JPS62277307A - Insecticide containing boron compound - Google Patents
Insecticide containing boron compoundInfo
- Publication number
- JPS62277307A JPS62277307A JP10684886A JP10684886A JPS62277307A JP S62277307 A JPS62277307 A JP S62277307A JP 10684886 A JP10684886 A JP 10684886A JP 10684886 A JP10684886 A JP 10684886A JP S62277307 A JPS62277307 A JP S62277307A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- substituted
- insecticide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002917 insecticide Substances 0.000 title claims abstract description 10
- 150000001639 boron compounds Chemical class 0.000 title claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- -1 nitrogen- containing heterocyclic compound Chemical class 0.000 claims abstract description 12
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 6
- 239000000642 acaricide Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 239000005645 nematicide Substances 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 230000001069 nematicidal effect Effects 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 241000244206 Nematoda Species 0.000 abstract description 5
- 241000238657 Blattella germanica Species 0.000 abstract description 3
- 241000238876 Acari Species 0.000 abstract description 2
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical class C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 241000238631 Hexapoda Species 0.000 abstract 1
- 241000243786 Meloidogyne incognita Species 0.000 abstract 1
- 241000257226 Muscidae Species 0.000 abstract 1
- 241000488581 Panonychus citri Species 0.000 abstract 1
- 241000258242 Siphonaptera Species 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- ANTSJIQCFJUDRI-UHFFFAOYSA-N pyridine;tris(4-fluorophenyl)borane Chemical compound C1=CC=NC=C1.C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ANTSJIQCFJUDRI-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 241001454293 Tetranychus urticae Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical class [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 241000239290 Araneae Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000490513 Ctenocephalides canis Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000084475 Delia antiqua Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- OUIICHMNVZJEIW-UHFFFAOYSA-N chloromethane;hexane Chemical compound ClC.CCCCCC OUIICHMNVZJEIW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
イ、産業上の利用分野
本発明は下記の一般式で示されるホウ素化合物を有効成
分として含有する殺昆虫、殺ダニ、殺線虫剤に関する。DETAILED DESCRIPTION OF THE INVENTION A. Field of Industrial Application The present invention relates to insecticides, acaricides, and nematicides containing a boron compound represented by the following general formula as an active ingredient.
〔式中、Ｘ、Ｙは各々独立に水素原子、ハロゲン原子、
低級アルキル基、又は低級アルコキシ基を、２はＲ，Ｒ
２ＮＨ、又は含窒素複素環化合物（低級アルキル基で置
換されても良い。）を表わす。但し、Ｒ１，Ｒ２は各々
独立に水素原子、低級アルキル基、低級アルケニル基、
シクロアルキル基、フェニル基（ハロゲン原子、又はメ
チル基で置換されても良い。）、又は複素環式基を表わ
す。〕口、従来の技術及び問題点
従来、トリフェニルホウ素、又はトリー置換フェニルホ
ウ素のアミン配位化合物は、例えばゾヤーナル オブ
インクェクト ディジースズ（Ｊｏｕｒｎａｌ ｏｆ
工１１ｆ＠ｃｔ ＤｉｓｅＩｅｓ ） １：ｉ４ 、３
０４（１９６４）および米国特許第３，２１１，６７９
号によシ、殺菌活性を示すことが知られている。しかし
、上記化合物の殺虫活性については記載されていない。[In the formula, X and Y each independently represent a hydrogen atom, a halogen atom,
lower alkyl group or lower alkoxy group, 2 is R, R
2NH, or a nitrogen-containing heterocyclic compound (which may be substituted with a lower alkyl group). However, R1 and R2 each independently represent a hydrogen atom, a lower alkyl group, a lower alkenyl group,
It represents a cycloalkyl group, a phenyl group (which may be substituted with a halogen atom or a methyl group), or a heterocyclic group. [Background Art and Problems] Conventionally, amine coordination compounds of triphenylboron or tri-substituted phenylboron have been used, for example, in the
Infect Diseases (Journal of
Engineering 11f@ct DiseIes) 1:i4,3
04 (1964) and U.S. Patent No. 3,211,679
It is known that it exhibits bactericidal activity. However, the insecticidal activity of the above compounds is not described.
また、下記一般式で表わされるホウ素誘導体を含んでい
る殺昆虫、殺ダニおよび農業用殺菌剤については日本特
許公告昭４９−３４８１４号公報により公知である。Furthermore, insecticides, acaricides, and agricultural fungicides containing boron derivatives represented by the following general formula are known from Japanese Patent Publication No. 1983-34814.
（式中、ＸｌおよびＸ２は各々メチル基を表わし、又は
ＸおよびＸはそれらが結合する窒素息子と一緒になって
４−メチル−１−ピペラゾニ／１４ｔ−表わし、Ｘは水
素、もしくはハロダン原子、または炭素数１〜４のアル
キル、アルコキシ、モジくはアルキルチオ基を表わす。(In the formula, Xl and X2 each represent a methyl group, or X and X together with the nitrogen son to which they are bonded represent 4-methyl-1-piperazoni/14t-, and X is hydrogen or a halodane atom, Or it represents an alkyl, alkoxy, modi or alkylthio group having 1 to 4 carbon atoms.
）
ハ８問題点を解決するための手段
本発明者らは 新規な殺昆虫、める中
で、下記一般式で示されるホウ素化合物のすぐれた殺虫
活性を発見し、本発明を完成させた。) Means for Solving Problem C8 The present inventors have discovered the excellent insecticidal activity of a boron compound represented by the following general formula while developing a novel insecticide, and have completed the present invention.
式中、Ｘ、Ｙは各々独立に水素原子、ハロダン原子、低
級アルキル基、又は低級アルコキシ基を表わす。ここで
、ハロダン原子の例としては、フッ素、塩素、臭素、ヨ
ウ素原子が、低級アルキル基の例としてはメチル、エチ
ル、プロピル、イソプロピル基等が、低級アルコキシ基
の例としてはメトキシ、エトキシ、プロポキシ、イソプ
ロポキシ、ブトキシ、アミルオキシ、ヘキシルオキシ、
ヘプチルオキシ基等が挙げられる。式中、２はＲ１Ｒ２
ＮＫ、又は含窒素複素環化合物（低級アルキル基で置換
されても良い。）を表わす。Ｒ１，Ｒ２は各々独立に水
素原子、低級アルキル基、低級アルケニル基、シクロア
ルキル基、フェニル基（ハロダン原子、又はメチル基で
置換されても良い。）又は複素環式基を表わす。２の例
としては、表−１のＺの欄に例示されたアミン類、複素
環化合物が挙げられる。In the formula, X and Y each independently represent a hydrogen atom, a halodane atom, a lower alkyl group, or a lower alkoxy group. Here, examples of halodane atoms include fluorine, chlorine, bromine, and iodine atoms; examples of lower alkyl groups include methyl, ethyl, propyl, and isopropyl groups; and examples of lower alkoxy groups include methoxy, ethoxy, and propoxy. , isopropoxy, butoxy, amyloxy, hexyloxy,
Examples include heptyloxy group. In the formula, 2 is R1R2
Represents NK or a nitrogen-containing heterocyclic compound (which may be substituted with a lower alkyl group). R1 and R2 each independently represent a hydrogen atom, a lower alkyl group, a lower alkenyl group, a cycloalkyl group, a phenyl group (which may be substituted with a halodane atom or a methyl group), or a heterocyclic group. Examples of 2 include the amines and heterocyclic compounds listed in the Z column of Table 1.
本発明に関わる上記化合物は下記一般式によって合成す
ることができる。The above compounds related to the present invention can be synthesized according to the following general formula.
〔式中、ｘ、ｙ、ｚは前記のとおシである。〕即ち、ト
１１フェニルホウ素誘導体（２）と含窒素化合物（１）
とを等モル、窒素、又はヘリウム気流下、エチルエーテ
ルナトのエーテル類、ベンゼン、トルエン、キシレンな
どの芳香族炭化水素類、クロロホルム、ジクロロメタン
、１，２−ノクロロエタン、クロルベンゼンなどハロダ
ン化合物類などから選ばれた溶媒、又はそれらの２以上
の混合溶媒中で混合した後、水洗を行ない、無水硫酸ナ
トリウムで乾燥し、溶媒を減圧で留去する。得られた結
晶を適当な溶媒で再結晶すると本発明に関わる化合物（
３）が得られる。反応温度は０℃から５０℃であシ、反
応時間は１時間から２日間である。[In the formula, x, y, and z are as defined above. ] That is, the 11 phenylboron derivative (2) and the nitrogen-containing compound (1)
under a nitrogen or helium stream, aromatic hydrocarbons such as benzene, toluene, xylene, halodane compounds such as chloroform, dichloromethane, 1,2-nochloroethane, chlorobenzene, etc. After mixing in a solvent selected from the following or a mixed solvent of two or more thereof, the mixture is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. When the obtained crystals are recrystallized from an appropriate solvent, the compound related to the present invention (
3) is obtained. The reaction temperature is 0°C to 50°C, and the reaction time is 1 hour to 2 days.
以下に本発明化合物についての代表的な合成例を示し、
具体的に説明する。Typical synthesis examples for the compounds of the present invention are shown below,
I will explain in detail.
合成例 ピリノン−トリス（４−フルオロフェニル）ホ
ウ素ピリジン（１０ｍｍｏｌｅ ）、トリス（４−フル
オロフェニル）ホウ素（１０ｍｍｏｌｅ ）を独立に、
ニーｆルーベンゼン（１：１）の混合ｍｆＡ各々、５Ｑ
、ｖｕに溶解させた後、窒素ガスで系を置換する。Synthesis Example Pyrinone-tris(4-fluorophenyl)boronpyridine (10mmole), tris(4-fluorophenyl)boron (10mmole) were independently
Mixed mfA of nee f rubenzene (1:1) each, 5Q
, vu, and then purging the system with nitrogen gas.
調整されたピリジン溶液にトリス（４−フルオロフェニ
ル）ホウ素溶液を１０分間で加える。１０時間攪拌した
後、水洗し、無水硫酸ナトリウムで乾燥し、溶媒を減圧
下で留去する。得られた粗結晶ｔノクロロメタンーヘキ
゛サンの混合溶媒から再結晶すると標記化合物が２．９
ｇ白色結晶として得られる。Tris(4-fluorophenyl)boron solution is added to the prepared pyridine solution over 10 minutes. After stirring for 10 hours, the mixture is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The obtained crude crystals were recrystallized from a mixed solvent of chloromethane-hexane to give the title compound with 2.9
g Obtained as white crystals.
同様の方法により本発明化合物が合成されるが、代表的
な化合物を表１に例示する。なお、以下の説明は表１の
中の化合物屋で行なう。Compounds of the present invention are synthesized by a similar method, and representative compounds are illustrated in Table 1. The following explanation will be given at the compound shop shown in Table 1.
本発明の化合物は殺虫剤として農園芸分野及び公衆衛生
上の有害若しくは不快な害虫、例えばコパネイナゴ等の
直翅目、チャバネゴキブリ等の網翅目、コロモジラミ等
のシラミ目、ヒメトビウンカ、モモアカアブラムシ等の
半翅目、チャノキイロアデミウマ等の膜翅目、ハスモン
ヨトウ、コナガ等の鱗翅目、イエバエ、タマネギバエ等
の双翅目、イヌノミ等の膜翅目、カブラババチ等の膜翅
目、ヤマトシロアリ等の等翅目、アズキゾウムシ、ニジ
ュウヤホシテントウ等の鞘翅目等の防除に効果的である
。The compound of the present invention can be used as an insecticide to control harmful or unpleasant pests in the field of agriculture, horticulture, and public health, such as Orthoptera such as the Japanese locust, Orthoptera such as the German cockroach, Orthoptera such as the German cockroach, Pyroptera such as the body louse, the Japanese brown planthopper, and the green peach aphid. Hymenoptera such as Hemiptera, Hymenoptera such as the tealworm, Lepidoptera such as Spodoptera nigra, and the diamondback moth, Diptera such as the house fly and onion fly, Hymenoptera such as the dog flea, Hymenoptera such as the turniphoptera, etc., etc. It is effective in controlling coleoptera, such as the beetle weevil and the ladybird beetle.
また、線虫剤として例えばサツマイモネコブセンチーウ
、ネグサレセンチュウ等の線虫類、ダニ剤としてナミハ
ダニ、ミカンハダニ等のダニ類の防除にも効果的である
。It is also effective as a nematode agent for controlling nematodes such as the sweet potato nematode and Negusare nematode, and as an acaricide for controlling mites such as the two-spotted spider mite and orange spider mite.
本発明の化合物は前述のごとく、殺虫剤として用いられ
るが、そのまま或いは担体（希釈剤）と混合して粉剤、
粒剤、水利剤、乳剤、油剤その他農薬製剤上慣用されて
いる適当な剤として用いられる。この場合、必要に応じ
て展着剤、乳化剤、湿展剤、固着剤等が適宜用いられ、
又、他の種類の殺菌剤や殺虫剤除草剤、肥料等と併用、
混合することもできる。As mentioned above, the compound of the present invention is used as an insecticide, and it can be used as it is or mixed with a carrier (diluent) to form a powder,
It can be used as granules, aqueous agents, emulsions, oil agents, and other suitable agents commonly used in agrochemical formulations. In this case, spreading agents, emulsifiers, wetting agents, fixing agents, etc. are used as appropriate,
In addition, it can be used in combination with other types of fungicides, insecticides, herbicides, fertilizers, etc.
They can also be mixed.
以下に本発明の処方例を示し、更に具体的に説明するが
、本発明はこれらに限定されるものではない。Prescription examples of the present invention will be shown below and explained in more detail, but the present invention is not limited thereto.
実施例１（乳剤）
表中の化合物 ４５部
キシレ／ ２０部
ツルポール（乳化剤商品名） ３５部以上を混合し
均一の乳剤とする。使用に際しては水で希釈する。Example 1 (Emulsion) Compounds in the table: 45 parts xylem/20 parts Tulpol (emulsifier trade name) 35 parts or more are mixed to form a uniform emulsion. Dilute with water before use.
実施例２（水利剤）
表中化合物 ２０部
硅藻土、クレー混合物 ７５部
ポリオキシエチレン
アルキルフェノール
エーテル系乳化剤 ５部
以上を混合粉砕して水和剤となし、使用に際して水に懸
濁して散布する。Example 2 (Irrigation agent) Compound in the table 20 parts Diatomaceous earth, clay mixture 75 parts Polyoxyethylene alkylphenol ether emulsifier 5 parts or more are mixed and ground to make a wettable powder, which is suspended in water and sprayed before use. .
実施例３（粉剤）
表中化合物 ２部タルクとクレー
の混合物 ９８部
以上を混合粉砕して粉剤となし、そのまま散布する。Example 3 (Powder) The compound in the table: 2 parts A mixture of talc and clay At least 98 parts are mixed and ground to form a powder, which is then sprayed as is.
使用量については必ずしも制限はないが、通常は１０〜
１０００ ｐｐｍの濃度にて、１回乃至数回散布する。There is not necessarily a limit on the amount used, but it is usually 10~
Spray once to several times at a concentration of 1000 ppm.
二１発明の効果
以下、本発明の効果について代表的な試験例を示し、更
に具体的に説明するが、これらは単なる例示であり、従
って、本発明はこれらのみに限定されないことは言うま
でもない。21 Effects of the Invention Below, the effects of the present invention will be explained in more detail by showing typical test examples, but these are merely illustrative, and it goes without saying that the present invention is not limited to these.
ト
試験例１ ハスモンヨ４つ幼虫に対する効果各供試化合
物の５００ ｐｐｍ、１００ ｐｐｍ濃度の薬液を調整
した。その中に直径３．５ ｃｍの円形に切り抜いたキ
ャベツ葉を浸漬し、風乾後シャーレに入しハスモンヨト
ウの３令幼虫を放った。Test Example 1 Effect on 4 larvae of Aspergillus japonica A chemical solution containing each test compound at a concentration of 500 ppm and 100 ppm was prepared. A cabbage leaf cut into a circle with a diameter of 3.5 cm was immersed in the solution, air-dried, and then placed in a petri dish to release third-instar larvae of Spodoptera japonica.
シャーレは２５℃恒温室に静置し、処理４日後に生死車
数を調べ、死亡率を算出した。The petri dish was left in a constant temperature room at 25°C, and 4 days after the treatment, the number of live and dead animals was counted to calculate the mortality rate.
結果は３反復の平均値で示した。The results are shown as the average value of 3 replicates.
ハスモンヨトウに対する効果
試験例２ コナが幼虫に対する効果
各供試化合物の５００ｐｐｍ、１１００ｐｐ濃度の薬液
を調整した。その中に直径３．５ ｃｍの円形に切り抜
いたキャベツ葉を浸漬し、風乾後シャーレに入れコナガ
の３令幼虫を放った。Effect test example 2 on effect on Spodoptera larvae Effect on Kona larvae Chemical solutions of each test compound at concentrations of 500 ppm and 1100 ppm were prepared. A cabbage leaf cut into a circle with a diameter of 3.5 cm was immersed in the solution, air-dried, and then placed in a petri dish to release third-instar larvae of the diamondback moth.
シャーレは２５℃恒温室に静置し、処理４日後に生死車
数を調べ、死亡率を算出した。The petri dish was left in a constant temperature room at 25°C, and 4 days after the treatment, the number of live and dead animals was counted to calculate the mortality rate.
結果は３反復の平均値で示した。The results are shown as the average value of 3 replicates.
コナかに対する効果
試験例３ ナミハダニの成虫に対する効果直径７０のプ
ラスチック製カップに溶かした寒天を注入し、その上に
直径３．５ ａｒ＋の円形に切り抜いた４７２７葉をの
せ、寒天がかたまった後にナミハダニ成虫を接種した。Effect on Kona mosquitoes Test example 3 Effect on adults of two-spotted spider mites Pour melted agar into a plastic cup with a diameter of 70 mm, place a 4727 leaf cut out in a circle with a diameter of 3.5 ar+ on top, and after the agar hardens, two-spotted spider mites will be removed. Adult worms were inoculated.
ナミハダニが落ちついた後、各供試化合物の５００ｐｐ
ｍ、１０１００ｐｐ度薬液を３ゴあて散布した。２口径
成虫の生死を判別し、死亡率を算出した。After the two-spotted spider mites have settled down, add 500 pp of each test compound.
10,100 pp strength chemical solution was sprayed in 3 doses. The 2-caliber adults were determined to be alive or dead, and the mortality rate was calculated.
結果は３反復の平均値で示した。The results are shown as the average value of 3 replicates.
ナミハダニ成虫に対する効果
試験例４ ナミハダニの卵に対する効果直径７ｃｒｎの
プラスチック製カップに溶かした寒天を注入し、その上
に直径３．５Ｃ１ｎの円形に切り抜いたインケ゛ン葉を
のせ、寒天がかたまった後にナミハダニ成虫を接種した
。２５℃恒温室で２４時間放置した後、成虫を除去し、
魔王された卵に対し、各供試化合物の５００ ｐｐｍ
、 １００ ｐｐｍ濃度薬液を３ ｍｌあて散布した。Effect on two-spotted spider mite adults Test example 4 Effect on two-spotted spider mite eggs Pour melted agar into a plastic cup with a diameter of 7 crn, place a circularly cut spider mite leaf with a diameter of 3.5 cm on top, and after the agar hardens, the two-spotted spider mite adults was inoculated. After leaving it in a constant temperature room at 25°C for 24 hours, remove the adults.
500 ppm of each test compound to demonized eggs
, 3 ml of a 100 ppm concentration chemical solution was sprayed.
７口径卵および郷化幼虫の生死を判別し、それぞれの死
亡率を算出しも結果は３反復の平均値で示した。The 7-caliber eggs and the larvae were determined to be alive or dead, and the respective mortality rates were calculated, and the results are shown as the average value of 3 replicates.
Claims (1)
低級アルキル基、又は低級アルコキシ基を、ＺはＲ＿１
Ｒ＿２ＮＨ、又は含窒素複素環化合物（低級アルキル基
で置換されても良い。）を表わす。但し、Ｒ＿１、Ｒ＿
２は各々独立に水素原子、低級アルキル基、低級アルケ
ニル基、シクロアルキル基、フェニル基（ハロゲン原子
、又はメチル基で置換されても良い。）、又は複素環式
基を表わす。〕で示されるホウ素化合物を有効成分とし
て含有する殺昆虫、殺ダニ、殺線虫剤。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are each independently a hydrogen atom, a halogen atom,
a lower alkyl group or a lower alkoxy group, Z is R_1
Represents R_2NH or a nitrogen-containing heterocyclic compound (which may be substituted with a lower alkyl group). However, R_1, R_
Each of 2 independently represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a cycloalkyl group, a phenyl group (which may be substituted with a halogen atom or a methyl group), or a heterocyclic group. ] An insecticide, acaricide, or nematocide containing a boron compound as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10684886A JPS62277307A (en) | 1986-05-12 | 1986-05-12 | Insecticide containing boron compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10684886A JPS62277307A (en) | 1986-05-12 | 1986-05-12 | Insecticide containing boron compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62277307A true JPS62277307A (en) | 1987-12-02 |
Family
ID=14444055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10684886A Pending JPS62277307A (en) | 1986-05-12 | 1986-05-12 | Insecticide containing boron compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62277307A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983590A (en) * | 1990-03-12 | 1991-01-08 | Chevron Research And Technology Company | Fungicidal triazole bis(triphenylboranes), derivatives thereof and use thereof |
| US4983589A (en) * | 1989-12-14 | 1991-01-08 | Chevron Research And Technology Company | Fungicidal imidazole diphenylaliphaticboranes and derivatives thereof |
| US5051514A (en) * | 1989-12-14 | 1991-09-24 | Chevron Research And Technology Company | Process and intermediates for preparing fungicidal imidazole diphenylaliphaticboranes and derivatives thereof |
| US5075292A (en) * | 1990-04-12 | 1991-12-24 | Chevron Research And Technology Company | Fungicidal organo diborane alkanes and derivatives thereof |
| US5091377A (en) * | 1990-12-14 | 1992-02-25 | Chevron Research And Technology Company | Trisubstituted silylalkyl 1,2,4-triazole and imidazole phenyl borane derivatives |
| EP0624315A1 (en) * | 1993-05-07 | 1994-11-17 | American Cyanamid Company | Diaryl(pyridinio and isoquinolinio) boron fungicidal agents |
| WO1997011952A1 (en) * | 1995-09-25 | 1997-04-03 | Zeneca Limited | Fungicides |
| WO1997011951A1 (en) * | 1995-09-25 | 1997-04-03 | Zeneca Limited | Fungicides |
| JP2003527401A (en) * | 2000-03-17 | 2003-09-16 | バーゼル、ポリオレフィン、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | Salt-like compounds, process for their preparation and their use in catalyst compositions for the production of polyolefins |
| WO2007149952A2 (en) * | 2006-06-23 | 2007-12-27 | Invista Technologies S.A.R.L. | Process for making solid tri phenylboron- pyridine |
-
1986
- 1986-05-12 JP JP10684886A patent/JPS62277307A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983589A (en) * | 1989-12-14 | 1991-01-08 | Chevron Research And Technology Company | Fungicidal imidazole diphenylaliphaticboranes and derivatives thereof |
| EP0432987A2 (en) * | 1989-12-14 | 1991-06-19 | Chevron Research And Technology Company | Fungicidal organoborane imidazole compounds and intermediates therefor |
| US5051514A (en) * | 1989-12-14 | 1991-09-24 | Chevron Research And Technology Company | Process and intermediates for preparing fungicidal imidazole diphenylaliphaticboranes and derivatives thereof |
| US4983590A (en) * | 1990-03-12 | 1991-01-08 | Chevron Research And Technology Company | Fungicidal triazole bis(triphenylboranes), derivatives thereof and use thereof |
| US5075292A (en) * | 1990-04-12 | 1991-12-24 | Chevron Research And Technology Company | Fungicidal organo diborane alkanes and derivatives thereof |
| US5091377A (en) * | 1990-12-14 | 1992-02-25 | Chevron Research And Technology Company | Trisubstituted silylalkyl 1,2,4-triazole and imidazole phenyl borane derivatives |
| EP0624315A1 (en) * | 1993-05-07 | 1994-11-17 | American Cyanamid Company | Diaryl(pyridinio and isoquinolinio) boron fungicidal agents |
| WO1997011952A1 (en) * | 1995-09-25 | 1997-04-03 | Zeneca Limited | Fungicides |
| WO1997011951A1 (en) * | 1995-09-25 | 1997-04-03 | Zeneca Limited | Fungicides |
| JP2003527401A (en) * | 2000-03-17 | 2003-09-16 | バーゼル、ポリオレフィン、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | Salt-like compounds, process for their preparation and their use in catalyst compositions for the production of polyolefins |
| WO2007149952A2 (en) * | 2006-06-23 | 2007-12-27 | Invista Technologies S.A.R.L. | Process for making solid tri phenylboron- pyridine |
| WO2007149952A3 (en) * | 2006-06-23 | 2008-02-14 | Invista Tech Sarl | Process for making solid tri phenylboron- pyridine |
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