JPH02191253A - Insecticidal nitro compound - Google Patents
Insecticidal nitro compoundInfo
- Publication number
- JPH02191253A JPH02191253A JP31872689A JP31872689A JPH02191253A JP H02191253 A JPH02191253 A JP H02191253A JP 31872689 A JP31872689 A JP 31872689A JP 31872689 A JP31872689 A JP 31872689A JP H02191253 A JPH02191253 A JP H02191253A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- hydrogen atom
- alkyl
- 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
- 150000002828 nitro derivatives Chemical class 0.000 title claims abstract description 10
- 230000000749 insecticidal effect Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- -1 at about 0-150 deg.C Chemical compound 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000002917 insecticide Substances 0.000 claims abstract description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims abstract description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 239000003517 fume Substances 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01006—Carbon [C]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01039—Yttrium [Y]
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規ニトロ化合物、その製法及び殺虫剤として
の利用に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nitro compounds, their preparation and use as insecticides.
本願出願日前公知の特開昭62−234064号には、
ある種のN−シアノイソチオウレア誘導体が抗潰瘍作用
を有する旨記載され、同じく特開昭63−233903
号には、特開昭62−234064号記載のN−シアノ
イソチオウレア誘導体が昆虫及び植物損傷性線虫防除作
用を有する旨、記載されている。JP-A No. 62-234064, which was publicly known before the filing date of the present application, includes:
It has been described that certain N-cyanoisothiourea derivatives have anti-ulcer effects, also published in JP-A No. 63-233903.
No. 62-234064 describes that the N-cyanoisothiourea derivatives described in JP-A No. 62-234064 have insect and plant-damaging nematode control activities.
この度、本発明者等は下記式(りのニトロ化合物を合成
することに成功した。The present inventors have now succeeded in synthesizing a nitro compound of the following formula (R).
式:
式中、R1は水素原子又はC3−、アルキル基を示し、
でR3はC1−4アルキル基を示し、R4及びRSは、
夫々水素原子又はCl−4アルキル基を示し、そして、
Zは、N原子を少なくとも1ヶ含む、ハロゲン又はC1
−4アルキル置換されていてもよい5〜6員のへテロ環
式基を示す。Formula: In the formula, R1 represents a hydrogen atom or a C3-, alkyl group, R3 represents a C1-4 alkyl group, and R4 and RS are
each represents a hydrogen atom or a Cl-4 alkyl group, and Z is a halogen or a Cl-4 alkyl group containing at least one N atom;
-4 Indicates a 5- to 6-membered heterocyclic group which may be substituted with alkyl.
本発明式(1)の化合物は例えば下記の方法により合成
できる。The compound of formula (1) of the present invention can be synthesized, for example, by the following method.
製法a): (R”が−5−R3を示す場合)式:
式中、R3は前記と同じ、
で表わされる化合物と、
式:
%式%([)
式中、RI及び2は前記と同じ、
で表わされる化合物とを反応させることを特徴とする、
弐:
式中、R1、Rs及びZは前記と同じ、で表わされるニ
トロ化合物の製造方法。Production method a): (When R'' represents -5-R3) A compound represented by formula: where R3 is the same as above, and formula: % formula % ([) where RI and 2 are as above. A method for producing a nitro compound represented by the following formula: wherein R1, Rs and Z are the same as above.
前記式(Ia)の化合物と、
式:
式中、R4及びR5は前記と同じ、
で表わされる化合物とを反応させることを特徴とする、
式:
式中、R1、R4、R5及びZは前記と同じ、で表わさ
れるニトロ化合物の製造方法。The compound of the formula (Ia) is reacted with a compound represented by the formula: wherein R4 and R5 are the same as above, wherein R1, R4, R5 and Z are the same as above. A method for producing a nitro compound, which is the same as .
本発明式(r)のニトロ化合物は強力な殺虫作用を示す
。The nitro compound of formula (r) of the present invention exhibits a strong insecticidal action.
本発明によれば、弐N)のニトロ化合物は意外にも、驚
くべきことには、前掲の特開昭63−233903号記
載の化合物と比較し、実質的に極めて卓越した殺虫作用
を現わす。According to the present invention, the nitro compound of 2N) surprisingly exhibits substantially superior insecticidal activity compared to the compound described in JP-A-63-233903 mentioned above. .
本発明式(1)に於いて、好ましくは、R1は水素原子
又はメチル基を示し、
R3はメチル基を示し、R4及びR5は、夫々水素原子
又はメチル基を示し、
Zは、3−ピリジル基、4−ピリジル基又は2−チアゾ
リル基を示し、ここでこれらへテロ環式基は、クロル又
はメチル置換されていてもよい。In the formula (1) of the present invention, preferably R1 represents a hydrogen atom or a methyl group, R3 represents a methyl group, R4 and R5 each represent a hydrogen atom or a methyl group, and Z is 3-pyridyl. 4-pyridyl or 2-thiazolyl, in which these heterocyclic groups may be chloro- or methyl-substituted.
更には、式(1)に於いて、特に好ましくは、R1は水
素原子又はメチル基を示し、
製法b)に於いて、原料として、例えば、1−(2−ク
ロロ−5−ピリジルアミノ)−1−メチルチオ−2−二
トロエチレンと、メチルアミンとを用いると、下記の反
応式で表わされる。Furthermore, in formula (1), R1 particularly preferably represents a hydrogen atom or a methyl group, and in production method b), as a raw material, for example, 1-(2-chloro-5-pyridylamino)-1 -Methylthio-2-nitroethylene and methylamine are expressed by the following reaction formula.
R3はメチル基を示し、R4及びR5が夫々、水素原子
又はメチル基を示し、
Zは2−クロロ−5−ピリジル基又は2−クロロ−5−
チアゾリル基を示す。R3 represents a methyl group, R4 and R5 each represent a hydrogen atom or a methyl group, and Z represents a 2-chloro-5-pyridyl group or a 2-chloro-5-
Indicates a thiazolyl group.
製法a)に於いて、原料として、例えば、1,1ビスー
メチルチ第2−ニトロエチレンと2−クロロ−5−アミ
ノメチルピリジンとを用いると、下記の反応式で表わさ
れる。In production method a), for example, when 1,1 bis-methylthi-2-nitroethylene and 2-chloro-5-aminomethylpyridine are used as raw materials, the reaction formula is shown below.
上記製法a)に於いて、原料の式(If)の化合物は前
記R3の定義に基づいたものを意味する。In the above production method a), the compound of formula (If) as a raw material means a compound based on the definition of R3 above.
式(II)に於いて、R3は好ましくは、前記の好まし
い定義と同義を示す。In formula (II), R3 preferably has the same meaning as the preferred definition above.
式(II)の化合物は、例えば、Chem、 Ber、
(ケミフェ・ベリヒテ)、100巻、591〜604
頁、1967年に記載される公知化合物であり、その代
表例として、1,1−ビスメチルチ第2ニトロエチレン
を例示できる。Compounds of formula (II) are, for example, Chem, Ber,
(Chemife Berichte), vol. 100, 591-604
1,1-bismethylthi-2-nitroethylene is a representative example thereof.
同様に原料の式(DI)の化合物は前記R1及びZの定
義に基づいたものを意味する。Similarly, the compound of formula (DI) as a raw material means the compound based on the definitions of R1 and Z above.
式(III)に於いて、R1及びZは好ましくは前記の
好ましい定義と同義を示す。In formula (III), R1 and Z preferably have the same meanings as the preferred definitions above.
式(1)の化合物は例えば、米国特許4499097号
、日本化学雑誌83巻、218〜222頁、1962年
等に記載される公知の化合物を包含し、その代表例とし
ては、5−アミノメチル−2−クロロピリジンを例示で
きる。The compound of formula (1) includes, for example, the known compounds described in U.S. Pat. An example is 2-chloropyridine.
上記製法b)に於いて、原料の式(I a)の化合物は
、製法a)により合成される本発明化合物である。In the above production method b), the compound of formula (Ia) as a raw material is the compound of the present invention synthesized by production method a).
また式(IV)の化合物は、前記R4及びR8の定義に
基づいたものを意味する。Further, the compound of formula (IV) means a compound based on the definitions of R4 and R8 above.
式(IV)に於いて、R4及びR5は好ましくは、前記
の好ましい定義と同義を示す。In formula (IV), R4 and R5 preferably have the same meanings as the above preferred definitions.
式(IV)の化合物は有機化学の分野でよく知られたも
のであり、その代表例としては、メチルアミン、ジメチ
ルアミン等を例示できる。The compound of formula (IV) is well known in the field of organic chemistry, and representative examples include methylamine, dimethylamine, and the like.
上記製法a)の実施に際しては、適当な希釈剤として、
すべての不活性な有機溶媒を挙げることができる。When carrying out the above manufacturing method a), as a suitable diluent,
Mention may be made of all inert organic solvents.
斯かる希釈剤の例としては、水;脂肪族、環脂肪族およ
び芳香族炭化水素類(場合によっては塩素化されてもよ
い)例えば、ヘキサン、シクロヘキサン、石油エーテル
、リグロイン、ベンゼン、トルエン、キシレン、メチレ
ンクロライド、クロロホ゛ルム、四塩化炭素、エチレン
クロライド、クロルベンゼン;その他、エーテル類例え
ば、ジエチルエーテル、メチルエチルエーテル、ジーi
s。Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene. , methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene; other ethers such as diethyl ether, methyl ethyl ether,
s.
プロピルエーテル、ジブチルエーテル、プロピレンオキ
サイド、ジオキサン、テトラヒドロフラン;ケトン類例
えばアセトン、メチルエチルケトン、メチル−1so−
プロピルケトン、メチル−is。Propyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl-1so-
Propyl ketone, methyl-is.
−ブチルケトン;ニトリル類例えば、アセトニトリル、
プロピオニトリル、アクリロニトリル:アルコール類例
えば、メタノール、エタノール、13o−プロパツール
、ブタノール、エチレングリコール;エステル類例えば
、酢酸エチル、酢酸アミル;酸アミド類例えば、ジメチ
ルホルムアミド、ジメチルアセトアミド;スルホン、ス
ルホキシド類例えば、ジメチルスルホキシド、スルホラ
ン;および塩基例えば、とリジン等を挙げることができ
る。-butylketone; nitriles such as acetonitrile,
Propionitrile, acrylonitrile: Alcohols such as methanol, ethanol, 13o-propanol, butanol, ethylene glycol; Esters such as ethyl acetate, amyl acetate; Acid amides such as dimethylformamide, dimethylacetamide; Sulfones, sulfoxides such as , dimethyl sulfoxide, sulfolane; and bases such as lysine and the like.
製法a)は、広い温度範囲内において、実施することが
でき、たとえば、約0°C〜約150°C好ましくは約
り0℃〜約90℃の間で実施できる。Process a) can be carried out within a wide temperature range, for example between about 0°C and about 150°C, preferably between about 0°C and about 90°C.
また、反応は常圧の下で行なうのが好ましいが、加圧ま
たは減圧の条件の下で行なうこともできる。Further, although the reaction is preferably carried out under normal pressure, it can also be carried out under conditions of increased pressure or reduced pressure.
製法a)を実施するに当たっては、例えば、式(n)の
化合物1モルに対し、式([1)の化合物を0.9モル
量乃至少過剰、不活性溶媒中で、メルカプタンの発生が
止むまで加熱還流することによって、目的の式(1)の
化合物を得ることができ製法b)の実施に際しては、適
当な希釈剤として、製法a)で例示したと同様のすべて
の不活性な溶媒を挙げることができる。When carrying out production method a), for example, the compound of formula ([1) is added in an amount of 0.9 mole or a slight excess to 1 mole of the compound of formula (n) in an inert solvent, and the generation of mercaptan is stopped. The desired compound of formula (1) can be obtained by heating under reflux to can be mentioned.
製法b)は、広い温度範囲内において実施することがで
き、たとえば、約O′C〜約150℃、好ましくは約り
0℃〜約90°Cの間で実施できる。Process b) can be carried out within a wide temperature range, for example between about O'C and about 150C, preferably between about 0C and about 90C.
また、反応は常圧の下で行なうのが好ましいが、加圧ま
たは減圧の条件の下で行なうこともできる。Further, although the reaction is preferably carried out under normal pressure, it can also be carried out under conditions of increased pressure or reduced pressure.
製法b)を実施するに当たっては、例えば、式(!a)
の化合物1モルに対し、式(IV)の化合物を等モル乃
至少過剰、不活性溶媒中で、反応させることによって、
目的の式(1)の化合物を得ることができる。When carrying out manufacturing method b), for example, the formula (!a)
By reacting the compound of formula (IV) in equimolar to slight excess with respect to 1 mole of the compound in an inert solvent,
The desired compound of formula (1) can be obtained.
本発明の活性化合物は、栽培植物に対し、何ら薬害を与
えることなく、有害昆虫、ダニ、及びセンチユリ類に対
し、的確な防除効果を発揮する。The active compound of the present invention exhibits an accurate control effect against harmful insects, mites, and centipedes without causing any phytotoxicity to cultivated plants.
また本発明化合物は広範な種々の害虫、有害な吸液昆虫
、かむ昆虫およびその他の植物寄生害虫、貯蔵害虫、衛
生害虫等の防除のために使用でき、それらの駆除撲滅の
ために適用できる。Furthermore, the compounds of the present invention can be used to control a wide variety of pests, such as harmful sap-sucking insects, biting insects, and other plant-parasitic pests, storage pests, sanitary pests, etc., and can be applied to exterminate them.
そのような害虫類の例としては、以下の如き害虫類を例
示することができる。昆虫類として、鞘翅目害虫、例え
ば
アズキゾウムシ(Callosobruchus ch
inensis )、コクゾウムシ(Sitophil
us zeasais )、コクヌストモドキ(Tri
boliuw castaneu+i)、オオニジュウ
ヤホシテントウ(Epilachna viginti
octomaculata)、トビイロムナボソコメッ
キ(Agriotes fuscicollis) 、
ヒメコガネ(Anomala rufocuprea)
、コロラドボテドビートル(Leptinotarsa
decemlineata)。Examples of such pests include the following. Insects include Coleoptera pests, such as the bean weevil (Callosobruchus ch.
inensis), brown weevil (Sitophile)
us zeasais), Brown-eared butterfly (Tri
boliuw castaneu+i), giant ladybug (Epilachna viginti)
octomaculata), Agriotes fuscicollis,
Anomala rufocuprea
, Colorado Boted Beetle (Leptinotarsa)
decemlineata).
ジアプロテイカ(Dtabrotica spp、)、
マツノマダラカミキリ (Monochamus al
ternatus)、イネミズゾウムシ(Lissor
hoptrus oryzophilus)、ヒラタキ
クイムシ(Lyctus bruneus) ;鱗翅
目土、例えば
マイマイガ(LymanLria dispar)、ウ
メケムシ(Malacososa neustrla)
、アオムシ(Pieris rapae)、ハスモンヨ
トウ(Spodoptera 1itura)、ヨトウ
(Mamestra brassicae)、ニカメイ
チュウ (Chil。Dtabrotica spp,
Monochamus al.
ternatus), rice weevil (Lissor)
hoptrus oryzophilus), Lyctus bruneus; lepidopterous soils, such as LymanLria dispar, Malacososa neustrla
, Pieris rapae, Spodoptera 1itura, Mamestra brassicae, Chil.
5uppressal is)、アワツメイガ(Pyr
austa nubilalis)、コナマダラメイガ
(Ephestia cautella)、コカクモン
ハマキ(Adoxophyes orana)、コト′
リンガ(Carpocapsa pomonella)
、カプラヤガ(Agrotisfucosa)、ハチミ
ツガ(Galleria mellonella)、コ
ナガ(Plutella +gaculipennis
)、ミカンハモグリガ (Phyllocnistis
cjtrella) ;半翅目虫、例えば
ツマグロヨコバイ(Nephotettix cinc
ticeps)、トビイロウンカ(Nilaparva
ta Iugens)、クヮコナ力イガラムシ(Pse
udococcus comstocki)、ヤノネヵ
イガラムシ(Unaspis yanonensis)
、モモアカアブラムシ(Myzus persicae
)、リンゴアブラムシ(Aphis posi)、ワタ
アブラムシCAphjs gossypiυ、ニセダイ
コンアブラムシ(Rhopalosiphu+i Ps
eudobrass 1cas)、ナシグンバイ(St
ephanitis nashi)、アオカメムシ(N
ezara spp、)、トコジラミ(C3mex I
ectulariua)、オンシッコナジラミ(Tri
aleurodesvaporariorus) 、キ
ジラミ(Psylla spp、) ;直翅目虫、例
えば、
チャバネゴキブリ(Blatella germani
ca)、ワモンゴキブリ(Periplaneta a
aericana)、ケラ (Gryllotalpa
africana)、バッタ(Locusta mi
gratoriamigratoriodes) ;
等翅目虫、例えば、
ヤマトシロアリ(Deucotera+es 5per
atus)、イエシロアリ(Coptoter+nes
forIlosanus) :簀翅目虫、例えば、
イエバエ(Musca domestica)、ネッタ
イシマ力(Asdes aegypti)、タネバエ(
Hylesia platura) 、アカイエカ(C
ulex pipiens)、シナハマダラカ(八no
pheles 5lnensis)、コガタアカイエ力
(Culex tritaeniorhynchus)
、等を挙げることができる。5uppressal is), Pyr
austa nubilalis), Ephestia cautella, Adoxophyes orana, Koto'
Linga (Carpocapsa pomonella)
, Capraya moth (Agrotisfucosa), Honey moth (Galleria mellonella), Diamondback moth (Plutella +gaculipennis)
), Phyllocnistis
cjtrella) ; Hemiptera insects, such as Nephotettix cinc
ticeps), brown planthopper (Nilaparva)
Pse.
Udococcus comstocki), Unaspis yanonensis
, Myzus persicae
), apple aphid (Aphis posi), cotton aphid CAphjs gossypiυ, false radish aphid (Rhopalosiphu+i Ps
eudobrass 1cas), Nasi Gunbai (St
ephanitis nashi), green stink bug (N.
ezara spp, ), bed bugs (C3mex I
ectularia), onicy whitefly (Tri
Psylla spp.; orthoptera, such as the German cockroach (Blatella germani);
ca), American cockroach (Periplaneta a)
aericana), mole (Gryllotalpa)
africana), grasshopper (Locustami
gratoria migratoriodes); Isoptera insects, such as Deucotera+es 5per
atus), Coptoter+nes
forIlosanus): Pteropteran insects, such as the house fly (Musca domestica), the aegypti (Asdes aegypti), the seed fly (
Hylesia platura), Culex pipiens (C
ulex pipiens), Chinese Anopheles mosquito (eight no.
pheles 5lnensis), Culex tritaeniorhynchus
, etc.
またダニ類としては例えば、
ニセナミハダニ(Tetranychus telar
ius)、ミカンハダニ(Panonychus ci
tri)、ミカンサビダニ(AcuIus pele
kassi)、ホコリダニ(TnrronoT@us
spp、)等を挙げることができる。Examples of mites include Tetranychus telar.
ius), orange spider mite (Panonychus ci)
tri), Citrus rust mite (AcuIus pele)
kassi), dust mites (TnrronoT@us
spp, ), etc.
またセンチュウ類としては例えば、
サツマイモネコブセンチュウ (Meloidogyn
e inc。Also, examples of nematodes include the sweet potato nematode (Meloidogyn).
e inc.
gnita)、マツノザイセンチュウ (Bursap
helelenchus l1gn1colus Ma
miya et Kiyohara)、イネシンガレセ
ンチュウ(Aphelenchoides besse
yi)、ダイズシストセンチュウ(Heteroder
a glycines) 、ネグサレセンチュウ(Pr
atylenchus spp、)等を挙げることがで
きる。gnita), Bursap
helelenchus l1gn1colus Ma
miya et Kiyohara), Aphelenchoides besse
yi), soybean cyst nematode (Heteroder
a glycines), Negusare nematode (Pr.
atylenchus spp, ) and the like.
更に、獣医学の医薬分野においては、本発明の新規化合
物を種々の有害な動物寄生虫(内部および外部寄生虫)
、例えば、ダニ類、昆虫類およびぜん虫に対して使用し
て有効である。このような動物寄生虫の例としては、以
下の如き害虫を例示することができる。Furthermore, in the pharmaceutical field of veterinary medicine, the novel compounds of the invention can be used to treat various harmful animal parasites (internal and external parasites).
, for example, are effective against mites, insects and worms. Examples of such animal parasites include the following pests.
ダニ類としては、例えば
カズキダニ(Orani thodoros spp、
)、マダニ(IxodesSill)、)、オウシマダ
=(Boophilus spp、)、等を挙げること
ができる。Examples of mites include Orani thodoros spp.
), Ixodes Sill, ), Boophilus spp, and the like.
昆虫類としては例えば、
ウマバエ(Gastrophilus spp、) 、
サシバエ(Sto+m。Examples of insects include Gastrophilus spp.
Stable fly (Sto+m.
xys spp、)、ハジラミ(Trichodect
es spp、)、サシガス(Rhodnius sp
p、) 、イヌノミ(Ctenocephal 1de
s canis)
等を挙げることができる。xys spp, ), Trichodect
es spp, ), Rhodnius sp.
p, ), dog flea (Ctenocephal 1de
s canis), etc.
本発明ではこれらすべてを包含する生類に対する殺虫作
用を有する物質として広義に、殺虫剤と呼ぶ。In the present invention, substances having an insecticidal effect on living organisms including all of these are referred to as insecticides in a broad sense.
本発明の弐(1)活性化合物は通常の製剤形態にするこ
とができる。そして斯る形態としては、液剤、エマルジ
ョン、懸濁剤、粉剤、水和剤、泡沫剤、ペースト、粒剤
、エアゾール、活性化合物浸潤−天然及び合成物、マイ
クロカプセル、種子用被覆剤、燃焼装置を備えた製剤(
例えば燃焼装置としては、くん蒸及び煙霧カートリッジ
、かん並びにコイル)、そしてULV (コールドミス
ト(cold m1st)、ウオームミスト(warm
m1st) )を挙げることができる。The active compound (1) of the present invention can be formulated into conventional formulations. and such forms include solutions, emulsions, suspensions, powders, wettable powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, combustion devices. Preparations with (
Examples of combustion devices include fumigation and fume cartridges, cans and coils, and ULV (cold mist, warm mist).
m1st) ) can be mentioned.
これらの製剤は公知の方法で製造することができる。斯
る方法は、例えば、活性化合物を、展開剤、即ち、液体
希釈剤;液化ガス希釈剤:固体希釈剤、又は担体、場合
によっては界面活性剤、即ち、乳化剤及び/又は分散剤
及び/又は泡沫形成剤を用いて、混合することによって
行なうことができる。展開剤として水を用いる場合には
、例えば、有機溶媒は、また補助溶媒として使用される
ことができる。These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with a developer, i.e. a liquid diluent; a liquefied gas diluent: a solid diluent, or a carrier, optionally a surfactant, i.e. an emulsifier and/or a dispersant and/or This can be done by using a foam-forming agent and mixing. When using water as a developing agent, for example, organic solvents can also be used as co-solvents.
液体希釈剤又は担体としては、概して、芳香族炭化水素
類(例えば、キシレン、トルエン、アルキルナフタレン
等)、クロル化芳香族又はクロル化脂肪族炭化水素類(
例えば、クロロベンゼン類、塩化エチレン類、塩化メチ
レン等)、脂肪族炭化水素類〔例えば、シクロヘキサン
等、パラフィン類(例えば鉱油留分等)〕、アルコール
類(例えば、ブタノール、グリコール及びそれらのエー
テル、エステル等)、ケトン類(例えば、アセトン、メ
チルエチルケトン、メチルイソブチルケトン又はシクロ
ヘキサノン等)、強極性溶媒(例えば、ジメチルホルム
アミド、ジメチルスルホキシド等)そして水も挙げるこ
とができる。Liquid diluents or carriers generally include aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (
Examples include chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)), alcohols (e.g., butanol, glycols, and their ethers and esters). ), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, etc.), strongly polar solvents (eg dimethylformamide, dimethyl sulfoxide, etc.) and water.
液化ガス希釈剤又は担体は、常温常圧でガスであり、そ
の例としては、例えばブタン、プロパン、窒素ガス、二
酸化炭素、そしてハロゲン化炭化水索類のようなエアゾ
ール噴射剤を挙げることができる。Liquefied gas diluents or carriers are gases at normal temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. .
固体希釈剤としては、土壌天然鉱物(例えば、カオリン
、クレー、タルク、チッーク、石英、アタパルガイド、
モンモリロナイト、又は珪藻上等)、土壌合成鉱物(例
えば、高分散ケイ酸、アルミナ、ケイ酸塩等)を挙げる
ことができる。Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, tick, quartz, attapal guide,
montmorillonite, diatoms, etc.), and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).
粒剤のための固体担体としては、粉砕且つ分別された岩
石(例えば、方解石、大理石、軽石、海泡石、白雲石等
)、無機及び有機物粉の合成杭、そして細粒体又は有機
物質(例えば、おがくず、ココやしの実のから、とうも
ろこしの穂軸そしてタバコの茎等)を挙げることができ
る。Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic piles of inorganic and organic powders, and fine granules or organic substances ( (for example, sawdust, coconut berries, corn cobs, tobacco stalks, etc.).
乳化剤及び/又は泡沫剤としては、非イオン及び陰イオ
ン乳化剤〔例えば、ポリオキシエチレン脂肪酸エステル
、ポリオキシエチレン脂肪酸アルコールエーテル(例え
ば、アルキルアリールポリグリコールエーテル、アルキ
ルスルホン酸塩、アルキル硫酸塩、アリールスルホン酸
塩等)〕、アルブミン加水分解生成物を挙げることがで
きる。Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfones); salts, etc.)] and albumin hydrolysis products.
分散剤としては、例えばリグニンサルファイド廃液そし
てメチルセルロースを包含する。Dispersants include, for example, lignin sulfide waste liquor and methylcellulose.
固着剤も、製剤(粉剤、粒剤、乳剤)に使用することが
でき、斯る固着剤としては、カルボキシルメチルセルロ
ースそして天然及び合成ポリマー(例えば、アラビアゴ
ム、ポリビニルアルコールそしてポリビニルアセテート
等)を挙げることができる。Adhesives can also be used in the formulations (powders, granules, emulsions), such adhesion agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. Can be done.
着色剤を使用するごともでき、斯る着色剤としては、無
機顔料(例えば酸化鉄、酸化チタンそしてプルシアンブ
ルー)、そしてアリザリン染料、アゾ染料又は金属フタ
ロシアニン染料のような有機染料、そして更に、鉄、マ
ンガン、ボロン、銅、コバルト、モリブデン、亜鉛のそ
れらの塩のような微量要素を挙げることができる。It is also possible to use colorants, such as inorganic pigments (such as iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron oxides. Mention may be made of such trace elements as their salts of , manganese, boron, copper, cobalt, molybdenum, zinc.
該製剤は、例えば、前記活性成分を0.1〜95重量%
、好ましくは0.5〜90重量%含有することができる
。The formulation contains, for example, 0.1 to 95% by weight of the active ingredient.
, preferably 0.5 to 90% by weight.
本発明の式(I)活性化合物は、それらの商業上、有用
な製剤及び、それらの製剤によって調製された使用形態
で、他の活性化合物、例えば、殺虫剤、毒餌、殺菌剤、
殺ダニ剤、殺センチュウ剤、殺カビ剤、生長調整剤又は
除草剤との混合剤として、存在することもできる。ここ
で、上記殺虫剤としては、例えば、有機リン剤、カーバ
メート剤、カーボキシレート系薬剤、クロル化炭化水素
系薬剤、微生物より生産される殺虫性物質を挙げること
ができる。The active compounds of formula (I) according to the invention, in their commercially useful formulations and the use forms prepared by them, may be used in combination with other active compounds, such as insecticides, poison baits, fungicides,
It can also be present as a mixture with acaricides, nematocides, fungicides, growth regulators or herbicides. Here, examples of the insecticide include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced from microorganisms.
更に、本発明の式(1)活性化合物は、共力剤との混合
剤としても、存在することができ、斯る製剤及び、使用
形態は、商業上有用なものを挙げることがてきる。該共
力剤は、それ自体、活性である必要はなく、活性化合物
の作用を増幅する化合物である。Furthermore, the active compound of formula (1) of the present invention can also be present as a mixture with a synergist, and such formulations and usage forms include those that are commercially useful. The synergist need not be active itself, but is a compound that amplifies the action of the active compound.
本発明の式(1)活性化合物の商業上有用な使用形態に
おける含有量は、広い範囲内で、変えることができる。The content of active compounds of formula (1) according to the invention in commercially useful use forms can vary within wide limits.
本発明の式(1)活性化合物の使用上の濃度は、例えば
0.0000001〜100重量%であって、好ましく
は、o、ooot〜1重量%である。The concentration for use of the active compound of formula (1) according to the invention is, for example, from 0.0000001 to 100% by weight, preferably from o,ooot to 1% by weight.
本発明式(1)化合物は、使用形態の適合した通常の方
法で使用することができる。The compound of formula (1) of the present invention can be used in a conventional manner suitable for the usage form.
衛生害虫、貯蔵物に対する害虫に使用される際には活性
化合物は、石灰物質上のアルカリに対する良好な安定性
はもちろんのこと、木材及び土壌における優れた残効性
によって、きわだたされている。When used against sanitary pests and stored pests, the active compounds are distinguished by their good stability against alkalis on limestone materials, as well as their excellent residual activity in wood and soil. .
次に実施例により本発明の内容を具体的に説明するが、
本発明はこれのみに限定されるべきものではない。Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.
合成実施例ニー
実施例1゜
2−クロロ−5−アミノメチルピリジン(4,3g)、
1.1−ビスメチルチ第2−二トロエチレン(5,0g
)、エタノール(50ad)の混合物をメチルメルカプ
タンの発生の止むまで加熱還流する。Synthesis Examples Example 1 2-chloro-5-aminomethylpyridine (4.3 g),
1.1-bismethylthi-2-ditroethylene (5.0g
), ethanol (50 ad) is heated to reflux until the evolution of methyl mercaptan ceases.
次いで、減圧下にエタノールを留去し、残渣をカラムク
ロマトグラフィー(エタノール・クロロホルム混合溶出
液)で精製し、目的の1−(2−クロロ−5−ピリジル
メチルアミノ)−1−メチルチオ−2−二トロエチレン
(3,1g)を得る。Next, ethanol was distilled off under reduced pressure, and the residue was purified by column chromatography (ethanol/chloroform mixed eluent) to obtain the desired 1-(2-chloro-5-pyridylmethylamino)-1-methylthio-2- Nitroethylene (3.1 g) is obtained.
mp、151〜154°C
実施例2゜
mp、 165〜168°C
上記実施例1及び2の方法と同様の方法により得られる
本発明化合物を第1表に示し、実施例1及び2の化合物
も表中に示す。mp, 151-154°C Example 2 mp, 165-168°C Compounds of the present invention obtained by a method similar to that of Examples 1 and 2 above are shown in Table 1, and the compounds of Examples 1 and 2 Also shown in the table.
(以下余白)
1−(2−クロロ−5−ピリジルメチルアミノ)1−メ
チルチオ−2−二トロエチレン(3,0g)、エタノー
ル(5(ld)の溶液にメチルアミン水溶液(30%、
t3g)を50°Cで滴下し、続いて、同温度で、2時
間攪拌する。室温に冷却すると、目的物は結晶となって
、析出するので、これを濾取し、エタノールで洗えば、
目的の1−(2−クロロ−5−ピリジルメチルアミノ)
−1−メチルアミノ−2−二トロエチレン(1,5g)
が得られる。(Left below) A solution of 1-(2-chloro-5-pyridylmethylamino)1-methylthio-2-nitroethylene (3.0 g) and ethanol (5 (ld)) was added with a methylamine aqueous solution (30%,
t3g) was added dropwise at 50°C, followed by stirring at the same temperature for 2 hours. When cooled to room temperature, the target substance becomes crystals and precipitates, which are collected by filtration and washed with ethanol.
Target 1-(2-chloro-5-pyridylmethylamino)
-1-methylamino-2-nitroethylene (1.5g)
is obtained.
生物試′Mニー
(特開昭63−233903号)
実施例3゜
有機リン剤抵抗性ツマグロヨコバイに対する試験供試薬
液の調製
熔 剤:キシロール3重量部
乳化剤:ポリオキシエチレンアルキルフェニルエーテル
1重量部
適当な活性化合物の調合物を作るために活性化合物1重
量部を前記量の乳化剤を含有する前記量の溶削と混合し
、その混合物を水で所定濃度まで希釈した。Biological test 'M'ney (Japanese Patent Application Laid-Open No. 63-233903) Example 3 Preparation of test sample solution against organophosphorus agent-resistant black leafhopper Melting agent: 3 parts by weight of xylene Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether Appropriate To make a formulation of the active compound, 1 part by weight of the active compound was mixed with the amount of cuttings containing the amount of emulsifier and the mixture was diluted with water to the desired concentration.
試験方法:
直径12cmのポットに植えた草丈10c+w位の稲に
、上記のように調製した活性化合物の所定濃度の水希釈
液を1ポット当り10m1散布した。散布薬液を乾燥後
、直径1cts、高さ14C11の金網をかぶせ、その
中に有機リン剤に抵抗性を示す系統のツマグロヨコバイ
の雌成虫を30頭放ち、恒温室に置き2日後に死虫数を
調べ殺虫率を算出した。Test method: Rice plants with a plant height of about 10 cm+w planted in pots with a diameter of 12 cm were sprayed with 10 ml per pot of the active compound diluted with water at a predetermined concentration prepared as described above. After the sprayed chemical solution had dried, a wire mesh with a diameter of 1 cts and a height of 14 C11 was covered, and 30 adult female leafhoppers of a strain showing resistance to organic phosphorus agents were released into the mesh, and the number of dead insects was counted after 2 days by placing them in a constant temperature room. The insect killing rate was calculated.
その結果を第2表に示す。The results are shown in Table 2.
第2表
実施例4゜
ウンカ類に対する試験
試験方法:
直径12cmのポットに植えた草丈10cs+位の稲に
、前記実施例3と同様に調製した活性化合物の所定濃度
の水希釈液を1ポット当り10絨散布した。散布薬液を
乾燥後、直径7C1、高さ14C1lの金網をかぶせ、
その中に有機リン剤に抵抗性を示す系統のトビイロウン
カの雌成虫を30頭放ち、恒温室に置き2日後に死生数
を調べ殺虫率を算出した。Table 2 Example 4 Test method for planthoppers: Rice plants with a plant height of about 10 cs+ were planted in pots with a diameter of 12 cm, and a water dilution of the active compound at a predetermined concentration prepared in the same manner as in Example 3 was added per pot. 10 carpets were spread. After drying the sprayed chemical solution, cover it with a wire mesh with a diameter of 7C1 and a height of 14C1L.
Thirty female adult brown planthoppers of a strain that is resistant to organic phosphorus agents were released into the system, placed in a constant temperature room, and two days later, the number of dead and alive was counted to calculate the insect kill rate.
上記方法と同様にして、セジロウンカ、及び有機リン剤
抵抗性ヒメトビウンカに対する殺虫率を算出した。それ
らの結果を第3表に示す。In the same manner as above, the insecticidal rate against the brown-bottomed planthopper and the organophosphate-resistant brown planthopper was calculated. The results are shown in Table 3.
第3表Table 3
Claims (4)
を示し、 R^2は−S−R^3又は▲数式、化学式、表等があり
ます▼を示し、ここでR^3はC_1_−_4アルキル
基を示し、R^4及びR^5は、夫々水素原子又はC_
1_−_4アルキル基を示し、そして、 Zは、N原子を少なくとも1ヶ含む、ハロゲン又はC_
1_−_4アルキル置換されていてもよい5〜6員のヘ
テロ環式基を示す、 で表わされるニトロ化合物。(1) Formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In the formula, R^1 represents a hydrogen atom or a C_1_-_4 alkyl group, and R^2 represents -S-R^3 or ▲ Numerical formulas, chemical formulas, tables, etc. etc. ▼, where R^3 represents a C_1_-_4 alkyl group, and R^4 and R^5 are each a hydrogen atom or C_
1_-_4 alkyl group, and Z is a halogen or C_4 containing at least one N atom;
A nitro compound represented by these, which represents a 5- to 6-membered heterocyclic group which may be substituted with 1_-_4 alkyl.
−S−R^3又は▲数式、化学式、表等があります▼を
示し、ここでR^3がメチル基を示し、R^4及びR^
5が夫々、水素原子又はメチル基を示し、 Zが、3−ピリジル基、4−ピリジル基又は2−チアゾ
リル基を示し、ここでこれらヘテロ環式基はクロル又は
メチル置換されていてもよい請求項(1)記載の化合物
。(2) R^1 represents a hydrogen atom or a methyl group, R^2 represents -S-R^3 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^3 represents a methyl group, R^4 and R^
5 each represents a hydrogen atom or a methyl group, and Z represents a 3-pyridyl group, 4-pyridyl group, or 2-thiazolyl group, wherein these heterocyclic groups may be substituted with chloro or methyl. The compound described in item (1).
−S−R^3又は▲数式、化学式、表等があります▼を
示し、ここでR^3がメチル基を示し、 R^4及びR^3が夫々、水素原子又はメチル基を示し
、 Zが、2−クロロ−5−ピリジル基又は2−クロロ−5
−チアゾリル基を示す請求項(1)の化合物。(3) R^1 represents a hydrogen atom or a methyl group, R^2 represents -S-R^3 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^3 represents a methyl group, R^4 and R^3 each represent a hydrogen atom or a methyl group, and Z is a 2-chloro-5-pyridyl group or a 2-chloro-5
- The compound according to claim (1), which exhibits a thiazolyl group.
を示し、 R^2は−S−R^3又は▲数式、化学式、表等があり
ます▼を示し、ここでR^3はC_1_−_4アルキル
基を示し、R^4及びR^5は、夫々水素原子又はC_
1_−_4アルキル基を示し、そして、 Zは、N原子を少なくとも1ヶ含む、ハロゲン又はC_
1_−_4アルキル置換されていてもよい5〜6員のヘ
テロ環式基を示す、 で表わされるニトロ化合物を有効成分として含有する殺
虫剤。(4) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In the formula, R^1 represents a hydrogen atom or C_1_-_4 alkyl group, and R^2 is -S-R^3 or ▲ Numerical formulas, chemical formulas, tables, etc. ▼, where R^3 represents a C_1_-_4 alkyl group, and R^4 and R^5 are each a hydrogen atom or C_
1_-_4 alkyl group, and Z is a halogen or C_4 containing at least one N atom;
An insecticide containing as an active ingredient a nitro compound represented by the following, which represents a 5- to 6-membered heterocyclic group optionally substituted with 1_-_4 alkyl.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31872689A JPH02191253A (en) | 1989-12-11 | 1989-12-11 | Insecticidal nitro compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31872689A JPH02191253A (en) | 1989-12-11 | 1989-12-11 | Insecticidal nitro compound |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63299419 Division | 1988-11-29 | 1988-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02191253A true JPH02191253A (en) | 1990-07-27 |
Family
ID=18102272
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP31872689A Pending JPH02191253A (en) | 1989-12-11 | 1989-12-11 | Insecticidal nitro compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02191253A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1044071C (en) * | 1989-03-10 | 1999-07-14 | 日本特殊农药制造株式会社 | Insecticidal agents |
WO2009001784A1 (en) * | 2007-06-22 | 2008-12-31 | Ishihara Sangyo Kaisha, Ltd. | N-phenyl-methanamine derivative and pest control agent containing the same |
-
1989
- 1989-12-11 JP JP31872689A patent/JPH02191253A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1044071C (en) * | 1989-03-10 | 1999-07-14 | 日本特殊农药制造株式会社 | Insecticidal agents |
WO2009001784A1 (en) * | 2007-06-22 | 2008-12-31 | Ishihara Sangyo Kaisha, Ltd. | N-phenyl-methanamine derivative and pest control agent containing the same |
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