CN102595883A - 含有吡咯烷酮-4-羧酸衍生物的农药制剂 - Google Patents
含有吡咯烷酮-4-羧酸衍生物的农药制剂 Download PDFInfo
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- CN102595883A CN102595883A CN2010800427242A CN201080042724A CN102595883A CN 102595883 A CN102595883 A CN 102595883A CN 2010800427242 A CN2010800427242 A CN 2010800427242A CN 201080042724 A CN201080042724 A CN 201080042724A CN 102595883 A CN102595883 A CN 102595883A
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- substituted
- pyrrolidone
- carboxylic acid
- alkyl
- pesticidal preparations
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- LLEMOWNGBBNAJR-UHFFFAOYSA-N ortho-phenyl-phenol Natural products OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
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- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
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- 229940071207 sesquicarbonate Drugs 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
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- BJNLLBUOHPVGFT-QRZIFLFXSA-N teichomycin Chemical compound CCCCCCCCCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)OC=2C(=CC(=CC=2)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@H]2C(N[C@H](C3=CC(O)=CC(O[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=C3C=3C(O)=CC=C(C=3)[C@@H](NC3=O)C(=O)N2)C(O)=O)=O)Cl)=C(OC=2C(=CC(C[C@H](C(N4)=O)NC(=O)[C@H](N)C=5C=C(O6)C(O)=CC=5)=CC=2)Cl)C=C1[C@H]3NC(=O)[C@@H]4C1=CC6=CC(O)=C1 BJNLLBUOHPVGFT-QRZIFLFXSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及农药制剂,其含有一种或多种农药和一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物,并且涉及所述农药制剂用于防控和/或抗击杂草、真菌疾病或昆虫侵染的用途。N-取代的2-吡咯烷酮-4-羧酸衍生物作为所述农药制剂中的助剂、乳化剂、分散剂和/或润湿剂起作用。
Description
本发明涉及包含吡咯烷酮羧酸衍生物的农药制剂,和它们的用途,和尤其是用于防控和/或抗击杂草、真菌疾病或昆虫侵染的用途。
农药通常以制剂形式使用以实现活性化合物的更佳利用。所述制剂也描述为配制剂并一般以固体或液体形式存在。配制剂包含至少一种辅剂,但在绝大多数情况下包含具有各种功能的多种辅剂。
根据其功能,辅剂的实例是溶剂、乳化剂、润湿剂、分散剂、结晶抑制剂、消泡剂、防腐剂、抗氧化剂、增稠剂、防冻剂、保湿剂、着色剂和助剂。助剂应理解为意指增加活性化合物的生物学有效性而其本身并不显示任意生物学作用的辅剂,例如通过改善润湿、保留或植物或靶标有机体的吸收。
液体制剂(“配制剂类型”)的实例是水溶液(SL),浓悬浮剂(SC),悬乳剂(SE),乳油(EC),油分散剂(OD),水乳剂(EW)或微乳剂(ME)。
固体制剂(“配制剂类型”)的实例是水溶性粉剂或颗粒剂(SP,SG)或水可分散粉剂或颗粒剂(WP,WDP,WG,WDG)。
从毒理学或生态毒理学角度考虑,用于农药制剂中的许多有效辅剂都是不良的,比如壬基苯酚乙氧基化物(由于其内分泌作用),脂肪胺乙氧基化物(生态毒性特性)或N-甲基吡咯烷酮(繁殖毒性特性)。
相应地,对于农药制剂中新辅剂的一个要求是其为毒理学和生态毒理学无顾虑的。
农药制剂中的辅剂的另一重要基本要求是,它们对有用植物不产生有害效果(植物毒性)。这尤其是对于杀真菌剂、杀昆虫剂和选择性除草剂极为重要,但是,对于例如在耐受相应非选择性除草剂著称的转基因有用植物的情况下使用的非选择性除草剂也极为重要。
因此,本发明的目的是提供包含辅剂的农药制剂,其特征在于良好的效力、毒理学和生态毒理学无顾虑和低植物毒性。
令人惊讶地,目前发现该目的通过将N-取代的2-吡咯烷酮-4-羧酸衍生物用于农药制剂中得以实现,并且N-取代的2-吡咯烷酮-4-羧酸及其盐、酯和酰胺特别适宜用作农药制剂的有效辅剂。
因此,本发明提供农药制剂,其包含
a)一种或多种农药和
b)一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物。
在本发明的上下文中,“N-取代的2-吡咯烷酮-4-羧酸衍生物”应理解为意指N-取代的2-吡咯烷酮-4-羧酸和其它衍生物,比如尤其是所述N-取代的2-吡咯烷酮-4-羧酸的盐、酯和酰胺。
US 2,757,125描述N-烷基-4-羧基-2-吡咯烷酮及其盐、某些烷基酯和烷基酰胺,其用作化妆品配制剂或清洁组合物中的抗菌组分。
US 2,977,309描述润滑油,其包含衣康酸与具有10-24个碳原子的支化脂族伯胺的反应产品。
US 3,224,975描述包含N-烷基-4-羧基-2-吡咯烷酮的润滑剂组合物,其中所述烷基残基包含8-25个碳原子。
GB 1323061公开特定的N-取代的4-羧基-2-吡咯烷酮及其在功能流体比如液压流体中的用途。
EP 2 022 781描述二聚体N-烷基-4-羧基-2-吡咯烷酮衍生物,其通过羧基基团处的桥连接,及其它们作为气体水合物抑制剂的用途。
EP 2 028 247描述N-烷基-2-吡咯烷酮-4-羧酸酯作为气体水合物抑制剂的用途。
WO 2009/086872和WO 2009/086873描述N-烷基-2-吡咯烷酮-4-羧酸铵盐作为缓蚀剂的用途。
然而,吡咯烷酮羧酸衍生物作为农药配制剂中的辅剂的用途并未得到描述。
在本发明的上下文中,农药应理解为意指除草剂,杀真菌剂,杀昆虫剂,杀螨剂,杀菌剂,杀软体动物剂,杀线虫剂和杀啮齿类剂,以及植物激素。植物激素控制生理学反应比如生长、花期、细胞分裂和种子成熟。最有关农药的综述可参见例如British Crop ProtectionCouncil的“The Pesticide Manual”,14th Edition 2006,Editor:CDS Tomlin。
根据本发明的农药制剂的组分a)的一种或多种农药优选选自除草剂、杀昆虫剂和杀真菌剂。
优选的杀真菌剂是脂族氮类杀真菌剂,酰胺类杀真菌剂比如酰基氨基酸类杀真菌剂或酰基苯胺类杀真菌剂或苯甲酰胺类杀真菌剂或嗜球果伞素类类杀真菌剂(Strobilurinfungizide),芳族类杀真菌剂,苯并咪唑类杀真菌剂,苯并噻唑类杀真菌剂,氨基甲酸酯类杀真菌剂,康唑类杀真菌剂比如咪唑或三唑类,二甲酰亚胺类杀真菌剂,二硫代氨基甲酸酯类杀真菌剂,咪唑类杀真菌剂,吗啉类杀真菌剂,噁唑类杀真菌剂,吡唑类杀真菌剂,吡啶类杀真菌剂,嘧啶类杀真菌剂,吡咯类杀真菌剂,醌类杀真菌剂。
优选的除草剂是酰胺除草剂,N-酰基苯胺除草剂,芳族酸除草剂比如苯甲酸除草剂或皮考啉酸除草剂,苯甲酰基环己烷二酮除草剂,苯并呋喃基烷基磺酸盐/酯除草剂,苯并噻唑除草剂,氨基甲酸酯除草剂,苯氨基甲酸酯除草剂,环己烯肟除草剂,环丙基异噁唑除草剂,二甲酰亚胺除草剂,二硝基苯胺除草剂,二硝基酚除草剂,二苯醚除草剂,二硫代氨基甲酸酯除草剂,咪唑啉酮除草剂,腈除草剂,有机磷除草剂,噁二唑酮除草剂,噁唑除草剂,苯氧基除草剂比如苯氧基乙酸除草剂或苯氧基丁酸除草剂或苯氧基丙酸除草剂或芳氧基苯氧基丙酸除草剂,吡唑除草剂比如苯甲酰基吡唑除草剂或苯基吡唑除草剂,哒嗪酮除草剂,吡啶除草剂,硫代氨基甲酸酯除草剂,三嗪除草剂,三嗪酮除草剂,三唑除草剂,三唑酮除草剂,三唑并嘧啶除草剂,尿嘧啶除草剂,脲除草剂比如苯脲除草剂或磺酰脲除草剂。
优选的杀昆虫剂是氨基甲酸酯杀昆虫剂比如苯并呋喃基甲基氨基甲酸盐/酯杀昆虫剂或二甲基氨基甲酸盐/酯杀昆虫剂或肟氨基甲酸酯杀昆虫剂或苯基甲基氨基甲酸盐/酯杀昆虫剂,二酰胺杀昆虫剂,昆虫生长调节剂,大环内酯杀昆虫剂比如阿维菌素杀昆虫剂(Avermectin-Insektizide)或密比霉素杀昆虫剂(Milbemycin-Insektizide)或多杀霉素杀昆虫剂(Spinosyninsektizide),沙蚕毒素类似物杀昆虫剂,烟碱类杀昆虫剂比如硝基胍烟碱类杀昆虫剂或吡啶基甲胺烟碱类杀昆虫剂,有机磷杀昆虫剂或有机磷酸酯杀昆虫剂或有机硫代磷酸酯杀昆虫剂或膦酸酯杀昆虫剂或硫代酰基磷酸酯杀昆虫剂,噁二嗪杀昆虫剂,吡唑杀昆虫剂,拟除虫菊酯杀昆虫剂比如拟除虫菊酯酯杀昆虫剂或拟除虫菊酯醚杀昆虫剂或拟除虫菊酯肟杀昆虫剂,吡咯酮酸杀昆虫剂四氢呋喃二酮杀昆虫剂,噻唑杀昆虫剂。
特别优选,根据本发明的农药制剂的组分a)的一种或多种农药选自芳氧基苯氧基丙酸除草剂,苯甲酰基环己烷二酮除草剂,三唑并嘧啶除草剂,嗜球果伞素类杀真菌剂,三唑杀真菌剂,烟碱类杀昆虫剂和拟除虫菊酯杀昆虫剂。
特别优选,根据本发明的农药制剂的组分a)的一种或多种农药选自马拉硫磷,氯氰菊酯,酸式草甘膦和盐式草甘膦。在它们当中,优选酸式和盐式草甘膦。在草甘膦的盐中,优选草甘膦异丙基铵盐。
农药和它们相应的农药分类可以参见例如British CropProtection Council的“The Pesticide Manual”,14th Edition 2006,Editor:CDS Tomlin。
农药的生物学活性能够通过是作用持续时间和活性化合物浓度函数的活性化合物对叶子的作用所引起的植物生长或植物损害来确定。
根据本发明的农药制剂的组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选是N-取代的,优选N-烷基-或N-烯基-取代的2-吡咯烷酮-4-羧酸及其盐、酯和酰胺。
特别优选,根据本发明的农药制剂的组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物选自是式(Z)化合物
其中
R1是C8-至C30-烷基或C8-至C30-烯基,
Y是OM,-O-[AO]n-X或NR2R3,
M是氢、碱金属或碱土金属、铵NH4 +或取代的铵,其中所述取代的铵优选选自一、二和三取代的铵,且所述取代的铵的氮原子上的取代基又选自具有1至4碳原子的烷基和CH2CH2OH,
A是C2-至C4-亚烷基或C6H5-(CH-CH2),
n是0至100的数,
X是C1至C20-烷基、苄基或取代的芳基残基,其中所述取代的芳基残基优选选自被1至3个取代基取代的苯基,且这些取代基又选自具有1至4碳原子的烷基和苯乙烯基,并且在n不是0的情况下X还可以表示氢,
R2和R3彼此独立地是氢,C1-至C20-烷基或(C2H4O)pH和
p是1至20的数。
在本发明的特别优选实施方式中,根据本发明的农药制剂的组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物选自式(1)化合物
其中
R1是C8-至C30-烷基或C8-至C30-烯基,和
M是氢、碱金属或碱土金属、铵NH4 +或取代的铵,其中所述取代的铵优选选自一、二和三取代的铵,且所述取代的铵的氮原子上的取代基又选自具有1至4碳原子的烷基和CH2CH2OH。
在本发明的又一特别优选实施方式中,根据本发明的农药制剂的组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物选自式(2)化合物
其中
R1是C8-至C30-烷基或C8-至C30-烯基,
A是C2-至C4-亚烷基或C6H5-(CH-CH2),
n是0至100的数,和
X是C1-至C20-烷基,苄基或取代的芳基残基,其中所述取代的芳基残基优选选自被1至3个取代基取代的苯基,且这些取代基又选自具有1至4碳原子的烷基和苯乙烯基,并且在n不是0的情况下X还可以表示氢。
在本发明的又一特别优选的实施方式中,根据本发明的农药制剂的组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物选自式(3)化合物
其中
R1是C8-至C30-烷基或C8-至C30-烯基,
R2和R3彼此独立地是氢,C1-至C20-烷基或(C2H4O)pH和
p是1至20的数。
在式(Z)和(1)至(3)中,R1优选是具有8至24个碳原子的直链或支化的烷基或烯基基团,尤其是具有8至18个碳原子的直链或支化的烷基或烯基基团。特别优选,R1是直链或支化的辛基残基、椰油基残基或油烯基残基。
在式(Z)和(1)中,M优选是氢,Na,K,Ca,铵,异丙基铵,N,N-二乙基-(2-羟基乙基)铵,一、二或三乙醇铵。
在式(Z)和(2)中,A优选是亚乙基或亚丙基和特别优选亚乙基。X优选是氢(如果n不是零),C1-至C4-烷基且特别优选甲基,n优选是1至40且特别优选是5至25。
如果式(Z)和(2)中的X是取代的芳基残基,则其优选是2,4,6-三仲丁基苯基或2,4,6-三苯乙烯基苯基。
在式(Z)和(3)中,R2和R 3优选是氢,C1-至C4-烷基或(C2H4O)pH。特别优选,R2和R3是甲基或-CH2-CH2-OH。
因为可以对根据本发明的农药制剂的组分b)的N-取代的2-吡咯烷酮-4-羧酸衍生物的化学结构进行许多变化选择并由此调节分子的物理特性和理化特性,所以N-取代的2-吡咯烷酮-4-羧酸衍生物可以满足不同的任务。
根据本发明的农药制剂的组分b)的N-取代的2-吡咯烷酮-4-羧酸衍生物,尤其是式(Z)和(1)至(3)化合物优选用作助剂、乳化剂、分散剂或润湿剂。
因此,本发明也提供一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物,优选选自式(Z)和(1)至(3)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据本发明的农药制剂中用作助剂的用途。
本发明也提供一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物,优选选自式(Z)和(1)至(3)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据本发明的农药制剂中用作乳化剂的用途。
在该情况下,特别优选的乳化剂是式(1)化合物,其中M不是氢(阴离子乳化剂),或式(2)化合物,其中n≥5(非离子型乳化剂)。
式(2)化合物,其中X不是氢且n≥5,特别优选适宜用作包含对水或OH基团敏感的活性化合物例如磺酰脲类(SUs)的农药制剂的乳化剂。
本发明也提供一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物,优选选自式(Z)和(1)至(3)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据本发明的农药制剂中用作润湿剂的用途。
式(1)化合物,其中M是Na、K、铵NH4 +或取代的铵,特别适宜用作润湿剂。
本发明也提供一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物,优选选自式(Z)和(1)至(3)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据本发明的农药制剂中用作分散剂的用途。
式(1)化合物,其中M是Na、K、铵NH4 +或取代的铵,特别适宜用作分散剂。
在本发明的优选实施方式中,根据本发明的农药制剂能够作为液体制剂(“配制剂类型”)存在,所述液体制剂选自水溶液(SL),浓悬浮剂(SC),悬乳剂(SE),乳油(EC),油分散剂(OD),水乳剂(EW)或微乳剂(ME)。
由于溶解度,式(1)化合物,其中M不是氢,或式(2)化合物,其中n≥10,特别优选适用于含水配制剂比如SLs、SCs、EWs、SEs和MEs中。
式(1)化合物,其中M是氢,或式(2)化合物,其中n≤9,或式(3)化合物在水中具有低溶解度,并因此特别适宜用作含溶剂或含油制剂比如ECs、EWs、SEs、MEs和ODs的辅剂。
在本发明的又一优选实施方式中,根据本发明的农药制剂作为固体制剂(“配制剂类型”)存在,所述固体制剂选自水溶性粉剂或颗粒剂(SP,SG)或水可分散粉剂或颗粒剂(WP,WDP,WG,WDG)。
式(Z)和(1)至(3)的化合物,其特点是优选>30℃和特别优选>40℃的熔点,特别优选适用于固体制剂中。
本发明也提供一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物和优选选自式(Z)和(1)至(3)一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物用于制备根据本发明的农药制剂的用途。
取决于配制剂类型,根据本发明的农药制剂能够通过各种途径制备,并且本领域技术人员足够熟悉其制备。
根据本发明的农药制剂的组分b)的N-取代的2-吡咯烷酮-4-羧酸能够通过将衣康酸与伯胺反应获得,并且能够如EP 0 069 512,US3,224,975和US 4,127,493的描述制备。
相应盐能够通过将N-取代的2-吡咯烷酮-4-羧酸与碱反应而制备。适宜的碱优选是NaOH,Ca(OH)2,CaCO3,KOH和胺比如氨,异丙胺,一、二或三乙醇胺。
相应酯能够例如通过将亚烷基氧化物加成至N-取代的2-吡咯烷酮-4-羧酸或通过将N-取代的2-吡咯烷酮-4-羧酸与任选经取代的聚乙二醇醚缩合而制备。所述酯还能够例如本领域技术人员已知地通过将N-取代的2-吡咯烷酮-4-羧酸用烷基醇、苄醇或其它芳族醇酯化而制备。
相应酰胺能够通过将N-取代的2-吡咯烷酮-4-羧酸与胺缩合而获得。
根据本发明的农药制剂包含组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物的优选量是0.1至50重量%,特别优选0.5至30重量%和特别优选1至20重量%。这些量按全部本发明的农药制剂计。
根据本发明的农药制剂包含组分a)的一种或多种农药的优选量是1至90重量%,特别优选2至80重量%和特别优选4至70重量%。这些量按全部本发明的农药制剂计。
根据本发明的农药制剂特别适于防控和/或抗击杂草、真菌疾病或昆虫侵染。
相应地,本发明也提供根据本发明的农药制剂用于防控和/或抗击杂草、真菌疾病或昆虫侵染的用途。
根据本发明的农药制剂优选以喷雾液形式施用至田间。在该情况下,喷雾液通过将浓缩配制剂用限定量的水稀释来制备。
在本发明的优选实施方式中,根据本发明的农药制剂作为喷雾液存在,并且包含0.001至10重量%,优选0.02至3重量%和特别优选0.025至2重量%的组分a)农药,以及0.001至3重量%,优选0.005至1重量%和特别优选0.01至0.5重量%的组分b)的N-取代的2-吡咯烷酮-4-羧酸衍生物。这些量按全部喷雾液计。
在喷雾液中,组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物与组分a)的一种或多种农药的重量比优选是1∶100至10∶1和特别优选1∶20至4∶1。
每公顷施用的农药量优选在0.005至5kg的范围内。N-取代的2-吡咯烷酮-4-羧酸衍生物的份额优选在0.002至约2.0kg/ha的范围内。所制备以施用的喷雾液体积优选在50至1000l/ha的范围内。
本文中,一种或多种农药和一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物还可以以所谓“桶混”制剂形式存在。在上述制剂中,一种或多种农药和一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物最初彼此分开地存在。在施用之前,一般为施用前短时间内,将两种制剂彼此混合,从而形成根据本发明的制剂。
在桶混方法中,在混合之前,一种或多种农药作为水中和/或溶剂中的配制剂存在或者作为固体配制剂存在。
在桶混方法中,在混合之前,一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物以溶于水或溶于溶剂或溶于水/溶剂混合物中的形式存在。
根据本发明的制剂可以包含增稠剂,溶剂,分散剂,乳化剂,防腐剂,助剂,粘合剂,稀释剂,崩解剂,润湿剂,透入促进剂,低温稳定剂,着色剂,消泡剂和抗氧化剂。
适于用作增稠剂的可以是在农业化学配制剂中常规用于该意图的全部物质,比如黄原胶和/或纤维素,例如羧基、甲基、乙基或丙基纤维素或(任选改性的)斑脱土,其重量按制得的组合物计为0.01至5%。适宜的溶剂是在农业化学配制剂中常规用于该意图的全部物质,例如芳族和脂族烃,N-甲基吡咯烷酮,环己酮,丁内酯,苯乙酮,乳酸酯比如乳酸乙基己基酯,碳酸酯比如碳酸亚丙酯,脂肪酸酰胺比如癸酸二甲基酰胺,亚磷酸或磷酸的酯比如乙基己基膦酸二(乙基己基)酯或三(乙基己基)磷酸酯,二醇,聚乙二醇,丙二醇,天然油和矿物油,以及脂肪酸酯。适宜的分散剂和乳化剂是在农业化学配制剂中常规用于该意图的全部物质比如非离子、两性、阳离子型和阴离子型(聚合物型)表面活性剂。可以用作防腐剂的是在农业化学配制剂中常规用于该意图的全部物质,比如有机酸及其酯,例如抗坏血酸,抗坏血酸基棕榈酸酯,山梨酸盐/酯,苯甲酸,4-羟基苯甲酸甲酯和4-羟基苯甲酸丙酯,丙酸盐/酯,酚,例如2-苯基苯酚盐/酯,1,2-苯并异噻唑啉-3-酮,甲醛,亚硫酸及其盐。可以用作助剂的是在农业化学配制剂中常规用于该意图的全部物质,比如任选交联的聚甘油酯,醇烷氧基化物,例如醇乙氧基化物,烷基多糖,脂肪胺乙氧基化物,亚磷酸或磷酸的酯比如乙基己基膦酸二(乙基己基)酯或三(乙基己基)磷酸酯,去水山梨糖醇和山梨糖醇乙氧基化物衍生物和烷基琥珀酸和/或烯基琥珀酸的衍生物。适宜的透入促进剂是常规用来改善农药进入植物或进入靶标有机体的透入的全部物质。例如,透入促进剂能够这样定义,它们自含水喷雾液和/或自植物表面的喷洒覆盖层物透入植物角质层,从而能够增加活性组分在角质层中的物质运动性(迁移性)。描述于文献中的方法能够用来确定该特性(Baur等人,1997,PesticideScience 51,131-152)。
对于固体配制剂考虑在农业化学配制剂中常规用于该意图的全部粘合剂,比如聚乙烯基吡咯烷酮,聚乙烯醇,羧甲基纤维素,糖类,例如蔗糖,山梨糖醇或淀粉。作为稀释剂、吸收剂或载体适宜的是在农业化学配制剂中常规用于该意图的全部物质,比如炭黑,牛油,高岭土,硬脂酸铝,硬脂酸钙或硬脂酸镁,三聚磷酸钠,四硼酸钠,硫酸钠,硅酸盐和苯甲酸钠。作为分散剂起作用的是在农业化学配制剂中常规用于该意图的全部物质,比如纤维素,例如羧甲基纤维素,聚乙烯基吡咯烷酮,乙酸钠或乙酸钾,碳酸盐,碳酸氢盐,倍半碳酸盐,硫酸铵或磷酸氢二钾。
作为润湿剂可以使用在农业化学配制剂中常规用于该意图的全部物质,比如醇乙氧基化物,醇烷氧基化物,EO/PO嵌段共聚物(EO:环氧乙烷单元;PO:丙二醇单元)或任选乙氧基化的烷基磺酸。作为低温稳定剂起作用的可以是在农业化学配制剂中常规用于该意图的全部物质。例如可以提及脲、甘油和丙二醇。适宜的着色剂是在农业化学配制剂中常规用于该意图的全部物质,比如水或油可溶的着色剂,以及有机和无机色素。适宜的消泡剂是在农业化学配制剂中常规用于该意图的全部物质,比如脂肪酸烷基酯烷氧基化物;有机聚硅氧烷比如聚二甲基硅氧烷及其与超细、任选硅烷化硅酸的混合物;全氟烷基膦酸盐/酯和全氟烷基亚膦酸盐/酯;石蜡、蜡和微晶蜡及其与硅烷化硅酸的混合物。还有利的是不同的沫状物抑制剂例如硅油、石蜡油和/或蜡那些的混合物。作为抗氧化剂考虑的是在农业化学配制剂中常规用于该意图的全部物质,比如BHT(2,6-二-叔丁基-4-甲基酚)。
此外,根据本发明的制剂可以包含一种或多种农业化学的盐,优选钾盐或铵盐。
实施例:
下文借助实施例阐明本发明;然而,所述实施例在任何情况下都不视为对本发明的限制。
在实施例中,百分比是重量%,除非另有明确描述。
制备N-取代的2-吡咯烷酮-4-羧酸的一般规程:
将伯胺预置于配有回流冷凝器和冷凝交换器(Wechselvorstoβ)的2升搅拌机,并在通氮下加热至100℃。在该温度下,于缓慢搅拌下将适当量的衣康酸以五个等份引入。混合物反应放热,在每份之后搅拌30分钟。然后,将反应混合物加热至回流(约120℃),并保持在回流下6小时。然后,将冷凝交换器切换为除去反应的水。在4小时期间内,温度逐渐增加至180℃而反应的水收集于接受器中。
实施例1:
根据上述规程,将773.1g的伯油胺(M=264.7g/mol,Clariant公司的GenaminOL 100D)和400.0g的衣康酸(M=130.1g/mol)进行反应。在反应期间,除去50.2g的水。所获得的产物具有142.3mg KOH/g(理论:148.9mg KOH/g)的酸值。含水量<0.05%。获得1072.7g的N-油烯基-2-吡咯烷酮-4-羧酸(化合物1)。
实施例2:
根据上述规程,将683.5g的椰油脂肪伯胺(M=195.5g/mol,Clariant的GenaminCC 100D)和478.8g的衣康酸(M=130.1g/mol)进行反应。在反应期间,除去66.9g的水。所获得的产物具有173.0mg KOH/g(理论:182.4mg KOH/g)的酸值。含水量<0.05%。获得1050.1g的N-椰油基-2-吡咯烷酮-4-羧酸(化合物2)。
制备N-取代的2-吡咯烷酮-4-羧酸酯的规程。
将N-取代的2-吡咯烷酮-4-羧酸和聚乙二醇一甲基醚(Clariant公司的聚乙二醇M类型)以1∶1摩尔比预置于配有回流冷凝器、冷凝交换器的1升搅拌机,反应通氮,混合物在搅拌下加热至200℃。在该温度,将混合物再搅拌4小时,蒸除反应的水。然后,仔细施加水泵真空(22毫巴),将混合物加热至220℃。一旦达到所希望的残余酸值,则用氮撤除真空,使混合物冷却。各实验概括于表1中。
制备N-取代的2-吡咯烷酮-4-羧酸盐的规程:
实施例11:
将379g的N-油烯基-2-吡咯烷酮-4-羧酸(化合物1)与61g的一乙醇胺反应。获得440g的N-油烯基-2-吡咯烷酮-4-羧酸一乙醇铵盐(化合物11),其具有的酸值=125mg KOH/g和碱性氮N=3.3%。
实施例12:
将311g的N-椰油基-2-吡咯烷酮-4-羧酸(化合物2)与117g的N,N-二乙基氨基乙醇反应。获得428g的N-椰油基-2-吡咯烷酮-4-羧酸N,N-二乙基-(2-羟基乙基)铵盐(化合物12),其具有的酸值=125mg KOH/g和碱性氮N=3.3%。
实施例13:N-取代的2-吡咯烷酮-4-羧酸与二甲胺的反应:
将2mol N-取代的2-吡咯烷酮-4-羧酸预置于配有回流冷凝器和冷凝交换器的1升搅拌机,在加热至180℃下引入气态二甲胺,连续蒸除形成的反应水。一旦残余酸值降至<5mg KOH/g(在约20小时之后),则停止引入二甲胺,通过减压下引入氮冲洗出过量的二甲胺。然后,在通氮下冷却反应混合物。
实施例14:确定植物毒性
植物毒性的确定在番茄植物(栽培种Astona F1)上进行,该栽培种是已知对经由叶表面吸收的植物毒性物质敏感的种类(“Phytotoxicity of different classes of adjuvants”,H.deRuiter,等人,Proceedings Fifth International Symposium onAdjuvants for Agrochemicals,1998,Ed.P.McMullan,pp.204-209)。
植物
在温室中,于14小时光照下,于18/12(±0.5)℃(昼/夜)的温度和70/80(±5)%(昼/夜)的相对大气压湿度下,栽培番茄植物(栽培种Astona F1)。在发芽之后12天,将幼苗移植入直径11cm、用细砂∶土壤(12号土壤,Colent b.v.,Lent,荷兰)的体积比=1∶2的细砂与土壤的混合物填充的塑料罐(1植株/罐)。
将各罐置于每日用中等浓度的营养素溶液润湿的地下灌溉衬垫上。
施用
在播种之后28天,在4-叶阶段处理植物,各植物具有15-17cm的高度。喷雾溶液的辅剂含量是0.5%(v/v或%体积)。
用气压操作式实验室喷雾器,将喷雾溶液施用至植物,从而得到施用率200l/ha。
视觉上为经处理植物评分在2和8天之后(DAT;DAT:处理之后的天数),借助定性等级(1至5)进行评价。本文中,1=叶子无褪色或坏死,直至5=经处理叶表面完全坏死。此外,在8天之后确定地上植物质量(鲜重)。在各情况下,按经处理植物的数量计来计算平均值。作为参比物质使用也用于农药制剂中的脂肪醇烷氧基化物。结果示于表2。
表2:用N-取代的2-吡咯烷酮-4-羧酸衍生物和脂肪醇烷氧基化物但不用农药来处理植物栽培种Astona F1的结果
实验 | 化合物 | 视觉评价(DAT 2) | 视觉评价(DAT 8) | 鲜重[g] |
1 | 未处理 | 1.0 | 1.0 | 8.6 |
2 | 化合物1 | 1.1 | 1.5 | 8.6 |
3 | 化合物5 | 1.0 | 1.0 | 8.6 |
4 | 脂肪醇烷氧基化物 | 2.9 | 3.0 | 7.5 |
化合物1和5显示最低的番茄植物的植物毒性反应征兆,而参比物质导致显著反应。在使用化合物1和5的情况下,形成的植物的质量与未处理植物相比并未降低,而用参比物质处理的植物生长更瘦弱,即具有较低的植物质量。
实施例15:农药制剂,草甘膦生物学活性的增高
喷雾溶液
通过桶混方法测试化合物1和化合物5用作除草剂草甘膦的助剂的适用性。此处,使用50%浓度的溶液。在化合物1的情况下,额外加入三乙醇胺以将该酸溶解。
通过将这些桶混溶液与商业草甘膦异丙基铵盐(包含62重量%的活性化合物草甘膦IPA盐;IPA:异丙基铵)水溶液混合,再加入水,由此形成根据本发明的制剂。草甘膦(基于酸当量)与助剂的比率在此相应于也在可商购草甘膦配制剂中所存在的。
为了更容易地监测助剂效果,使用降低剂量的草甘膦;施用量是135.2g酸当量/ha草甘膦IPA盐(相应于4.0mmol或0.68g酸当量/l,液体体积200l/ha)。缩写“a.e.”意指“酸当量”。
喷雾溶液包含下述浓度的助剂:0.0141%(v/v)。
植物
在温室中,于14小时光照下,于18/12(±0.5)℃(昼/夜)的温度和70/80(±5)%(昼/夜)的相对大气压湿度下,栽培野燕麦(野燕麦(Avena fatua),AVEFA)。经由高压汞灯和荧光管引入光照,其在叶平面上的功率为70W/m2(PAR;PAR:光合作用活性辐射(400-700nm))。将植物栽培于直径11cm、用细砂∶土壤(12号土壤,Colent b.v.,Lent,荷兰)的体积比=1∶2的细砂与土壤的混合物填充的塑料罐。
将罐置于每日用中等浓度营养素溶液润湿的地下灌溉衬垫上。在出苗之后,将AVEFA幼苗划分为6植株/罐,用于活性测试。
除草剂施用
用喷雾溶液来进行温室试验。测试助剂对草甘膦效力的效果。
用气压操作式实验室喷雾器,将喷雾溶液施用至植物,使得获得200l/ha的施用率。
野燕麦(AVEFA)达到2-3叶阶段后对其进行处理。
结果
在21天之后评价除草剂的效力。为此,测定剩余的地上植物部分(即以克计的鲜重(FW))的质量。将其和相对未处理植物计算的相对残余量(重量%)一起示于表3。
表3:助剂对草甘膦效力的效果(AVEFA)
实施例16:除草制剂,EC-配制剂
测试化合物3和化合物5作为EC配制剂(乳油)中的乳化剂的适用性。为此,制备包含活性化合物马拉硫磷和氯氰菊酯的根据本发明的农药制剂(表4)。
表4:马拉硫磷和氯氰菊酯EC配制剂
全部三种制剂都是贮藏稳定的EC-配制剂。为了评价各配制剂的品质,制备软(20ppm)和硬(342ppm)CIPAC标准水中的5%浓度的含水乳液,并在30℃下2、4和24小时的时间段之后进行评价。全部乳液在该时间段都是稳定的,未观察到相分离。
Claims (11)
1.农药制剂,其包含
a)一种或多种农药和
b)一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物。
2.根据权利要求1的农药制剂,其中所述组分b)的一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物选自式(Z)化合物
其中
R1是C8-至C30-烷基或C8-至C30-烯基,
Y是OM,-O-[AO]n-X或NR2R3,
M是氢、碱金属或碱土金属、铵NH4 +或取代的铵,其特征在于所述取代的铵优选选自一、二和三取代的铵,且所述取代的铵的氮原子上的取代基又选自具有1至4碳原子的烷基和CH2CH2OH,
A是C2-至C4-亚烷基或C6H5-(CH-CH2),
n是0至100的数,
X是C1-至C20-烷基、苄基或取代的芳基残基,其中所述取代的芳基残基优选选自被1至3个取代基的取代的苯基,且这些取代基又选自具有1至4碳原子的烷基和苯乙烯基,并且在n不是0的情况下还可以表示氢,
R2和R3彼此独立地是氢,C1-至C20-烷基或(C2H4O)pH和
p是1至20的数。
6.一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据权利要求1至5中一项或多项的农药制剂中用作助剂的用途。
7.一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据权利要求1至5中一项或多项的农药制剂中用作乳化剂的用途。
8.一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据权利要求1至5中一项或多项的农药制剂中用作润湿剂的用途。
9.一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物优选在根据权利要求1至5中一项或多项的农药制剂中用作分散剂的用途。
10.一种或多种N-取代的2-吡咯烷酮-4-羧酸衍生物用于制备根据权利要求1至5中一项或多项的农药制剂的用途。
11.根据权利要求1至5中一项或多项的农药制剂用于防控和/或抗击杂草、真菌疾病或昆虫侵染的用途。
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DE102009043122.5 | 2009-09-25 | ||
DE102009043122 | 2009-09-25 | ||
PCT/EP2010/005737 WO2011035873A1 (de) | 2009-09-25 | 2010-09-18 | Pestizidzubereitungen enthaltend derivate von pyrrolidon-4-carbonsäure |
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US (1) | US20120264611A1 (zh) |
EP (1) | EP2480071A1 (zh) |
CN (1) | CN102595883A (zh) |
AU (1) | AU2010297634A1 (zh) |
BR (1) | BR112012006569A2 (zh) |
WO (1) | WO2011035873A1 (zh) |
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DE102010046680A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Limited | Verwendung von N-substituierten 2-Pyrrolidon-4-carbonsäureestern als Lösemittel |
DE102010046679A1 (de) | 2010-09-16 | 2012-03-22 | Clariant International Ltd. | Pestizidzubereitungen enthaltend N-substituierte 2-Pyrrolidon-4-carbonsäureester |
DE102012017739A1 (de) | 2012-09-07 | 2014-03-13 | Clariant International Ltd. | Verfahren zur Herstellung von N-substituierten Pyrrolidoncarbonsäureestern |
CN112430156A (zh) * | 2020-12-04 | 2021-03-02 | 中诚国联(河南)生物科技有限公司 | 一种防治刺吸式害虫的高塔药肥颗粒剂制备方法及其应用 |
Citations (4)
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US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
US5283229A (en) * | 1989-12-11 | 1994-02-01 | Isp Investments Inc. | Delivery system for agricultural chemicals |
CN1306396A (zh) * | 1998-06-04 | 2001-08-01 | 汉普郡化学公司 | 作为草甘膦辅助剂的n-酰基肌氨酸盐 |
WO2002021921A1 (de) * | 2000-09-13 | 2002-03-21 | Basf Aktiengesellschaft | Öl-suspensionskonzentrate auf basis eines cyclohexenonoximether-lithiumsalzes und deren verwendung als pflanzenschutzmittel |
-
2010
- 2010-09-18 WO PCT/EP2010/005737 patent/WO2011035873A1/de active Application Filing
- 2010-09-18 BR BR112012006569A patent/BR112012006569A2/pt not_active IP Right Cessation
- 2010-09-18 US US13/497,975 patent/US20120264611A1/en not_active Abandoned
- 2010-09-18 EP EP10755112A patent/EP2480071A1/de not_active Withdrawn
- 2010-09-18 CN CN2010800427242A patent/CN102595883A/zh active Pending
- 2010-09-18 AU AU2010297634A patent/AU2010297634A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
US5283229A (en) * | 1989-12-11 | 1994-02-01 | Isp Investments Inc. | Delivery system for agricultural chemicals |
CN1306396A (zh) * | 1998-06-04 | 2001-08-01 | 汉普郡化学公司 | 作为草甘膦辅助剂的n-酰基肌氨酸盐 |
WO2002021921A1 (de) * | 2000-09-13 | 2002-03-21 | Basf Aktiengesellschaft | Öl-suspensionskonzentrate auf basis eines cyclohexenonoximether-lithiumsalzes und deren verwendung als pflanzenschutzmittel |
Non-Patent Citations (1)
Title |
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ROBERT B. LOGIN: "Pyrrolidone-based surfactions (a literature review)", 《JOURNAL OF THE AMERICAN OIL CHEMICALS’SOCIETY》 * |
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WO2011035873A1 (de) | 2011-03-31 |
EP2480071A1 (de) | 2012-08-01 |
AU2010297634A1 (en) | 2012-05-03 |
US20120264611A1 (en) | 2012-10-18 |
BR112012006569A2 (pt) | 2015-09-08 |
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