CN112292034A - 杀虫剂组合物 - Google Patents
杀虫剂组合物 Download PDFInfo
- Publication number
- CN112292034A CN112292034A CN201980039630.0A CN201980039630A CN112292034A CN 112292034 A CN112292034 A CN 112292034A CN 201980039630 A CN201980039630 A CN 201980039630A CN 112292034 A CN112292034 A CN 112292034A
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- Prior art keywords
- compound
- dissolving agent
- present
- pesticidal
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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
- 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
- A01N37/22—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 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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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
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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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
- A01N25/02—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 liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
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Abstract
本发明涉及含有2‑氟‑3‑(N‑甲基苯甲酰胺)‑N‑(2‑溴‑6‑三氟甲基‑4‑(七氟丙烷‑2‑基)苯基)苯甲酰胺、及clogP为0.1～2.1的溶解剂的杀虫剂组合物。
Description
技术领域
本发明涉及杀虫剂组合物，尤其涉及作为杀虫成分的2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺的溶解性优异、杀虫效果好的杀虫剂组合物。
背景技术
为了提高基于杀虫剂组合物的杀虫效果，需要使杀虫成分充分溶解于该组合物中。因此，根据所使用的杀虫成分的种类而对溶解杀虫成分的溶解剂的种类进行适当选择在实用上至关重要。
作为代表性的杀虫成分，可列举拟除虫菊酯系化合物。例如在专利文献1中公开了含有煤油难溶性拟除虫菊酯化合物作为杀虫成分、以及属于芳香族酰胺系化合物的N,N-二乙基间甲苯甲酰胺作为其溶解剂的气雾剂。
近年来，已经出现了对上述拟除虫菊酯系化合物等杀虫成分产生抗药性的害虫。例如难以驱除对拟除虫菊酯系化合物产生抗药性的德国小蠊(Blattella germanica)、温带臭虫(Cimex lectularius)，从而成为问题。另外，为了驱除栖息在药剂难以到达场所的害虫而反复用药剂进行处理，这也成为促进抗药性发展的原因。因此，正在探究即使对于对拟除虫菊酯系化合物等杀虫成分具有抗药性的害虫也发挥杀虫效果的新型杀虫成分。
作为如上所述的发挥杀虫效果的杀虫成分之一，有2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺。确认到该杀虫成分是即使对于对拟除虫菊酯系化合物等杀虫成分产生了抗药性的害虫也显示高致死效果和持续性的杀虫成分。但是，该杀虫成分为难溶性，制成各种剂型时存在不良情况，尽管如此却并未进行有关溶解性的研究。
现有技术文献
专利文献
专利文献1：日本特开2005-306753号公报
发明内容
发明要解决的课题
上述2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺对于通常的溶剂而言溶解性不足。因此，在制成各种剂型时使其溶解性提高成为课题。
本发明的目的在于提供：使2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺充分溶解于组合物、杀虫效果好的杀虫剂组合物。
用于解决课题的手段
本申请的发明人为了解决上述课题而反复进行了深入研究，结果发现，通过使用clogP为特定范围的溶解剂，能够提供使2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺充分溶解于组合物、杀虫效果好的杀虫剂组合物，从而完成了本发明。
即，本发明如以下所示。
(1)杀虫剂组合物，其含有2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺、及clogP为0.1～2.1的溶解剂。
(2)根据前述(1)所述的杀虫剂组合物，其含有苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、异丙醇及丙二醇二乙酸酯中的至少一者作为前述溶解剂。
(3)根据前述(1)或(2)所述的杀虫剂组合物，其还含有乙醇作为溶剂。
(4)气雾剂，其含有前述(1)～(3)中任一项所述的杀虫剂组合物和抛射剂。
(5)杀虫方法，其对害虫施用前述(1)～(3)中任一项所述的杀虫剂组合物。
发明效果
就本发明的一个实施方式的杀虫剂组合物而言，由于使用clogP为特定范围的溶解剂，因此能够提供：使2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺充分地溶解于组合物中、杀虫效果好的杀虫剂组合物。
具体实施方式
以下，对本发明的具体实施方式进行详细地说明，但是，本发明并不受以下实施方式的任何限定，只要可实现本发明的目的，则能够进行适当变更而实施。
本发明的一个实施方式的杀虫剂组合物含有2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺(以下，也称作“化合物A”)。作为化合物A，可使用溴虫氟苯双酰胺(broflanilide)(三井化学Agro株式会社制)等。
相对于本发明的一个实施方式的杀虫剂组合物而言的、化合物A的含量为0.1～90质量％，优选为0.5～80质量％，更优选为1.0～70质量％。
本发明的一个实施方式的杀虫剂组合物含有化合物A、并且还含有clogP为0.1～2.1的溶解剂。利用上述范围的溶解剂能够使化合物A效率良好地溶解于杀虫剂组合物中，适合于制成例如液剂、气雾剂、喷雾剂等。
利用本发明的溶解剂能够使化合物A的溶解性提高的原因虽不确定，但推测其原因在于化合物A所具有的官能团与溶解剂的亲和性良好。
其中，clogP是表示在辛醇相与水相之间的物质的分配的尺度。具体而言，clogP是将化合物的化学结构分解成其结构要素、对各片段所具有的疏水性片段常数(f值)进行累计而求出的。clogP例如可以使用MedChem1.01软件程序(Medicinal Chemistry Project，Pomona College，Pomona California公司制)来计算。
另外，本发明中的溶解剂的clogP可以从ChemExper的网站(https：//www.chemexper.com/)等获取。
本发明中的溶解剂的clogP为0.1～2.1，优选为0.15～1.4。
就本发明中的溶解剂而言，只要是clogP为上述范围且溶解化合物A的溶解剂，则无特别限制。但是，不包括如后述的溶剂(固体载体、液体载体、或稀释剂)那样、主要担负作为用于保持有效成分的载体的作用的物质、主要担负作为用于稀释化合物A的稀释剂的作用的物质。具体而言，可列举苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、丙二醇二乙酸酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、乙酸苄酯、1,2-二甲氧基乙烷、1-丙醇、异丙醇、1-丁醇、4-甲氧基苄醇、肉桂醇、苯酚及四氢呋喃等。
从提高化合物A的溶解性这样的观点出发，可优选为苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、丙二醇二乙酸酯、乙酸甲酯、乙酸乙酯、1,2-二甲氧基乙烷、1-丙醇、异丙醇、1-丁醇、苯酚及四氢呋喃。
其中，更优选苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、1,2-二甲氧基乙烷、异丙醇、苯酚及四氢呋喃。
特别优选的是苄醇、N-甲基-2-吡咯烷酮、苯酚及四氢呋喃。
就本发明的一个实施方式的杀虫剂组合物而言，在上述溶解剂中，从闪点高、安全性优异、毒性值低、臭味少这样的方面出发，优选含有苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、异丙醇及丙二醇二乙酸酯中的至少一者。
另外，本发明中的溶解剂优选为能够溶解2.5质量％以上的化合物A的溶解剂，更优选能够溶解5质量％以上的溶解剂，进一步优选能够溶解10质量％以上的溶解剂，特别优选能够溶解20质量％以上的溶解剂。
本发明的一个实施方式的杀虫剂组合物可以将上述溶解剂单独使用或组合2种以上而使用。
本发明的一个实施方式的杀虫剂组合物中，上述溶解剂的含量为0.1～90质量％，优选为1.0～60质量％，更优选为2.0～50质量％。上述溶解剂的含量可以为3.0质量％以上、4.0质量％以上，另外，可以为40质量％以下、30质量％以下、20质量％以下、10质量％以下。通过设为上述范围，从而能够抑制因使用所导致的易燃性、不良气味、对房屋设备的污染。
本发明的一个实施方式的杀虫剂组合物中，化合物A与上述溶解剂的含量比以质量比计为900：1～1：900，优选为200：1～1：200，更优选为50：1～1：50。通过以上述范围进行使用，从而能够制成稳定的制剂，能够抑制对房屋设备等的污染。
就本发明的一个实施方式的杀虫剂组合物而言，除含有化合物A及上述溶解剂外，还可以含有例如各种溶剂、拟除虫菊酯系化合物或氨基甲酸酯系化合物等杀虫成分、驱避剂、增效剂、抗氧化剂、乳化剂等。
溶剂是指有别于上述的溶解剂、而作为固体载体、液体载体、或稀释剂使用的溶剂。即，是指主要担负作为用于保持有效成分的载体的作用、作为用于稀释化合物A的稀释剂的作用的物质，不包括如上述的溶解剂那样、主要担负使化合物A充分溶解的作用的物质。可列举例如乙醇、正链烷烃、异链烷烃及环烷烃等饱和烃系溶剂、二丙二醇单甲基醚、3-甲氧基-3-甲基-1-丁醇等醚类、以及水等。它们可以单独使用或混合2种以上而使用。其中，优选使用乙醇。
作为杀虫成分，可列举例如：丙烯菊酯、胺菊酯、炔丙菊酯、苯醚菊酯、苄呋菊酯、苯醚氰菊酯、氯菊酯、氯氰菊酯、溴氰菊酯、四溴菊酯、氟氯氰菊酯、炔呋菊酯、炔咪菊酯、醚菊酯、氰戊菊酯、甲氰菊酯、氟硅菊酯、甲氧苄氟菊酯、氯氟醚菊酯、四氟甲醚菊酯、四氟苯菊酯、2-甲基-4-氧代-3-(2-丙炔基)-环戊-2-烯基-3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷甲酸酯等拟除虫菊酯系化合物；敌敌畏、杀螟硫磷、杀虫畏、倍硫磷、毒死蜱、二嗪农等有机磷化合物；残杀威、西维因、恶虫酮、仲丁威等氨基甲酸酯化合物；虱螨脲、氟啶脲、氟铃脲、除虫脲、灭蝇胺、1-(2,6-二氟苯甲酰基)-3-[2-氟-4-(1,1,2,3,3,3-六氟丙氧基)苯基]脲等几丁质合成抑制剂；蚊蝇醚、甲氧普林、烯虫乙酯、苯氧威等保幼激素类似物；芬普尼等N-苯基吡唑系化合物；等等。
作为驱避剂，可列举例如N,N-二乙基间甲苯甲酰胺、柠檬烯、芳樟醇、香茅醛、薄荷醇、薄荷酮、扁柏酚、香叶醇、桉树醇、茚虫威、蒈烷-3,4-二醇(carane-3,4-diol)、2-(2-羟基乙基)-1-哌啶甲酸1-甲基丙酯、3-(N-正丁基-N-乙酰基)氨基丙酸乙酯、对薄荷烷-3,8-二醇等。
作为增效剂，可列举例如胡椒基丁醚、MGK264、S421、IBTA、SYNEPIRIN 500等。
作为抗氧化剂，可列举例如BHT、BHA等，作为乳化剂，可列举聚氧乙烯脂肪酸酯、甘油脂肪酸酯、失水山梨醇脂肪酸酯等表面活性剂等。
本发明的一个实施方式的杀虫剂组合物可通过将化合物A及上述溶解剂、以及根据需要的其他期望成分在常温或加热下混合来得到。
本发明的一个实施方式的杀虫剂组合物可以作为气雾剂、泵剂(pumpingformulation)、液剂、粉剂、加热蒸散剂等利用。其中，优选制成气雾剂、泵剂、液剂等液滴附着于害虫的剂型。通过制成这样的剂型，可效率良好地发挥杀虫效果。
在制成气雾剂时，可以使用例如液化石油气、二甲醚、1,3,3,3-四氟丙烯、氮气、二氧化碳等抛射剂。
本发明的一个实施方式的杀虫剂组合物可以对例如下述害虫施用：德国小蠊、黑胸大蠊、美洲大蠊、日本大蠊、棕色蜚蠊等蜚蠊类；犬栉首蚤、猫栉首蚤等蚤类；蜜蜂、黄蜂等蜂类；家蝇、黑腹果蝇等蝇类；球潮虫、鼠妇虫、少棘蜈蚣等多足类；红背蜘蛛、白额巨蟹蛛、跳蛛等蜘蛛类；刻纹棱胸切叶蚁、日本黑褐蚁、阿根廷蚁等蚁类；栖北散白蚁、台湾乳白蚁等白蚁类；褐翅椿象、绿椿象、粉虱、温带臭虫等椿象类；黑尾叶蝉、斜纹夜蛾等蛾类；淡色库蚊、白纹伊蚊等蚊类；柏氏禽刺螨、肉食螨、粉螨、尘螨、肉食螨、蜱等螨类；等等。
实施例
以下，利用实施例对本发明进行进一步说明，但本发明并不受下述例子限制。
试验例1：溶解性试验
(实施例1～19、比较例1～8)
作为2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺(化合物A)，在试验中使用溴虫氟苯双酰胺(三井化学Agro株式会社制)。
以使化合物A的浓度成为2.5、5、10、20、30、40重量％的方式，对表1中记载的溶解剂进行搅拌并使其溶解。将试验结果示于表1。需要说明的是，表1的评价基准如下所示。
(评价基准)
○：充分溶解，无残留固态成分
×：未完全溶解，有残留固态成分
[表1]
如表1的结果所示，在使用了cLogP为0.1～2.1的溶解剂的实施例中，能够使期望量(2.5重量％)的化合物A溶解于组合物中。
另一方面，在使用了cLogP不在0.1～2.1范围内的溶解剂的比较例中，无法使2.5重量％的化合物A溶解于组合物中。
试验例2：杀虫效力试验
(实施例20～24、比较例9、对照例1～5)
(受试品的制备)
将表2中记载的各成分在室温下(约25℃)进行搅拌并溶解。具体而言，制作包含1.0质量/容量％的化合物A、及表2中记载的5.0质量/容量％的溶解剂的乙醇溶液。在上述乙醇溶液105mL中填充液化石油气345mL，制成气雾剂。
(杀虫效力试验)
按照下述(i)～(iv)的步骤实施了试验。
(i)向塑料制杯子(
高度100mm)中放入供试虫(黑胸大蠊：雌成虫10只)。
(ii)将放入有供试虫的杯子倾斜(角度45°)设置在地板角部，使用定量喷雾装置从距离杯子50cm的位置喷射受试品1秒钟。
(iii)喷射结束后，将供试虫移至清洁的容器中，放入含水的脱脂棉。
(iv)在25℃的试验室中静置，在24小时后调查供试虫的致死数，根据下式求出致死率(％)。
致死率(％)＝(24小时后的供试虫的致死数/供试虫数)×100进行共计3次上述试验，将致死率(％)的平均值示于下述表2。
需要说明的是，实施例及比较例的受试品的喷射量如下所示。
·实施例20：12.52g/10秒
·实施例21：12.24g/10秒
·实施例22：12.62g/10秒
·实施例23：13.40g/10秒
·实施例24：12.52g/10秒
·比较例9：12.14g/10秒
[表2]
由表2的结果可知：通过使用cLogP为0.1～2.1的溶解剂，从而显示优异的杀虫效果。
使用特定的方式对本发明进行了详细地说明，但在不脱离本发明的主旨和范围的情况下能够进行各种变更及变形，这对于本领域技术人员而言是显而易见的。需要说明的是，本申请基于在2018年6月14日提出申请的日本专利申请(日本特愿2018-113612)，将其全部内容通过引用而并入本说明书中。
Claims (5)
1.杀虫剂组合物，其含有2-氟-3-(N-甲基苯甲酰胺)-N-(2-溴-6-三氟甲基-4-(七氟丙烷-2-基)苯基)苯甲酰胺、及clogP为0.1～2.1的溶解剂。
2.根据权利要求1所述的杀虫剂组合物，其含有苄醇、N-甲基-2-吡咯烷酮、3-甲氧基-N,N-二甲基丙酰胺、异丙醇及丙二醇二乙酸酯中的至少一者作为所述溶解剂。
3.根据权利要求1或2所述的杀虫剂组合物，其还含有乙醇作为溶剂。
4.气雾剂，其含有权利要求1～3中任一项所述的杀虫剂组合物和抛射剂。
5.杀虫方法，其对害虫施用权利要求1～3中任一项所述的杀虫剂组合物。
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