶液中，一种式Ⅰ到式Ⅵ的胺可以加到二甲胺（DMA）盐形的麦草畏上（从Sandoz植保公司可得到商标为BANVELR的商品）。同样地，该式Ⅰ到式Ⅵ的胺及一种不同的成盐碱可与农药的游离酸形化合。在这两种情况中，它表明较少量的式Ⅰ到式Ⅵ的胺，在所得的混合物中降低农药的挥发性是有效的。上述这种化合作用可以方便地用于降低价格较贵的式Ⅰ到式Ⅵ的胺的用量同时保持了农药的整个盐制剂和低挥发性。
加入的式Ⅰ到式Ⅵ胺的量可以随所需要中和酸的用量变化，或者可以过量。式Ⅰ到式Ⅵ胺的量可以参照使农药的一种水溶液PH为8来表示。例如如果一个组合物是“1.5X”，那么它必须要有1.5倍的式Ⅰ到式Ⅵ的胺升高PH到8。根据本发明，组合物一般含0.1X，优选的范围是0.1到3X的式Ⅰ到式Ⅴ的化合物，较好的是0.5到2.5X，最好需要0.5到1.5X的式Ⅰ到式Ⅵ的胺。
如同该母体化合物与一种式Ⅰ到式Ⅵ的一种胺结合前所使用的那样，采用相同的方式和基本上相同的剂量可以施用本发明的化合物并且把它们作为农药。在挥发性增加了该化合物实际效果的时候，它可以使用稍略低些的剂量。
本发明特别感兴趣的是在有效抑制杂草上使用的化合物。例如麦草畏、2，4-滴或者它们的混合物，通过本发明除草有效量的胺盐形施用于杂草作物或杂草生长地。
一般来讲，本发明胺盐的施用量取决于下述公知的因素，如特定的胺盐，在生长地中的主要作物，施药时间，施药的方式和药品的剂型，防除杂草时的各种条件如土壤、气候及其它因素。然而在一般情况下，施用本发明胺盐量的范围是0.05到10Kg/公顷，通常在杂草防除中它可得到满意的结果。一般的范围是0.05到2Kg/公顷，优选的是0.1到1Kg/公顷，根据需要可以重复施药。当在作物上使用时，施用量将不超过5Kg/公顷，通常范围是0.1到2Kg/公顷。
本发明另一方面涉及含有一种农药活性化合物胺盐的组合物，其中胺选自上述定义的式Ⅰ到Ⅵ的一组胺并且该胺盐与一种农用惰性载体混合，它即可以是浓缩形也可以是稀释形使用在农业上。浓缩物可以带有常用惰性载体和其它常用的助剂如湿润剂，粘结剂和其它助剂的固体形。该组合物较好的是液体形，最好是水作为惰性载体，这种水溶剂至少要有效地溶解本发明的农药和其它存在的化合物的盐或游离酸形，并且要溶解过量的式Ⅰ到式Ⅵ的胺及其任意的助剂，如湿润剂和其它助剂等，这种组合物中也可以包括其它的农药。
上述组合物可以含有按重量计算0.01%到99%的本发明的农药，按重量计算0到20%的农用表面活性剂和按重量计算1%到99.99%的惰性载体，有时需要表面活性剂对活性组分的高比例，这可以通过掺合到制剂中或者通过罐混得到。一般地，在施用的组合物中含有按重量计算0.01%到25%的本发明的农药。根据予定的用途和农药的物理性质，也可以采用稍高或稍低的含量。对于浓缩型的组合物一般在使用前需要稀释到按重量计算有2%到90%的活性组分，最好按重量计算有10%到80%的活性组分。
本发明化合物的组合物或制剂包括粉剂、粒剂、丸剂、浓悬剂、可湿性粉剂、乳油和其它剂型。它们可以通过常规的方法制备，例如把惰性载体与本发明的农药混合，更具体来说液体组合物通过混合各组分制得，固体微粒组合物通过混合，通常是研磨制得，悬浮液通过湿磨制得，粒剂和丸剂通过渗透或用农药包裹予先成形的粒状载体或通过聚集的方法制得。
例如，把滑石、粘土、硅石和其它的固体惰性载体与农药混合并研磨能够制备粉剂。把溶解在一种适当溶剂中的农药浸在或浸入成粒的硅镁土或蛭石载体上制备粒剂，通常粒剂大小在0.3-1.5毫米之间。把湿润剂混入浓缩的粉剂组合物能够制备可湿性的粉剂，该剂能分散在水中或油中制成任意所需浓度的农药。
此外，本发明的农药可制成微囊剂使用。
在组合物中可以使用农业上适用的添加剂，用以改善农药的性能并且减少发泡，结块和侵蚀。
在此所用的表面活性剂意思是能够乳化、展着、湿润、分散或其它改进表面性质的农业上适用的物质。这样的表面活性剂例子为木质素磺酸钠和十二烷基硫酸钠。
在此所用的载体意为把浓缩物稀释到一种合用的或所需浓度的液体或固体物质。对于粉剂或粒剂的载体可以是滑石、高岭土或硅藻土，对于液体浓缩物的载体可以是如二甲苯的烃或如异丙醇的醇，对于液体施用的载体可以是水或柴油。
施用的组合物也可以包括其它有生物活性的化合物，例如，有相似活性或互补活性的化合物，或者是有解毒，除草，杀菌或杀虫活性的化合物。
通过以下实施例A、B和C来说明本发明的有代表性的农药组合物。在这些实施例中的量是以重量份数计算的。
实施例A
粉剂的制备
10份本发明的胺盐和90份滑石粉在一个机械研磨机中混合并研磨至均匀，得到所需粒剂的自由飘移的粉剂。这种粉剂适于直接施用在杂草蔓延地。
实施例B
可湿性粉剂的制备
25份本发明的胺盐和25份人工合成的二氧化硅粉，2份十二烷基硫酸钠，3份木质素磺酸钠和45份细粉状的高岭土混合，研磨，直至颗粒平均粒径为5微米。对于制得的可湿性粉剂，在使用前用水稀释，使得喷施药液为所需的浓度。
实施例C
乳油（EC）的制备
13.37份本发明的胺盐和1.43份Toximul    360A（含有较多量阴离子表面活性剂的阴离子和非离子表面活性剂的混合物），5.61份Toximul    360A（含有较多量阴离子表面活性剂的阴离子和非离子表面活性剂的混合物），23.79份的二甲基甲酰胺和55.8份的Tenneco    500-100（主要是烷基化的芳香烃的混合物，如二甲苯和乙苯的混合物）在一个烧杯里混合直至生成溶液。在使用时用水稀释所得的乳油。
参照下述非限定性的实施例，可以较好地阐明本发明。所有的实施例中BANVELR一词意为麦草畏-DMA。
实施例1
组合物
把已知量的麦草畏和/或2.4-滴悬浮于已知量的蒸馏水中制备每种化合物的制剂。用碱滴定，使PH达到最小值为8.0，记录所加入碱的量。然后加入蒸馏水使所需活性组分调到适当的浓度。有代表性的剂型给出如下。
Ⅰ.2.4-滴-DMA    439g/l或3.71b/gal
W/W%
2.4-滴原药（95%    ae）    41.66
DMA（60%）    14.45
蒸馏水    43.89
100.00
Ⅱ.麦草畏-DMA    480g/l或4.01b/gal
W/W%
麦草畏原药（80%）    50.00
DMA（60%）    17.00
蒸馏水    33.00
100.00
Ⅲa.麦草畏-Tris    Amino    480g/l
W/W%
麦草畏原药（90.7%）    41.19
Tris    Amino    28.05
蒸馏水    30.76
100.00
Ⅲb.2.4-滴-Tris    Amino
W/W%
2.4-滴（100%）    25.00
Tris    Amino    13.70
蒸馏水    61.30
100.00
Ⅲc.麦草畏-2.4-滴-Tris    Amino
W/W%
2.4-滴（100%）    12.50
麦草畏（100%）    12.50
Tris    Amino    13.70
蒸馏水    41.95
100.00
Ⅲd.麦草畏-2.4-滴-DMA-Tris    Amino
W/W%
2.4-滴（100%）    12.50
麦草畏（100%）    12.50
DMA    5.09
Tris    Amino    13.07
蒸馏水    56.21
100.00
Ⅳa.麦草畏-Jeff胺D-230
W/W%
麦草畏原药（90.7%）    43.79
Jeff胺D-230    24.28
蒸馏水    31.93
100.00
Ⅳb.2.4-滴-Jeff胺
W/W%
2.4-滴（100%）    25.00
Jeff胺D-230    24.77
蒸馏水    50.23
100.00
Ⅳc.麦草畏-2.4-滴-Jeff胺
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
Jeff胺D-230    24.77
蒸馏水    50.23
100.00
Ⅳd.麦草畏-2.4-滴-DMA-Jeff胺
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
DMA（100%）    5.09
Jeff胺D-230    24.77
蒸馏水    45.24
100.00
Ⅴa.麦草畏-AEPD
W/W%
麦草畏原药（90.7%）    42.85
AEPD    29.09
蒸馏水    28.06
100.00
Ⅴb.2.4-滴-AEPD
W/W%
2.4-滴（100%）    25.00
AEPD    13.48
蒸馏水    61.52
100.00
Ⅴc.麦草畏-2.4滴-AEPD
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
AEPD    13.48
蒸馏水    61.52
100.00
Ⅴd.麦草畏-2.4-滴-DMA-AEPD
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
DMA（100%）    5.09
AEPD    13.48
蒸馏水    56.43
100.00
Ⅵa.麦草畏-Actiron    NX-3
W/W%
麦草畏（原药）（89.6%）    33.87
Actiron    NX-3    7.67
NaOH（50%）    7.87
蒸馏水    50.65
100.00
Ⅵb.2.4-滴-Actiron    NX-3
W/W%
2.4-滴（100%）    25.00
Actiron    NX-3    7.78
NaOH（50%）    4.52
蒸馏水    62.70
100.00
Ⅵc.麦草畏-2.4-滴-Actiron    NX-3
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
Actiron    NX-3    7.78
NaOH（50%）    4.52
蒸馏水    62.70
100.00
Ⅵd.麦草畏-2.4-滴-DMA-Actiron    NX-3
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
DMA    5.09
Actiron    NX-3    15.56
蒸馏水    54.35
100.00
Ⅶa.麦草畏-MDEA
W/W%
麦草畏原药（89.6%）    23.97
MDEA    14.41
蒸馏水    61.62
100.00
Ⅶb.2.4-滴-MDEA
W/W%
2.4-滴（100%）    25.00
MDEA    13.48
蒸馏水    61.52
100.00
Ⅶc.麦草畏-2.4-滴-MDEA
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
MDEA    13.48
蒸馏水    61.52
100.00
Ⅶd.麦草畏-2.4-滴-DMA-MDEA
W/W%
麦草畏（100%）    12.50
2.4-滴（100%）    12.50
DMA    5.09
MDEA    13.48
蒸馏水    56.43
100.00
Ⅷa.2.4-滴-APM    230g/L或1.91b/gal
W/W%
2.4-滴原药（95%）    21.82
APM    19.41
蒸馏水    58.77
100.00
Ⅷb.麦草畏-APM480g/L或41b/gal
W/W%
麦草畏原药（90.7%）    43.42
APM    14.17
蒸馏水    42.41
100.00
Ⅷc.麦草畏-APM    196g/L或1.63lb/gal
W/W%
麦草畏原药（90.7%）    19.67
APM    18.64
蒸馏水    61.69
100.00
Ⅷd.麦草畏+2.4-滴-APM（1∶1比）APM
麦草畏120g/L或1lb/gal
2.4-滴120g/L或1lb/gal
W/W%
麦草畏原药（88%）    11.70
2.4-滴原药（95%）    10.88
2.4滴原药（95%）
APM    20.16
蒸馏水    57.29
100.00
Ⅷe.麦草畏+2.4-滴-APM（1∶2比）APM
麦草畏55.2g/L或0.46lb/gal
2.4-滴110.4g/L或0.92lb/gal
W/W%
麦草畏原药（88%）    5.84
2.4-滴原药（95%）    10.85
APM    15.12
蒸馏水    68.19
100.00
Ⅷf.BANVELR除草剂+APM
麦草畏440g/L或3.67lb/gal
W/W%
麦草畏（83%）    42.63
DMA（100%）    10.61
APM    11.55
蒸馏水    35.21
100.00
Ⅷg.BANVELR除草剂+APM
麦草畏333g/L或2.8lb/gal
W/W%
麦草畏（83%）    34.63
DMA（100%）    8.62
APM    28.16
蒸馏水    28.59
100.00
实施例2
挥发性研究实验
测定实施例1中组合物挥发性的降低并且把它与工业品的麦草畏进行比较。以下的每个值都是以一个陪替氏盘上根据量度C14的损失所测定的半衰期。
麦草畏的盐制剂    半衰期（小时）    挥发性降低倍数
麦草畏原药    36    ××××
Tris    Amino    4101    114
AEPD    6277    174
MDEA    6111    170
Actiron    NX-3    未测量挥发性
实施例3
田间挥发性研究试验
本实施例和以下的实施例中，小区的面积用原始测量数据计算，用英亩和磅表示，参考以下变换系数：1公顷＝2.47英亩;1千克＝2.2磅;1米＝3.28英尺;1磅/英寸2＝0.07千克/平方厘米;1加仑＝3.78升。
在面积为0.04公顷小区普通狗牙根牧地上测定除草剂的挥发性。使用一个CO2动力的背负喷雾器和有8个等间距8004扁平扇形喷嘴，以2.0kg/cm2压力和每公顷243升水，每英亩施用除草剂0.45kg。
把三台Gilian式HFO-113A空气泵等距离顺风方向放在小区中央，喷雾完成三分钟后，间隔八小时。使用含有SKC-227-7过滤垫的塑料盒，以每分钟2.6升的量收集空气样品，并且用标准的气相色谱方法和Hall检测器分析除草剂的含量。检测限量为0.01μg/样品。所表示的结果是三次测量值的平均数。
这个实验在无雨的白天进行。温度是88°F，相对湿度68%。结果如下所示。
麦草畏的盐 降低的倍数＊
Tris    Amino    17X
AEDP    13X
Jeff胺    12X
Actiron    NX-3    6X
＊降低量与Banvel除草剂比较，本实验中所有的盐都滴定到PH为8.0。
实施例4
除了小区的面积变化为0.04到0.4公顷，每公顷施药量范围是1.1到2.2Kg的活性组分外，使用实施例3中描述的，对2.4滴和麦草畏-2.4滴制剂进行田间测定。温度变化范围是75到91°F，相对湿度是48-74%。结果如下表示。
施用剂量
除草剂    （kg活性组分/每公顷）    挥发性（μg）
2，4-滴-DMA    2.2    0.29
2，4-滴-APM    2.2    0.01
麦草畏-1.5X    DMA    1.1    1.13
麦草畏-1.5X    APM    1.1    0.024
BANVELR1.1 1.10
BANVELR+0.5X APM 1.1 0.08
BANVELR+1.4X APM 1.1 0.03
实施例5
加入氨基丙基吗啉（APM）对2，4-滴和麦草畏混合物的影响。
对下述制剂的评价采用的条件和实施例4相同。如下所示的结果是三次测定值的平均数。
Figure 89109797X_IMG16
实施例6
除草活性
测定了在麦田中防除各种杂草的各种剂型的药效。麦草畏-2，4-滴化合的各种盐以每公顷0.06，0.125和0.25kg麦草畏和每公顷0.38kg2，4-滴施用。
评价的杂草包括：
猪草（Pigweed）
马利筋（Milkweed）
油菜（Rape）
田芥菜（Charlock）
羽叶播娘蒿（Tansy    mustard）
播娘蒿（Tansy    mustard）
向日葵（Sunflower）
野莴苣（Wild    lettuce）
宝盖草（Henbit）
欧洲稻搓菜（Nipplewort）
蔓荞麦（Climbing    Buckwheat）
皱叶酸模（Yellow    dock）
俄罗斯蓟（Russian    thistle）
水芹（Field    Penny-Cress）
所有的剂型基本上如同DMA剂型给出同样的除草效果，表明各种盐都不影响活性。同时也评价了各种盐的药害量，各种盐不影响药害剂量。
实施例7
如同在实施例6中描述的那样，在玉米地上评价防除杂草和药害的剂量。评价的杂草包括：
绒毛叶（Velvet-leaf）
猪草（Pigweed）
藜（Lambs-quarters）
宾洲蓼（Pennsylvania    smartweed）
银叶龙葵（Silverleaf    nightshade）
普通苍耳（Common    cocklebur）
与DMA剂型比较，无论是在防除杂草上或在药害剂量上都没有明显的区别。
实施例8
如同在实施例6中描述的那样，在高梁地上评价防除杂草和药害的剂量。评价的杂草包括：
红根猪草（Redroot    pigweed）
纹孔牵牛花（Pitted    morningglory）
宾洲蓼（Pennsylvania    smartweed）
与DMA剂型比较，无论是在防除杂草上或在药害剂量上都没有明显的区别。

Claims (9)

1、一种农药组合物，包括一种农药活性化合物的胺盐和农业上适用的载体，其中该胺选自
a)式I表示的氨基丙基吗啉(APM)
Figure 89109797X_IMG1
b)式Ⅱ表示的Jeff胺D-230
(其中n是2或3)
c)式Ⅲ表示的甲基二乙醇胺(MDEA)
CH3-N-(CH2-CH2-OH)2Ⅲ；
d)式Ⅳ表示的2-氨基-2-乙基-1，3-丙二醇(AEPD)
Figure 89109797X_IMG3
e)式Ⅴ表示的三(羟甲基)氨基甲烷(TrisAmino)
Figure 89109797X_IMG4
和
f)式Ⅵ表示的2，4，6-三(二甲基氨基甲基)苯酚(ActironNX-3)和氢氧化钠
。
2、根据权利要求1的农药组合物具有除草活性。
3、根据权利要求1的农药组合物具有杀菌活性。
4、根据权利要求1的农药组合物具有杀虫活性。
5、根据权利要求1的农药组合物，其中农药活性化合物选自下述物质：麦草畏，2.4-滴，它们的盐，和它们的混合物。
6、根据权利要求1的农药组合物，其中农药活性化合物是麦草畏或它的一种盐。
7、根据权利要求1至6的农药组合物，其中的胺是APM。
8、一种制备权利要求1到7中的盐的方法，包括把一种农药活性化合物与选自下述成盐的胺化合：
（a）式Ⅰ表示的氨基丙基吗啉（APM）
（b）式Ⅱ表示的Jeff胺D-230
（其中n是2或3）
（c）式Ⅱ表示的甲基二乙醇胺（MDEA）
CH3-N-（CH2-CH2-OH）2Ⅲ;
（d）式Ⅳ表示的2-氨基-2-乙基-1，3-丙二醇（AEPD）
Figure 89109797X_IMG8
（e）式Ⅴ表示的三（羟甲基）氨基甲烷（Tris  Amino）
Figure 89109797X_IMG9
，和
（f）式Ⅵ表示的2，4，6-三（二甲基氨基甲基）苯酚（Actiron  NX-3）和氢氧化钠
Figure 89109797X_IMG10
9、一种防除杂草的方法，包括把一种除草有效量的权利要求2，5或6的胺盐施用到杂草生长地。
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